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As the organizer of the 44th
International Chemistry Olympiad (IChO),
the American Chemical Society thanks:
The Dow Chemical Company
Sole IChO Sponsor
The University of Maryland
IChO Host
PUBLISHED BY THE AMERICAN CHEMICAL SOCIETY
Dow Chemical, ACS, and the University of Maryland proudly
and warmly welcome the international student scholars
and their mentors and families to the United States
for the 44th IChO, July 2130, 2012
(www.icho2012.org).
coverwrapOFC.indd 1 7/2/12 1:26 PM
istry students in the world that seeks to stimulate inter-
est in chemistry through creative problem solving;
Whereas the 44th International Chemistry Olympiad will be
held at the University of Maryland, College Park from
July 21 through 30, 2012;
Whereas more than 70 countries and nearly 300 students will
compete in the 44th International Chemistry Olympiad in
theoretical and practical examinations covering analytical
chemistry, biochemistry, inorganic chemistry, organic
chemistry, physical chemistry, and spectroscopy;
Whereas the objective of the International Chemistry Olym-
piad is to promote international relationships in STEM
education (particularly in chemistry), cooperation among
students, and the exchange of pedagogical and scientific
experience in STEM education;
Whereas STEM education at the secondary school level is
critically important to the future of the United States;
and
Whereas the students who will compete in the International
Chemistry Olympiad deserve recognition and support for
their efforts: Now, therefore, be it
Resolved, That the Senate 1
(1) welcomes the 44th International Chemistry 2
Olympiad to the United States; 3
3
(2) recognizes the need to encourage young peo- 1
ple to pursue careers in the fields of science (includ- 2
ing chemistry), technology, engineering, and mathe- 3
matics; and 4
(3) commends the University of Maryland, Col- 5
lege Park for hosting and the American Chemical 6
Society for organizing the 44th International Chem- 7
istry Olympiad. 8
RESOLUTION
Commending the participants in the 44th International
Chemistry Olympiad and recognizing the importance of
education in the fields of science, technology, engineering,
and mathematics to the future of the United States.
Whereas the global economy of the future will require a work-
force that is educated in the fields of science, technology,
engineering, and mathematics (referred to in this pre-
amble as STEM);
Whereas the science of chemistry is vital to the improvement
of human life because chemistry has the power to trans-
form;
Whereas chemistry improves human lives by providing critical
solutions to global challenges involving safe food, water,
transportation, and products, alternate sources of energy,
improved health, and a healthy and sustainable environ-
ment;
Whereas the International Chemistry Olympiad is an annual
competition for the most talented secondary school chem-
112TH CONGRESS
2D SESSION
S. RES. 491
Commending the participants in the 44th International Chemistry Olympiad
and recognizing the importance of education in the fields of science,
technology, engineering, and mathematics to the future of the United
States.
IN THE SENATE OF THE UNITED STATES
JUNE 12, 2012
Mr. COONS (for himself, Mr. BOOZMAN, Ms. MIKULSKI, Mr. ALEXANDER, and
Ms. MURKOWSKI) submitted the following resolution; which was consid-
ered and agreed to
Sen. Chris Coons (D-Del.),
resolution sponsor
coverwrapIFC.indd 1 7/2/12 12:55 PM
PUBLISHED BY THE AMERICAN CHEMICAL SOCIETY
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CLEAN COAL
Slow progress on carbon
capture, sequestration P.37
FRAGRANT METHODS
New fermentation routes
transform old industry P.25
CHEMISTRY OLYMPIAD
International competition returns to U.S. P.12
Serving the chemical,
life sciences,
and laboratory worlds
CENEAR 90 (29) 156 I SSN 0009-2347
VOLUME 90, NUMBER 29
JULY 16, 2012
50 MEETINGS
56 NEWSCRIPTS
53 CLASSIFIEDS
4 LETTERS
3 EDITORS PAGE
COVER: U.S. team member Sidharth Chand of Detroit
Country Day School in Beverly Hills, Mich., prepares for
the International Chemistry Olympiad. He is shown during
the study camp at the U.S. Air Force Academy in Colorado
Springs at which the four-member U.S. team was selected.
Sarah Chambers/U.S. Air Force
45 EXTRACTING OIL AND MINERALS
Two books examine resource scarcity from a
social science point of view.
I am grateful for
the education
I have had. ...
All I want for
our American
students is what
I was given.
MARYE ANNE
FOX, PROFESSOR
OF CHEMISTRY
AND CHANCELLOR,
UNIVERSITY OF
CALIFORNIA, SAN
DIEGO PAGE 48
44 INSIGHTS
We should drop added sugar, whether high-
fructose corn syrup or plain old sucrose, from our
diets, experts say.
42 UNSOLVED HOFMEISTER MYSTERY
After decades of study, the ordering of aqueous
ions based on their effects on proteins still
confounds.
40 CONCENTRATES
32 HELIUM IN SHORT SUPPLY
Despite plentiful reserves of the gas, production
shortfall and supply interruptions threaten users.
37 CLEAN-COAL STALL
As Congress blocks climate legislation, incentives
for carbon capture and sequestration are quashed.
36 CONCENTRATES
30 CHALLENGES FOR CHINAS PHARMA FIRMS
CPhI China highlights how strong competition
and strict standards challenge drugmakers.
25 FERMENTED FLAVORS AND FRAGRANCES
Biobased sensory compounds can mitigate the
sway weather holds over nature-grown supplies.
22 CONCENTRATES
11 EVONIKS PLANS FOR NYLON 12
Firm will build a new plant in Singapore, continue
to repair damaged facility in Germany.
11 FLUSHING OUT LATENT HIV
Newly synthesized bryostatin analogs activate the
viruss dormant form.
10 BIOTECHS SLASH PAYROLLS
Financial problems, development setbacks force
five companies to cut jobs, one to shut down.
10 ROMANCE AMONG DRAGONFLIES
Males of certain species signal sexual readiness
with a vivid red color, thanks to redox chemistry.
9 REGULATING FLAME RETARDANTS
Senators urge EPA to quickly finalize regulation
for seven polybrominated diphenyl ethers.
9 LOCATING DRUG ACTIVES IN TABLETS
Combination of UV methods yields 3-D maps
faster than current standard techniques.
8 PARTNERS FOR ISOBUTYL ALCOHOL
Gevo and Beta Renewables team up to produce
the fuel from cellulosic biomass.
8 FLUORINE GAS IN ITS NATURAL STATE
Researchers in Munich characterize the highly
reactive molecule while its trapped in a mineral.
7 ARSENIC-BASED LIFE REFUTED
Studies disprove claim that bacteria can use
arsenic in place of phosphorus in biomolecules.
INTERNATIONAL
CHEMISTRY
OLYMPIAD
Hosted in the U.S. for the
first time in two decades,
competition will be held on
July 2130 in the Washington,
D.C., area. PAGE 12
QUOTE
OF THE WEEK
COVER STORY
NEWS OF THE WEEK
BUSINESS
GOVERNMENT & POLICY
SCIENCE & TECHNOLOGY
THE DEPARTMENTS
BOOKS
48 TRENDSETTING CHEMISTS
Heritage Day award winners express concern for
the pacesetters of tomorrow.
AWARDS
25
42
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Anions and Metals Analysis in Hydraulic Fracturing Waters
from Marcellus Shale Drilling Operations
The impact of hydraulic fracturing (fracking) in Marcellus Shale on the quality
of environmental waters is being investigated by the U.S. EPA and many state
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the webinar, the challenges of flowback water preparation and the subsequent
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Speakers
Moderator
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Date: July 26th, 2012
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Susan Morrissey, Ph.D.
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Government & Policy,
C&EN
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Key Learning Objectives:
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environmental waters
John Stolz
Director, Center for Environmental
Research and Education,
Professor Biological Sciences,
Duquesne University
Joelle Streczywilk
Senior Group Leader, Metals,
Geochemical Testing
3
WWW.CEN-ONLI NE.ORG JULY 16, 2012
FROM THE EDI TOR
Editor-in-chief
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Copyright 2012, American Chemical Society
Canadian GST Reg. No. R127571347
Volume 90, Number 29
Views expressed on this page are those of the author and not necessarily those of ACS.
THE FEROCIOUS STORM that ripped
across the Midwest and Middle Atlantic
on June 29a derecho, we later learned
left 2 million people without electric-
ity and killed more than 20. Days later,
several hundred thousand people were
still without power, and in the punishing
90-plus-degree heat of that week, utility
companies were being harshly criticized
for being unprepared for the storm and
not responding quickly enough to get ev-
eryone connected again to the grid. Many
politicians also were questioning why
the electrical infrastructure hadnt been
hardened, for instance by placing it un-
derground, to be better able to withstand
such a storm.
The storm and its aftermath left me
with several thoughts. (A personal note:
My wife and I werent unduly affected
by the storm. We lost power for about 24
hours, a thankfully short time. Our house
didnt suffer any damage. I just mention
this because I wasnt in the unfortunate
position of being without air-conditioning
and refrigeration for several days of blis-
tering heat.)
One thought is that we have become
utterly unrealistic about what we, as a mod-
ern, industrialized nation, can be prepared
for. In the wake of numerous natural and
unnatural disasters, politicians and other
public figures regularly insist that the dam-
age and the time it took to repair it showed
that we are just not prepared for handling
such events. You heard it after 9/11, after
Hurricanes Katrina and Irene, and after the
June 29 derecho.
Heres a news flash: There are some
events that no society can afford to be
prepared for to the extent that we have
come to expect. Some quite natural
eventshurricanes, earthquakes, tsuna-
mis, derechoshave such unimaginable
power that the destruction they wreak will
always take days, or weeks, or months to
fix. No society can afford to harden the
infrastructure that supports it to make that
infrastructure immune to such destructive
forces.
That said, we have as a society woe-
fully neglected our infrastructure. Roads,
bridges, ports, levees, water systems,
sewage systems, the electrical grid, and
so much more have been ignored for far
too long. I know, we cant afford anything
anymore. Were mired in debt. Ive said it
before and Ill say it againthats a crock.
The U.S. is still the richest country in the
world by a long shot. What we are is cheap.
Were unwilling to pay enough in taxes to
maintain the infrastructure we and, more
important, our children need to thrive.
Were also neglecting our intellectual
infrastructure, for the same pathetic rea-
sons. As Senior Editor Celia Henry Arnaud
and Senior Editor Jyllian Kemsley reported
so well in the July 2 issue of C&EN, states
are reneging on their commitment to
public higher education (pages 28 and
32). As Assistant Managing Editor Susan
Morrissey observed in the July 9 issue,
the sequestration that looms in 2013, if it
goes into effect, will have a devastating
impact on R&D in the U.S., with agencies
like NIH, NSF, and NASA looking at up
to 20% reductions in their budgets ( page
28). An article in the July 2 Wall Street Jour-
nal on NASAs Mars Science Laboratory,
scheduled to land on Mars in early August,
noted that the U.S. had recently withdrawn
from a partnership with the European
Space Agency for future missions to Mars.
To support the missions, ESA has turned
to Russia, the country we now rely on to
transport U.S. astronauts to the Interna-
tional Space Station. Im willing to bet that
the next humans to set foot on the moon
will be Chinese.
This is not and should not be the path
we continue on. Sequestration, an ill-con-
ceived club designed to force legislators
to reach a fiscal compromise, should be
shelved. The George W. Bush Administra-
tion tax cuts, even more ill-conceived than
sequestration given the wars in Afghani-
stan and Iraq, should be allowed to lapse
on all Americans. The problem is not that
we are broke. The problem is that too many
U.S. citizens are unwilling to contribute
their fair share to supporting the social
contract.
Thanks for reading.
Storm Thoughts
4
THIS WEEK
ONLINE
LETTERS
CHEMISTRY SHOULD
BENEFIT HUMANS
I ENJOYED RUDY BAUMS EDITORIAL
Earth and Its People ( C&EN, April 23,
page 3 ). I wish more people and politicians
agreed with him and the ACS leaders who
wrote the vision statement about using
chemistry for the benefit of Earth and its
people. Fulfillment of that wish seems un-
likely to me now.
In the current electoral climate, ben-
efit for the Earth is not a high priority
for some politicians. Indeed, the effort to
benefit Earth by enforcement of environ-
mental regulations is considered by some
an impediment to growth and prosperity.
In the recent presidential primaries, many
of the candidates talked about eliminat-
ing the Environmental Protection Agency
entirely.
The conflict between economic growth/
prosperity and Earths benefit will play out
dramatically over the next generation or
two. As the pressure to grow the economy
continues in order to get people jobs and
paychecks, I believe politicians will weaken
environmental laws. This will cause ac-
celerated degradation of the environment
and exacerbate the problems of resource
depletion, climate change, overpopulation,
inadequate food supply, and the like. That
course is a downward spiral that humans
are unlikely to avoid.
Chemistry has played a large role in this
downward spiral. In fact, I believe it started
with chemistry, about 5,000 years ago
when humans first learned to make bronze
by smelting copper and tin. Humans
learned how to manipulate chemical bonds
to create wonderful new things. Many bril-
liant chemical discoveries followed. The
list of good things that have come out of
chemistry is long: modern medicines, elec-
tricity, water and sanitation systems, large-
scale food production and preservation,
and many more too numerous to list.
Life is certainly easier and one would
think more pleasurable than before the
Bronze Age. However, the stresses that
modern life has put on Earth through
chemical discoveries may eventually be
its downfall. Burning fossil fuel causes air
pollution and climate change. Modern ag-
riculture relies heavily on toxic pesticides
and nutrients that contaminate soil and
water and work their way into the food
chain. Modern medicine extends life span
significantly, causing strain on health care
resources. For every plus there are signifi-
cant minuses.
I hope solutions to these problems can
be found and a sustainable world economy
can be developed. This economy would not
be dependent on digging, drilling, sawing,
chopping, burning, and extracting Earths
natural resources to the point of total ex-
haustion. The measure of success or failure
for this new economy would not be based
on growth of gross domestic product. The
metric for a sustainable economy should
be based on how it sustains and preserves
Earth. There must be a way to assign value
to human activity ( jobs) that is not related
to the production and sale of large amounts
of material goods.
We chemists let the genie of natural
resource transformation/destruction out
of the bottle. Now we have to figure out a
way to manage and contain it. Let us hope
future generations of scientists, engineers,
and politicians are smart enough to figure
this out before its too late. I am not opti-
mistic, but it is good to see the leadership
of ACS pulling together to advocate using
chemistry to benefit Earth and its people.
Joe Jablonski
Palos Hills , Ill.
Washing Clothes Leaches
Little Titanium Dioxide
Textile manufacturers add titanium
dioxide to some clothing to brighten it
and to prevent the color-fading effects
of ultraviolet light. But environmental
scientists worry about how much of the
compound leaches from laundrys wash
cycle into wastewater and eventually
into the environment. In a new study,
researchers conclude that very little
TiO
2
washes out of clothing.
http://cenm.ag/env83
Zinc Oxide Solar Cells
Resemble Caterpillars
Scientists have been interested in
building dye-sensitized solar cells out
of the semi-
conductor
zinc oxide
because it
has attrac-
tive proper-
ties such as
transparen-
cy and ease
of manufac-
ture. But the
efficiencies
of such solar
cells have
been low. A new study demonstrates a
way to densely pack zinc oxide nano-
wires in caterpillar-shaped solar cells.
The method significantly improves the
cells efficiency.
http://cenm.ag/b8
Chemistry Pop Quiz!
The International Chemistry Olympiad
exam is no piece of cake, even for
veteran chemists. Test your chemistry
knowledge with a few questions from
previous years exams (see page 18).
Then check the answers online.
http://cenm.ag/popquiz
Technique Spots Effects
Of Protein Deamidation
Enzymes inside cells modify amino
acids to change proteins structure
and function. Some amino acids also
undergo a transformation called deami-
dation without the help of an enzyme.
Scientists want to understand how this
spontaneous reaction changes pro-
tein structure. Now researchers have
detected subtle structural changes,
unseen by standard methods, in deami-
dated aggregates of a peptide linked to
type 2 diabetes.
http://cenm.ag/bio29
N
A
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E
T
T
.

UNIFYING SCIENCE Education Stan-
dards takes a very positive approach
toward Next Generation Science Stan-
dards (NGSS), which I believe is a mistake
( C&EN, May 28, page 54 ).
To begin with, national standards are a
bad idea. Children are different, and there-
fore one set of standards does not fit all
needs. Also, standards tend to be dumbed
down so that most students can meet
them. And research has shown that na-
tional standards have no net positive effect
on student learning.
I have carefully studied both the pro-
posed science standards and the framework
on which they are based. My overall impres-
sion is that NGSS advances a politically
correct agenda that sometimes leaves ob-
jectivity by the wayside. This is particularly
evident in sections that promote unguided
macroevolution (common descent), stress
the negative effects of human activity on
the environment (e.g., global warming),
emphasize sustainability and green
initiatives for the future, and promote big-
government solutions to societal problems.
A DIFFERENT TAKE ON
SCIENCE STANDARDS
5
LETTERS
The national science standards move-
ment is really an effort to consolidate
power and control in the hands of the
Department of Education, the teachers
unions, and the science establishment
(including the National Research Council,
National Science Teachers Association,
American Association for the Advance-
ment of Science, and Achieve). Thus the
standards are more a political than an
educational movement. Restoring control
to parents and local school boards would
be the best way to improve K12 education
in the U.S.
Scientific knowledge has traditionally
been obtained by objective experimenta-
tion and observation. The NGSS frame-
work, on the other hand, tries to convert
science into an enterprise that is decided
by consensus. That is, NGSS has brought
together a team of like-minded experts
from the science establishment who seem
more interested in political goals and social
policy than in giving students a balanced,
objective education.
NGSS should be disbanded before it has
the chance to screw up science education
any further.
Robert Lattimer
Hudson , Ohio
HOW TO REACH US

