PaperChromatographyasaToolto

IdentifyInkBrands
SamanthaGalla
February19,2015
Partners:JoshCrowder,YiningDong,andElizabethFlaherty
Chem113Section#003
TA:ElizabethCrowe

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Introduction
Paperchromatographyisaprocessthroughwhichchemicalsareseparatedintoindividual
1
componentsbasedontheirrelativepolarity.
Thisprocessisusedinanalyticchemistryto

understandthechemicalmakeupofmixtures.Itisusefulespeciallyfortheseparationand
1
analysisofpigmentedsamples.

Therearetwocomponentstopaperchromatography,astationaryphaseandamobile
phase.Thestationaryphaseiscomposedofaporouspaper,whilethemobilephaseconsistsofa
1
fluidthatisabletoflowthroughthepaperthroughcapillaryaction.
Averysmallsampleofa

chemicalmixtureisplacedonthestationaryphase.Whenthetipofthestationaryphaseclosest
tothesampleisplacedinthemobilephase,thevariouscomponentsofamixturearepulled
1
throughthestationaryphaseindistancesrelativetotheiraffinitytothestationaryphase.
Once

thesamplesareseparated,theycanthenbeidentifiedthroughvariousobservationssuchas
pigmentandR
value.
f
TheunderlyingprinciplesofchromatographycanbetracedbacktoPlinytheElder,who
2
usedaprocesssimilartopaperchromatographyforthedetectionofferroussulfur.
However,the

processofchromatographywasfirstutilizedintheearly1900sbyMikhailTswett.Inaneffortto
extracttheredandyellowpigmentsfromgreenleaves,Tswettcrushedleavesintoasolutionand
mixeditwithapowder.Hethendiscoveredthatdifferentcolorswereabsorbedbythepowderto
3
differentdegrees.
Thetechniquewasntpopularizeduntilthelate1930sthroughtheworkofthe

Englishscientists,Martin,Consden,Gordon,andSynge.Thesemenusedtheprocessthey
2
referredtoaspartitionchromatographytounderstandtheproteinstructureofwool.

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Theprocessworksinthankstotheideaoflikepolaritiesattracteachother.Polarityisa
4
measureofthedegreeofseparationofchargewithinamolecule.
Thepolarityofamoleculeis

determinedbythecompositionandconformationofsaidmolecule.Ingeneral,moleculeswitha
4
greaterquantityofpolarbondsaremorepolar.
Apolarbondisdefinedasacovalentbond

betweentwoatomsofdifferentelectronegativities,whichcreatesaslightseparationofcharge
betweenthetwoatoms.
Thepaper,madeupofpolymerchainsofglucose,ispolar.Thisisduetothealcohol
3
(OH)groupsontheedgeoftheglucosemolecules.
Thispaperattractswatervaporfromtheair,

andformsathinlayerofwateronthesurfaceofthepaper.Themobilephaseisusuallya
relativelynonpolarsolvent.Whenthepaperisplacedinthemobilephase,thesenonpolar
5
moleculeswilleasilymoveupthepolarpaperthroughcapillaryaction.

Thesampleismadeupofvariouschemicals,eachwiththeirownuniquepolarity.
Componentswithhigherpolaritywillbemoreattractedtothepolarpaper,whilecomponents
5
withlowerpolaritywillbemoreattractedtothenonpolarsolvent.
Therefore,highlypolar

moleculeswillinessencebestuckonthepolarpaper,andwillnottravelveryfarupwards.
Nonpolarmoleculeswillhavestrongaffinityforthenonpolarsolvent,andwilltravelveryfar
upthepaper.Whenthesolventtravelsupthepaper,itwillpullthevariouscomponentsofa
mixtureupthatpapertovaryingdegrees.Theendresult,isaseparationofcomponentsinto
distinctlayers.
Thistechniqueisusefulforpigmentedmixturesmadeupofcomponentswithdifferent
1
polarities.
Someadvantagesofthistechniqueisthesmallsamplesizerequiredandtheabilityto
3
testmultiplesamplesonthesamestrip.
Themostusefulapplicationofthismethodisinforensic

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6
work.
Thisisbecausesamplesareoftenverysmallinsize,andcancontainavarietyoforganic

andnonorganicmaterials.
Othertypesofmethodsusedininkidentification,includevisualassessmentsandthin
layerchromatography.Theformerincludesanalysisunderinfraredandultravioletlight,along
7
withtestsofluminicity.
Thelatterisanotherformofchromatography,whichworksinasimilar
7
manneraspaperchromatography.

