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CHEM DOT POINTS: PRODUCTION OF MATERIALS

1.2
Ethylene is produced either from natural gas or crude oil by thermal cracking and
catalytic cracking. Ethane and propane from natural gas can be thermally cracked to
produce ethylene. It can also be produced from fractional distillation of crude oil using
naphtha or gas oil fractions.
- Thermal cracking involves heating up ethane to
a very high temperature in a furnace, and then
piped to a refrigeration plant after being fed
through a quench boiler. Eg:
C 2 H 6 ( g ) →C2 H 4 ( g ) + H 2 ( g ) ∆H=
+138kj/mol
- Catalytic cracking breaks down very long chain
hydrocarbons into lighter fractions through the
use of a zeolite catalyst. Eg:
C10 H 22 ( l ) →C2 H 4 ( g ) +C8 H18 ( l )

1.3
Ethylene is an alkene, meaning is has a double bond, and is highly reactive. Because of
this, it can be transformed into many useful products.
- Addition reactions occur with ethylene to form alkanes and alcohols. Eg:
C2 H 4 ( g ) + H 2O →C2 H 5OH (ethanol), C2 H 4 + HCL →C2 H 5Cl
(chloroethane)
- Substitution reactions occur with ethylene to form vinyl chloride. Eg:
C2 H 4 + O2 + Cl 2 →C2 H 3Cl
- Other reactions include bromination to produce bromoethane.

1.4
Ethylene is a monomer, ie. It is a single molecule. Ethylene and similar monomers can be
polymerised to make long chain molecules called polymers.

1.5
Polyethylene is an addition polymer as is it formed by the molecules adding together
without the loss of any atoms. This forms because Ethylene has a double bond, which, in
polymerisation, breaks and connects with more atoms.

1.6
Polyethylene is formed by 2 processes
- LDPE: requires high temp range (100-300C) and very high pressure (1500-3000
atmospheres). An organic peroxide or oxygen is used as an initiator to allow many
monomers (about 2000) to join together. There are many side chains which
restricts the polymer to pack closely. This is used in cling film and other
containers such as cordial bottles.
- HDPE: requires temperature of about 60C with a few atmospheres of pressure.
Titanium(III) chloride is used as a catalyst in the zeigler-natta process. There are
no side branches on this polymer, which makes it pack together more and thus
have a higher density. This makes it suitable for use in stronger kitchenware and
things like plastic chairs.
MONOMERS POLYMERS
Common Systematic name Name Properties Used for
name
ethylene ethene LD polyethylene low density, food bags
soft
HD polyethylene high density, buckets
hard
vinyl chloride chloroethylene polyvinylchloride water resistant raincoats, shower
and flame curtains
resistant
acrylonitrile propenenitrile polyacrylonitrile strong, due to strengthening
attraction other polymers
between polar
cyanide groups
styrene ethenylbenzene polystyrene transparent, due CD cases
to few crystals

1.7
Vinyl Chloride is a commercially significant monomer as it can be polymerised
additionally to form PVC (polyvinylchloride). Chloroethene is produced when ethylene
reacts with chlorine in the presence of O2.
Styrene is commercially significant as it is a monomer that undergoes polymerisation to
form polystyrene. Styrene is produced when ethylene reacts with benzene (like the
chlorine in chloroethene) to produce a benzene ring in place of a hydrogen.

1.8
PVC
PVC can be used in packaging fatty and oily foods as it is
moderately resistant to chemical attack. Caustic chemicals such
as NaOH may attack PVC. It is a hard, inflexible and brittle
polymer, where its stiffness is increased by the chlorine atom. As
the chlorine atom is almost double the weight of each molecule,
which aids the increase in dispersion forces. Each molecule is
thus held in place more strongly so the material is not flexible
and hard.