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7
news of the week
T
HE PERIODIC TABLE of life is holding firm.
A year and a half after a study made the con-
troversial claim that a bacterium could weave
arsenic into its biomoleculesthereby expanding the
chemical definition of lifepublications from two in-
dependent teams now refute that claim ( Science , DOI:
10.1126/ science.1218455 ; 10.1126/science.1219861 ).
The new data indicate that the infamous microbe,
known as GFAJ-1, does not incorporate arsenic into
its metabolites or DNA when grown in ultrahigh con-
centrations of arsenic. The work also suggests that
contamination could explain some of the conclusions
drawn in the original report.
The new results provide good evidence that GFAJ-1
does not appear to rewrite the textbooks, says bio-
organic chemist Kent S. Gates at the University of Mis-
souri, who wasnt involved with any of the studies.
A team led by Felisa Wolfe-Simon made a major
splash in 2010 after reporting in the journal Science
that GFAJ-1, which theyd scooped out of Californias
arsenic-rich Mono Lake, survived by using arsenic in
place of phosphorus.
The report sparked a
vociferous backlash. In
2011, when Science pub-
lished the paper in print,
it was accompanied by
eight critiques.
One of the two new
studies was conducted
by an outspoken critic
of the original report,
microbiologist Rosemary
J. Redfield of the Univer-
sity of British Columbia,
along with genomics professor Leonid Kruglyak of
Princeton University and coworkers. Using liquid
chromatography-mass spectrometry, the team veri-
fied that GFAJ-1 DNA had no covalently bound arse-
nic. Their experiments and conclusions have been
public for some time, but this marks the debut of that
work in a peer-reviewed journal. Redfield published
regular updates and results on her blog and published
the manuscript the team submitted to Science to arXiv,
a repository for preprints of research papers.
The other study, from microbial physiologists Julia
A. Vorholt and Tobias J. Erb and colleagues at ETH
Zurich, used induc-
tively coupled plasma
mass spectrometry
and ultrapure reagents
to demonstrate that
phosphorus-starved
GFAJ-1 scavenges trace
amounts of phosphorus
from its culture medium
to survive.
The new works au-
thors are convinced
they have tightly shut
the door on arsenic in-
corporation into biomol-
ecules, Wolfe-Simon,
now at Lawrence Berke-
ley National Laboratory ,
wrote in an e-mail. We
respect the Science edi-
tors and authors of the
current papers but think
low amounts of arsenic incorporation may be challeng-
ing to find and unstable once cells are opened.
Were not trying to rule out that theres not a single
atom of arsenic anywhere, Kruglyak says. The point
is that once were talk-
ing about those types of
levels, the bacteria are not
using it productively to
grow, which was the claim
of the original paper.
In addition to Wolfe-
Simon, the original work
had 11 other coauthors.
Those collaborators
reached by C&EN empha-
sized the need for more
study of GFAJ-1.
What can I say?
Chemistry is vindicated, says Steven
A. Benner of the Foundation for Ap-
plied Molecular Evolution in Florida,
who has disagreed with Wolfe-Simons
interpretations since her findings
were published.If I were Felisa, I would say, It is
clear that our interpretation was wrong and move
on. CARMEN DRAHL
BIOCHEMISTRY: Controversial microbe
is likely a phosphorus scavenger
TWO STUDIES REBUT
ARSENIC-BASED LIFE
Scanning
electron
micrograph
of GFAJ-1.
JULY 16, 2012 EDI TED BY A. MAUREEN ROUHI & NADER HEI DARI
Redfield sent these
GFAJ-1 samples to
her collaborators.
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MORE ONLINE
8
NEWS OF THE WEEK
T
HE BIOBASED CHEMICALS and fuels firm
Gevo has signed a joint development agreement
with Beta Renewables aimed at producing isobu-
tyl alcohol from cellulosic biomass. Beta Renewables
is a cellulosic sugars joint venture between investment
company TPG and engineering firm Chemtex, an arm
of the Italian chemical producer Mossi & Ghisolfi.
To date, Gevos commercialization strategy has fo-
cused on retrofitting midwestern ethanol facilities that
use corn sugar as a feedstock. It will use
the facilities to produce isobutyl alcohol
for the chemical and fuel markets.
Using cellulosic biomass should allow
Gevo to access a larger carbohydrate pool,
which helps keep costs down and enables
production facilities in regions of the world
rich in biomass resources, said Gevos
chief operating officer, Christopher Ryan,
while announcing the agreement last week
at the Biomass 2012 conference in Wash-
ington, D.C. In June, Gevo revealed plans
to start a cellulosic isobutyl alcohol facility in Malaysia in
a partnership with national and local governments.
Beta Renewables will contribute its Proesa technol-
ogy for enzymatic pretreatment of nonfood biomass,
including agricultural waste, to produce cellulosic
sugars. The sugars can then be fermented by Gevos
isobutyl alcohol-producing microbes.
Another goal of the collaboration will be to make
biobased jet fuel as part of a U.S. Department of Defense
project to expand fuel sourcing beyond petroleum fuels.
The program aims to produce cost-competitive cellu-
losic jet fuel for the military. Gevo is a member of a task
force that is working to certify alcohol-derived jet fuel
with ASTM International, a standards organization.
Gevo also announced that it has begun producing
isobutyl alcohol at its retrofitted plant in Luverne,
Minn. Some of the initial production will go to South
African chemical and fuel firm Sasol and other custom-
ers the firm has lined up. We still have a lot of work to
do: improve plant reliability, improve yields, improve
throughput, and improve quality. With any new tech-
nology, there is a lot to learn, Gevo CEO Patrick R.
Gruber said in a statement.
Successful production at the Luverne plant will
please Gevos investors, points out Mike Ritzenthaler, a
stock analyst at investment bank Piper Jaffray. A current
concern for investors is Gevos ongoing patent litigation
with competitor Butamax (C&EN, June 4, page 18). For
now, investors couldnt care less about whats going on
in cellulosics, he says. MELODY BOMGARDNER
FEEDSTOCKS: Partnership aims to
produce isobutyl alcohol from cellulose
GEVO AND BETA
JOIN FOR BIOMASS
Gevo recently
began isobutyl
alcohol
production at this
fermentation plant
in Luverne, Minn.
G
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V
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F
LUORINE GAS (F
2
) , which has been called chem-
istrys hellcat, is so reactive that chemists have
long assumed it does not occur in nature. Now
researchers in Munich have evidence that the gas exists
naturally, trapped inside a dark purple fluorite mineral
called antozonite ( Angew. Chem. Int. Ed., DOI: 10.1002/
anie.201203515).
The discovery resolves a nearly 200-year-old de-
bate about why the mineral, known as stinkspar or
fetid fluorite, smells so bad when it is crushed. Since
antozonite was documented in 1816 as making fluorite
miners in Bavaria sick to their stomachs, chemists have
blamed the stench on several compounds, including I
2
,
Cl
2
, and ozone. F
2
was suspected as the smelly compo-
nent in 1891 by the French scientist Henri Moissan, who
later won the Nobel Prize for isolating the element. But
many chemists at the time responded that it cant be
true, says Florian
Kraus , a fluorine researcher at the
Technical University of Munich.
Kraus and collaborators,
including Jrn Schmedt auf der Gnne of Ludwig
Maximilian University, have found the first in situ
evidence that F
2
is the culprit. After grabbing samples
of antozonite from beside the highway in Wlsendorf,
Germany, near the area that once made miners sick,
they analyzed pea-sized chunks with solid-state nucle-
ar magnetic resonance spectrometry. The technique
allowed them to detect fluorine gas inside the rock
without breaking it open.
This is the first time fluorine gas has been charac-
terized in nature, says Alain Tressaud, research direc-
tor emeritus at the French National Center for Scien-
tific Research in Bordeaux. It is a fundamental result.
The researchers propose that natural uranium de-
posited in the mineral reacts with fluorite as it decays,
generating species that combine to form fluorine gas,
which is trapped in the mineral matrix. Calcium clusters
formed in the process create the minerals dark color.
So what is the telltale smell like? Tressaud says it is
fitting that a Frenchman first isolated fluorine, because
it has a garlic-type smell. Schmedt auf der Gnne
begs to differ: At high dilution, he says, its like a
perfume. DEIRDRE LOCKWOOD
ANALYTICAL CHEMISTRY:
Researchers resolve long-debated
stink from a fluorite mineral
FIRST FLUORINE GAS
FOUND IN NATURE
Antozonite samples
prepared for
analysis.
Artificial, colorless
fluorite (CaF
2
, left)
next to antozonite.
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NEWS OF THE WEEK
A
LASER-BASED scanning microscopy method
can map the three-dimensional distribution
of active pharmaceutical ingredients (APIs)
in drug tablets and powdered samples faster and with
greater sensitivity than standard methods used for
drug analyses, according to work reported in Analytical
Chemistry (DOI: 10.1021/ac300917t ). The study may
lead to rapid tests for quality control and drug stability
as well as for detecting counterfeits.
Drug manufacturers evaluate the spatial distribu-
tion, crystallinity, and other properties that influence
drug stability, bioavailability, and efficacy to ensure
their uniformity in solid drug formulations. X-ray
powder diffraction and Raman spectroscopy are com-
monly used techniques, but they suffer from various
shortcomings. The X-ray method, for example, is fairly
insensitive; its detection limit is often on the order of
1% for an API in a background of inactive drug formula-
tion compounds (excipients). Imaging by Raman spec-
troscopy often requires long data acquisition times
several hours per frameand is subject to spectral
interference from excipients.
Scott J. Toth, Garth J. Simpson , and Lynne S. Taylor
of Purdue University and coworkers have devised a
technique that overcomes limitations of the X-ray and
Raman methods. It combines ultraviolet nonlinear
optical imaging and UV fluorescence methods and gen-
erates data from the two methods simultaneously. The
team evaluated the method by using it to analyze the
antifungal compound griseofulvin, which is a model
API, and tadalafil, which is the API in Cialis, a drug to
treat erectile dysfunction.
The new method yields analyte signals that can be
10,000 times the size of signals derived from excipi-
ents if the API is chiral, which is true for some 80%
of relatively new drugs. That level of signal intensity
leads to a 1,000-fold increase in detection sensitiv-
ity over X-ray powder diffraction. In addition, data
acquisition time drops from hours per image, which is
required for Raman imaging, to just minutes per image.
The reported
detection sensitivi-
ties for pharmaceu-
tical compounds
are nothing short
of impressive,
says Eric O. Potma ,
a chemistry pro-
fessor and laser
imaging specialist
at the University
of California, Ir-
vine . Potma adds
that the methods
sensitivity and non-
destructive nature
set the stage for a
much larger role
for nonlinear optics
in detecting and
identifying chemi-
cal compounds in common products, including drugs,
cosmetics, and food items.
Shawn Yin, a principal scientist at Bristol-Myers
Squibb , comments that the new method will provide
drug formulators with an alternative technique to
determine API particle size and distribution in tablets
and capsules. Ensuring drug uniformity is a key param-
eter in controlling a products efficacy and safety, he
adds. MITCH JACOBY
ANALYTICAL CHEMISTRY: Combo
method quickly maps 3-D
distribution of active ingredients
LOCATING DRUGS
SENSITIVELY
DRUG MAP A laser scanning method maps
the positions of crystals of griseofulvin in a
solid drug sample by simultaneously detecting
the compounds nonlinear optical (blue) and
uorescence (green) signals. Overlapping regions
are shown in red.
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Twenty-six senators are urging EPA to
swiftly finalize a regulation for a group of
brominated flame retardants.
In a letter sent last week to EPA Admin-
istrator Lisa P. Jackson, the lawmakers
called a recent EPA proposal on seven
polybrominated diphenyl ethers (PBDEs)
an important first step toward protecting
Americans from the risks posed by these
pervasive chemicals. The compounds are
linked to adverse nervous system effects
and disruption of thyroid hormone levels
and may potentially cause cancer.
Six of the PBDEs are no longer made in,
or imported into, the U.S. Albemarle, Chem-
tura, and ICL Industrial Products, which
make the seventh chemical, decaBDE, have
announced they will stop U.S. sales of the
substance by the end of 2013.
EPAs proposal under the Toxic Sub-
stances Control Act (TSCA) would re-
quire companies that intend to make or
import any of the seven PBDEs, including
in products, to notify the agency before
doing so. In addition, any company mak-
ing or processing certain commercial
mixtures of PBDEs would have to con-
duct health and safety tests on the for-
mulations. EPA is expected to finalize the
regulation in 2013.
The 21 Democrats, three Republicans,
and two Independent senators told Jack-
son that the time it is taking to finalize
regulation for the seven compounds
underscores why TSCA needs to be
reformed. They said it is concerning
that the 1976 law forces EPA to un-
dertake lengthy rule-making processes
merely to secure additional health and
safety data on a chemical of concern and
to receive notifications regarding expan-
sions of its uses. CHERYL HOGUE
FLAME RETARDANTS Senators ask EPA to move quickly to regulate seven brominated compounds
10
NEWS OF THE WEEK
M
ALE DRAGONFLIES of certain species send a
clear sign when theyve reached sexual matu-
rity: They turn bright red. A group of scientists
in Japan now reports that redox chemistry underlies
this so-called nuptial coloration ( Proc. Natl. Acad. Sci.
USA, DOI: 10.1073/pnas.1207114109 ).
This is the first time redox-mediated
body color change has been
discovered in animals.
Unlike most insects,
dragonflies change their col-
or pattern in their adult stage,
although the molecular mechanisms
are poorly understood, says Ryo
Futahashi of Japans National Insti-
tute of Advanced Industrial Science & Technology, who
spearheaded the research. I simply wanted to know
how these color patterns developed.
Futahashi and his coworkers extracted the ommo-
chrome pigments from the epidermis of three species
of dragonfly Crocothemis servilia , Sympetrum darwin-
ianum , and Sympetrum frequens. Males of these species
turn a vibrant red when they reach sexual maturity,
whereas females and immature males are a dull yellow.
The researchers found that the mature males had
greater amounts of the reduced forms of the pigments
xanthommatin and decarboxylated xanthommatin,
which are red. Females and immature males had con-
siderably more of the oxidized forms of these pigments,
which are yellow. The team also discovered they could
turn the females and immature males red by injecting
them with a solution of reducing agent. Mature males
injected with an oxidizing agent underwent a red-to-
yellow change, although it was more subtle.
Although we understand a lot about the molecular
basis for chemical communication within and between
insect species, we know a lot less about the physical
aspects of their communication, such as coloration,
comments James De Voss, a chemistry professor at
Australias University of Queensland, who studies
insect chemistry. Futahashi and coworkers reveal
an elegantly simple method used by nature, based
on the redox state of a pigment present in both males
and females, he says. It will be of interest to learn the
mechanism by which the redox state of these pigments
is itself controlled. BETHANY HALFORD
INSECT CHEMISTRY: Male
dragonflies reduce key pigments
to signal theyre ready to mate
REDOX SIGNALS
ROMANCE
A sexually mature,
red male Sympetrum
darwinianum dragonfly
in tandem flight with a
yellowish female.
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F
ACING FINANCIAL PROBLEMS and develop-
ment setbacks, six biotech companies are taking
drastic steps.
A new board at Canadas QLT hopes to fix a precari-
ous financial position. In 2011, the firm lost $30 mil-
lion, despite revenues of $42 million. To align spending
and headcount, the board has cut 146
jobs. The remaining 68 employees
will focus on the firms oral retinoid
program. Advisers will determine
whether to sell or spin off QLTs
punctal plug drug delivery technol-
ogy and possibly partner or sell its
Visudyne eye drug. The firm expects
to break even in 2012.
Another Canadian firm, Car-
diome Pharma , is cutting 85% of
its workforce after Merck & Co.
stopped work on an oral form of Car-
diomes heart drug vernakalant. The
cutbacks will eliminate internal research. Cardiome in-
terim CEO William Hunter wants to preserve cash and
focus on intravenous vernakalant with Merck.
Chelsea Therapeutics is facing a delay in the ap-
proval of its hypotension drug Northera. The North
Carolina company will keep only as many of its 49 em-
ployees as it needs to complete the regulatory process.
It will explore strategic options for its business, which
had no revenues and a $50 million loss in 2011.
To cut costs, Savient Pharmaceuticals will reduce
its workforce by 35%, or about 60 employees. The New
Jersey-based firm had about $10 million in revenues
last year and a loss of $102 million. It predicts $56 mil-
lion in annual savings by 2013 as it focuses on selling its
gout drug Krystexxa.
In light of market pressures, Switzerlands Actelion
is cutting 135 positions, or about 5% of its workforce,
and emphasizing R&D in specialty areas.
Meanwhile, Biolex Therapeutics has shut down
entirely. Having reportedly raised $190 million over
the years from investors, the North Carolina-based
firm lists $38 million in debts in its bankruptcy filing.
Its main asset is Locteron, a controlled-release form of
interferon- to treat hepatitis C.
It is a challenging financing environment, and within
that the fates of individual companies and technologies
move in all sorts of directions, says Glen Giovannetti,
global life sciences leader at Ernst & Young. Long term,
I think we are in a period of contraction. ANN THAYER
EMPLOYMENT: Difficulties lead to
a spate of job cuts and closures
BIOTECH FIRMS
SLASH PAYROLLS
Canadas QLT is
among biotech
firms making deep
cuts.
Q
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11
NEWS OF THE WEEK
Bryostatin 1
Bryostatin analogs
X = Y = H
X = OH, Y = H
X = OCOCH
3
, Y = H
X = OCOCH
3
, Y = OH
X = Y = H, Z = CO
2
CH
3
X = OCOCH
3
, Y = H, Z = CO
2
CH
3
X = OCOCH
3
, Y = OH, Z = CO
2
CH
3
1
2
3
4
5
6
7
O
O
O
HO
OH
OH
O
O
OCH
3
H
3
CO
O O
O
O
HO
O O
O
O
OH
CH
3
O
O O
O
O
O
O
O
O
O
OH
OC
O
OH
O
O
O
Y
Z
X
OH
OH
O
OCH
3 ( )
6
O O
O
OH
CH
3
O
O
O
O
( ) (
6
O
O
O
OH
OC
6
O
Bryostatin 1
O
Y
X
O O O O
OH
Evonik Industries has picked Singa-
pore as the location of a new plant for
nylon 12, a specialty polymer used to
make automotive brake and fuel lines.
The company announced the decision
as it attempts to recover from a plant
explosion that has severely limited sup-
plies of the polymer.
The Singapore plant will have 20,000
metric tons of annual capacity and
should be completed in 2014, Evonik
says. The company currently makes ny-
lon 12 in Marl, Germany.
Nylon 12 supply was already tight on
March 31 when an explosion occurred
at an Evonik plant in Marl that makes
cyclododecatriene (CDT), a critical pre-
cursor for nylon 12. Two workers were
killed in the explosion. The plant supplies
both Evonik and Evoniks main rival in
nylon 12, Arkema.
Weeks after the accident, automak-
ers and their parts suppliers convened
an emergency meeting near Detroit over
a looming nylon 12 shortage (C&EN,
April 23, page 6). There, Evonik and Arke-
ma offered customers substitute nylons.
That same month, the auto industry draft-
ed guidelines for the fast-track approval
of nylon 12 replacements in applications
such as connectors and multilayer tubing.
Evonik says the CDT plant should be
repaired in the fourth quarter, enabling
nylon 12 supplies to return to normal soon
thereafter.
With inventories of nylon 12 now wan-
ing, many consumers will have to resort
to alternative materials this summer,
says Paul Blanchard, North American
director of engineering resins for the
consulting group IHS Chemical . System
suppliers are engaged in submitting test-
ing results to their customers to obtain
fast-track approvals for substitute ma-
terials, he says. The industry, he notes,
was looking for nylon 12 alternatives
even before the explosion because tight
supply drove up prices. ALEX TULLO
ENGINEERING POLYMERS Amid shortage, Evonik plans nylon 12 plant for Singapore
T
HE SYNTHESIS of analogs of a bryostatin natu-
ral product could advance the eradication of
AIDS by ferreting HIV out of its hiding places in
immune cells.
Highly active antiretroviral therapy (HAART), the
current standard for HIV drug treatment, fights the
virus by attacking it in multiple ways simultaneously.
But HAART drugs are toxic and attack only the active
virus. People infected with HIV must take the drugs for
life because of HIVs latencyits tendency to adopt a
dormant provirus form in immune cells, from which
the virus emerges over time to reestablish active infec-
tion. If HIV latency could be eliminated, HAART could
actually cure patients.
Certain natural products can bring the provirus out
of dormancy. Obtained from the bark of a Samoan tree,
the natural product prostratin is being considered for
clinical testing even though its potency in activating
latent HIV is low.
The natural product bryostatin 1 has similar activity
and about 1,000 times the potency of prostratin. Com-
ing from an aquatic invertebrate, it is difficult to obtain
and hence expensive. Bryostatin 1 also causes side ef-
fects such as muscle pain.
Now, Jerome A. Zack , codirector of the UCLA AIDS
Institute; Paul A. Wender , a synthetic organic chemist
at Stanford University; and coworkers report the syn-
thesis of promising analogs. In vitro tests show that the
analogs, dubbed bryologs, are at least as potent
as bryostatin 1 in activating dormant HIV ( Nat.
Chem., DOI: 10.1038/nchem.1395 ). They are also
readily accessible by synthesis, easily modifiable,
and seemingly nontoxic. Studies of the bryologs in
an animal model are in progress.
The work is a significant ac-
complishment, since prostratin
is too impotent, says Douglas
D. Richman , director of the UC San
Diego Center for AIDS Research. The
bryologs are a promising class of drugs for ac-
tivating the latent HIV reservoir, but animal and
clinical confirmation of the agents activity is still
needed, he says.
The new bryologs are an
important discovery, and I am
intrigued with their improved potency, says
Warner C. Greene , director of the Gladstone In-
stitute of Virology & Immunology at
UC San Francisco. They could well
become part of a cocktail of drugs.
Of course, two important issues
are whether they will synergize with other
agents and have acceptable toxicity profiles.
The tour de force complex synthesis
of bryologs is a brilliant realization of the
goals of function-oriented synthesis, says
synthetic chemist Erick M. Carreira of
the Swiss Federal Institute of Technol-
ogy, Zurich. This strategy brings the viral
terrorists out of hiding, where they
can be targeted for destruction. The
combination of the new bryologs
with other current antiretroviral
therapies is highly promising and of-
fers new hope for treatment. STU
BORMAN
DRUG DISCOVERY: Bryostatin
analogs fight dormant HIV, may
be key to HIV/AIDS cure
BRINGING HIV
OUT OF HIDING
Bryostatin 1 (top) and
seven analogs with
similar anti-HIV activity
synthesized by Wender
and coworkers.
12
COVER STORY
AS ATHLETES from nations around the
world prepare to compete in the 2012 Sum-
mer Olympic Games in London later this
month, high school students from most of
those same countries are also in training for
the 44th International Chemistry Olympiad
(IChO), to be held on July 2130 at the Uni-
versity of Maryland, College Park.
Supported by a $2.5 million donation
from Dow Chemical , the American Chemi-
cal Society and the university have taken on
the gargantuan task of hosting the event,
which engages high school students in ex-
ams and laboratory work to test their knowl-
edge in chemistry theory and practice. It will
be held in the U.S. for only the second time
in its history; in 1992, IChO events were split
between Washington, D.C., and Pittsburgh.
This is an especially auspicious time to
be hosting this event because of our nations
focus on science, technology, engineering,
and math education; innova-
tion; and workforce develop-
ment, says ACS Executive
Director & Chief Executive
Officer Madeleine Jacobs. We
are excited about having near-
ly 300 of the best and brightest
students in chemistry from 72
nations, ranging from Argen-
tina to Vietnam, competing for
medals, as well as about show-
ing these aspiring scientists
and engineers some of the most exciting and
innovative scientific and cultural organiza-
tions in the Washington, D.C., area.
44TH INTERNATIONAL
CHEMISTRY OLYMPIAD
For the first time in 20 years THE U.S. HOSTS the competition,
which this year includes teams from 72 nations
SUSAN J. AINSWORTH , C&EN DALLAS

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IT TAKES A VILLAGE, 12
Numerous companies
and individuals pitch in to
plan and run this months
colossal competition.
TEST YOURSELF, 18
Examples of previous years
questions reveal the rigor of
the IChO exams.
WHERE ARE THEY NOW?
20
Former chemistry olympians
relate how participation in
IChO shaped their futures.
13
Given the costs
and complex lo-
gistics associated
with hosting the
event, ACS is truly
indebted to Dows
generosity in
acting as the sole
sponsor of the 44th
IChO, Jacobs says.
I am eternally grateful to Dows CEO, An-
drew N. Liveris, because it was his personal
commitment to science education during
the International Year of Chemistry in 2011
that made this gift possible.
Dows donation will cover most of the
events costs, which are expected to total
$2.7 million. Residual expenses will be off-
set by fees paid by participating countries.
The University of Maryland is providing
significant in-kind support by hosting IChO
on its College Park campus and through
its leadership of the events 15-member
Scientific Committee. That committee has
worked for more than two years to draft
test questions for both the theoretical and
practical examswhich together serve
as the centerpiece of the event, according
to Michael P. Doyle , professor and chair
of the department of chemistry and bio-
chemistry at the university. Doyle is cochair
of the IChO Scientific Committee along
with his department colleague Andrei N.
Vedernikov , a professor and former IChO
gold medalist. See page 18 for test ques-
tions from prior years olympiads, which
demonstrate the exams level of difficulty.
REMARKABLY, planning for this months
IChO began almost three years ago, when
the IChO Steering Committee accepted
the U.S. offer to host the 2012 olympiad,
notes G. Bryan Balazs, an ACS councilor
and immediate past-chair of the ACS Cali-
fornia Section, who now serves on that
committee as chair of this years IChO
Organizing Committee. As chair, Balazs
has coordinated ACS volunteer efforts sur-
rounding the 44th IChO. Planning for the
event has been led by Mary M. Kirchhoff,
director of ACSs Education Division, and
Cecilia C. Hernandez, the divisions assis-
tant director of endowed programs, includ-
ing the olympiad program.
As host of IChO, ACS has been respon-
sible for arranging lodging, meals, trans-
portation, and entertainment for each of
the events participants and attendeesa
total of 650 peoplefor the full 10 days of
the olympiad.
With a few exceptions, the participating
nations will each send a team of four stu-
dents. Qualifying student teams are typical-
ly chosen through a series of regional and
national olympiads held in each country.
For example, the four high school students
who will represent the U.S. were selected
after a nationwide competition, followed
by an intensive two-week study camp for
20 finalists at the U.S. Air Force Academy
in Colorado Springs last month (C&EN,
June 25, page 11).
Accompanying students to next weeks
competition will be two mentors from each
country. Lichtenstein, Nigeria, and Serbia
will be participating in IChO for the first
time this year. In addition, several coun-
tries will be attending IChO as observers;
BEST AND
BRIGHTEST In a
spirit of camaraderie
characteristic of
IChO, students
from around the
world gathered after
finishing their exams
in Tokyo in 2010.
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CHALLENGED
Students work
through the five-
hour theoretical
exam during the
IChO competition
in Cambridge,
U.K., in 2009.
C
A
R
O
L
I
N
E