Themaingoalofthisprojectwastoidentifyfiveunknowninksamplesasoneoffifteen
3
penbrands.Theprocedureforthisexperimentwasadaptedfromtheliteratureprocedure.

Identificationwasachievedmainlythroughtheuseofpaperchromatography,howeverother
qualitativeobservationswereusedintheidentificationprocess.Thereweretwomainstepsinthe
identificationprocess.Firstallfifteensampleswereanalyzedthroughtheprocesspaper
chromatographywithvaryingmobilephases.Thenoncethemosteffectivemobilephaseswere
selectedfromthoseresultsandusedtotestthefiveunknownsamples.Theseresultswere
comparedandmatchedwiththebrandstheymostcloselyresembled.
Itwashypothesizedthatapolarmobilephasesuchaswaterwouldbebestforanalyzing
andidentifyingtheunknownpendyes,duetoitshighlypolarnature.Thishypothesiswasnot
madeuntiltheinitialsetoftests,involvingachromatogramdonewiththenonpolarmobile
phaseofisopropylalcohol.Therefore,itwasthoughtthatadramaticincreaseinpolarityofthe
solventwasrequiredforaneffectivechromatogram.

Procedure
8
Theprocedure
isasfollows:

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1. Firsta18cmx5cmpieceofchromatographypaperwasacquired.Astraightline
acrossthelengthofthepaperwasdrawnwithapencil,approximately5cmfrom
thebottom.Thenthatlinewasmarkedin1cmincrements.
2. Oncethepaperwasmarked,fifteeninksampleswereplacedonthepaper,along
theline.Onesamplewasplacedateachcentimetermark.Foreachsample,five
smallcirclesweremadewitheachpen,creatingonesolidcoloreddot.This
ensuredsimilarsamplesizesforeachinkbrand.
3. Atthisstage,thecolorandsaturationofeachpeninkwasrecorded.Theseresults
willlaterbecomparedwiththefiveunknownsamples,toaidinidentification.
4. Themobilephasewaspreparedbyaddingtwopipettefullof100%isopropyl
alcoholtoapetridish.
5. Thestationaryphasewasstapledtogethertoformastandingcircle,thengently
placedinthemobilephase.Aplasticcupwasimmediatelyplacedoverthe
stationaryphaseandtheapparatuswasleftundisturbedforfifteenminutes.
6. Oncethemobilephasewasapproximatelyfivecentimetersfromthetopofthe
stationaryphase,thepaperwasremovedfromthepetridish.
7. Thesolventfrontwasimmediatelymarkedwithapencil,andthepaperwaslaid
outtodry.
8. Oncethepaperwasdry,apencilwasusedtomarktheseparationofeachdye,and
theapproximatecenteroftheconcentrationofthedye.Thatdistancewas
recorded,alongwiththedistanceofthesolventfront,andtheresultswere
recorded.Theseresultswerereferredtowhenidentifyingthefiveunknowns.

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9. ThechromatogramwasthenplacedunderaUVlampandobservationsofeach
inksreactionundersuchconditionswerealsorecorded.
10. Steps1,2and48wererepeatedthreemoretimeswithvaryingmobilephases.
Thefollowingmobilephaseswereselected:distilledwater,methanol,andethyl
alcohol.
11. Steps310wererepeated,thistimewiththepremadesampleofthefiveunknown
peninks.Thesolventusedwasethylalcoholinsteadofisopropylalcohol.
12. Steps48wererepeatedwithanotherpremadesampleofthefiveunknowns.The
solventusedwasmethanolinsteadofethylalcohol.
Equipment/materialsused:
118cmx5cmpieceofchromatographypaper
1pencil
1ruler
5differentbrandsofpen,eachinthecolorsred,blue,andblack:
Pilot
Bic
PilotEasyTouch
VBall
Papermate
1pipette
100%isopropylalcohol
1petridish

