Analysis of Aspirin1

Frederick R. Wight Manatee Community College

Introduction Acetylsalicyclic acid, aspirin, was synthesized from salicylic acid in CHM !"#$ %y the reaction in Figure &' Figure & Aspirin synthesis'
O O O OH H + O O CH3 CH3 O Salicylic Acid Acetic Anhydride Aspirin O CH3 Acetic Acid O O H + HC 3 O OH

Aspirin is not sta%le indefinitely and can, o(er time, react with moisture to re(ert %ack to salicylic acid %y a process known as hydrolysis, Figure . Figure ' Aspirin Hydrolysis
O OH O O CH3 O O OH OH

H2O

+ HC 3

OH

Aspirin

Salicylic Acid

Acetic Acid

)n this la%oratory we will analyze la% synthesized and commercial aspirin for purity %y %oth *ualitati(e and *uantitati(e methods. +ualitati(ely, the purity of an aspirin sample can %e determined from its melting point. +ualitati(e chemical analysis is concerned with identifying the elements and compounds present in a sample of matter. ,he melting point of a su%stance is essentially independent of atmospheric pressure, %ut it is always lowered %y the presence of impurities -recall colligati(e properties' freezing point depression and %oiling point ele(ation.. ,he degree of lowering of the melting point depends on the nature and concentration of the impurities. ,he term melting point is somewhat of a misnomer since su%stances rarely melt at a single temperature. Rather they melt o(er a range of temperatures and the smaller the temperature range the purer the su%stance. /ote also that e(en though
&

0artly adapted from a procedure %y 1er%er, Akhtar 2 3chneider, 34/5 3tony 6rook. 0arts of this la% ha(e %een taken from 7$a%oratory Manual for 0rinciples of 8eneral Chemistry9, :.A. 6eran

Aspirin 3ynthesis

&

. if the aspirin has a trace amount of salicylic acid the melting point of the mi.salicylic acid has a higher melting point than aspirin. +ualitati(ely.a%le &. comple.hus if our aspirin is contaminated with salicylic acid it will re*uire more /a=H to reach the endpoint than if our sample were &!!J pure aspirin." = ? H = ? H <= ? Aspirin does not form this comple.. # A standardized /a=H solution titrates the acid to the phenolphthalein endpoint.& &#E>&B!FC &. the purity of an aspirin sample can %e determined %y a simple acid>%ase titration.his means if we titrate the same weight of each su%stance it will take more /a=H to reach the endpoint with salicylic acid.#C !.C . Holume /a=H..he addition of acidified iron -))). ion produces the (iolet tetraa*uosalicylatroiron -))). +uantitati(ely. with acidified iron -))). $ . ion which is readily (isi%le at low concentrations. Molarity of /a=H. &!># ". 3alicylic acid forms a colored comple. . 6oth aspirin and salicylic acid are weak organic acids %ut with different properties.!E . %y titrating a known weight of our sample with a standard /a=H solution we can determine the 7effecti(e molar mass9 -KMM.a%le & Compound' Formula' Molar Mass' Melting point' 1a p1a 3olu%ility -gG&!!m$..ture will %e lower than pure aspirin. Figure <' . KMM I grams of sampleGmoles acid from titration 3alicylic Acid CCHB=< &<E.DD !. &!>< . . . Figure <. molG$ I mol /a=H I moles acid /ote that salicylic acid has a lower molar mass.&# &"!>&" FC .&E Aspirin CDHE=" &E!. )n fact.his forms the %asis for a simple *ualitati(e test for the presence of unreacted salicylic acid in your aspirin. it is also possi%le to detect the presence of salicylic acid using ferric chloride. where -&.B A C = = ?< = C = Fe-H =. . ? => > ? @Fe-H =. Aspirin 3ynthesis .