H
A
N
C
O
X
countries are required to observe for two consecutive years before
they can send a team to compete in the event. Representatives
from El Salvador, the Former Yugoslav Republic of Macedonia, and
Uzbekistan will be observing for the second year, while representa-
tives from Georgia, Montenegro , and South Africa will observe for
the first time. Through this process, those aspiring to compete in
the olympiad learn the intricacies of the event and become familiar
with the rigorous standards and rules for participation.
As is the case during every IChO, students and mentors are sepa-
rated when they arrive in the host city, for test-security reasons,
Hernandez says. In addition, students will be cut off from the use of
cell phones and computers until testing is completed on Thursday,
July 26. Students and mentors will be reunited after Thursdays
exam during a party that will be hosted by the French Embassy.
ON A GIVEN DAY, mentors may be hard at work reviewing, trans-
lating, or arbitrating the scoring of the exams, while students may
be testing or touring.
For the students, ACS has designed a full schedule of recre-
ational and educational activities that will fill the time around the
five-hour lab practical exam, preceded by a 30-minute lab safety
presentation, on Tuesday, and the five-hour theoretical exam on
Thursday, according to Hernandez.
Festivities will begin with the IChO opening ceremony at the
University of Marylands Dekelboum Concert Hall on Sunday, July
22. Nobel Laureate Richard R. Schrock, a professor of chemistry at
Massachusetts Institute of Technology, will
serve as the opening keynote speaker. Sharing
the podium with Schrock will be Maryland
Gov. Martin OMalley and University of Mary-
land President Wallace D. Loh.
Attendees will be welcomed via video by
Nobel Laureate and Priestley Medalist Ahmed
H. Zewail, a professor of chemical physics and
of physics at California Institute of Technology,
who is serving as president of this years IChO. Chair of the ACS Board
of Directors William F. Carroll Jr. will serve as master of ceremonies.
The opening ceremony may be the most exciting part of each
olympiad, notes J. L. Kiappes, a member of the 2004 U.S. olym-
piad team, who is now a member of the Steering Committee and
the IChO Scientific Committee. In a ceremony full of pomp and
circumstance, students, mentors, and organizers come together,
and you begin to really appreciate how so many people from all
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COVER STORY
over the world have been preparing for this
single week, he says. Teams often wear
native costume, meet other students for the
first time, and take pictures together. Its
refreshing to see the camaraderie and spirit
of friendship that goes beyond nationality
or politics.
In the days following the opening cer-
emony, students will get a taste of the U.S.
by attending a baseball game at Camden
Yards, where the Baltimore Orioles will
host the Oakland Athletics, and touring the
National Aeronautics & Space Administra-
tions Goddard Space Flight Center.
They will also take a boat cruise out of
Annapolis, Md.; have dinner and play games
at Dave & Busters restaurant and arcade;
and tour both the National Aquarium
in Baltimore and the Maryland Science
Center. In addition, students will watch
a chemistry demonstration show by ACS
President Bassam Z. Shakhashiri, visit
Kings Dominion amusement park, go shop-
ping, and compete in a Chemistry Idol
competition, which will be modeled after
the television show and talent competition
American Idol.
MEANWHILE, MENTORS will be embark-
ing on their own busy schedule of events.
After the opening ceremony, mentors from
all participating countries will gather to ex-
amine the laboratory facilities where their
students will take the practical exam, tak-
ing inventory of supplies that each student
will need for the exam.
Later, mentors will meet to review the
exam questions prepared by the Scientific
Committee for this years competition.
They will have an opportunity to lobby to
reword or reject questions that they believe
would be outside of the knowledge base of
their students, or to request adjustments
of grading methods.
This deliberation, which can last from
two to six hours, can be very heated,
according to Doyle. That is what we are
going to try to avoid this year. My role is
to keep things moving in these meetings,
making sure that people feel that they have
been treated fairly.
After mentors agree on a final slate of
test questions, they then work to translate
the test into the language used by their
students. Translated tests are fed into an
Internet program that ensures that no part
of the answers has been incorporated into
the questions.
When testing is complete, the IChO
Scientific Committee members and their
assistants will grade the exams. They will
share the graded exams with each countrys
mentors for their review. Mentors have the
opportunity to challenge or question the
grading of the individual exams in scheduled
meetings with members of the committee.
During that time, they might highlight a dif-
ference in notation used by their country or
suggest that partial credit should be award-
ed on a question that was marked as incor-
rect. After any negotiated changes are made,
the final grades are evaluated, revealing who
will win gold, silver, and bronze medals.
The medals will be formally presented
at the closing ceremony, which will be held
on Sunday, July 29, at Georgetown Univer-
sitys Gaston Hall in Washington, D.C. ACS
President-Elect Marinda Li Wu will con-
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COVER STORY
gratulate students on their olympiad per-
formance, and ACS Past-President Bruce
E. Bursten will preside over the closing
ceremony. This event will be followed by a
farewell party and banquet at the National
Building Museum in Washington.
Orchestrating this years competition
and the many events surrounding ithas
been complex. Among the many individuals
and organizations supporting the effort,
Sigma-Aldrich has donated the chemicals
to be used in the lab practical. Other in-kind
donations include calculators from Texas
Instruments, molecular models from Mo-
lecular Visions, copies of the Merck Index
from Merck & Co., backpacks from Nike,
and personal care products from Procter
& Gamble. In addition, ACSs Chemical
Abstracts Service is providing access to
SciFinder for all IChO teams in advance of
the competition; it is also providing hard-
cover journals and umbrellas. Bristol-Myers
Squibb donated funds to offset expenses for
preliminary Scientific Committee meetings
that were held last year. Those who have
pitched in toward the success of the 44th
IChO recognize the value and benefits that
result from their efforts.
BECAUSE THE COMPETITION takes
place on a level playing field, students
who receive IChO medals bring a certain
prestige to their home nations, Doyle says.
That achievement certifies that educators
are in fact doing something right in their
country in preparing students to be inter-
nationally competitive, he adds.
For me, Kiappes says, the olympiad
was a truly life-changing experience. It
really opened my eyes to what an inter-
national endeavor chemistry is. He is
currently enrolled in the Skaggs-Oxford
Program, a Ph.D. program that is a collabo-
ration between Scripps Research Institute
in La Jolla, Calif., and the University of
Oxford, in England. I dont think I would
have actively pursued graduate studies
outside the U.S. if not for the perspective
provided by the olympiad.
Its hard to imagine that any IChO par-
ticipant is unaffected by their immersion in
an international, chemistry-focused world,
even for a week. C&EN talked with several
past chemistry olympians, and each credits
their IChO experience with influencing
their career path (see page 20).
It is very exciting to see the dynamics
and the enthusiasm of all who are involved
in IChO, says Doyle, who attended the
2011 IChO in Ankara, Turkey. They are
participating in something that will be vital
to them all their lives.
Zewail, too, sees great merit in the
olympiad program, which will continue
with competitions in Moscow in 2013 and
Hanoi, Vietnam, in 2014. The International
Chemistry Olympiad is uniquely positioned
for celebrating the beauty and cornucopia
of chemistry with the best young minds, he
says. By intellectually bonding with fellow
students from all over the world, they form
networks for the future.
MORE ONLINE
See a list of those serving on the 44th IChO Scientific
Committee at cenm.ag/oly.
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COVER STORY
18
A proposed mechanism for the reaction between NO and H
2
is given below:

Derive the rate law for the formation of N
2
O from the proposed
mechanism using the steady-state approximation for the intermediate.
1.
Determine the structure of the compounds A-H (stereochemistry is not expected), based on the information
given in the following reaction scheme:

Hints:
A is a well-known aromatic hydrocarbon.
A hexane solution of C reacts with sodium (gas evolution can be observed), but C does not react with chromic acid.

13
C NMR spectroscopy shows that D and E contain only two kinds of CH
2
groups.
When a solution of E is heated with sodium carbonate an unstable intermediate forms at first, which gives F on dehydration.
2
.
IChO
Theoretical
Problems
Name ____________________
___________________________
COVER STORY
THE INTERNATIONAL Chemistry Olym-
piad ( IChO ) exam is no piece of cake, even
for chemists who are considerably older
than the high school students who take it.
Graduate students might be able to
answer most of the questions, but not all of
them, and certainly not within the period
of time thats expected, says Michael P.
Doyle , chair of the chemistry and bio-
chemistry department at the University of
Maryland, College Park, which will host the
olympiad on July 2130. Even established
scientists would find it hard to answer
a number of the questions, he adds. But
its not impossible; at last years IChO in
Ankara, Turkey, a student from the Czech
Republic earned a perfect score on the
theoretical part of the exam. (The other
part of the exam is a lab practical.)
Despite the challenge, chemistry olym-
pians dont seem to regard the experience
as an ordeal. It would destroy me, Doyle
admits, but students come into this with a
visible sign of relaxation and enthusiasm.
They gain their confidence in part from
intensive preparation ahead of IChO. That
advance work includes practice with a large
number of preparatory problems, says
Doyle, who along with his departmental
colleague Andrei N. Vedernikov chaired the
15-member volunteer committee that wrote
this years preparatory and exam problems.
IChO guidelines specify the length of the
exam as well as the topics that can be con-
sidered fair game for questions. Exam writ-
ers can also throw in a few questions from
outside those areas as long as the topics are
introduced in the preparatory questions.
The exam, which is translated by men-
tors from each of the student teams
countries, is presented to the students in
a paper booklet, with a second booklet in
which they write their answers. Answers
are numerical or structural to avoid errors
in translation during grading.
The questions tend to be lengthy and
have multiple parts. Heres a sampling of
some of the briefer questions from previ-
ous years exams.
POP QUIZ!
Match wits with the high school students
who take the IChO EXAM
SOPHIE L. ROVNER , C&EN WASHINGTON
19
A fuel cell is made up of three segments sandwiched
together: the anode, the electrolyte, and the cathode.
Hydrogen is used as fuel and oxygen as oxidant. Two chemical
reactions occur at the interfaces of the three different segments.
The net result of the two reactions is
The hydrogen for the fuel cell is supplied from the hydrolysis
of sodium borohydride. Calculate the standard potential for
the cathode half reaction if the standard reduction potential
for the anode half reaction is
3.
4.
The total synthesis of 1 starts with a reduction of benzene by
sodium in liquid ammonia to give A. The
13
C NMR spectrum of
A consists of two signals at 124.0 and 26.0 ppm.

Trichloroacetyl chloride in the presence of Zn gives a reactive
species S. One equivalent of S undergoes [2+2] cycloaddition
with A to form a racemic product B. The reaction of B with
Zn in acetic acid gives C. Compound C contains only carbon,
hydrogen and oxygen. The
13
C NMR spectrum of C exhibits
three sp
2
carbon signals at 210.0, 126.5, and 125.3 ppm.

The reaction of C with one equivalent of m -chloroperbenzoic
acid ( m -CPBA) in methylene chloride gives D as a major
product. The
13
C NMR spectrum of D also exhibits three
signals in the sp
2
region at 177.0, 125.8, and 124.0 ppm.

Draw the structures of A, B, C, D, and the intermediate S.

5.
Certain varieties of puffer fish, Fugu in Japanese,
are highly prized as foods in Japan. Since the
viscera (especially ovaries and livers) of the fish contain a
potent toxin (tetrodotoxin), food poisoning often results
from its ingestion. Studies on tetrodotoxin have been
performed from the beginning of the 20th century; its
chemical structure was elucidated in 1964. Although
biosynthesis of tetrodotoxin still remains to be clarified,
it is proposed that tetrodotoxin may be biologically
synthesized from L -arginine and isopentenyl diphosphate.
Among the carbons included in tetrodotoxin, circle all the
carbons that are expected to be of L -arginine origin.
Stumped? Find the answers to these quiz questions at http://cenm.ag/popquiz .
MORE ONLINE
20
COVER STORY
AT THE END of the 44th International
Chemistry Olympiad (IChO), after all the
medals are awarded and participants return
to their home countries, they will quietly
join another distinguished groupthat of
the former chemistry olympians.
Since 1968, when the International
Chemistry Olympiad began, thousands of
high school students have participated in
this unique experience. Some have gone on
to successful careers in chemistry, while
others have pursued different passions.
But what these past participants have in
commonand what many say the olym-
piad experience instilled in themis the
confidence to take on new challenges.
When C&EN last checked in with for-
mer U.S. team member Swaine Chen in
2001 (C&EN, June 25, 2001, page 35), he
was pursuing an M.D./Ph.D. from Stanford
University and considering a career as ei-
ther a physician or an academic researcher.
Chen won a gold medal for the U.S. team
in 1992, the only time before this years
competition that the event was held in the
U.S. The chemistry olympiad helped me
an awful lot at that age in shaping what I
thought was possible, he says.
After receiving an M.D./Ph.D. from
Stanford, he went on to do a postdoc at
Washington University in St. Louis . When
he finished in 2008, the economy was in a
recession. Like many
job seekers, Chen found that opportunities
in the U.S. were limited, so he began seek-
ing academic positions abroad.
For the past year and a half, Chen has
been an assistant professor of medicine at
the National University of Singapore , with
a joint appointment at the Genome Insti-
tute of Singapore. Im very happy here,
he says. It was a great move for me. The
university made me a very good offer, and
it was better than the offers I was getting in
the U.S. I do believe I have more resources
here, and Im able to expand my program.
He hopes to return to the U.S. someday,
but in the meantime, hes taking advantage
of all that Singapore has to offer, includ-
ing its proximity to other Asian countries,
which makes international travel easy.
Cuban chemist Nelaine Mora-Diez is also
living and working in a country far from the
one she used to call home. Mora-Diez, who
represented Cuba in the 1991 competition in
Lodz, Poland, is now an associate professor
of chemistry at Thompson Rivers Univer-
sity , in Kamloops, British Columbia.
The olympiad was a turning point in her
life. The opportunity opened doors be-
cause it made me deeper in my knowledge
about chemistry and about what you could
do as a chemist, she says. I remember
when I was in high school, making the
olympiad team was like a dream. I thought
that was something so unreachable.
Mora-Diez knew she wanted to study
abroad. After earning a B.Sc. in chemistry
from the University of Havana in 1996, she
moved to Dalhousie University , in Halifax,
Nova Scotia, where she earned a Ph.D. in
chemistry. She joined Thompson Rivers as
an assistant professor of chemistry in 2003.
There, she is working on computational
physical organic chemistry, and she collab-
orates on research projects with colleagues
from several other nations, including Mexi-
co, Algeria, and Spain. Mora-Diez became a
Canadian citizen in 2004.
MEANWHILE, in South Korea, Turkish
chemist Cafer T. Yavuz is designing new
materials from oxide and organic building
blocks to address environmental challenges.
Yavuz represented Turkey in 1997 in
Montreal and in 1998 in Melbourne, Aus-
tralia, winning a silver and bronze medal,
respectively. He is now an assistant profes-
sor at the Korea Advanced Institute of Sci-
ence & Technology (KAIST).
Im a chemist today because of the
olympiad experience, he says. I would
have gone into computer science if I
werent in the olympiad.
The competition in Montreal marked
his first time visiting a foreign country. I
wouldnt have had the slightest idea of do-
ing my graduate work out of the country if
I werent exposed to other countries and
cultures, he says.
After receiving his B.S. in chemistry from
the Middle East Technical University in Tur-
key, he moved to the U.S., where he earned
a masters and Ph.D. in chemistry from Rice
University. He went on to complete a post-
doc in chemistry and biochemistry at the
University of California, Santa Barbara.
Now, at KAIST, Yavuz is trying to pass
along the mentoring he received as a high
school student. He frequently invites local
high school students to do science projects
with him. Im taking the initiative to bring
them to chemistry because I know how im-
portant it is to change other peoples lives
the same as it changed mine.
His research group is diverse, consisting
of postdocs and grad students from India,
Pakistan, Turkey, and South Korea. Five
people, four countries in my group, Yavuz
says. The labs Turkish postdoc is a former
teammate of Yavuz from the chemistry
olympiad.
Another set of former teammates now
A LOOK BACK
Former CHEMISTRY OLYMPIANS talk about
how their careers have unfolded
LINDA WANG , C&EN WASHINGTON
TEAMWORK Mora-Diez,
shown (second from left)
with her Cuban teammates
at the 1991 IChO in Lodz,
Poland, today collaborates
with scientists from
around the world as a
Canadian professor.
C
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R
T
E
S
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F

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L
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N
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M
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WWW.CEN-ONLI NE.ORG
recession. Like many
T
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21
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S
O
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O
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A