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1clearplasticcup
1stapler
1UVlamp
distilledwater
ethylalcohol
methanol
Eachinksamplewasassignedanumberasfollowed:
8
Table1.AssignedNumberofFifteenKnownPenInks

Number

Brand

Color

Pilot

Blue

Bic

Blue

PilotEasyTouch

Blue

VBall

Blue

Papermate

Blue

Pilot

Red

Bic

Red

Papermate

Red

PilotEasyTouch

Red

10

VBall

Red

11

Bic

Black

12

Papermate

Black

13

PilotEasyTouch

Black

14

VBall

Black

15

Pilot

Black

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Results
Theresultsfromeachtestchromatogramareshownbelow.

8
Figure1.ChromatogramofPenInkswithIsopropylAlcohol

Inkseparationwiththeisopropylalcoholwasnotveryapparent.Thereisonlyonetypeof
dyeidentifiedforeachsample.TheexactR
valueswerehardtocalculate,sincemostofthedyes
f
appearaslongtransparentstreaks,ratherthanopaquelayers.Manyofthesamplesalsogave
similarresults.Samples11and12areindistinguishablefromeachotherasaresamples6and10.
Thiswouldmakeittoodifficulttoidentifyoneoftheunknownsasanyoneofthesebrands.
Overall,isopropylalcoholmadeapoormobilephasefortheinksamples.

9
Figure2.ChromatogramofPenInkswithMethanol

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Methanolprovidedverygoodseparationoftheinksamples.Almostallofthesamples
providedatleasttwodistinctlayersofdye.Additionally,theoutlinesofmostofthedyesamples
aredistinctlyvisible.Samples4and10createdespeciallydistinctdyeseparations.However
samples7,8,and9wouldbeverydifficulttodistinguishfromoneanother.Overall,methanol
provedafairlydecentmobilephase.

10
Figure3.ChromatogramofPenInkswithDistilledWater

Waterwasbyfartheworstmobilephasetested.Lessthanhalfofallsamplesprovided
anyseparationatall,andnoneofthemhaddistinctlayersformed.Samples14and15were
nearlyidentical,whilesamples1and4werealsosimilar.Overallthiswouldnotbeaneffective
solventforidentifyingtheunknownsamples.

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8
Figure4.ChromatogramwithEthylAlcohol

Ethylalcoholprovidedverygoodseparationforthesamples.Thereareatleasttwo
distinctlayersofdyeforalmostallofthesamples,andtheirrespectiveR
valueswereeasily
f
calculated.Mostofthecolorswerebrightandeasilydistinguishedfromoneanother.Theonly
samplesthatlooksimilarwere6and10and11and12.Overall,itwasdecidedthatethylalcohol
wasthebestmobilephase,ofalltheonestested.Thiswillbetheprimaryagentusedto
determinetheunknowns.ThereforetheR
valuesforeachsamplewasdetermined,andislisted
f
below.

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8
Table2.R
ValuesofFifteenKnownSampleswithEthylAlcoholasMobilePhase
f

Sample#

R
Values
f

SolventFront

N/A

0.89

0.08

0.18

0.97

0.52

0.32

0.18

0.08

0.63

10

0.92

0.05

11

12

13

0.95

14

0.95

0.76

0.13

15

0.05

Inadditiontothechromatograms,therewereotherobservationsmadeabouteachsample.
includingqualitativedescriptionoftheinksonpaper,andtheappearanceofeachdyeundera
UVlight.Thesecharacteristicsarelistedbelow.