Polystyrene
In polystyrene, the benzene side group has more mass, and thus dispersion forces
increase. Polystyrene is a rigid, tough plastic often used in the making of cookware and
hammers of chisels. There are two main types of polystyrene: crystal polystyrene and
expanded polystyrene (Styrofoam™).
Crystal polystyrene is a clear amorphous polymer that is stiff and has good electrical
insulation properties. It has a high refractive index which makes it suitable for drinking
glasses and audio cassettes.
Styrofoam is white and has good heat and sound insulation properties. It is used in
packaging, soft plastic cups and surfboards.
2.1
The current compounds used in the petrochemical industry are non-renewable, i.e. are
running out. Alternative fuel sources need to be utilised in order to reduce the usage of
conventional petrochemicals. Such alternative fuels include cellulose and ethanol.

2.2
Condensation polymer is a polymer which forms by a step-growth condensation
reactions, including the elimination of a small molecule (usually H2O) when pairs of
monomers join together.

2.3
Two monomers join together and a water molecule is eliminated. Each monomer loses
hydrogen and oxygen atoms to condensate, then join end on end to make long chain
polymers.

2.4
Cellulose is a biopolymer formed by the condensation polymerisation of glucose
molecules. Cellulose fibres are produced in plant cells, thus being a part of biomass
(biomass: carbon-based matter mainly from plants, that stores energy produced by
photosynthesis.) Glucose join in interlocking chains to produce cellulose.

2.5
Cellulose contains the basic carbon chain structures that are needed to build compounds
that are presently obtained from petrochemicals. Biomass is renewable, and is composed
of carbohydrates and lignin. Cellulose is a potential source of petrochemicals because of
its long carbon chain structure.
PROBLEMS
Cost- Biomass fuels are more expensive. Energy is needed to plant, fertilize, harvest and
process the energy from crops.
Suitable land- is needed to grow the crops. Eg sugarcane waste stalks and leaves can be
converted to ethylene and petrochemicals.
3.1

Ethanol can be converted back to ethylene by a process called dehydration. Concentrated


sulfuric acid is used to remove water from the ethanol molecule. Concentrated sulfuric
acid acts as a catalyst and dehydrating agent.
In industry, ethanol vapour is dehydrated by passing it over hot aluminia or ceramic
catalysts at 350°C

3.2
Addition of water to ethylene to make ethanol is called hydration. This can be done in
two ways.
Indirect Hydration
Ethylene is reacted with 98% sulfuric acid in absorption columns at 55-80°C and 1-3.5
MPa of pressure. This is then mixed with water until the sulfuric acid concentration is at
about 50% and then heated to approx 100°C.

C2H4 + H2O  CH3CH2OH

Catalytic Hydration
Steam and ethylene is passed over a silica gel or zeolite surface impregnated with
phosphoric acid catalyst. High pressure and high temperature (300oC) aids the formation
of ethanol. The steam concentrations must be kept low to avoid losing phosphoric acid.

3.3
Ethanol as a solvent:
- Ethanol can be used as a solvent for cosmetics (perfumes and deodorants), food
colouring and medical preparations (antiseptics).
- usually sold as methelated spirits
- a range of substances including polar, non-polar, and some ionic compounds
dissolve in ethanol.
- The ethanol molecule consists of two pairs , polar hydroxyl end, and the non-
polar alkyl end. The ability of ethanol to act as a solvent to polar molecules is due
to the polar nature of the OH bond. This interacts with polar molecules to form
dipole-dipole forces or hydrogen bonds.
- The alkyl chain is essentially non-polar and allows ethanol to act as a solvent for
some non-polar substances. These form dispersion forces, similar to the
intermolecular forces between solute molecules.

3.4
ETHANOL AS A FUEL
C6H12O6 + zymase (yeast) → 2CH3CH2OH + 2CO2


Ethanol (15%) solution is distilled
In a distillation column

Chemicals added to remove water

Distilled in a distillation column

Condensed, the end product is pure ethanol

It can be called a renewable resource as it is derived from biomass. Ethanol combusts in