EARLY PROMISE Niskanen
(right), with his Finnish
teammates at the 1995 IChO
in Beijing, is now an engineer
in Finland.
C
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U
R
T
E
S
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O
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A
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find themselves a world apart.
Ding-Shyue (Jerry) Yang and
Kuo-Wei (Andy) Huang were
teammates representing Tai-
wan in the 1993 IChO in Pe-
rugia, Italy. Yang took home
a gold medal, and Huang earned
a silver. Both subsequently majored in
chemistry at National Taiwan University .
Now, Yang is starting a new position as
an assistant professor of chemistry at the
University of Houston, and Huang is an
assistant professor of chemical science
at King Abdullah University of Science &
Technology (KAUST) in Saudi Arabia.
You definitely establish your confi-
dence, particularly in chemistry, and that
confidence is very important, Huang says
of the olympiad experience. You find out
that you can interact with other people and
that may open future opportunities.
After graduating from National Taiwan
University, Yang attended California In-
stitute of Technology , where he earned a
Ph.D. and completed a postdoc. Huang also
moved to the U.S., earning a Ph.D. from
Stanford University and completing a post-
doc at Brookhaven National Laboratory . He
then spent two years as an assistant profes-
sor at the National University of Singapore
before moving to KAUST.
Like Yavuz, Huang also
takes mentoring seriously.
I believe that educa-
tion can really impact the
younger generation, he
says. While working in Sin-
gapore, he participated in
the design of the Singapore
Junior Chemistry
Olympiad. Now, Huang serves as
a consultant for the Saudi chemistry olym-
piad team.
ALEX MEVAY, who earned a silver medal
for the U.S. team in the 1996 IChO in Rus-
sia, embarked on a different kind of adven-
ture after graduating from Massachusetts
Institute of Technology with a degree in
electrical engineering.
I bought a sailboat in the Caribbean and
sailed around Central America and then
back to Boston over eight months, he says.
That was a fantastic experience, because I
didnt realize how burned out I was after un-
dergrad, and it was great to have some time
to get my creative juices flowing again.
He returned to Boston to work for Holo-
sonics , a company developing loudspeaker
technologies. As a hobby, he got involved
with the MIT solar vehicle team designing
battery packs. It
occurred to him that the same technology
could be applied to sailboats.
Today, MeVay is founder of Genasun , a
Cambridge, Mass.-based company develop-
ing lithium batteries for the marine market
as well as solar charge controllers. The com-
pany employs five people and is looking to
expand its product line.
MeVay admits that he never planned on
becoming an entrepreneur, but he says
that the olympiad gave him a very good
sense of self-confidence.
For former chemistry olympians,
it can be a challenge simply to stay in
touch with one another. For many years
after the 1995 IChO in Beijing, Antti J.
Niskanen, who represented Finland in
the competition, maintained a website
with the e-mail addresses and personal
webpages of more than 50 of his peers.
Although he stopped actively maintaining
the website around 2002, Niskanen says
he hopes it allowed friendships to continue
well after the competition ended.
After the competition, Niskanen went on
to earn a masters in chemistry in 2002 from
Helsinki University of Technology (now
Aalto University). He continued working at
the university as a research scientist while
pursuing a Ph.D. in semiconductor technol-
ogy, which he earned this past spring.
Currently, Niskanen is an applications
development engineer for Finnish start-up
company Adaptamat , which specializes in
Ni-Mn-Ga magnetic shape memory alloys.
Although Niskanen did not win
a medal during the olympiad, he
looks back fondly at the experi-
ence. For me, it was an oppor-
tunity to have fun with similarly
minded peers, he says. That
bunch of people has its own
brand of humor, one you cant
find anywhere else.
CROSS-CULTURAL
Huang (top, right) now
runs a research group at
KAUST. Huang (bottom,
second from left),
Yang (right), and other
members of Taiwans
team joined a local guide
(center) at the 1993
IChO in Perugia, Italy.
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22
CHEMICAL FORECAST TRIMMED
The U.S. chemical industrys main trade association is lowering its fore-
cast for the sector this year. In its midyear economic outlook report, the
American Chemistry Council anticipates that U.S. chemical output will rise
by only 0.5% in 2012. Late last year the association predicted 1.2% growth
for the year. ACC attributes the downgrade to the financial crisis in Europe,
economic slowing in China and other emerging markets, and weakness
in U.S. manufacturing. ACC has a brighter view of the years ahead. Owing
in part to the favorable impact of shale gas on the domestic petrochemi-
cal industry, it expects U.S. chemical output growth to rebound to 2.3% in
2013, 2.8% in 2014, and 3.2% in 2015. Citing petrochemical investment,
the association anticipates that capital spending by the U.S. industry will
rise steadily from $35.5 billion in 2012 to $51.5 billion by 2017. MM
ARKEMA TO SELL
STABILIZERS TO PMC
Arkema will sell its tin-based stabilizer
business to PMC Group for an undisclosed
sum. The business manufactures polyvinyl
chloride heat stabilizers and catalysts for
specialty polymer production. It has an-
nual sales of about $220 million, employs
234 people, and operates plants in Carroll-
ton, Ky.; Mobile, Ala.; Vlissingen, the Neth-
erlands; and Beijing. Arkema says the sale
is part of its program to focus on specialty
chemical businesses. In keeping with this
plan, the French company recently com-
pleted the sale of its $1.2 billion-per-year
polyvinyl chloride business to the Klesch
Group. PMC, based in Mount Laurel, N.J.,
acquired Chemturas oleochemicals busi-
ness in 2008. MM
BASF INVESTS IN
EUROPEAN PLANTS
BASF is undertaking a three-digit million
euro investment to increase capacity for
vinylformamide (VFA) and its derivatives.
VFA is polymerized into water-soluble
cationic polymers used to improve the ef-
ficiency of the papermaking process. BASF
will increase VFA monomer and polymer ca-
pacity in Ludwigshafen, Germany, and build
a VFA polymerization line in Zhenjiang,
China. Separately, BASF plans to build a unit
at its Antwerp, Belgium, ethylene cracker to
extract up to 155,000 metric tons per year
of butadiene from a stream of mixed C4s.
BASF says the move is a reaction to a tight
global buta diene market. AHT
OCI ALTERS PLANS
FOR SILICON BOOST
South Koreas OCI will spend $100 million
to expand polysilicon capacity by 10,000
metric tons at a plant in Gunsan, South Ko-
rea. Once the work is completed, the plants
annual production capacity will reach
52,000 metric tons. For OCI, the expansion
follows the postponement of plans to spend
$1.6 billion on a new polysilicon plant in
South Korea. OCI blamed poor economic
conditions in Europe for the delay. Earlier
this year, German polysilicon producer
Wacker Chemie said global overcapacity
dampened its profits in the fourth quarter of
2011 (C&EN, May 7, page 9). JFT
FLAMMA EXPANDS API
PRODUCTION IN ITALY
Flamma , a producer of active pharmaceuti-
cal ingredients, has purchased a former
Archimica manufacturing site in Isso, Italy,
from an Italian bankruptcy court. The
plant, about 20 miles from Flammas facil-
ity in Chignolo dIsola, will more than dou-
ble the companys annual capacity in Italy
to 270 m
3
. Flamma says it will spend $10
million to upgrade the manufacturing and
lab facilities. The acquisition replaces plans
to expand capacity in Chignolo. The firm
also operates a plant in Dalian, China. RM
OAKBIO MAKES PLASTIC
FROM CARBON DIOXIDE
Oakbio , a Sunnyvale, Calif.-based start-up
firm, says it has succeeded in making a bio-
polymer using carbon dioxide from the flue
gas of a cement plant. Lehigh Southwest
Cement in nearby Cupertino provided flue
gas that Oakbio fed to CO
2
-consuming
microbes. Oakbios CEO is Russell How-
ard, who founded the biotechnology firms
PETROBRAS OPENS
BIOFUELS R&D CENTER
Brazilian state oil company Petrobras and
the Federal University of Rio de Janeiro
(UFRJ) have established a center for bio-
fuels at UFRJs Ci-
dade Universitria
campus. Built at a
cost of $2.5 million,
the 22,000-sq-ft
center is equipped with 16 labs and three pi-
lot plants. Researchers at the center will use
biotechnology and chemical engineering
to develop biofuels processes. A Petrobras
process for making ethanol from sugarcane
bagasse, set for commercialization in 2015,
is rooted in research done at UFRJ. AHT
INDIAS JBF PLANS PLANT
USING BP PROCESS
Indias JBF Industries will build a purified
terephthalic acid (PTA) plant using tech-
nology licensed from BP. To be constructed
in Mangalore, in southern India, the poly-
BUSI NESS CONCENTRATES
Maxygen and Codexis. He says the mi-
crobes are also capable of converting the
greenhouse gas into specialty chemicals
and fuels. Novomer , an Ithaca, N.Y.-based
start-up, uses catalysts to convert CO
2
into
polymers. MSR
Petrobras biofuels
center includes
this microalgae
cultivation reactor.
P
E
T
R
O
B
R
A
S
ester intermediate plant will have annual
capacity of 1.25 million metric tons. BP says
the deal represents the first license of its
technology to a nonaffiliated company. BP
itself has 7.5 million metric tons of PTA ca-
pacity and is expanding its plant in Zhuhai,
China. World demand for the intermediate
is about 50 million metric tons, BP says,
and is growing by 7% annually. JFT
23
BUSI NESS CONCENTRATES
SHANGPHARMA MULLS
GOING PRIVATE AGAIN
Less than two years after its initial public
stock offering, the Chinese contract re-
search firm ShangPharma may delist from
RUSSIAN FIRMS GET
DRUG-LICENSING DEALS
Three small Russian firms have struck li-
censing deals with major U.S. pharmaceu-
EVOTEC LICENSES
COMPOUNDS TO JANSSEN
Evotec , a German contract research orga-
nization, has licensed to Janssen Pharma-
ceuticals a portfolio of small molecules and
biologics designed to trigger the regenera-
tion of insulin-producing beta cells. The
antidiabetes compounds were identified
by scientists at Harvard University and
analyzed by researchers at Cure Beta, an
R&D joint venture established last year
by Evotec, Harvard, and Howard Hughes
Medical Institute to develop disease-
state-modifying therapeutic targets. Jans-
sen, a division of Johnson & Johnson, will
pay $8 million up front and could make
milestone payments of up to $300 million
per product. RM
BMS INVESTS IN
PUERTO RICAN SITE
Bristol-Myers Squibb will spend $164 mil-
lion to expand its site in Humacao, P.R. To
be completed by early 2016, the project is
expected to add 82,000 sq ft of manufac-
turing space for type 2 diabetes drugs and
83,150 sq ft for cardiovascular medicines.
In addition, the firm says it will debut a new
active coating process that introduces ac-
tive ingredients into the coating of a tablet.
In 2008, BMS closed its pharmaceutical
chemical plant in Barceloneta, P.R. The
following year it completed a $200 million
expansion in Manati, P.R. MM
SANOFI PASTEUR POISED
FOR RESTRUCTURING
Sanofi Pasteur, the France-based vaccines
subsidiary of Sanofi , is about to be restruc-
tured to improve its profitability. The com-
pany is set to introduce measures to en-
hance the performance of its manufactur-
ing activities and support functions. Sanofi
says that it has begun talks with workers
representatives about the plan but that no
specific job cut numbers have been pro-
posed. The French newspaper Le Figaro re-
ports that the restructuring will lead to the
loss of 2,000 jobs across France. AS
BUSINESS
ROUNDUP
RELIANCE Industries
has picked Technip to
provide process technol-
ogy and engineering ser-
vices for its new ethylene
cracker in Jamnagar in
the Indian state of Guja-
rat. Reliance has not yet
disclosed the capacity of
the new cracker, but it will
be one of the worlds larg-
est, the company says.
SAUDI ARAMCO has
launched a venture
capital unit to invest in
start-up and high-growth
technology firms. Saudi
Aramco Energy Ventures
says it will make invest-
ments in renewable
energy, water, and energy
efficiency businesses.
HUNTSMAN CORP.
has bought the 55%
stake it did not already
own in Huntsman NMG ,
a Russia-based poly-
urethanes joint venture.
Huntsman set up the ven-
ture in 2006 with NMG, a
polyurethanes maker with
headquarters in Obninsk,
near Moscow.
W.R. GRACE has ac-
quired Brazilian concrete
admixtures maker Rheo-
set Indstria e Comrcio
de Aditivos. The firm adds
58 employees and capac-
ity in Rio de Janeiro and
Recife to Grace s existing
operations at Sorocaba
and Bahia.
BHARAT PETROLEUM
of India and LG Chem
of South Korea plan to
build a petrochemical
plant adjacent to Bharat s
refinery in Kochi, India. A
fluid catalytic cracker set
to open in 2016 will gener-
ate 500,000 metric tons
per year of propylene and
allow Bharat to enter the
chemical business, the
partners say.
AESICA says it will create
up to 100 new jobs at its
Queenborough, England,
plant by 2015 as part of
expansion plans for the
site. The contract phar-
maceutical manufacturer
acquired the site from Ab-
bott Laboratories in 2007.
ATMI has formed a joint
development agreement
with IBM aimed at solving
wet-chemistry challenges
in the production of semi-
conductors with 14-nm
circuit lines. ATMI says
the two-year agreement
could result in new chemi-
cal formulations for the
cleaning of semiconduc-
tor wafers.
ADC THERAPEUTICS
and Cancer Research
Technology, the commer-
cial arm of the nonprofit
Cancer Research UK , will
jointly develop antibody-
drug conjugates for use
in oncology. The biotech
firm s pyrrolobenzodi-
azepines will be linked
to anti bodies and pep-
tides developed by the
nonprofit.
AUDEO ONCOLOGY, a
spin-off from the Austra-
lian biotech firm Alchemia ,
has filed the paperwork
for an initial public offering
of stock. The company
has developed drug deliv-
ery technology that links a
cancer drug to hyaluronic
acid, which binds to the
CD44 receptor on tumor
cells. Audeo hopes to raise
as much as $60 million
through its IPO.
These
ShangPharma
labs in Shanghai
may soon be in
private hands.
S
H
A
N
G
P
H
A
R
M
A
the New York Stock Exchange after two
major shareholders offered to buy all of the
shares they do not already own. CEO and
founder Michael Xin Hui, who owns 54%
of ShangPharma, and the private equity
firm TPG Star Charisma, with an 11% stake,
made an offer to buy all additional shares
for as much as $9.50 each. Prior to their
offer, shares in ShangPharma traded for
about $7.00, less than half of their $15 list-
ing price in October 2010. ShangPharmas
board says it will review the offer. JFT
tical companies. Pfizer has granted SatRx,
a company within the ChemRar High-Tech
Center near Moscow, rights to PF-734200.
The compound inhibits dipeptidyl pepti-
dase-4 and is in development for treating
type 2 diabetes. ChemDiv Research Insti-
tute , also at the ChemRar center, will work
with Abbott Laboratories on R&D target-
ing Russian patients. An initial project
will create new forms of existing Abbott
products. Meanwhile, R-Pharm licensed
the hepatitis C protease inhibitor narlapre-
vir from Merck & Co. last month. R-Pharm
will conduct late-stage clinical trials in
Russia and pay royalties to Merck on any
eventual sales. AMT
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25
BUSI NESS
THE FLAVOR AND FRAGRANCE industry
experienced a shortage of patchouli oil in
2010 when soggy weather gave Indone-
sian growers a poor harvest of Pogostemon
cablin, a perennial shrub in the mint family
that is the source of the fragrant oil. That
disappointment was followed by volcanic
eruptions in the islands, which spawned
earthquakes and a tsunami, further dis-
rupting supply.
The patchouli market has since recov-
ered. Prices have come down over the last
couple of months. It is a good moment to
buy now before the demand starts to pick
up, advises Eramex Aromatics , a German
supplier of flavor and fragrance raw materi-
als, in its March 2012 market report.
The same cannot be said for some other
flavor and fragrance raw materials. Among
the difficult-to-source oils, Eramex re-
ports, are bitter orange, grapefruit, rose,
and sandalwood. Price swings and supply
disruptions can be caused by disasters
both natural and man-made. They include
droughts and floods, as well as poaching
and government corruption in the far-flung
regions where many essential-oil crops are
grown by small landholders.
It is no wonder, then, that purchasers
of fine-smelling and -tasting substances
would seek alternatives to nature-grown
materials. Indeed, major flavor and
fragrance houses such as Givaudan , Fir-
menich , and International Flavors & Fra-
grances are intrigued by the possibility of
using biotechnology to produce key com-
ponents of essential oils from abundant
sugar feedstocks via fermentation.
For assistance, they are turning to
the growing number of biotechnology
start-ups that are targeting the flavor and
fragrance industry. These firms, which
include Allylix , Amyris , Isobionics , and
Evolva , claim their microbial platforms can
produce just about any plant-derived mol-
ecule. Once they scale up, they say, supply
shortages will be a thing of the past.
The move toward biotech routes for
these high-value molecules has also at-
tracted interest from the big chemical
firms DSM and BASF. DSM spun off Isobi-
onics in 2008 and has been working closely
with the 10-employee firm since then. In
March of this year, BASF announced that
its venture arm has invested $13.5 million
in San Diego-based Allylix.
Curiously, both Allylix and Isobionics
are promoting the same two citrus mol-
THE SWEET SMELL
OF MICROBES
Flavor and fragrance molecules MADE BY FERMENTATION
promise abundance regardless of the weather
MELODY M. BOMGARDNER , C&EN NORTHEAST NEWS BUREAU
A
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ORANGE
YOU SMART
Richard
Burlingame of
Allylix shows
off a bottle
of valencene
made from
sugar via
fermentation.
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through-put food analyses. The
Agilent 7000B Triple Quadrupole
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26
BUSI NESS
eculesvalencene and nootkatoneas
their first products. Valencene is extract-
ed from the peel of the Valencia orange.
Nootkatone comes from grapefruit peels
but can also be produced from valencene.
Both are currently used in fruit-flavored
beverages and in perfumes but have po-
tential for use in personal care and clean-
ing products.
Industry experts say it is too early to
tell what portion of the market for flavors
and fragrances might move to biotech
production. The overall industry, including
synthetic molecules made from petroleum
feedstocks, was worth $21.8 billion in 2011,
according to flavor and fragrance consult-
ing firm Leffingwell & Associates .
The ability to make high-demand mol-
ecules such as valencene and nootkatone
through fermentation could significantly
alter supply dynamics, says Kalib Kersh, an
analyst at consulting firm Lux Research .
There is potential for biosynthetic routes
to completely replace any natural sources,
he observes.
Beyond the two citrusy heavy-hitters,
though, the scent trail of other likely target
molecules grows faint. Most development
work is done in partnerships similar to
those used by large pharmaceutical com-
VALENCENE
Juicy, orange, sweet,
and woody scent.
Extracted from the
peel of the Valencia orange.
Used in
fragrances and
in flavorings
for beverages
and chewing
gum. Valencene
is also used in
the production
of nootkatone,
the main
component of
grapefruit flavor
and aroma.
FRAGRANCES 101
A Fortuitous Field Of
Flavors & Fragrances
PICROCROCIN
Bitter, saffron
flavor.
Extracted from
saffron, a spice
derived from the flower of the saffron
crocus Crocus sativus . Along with safranal,
it is one of two main saffron volatiles.
Used for
food flavoring
and for its
natural yellow
color. It is an
expensive raw
material with
prices averaging
around $2,000
per kg.
VANILLIN
Strong, sweet, and milky scent.
Main fragrance
component of natural vanilla
extract.
Derived from orchids of the genus Vanilla ,
found mostly in Madagascar. Vanillin can be made
synthetically from lignin-containing wood pulp
waste or from phenol.
Widely used in confectionery and dairy
products. Vanillin is also used in fragrances
for perfumes and cleaning products, and in
flavorings for pharmaceuticals and animal food.
H
O
H
O
O OH
OH
OH
O
H
H
O
OCH
3
HO
SOURCES: Patent filings, International Fragrance Association, PubChem, company information V
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reproducible, right from the start.
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27
panies and their biotech research partners
but under extremely secretive condi-
tions. None of the three major flavor and
fragrance houses responded to C&ENs
requests for interviews.
A search of the patent literature shows
that the flavor and fragrance industry
is looking to biotechnology to produce
complex molecules more cheaply, and
in greater quantities, than is possible by
either chemical synthesis or extraction
from plants. In the case of plant-derived
molecules, for example, a Firmenich pat-
ent lists terpene molecules that could be
made by engineered microbes, including
patchoulol, linalool, nerolidol, valencene,
and sclareol.
Fermentation-derived products may
also replace some chemically synthesized
molecules. The claim is that the process
There is potential for biosynthetic routes
to completely replace any natural sources.
NEROLIDOL
Mild and delicate sweet, floral, green, and woody scent.
Commonly found in the essential oils of many plants
and flowers. It is the main component of neroli oil, derived from the flowers of the bitter
orange tree. Synthetic nerolidol is made from linalool.
Widely used in perfumery and in flavoring for citrus, fruit, and berry complexes.
PATCHOULOL
Earthy, woody,
and camphorous
fragrance.
Derived from Pogostemon cablin,
an herb of the mint family. It is a major
component of patchouli oil, a substance
that contains
at least 24
sesquiterpenes.
Widely used
in perfumery
and to scent
consumer
goods including
paper products
and detergents.
Patchouli oil is used in many types of
incense.
SCLAREOL
A mellow, warm, and
herbal scent.
Derived from
clary sage, which is
commonly grown in the
Mediterranean and has
a history of use as a medicinal herb.
Being
studied for
possible
anticancer
effects.
The natural
essential oil
of clary sage
is used in
aromatherapy
for relaxation.
OH
OH
OH
OH
H
H
OH
OH
LINALOOL
Fresh, sweet, pine, and floral scent.
Component of many essential oils including lavender, rosewood, and coriander. Natural
linalool is extracted from Brazilian rosewood. It also can be derived from citrus peel oils,
from the pine chemicals - and
-pinene, or by total chemical
synthesis.
A common fragrance
ingredient in perfumes, soaps,
detergents, and personal care
products. Linalool is also used to
flavor citrus beverages.
OH
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28
BUSI NESS
would be more environmentally friendly
and produce ingredients that can be la-
beled as natural. Givaudan, for example,
has patented a microbial route to vanillin.
This common flavoring agent, a replace-
ment for costly natural vanilla, is now syn-
thetically derived from phenol.
Kersh suggests that the biotech compa-
nies will start by focusing on commonly
used molecules. For example, citrus peel
extracts are already used in large quanti-
ties, but there is plenty of demand for
more of the essential oils. In the future, he
anticipates, biotech firms will also tackle
molecules that are only available in small
quantities from botanical sources.
If you have a rare compound that you
can only isolate from a particular orchid
that grows in the swamps of Florida, then
only a handful of people in the world can
have access to that. Even with a greenhouse
full of orchids, it may become a top-end
luxury fragrance at exorbitant feedstock
prices of something like a hundred thou-
sand dollars a pound, Kersh says.
With microbial production, however,
a once-rare fragrance or flavor could be
made in much larger quantities. Biotech
manufacturers can supply their customers
with the rare molecule for less than what
they would pay for plant-derived com-
pounds, while expanding production a bit
at a time as new markets open up. Eventu-
ally, Kersh says, the expansion could reach
a scale where the molecule could be used in
common consumer products.
THE UNIVERSE of molecules that could
be made by biotechnology is large. To
replace nature-made scent and flavor in-
gredients, biotechnologists can examine
extracts of blossoms such as lavender,
jasmine, or ylang-ylang. Or they can look at
the stems and leaves of fragrant herbs like
geranium and patchouli. Seeds and fruits
with pungent smell and taste include anise,
coriander, vanilla, and juniper. The palette
expands with the addition of fruit peels,
roots, grasses, evergreen needles, woods,
resins, and balsams.
If the goal is to trade up to fermentation-
produced molecules from those made
by chemical synthesis, possible targets
include esters, ethers, aldehydes, hydrocar-
bons, and ketones.
At Allylix, Chief Executive Officer Caro-
lyn Fritz will narrow down the firms target
molecules only to the broad category of
terpenes, which are found in plants, marine
creatures, and microorganisms. More than
75,000 terpenes have been identified so far,
she tells C&EN, and several hundred thou-
sand more exist in nature.
Fritz explains that scientists developed
chemical synthesis routes to a few simple
monoterpenes in the 1970s and 80s and
found a significant market for them. Then
they went on to look at sesquiterpenes and
diterpenes, but they found they are too
complex and too chiral. The opportunity
we havethe beauty of biologyis that it
produces single isomers, Fritz says. By
metabolically engineering our strains, we
can produce large volumes cost-effectively,
including complex chiral compounds.
Terpenes are made up of multiple iso-
prene units. Whereas monoterpenes con-
tain two isoprenes, sesquiterpenes such as
valencene and nootkatone contain three.
Allylix recently added a third sesquiter-
pene to its product list. Called Epivone, it
is structurally related to -vetivone, one
of the key components of vetiver oil, an es-
sential oil with a rich, woody aroma.
In addition to developing the three ter-
penes on its own, Allylix works in exclusive
arrangements with flavor and fragrance
houses that develop finished products, as
well as with consumer product companies
that create their own formulations.
The DSM spin-off Isobionics, based
in the Netherlands, has a business model
similar to that of Allylix, and also shares
its focus on terpenes. Its newest product
is the sesquiterpene -elemene. Today,
-elemene is obtained via a costly extrac-
tion from ginger root, says Laurent Knoors,
commercial manager at Isobionics. Al-
though -elemene has flavor and fragrance
applications, it is mainly of interest as a
potential anticancer drug.
Knoors stresses that Isobionics link to
DSM is a major advantage. It shares a loca-
tion with several related DSM operations
on a campus called Chemelot in Geleen,
the Netherlands. The staff has next-door
access to hundreds of fermentation, micro-
biology, and analytical experts. At the same
time, we are a small company and act very
quickly, Knoors says. The firm has be-
tween five and 10 new products in the pipe-
line, which Knoors declines to disclose.
Amyris, a publicly traded biobased
chemicals and fuels firm, is close develop-
ment partnerships with the two leading
flavor and fragrance firmsGivaudan and
Firmenichthat provide a competitive ad-
vantage, says Ena Cratsenburg, vice presi-
dent of business development.
According to Cratsenburg, both agree-
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29
ments are for fragrance ingredients and
both have two phases. First is a codevel-
opment phase where the partners work
together to develop a biobased product.
Upon successful development, the part-
ners move to a second, commercialization
phase in which the flavor and fragrance
house would use the ingredient in its own
products, and Amryis would get a share of
the sales value of the ingredient.
BECAUSE OF THEIR SIZE, Givaudan
and Firmenich have incredible demand
all by themselves, Cratsenburg points
out. What makes these two projects so
interesting and powerful for us is not only
do we have a partner working with us on
development of ingredients to ascertain
quality and end-user preferences using
their in-house perfumers, but at comple-
tion they are the ones who will be the big-
gest buyers.
Cratsenburg wont reveal the candidate
ingredients. However, in February, Amyris
executives disclosed to stock analysts that
the firm is working with Firmenich on a
fermentation-derived version of patchouli.
Although patchouli is often associated with
incense, it is also a standard ingredient in
fragrance blends for personal and home
care products. The two main contributors
to the oils fragrance are the terpenes pa-
tchoulol and norpatchoulenol.
In its patent application, Firmenich in-
cludes details about how researchers make
terpenes through microbial fermentation.
Typically a bacterium such as Escherichia
coli, or a yeast such as Saccharomyces
cerevisiae, is engineered for isoprenoid pro-
duction by insertion of one of two genetic
pathways used by plants to make terpene
precursors. The microbe also gets genes
coding for a terpene synthasean enzyme
that makes a particular terpene from one or
more precursors. The resulting terpene can
be functionalized through hydroxylation,
isomerization, oxidation, reduction, or
acylation.
As for the Givaudan partnership,
Cratsenburg says the fragrance starting
material is farnesene, a sesquiterpene that
Amryis makes from fermentation. She says
the target molecule is currently in use and
is derived from petroleum feedstocks. The
fermentation route allows Givaudan to
leapfrog certain steps in chemical produc-
tion, conferring cost and environmental
benefits.
Another of the start-ups, the Swiss
firm Evolva, has identified pathways for
the fermentation production of saffron
components, one of which is the monoter-
pene glycoside picrocrocin. It anticipates
commercial availability in 2015 or 16. In
addition, Evolva has two ongoing flavor in-
gredient collaborations with International
Flavors & Fragrances, the third-largest
company in the industry.
Evolvas work is not limited to terpenes.
Since early 2010 it has been working with
university researchers to construct bio-
synthetic pathways to vanillin. In addition,
it has made key components of the plant-
derived sweetener stevia via fermentation
in yeast.
Large buyers of flavor and fragrance in-
gredients are not choosing partners solely
because of their early product targets, Lux
Researchs Kersh points out. They dont
want to just buy a strainthey want a
deeper partnership with someone who has
the ability to make biocatalysts, he says.
The biotechnology firms have made note of
this need; all are promoting their ability to
develop a full pipeline of any desired mol-
ecules under long-term partnerships.
At Amyris, Cratsenburg says the key word
in the young industry is platform. Our
technology fundamentally takes what ex-
ists in nature, makes it via fermentation in a
sustainable and consistent way, and allows
us to give a flavor and fragrance company a
whole new platform to innovate around.
Today, if a flavor or fragrance house
customer wants to include a plant-derived
ingredient in a consumer product it is lim-
ited to ones that will not be greatly affected
by the vagaries of nature or governments.
But as long as we can put it in our microbi-
al platform and use sugar as feedstock, reli-
ability is not an issue, Cratsenburg says.
That means that patchouli lovers can
look forward to a time when they can find
their favorite woody scent in all sorts of
products, unaffected by drought, mon-
soon, or volcano.
With microbial production, a once-
rare fragrance or flavor could be
made in much larger quantities.
Condence means afrming your
instruments are globally certied
to maintain the strictest food
safety standards. Afrm your
proof-of-system maintenance and
calibration with Agilents Functional
Verication Services. Standardize
maintenance protocols and validate
testing methodology across all your
chromatography systems worldwide.
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STANDARDS
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streamline ISO 17025 documentation/
certication process, visit:
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30
BUSI NESS
AT THE LATEST EDITION of the trade
fair CPhI China, local exhibitors described
China as a country where its becoming
difficult to make money by producing
pharmaceutical ingredients. The enforce-
ment of manufacturing and environmental
standards is squeezing local companies,
but its also opening new opportunities,
particularly for foreign firms.
A stroll through the vast halls of CPhI
China at the Shanghai New International
Expo Centre in Pudong last month was an
opportunity to take the pulse of Chinas
pharmaceutical ingredients
industry. Most of the exhibitors
at CPhI China were Chinese
companies. Attracting 1,700
exhibitors and nearly 30,000
visitors, the Chinese version of
the pharmaceutical trade show
was nearly as big as the flagship
CPhI Worldwide exhibition
that takes place every fall in
Europe.
One thing thats clear is
that small local companies
are under the gun. Smaller
manufacturers are leaving
the industry, said Tyler Tai
Zhuang, a manager of international mar-
keting at HEC Pharm , a large producer of
active pharmaceutical ingredients (APIs)
based in Dongguan, Guangdong province.
Confronted by stricter enforcement of
environmental standards, smaller Chinese
firms can neither afford to build their own
waste-processing facilities nor hire a con-
tractor to take care of the problem, he said.
Production of pharmaceutical ingredi-
ents is still shifting to China from Europe,
where costs remain higher, Zhuang said. But
China is plagued with overcapacity. For
some types of pharmaceutical ingredients,
particularly fermented ones, Chinas total
production capacity is several times higher
than total world demand, Zhuang noted.
Other problems loom as well. It will be
difficult over the next two years for smaller
companies, observed Wastom Wu, chief
executive officer of Synthetics China , a
producer of APIs based in Taixing, Jiangsu
province. The erosion in the value of the
euro against the Chinese yuan has forced
Chinese firms to accept lower prices from
European buyers, he said.
Meanwhile, competition in China has
become fierce among companies focused
on APIs that have been off patent for many
years. To differentiate themselves, the com-
panies must develop ingredients that have
just lost patent protection, he said.
Another challenge, according to Wu,
is that Chinese authorities are
increasingly reluctant to issue
production licenses. Compa-
nies are merging or acquiring
others specifically to obtain
access to existing pharmaceu-
tical ingredient production
licenses, he observed.
Although difficult to clear, all
of these hurdles are ultimately strengthen-
ing the Chinese pharmaceutical ingredi-
ents industry, Wu added. Local firms that
have the financial means are beefing up
their R&D capabilities, he said, and invest-
ing in their manufacturing facilities. Chi-
nese companies used to focus on cost, but
now the focus is on technology, he said.
U.S. glass producer Corning says it is
benefiting from the more difficult busi-
ness environment. Present at CPhI China
to promote the companys flow reactors,
Global Business Director Yi Jiang said the
technology is being received warmly, thanks
to the heightened regulatory environment.
Chinas current five-year plan encourages
more efficient, cleaner production, he said.
This drives technology upgrades.
In addition, Jiang said, Cornings reactors
help companies stand out in the increas-
ingly competitive Chinese marketplace.
Implementing our flow process reactors
can help them demonstrate their ability to
manage complex, high-risk reactions and
secure new contracts.
THE SAME TRENDS that are threatening
Chinese ingredient producers are sources
of opportunity for the Taiwanese pharma-
ceutical ingredients maker ScinoPharm ,
said President Jo Shen.
So far, ScinoPharm does not have cus-
tomers in China, even though the company
recently began production at a new facility
in Changshu, Jiangsu province. Conforming
to developed country standards,
ScinoPharm built the plant to
take advantage of Chinas lower
costs to supply clients elsewhere
in the world, not to gain access to
the local market, she said.
But regulatory changes in
China present an opening for
ScinoPharm in that country,
Shen said. China has adopted
new Good Manufacturing Prac-
tices (GMP) standards that are
far stricter. Chinese companies
will have to invest in upgrades
to meet these standards, and
that will put us on an equal foot-
ing, costwise, in China.
Indeed, the new GMP re-
quirements are so demanding
that some Chinese firms are
opting to buy manufacturing
facilities in Europe in order
to meet them, said Jack H. Ye,
managing director of Hangzhou
Viwa , a producer of pharmaceu-
tical ingredients based in Zhejiang prov-
ince. With the economic crisis in Europe,
we can get a good price on some great as-
sets, he said.
Viwa is investing in an existing facility in
Switzerland that will export oncology drugs
to China. The new Chinese manufacturing
standards are similar to those in the U.S. and
Europe, he said. Quality has become so
important in China that imports are viewed
favorably. JEAN-FRANOIS TREMBLAY
PRESSURE RISES ON
CHINESE DRUG FIRMS
Competition and stricter production standards challenge
Chinas PHARMACEUTICAL CHEMICAL makers
UPGRADING Chinese
generic drug firms
are investing in R&D
to develop new
products faster.
Shown here, the
new kilolab of HEC
Pharm in Dongguan.
J
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Monitoring Requirements
Hazardous substances contaminate the marine environment as a result of human
activities, which impact the sea via direct discharges, through rivers and estuaries,
or from the atmosphere. These contaminants accumulate in shellsh as they lter
the water for food, presenting a toxic hazard when consumed.
The United Kingdom Clean Seas Environmental Monitoring Program (CSEMP)
directly monitors a limited number of hazardous chemicals in coastal and
estuarine areas. The program species 16 organo-chlorine compounds (OCPs),
28 polyaromatic hydrocarbons (PAHs) and 7 polychlorinated biphenyl congeners
(PCBs). The Limit of Detection (LOD) requirements in shellsh are 0.1 g/kg for
OCPs and PCBs, and 0.5 to 1.0 g/kg for PAHs.
The Method
A method for extracting and detecting all 51 of these contaminants in one analysis
and at the required LODs has been developed by scientists at the Centre for
Analytical Research and Development, National Laboratory Service, UK. It uses
QuEChERS and an Agilent 7890 GC coupled to a 7000 Triple Quadrupole GC/MS
system. The chromatographic method includes a post-column pressure controlled
tee which enables post-run backush.
Backushing was used to remove higher boiling substances from the column prior
to each subsequent run. Late eluting peaks are ushed out of the inlet split ow
vent instead of driving them into the mass spectrometer. Accumulated chemical
noise is reduced and the analysis cycle time is shortened, increasing throughput.
System uptime is also increased, due to reduced maintenance of the columns and
MS detector. The suite of Agilent Capillary Flow Technology modules comprises a
proprietary solution that enables easy and rapid backushing with minimal dead
volumes to maintain chromatographic resolution.
The 7890 GC was congured with a carbon dioxide cooled Multimode Inlet (MMI)
and a 15 m X 0.25 mm id, 0.25 m DB-5MSUI capillary column. The 7000 GC/MS
Triple Quadrupole system was operated in electron impact ionization (EI) MS/MS
mode using multiple reaction monitoring (MRM).
Figure 1. TIC MRM chromatograms for a calibration standard of the 51 analytes (lower)
and just the PCB congeners (upper).
DETERMINATION OF CHEMICAL CONTAMINANTS IN MARINE SHELLFISH
USING THE AGILENT 7000 TRIPLE QUADRUPOLE GC/MS
Method Performance
The total ion chromatogram for all MRM transitions of all analytes is shown
in Figure 1. The TIC MRM chromatograms of the PCBs are shown as an inset,
illustrating that the method enables detection of the required analytes .The ve-
point calibration curves using internal standards produced R
2
values >.999 for all
51 analytes.
The recovery values for standards spiked into homogenized mussel tissue were in
the range of 85.4 to 123.9%. Most of the recovery relative standard deviations
(RSDs) were below 10%, with half of them below 5%. Representative recovery
values for the PCBs are shown in Figure 2.
The required analytes can easily be detected at levels below 0.1g/kg, which is
the CSEMP LOD (Figure 3).
This method provides reproducible and sensitive detection of OCPs, PAHs and
PCBs in mussel tissue. For complete details of the method, refer to Agilent
Application Note 5990-7714EN at www.agilent.com.
Figure 2. Graphical representation of PCB percent recovery values.
Figure 3. Upper panel: MRM chromatograms for incurred a-HCH (I) and g-HCH (II) at
0.06 and 0.30 g/kg in mussel tissue. Peaks III and IV are traces of b-HCH and
d-HCH, respectively. Lower panel: MRM chromatograms for incurred PCB 180
at 0.14 g/kg.
1. PCB 28
2. PCB 52
3. PCB 155
4. PCB 101
5. PCB 118
6. PCB 153
7. PCB 138
8. PCB 180
0
5 6 7 8 9
Counts vs acquisition time (min)
10 11 12 13 14 15
1
1
2
2
3
3
4
4
5
5
6
6
7
7
8
8
9
10
2
4
6
8
10
12
105
0
6 8 10 12
Counts vs acquisition time (min)
14 16 18 11.5 11 10.5 9.5 9 8.5 7.5 7 6.5 5.5 5 17 16.5 15.5 15 14.5 13.5 13 12.5 19.5 19 18.5 17.5
1
0.2
0.6
1.4
8.701
(I)
(III)
(II)
(IV)
8.798
8.966
9.078
9.386
9.444
10
2
0
2
4
6
8
13.751
13.833
14.137
PCB 180
14.586
10
32
BUSI NESS
FOR THE SECOND TIME in five years, liq-
uid helium consumers are having trouble
buying the inert and buoyant element. The
situation is dire for some users, and helium
suppliers say it is going to get worse before
it gets better.
Dean Olson, nuclear magnetic reso-
nance lab director in the School of Chemi-
cal Sciences at the University of Illinois,
Urbana-Champaign , says he needs 4,500 L
of helium to cool a new 800-MHz NMR
magnet now sitting unused at the school.
Olson is crossing his fingers that he will
get the helium he needs in September so
users can conduct the analyses of small
molecules, natural products, and
proteins for which the university
bought the $2 million instrument.
Back in 2007, global project
delays and a production outage
at ExxonMobil s helium plant in
Wyoming caused shortages of the
element, which is used to make
items such as semiconductors and
optical fiber and to float weather
and party balloons. Today, a dif-
ferent set of production shortages
and project delays is to blame.
The world is not running out of
helium by any stretch of the imagi-
nation, says Phil Kornbluth, ex-
ecutive vice president of industrial
gas supplier Matheson Tri-Gas , a
subsidiary of Japans Taiyo Nippon
Sanso . Plenty of helium is in the
ground in places such as Qatar, Al-
geria, Iran, and Russia, Kornbluth
says. Getting at it is the problem.
The U.S. Geological Survey es-
timates the size of helium reserves
outside the U.S. at 1.1 trillion cu
ft, whereas U.S. reserves are just
153.2 billion cu ft. But even though
overseas reserves are formidable,
today the U.S. supplies nearly
three-quarters of the more than
6 billion cu ft of helium used annu-
ally worldwide.
Supply interruptions, some in the U.S.
and some overseas, have conspired to
cause the current helium shortage, says
John K. Van Sloun, helium general manager
for Air Products & Chemicals , which claims
to be the leading supplier of
the element. Other suppliers
include Praxair , Air Liquide ,
and Linde .
In the Texas Panhandle
and extending into Oklahoma
and Kansas, the U.S. govern-
ment helium pipeline and
storage facilitieswhich
mete out about 30% of global
supplywere scheduled to shut down for
about two weeks of maintenance on July 15.
Natural gas firms along the pipeline inject
crude helium, which they cryogenically
separate from natural gas. Refiners such
as Air Products withdraw and process the
helium to a 99% pure liquid.
To the north, ExxonMobils helium
plant in La Barge, Wyo., which accounts
for about 20% of global helium supply,
is undergoing maintenance from June
through August. ExxonMobil says it will
meet its contractual supply obligation.
But industrial gas suppliers say the Wyo-
ming facility wont run at full capacity
during the maintenance period, putting
pressure on supply.
Two helium plants in Alge-
ria run by the national oil firm
Sonatrach have recently been
operating at about half of their
normal capacity because of low
natural gas demand, says Air Prod-
ucts Van Sloun. When demand for
gas from helium-containing wells
goes down, or wells deplete, less
helium is available. Production
shortfalls from small plants in Rus-
sia, Poland, and Australia have also
limited global helium supply, Van
Sloun points out.
SOME RELIEF will come starting
later this year when nearly 2 bil-
lion cu ft of capacity fires up. A
200 million-cu-ft-per-year plant in
Big Piney, Wyo., originally planned
to open in 2011, should begin op-
erating by the end of 2012. Owned
by Air Products and Matheson Tri-
Gas, the plant sits idle while the
projects crude helium supplier,
Cimarex Energy , completes work
on its own facility.
Sometime next year, an expan-
sion in Algeria will add 350 million
cu ft of capacity, industrial gas
suppliers say. But the biggest ad-
dition of them all is the 1.3 billion-
cu-ft Qatar Helium 2 project,
scheduled to open in early 2013
by the Qatari firm RasGas . To-
gether with the 660 million-cu-ft
Qatar Helium 1 plant already in
operation, RasGas says, the new
capacity will make the country
the worlds second-largest helium
producer.
And Russia could also enter the
major leagues of producers. In
HELIUM SUPPLIES
ARE SCANT, AGAIN
Global PRODUCTION SHORTFALL means the
element will be scarce into 2013
MARC S. REISCH , C&EN NORTHEAST NEWS BUREAU
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SITTING IDLY BY
Scientists at the
University of Illinois,
Urbana-Champaign,
are unable to cool
down this 800-MHz
NMR magnet, which
arrived in late June,
until they locate
4,500 L of helium.
33
I spend $30,000 per year on helium
that is just blowing out of the roof.
2014 or sometime thereafter, large new he-
lium reserves are likely to be tapped in Si-
beria, says Peter J. Madrid, a helium analyst
with the U.S. Bureau of Land Management
(BLM), which manages the governments
pipeline.
The capacity additions should fix mat-
ters in the long run, but right now, the Uni-
versity of Illinois Olson is worried about
getting enough helium to fill his new NMR
machine and maintain the 10 NMR instru-
ments now being used by 350 researchers
at the school. He recently learned that he
wont get his full allocation for July.
Olson is considering the installation of
an elaborate system, at a cost of $40,000,
to capture and recycle helium that bleeds
off his instruments. I spend $30,000 per
year on helium that is just blowing out of
the roof, he says.
In a way, Olson is lucky. The $40,000 he
would spend on a capture system doesnt
include purification and refrigeration equip-
ment. For that he can tap into a recycling
facility housed in the universitys physics
department, which uses helium in atomic
structure characterization experiments.
Benjamin Kohn, a research associate in
the department of chemical and biological
engineering at Colorado State University,
Fort Collins , isnt so lucky. He says he isnt
sure his department can afford the high
cost of recycling helium from its eight
NMR instruments. In addition, the depart-
ments instruments are not centralized,
making helium capture difficult.
UNTIL RECENTLY, the low cost of helium
meant that recycling wasnt a consider-
ation, Kohn says. But the universitys heli-
um costs have climbed from $5.00 per L in
2008 to $15 today, making recycling worth
considering. Other U.S. researchers report
that they are now paying up to $34 per L.
Heliums retail price, Air Products Van
Sloun explains, is benchmarked to the
price BLM charges for helium. That price
rose 16% in October 2009, 1% in 2011, and
is scheduled to increase another 11% later
this year. Industrial gas firms are charg-
ing users more for helium to recover their
higher costs, Van Sloun says.
Large users have installed recycling
equipment to keep a lid on helium costs.
Optical fiber maker Corning says it cap-
tures and recycles helium used in its plants.
The Royal Philips Electronics plant in
Latham, N.Y., had Air Products install a
capture, liquefaction, and reuse system for
helium needed to fill new magnetic reso-
nance equipment for medical imaging.
Air Products sales of new helium to the
Philips facility dropped 40% as a result, Van
Sloun says. Philips was delighted to see its
costs go down, and other users are eager to
buy the helium freed up by the New York
plant, he says.
Alternatives to helium-recycling sys-
34
BUSI NESS
tems for NMR users are either instru-
ments with built-in capture and re-
cycling capabilities or ones that rely
on rare-earth permanent magnets
instead of helium-dependent super-
conducting magnets.
Recondensing systems, at an ad-
ditional cost up to $150,000, seal an
NMR magnet in a liquid helium bath.
A closed-loop refrigeration system
keeps the helium at a stable low tem-
perature without the need for refills,
says Michael Cuthbert, business
group manager for Oxford Instru-
ments , a maker of the systems.
Italian NMR producer Aspect
Italia, a unit of NMR and MRI maker
Aspect AI of Israel, is one firm that
makes an instrument with a perma-
nent rare-earth magnet that does
not require helium. Paul J. Giammatteo,
an owner of Process NMR Associates , the
firms U.S. distributor, says the AI-60, a
60-MHz bench-height NMR system in-
troduced earlier this year, has no magnet-
cooling requirements whatsoever.
The $85,000 AI-60 can in some cases
substitute for other highly sensitive NMRs.
However, for very small samples, more
sensitive helium-cooled instruments
at 600 MHz or higher are preferred, he
acknowledges.
In the midst of the helium shortage,
U.S. users of the gas must contend with
a long-term decline in helium pro-
duction from domestic natural gas
wells and the possibility that the
U.S. governments pipeline and he-
lium storage facility could be shut
down.
The government built up its
helium stocks over decades, con-
sidering them strategic reserves
for military use. In 1996, under the
Helium Privatization Act, Congress
authorized the sale of the govern-
ments 30 billion cu ft of helium by
2015, except for a permanent reserve
of 600 million cu ft. A bill now before
Congress, the Helium Stewardship
Act, would keep the government he-
lium system open longer.
Regardless of legislation, industry
executives point out, the govern-
ment reserves are depleting and are likely
to last for only another decade or so. Still,
thats enough time for other producers
to bring on new helium resources. Yes,
helium is scarce now, BLM analyst Madrid
says, but in five years the supply situation
could be good through 2030.
U.S. consumption in 2011 = 2 billion cu ft
MRI
22%
Semiconductors &
ber optics
18%
Leak detection
4%
Welding
13%
Space launch vehicles
18%
Breathing
mixtures
2%
NMR & other
superconductors
10%
Other
a
13%
a Includes weather balloons, blimps, party balloons, and gas chro-
matography. MRI = magnetic resonance imaging. NMR = nuclear
magnetic resonance.
SOURCES: U.S. Geological Survey, IHS Chemical
BUOYANT MARKETS Magnetic resonance
imaging is the largest single use for helium.
Working at-line in the Food and Feed Industries requires a robust yet accurate instrument, that
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408,307 CITATIONS
The Most Cited Journal
in Chemistry