Procedure Part I &.& then the formula does not apply. Record the final %uret reading along with the e. C. Add &! m$ of D#J ethanol (Make sure you add this before the water!!) Add #! m$ of L) water Add drops of phenolphthalein indicator and swirl to dissol(e the aspirin Fill a clean #! m$ %uret with standardized !.<CD-KMM>&<E.& . . Record the o%ser(ations in your note%ook. <. salicylic acid and the la% synthesized aspirin in < separate test tu%es. Chloride solution to each and o%ser(e the color of each sample. E.imately <># drops of D#J ethanol to dissol(e the aspirin.& M /a=H Read the initial (olume 3lowly add the /a=H solution to the flask with the aspirin in it until the endpoint is reached -(ery light pink color. Add appro. Repeat the procedure a%o(e using the aspirin synthesized in CHM !"#$. 3how your instructor to (erify Weigh out this mass of pure aspirin and place it into a #! m$ Krlenmeyer flask.& M /a=H to reach the stoichiometric e*ui(alence point.hen add &> ml of water to each sample. &!. <. 0lace a few crystals of pure aspirin. D.&# or less than &<E. Part IIa &. . Add drops of )ron -))).& .G-&E!. B.act molarity of the %ase Repeat the titration. . I .& . #. ". then the percent composition can %e deri(ed from the KMM according to the relationship' J Aspirin I &!!-KMM>&<E. &. Part IIb Calculate the mass of pure aspirin that re*uires ! m$ of a !. Aspirin 3ynthesis < .)f the sample consists of =/$5 salicylic acid and aspirin.&#>&<E. )f the KMM is greater than &E!.

rial Aspirin 3ynthesis " .Data Sheet Part I Obser ations on addition of Iron(III)chloride 3alicylic acid'MMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMM 0ure aspirin'MMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMM $a% synthesized aspirin'MMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMMM Part IIa (Pure Aspirin) Calculate the mass of aspirin needed to reach the stoichiometric e*ui(alence point with ! m$ of a !. )nitial %uret reading -m$. -3how calculations %elow for &st run. . Final %uret reading -m$. A(erage J purity of aspirin -J. MMMMMMMMMMMM . Molarity of /a=H -molG$. . Holume of /a=H used -m$.& M /a=H solution. -3how calculation %elow. MMMMMMMMMMMM 0ercent purity of aspirin -J.rial & Mass of aspirin sample -g. Moles of /a=H used Kffecti(e Molar Mass -gGmol.

A(erage J purity of aspirin -J. Holume of /a=H used -m$. Final %uret reading -m$. )nitial %uret reading -m$. Molarity of /a=H -molG$.& M /a=H solution.rial Aspirin 3ynthesis # . . MMMMMMMMMMMM 0ercent purity of aspirin -J. MMMMMMMMMMMM . -3how calculation %elow. -3how calculations %elow for &st run. Moles of /a=H used Kffecti(e Molar Mass -gGmol.Part IIb (!ab Synthesi"ed Aspirin) Calculate the mass of aspirin needed to reach the stoichiometric e*ui(alence point with ! m$ of a !.rial & Mass of aspirin sample -g.

0re>$a% +uestions &. diluted with water. How many moles of acetylsalicyclic acid are present in the sampleN %.#<B g sample of aspirin prepared in the la%oratory is dissol(ed in D#J ethanol.periment <.!! m$ of a !.&<# M /a=H a. A !. )n the e.cess amount of acetic anhydride.!! g of salicyclic acid reacts with an e. Calculate the theoretical yield of acetylsalicyclic acid for this synthesis . $ooking at the reaction used to prepare aspirin.# m$ of a !.&!! M /a=H solution d.& N Aspirin 3ynthesis B . Letermine the num%er of grams of acetylsalicyclic acid that will react with #. can you suggest a reason why it might %e possi%le to o%tain an KMM of less than &<E. Calculate the J purity of acetylsalicyclic acid in the aspirin sample c. and titrated to the phenolphthalein endpoint with &E.

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