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SynthesisofAspirin

MissPerfect*,LabPartner
DepartmentofChemistry,LosAngelesHarborCollege

Abstract
Aspirin(acetylsalicylicacid)isproducedexperimentallyinthelab.Theresultingpercentyieldis63.4%.Thepurity
oftheproductistestedusingthemeltingpointandbycomparisonwithotheraspirinandsalicylicacidproductsof
knownpurity.Theproductistooimpureforhumanconsumption.
Introduction
Aspirinisadrugcommonlyusedtotreatmildtomoderatepain.Inthisexperiment,aspirinwassynthesizedfrom
salicylicacid(C
7
H
6
O
3
)andaceticanhydride(C
4
H
6
O
3
)andthentestedforpurityintwodifferentways.Ifthe
experimentalaspirinispure,itshouldhaveadefinitemeltingpointthatisveryclosetothemeltingpointofacetyl
salicylicacidfromreferencesources.Whentestedforpuritybycomparison,theexperimentalaspirinshould
producethesamereactionwithferricammoniumsulfateas0.15%salicylicacidoranoverthecounteraspirin
purchasedfromadrugstorewheneitherismixedwiththesamereactant.0.15%salicylicacidisthemaximum
allowablepercentageofsalicylicacidinaspirinforhumanconsumptionasdeterminedbytheUnitedStates
Pharmacopoeia,16
th
edition.
Procedure
SeePreLab.
Results
PartI: SynthesisofAspirinandMeltingPoint
A. InitialMeasurements
1. MassErlenmeyerflask: 37.62g0.01g
2. Massflask+salicylicacid: 39.89g0.01g
3. Masssalicylicacid: (39.89g)(37.62g)=2.27g
4. Watchglass+weighpaper+filter: 25.8809g0.0001g
B. Datafromreferenceresources
1. Densityaceticanhydride: 1.0820g/cm
3

2. MeltingPointAspirin: 137C
C. Measurementsaftersynthesisofaspirin:
1. Massaspirin+watchglass+papers: 27.7562g0.0001g
2. Massaspirin(actualyield): (27.7562g)(25.8809g)=1.8753g
D. Balancedchemicalequationandcalculations
1. C
7
H
6
O
3
(s)+C
4
H
6
O
3
(l)C
9
H
8
O
4
(s)+C
2
H
4
O
2
(l)
2. 2.27gC
7
H
6
O
3x
1 moI
138.13 g
x
1 moI C9H8O4
1 moI C7H6O3
x
180.17 g
1 moI
= 2.96 gC
9
H
8
O
4
(theoreticalyield)
3. (1.8753g)/(2.96g)x100%=63.4%yield
E. Experimentalmeltingpoint:
1. Aspirinbeginstomelt: 119.9C
2. Aspirinfinalmelt: 130.4C
SynthesisofAspirin
PartII: AspirinPuritybyComparison
A. Samples+FeNH
4
(SO
4
)
2

1. Labaspirin+FeNH
4
(SO
4
)
2
: translucentdarkpurpleliquid
2. OTCaspirin+FeNH
4
(SO
4
)
2
: translucentpalelavenderliquid
3. .15%salicylicacid+FeNH
4
(SO
4
)
2
: clear,translucentorangeyellowliquid
Discussion
Theprocedureforthesynthesisofaspirinwasrelativelysimple,althoughconsistedofmanysteps.Thegreatest
sourceoferrorduringtheprocedurearisesfromthefactthatthereactantsandproductsaretransferredbetween
containersmultipletimes.Anothersourceoferrorisensuringthatthereactantshavereactedascompletelyas
possible.MycolleagueandIwereabletoproducea63.4%yield.Asforthepurityoftheproduct,nexttimeIhave
aheadacheIwillhappilypurchasemyaspirinatthepharmacyratherthancooksomeupinmykitchen.Thelab
aspirinproducedmeltedbetween119.9Cand130.4C.Comparedtothemeltingpointofaspirinfromreference,
137C,andtakingintoaccounttheratherbroadrangeinwhichitmelted,theseresultssuggestaratherimpure
product.Thecomparativepuritytestsupportedthesefindings.Ourexperimentalaspirinproducedamuchdarker
colorthantheoverthecounteraspirin;evidencethatthereisamuchgreateramountofsalicylicacidstillpresent
inthelabproduct.Thetruetestshouldhavebeenthe0.15%(industrystandardsafeforingestion)salicylicacid
solution;however,thesolutionappearedtocontainnoactualsalicylicacidastheresultingcolorwhenmixedwith
ferricammoniumsulfatewasorangeyellowasopposedtotheexpectedshadeofpurple.
References
DensityofAceticAnhydride.CRCHandbookofChemistryandPhysics:AReadyReferenceBookofChemicaland
PhysicalData.82
nd
ed.2001.
AcetylsalicylicAcid.ChemicalLand21.com.n.dChemicalLand21.com08.Oct2007.
<http://www.chemicalland21.com/lifescience/phar/ACETYLSALICYLIC%20ACID.htm>.