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ARTICLES
PUBLISHED
The most cited journal in chemistry, the Journal of the American Chemical Society received 408,307 total
citations and posted an increase in Impact Factor to 9.907 as reported in the 2011 Journal Citation Reports
from Thomson Reuters.
IMPACT
FACTOR
PETER
J. STANG
EDITOR
23%
MULTIDISCIPLINARY
CHEMISTRY
#
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GOVERNMENT & POLI CY CONCENTRATES
CANADA AND MEXICO JOIN
PACIFIC RIM TRADE TALKS
U.S. trade officials notified Congress last week that Canada and Mexico
are joining the Trans-Pacific Partnership (TPP), a proposed free-trade
agreement the Obama Administration has been negotiating for the past
three years. Along with the U.S., the talks involve Australia, Brunei, Chile,
Malaysia, New Zealand, Peru, Singapore, and Vietnam. The American
Chemistry Council, a chemical industry trade group, says it welcomes the
pacts expansion. The inclusion of Mexico and Canada to the Pacific free-
trade talks will enable U.S. businesses to advance existing commercial
relationships with our North American trading partners, while at the same
time broadening the scope and impact of the negotiations, ACC says. TPP
seeks to form a free-trade bloc spanning the Pacific Ocean by removing
tariffs and other trade barriers while strengthening measures to protect
intellectual property rights. Negotiators concluded a round of talks in San
Diego on July 10 and plan to meet again in September in Leesburg, Va.
Trade policy analysts expect the talks to wrap up next year. GH
VIDEO PROMOTES USE
OF SAFER DESIGN
In a safety video released last week, the
Chemical Safety & Hazard Investigation
Board (CSB) urges chemical companies
to examineand apply when possible
inherently safer design principles when
making production decisions. The video
identifies and underscores four principles
of inherently safer design that CSB says
companies should use. They are: replacing
a hazardous chemical with a less hazardous
one, minimizing use of hazardous materi-
als, moderating a manufacturing process
to reduce the likelihood and impact of an
accident, and simplifying a manufacturing
process so it is less prone to failure. The
video and CSB recommendations sprang
from a recent National Academy of Sci-
ences investigation and report that consid-
ered how the chemical industry could pro-
mote safety by improving process design
techniques. That investigation examined
a 2008 accident at the Bayer CropScience
plant near Charleston, W.Va., which killed
two workers and almost caused the release
of 13,000 lb of methyl isocyanate stored at
the plant (C&EN, May 21, page 5). JJ UNIVERSITIES WARN OF
BLUNT BUDGET CUTS
President Barack Obama and Congress
should act soon to prevent indiscriminate
federal budget cuts scheduled for January
2013 or risk damage to the countrys educa-
tion system and scientific research, says a
letter from 152 university chancellors and
presidents . More than $1 trillion in manda-
tory budget cuts, called sequestration, were
enacted when a bipartisan congressional
panel failed to come to a budget agreement
last November. Sequestration is an undis-
cerning and blunt budget tool that would
substantially harm our nations future by
blindly slashing valuable investments,
says the letter from university leaders in
50 states and the District of Columbia.
Instead, politicians need to find a deficit
reduction strategy that includes tax reform
and cuts to entitlement programs such
as Medicaid and Social Security rather
than cutting 810% from discretionary
programs, the year-to-year funding that
includes almost all science and education
funding. Americans know that invest-
ments in education and scientific research
pay long-term dividends, the letter says.
We urge you to show America and the
world that our countrys political system is
capable of solving serious problems. AW
EPA REVIEWING
NANOSILVER PESTICIDES
EPA wants to reclassify a handful of pesti-
cides already on the market as containing
nanosilver. Most of the manufacturers
of these products registered them with
EPA without disclosing that they contain
nanosilver, even though they have silver
particles with dimensions between 1 and
100 nm. To address the potential health and
safety effects of silver in the products, the
companies had submitted data for conven-
tional silver or silver chloride. The agency
now proposes requiring companies to sup-
ply additional data about the products so
EPA can determine whether nanosilvers
unique physical and chemical properties al-
ter the health and safety properties of these
products, compared with conventional
silver products. The agency plans to focus
initially on what form and concentration of
silver is released from the products. If the
agency determines that nanosilver is re-
leased, it will then ask companies for data on
SHALE FORMATIONS
CONNECTED TO AQUIFERS
Pathways exist that would allow migration
of methane, brines, or fracturing fluids
from deep Marcellus Shale gas formations
to shallow drinking water aquifers, ac-
cording to a new study ( Proc. Natl. Acad.
Sci. USA, DOI: 10.1073/pnas.1121181109 ).
Geologists at Duke University and Cali-
fornia State Polytechnic University, Po-
mona, examined geochemical evidence in
northeastern Pennsylvania. They found
that migration of naturally
occurring Marcellus brines
and other materials has
taken place through natural
hydraulic connections be-
tween 1-mile-deep geologi-
cal formations and shallow
aquifers. These pathways
predate the current shale
fracturing activities occur-
ring in the area, the study
notes. The study examined
GOVERNMENT & POLI CY CONCENTRATES
Communities fear that
drilling for shale gas will
contaminate drinking water.
M
L
A
D
E
N

