Vous êtes sur la page 1sur 11

om/)

(http://www.odinity.com)

StudentSweepstakes(http://www.odinity.com/chemistry/)

l.com/cgibin/webscr?cmd=_sxclick&hosted_button_id=LWUCKL4RKN72G)

Isolation of Caffeine from Tea


Leaves
OrganicChemistryLabs
(http://www.odinity.com/category/science/organic
chemistrylab/)
43433Views 2076Words

IsolationofCaffeinefromTeaLeaves
By:JuliaTrimble
Introduction:
Caffeineisanalkaloidstimulantwithacyclicbackbone
structureanalogoustothepurinestructuresofDNA,giving
ittheabilitytoaffectbiochemicalpathwaysinthebody1.In
commercialapplication,caffeinesupplements
pharmaceuticalsandcertainbeveragessuchascoffeeor
tea.Standardteabagscontain2.00+/0.05goftea
leavesalongwithapproximately55mgofcaffeine[1]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn1).

Usingtheproperextractionmethods,thecaffeinewithina
teabagcouldpotentiallybeisolatedtoyieldapuresolid
themassofthissolidwouldreflecttheactualyieldof
caffeineinthetea.Todoso,caffeinemustbeintroduced

toasolventthatisbothvolatileandinsolubletowatera
perfectexampleismethylenechloride[2]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn2).

Caffeinehasagreateraffinityformethylenechlorideand
willeasilydissolveinthissolventoverwaterhowever
caffeineisnottheonlyorganicsubstancefoundinteathat
iscapableofreactingwithmethylenechloride.Alongwith
caffeine,teabagscontainorganicsubstancescalled
tannins,orgallicacid1.Bothcaffeineandgallicacidare
capableofdissolvinginwaterhowever,caffeinehasa
strongerattractiontowaterduetothedipoledipole
interactionthatresultsfromthegreaterpolarityofcaffeine
andthehydrogenbondsthatformbetweencaffeineand
water1.Theoretically,theintermolecularforcesofgallic
acidcanbemanipulatedtoinduceastrongerdipoleion
interaction.Ifacommonsaltlikesodiumcarbonatewas
introducedtothesolution,gallicacidcouldrevertbackinto
phenolsalt:apolar,inorganicmoleculethatisinsolublein
methylenechloride[3]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn3).

Inmethylenechloride,caffeinewillhaveagreater
attractionfortheorganicsolventandthehydrogenbonds
betweencaffeineandwaterwillbebroken.Usinga
separatoryapparatus,twoinsolublesolutionscanbe
separated,isolatingcaffeineandthenewphenolanion
fromoneanother.Thedensermethylenechloridelayer
canthenbereleasedfromthefunneltorenderapure
solutionofcaffeineandmethylenechloride.Toensurethat
nowaterinterfereswiththeinteractionofcaffeineand
methylenechloride,sodiumsulfatecouldbeusedto
absorbanyexcesswaterthatmayhaveescapedfromthe

teasolution1.Ifheated,thesolventwouldquickly
evaporateduetolowboilingpointofmethylenechloride2.
Theremainingsolidwouldthenbepurecaffeine.
MaterialsandMethods:
Tostart,a150mLbeakercontaining50mLdeionized
waterand2boilingstoneswaspreparedtodissolve2.0
gramsofsodiumcarbonatetoreactwiththegallicacidin
tea.Thebeakerwasallowedtoheatuntilthewaterstarted
toboil,atwhichpointthetemperaturewasloweredand2
teabagswereplacedintothewater.Thesolutionwas
heatedfor10to12minutestoachievethehighest
concentrationoftea.Atthesametime,theinsoluble
cellulosecomponentsofteaseparatedfromthesolution
renderingtheteaconcentrate,caffeine,andthenew
phenolanionproduct.Thefinalsaturatedsolutionwas
pouredintoa100mLbeakerwhilethefluidstrappedwithin
theteabagsweresimultaneouslyrinsedwithanadditional
10mLofdeionizedwater.Oncecooled,thesolutionwas
transferredintoa125mLseparatoryapparatus,aglass
funnelusedtoseparateunmixablesolutions.Fromthetop
ofthefunnel,methylenechloridewaspouredintothe
solutioninincrementsof5mL.Followingeveryadditionof
methylenechloride,thefunnelwasinvertedtoreleasethe
builtuppressurefromthereaction.Thereactionrendered
browntoplayerofteaandaclearbottomlayerofdense
methylenechloride.Thebottomlayerwasreleasedfrom
thestopcockandcollectedintoa100mLbeakerleaving
behindathinlayerofmethylenechloridetoprevent
contamination.
Methylenechloridewasadded2moretimestoassurethat
allofthecaffeinewasreactedwith.Sodiumsulfatewas
addedtotheextractiontoabsorbanywaterthatescaped
fromtheteaandtheremainingfluidwasdecantedand
rinsedintoapreweighed50mLbeakerwithboilingstones

usinganadditional2.0mLofmethylenechloride.When
boiled,thevolatilemethylenechlorideevaporated,
renderingpure,solidcaffeine.[1]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn1),
[2]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn2),
[3]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn3)