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8
Table3.AdditionObservationsofFifteenKnownPenInks

SampleNumber

DescriptionofInk

ChangeUnderUVLight

saturated,blue

no

unsaturated,blue/purple

no

unsaturated,blue

no

saturated,blue/purple

no

saturated,darkblue

no

saturated,red

yes,glowsneonyellow

unsaturated,red/purple

yes,glowsneonyellow

unsaturated,red/purple

yes,glowsneonyellow

unsaturated,lightred

yes,glowsneonyellow

10

saturated,red

yes,glowsneonyellow

11

unsaturated,black

no

12

unsaturated,black/blue

yes,glowsslightlyyellow

13

unsaturated,black

no

14

saturated,black

no

15

saturated,black/purple

yes,glowsslightlyyellow

Thedistinctionbetweensaturatedandunsaturatedcolors,wasbaseduponwhetherornot

anywhitespacewasseeninthedot.Saturatedcolorsweredarkermorevibrantanddidnotlet
anywhitespaceshowthrough.Unsaturatedcolorswereduller,andsomewhitespacecanbe
seeninthedot.Thedifferenceincolorweremoresubtleandinexact.Itwouldbehardtoidentify
anunknowninkbasedonthecoloralone.TheappearanceunderUVisextremelyusefulfor

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furtherdistinguishingtheblackinks,ashalfglowandtheotherhalfdont.Howeveritisnot
usefulindifferentiatingtheblueortheredinkbrands,asthealllookthesameunderUVlight.
Givenallofthisinformation,afinalprocedureforidentifyingthe5unknownswas
created.Threemainobservationsweretakeninanefforttoascertaineachsamplesidentity.First,
theappearanceofeachwasrecorded.Thiswouldnarrowdownthepossibilitiestoonlythefive
brandswithinonecolor,andmayprovidefurtherevidenceforanyonebrand.Thena
chromatogramofthesamplewastakenwithethylalcoholasthemobilephase.Ethylalcoholwas
selected,duetoitsabilitytoseparateinksintodistinctlayers,andtheoveralldistinctnatureof
eachsample.

8
Figure5.ChromatogramofFiveUnknownswithEthylAlcohol

Additionally,asecondchromatogramwascreatedwithmethanol.Thiswastestedfor
qualitativereasons,asmethanolprovidedbetterspreadofsamplenumber3.Totherightofthe
fiveunknownsamples,twoadditionalinksamplescanbeseen.Theseareatestofink6and10.
Theywereplacedinordertocomparethemdirectlyunknown3.Theunknownhadthesame
brightyellowlayeratthebottomofthechromatogramassample10.Itwasdeterminedfromthis

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chromatogram,thatunknown3lookedmostsimilarto10.

8
Figure6.ChromatogramofFiveUnknownswithMethanol

FinallythesamplewasplacedunderUVlightandanyglowingwasrecorded.Theresults
ofthesetestsareshownbelow.Thenumbersinparenthesisindicateswhichsampleeachresult
mostcloselymatched.ThereferenceforthenumbersinparenthesiscanbefoundinTable1.
8
Table4.Appearance,R
Value,andUVResultsofFiveUnknownPenInks
f

Fromthisdata,thefiveunknownswerecorrectlyidentifiedas:
1. BlackBic(11)
2. BlackVBall(14)

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3. RedVBall(10)
4. RedPapermate(8)
5. BluePilot(1)

Discussion
Therewereseveralchangesmadetotheinitialprocedure.Initiallytheisopropylalcohol
wasfoundtobeapoormobilephaseforseparatingandidentifyingtheinks.Nodistinctlayers
werefoundforeachink,anditwasdifficulttomeasuretheR
fvalues.Itwasbelievedthatthis
f
wasduetotherelativelowpolarityofthesolvent.Therefore,itwashypothesisedthatamobile
phasewithahigherpolarity,suchaswater,wouldprovetobeabettersolvent.Threeadditional
mobilephasesweretested,eachwithvaryingpolarities.
11
Water,withapolarityof9.0
wasfoundtobeanevenworsemobilephasethan

isopropylalcohol.Lessthanhalfoftheinkstestedshowedanyspreadofatall,andthosethatdid
spread,didnotshowlayersorcontaindistinctR
values.Furtherresearchrevealsthatthisisdue
f
5
tothefactthatthereisalmostnodifferenceinpolaritybetweenwaterandthepaper
,therefore

theinkswouldnotshowstrongpreferenceforonephaseovertheother.
11
Methanolwithapolarityof5.0
provedamuchbettermobilephasethaneitherisopropyl