A
N
T
O
N
O
V
/
A
F
P
/
G
E
T
T
Y

I
M
A
G
E
S
/
N
E
W
S
C
O
M
health and ecological effects, as well as envi-
ronmental fate. EPA is accepting comments
on the proposed process until Aug. 19. BEE
three aquifers and analyzed 426 groundwa-
ter samples and 83 deep-formation brine
samples. The researchers found com-
pounds from the brine in the groundwater.
They noted the increasing concern of com-
munities in the region over contamination
of drinking water from natural gas explora-
tion in the area, but the study did not dem-
onstrate that methane or drilling fluids are
in aquifers. JJ
37
GOVERNMENT & POLI CY
THE LONG-TERM FUTURE of coal in the
U.S. may rest with the success of a hand-
ful of demonstration projects that will
attempt to capture emissions of carbon
dioxide, a greenhouse gas, from coal-fired
power plants. At present, carbon capture
and sequestration (CCS) is the most likely
route to reducing the contribution of coal-
fired power plants to climate change.
Yet CCSs future looks bleak. To protect
coal and coal jobs, coal-related industries
and coal-state politicians have fought hard
and have successfully blocked climate
legislation, but in doing so, they have killed
the primary reason for developing CCS
technology.
The demonstration projects are the first
to move past small pilot projects and apply
bench-scale technologies to full-scale plant
operations. With funding from industry
and the Department of Energy, the eight
projects are intended to apply CCS tech-
nologies at three industrial facilities and
five electric power plants. The smaller, less
expensive industrial projects are progress-
ing. The bigger power plant projects are
just getting under way; the farthest along is
only about half complete.
Technology developers have had dif-
ficulty obtaining financing and justifying
spending the billions of dollars needed to
scale up these so-called clean-coal tech-
nologies. According to officials from DOE,
industry, and energy think tanks, CCS
developers face a complex problem. In ad-
dition to the normal and expected hurdles
that are part of the development of any
new technology, CCS promoters have been
hit by a perfect storm in todays political
and economic climate: a high financial wall
without any economic or regulatory driver
to encourage investments in expensive
pollution cleanup technologies.
What a difference a few years makes,
says Pamela Tomski, senior fellow in the
energy program of the Atlantic Council , a
Washington, D.C., think tank.
The high point for legislative action on
climate change, Tomski points out, came
in 2009. That year, the House of Represen-
tatives cleared legislation to require CO
2
reductions and a cap-and-trade program
that would have put a cost on carbon emis-
sions. Despite passing by a razor-thin,
seven-vote margin, the bill signaled hope
for a low-carbon future, she says ( C&EN,
July 6, 2009, page 8 ).
Just a year later, a watered-down version
of the bill died on the Senate floor. With
its demise, the primary drivers for CCSa
price on carbon
emissions and
a CO
2
-trading
schemealso
expired.
Today, a ma-
jority of Con-
gress members
have no inter-
est in putting
a price on car-
bon. In addition, many members even chal-
lenge the scientific basis of climate change.
Although no price has been set on carbon,
CCS research has been getting some sup-
port because of global warming. DOE has
set a goal of having commercially viable CCS
technology by 2020, notes a recent report
by the nonpartisan Congressional Budget
Office. To meet this target, according to the
report, DOE has provided some $6.9 bil-
lion in R&D funding since 2005. Half of that
total came from the American Recovery &
Reinvestment Act of 2009, President Barack
Obamas stimulus package.
The R&D funding alone has proven inad-
equate to make CCS application economi-
cally viable, CBO states. It estimates that
electricity from power plants using CCS
would be 75% more expensive than elec-
tricity from conventional coal-fired power
plants because of the cost of new equip-
ment, primarily devices to capture CO
2
.
To lower those costs, the report warns,
CCS technologies must be demonstrated at
hundreds of commercial-scale coal power
plants to ensure they can economically
capture CO
2
, compress it, pipe it, inject it,
and permanently keep it deep underground
and out of the atmosphere.
Similarly, recent studies by the Congres-
sional Research Service and the World-
watch Institute find a great need for CCS
but little follow-through for expansion
of demonstration projects at commercial
plants.
WITHOUT TECHNOLOGY such as CCS to
reduce coals CO
2
emissions , coal is likely
to find it increasingly difficult to compete
in a greenhouse-gas-constrained world
against electricity generators that do less
climate damage, such as natural gas, re-
newable energy sources, or nuclear power.
Coal currently plays a huge role in the na-
tions power mix, but its share of the market
is sliding. In 2011, coal generated 39% of U.S.
electricity, making it the largest source of
electricity. But in 2010, it accounted for 47%
of U.S. electricity. The drop is due to gains
STUMBLING ON THE
PATH TO CLEAN COAL
CARBON CAPTURE AND SEQUESTRATION appears stuck,
dashing hopes of cutting CO
2
while burning coal
JEFF JOHNSON , C&EN WASHINGTON
M
I
S
S
I
S
S
I
P
P
I

P
O
W
E
R
ONE OF FEW When a
CCS system being built
by Mississippi Power/
Southern Co. at this
power plant is completed,
emissions from the
coal-based electricity
generator would match
those from a natural-gas-
based power plant.
38
GOVERNMENT & POLI CY
in electricity-generating efficiency, a de-
cline in the U.S. economy, and the growth of
electricity generation from natural gas.
Gass share jumped from 22% in 2010 to
26% in 2011. With record levels of produc-
tion and plummeting prices of natural gas,
that growth is expected to continue. Latest
figures from DOEs Energy Information
Administration (EIA) show that natural gas
accounted for 28.7% of U.S. electricity dur-
ing the first quarter of 2012, compared with
20.7% from the same quarter last year.
In contrast, coals share of U.S. electric-
ity generation in the first quarter declined
from 44.6% in 2011 to 36.0% this year.
However, coal retains its leadership in
greenhouse gas emissions: It is responsible
for about one-third of the U.S.s anthropo-
genic CO
2
emissions and 80% of CO
2
emis-
sions from the electricity sector, according
to EIA.
GOVERNMENT POLICIES to cut CO
2
emissions from coal-fired power plants
and allow the continued use of coal have
proven impossible to implement. There
is a conflict in the U.S., says Robert Hil-
ton, vice president of power technologies
for government affairs at Alstom, a global
construction and engineering firm. While
there is strong support for coal, there is no
driver for CCS.
According to Hilton, a financial and
regulatory impasse killed Alstoms CCS
efforts in the U.S. Instead, Hilton says,
Alstom is focusing on two new projects
in China and is a lead participant in a new
CCS demonstration facility in Norway. At
Alstom, we have begun talking about the
U.S. piggybacking on projects being done
in the rest of the world.
With frustration in his voice, Hilton de-
scribes what happened at Alstoms biggest
U.S. project: Last July, the Midwestern util-
ity American Electric Power (AEP) termi-
nated a project to construct a commercial-
scale advanced CCS technology add-on to
its 1,300-MW Mountaineer Power Plant in
West Virginia. Alstom would have built the
CCS system, which would have been the
worlds largest at a coal-fired power plant.
AEPs goal was to capture 90%, or
1.5 million metric tons, of the CO
2
from the
exhaust stream from 235 MW of the plants
capacity by 2015. After two years of plan-
ning and construction of a $100 million
pilot facility at the site, AEP canceled the
project. AEP also rejected a $334 million of-
fer from DOE to aid the project, which the
company would have had to match.
We are in a classic which comes first
situation, said AEP Chairman Michael G.
Morris at the time, adding that there was
no viable path forward. Thats because to
recover its construction costs, AEP would
need approval from its public utility com-
mission. As a regulated utility, Morris ex-
plained, it is impossible to gain approval
to recover our share of the costs for the
technology without federal requirements
to reduce greenhouse gas emissions.
The regulatory uncertainty, he added,
also made it difficult to attract financial
partners to help fund the industrys share
of the construction project. It died from a
combination of U.S. climate policy confus-
tion coupled with a weak economy, accord-
ing to AEP.
The rates we charge customers are set
by public utility commissioners, notes Pat
D. Hemlepp, AEPs director of corporate
media relations. The commissioners said
this was an excellent project, but AEP is not
required to do it. So they are not going to au-
thorize cost recovery. It is a valid position.
It is difficult to show any justification for
carbon capture when Congress has taken
no action and has not indicated that any
action would take place, period, Hemlepp
continues. A utility would be very reluctant
to build a new power plant with CCS. There
is no known technology that can do it and no
idea of what will be required in the future.
To avoid the unknowns associated with
coal, the push will be toward natural gas
for electricity production, Hemlepp says.
The price of natural gas has fallen to record
lows in the U.S., he notes, adding that gas
produces 40% less CO
2
than coal. Reliance
on natural-gas-fired power plants, Hilton
notes, will only slow the growth of CO
2
emissions, not eliminate them. Depen-
dence on gas will also continue coals de-
clining share of the electricity market.
To fight climate change, the Environ-
mental Protection Agency last March
proposed a new rule that will further make
life tough for coal, Hemlepp and Hilton
point out. The proposal would limit CO
2
emissions from all fossil-fuel-based power
plants to 1,000 lb per MWh of electricity
generation. That level is about what a mod-
ern, well-run, natural-gas-fired power plant
would emit using advanced technologies,
PILOT PROJECTS
Eight major U.S. carbon capture and sequestration demonstration projects are under way
INVESTMENT ($ MILLIONS)
PROJECT DEVELOPER WHERE CCS WILL BE USED LOCATION
START-UP
TARGET DOE TOTAL
Air Products & Chemicals
Industrial power and chemical production at
Valero renery Port Arthur, Texas 2013 $284 $431
Archer Daniels Midland
Industrial power and chemical production at
biofuel plant Decatur, Ill. 2013 141 208
FutureGen 2.0
Modifying an existing 200-MW coal-red
power plant Meredosia, Ill. 2017 1,000 1,300
HECA (Hydrogen Energy California) New 250-MW gasication power plant Kern County, Calif. 2017 408 3,900
Leucadia Energy
New gasication plant for industrial power
and chemical production Lake Charles, La. 2015 261 436
Mississippi Power/Southern Co. New 582-MW gasication power plant Kemper County, Miss. 2014 270 2,010
Summit Powers Texas Clean
Energy Project
New 400-MW gasication power plant Ector County, Texas 2015 450 1,727
NRG Energys WA Parish
240-MW demonstration project at existing
3.65-MW power plant Houston area na 49%
a
na
a Total investment amount not available; DOE plans to fund percentage shown. CCS = carbon capture and sequestration. DOE = Department of Energy. na = not available.
SOURCE: DOE
39
but without CCS ( C&EN, April 2, page 6 ).
Hilton estimates that new state-of-the-
art coal-fired power plants would emit
around 1,650 to 1,750 lb of CO
2
per MWh.
Older ones would emit 2,300 lb per MWh
or more. To meet EPAs proposed emis-
sions level, he notes, all coal-fired power
plantseven new oneswould have to use
CCS technology.
EPAs proposal would not cover existing
plants and would put off implementation
for a year, giving plants in planning a chance
to begin construction before the regulation
hits, EPA officials said when issuing the
proposal. However, the announcement also
makes clear that EPA intends to eventually
regulate CO
2
emissions. Hemlepp doubts
companies will try to build new coal-fired
plants without knowing what regulations
they must comply with .
One new avenue CCS advocates are ex-
ploring to drive the adoption of CCS tech-
nologies is the possibility of selling CO
2
captured from coal-fired power plants to
oil companies. The gas is used in enhanced
oil recovery, an application that is growing.
Enhanced oil recovery involves inject-
ing CO
2
into partially depleted oil fields to
drive crude oil to the surface. The opera-
tion can double the output of oil fields.
Most CO
2
now used for enhanced oil
recovery comes from natural or industrial
sources, and coal advocates would like to
see the CO
2
come from CCS.
OF DOES EIGHT CCS projects, six hope to
sell captured CO
2
to oil producers. Among
power plants, farthest along is a 580-MW
facility in Kemper County, Miss., owned
by Mississippi Power/Southern Co. A CCS
system would capture about 3 million met-
ric tons of CO
2
annually, about two-thirds
of the power plants CO
2
waste stream. It
aims for a 2014 start-up date.
The second farthest-along power plant
is a 400-MW plant of Summit Powers
Texas Clean Energy Project, in Ector
County, Texas. Along with electricity, this
power plant will produce ammonia and is
expected to generate about 3 million met-
ric tons of CO
2
annually when operation
begins in 2015 .
Projects like these are a bridge for
CCS development, says Robert J. Wright,
a senior adviser in DOEs Office of Fossil
Energy. We dont see a price on carbon in
the next four or more years, and we dont
see another recovery act stimulus package
coming along to provide funding.
Wright and Tomski hope growing de-
mand from oil interests may help support
the cost of developing CCS projects. Both
note many unknowns to be explored: How
will the injected CO
2
be regulated? Will CO
2
permanently stay underground? Who will
be liable for leakage or earth tremors during
injection? How much will all this cost?
Wright also notes that the oil industry
doesnt want to permanently store the CO
2
it buys for enhanced-recovery operations.
The industry bought it and will want to use
it and reuse it at oil fields. In this scenario,
the final resting place of the CO
2
is unclear.
Tomski and others doubt that the eco-
nomic gain from enhanced oil recovery
will cover the entire costs of capture tech-
nologies, nor will the storage capacity be
enough to handle the volume of CO
2
emis-
sions from all coal-generated CO
2
forever.
In the absence of carbon legislation,
this is the best weve got, she says.
Dont miss the Virtual Issue from The Journal of
Organic Chemistry, Organic Letters, and the Journal
of the American Chemical Societyillustrating what
can be done in cross-coupling chemistry, where the
limits are and where future studies are heading.
pubs.acs.org/r/crosscoupling
View the complete issue at
VI R T UAL S P E CI AL I S S UE >>> CROS S - COUP L I NG
40
SCI ENCE & TECHNOLOGY CONCENTRATES
MATERIALS WITH SMARTS
Windows might one day become more energy efficient with help from
a self-regulating thermal coating, according to a report in Nature (DOI:
10.1038/nature11223). Joanna Aizenberg of Harvard University, Anna C.
Balazs of the University of Pittsburgh, and colleagues developed polymer-
based materials
that maintain
their internal
temperature
within a 1.7 C
range regardless
of surround-
ing conditions.
Called SMARTS,
for self-regulated
mechanochemi-
cal adaptively
reconfigurable
tunable system,
the coatings are
composed of
catalyst-tipped
microposts em-
bedded in a tem-
perature-respon-
sive poly(N-iso-
propylacrylamide) hydrogel. A thin liquid layer containing chemical reagents
rests atop the gel. Like hairs on a persons arm, the tiny posts stand up at
low temperature as the hydrogel absorbs water and swells. The catalyst on
the post tips then reacts exothermally with compounds in the reagent layer,
causing the gel to heat and contract. When that happens, the posts flop
over, moving out of reach of the reagent layer. Thereafter, the cycle repeats
as the chemical reaction switches on and off in a feedback loop. Besides
being useful to control weather-responsive building materials, the patented
SMARTS might also be incorporated into biochemical sensors, robotics,
and medical implants, Aizenberg says. LKW
SPINTRONIC
OLED DEBUTS
An organic light-emitting diode (OLED)
whose intensity is mediated by electron
spin rather than purely by electronic
charge may usher in a new breed of organic
displays that are cheaper, brighter, and
controlled by magnetic fields (Science, DOI:
10.1126/science.1223444). Z. Valy Vardeny
of the University of Utah and colleagues
based their spintronic device, which emits
orange light, on their previous develop-
ment of an organic spin-valve, a switch
that regulates current on the basis of the up
or down alignment of electron spin. Sever-
al augmentations to the original spin-valve
design, including a deuterated derivative of
poly(phenylene vinylene) and a thin layer
of lithium fluoride on a cobalt electrode,
make it possible to inject both negatively
charged electrons and positively charged
electron holes into the device, rather
than only electrons. The collisions of the
oppositely charged particles then gener-
ate photons. An external magnetic field,
which aligns the spins of the electrons and
electron holes, adjusts the intensity of the
light. With further research, Vardeny envi-
sions the development of spin-OLEDs that
change colors. EKW
MEMBRANE PROTEINS
CAUGHT ON CAMERA
Using high-speed atomic force micros-
copy (AFM), an international team of
researchers has captured on film the
motions and interactions of membrane
proteins (Nat. Nanotechnol., DOI: 10.1038/
nnano.2012.109). Scientists have used
fluorescence microscopy to examine the
dynamics of membrane proteins before,
says team leader Simon Scheuring of the
French National Institute of Health &
Medical Research. But those experiments
required that the protein be fluorescently
labeled, he says. They also typically fol-
lowed the motion of only one protein at a
time. Scheurings team sees all the proteins
in the membrane with AFM, he notes, and
therefore learns how the diffusion of a pro-
tein is affected by its molecular environ-
ment. To make the AFM measurements,
Scheuring and colleagues deposited the
Escherichia coli membrane protein OmpF,
along with some E. coli lipids, onto a mica
support. The researchers found that OmpF
proteins move slowly over short distances
ANTIBIOTIC TAKES AIM
AT MEMBRANE TARGETS
Standard antibiotics are usually fine for
fighting most fast-growing bacteria, but
they typically have trouble treating persis-
tent infections caused by slow-growing dor-
when in crowded areas and wander at a
faster pace over longer distances in loosely
packed regions. Combining AFM data with
molecular dynamics simulations, they also
generated a potential energy map of pro-
tein-protein interactions. Developing tech-
niques that assess how proteins play with
each other, Scheuring points out, is vital to
understanding cellular function. LKW
DOING THE WAVE In SMARTS, a hydrogel responds to
a temperature change by swelling (right) or shrinking (left),
forcing microposts to stand up and react with reagents
(microscope image, bottom right) or op over (bottom left).
A
D
A
P
T
E
D

F
R
O
M

N
A
T
U
R
E
High temperature
Reagents
Temperature-
responsive hydrogel
Microposts
Catalyst H
2
O
Products + Heat
Low temperature
10 m
DCAP
OH
OH
OH
OH
Cl
Cl
N
H
N
mant and biofilm-associated bacteria. Now,
researchers led by Douglas B. Weibel of the
University of Wisconsin, Madison, have
discovered a broad-spectrum antibiotic
capable of killing these types of bacteria
(J. Am. Chem. Soc., DOI: 10.1021/ja302542j).
The compound, known as DCAP, battles
the slow growers by reducing their trans-
membrane potential and increas-
ing their membrane
permeability.
These processes
disrupt the orga-
nization and in-
tegrity of the bacterial
membrane and put essen-
tial membrane-associated
proteins out of whack. Wei-
41
FOUR-SQUARE NITROGEN
Australian chemists have spotted what
they say is the first definitive example of a
tetrazetidine, a molecule containing an un-
precedented four-membered nitrogen ring
(J. Am. Chem. Soc., DOI: 10.1021/ja303019y).
The tetrazetidine system is one of the
SEQUENCING METHOD
CORRECTLY MAPS
DNA HAPLOTYPES
A new DNA-sequencing method allows
researchers to efficiently determine haplo-
typessequence variants that are usually
inherited togetherusing an amount of
DNA equivalent to the amount from only
10 to 20 cells. The method was developed
by a team led by Brock A. Peters and Radoje
Drmanac of Complete Genomics, a Moun-
tain View, Calif., sequencing firm (Nature,
DOI: 10.1038/nature11236). The ability to
determine haplotypes is clinically impor-
tant for identifying whether mutations
occur in one or both copies of a gene. In
Complete Genomics long fragment read
approach, about 100 pg of 100-kilobase
DNA is physically separated into 384 pools,
with each pool containing 10 to 20% of one
copy of the genome. The DNA is amplified,
fragmented, and labeled with a DNA bar
code that identifies the well. The fragments
are then combined, amplified again (includ-
ing the bar codes), and then sequenced. The
bar codes allow sequences to be mapped
back to the original fragment they came
from. To test the method, the researchers
determined haplotypes of samples from the
International HapMap Project and found
that they were able to accurately assign up
to 97% of single-nucleotide polymorphisms
to correct haplotypes. The error rate was
1 in 10 megabases, they report. CHA
SILK FILM ACTS AS
VACCINE PRESERVATIVE
Researchers at Tufts University report
that silk can keep vaccines from degrading
without refrigeration (Proc. Natl. Acad. Sci.
USA, DOI: 10.1073/pnas.1206210109). The
finding could help vaccine treatments
reach more people in the developing
world, where refrigeration is scarce and
vaccines often heat up and lose potency
before they can be administered. David
L. Kaplan and colleagues dissolved silk
protein in a salt solution; mixed it with
measles, mumps, and rubella vaccine; and
then dried the mixture into films. In the
silk film, the vaccine was effective for more
than six months at temperatures of up to
45 C, whereas the dried vaccine alone lost
nearly all potency. The researchers pro-
pose that silk protein traps the vaccines vi-
ral particles in spaces between its -sheets,
holding the viral proteins in their native,
folded state and preventing denaturation.
Silks structure also excludes some water,
enhancing its preservative qualities. The
low toxicity and price of silk make it a good
candidate for application, says Randolph
V. Lewis, a silk protein expert at Utah State
SIMULATIONS PEG
PROTEIN FOLDING
Data from theoretical simulations of the
folding of green fluorescent protein (GFP)
agree well with previous experimental re-
sults on the thermodynamics and kinetics
of the proteins folding (Proc. Natl. Acad. Sci.
USA, DOI: 10.1073/pnas.1201808109).
GFP is widely used as a fluorescent
marker in molecular biology stud-
ies, so the new results could aid the
design of modified forms of GFPs
for a range of applications. De-
varajan (Dave) Thirumalai of the
University of Maryland notes that his
teams molecular dynamics simulations
of GFPs folding pathways are the first to
replicate experimental thermodynamic and
kinetic data on such a large protein. GFP
has about 240 amino acid residues, whereas
similar molecular dynamics simulations
had been done only for proteins with
fewer than 100
residues, he says.
Thirumalai and
coworkers used a
technique called
the Molecular
Transfer Model
to simulate
denaturant-induced GFP folding. The data
confirm experimental findings showing
that GFP folds initially to an ensemble of
intermediate states, which then take one of
four possible pathways to reach GFPs na-
tive conformation. SB
University. It has huge potential in the hu-
man health area, he says. DL
Simulated
folding routes along a
3-D energy coordinate
indicate how GFP
intermediates reach
the proteins natively
folded structure
(bottom right).
Silk protein entraps vaccine
components, protecting them
from denaturation.
P
R
O
C
.