air, releasing carbon dioxide, water and heat. Because the ethanol molecule contains an
Oxygen atom, the combustion is practically always complete. There is hardly any
formation of the polluting CO or C forms, which form from the incomplete combustion
of many other hydrocarbons.
Ethanol can be called a renewable resource because ethanol can be made from plant
material and the products of its combustion, carbon dioxide and water, are used by these
plants for photosynthesis and growth..
COMBUSTION:
C2H5OH(l) + 3O2(g)  2CO2(g) + 3H2O(l) ∆H= -1367kJ/mol
1 mol ethanol= 46.068g
EFFICIENCY:
- ethanol will burn more completely than octane in same conditions
- for each mol of fuel, octan requires more oxygen for complete combustion, but
also produces more energy.
- Longer chain alkanols burn less efficiently than the shorter chain alkanols and
produce more soot and CO2.
- Flash point of ethanol is higher than petrol.
- Ethanol’s ignition temperature is lower than that of petrol so a combustible
mixture will more readily ignite.

3.5
Conditions for Fermentation:
- Temperature needs to be approximately 37ºC. Too much heat will kill the yeast,
and too little will not allow the yeast to thrive. The enzymes in yeast are highly
sensitive to temperature so conditions must be kept consistent by removing excess
heat produced in the exothermic reaction. This is different for different types of
alcohol i.e. about 15ºC are needed to produce champagne.
- Anaerobic (without O2 present) conditions allow the yeast to respire the sugars to
obtain energy. If oxygen is present, the yeast will use the sugars and oxides them
to CO2 and water.
- For fewer than 15% concentration of ethanol, common yeast (not bakers) can be
used as above 15% ethanol will cause the organisms to die. For higher
concentrations, alcohol tolerant yeast strains need to be added as well as
distillation carried out.
- Water is needed as a solvent for the glucose and sulfur dioxide (to kill bacteria).
For fermentation to properly take place the sugars which are being broken down
must be in aqueous solution. The yeast added to this solution can then act on the
sugars

3.6
Fermentation is an exothermic process in which glucose (found in corn and sugar cane) is
broken down into ethanol and CO2 by the action of enzymes present in microbes such as
yeast or bacteria. The fermentation process is carried out as follows:-
- Simple sugars derived from plant material are mixed with yeast. The enzymes
produced by the yeast catalyse a complex series of biochemical reactions which
ultimately convert the reactants to glucose, then ethanol and carbon dioxide.
- This continues and CO2 escapes from the fermenting mixture. Fermentation stops
when alcohol level reaches 15% and the available sugars are metabolised.
Fermentation of glucose: C6H12O6 2CH3CH2OH + 2CO2

3.7
The molar heat of combustion of a substance is the heat liberated when one mole of the
substance undergoes complete combustion with oxygen at standard atmospheric pressure
with the final products being carbon dioxide gas and liquid water.

3.8
ETHANOL AS FUEL
ADVANTAGES
- it is a renewable resource and thus reduces the use of petrochemicals
- could reduce greenhouse gas emissions (if solar energy was used to distill it)
DISADVANTAGES
- large areas of agricultural land would need to be devoted to growing suitable
crops with consequent problems of soil erosion, salinity etc.
- disposal of large amounts of smelly waste, fermentation liquors after removal of
ethanol would pose major environmental problems.

3.9
Number of carbon atoms 1 2 3 4 5 6 7 8
Prefix meth eth prop but pent hex hept oct
4.1
Displacement of metals from solution (transfer of electrons):
- When an active metal is placed in a solution containing ions of a less active metal, the
active metal displaces the less active metal from solution (forming a solid)
- This occurs because a more active metal atom loses one or more electrons and
becomes a positive ion.
- The electrons lost are transferred to the ions of the less active metal, resulting in them
becoming metal atoms.
- Oxidation is loss of electrons (or gain in oxidation number- occurs at the anode)
- Reduction is gain of electrons (or loss in oxidation number- occurs at the cathode)
- Oxidation-reduction reactions are also called redox or electron transfer reactions.
- They can be written as half-equations.