alcoholorwater.Thisdidprovidedistinctlayersinmanyoftheinkstested,andprovidedreliable
R
valuesformanyofthesamples.Someshortcomingsofthissolventarethedifficultyin
f
differentiatingcertaininksfromoneanother.
11
Finallyethylalcohol,withapolarityof5.1
wasthebestmobilephaseofalltested.It

providedseparationofallinkbrandsandprovideddistinctspreadsforinksthatwereunclear

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withmethanol.However,itdidshowsimilarresultsfordifferentinksthanthemethanol.Thatis
whybothethylalcoholandmethanolwereusedtotesttheunknowns.
TheR
valuesfromtheethylalcoholchromatogramwasusedtoidentifythebrandof
f
unknowns1,2,4,and5.Thephysicalappearancefromthemethanolchromatogramhelped
determinethebrandofunknow3.
Otherchangesmadetotheoriginalprocedurewerethetwoadditionalobservationsmade.
Thefirstobservationwasthecolorandsaturationoftheinkbeforegoingthroughpaper
chromatography.Thisobservationwasnotenoughtodistinguishoneinkbrandfromanother.
However,itdidmakeacaseforonebrandoveranotherwhenR
valuesweresimilartomultiple
f
brands.Thiswasnotaprimarymethodofidentification,butwassimplyawaytofurther
distinguishtheunknownsthathadR
valuesthatcouldmatchmorethanonesample.
f
Thiswashelpfulinthecaseofunknown3,astheR
valuewassimilartothatoftwo
f
samples.Thedifferenceinappearanceiswhatcausedonebrandtobechosenovertheother.
Howeverthesepredictionswereentirelyunhelpfulforunknown5,asitsphysicalappearance
didnotmatchedtheR
valuesthatresulted.Inthiscase,theguesswasbasedontheR
valueover
f
f
theappearance.Appearancehadnoeffectontheguessforunknowns1and2.Howevertheydid
supportthefindingsfromtheR
values.Inthecaseofunknown4,physicalappearancewasa
f
betterindicationofbrandthanR
value.
f
Thisadditiontotheprocedurehelpedrefinetheguessesforallbutoneoftheunknowns.
Itwasaddedbecauseitwasasimpleobservationtomake,andhelpednarrowdownthechoices,
usuallyfrom15possibilitiestotwoorthree.

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TheadditionalobservationmadewastheappearanceofchromatogramsunderaUVlight.
Thiswasonlyusefulfordeterminingthebrandoftheblackunknowns.Noneoftheblueinks
glowedunderUVlight,andalloftheredsglowedequallybrightlyunderUVlight.However,
onlytwooftheblackinksglowedunderUVlight.Thisprovedcrucialtodeterminingthebrand
ofunknown1,astheR
valuewasaclosematchtotwodifferentbrands.
f
Thisadditionwasmadebecauseitwaseasytomeasure,anditprovidedsomewayto
furtherdistinguishbetweenunknownsthathadR
valuessimilartomorethanonepossible
f
brand.
Allofthesechangestotheprocedurestrengthenedtheargumentfortheidentityofeach
unknown.Withoutthechangeinmobilephasefromisopropylalcoholtoethylalcohol,itis
unlikelythatanyofofunknownswouldhavebeenproperlyidentifiedwithanykindofcertainty.
Additionally,ifonlyonechromatogramoftheunknownswasmadewithoutthethreeadditions,
onlytheidentityofunknown2couldhavebeendeterminedwithadegreeofconfidence.Overall
alloftheseobservationsputtogetherleadtofivepredictionswithstrongevidenceinsupportof
each.
Theinitialhypothesiswaspartiallycorrect.Amorepolarsolventdidseparatetheinksto
abetterdegree.However,thiswasonlytrueuptoapoint,andwascompletelyuntrueinthecase
ofwater.Giventheresults,itappearsthatamobilephasewithapolarityaround5.2wasmost
effectiveatseparatingthedyes.
Thefinalprocedureusedtoidentifythefiveunknownsisasfollows:
1. Observeandrecordtheappearanceofeachunknownbeforetakingthechromatogram.
Takenoteespeciallyofthecolorandsaturationofeachsample.