N
A
T
L
.

A
C
A
D
.

S
C
I
.

U
S
A
H
OH
bel and coworkers identified DCAP by high-
throughput screening. The compound has
no toxic effect on red blood cell membranes
at concentrations at which its effective
against bacteria, the researchers note, but
they did observe some toxicity in studies
with other types of human cells. They plan
to address this problem by making DCAP
analogs. The researchers also hope that,
by studying DCAPs structure-function
relationship, they can develop design rules
for potent membrane-targeting drugs that
specifically attack bacterial cells. BH
Tetrazetidine
+
N
N N
N
O
O
O
O
O
O
O
O
few simple chemical structures
that has not yet been synthesized
with any certainty. Over the past 20 years,
David Camp and Ian D. Jenkins of Griffith
University and Graeme R. Hanson of the
University of Queensland have used elec-
tron paramagnetic resonance spectroscopy
to study the formation of radicals when
triphenylphosphine and diisopropyl azo-
dicarboxylate are combined in the Mitsu-
nobu reaction. In addition to a phosphine-
azodicarboxylate radical, they sometimes
noticed a second persistent radical with
what they describe as a rather beautiful,
almost symmetrical nine-line spectrum.
Now, in conjunction with Griffiths Marc
Campitelli, and using more
advanced and affordable
computational methods,
the researchers believe
the tetrazetidinetetracar-
boxylate radical cation
shown is being formed by
a Michael-type addition of a
phosphine-azodicarboxylate
radical to a diisopropyl azodicarbox-
ylate molecule. The tetrazetidine radical is
surprisingly long-lived, they note, lasting
several hours at room temperature. SR
VIDEO ONLINE
P
R
O
C
.

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L
.

A
C
A
D
.

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I
.

U
S
A
42
SCI ENCE & TECHNOLOGY
FOR JIFENG ZHANG, research adviser for
bioproduct pharmaceutical development
at Eli Lilly & Co. , the solvation of ions in
water has decidedly practical implications.
The topic may appear arcane and aca-
demic, yet the behavior of aqueous ions has
profound effects on biological molecules
such as proteins and DNA and, thus, impli-
cations for health and disease.
For example, Zhang says, patients
with inflammatory disease may receive a
solution of monoclonal antibodies. The
treatment, dispensed in mass-produced,
prefilled syringes, needs to have a two-year
shelf life. The ions added in the form of salts
or buffer reagents to the protein solution
are crucial for maintaining protein stability.
Different ions are better or worse at pre-
venting aggregation and self-association.
Researchers have no good way to predict
this behavior.
At the core of the problem lies a phe-
nomenon discovered in the late 1800s by
the Czech chemist Franz Hofmeister. He
discovered that certain aqueous ions fol-
low a peculiar order in their increasing or
decreasing ability to precipitate egg whites
in solution. Anions in particular, such as
SO
4
2
, Cl

, and SCN

, follow a seemingly
arbitrary sequence: In this order, they
increasingly can denature and dissolve
proteins, and have increasing or decreasing
effects on many other solution properties,
such as surface tension.
This so-called Hofmeister effect lay
relatively unexplored for de-
cades, until the past 15 years,
when experimental and com-
putational methods allowed
chemists to reexamine the pos-
sible sources of the effect. Since
then, the Hofmeister effect has
formed the subject of hundreds
of papers, with scientists devis-
ing increasingly intricate and di-
verse experiments, with sophis-
ticated theoretical explanations.
Numerous meetings now focus
on the topic, including conferences this
summer hosted by the Telluride Science
Research Center and the Royal Society of
Chemistry .
Scientists are making some progress in
understanding the mechanisms behind the
mysterious Hofmeister order, but consen-
sus is lacking. Some say that relying on an
immutable Hofmeister effect may not even
be the right way to think about the problem.
Changes in pH or salt concentration, they
point out, can cause the series to reverse
and the strength of the ions dissolving abil-
ities to follow an opposite trend from the
original Hofmeister series. Such unpredict-
ability means chemists like Zhang still have
a great deal of work cut out for them.
How ions in water behave is still a mys-
tery, Zhang says.
THE EXPLANATION set forth for decades
was that ions produced long-range ef-
fects on the structure of water, leading to
changes in waters ability to let proteins fall
out of, or stay dissolved in, a solution. That
idea has largely been discarded.
The current view, explains M. Thomas
Record Jr. , chemistry and biochemistry
professor at the University of Wisconsin,
Madison, is that Hofmeister effects stem
largely from the varying abilities of differ-
ent salt ions to replace water at nonpolar
molecular or macroscopic surfaces. But
no theoretical framework can yet predict
these actions.
Much recent Hofmeister work has fo-
cused on the behavior of ions at interfaces:
between air and water, oil and water, or
protein and water. Some scientists reason
that experiments exploring ion
behavior at air-water interfaces
could eventually shed light on all
interfaces, leading to a general
mechanism.
For example, University of
California, Berkeley, chemistry
professor Richard J. Saykally
performed what he calls excru-
ciatingly hard spectroscopic
experiments on the behavior of
thiocyanate ions in water. Com-
bined with theoretical studies
HOFMEISTER STILL
MYSTIFIES
After decades of study, researchers struggle to explain
the ordering of AQUEOUS ION EFFECTS on proteins
ELIZABETH K. WILSON , C&EN WEST COAST NEWS BUREAU
ION ATTRACTION In this simulation,
SO
4
2
(gray), Cl

(orange), SCN

(yellow),
and Na
+
(green) ions cluster around the
backbone of a polypeptide.
P
A
V
E
L

J
U
N
G
W
I
R
T
H
ORDER IN THE SOLUTION Ions in the Hofmeister
series, from left to right, decrease in ability to augment
surface tension and increase in ability to dissolve proteins.
43
P
A
V
E
L

J
U
N
G
W
I
R
T
H
from Saykallys UC Berkeley colleague,
chemistry professor Phillip J. Geissler, the
research showed that weakly hydrated ions
are driven to the surface, where they then
smooth surface roughness ( Proc. Nat. Acad.
Sci., DOI: 10.1073/pnas.1116169109 ). This
complicated combination of events causes
the ions properties to follow the Hofmeis-
ter series.
OTHER RESEARCHERS focus on ions
interactions with biomolecules, and they
come to other conclusions.
Paul S. Cremer , a chemistry professor at
Texas A&M University, believes the abili-
ties of ions to affect surface tension, pro-
tein solubility, and other phenomena arise
from different physical causes, rather than
a single mechanism. His group recently
studied the binding of anions such as SCN

,
I

, SO
4
2
, and Cl

to an elastin-like polypep-
tide. Using modeling results from Pavel
Jungwirth , a chemistry professor at the
Academy of Sciences of the Czech Repub-
lic in Prague, the group determined that
the SCN

and I

ions interacted strongly
with a site consisting of the backbones
amide nitrogen and the adjacent -carbon.
The ions binding strength followed the
Hofmeister series ( J. Am. Chem. Soc., DOI:
10.1021/ja301297g ).
However, Cremer notes, this simple
picture will become significantly more com-
plicated when ions encounter full-sized pro-
teins many polar and charged side chains.
Barry W. Ninham , an emeritus chem-
istry professor at Australian National
University, in Canberra, who has spent
a large part of his career exploring the
Hofmeister effect, maintains that the
complexities are daunting ( Chem. Rev.,
DOI: 10.1021/cr200271j ). Numerous fac-
tors that influence the properties of aque-
ous ions, he says, have only recently been
recognized.
Hofmeister is something thats re-
discovered every 10 years, Ninham says.
Then interest in it subsides when people
realize its a sisyphean task.
For example, he notes, scientists have
yet to factor into their biomolecular mod-
els dissolved gases common in biological
systems such as oxygen and nitrogen and
their potentially significant effects on pro-
tein behavior.
Those who hope for a unifying theory
of Hofmeister may ultimately be disap-
pointed, Cremer predicts: The chemistry
is rich and interesting, but Hofmeister has
no single holy grail.
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44
SCI ENCE & TECHNOLOGY I NSI GHTS
BATHROOM SCALES rarely give reason to celebrate. By the time
you step up and wait for the creaking springs to equilibrate, an
uncomfortable feeling grabs hold: How much damage did that
chocolate glazed doughnut do?
On average, Americans weigh 25 lb more today than they did
50 years ago, at a cost of $147 billion in annual obesity-related health
care, according to the Centers for Disease Control & Prevention.
Overeating (my problem) and a sedentary lifestyle (not my prob-
lem) are key reasons. But scientific evidence
trickling in suggests that eating less and exercis-
ing more may not be enough to help solve the
obesity crisis. We need to cut out most table sug-
ar and other caloric sweeteners from our diets.
The dietary sugar focus has mostly been on
high-fructose corn syrup (HFCS). This sweet-
ener cropped up in the U.S. in the 1970s when
sugar import tariffs and corn subsidies sud-
denly made HFCS a cheap sugar substitute. By
1985, HFCS had replaced sugar in many processed foods and most
soft drinks; the HFCS fraction of total added sugars consumed in
the U.S. went from none to about half. HFCS accounts for less than
10% of caloric sweeteners used in the rest of the world.
During the past decade, nutritionists, medical researchers, con-
sumer advocacy groups, and corn refiners went through a cyclical
debate over whether sugar and HFCS are nutritionally different or
nearly enough the same.
Table sugar is sucrose, a disaccharide made of equal amounts of
fructose and glucose derived from cane or sugar beet juice. By con-
trast, HFCS is a mixture of free fructose and glucose. Its made by
first hydrolyzing the polysaccharides in cornstarch to form glucose
and then enzymatically isomerizing most of the glucose to fruc-
tose. The final fraction of fructose is adjusted by diluting with more
glucose. HFCS-55, containing a 55:42 mixture of fructose
and glucose, is typically used in soft drinks; HFCS-42, a
42:53 mixture, is typically used in processed foods.
By now, all parties agree theres no nutritional dif-
ference between sugar and HFCS. And by definition, a
calories worth of fructose is equal to a calories worth of
glucose, whether it is derived from HFCS or from sucrose
hydrolyzed during digestion.
However, the body doesnt care about definitions. We
absorb fructose and glucose by different mechanisms. Once in the
bloodstream, the two sugars follow different biochemical pathways:
Insulin-regulated glucose is involved in getting energy into cells
throughout the body, whereas insulin-independent fructose plays a
role in glycogen, triglyceride, and cholesterol production in the liver.
The real issue isnt HFCS versus sugar, or fructose versus glu-
cose. Rather, it is that too much sugar in any form is contributing to
obesity, type 2 diabetes, high blood pressure, heart disease, cancer,
and perhaps even autism. That is where the sweetener debate has
now turned.
To hear endocrinologist Robert H. Lustig of the University of
California, San Francisco, tell it: HFCS and sugar are equally bad.
They are poison. And even as most people have reduced salt and
fat in their diet to lower the risk of heart disease, as science has told
us to do, we havent lost any weight, Lustig argues. Thats because
we havent cut out the sugar, or at least not enough yet to make a
difference.
Lustig is a pioneer in the war against sugar. His May 2009 lec-
ture, Sugar: The Bitter Truth , became a hit on YouTube and ulti-
mately spawned a flurry of news reports earlier
this year on sugar and the American diet. Sci-
entists like Lustig are moved to preach because
they believe regulatory agencies are slow to act.
He posits that people originally got their
sugar in small amounts from the fructose in
fruit. Over time, our brains became wired to be
addicted to fructose, Lustig believes. We now
tend to gorge on sugar and HFCS, he says, and
it is the subsequent abnormal spikes in insulin
that are causing trouble: The extra fructose and glucose effectively
act like endocrine disrupters, Lustig suggests.
WHETHER THE SUGAR-IS-TOXIC THEORY holds up remains to
be seen, but Lustig and other scientists have redirected the focus
on the American obesity crisis and are getting people to think more
seriously about how much added sugar they consume. In 1970, the
average person in the U.S. consumed about 119 lb of added sugar,
according to the Department of Agricultures Economic Research
Service . The amount peaked at about 151 lb per year in 1999, but it
dropped to about 132 lb in 2010.
Nutritionist Barry M. Popkin of the University of North Caro-
lina, Chapel Hill, another sugar war veteran, has suggested signifi-
cant further cuts are possible by replacing HFCS and sugar in all
beverages with noncaloric sweeteners. We dont know
whether the use of such sweeteners has any long-term
health effects. But a study reported earlier this year by
Popkin and colleagues shows that substitution has the de-
sired effect: People who replaced sugar-sweetened bever-
ages with artificially sweetened drinks or water achieved
an average 2.5% weight loss over six months.
To phase out sugars from our diets will require a bolder
approach than just relying on reading nutrition facts and
willpower. New York City Mayor Michael R. Bloomberg is taking a
stab at it by trying to ban the sale of supersized sugary soft drinks.
But that tactic isnt likely going to work because people feel their
individual rights are being trampled upon.
In the end, we might just need to use scare-tactic labeling as we
have done to curb cigarette smoking: Surgeon Generals Warning:
This product contains high-fructose corn syrup and/or sugar and
may make you fat and cause health problems. Its food for thought.
STEPHEN K. RITTER , C&EN WASHINGTON
Improving our health could hinge on SAYING GOOD-BYE to added sugars
The Bitter Side Of Sugars
Views expressed on this page are those of the author and not
necessarily those of ACS.
HFCS and
sugar are
equally
bad. They
are poison.
Glucose
42%
53%
Fructose
HFCS-55: 55%
HFCS-42: 42%
O
OH
OH
HO
HO
O
OH
OH
OH
HO
HO
OH
45
BOOKS
CONCERNS ABOUT natural resource
scarcity have prompted social scientists to
take a strong interest in mineral resources,
from points of
extraction to con-
sumer use. The
most provocative
aspect of social sci-
ence research on
extractive indus-
tries has been the
resource curse
theory. This broad-
ranging theory,
proposed largely
by economists and
political scientists,
suggests that
mineral wealth
has attributes that
correlate with
negative develop-
ment outcomes for
countries.
Various natural
resourcesin-
cluding diamonds
and coltan (co-
lumbium and tan-
talum ores), which
are fueling conflict in Central Africahave
been the focus of resource curse studies
and efforts to address the problem, such as
the Kimberley Process, which was devised
to prevent so-called conflict diamonds
from entering the mainstream rough-
diamond market.
Both Michael T. Klare and Michael L.
Ross have published widely on the re-
source curse, covering various extractive
industries. Klares publications, written
largely for popular audiences, are based
on secondary material. Ross has published
several technical studies predicated on
regression analyses of development indica-
tors, as well as policy
analysis articles.
In their most
recent books
Klares The Race
for Whats Left: The
Global Scramble
for the Worlds
Last Resources
and Rosss The Oil
Curse: How Petro-
leum Wealth Shapes
the Development
of Nationsboth
scholars attempt to
synthesize perspec-
tives on the future of
resource conflicts.
Ross focuses on
what he views as the
most consequential
extractive resource,
oil, whereas Klare
grapples with the
larger question of
mineral scarcity for
human use and the
geopolitical impacts of seeking minerals in
ever more remote parts of the planet.
Chemists have often struggled with the
notion of nonrenewability of an element
as described in environmental studies dis-
course. The elements, after all, are infinite-
ly renewable through chemical reactions so
long as the requisite energy can be applied.
(Many social scientists fail to note that
only a nuclear reaction can truly transform
an element.)
Indeed, the question of resource scarcity
of the elements, most notably metals, can-
not be framed without reference to energy
resources. For this reason, coal, oil, and
natural gas, which are the most commonly
used forms of industrial energy, need to be
considered in sync with elemental scarcity.
KLARE MAKES THIS connection by in-
cluding a chapter in The Race for Whats
Left on oil sands and shale gas alongside
one on rare-earth minerals (largely ele-
ments from the lanthanide and actinide
rows of the periodic table). He also takes
the next step of focusing on the scarcity
of land for competing resource uses, most
notably agriculture. Interwoven within
the engaging anecdotes of icebreakers
searching for oil and gas in the Arctic and
gold rush frontiers in Mongolia is an urgent
concern about the geopolitical conflict this
scramble for minerals might create.
Klares tone is more measured than in
his earlier book Resource Wars, but he
remains highly skeptical of technological
fixes to our predicament. Indeed, concern
is growing even among technologists that
many energy-saving devices themselves
depend on rare-earth minerals. Hence the
nexus between energy and the elements
becomes even more confounding.
A study by a research team at Massachu-
setts Institute of Technology published
shortly before The Race for Whats Left
came out, for example, warns of severe
scarcity of rare earths if green technology
demand continues at projected rates ( Envi-
ron. Sci. Technol., DOI: 10.1021/es203518d ).
What such works on metal scarcity tend to
neglect, however, are the growing efforts
by industry to redesign products to make
recovery and recycling of materials easier.
Designing products for resource recovery
according to an industrial ecology para-
digm may well be our best bet to avert seri-
ous geopolitical struggles over minerals.
That said, it is unfortunately true that
geopolitical approaches to resource
scarcity are thus far following a more bel-
ligerent and less technically informed
approach. Most recently, the Obama Ad-
ministrations decision to lodge an official
complaint against China with the World
Trade Organization regarding its reduction
of rare-earth mineral exports gives further
credence to Klares concerns. Ironically,
MINERAL RESOURCES
AND SOCIETY
A pair of books examine SOCIAL SCIENCE RESEARCH,
geopolitical impacts of the extractive industries
REVIEWED BY SALEEM H. ALI
The most provocative aspect of social science research on
extractive industries has been the resource curse theory.
THE RACE FOR
WHATS LEFT:
The Global
Scramble for
the Worlds Last
Resources , by
Michael T. Klare ,
2012 , Metropolitan
Books, 320 pages,
$27 ( ISBN-13:
978-0805091267;
ISBN-10:
0805091262 )
THE OIL CURSE:
How Petroleum
Wealth Shapes
the Development
of Nations , by
Michael L. Ross ,
2012 , Princeton
University Press,
296 pages, $29.95
( ISBN: 978-0-691-
14545-7 )
46
the reason given by China for reducing the
supply of rare earths is to ameliorate envi-
ronmental standards at its mines, which is
exactly what U.S. environmental interests
have often called for. Economic expediency
and ecological planning clearly need to be
more functionally operationalized within
the context of mineral policy.
IN CONTRAST WITH The Race for
Whats Left, Rosss The Oil Curse is
less concerned about resource scarcity
per se and more interested in the qualita-
tive impact of mineral extraction. Apart
from his academic work, Ross has also
advised nonprofit organizations such as
Oxfam, and he acknowledges the sup-
port he received from the Revenue Watch
Institute, an organization established by
philanthropist George Soros to promote
transparency in natural resource econo-
mies. To his credit, Ross notes that earlier
studies he conducted had perhaps been
too simplistic and that he appreciates the
criticism he received from other academ-
ics, which helped him refine his methods
for the current volume. Rosss empirically
driven tone and willingness to engage with
criticism give the volume further credibil-
ity, but his use of statistical regression to
explain causality between oil wealth and
social problems still requires underlying
assumptions.
The premise of The Oil Curse is that
hydrocarbon wealth has four key attributes
that lead to its potential for being cursed:
scale, source, stability, and secrecy. Hy-
drocarbon projects have massive capital
investment (scale); they are not funded by
citizen taxation or innovation incentives
and are hence less connected to democrat-
ic parameters (source); they are beholden
to volatile commodity markets (stability);
and revenues from oil are easy to conceal
given the contract norms between compa-
nies and governments (secrecy).
Ross further contends that the curse
started to gain traction when state-run
oil companies became more common.
Such companies have much less account-
ability than privately held firms, and Ross
considers their structure a major cause for
perpetuating the oil curse. Therefore,
although corporate executives may find
Rosss negative revelations about the es-
sential lubricant of modern capitalism to
be troubling, they can gain some solace
that he strongly blames this outcome on
government control of industry. However,
Ross remains nuanced about assigning cul-
pability by also noting that private-sector
management still needs some government
oversight to be constructive.
Rosss key prescription to grapple with
the oil curse is developing mutual account-
ability between the private and public sec-
tors. Taxation remains an important tool in
this context to ensure that sudden wealth
accumulated by corporate oligarchs can be
better distributed across a population. Do-
mestic legislation requiring transparency
to track resource royalties and their spend-
ing and the international norms that hold
companies and governments accountable
through treaty obligations or trade norms
are likely to prevent the oil curse.
Even though Rosss analysis of the
macroeconomic impacts of oil wealth is
compelling, he tends to stretch their impli-
cations by focusing on tenuous indicators
such as womens rights. Chapter 4, Petro-
leum Perpetuates Patriarchy, is perhaps
the least convincing part of the book. Al-
though it offers an alternative narrative to
dominant views on the misogynistic laws
of some Middle Eastern countries and may
win applause for political correctness, the
causal linkages argued here are flimsy. Un-
derplaying the role of Islamic tradition and
myriad historical factors, which a regres-
sion-based methodology cannot possibly
account for, renders this chapter weak.
ROSS ALSO TENDS to use data selective-
ly, thereby missing the forest for the trees.
For example, Ross heralds non-oil-produc-
er Morocco for female emancipation and
literacy (as a percentage of the total literate
population), while ignoring the fact that
in total, the country has the lowest literacy
rate of all the Maghreb countries. At the
same time, he neglects multi-billion-dollar
investments in education and female lit-
eracy by oil producer Qatar.
Rosss perspectives on connecting
gender rights to hydrocarbon economies
have been critiqued widely in the literature
by scholars such as Pippa Norris and is
problematic for policy reform efforts in
the Middle East on issues such as womens
rights. For example, Rosss analysis can be
used to undermine activism for curricular
reform in Islamic schools by deflecting
the conversation toward oil, rather than
addressing the theological inertia that is
directly linked to misogynistic practices.
When making such broad causal connec-
tions, social scientists need to be more
wary of presenting tenuous theories of
underdevelopment that could be misused
An up-to-the-minute
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including coverage of
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47
BOOKS
The primacy of minerals as
our ultimate resource base and
the reliance of modern society
on the elements must never es-
cape our policy horizon. As the
U.S. Congress considers legis-
lation related to extractive in-
dustriesfrom reforming the
1872 Mining Act to amending
the conflict-mineral provisions
of the Dodd-Frank Wall Street
Reform & Consumer Protec-
tion Act we need informed
analyses on mineral econo-
mies. International efforts
such as the Extractive Indus-
tries Transparency Initiative
and myriad industrial efforts
to improve corporate social re-
sponsibility need to be watched
closely for progress.
Reading Klare and Ross
should provoke us to be con-
cerned, even if we do not agree
with all of their conclusions.
Scholars across disciplines
have much to contribute in
finding effective means of harnessing the
full potential of minerals in improving
our lives without irreversibly harming the
planet.
dilemmas. At the same time, social sci-
entists who usually present governance
solutions focused on transparency around
the extractive sector should couple their
approach with a greater understanding
of technical processes. Understanding
mineral cycles and basic concepts around
natural resource use such as entropy and
exergy could further inform the research of
scholars such as Klare and Ross.
to perpetuate negative cultural
inertia.
Despite Rosss methodologi-
cal overstretch and Klares ten-
dency to be a polemical pessi-
mist, both books are important,
because the role of minerals in
our lives needs to be examined
critically. Ross and Klare are to
be applauded for advancing the
conversation beyond reveling in
the history of human extraction
of resources to expressing sor-
row for the negative impacts of
mineral rushes, which most so-
cial science books in this genre
tend to follow.
They are also willing to engage
with the tough issues around
scarcity, underdevelopment, and
conflict that celebrated writers
on mineral history and policy
such as Daniel Yergin (author
most recently of The Quest)
have deliberately avoided be-
cause of their strong connec-
tions to industry.
Although technological efforts must
continue to improve our chances to meet
the mineral needs of society, a sanguine
reliance on technology to resolve the social
issues of extractive economies would be
reckless.
Cautionary narratives such as these
books are important for engineers and
chemists to read to further hasten the
search for solutions to resource scarcity
SALEEM H. ALI is director of the Centre
for Social Responsibility in Mining at the
University of Queensland, in Australia. He can
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AWARDS
THREE TITANS OF SCIENCE and busi-
ness received awards at the annual Heri-
tage Day celebration in April at the Chemi-
cal Heritage Foundation (CHF) in Philadel-
phia. Each acknowledged they owed their
success in part to the U.S. academic climate
over the past 30 years. However, two of
the recipients wondered if that setting will
produce the award winners of the future.
Receiving the Richard J. Bolte Sr. Award
for Supporting Industries was G. Steven
Burrill, chief executive officer of biotech-
nology investment firm Burrill & Co.
Elizabeth H. Blackburn, winner of the 2009
Nobel Prize in Physiology or Medicine for
her discovery of telomeres and their role in
aging and cancer, received the American In-
stitute of Chemists Gold Medal. And Marye
Anne Fox, professor of chemistry and chan-
cellor of the University of California, San
Diego , received the Othmer Gold Medal.
Burrill arrived in Philadelphia a day
before the April 12 Heritage Day festivities
to participate in a recorded chat on The
Changing World of Biotech with CHF
Chancellor and former president Arnold
Thackray. Speaking before an audience of
about 50 people in CHFs spacious Ullyot
Meeting Hall, the biotechnology venture
capitalist said he was optimistic about the
future of health care because genomics
and proteomics will transform the health
care system, allowing doctors to anticipate
disease and treat patients before they be-
come ill.
MOST OF THE MAJOR biotechnology ad-
vances of the past 30 years came out of U.S.
academic research, but the same is unlikely
to be true in the years ahead, Burrill said.
The National Institutes of Health s budget
is going down on an absolute basis, he not-
ed, while Chinese government support of
health-related research is on the upswing.
The U.S. wont be the worlds dominant
economic engine for the next 100 years, he
said, noting the booming economies, grow-
ing consumer demand, and burgeoning re-
search prowess of countries such as China,
India, Russia, and Brazil.
Burrill also criticized U.S. immigration
laws, which do not allow foreign scientists
to remain in the U.S. after getting their ed-
ucation in this country. Now we educate
them and then throw them out after teach-
ing them to eat our lunch, he said.
The next afternoon at the Bolte Award
A CELEBRATION
OF CHEMISTRY
Trendsetters honored with HERITAGE DAY AWARDS
are concerned about the future
MARC S. REISCH , C&EN NORTHEAST NEWS BUREAU
Gassman Award to Franklin A. Davis
The ACS Division of Organic Chemistry
has named Franklin A. Davis Laura
H. Carnell Professor of Chemistry
at Temple University, Philadelphia,
PA the winner of the 2012 Paul
G. Gassman Distinguished Service
Award. The award sponsored by Bayer,
was established in 1994 to recognize
outstanding service to the organic
chemistry community. Presented
biannually at the divisional executive
committee dinner of the Fall ACS
National Meeting, the award consists
of a plaque and a citation certifcate.
Professor Davis received his B.S. degree from
the University of Wisconsin in 1962 hav-
ing completed undergraduate research
studies with Peter S. Wharton and com-
pleted his Ph.D. work with Donald C. Ditt-
mer at Syracuse University in 1966. After completing Post-doctoral
studies at the University of Texas with Michael J.S. Dewar he began
his academic career at Drexel University in 1968. In 1995 he moved
to Temple University as Professor of Chemistry and became the
Laura H. Carnell Professor of Chemistry in 2009.
Professor Davis has been advancing the
interests of the members of the Division
of Organic Chemistry as a member of the
Executive Committee for over twenty four
years. Frank served as the frst National
Program Chair and was instrumental in the
development of the frst scheduling software
for ACS meetings. In 2005 he pioneered and
developed the function of Regional Meeting
Liaison to encourage organic programming
at regional meetings, a position he still holds
today. He has also served as Division Chair,
Counselor, and on various committees, ad-
visory boards, study sections and editorial
boards.
Professor Davis is well known for his work in
the design and application of sulfnimines
(N-sulfnyl imines) to the asymmetric
synthesis of amines. Two of these reagents
bear his name, the Davis oxaziridine and
the Davis sulfnimine. He is a Fellow of
the American Chemical Society and the
Royal Society of Chemistry. He has received
numerous awards including the Cope
Scholar Award, the Philadelphia John Scott
Award, and a fellowship from the Japan Society for the Promotion
of Science.
49
PROVEN WINNERS
Burrill (seated, from
left), Blackburn,
and Fox join award
presenters John
Bolte of BDP
International
(standing, left) and
David Kumar of the
American Institute of
Chemists.
ceremony with a group of about 150 in at-
tendance, Burrill picked up with similar
themes. But he focused his talk more
broadly to address innovation during a
time of austerity. He said he believes the
biggest challenges facing the worldsuch
as climate change,
energy availability,
and cost-effective
health careall
will be answered
by the world of
biotech.
Following Bur-
rill, Gold Medal
Award winner
Blackburn, who is
currently a professor of biology and physi-
ology at UC San Francisco, talked about
her research. She described her journey
from growing up in Australia to graduate
research work in England at the University
of Cambridge and then postdoctoral work
in molecular and cellular biology in the U.S.
at Yale University. A grant from NIH led to
her discovery of telomerase enzymes and
their role in cell replication and mortality.
After an evening dinner in her honor,
Othmer Gold Medal winner Fox talked to
125 attendees about disturbing trends in
educational funding that she feels will ulti-
mately lead to the demise of U.S. leadership
in science. She noted that cuts in the state
governments support of the University of
Californias budget will compromise the
institutions ability to attract the best and
brightest students. And she predicted that
as California goes, so goes the nation.
Fox noted that the U.S. lead in science
today rests on contributions from many
years ago. Along with the investment in
education, a culture grounded in risk-taking
and entrepreneurship helped advance many
technology-based enterprises in the U.S.,
she said. The recent trend to outsource
advanced technology jobs to developing
countries in Asia means that R&D goes
abroad and along with it the intellectual and
economic opportunities of the future.
Fox also underscored the deplorable
lack of basic scientific knowledge among
Americans. And to retain the skill of for-
eign students, she suggested that U.S.
policymakers lift restrictions preventing
foreign-born graduate students at U.S. col-
leges from remaining in the country after
receiving their degrees.
I am grateful for the education I have
had in the U.S., Fox said. All I want for our
American students is what I was given.
C
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CRAIG W.
LINDSLEY
EDITOR
INCHIEF
200
FOUNDED
IN
Introduced in 2010, ACS Chemical Neuroscience recorded its frst ever Impact Factor in 2011 of 3.676* ranking it #9 among all
journals in Medicinal Chemistry. The journal publishes articles and reviews that showcase chemical, quantitative biological,
biophysical and bioengineering approaches to the understanding of the nervous system and to the development of new
treatments for neurological disorders.
ST