4.2
The more reactive a metal is, the more likely it is to displace another from solution. In the
activity series, the more reactive (easily lose electrons) are towards the left, and least
reactive (hard to lose electrons) on the right. So a metal will displace another metal to the
right of it in the activity series.
Generally: REDUCTANT: and electron donor,
Active metals are strong reductants. causes an ion to be reduced.
Inactive metals are weak reductants. OXIDANT: an electron acceptor,
Cations of Inactive metals are strong oxidants. causes an ion to be oxidised.
Cations of Active metals are weak oxidants. REDUCTION: accepting of electrons.
(decrease in oxidation state)
OXIDATION: loss of electrons.
(increase in oxidation state)

4.3
Oxidation States: is the number given to an atom to indicate the number of electrons that
it has lost or gained.
Eg. Oxygen has an oxidation state of –II in most oxide compounds.
Hydrogen has an oxidation state of +I in most hydrogen compounds.

Metal and metal ions change their oxidation states during displacement reactions. Metals
are assigned a zero oxidation state. The oxidation state of a metal ion is equal to the
charge on the metal ion. During displacement reactions, metals increase their oxidation
states (oxidise) and metal ions decrease their oxidation states (reduce). The oxidation
number (ON) of an atom is the “charge” it would have if it occurred as an ion. ON’s are
written as roman numerals generally with a positive or negative sign.

Mg ( s ) −
→
2e
Mg (2aq+ ) + 2e −
ON = 0 ON = + II
Increase in oxidation number (0→+II): Oxidation.

Cu (2aq+ ) + 2e − +
→
2e
Cu ( s )
ON = + II ON = 0
Decrease in oxidation number (+II →0): Reduction
Oxidation State rules
1. Oxygen is -2 in a molecule
2. Hydrogen is +1 in a molecule (except hydrides)
3. Simple ions have the same oxidation number as the valency
4. Complex molecules add up to give zero.
5. The oxidation number of an element is zero

Changes in oxidation state result from a loss or gain of electrons. If given a number of
equations and asked which one is a redox reaction, look for a change in valency or an
element being formed or entering into a compound.

4.4

A galvanic cell is an ‘electron pump’. It causes the flow of electrons between atoms as a
result of redox reactions.
A galvanic cell is a device constructed so that a reductant and oxidant are physically
separated, but connected by an external circuit made of a conductor (to carry electrons)
and a salt bridge (to carry charged ions in solution). A galvanic cell is thus composed of
two half-cells, a reductant half-cell and an oxidant half-cell. This arrangement ensures
that electrons cannot go directly from the reductant to the oxidant, but they will move
through the external circuit.

4.5
NOTATOIN: Zn | Zn2+ || Cu2+ | Cu

Oxidation half cell Reduction half cell

Salt Bridge

4.6
ANODE: the electrode at which oxidation takes place. This electrode is negative in a
galvanic cell.
CATHODE: the electrode at which reduction takes place. This electrode is positive in a
galvanic cell.
ELECTRODE: the metallic conducting plates of a galvanic cell.
ELECTROLYTE: a substance which, in solution, conducts electricity because of its ionic
nature.

5.1
Difference between stable and radioactive isotopes:
A stable isotope of an element will not emit radiation, whilst a radioactive isotope will
emit radiation and decay. The emission of radiation will continue until the nucleus
becomes sable. Elements with atomic numbers greater than 83 are naturally radioactive.
The stability of an isotope depends on several factors:

Neutron to proton ratio is too high (excess neutrons):


When there are too many neutrons compared with protons then a neutron decays to form
a proton and a beta particle (a fast electron) which is emitted from the nucleus. This is
beta negative decay.
131 131 0
Example: 53I → 54Xe + –1e

Neutron to proton ratio is too low (excess protons):


When there are too many protons compared with neutrons then a proton decays to form a
neutron and a positron (same mass as an electron with a positive charge). This is beta
positive decay.
22 22 0
Example: 11Na → 10Ne + 1e

Too many nucleons (nucleus too heavy):


When there are too many nucleons then alpha decay occurs. The loss of an alpha particle
reduces the nucleus by 2 protons and 2 neutrons:
230 Th 226 4
Example: 90 → 88Ra + 2He

5.2
A transuranic element is an artificial element which has an atomic number greater than
92. At present there are 22 transuranic elements that have been made.
Some recently discovered (transuranic) elements (as below) were developed through the
process of alpha bombardment, as well as ion acceleration. Alpha Bombardment is the
process of firing alpha particles (helium nuclei) to produce new elements.
Some isotopes do not undergo fission (splitting the atom) when hit by neutrons. Instead
they absorb the neutron and thus create new elements. They can be created by
bombarding nuclei with neutrons (such as in nuclear reactors and particle accelerators).
Ion acceleration is based on the principle of firing (at velocities close to the speed of
light) accelerated particles into a target. An example of the process(s) used to produce a
transuranic element is as follows:
When U-238 is bombarded with neutrons it can be converted to U-239 that undergoes
beta decays to produce neptunium and plutonium.