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2. Takeachromatogramofthefiveunknownswithethylalcoholasamobilephase.
DetermineandrecordtheR
values.
f
3. ObservethecompletedchromatogramunderaUVlightandrecordobservations.Take
noteoftheappearanceanddegreeofglow.
4. Takeonefinalchromatogramofthefivesamplesinmethanol.R
valuesneednotbe
f
taken.Observeappearanceofresults.
Usingthisprocedure,itwasfoundthatallfiveunknownsweresuccessfullyidentified.

Conclusion
Theprimarygoalofthisexperimentwastoidentifyfiveunknowninkbrandsasoneof
fifteengivenbrands.Thisgoalwasachievedthroughtherefinementofagivenprocedureusedto
takeachromatogramofinksamples.Inthisprocess,therewereseveralfindingsthataidedinthe
finalidentification,andprovidedgreaterinsightintothequalitiesoftheseinksand
chromatographyasawhole.
Themostsignificantfindingwastheproperidentificationofthefiveunknowns.Asstated
intheresultssection,allfiveunknowninksampleswerecorrectlyidentified.
Anothersignificantfindingwastheprocessthroughwhichtheinkswereidentified.In
thisprocess,additionalobservationsweremadethathelpedsupporttheresultsfromthe
chromatograms.
Simplynotingthephysicalappearanceoftheinkwasfoundtobegreattoolinidentifying
theunknowns.Forfourofthefivecases,theunknownwascorrectlyidentifiedbasedonphysical
appearancealone.Inoneofthosecases,physicalappearancewasmorehelpfulindetermining

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theunknownthanthechromatogram.However,itshouldbenotedthatthereweremultiple
guessesthatmatchedeachunknown.Thereforeadditionalobservationsmustbemadeinorderto
furthernarrowdownthepossibilities.
TheadditionofobservationsmadeunderUVlightingwasfoundtoonlybeusefulinthe
caseofblackinks.Thisprovidedthemainevidencefortheidentificationofoneofthe
unknowns,andsupportedtheevidenceforanother.Themainbenefittothistest,isthesimple
distinctionbetweeninksthatglowunderUVandthosethatdont.Whereastheothertwotest
gaveresultsthatfellonaspectrum,thatcouldmatchmultipledifferentresults,theseresultswere
definitive.
ThefinaltoolusedforidentifyingtheunknownswastheR
valuesfromachromatogram
f
madewithethylalcoholmobilephase.R
valuescorrectlyidentifiedfourofthefiveunknowns.
f
However,itonlyprovidedonedefinitivepossibilityfortwoofthem.Thisprovedusefulforthe
quantitativenatureoftheresults.Assigningnumericalvaluestotheresultsmadeiteasierto
distinguishsmalldifferences.
Aninitialhypothesiswasmadethatamobilephasewithahighpolaritysuchaswater
wouldbestseparatethepeninks.However,itwasfoundthatethylalcoholisthebestmobile
phasefortheseparationofinkdyes.Methanolalsoproveduseful.Bothofthesehadapolarity
near5.Therefore,ingeneral,othermobilephaseswithsimilarpolaritiesshouldalsomakegood
mobilephases.Waterwithapolarityof9.0provedtobeuselessintheseparationand
identificationofpeninks.Isopropylalcohol,withapolarityof3.2,alsomadeapoormobile
phase,inthiscaseduetoitsrelativelowpolarity.

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Forfuturestudies,furtherrefinementtothephysicaldescriptionscanbemade.This
techniqueprovedvaluableinidentifyingunknowninksamples.However,thedescriptorsused
werevagueandinexact.Refiningthevocabularyused,orevenfindingquantitativewaysto
indicatethesecharacteristicscouldeliminatetheneedforchromatogramsatall.Additionally,
moresolventscouldbetestedasmobilephases.Solventswithpolaritiesabove3.2and9.0
shouldbetested,withafocusonsolventswithapolarityaround5.2.Thissameprocedurecould
alsobetestedwithawidervarietyofpenbrands,totestitseffectivenessoverlargerscopes.

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