EVER IMPACT FACTOR: 3.676
Follow the journal today at pubs.acs.org/r/follow
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50
MEETI NGS
BY PAYING INSUFFICIENT attention
to the physical, solid-state properties of
drug compounds, the pharmaceutical in-
dustry has missed opportunities for new
drugs and imposed untold costs on itself,
according to a group of industry leaders.
Drug companies can better carry out their
core dutycreating new medicinesby
drawing more rigorously on materials sci-
ence and engineering and translating this
fundamental science into pharmaceutical
development, they say.
To promote this goal, the group launched
the M3 conference, named for Molecules,
Materials, Medicines. The third M3 meeting
took place on May 1922 in Banff, Alberta.
The group includes rn Almarsson and
Magali Hickey of Alkermes, Patrick Con-
nelly and Michael (Mick) Hurrey of Vertex
Pharmaceuticals, Drazen Ostovic of KO
Pharm R&D, Matt Peterson of Amgen, and
Elizabeth B. Vadas of InSciTech.
For years, they advocated for earlier and
more rigorous application of solid-state
materials science in pharmaceutical R&D.
They argued, both in their own workplaces
and at industry gatherings, that materials
science could help prevent costly disas-
ters in manufacturing ( Nat. Chem., DOI:
10.1038/nchem.1121 ; Science, DOI: 10.1126/
science.333.6039.156-b ), enable more dis-
covery assets to be developed than would
make it to market otherwise ( Nat. Rev. Drug
Discovery, DOI: 10.1038/nrd1550 ), and allow
more deliberate, rational drug design. For
instance, analyzing the crystal structures
of drug substances makes it possible to
develop crystallization processes that allow
precise control of particle size and mor-
phology, which affect drug performance.
However, in all of these areas, opportu-
nities to share knowledge and best prac-
tices were rare. For this reason, the group
decided to host a conference that would
gather the fields leading lights for an in-
tensive focus on solid-state chemistry in
the drug industry, defining and potentially
advancing the state of the art.
THE FIRST M3 conference took place in
2007 in Reykjavik, Iceland, and the second
one was held in 2009 in Santa Barbara,
Calif. By 2012, the organizers thought that a
third M3 conference was in order.
No one doubted that the meeting would
be useful, but for the organizers, it was an
uphill trek. As a group of individuals, they
were operating outside any infrastructure.
They had no institutional tax-exempt sta-
BRINGING MATERIALS
SCIENCE TO PHARMA
M3 CONFERENCE highlights the importance of solid-
state science to the development of new drugs
ST

DENNIS
C. LIOTTA
EDITOR
INCHIEF 67%
ARTICLE
GROWTH
IN 20
Introduced in 2010, ACS Medicinal Chemistry Letters recorded its frst ever Impact Factor in 2011 of 3.355* ranking it #12
among all journals in Medicinal Chemistry and frst among its competitors. The journal publishes brief communications
on experimental or theoretical results of exceptional timeliness in all aspects of medicinal chemistry (pure and applied)
and its extension into pharmacology.
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51
tus or economy of scale, and their oppor-
tunities to communicate with potential at-
tendees, speakers, and others were limited
to what they could manage themselves.
This is why, for the benefit of both
groups, the M3 organizers partnered with
the ACS Division of Business Development
& Management (BMGT). This collabora-
tion put BMGTs publicity and commu-
nications systems at their disposal. The
division, meanwhile, had compelling rea-
sons to work with M3. The conference was
aimed at senior and management-level sci-
entistsa demographic that could stand
to gain from getting involved with BMGT.
In addition, the M3-BMGT partnership was
able to serve as a proof of concept. BMGT
was able to test whether it could help put
on a small, specialized, highly targeted
conference that would generate important
scientific insights while covering its costs.
At this point a number of sponsors came
on boardnotably Amgen, Patheon, Ver-
tex, and Xcelience, in addition to Agilent
Technologies, Alkermes, Bend Research,
Crystal Pharmatech, Hovione, Johnson
Matthey Pharma Services, and Merck & Co.
Then in May of this year, the attendees
gathered at the Banff Centre. The confer-
ence opened with events intended to get the
attendees creative juices flowing. A keynote
address that was deliberately outside most
of their specialtiesa talk on ionic liquids
by Robin D. Rogers of the University of
Alabamawas designed to bring the par-
ticipants beyond their intellectual comfort
zones.
THE NEXT TWO DAYS of the conference
focused on the science that everyone had
come to talk about. A panel on amorphous
pharmaceutical materials included George
Zografi of the University of Wisconsin,
Madison. Konstantin Borisenko of the Uni-
versity of Oxford, well-known in the field
of inorganic materials science, joined this
panel as well; his cross-disciplinary perspec-
tive was fitting for the spirit of the meeting.
That panel preceded one on the uses
of crystallography in drug development
that included Michael F. Doherty of the
University of California, Santa Barbara.
A session on the uses, development, and
scale-up of cocrystals followed, featuring
Mike Zaworotko of the University of South
Florida. The conference also covered the
state of the art in materials characteriza-
tions and included scientific presentations
by service providers.
Feedback was overwhelmingly positive.
Attendees enjoyed the interactive nature of
a small conference, had thought-provoking
conversations, made important connec-
tions, and stayed engaged. Many expressed
the opinion that M3 should occur on a reg-
ular basis every two to three years, keeping
the same focused and interactive format.
The conference was a success from a
management perspective as well: It fin-
ished with a slight profit, so it was able to
cover administrative costs and set aside
seed money for a future M3 conference. In
light of the outcome, BMGT says it is eager
to pursue this kind of partnership again
in the future. By providing a forum for in-
depth, rigorous science coupled with prac-
tical industrial chemistry, the M3 confer-
ence fulfilled the ACS divisions mission of
creating value while advancing science.
MICHAEL HURREY & BRIAN PATRICK QUINN ,
special to C&EN
GEORGE
C. SCHATZ
EDITOR
INCHIEF
PRASHANT
V. KAMAT
DEPUTY
EDITOR
Introduced in 2010, the Journal of Physical Chemistry Letters recorded its frst ever Impact Factor in 2011 of 6.213*,
ranking it #1 in the category of Physics, Atomic, Molecular & Chemical. The journal covers all topic areas currently
included in the Journal of Physical Chemistry A, B, and C.
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VIDEO ONLINE
A
s anyone who saw Miss Piggys ap-
pearance as a judge on the TV show
Project Runway: All Stars earlier this
year can attest, pigs have style. So much so,
the porkers are STRUTTING THEIR STUFF
as part of a Ph.D. project being conducted
by graduate student Sophia Stavrakakis at
Newcastle University , in England.
Stavrakakis is gathering data that corre-
late a female breeding pigs gait to its likeli-
hood of eventually becoming lame. Such
metrics could
help farmers
pinpoint at-risk
swine in need
of preventive
care, thereby
minimizing
costly livestock
fatalities.
To prep swine
for this study,
Stavrakakis
teammate Mark
Brett, a former
zookeeper at ZSL London Zoo, trained a
group of pigs to walk in front of a three-di-
mensional motion-capture camera system
that measures the length of a pigs stride
as well as the angles exhibited by its elbows
and knees. During training, Brett placed a
stick with a red ball at its end
in front of a pig. The pig then
touched the ball with its nose,
received an apple treat, and
continued following the ball as
Brett paraded the pig in front of
the cameras. We trained them
to follow a guiding tool, like
dogs basically, Stavrakakis tells
Newscripts. They picked it up
quite quickly.
Gently leading the pigs at a
set pace ensures consistency
among the data being collected
over the course of the pigs lives.
Documentation of how the gaits
of female breeding pigs change
as they grow older and gain weight will be
a useful benchmarking tool for farmers,
Stavrakakis says, and might facilitate the
development of video-based technology
for screening pigs and agging those more
likely to experience problematic health in
the future.
Its an efort that Stavrakakis snout-nosed
SASHAYI NG PI GS, ENORMOUS BUCKYBALLS
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friends have been more than happy to, ahem,
ham it up for. Some of them were really
enjoying the walking, Stavrakakis laughs.
F
or we humans looking for a good ex-
cuse to take a stroll of our own this fall
and winter, Madison Square Park has
just the attraction: a GIANT BUCKYBALL
sculpture. The 30-foot-tall representation
of C
60
will be on display at the New York
City park from Oct. 25 until sometime in
February 2013.
Commissioned by
Madison Square Park
Conservancy s public art
program , the massive
structure is the work of
artist Leo Villareal , the man
behind such impressive
light sculptures as Mul-
tiverse, which connects
the east and west wings
of the National Gallery of
Art in Washington, D.C.
Much like Multiverse,
Villareals soon-to-be-installed Buckyball
makes extensive use of light-emitting diodes.
One hundred and eighty LED tubes line the
pentagon- and hexagon-shaped sides of
his pieces two fullerenes, which have been
placed one inside the other. Pixels within
the LEDs bathe the structure in
waves of as many as 16 million
distinct colors.
A full-scale sculptural instal-
lation that moves, changes, and
interacts, this work ultimately
grows into a complex, dynamic
form that questions common
notions of space, time, and
sensorial pleasure, a press re-
lease for the sculpture proudly
proclaims. Although Newscripts
remains skeptical about the
kind of existential quandaries
Villareals Buckyball may
throw us into, we do agree that
the epic size of the installation
is enough to make us wonder if, at least dur-
ing the coming fall and winter, the Big Apple
should instead be called the Big Buckyball.
JEFF HUBER wrote this weeks column.
Please send comments and suggestions to
newscripts@acs.org.
To see how a pigs gait is recorded via motion-capture
technology, check out cenm.ag/pigwalk.
Simply porcine: Stavrakakis poses
with a test subject.
Rendering of
Buckyball: High-
wattage piece will
attract bugs and
tourists.
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44th IChO TEAM
Sidharth Chand, Detroit Country Day School, Beverly
Hills, Mich.
James Deng, Choate Rosemary Hall, Hamden, Conn.
Jason Ge, Westview High School, San Diego, Calif.
Christopher Hillenbrand, Regis High School,
New York, N.Y.
44th IChO TEAM ALTERNATES
Timothy Lee, Arcadia High School, Arcadia, Calif.
Andrew Guo, Scarsdale High School, Scarsdale, N.Y.
44th IChO Other Finalists
Justine Jang, Livingston High School, Livingston, N.J.
Brandon Kao, Valencia High School, Placentia, Calif.
David Liang, Carmel High School, Carmel, Ind.
Runpeng Liu, Ladue Horton Watkins High School,
St. Louis, Mo.
Alexander Nie, Livingston High School, Livingston,
N.J.
Ruifan Pei, Acton-Boxborough Regional High School,
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Kalki Seksaria, Thomas Jeerson High School for Science
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Stephen Tang, Solon High School, Solon, Ohio
Kevin Tie, East Chapel Hill High School, Chapel Hill, N.C.
Stephen Ting, Monta Vista High School, Cupertino,
Calif.
Jessica Xu, Watchung Hills Regional High School,
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Grace Zhang, East Brunswick High School, East
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Cindy Zhao, Brecksville-Broadview High School,
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Angela Zou, Torrey Pines High School, San Diego,
Calif.
K
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U.S. IChO Team members Ge (from left),
Chand, Hillenbrand, and Deng
ACS and C&EN congratulate
the 2012 U.S. National Chemistry Olympiad Team
and all of the fnalists.
coverwrapIBC.indd 1 7/2/12 12:55 PM
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