Then Pu-239 is changed to americium by neutron bombardment.

Note: mass (the upper superscript numbers) is conserved as well as the charge (shown
by the lower subscript numbers) is conserved.

E.g.

5.3
There are 2 common methods that are used to make commercial radioisotope these
methods are:

1. Nuclear reactors – neutron bombardment. The nucleus of an atom, called the target
nucleus, is bombarded with various particles. These bombarding particles may become
incorporated within the target nucleus creating a new unstable nuclide or radioactive
isotope. E.g. cobalt-60, which is used in cancer treatment, is made by placing normal
cobalt-59 in a reactor where it captures a neutron.

2. Cyclotrons – bombardment of isotopes with a positive particle such as helium or


carbon.
14
N + 4He → 18F

ANSTO (Australian Nuclear Science and Technology Organisation) produces


commercial radioisotopes for use in industry, medicine and research. ANSTO operates
the research reactor called HIFAR (High Flux Australian Reactor) at Lucas Heights and
the National Medical Cyclotron. Neutron-rich radioisotopes are produced at the nuclear
reactor and neutron-deficient radioisotopes are produced in the cyclotron.
The HIFAR reactor has been designed to produce a source of neutrons rather than for the
generation of electricity. The fission of uranium-235 produces neutrons with which to
bombard the nuclei of stable elements. The sample to be irradiated is placed in the core of
the reactor where it absorbs neutrons and is transformed into a radioactive nuclide.
Technetium-99 is a widely used radioisotope produced in the reactor. Neutron deficient
`radioisotopes cannot be produced in a nuclear reactor but must be produced in a
cyclotron.

5.4
The instruments used to detect radiation include:

Photographic film (a dosimeter) – nuclear technicians wear sealed badges with


photographic film; the amount of radiation can be measured by the film darkening.
Geiger-Muller tube and counter – radiation causes argon atoms inside the GM tube to
become ionised. An electric pulse is created and detected.
Wilson cloud chamber – radiation ionises molecules which cause alcohol vapour to
condense to produce visible cloud ‘tracks’. The tracks are characteristic of the type of
radiation.
Scintillation counter - radiation causes some chemicals to give off flashes of light. The
flashes can be observed or recorded.

5.5
Cobalt-60 (INDUSTRY) Technetium-99m (MEDICINE)

Cobalt-60 is used for gamma Technetium-99m is used for diagnosis and


sterilisation of medical gamma photography of blood flow
products, wool and food disorders. It is also used to detect disease in
products. This radioisotope is organs such as the heart or brain.
used to sterilize objects that
would be damaged by heat
sterilisation.

5.6
Co-60 - Beams of radiation from Co-60 are directed at the object to be tested.
Radioactive film on the other side detects radiation when there are cracks or breaks.
Examining the film can help pinpoint structural problems.

It is used because it is a gamma emitter, and will penetrate metal parts. It has a half-life
of 5.3 years so it enables the equipment to have a long lifetime. It is also used in medicine
for cancer treatment, to kill cancer cells. It is used because the gamma rays it produces
emit enough energy to kill certain biological molecules, and has a suitable half life for
this purpose.

Tc-99m - Used for applications such as pinpointing brain tumours, by binding to


haemoglobin in red blood cells therefore allowing blood flow to be monitored through
out the body. Can be changed to a number of oxidation states which enables production
of a wide range of biologically active chemicals.

It is used because it has a very short half life (6 hours), therefore minimises exposure to
the body emits low energy gamma radiation which minimises tissue damage but can still
be detected; it is quickly eliminated from the body.