DataSummary:

Experiment1:IsolationofCaffeinefromTeaLeaves

DensityofH2O

DensityofCH2Cl2

0.997

g/mL

1.32

g/mL

units

WeightofTeaBags

4.00

Weightof50mLbeakerandboilingstones

27.56

Weightof50mLbeaker,boilingstones,andcaffeine

27.58

WeightofCaffeine

0.02

TheoreticalYieldofCaffeine

0.11

ActualYieldofCaffeine

0.02

18.18

PercentYield

(http://www.odinity.com/wp
content/uploads/2014/03/NumericDataCaffeine
SpectrumGraph.png)
Figure3:ObtainedIRSpectrumGraphofCaffeine
Results:
ThepredeterminedmassesprovidedbytheLiptonTea
manufacturersareacceptedastheexperimental
measurementsofbothteaandcaffeine.Theapproximate
weightofanindividualLiptonteabagis2.000.05g,
containing55mgofcaffeineperbag.Inanexperiment
using2teabags,110mgistheexpectedyieldofcaffeine
toobtain.A50mLbeaker,alongwith2boilingstones,
wasweighedinadvancewithatotalmassof27.56g
duringtheextractionprocess.Toextractcaffeine,the
heatedteasolution,alongwith5mLofmethylenechloride,
waspouredintoanisolatedseparatoryfunnelandinverted
tomixthesolutioncompletely.Duetothereaction,
pressurebuiltupinsidethefunnel,requiringthestopcock
tobeopenedtoreleaseexcessgasfollowingeach
inversion.Oncesettled,thesolutionseparatedinto2
layers:thepolar,brownteasolutiononthetopandthe

nonpolar,clearmethylenechlorideonthebottom.Thetea
separatedabovethemethylenechloridebecausewhilethe
densityofwateris0.997g/mL,thedensityofmethylene
chlorideis1.32g/mL.Betweenthetwolayerssatsmall
bubblesorpossibleemulsionsthatrestrictedtheamountof
methylenechloridethatcouldbeextracted.Despitethis,
themethylenechloride/caffeinelayerwaseffectively
drainedintothepreweighed50mLbeakerandthe
processwasrepeated2additionaltimestoensurethatall
ofthecaffeinewasreactedwith.Indoingso,thevolatile
methylenechloridebegantoevaporateintothe
surroundingsduetotheincreasedroomtemperature.The
remainingsolutionwasheatedbrieflyuntilthevolatile
solventevaporated,leavingbehindsolidcaffeine.When
weighed,thebeaker,stones,andcaffeinerenderedatotal
massof27.58g.Thedifferenceinmassbetweenthe
initialweightofthebeakerandthefinalproductwasthen
theactualyieldofcaffeine,0.02g.Incomparisontothe
theoreticalmass,theexperimentprovided18.18%yieldof
caffeine.
ThesolidcaffeineproductwasrunthroughanInfrared
Spectrometerthatusesbondenergiestoidentifychemical
compounds.Thespectrometerproducedagraphbased
onmeasurementsofphotonenergywithinafrequency
rangebetween400and4000Hz.Individualspikesonthe
graphindicatetheuniquebondenergiesofcertain
functionalgroups.Forexample,thephotonenergyspike
visiblearoundthe3000Hzfrequencyrepresentsamine
andamidegroupapparentincaffeine.Theotherimportant
spikeappearsaround1600Hzand1750Hz.Thisspike
representsthealkeneportionofthecaffeinemolecule.
Usingtheseindividualspikesinphotonenergy,theinfrared
spectrometerpredictsthecompositionofthecompound
present.Thespectrometerpredictedtheprobabilitythat
thesampleproducedwascaffeinetobe869outof1000.
Thisvaluehasnorelationtothepurityofcaffeine.

Discussion:
Asisexpected,thepercentyieldofcaffeinewasnot100%
however,achievingthisgoalisimpossible.Themassof
caffeinefrom2Liptonteabagswasonly18.18%ofthe
theoreticalyieldbutinconsiderationofallthefactors
responsibleforerror,18.18%isanacceptablevalue.The
errorinyieldresultsfromanumberofunavoidable
experimentalflaws.Thefirstflaworiginatesfromthe
reactionbetweengallicacidandsodiumcarbonate.
Althoughtheconversionofgallicacidisnecessaryforthe
reactionofcaffeineandmethylenechloridetooccur,the
phenolanionbyproductofthisreactionisresponsiblefor
necessaryerror[1]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn1).

Whenphenolicacidsarerevertedbackintosalts,anionic
surfactantsareproduced4.Thesesurfactantsare
responsibleforemulsifyingwaterinsolublematerialslike
methylenechloride.Asaresult,largesoapybubbles
calledemulsionsareproducedbythepolarandnonpolar
solutions.Duringtheextractionphaseofthisexperiment,
thesebubblesrestrictedtheamountofcaffeinereleased
fromtheseparatoryfunnelresultinginalesseryield.
Anothersourceoflesseryieldoriginatedfromtechniques
usedtopreventthecontaminationofthemethylene
chloridesolution.Whileextractingthecaffeine,asmall
layerofmethylenechlorideneededtobeleftbehindto
avoidtaintingthefinalproduct[2]
(file:///C:/Users/jpapst.UAD/Desktop/New%20folder/Experiment%201.docx#_ftn2).

Bydiscardingpartofthemethylenechloridesolution,a
portionofthecaffeinewasleftbehindthataffectedthe
overallyieldoftheproduct.Thefinalsourceoferror
originatesfromunpreventableenvironmentalconditions.
Asaresultofthehotplatesusedpriortothecaffeine
extractionphase,thetemperatureofthelaboratorywas
increased.Methylenechloridedoesnotusuallyevaporate
atroomtemperaturebutbeingoutintheopenatan

increasedtemperaturetriggeredthesolutiontoreactearly
onleavinglessmethylenechloridetoreactwiththe
caffeine.Thiswouldresultinalesseramountofcaffeine
extractedfromthesolutionandalesseryield.

Questions:
1.Lookupthestructureofcaffeineanddeterminethe
strongestintermolecularforcepresent.
Thestrongestintermolecularforceincaffeineisthedipole
dipoleinteractionbecauseofthepolarityofthemolecule.
Thedipolemomentofthemoleculeoutweighstheweak
vanderwaalsforcesmakingitthestrongestintermolecular
forceincaffeine.

2.Whyiscaffeinemoresolubleinmethylene
chloridethaninwater?
Caffeineismoresolubleinmethylenechloridethanwater
becausebothcaffeineandmethylenechlorideareorganic
substanceswhilewaterisinorganic.Althoughcaffeineis
capableofdissolvinginwaterbyforminghydrogenbonds,
thegreateraffinitythatcaffeinehasformethylenechloride
breaksthesebonds.
3.Describethepurposeofaddingsodiumcarbonate
tothereactionmixture?

Thepurposeofaddingsodiumcarbonatetothemixture
wastoalterthechemicalstructureofgallicacid.Initially,
gallicacidhasaslightaffinityformethylenechloridethat
wouldconflictwiththereactionbetweencaffeineandthe
methylenesolvent.Byintroducingofabasicsatlike
sodiumcarbonatetothesolution,gallicacidwillbe
convertedintoaninorganic,phenolsaltthatisinsolublein
methylenechloridebuthighlysolubleinwater.Asaresult,
methylenechlorideextractwillcontainthehighestyieldof
caffeinealone.
WorkCited
Bettelheim,F.andLandsberg,J.Laboratoryexperiments
fororganicandbiochemistry.SaundersCollege
Publishing,107111,1995.
Clark,J.(2000).InterpretingInfraredSpectra.Retrieved
fromChemguide:
http://www.chemguide.co.uk/analysis/ir/interpret.html>
Experiment6:Isolationofcaffeinefromtealeaves.
(n.d.).SUNYOneonta.RetrievedFebruary2,2014,
fromhttp://employees.oneonta.edu/knauerbr/ch
Gensler,W.J.,Griffing,S.F.,andMohr,S.C.Fundamentals
ofOrganicandBiologicalChemistryLaboratory
Manual.PrenticeHallPublishing,249254,1994.
Landgrebe,J.A.,TheoryandPracticeintheOrganic
Laboratory.3rdedition,D.C.HealthandCompany,452
255,1982.
Stoker,H.S.(2013).OrganicandBiological
Chemistry.Belmont:MaryFinch.
Swartz,D.(2014,January).Experiment1:Isolationof
caffeinefromtealeaves.BioOrganicLab.Lecture
conductedfromDaemenCollege,Amherst,NY.

UniversityofColorado,Boulder,Chemistryand
BiochemistryDepartment.(2011).IR:carboxylicacids.
RetrievedfromIRSpectroscopyTutorial:
<http://orgchem.colorado.edu/Spectroscopy/irtutor/carbacidsir.html>

Home(http://www.odinity.com/) Contact(http://www.odinity.com/contact/)
SiteMap(http://www.odinity.com/sitemap/)
PrivacyPolicy(http://www.odinity.com/privacypolicy/)
Terms&Conditions(http://www.odinity.com/termsconditions/)
Copyright2014Odinity.com

(http://www.twitter.com/odinity)
(http://facebook.com/odinity)
()

Vous aimerez peut-être aussi