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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
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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

&

salicylic acid has a higher melting point than aspirin, if the aspirin has a trace amount of salicylic acid the melting point of the mi;ture will %e lower than pure aspirin. +ualitati(ely, it is also possi%le to detect the presence of salicylic acid using ferric chloride. 3alicylic acid forms a colored comple; with acidified iron -))). ion which is readily (isi%le at low concentrations. Figure <.

Figure <'
,he addition of acidified iron -))). ion produces the (iolet tetraa*uosalicylatroiron -))). comple;.
?

=> > ? @Fe-H =.B A C = =


?<

= C =

Fe-H =." =

? H = ? H <=

Aspirin does not form this comple;. ,his forms the %asis for a simple *ualitati(e test for the presence of unreacted salicylic acid in your aspirin. +uantitati(ely, the purity of an aspirin sample can %e determined %y a simple acid>%ase titration. 6oth aspirin and salicylic acid are weak organic acids %ut with different properties, ,a%le &. ,a%le & Compound' Formula' Molar Mass' Melting point' 1a p1a 3olu%ility -gG&!!m$. where -&. Holume /a=H, $ ; Molarity of /a=H, molG$ I mol /a=H I moles acid /ote that salicylic acid has a lower molar mass. ,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. ,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. )n fact, %y titrating a known weight of our sample with a standard /a=H solution we can determine the 7effecti(e molar mass9 -KMM.. KMM I grams of sampleGmoles acid from titration 3alicylic Acid CCHB=< &<E.& &#E>&B!FC &.!E ; &!>< .DD !.&E Aspirin CDHE=" &E!.&# &"!>&" FC .C ; &!># ".#C !. #

A standardized /a=H solution titrates the acid to the phenolphthalein endpoint,

Aspirin 3ynthesis

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

&. Repeat the procedure a%o(e using the aspirin synthesized in CHM !"#$.

Aspirin 3ynthesis

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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 !.& M /a=H solution. -3how calculation %elow. . ,rial & Mass of aspirin sample -g. Molarity of /a=H -molG$. )nitial %uret reading -m$. Final %uret reading -m$. Holume of /a=H used -m$. Moles of /a=H used Kffecti(e Molar Mass -gGmol. MMMMMMMMMMMM 0ercent purity of aspirin -J. -3how calculations %elow for &st run. A(erage J purity of aspirin -J. MMMMMMMMMMMM ,rial

Aspirin 3ynthesis

"

Part IIb (!ab Synthesi"ed Aspirin) Calculate the mass of aspirin needed to reach the stoichiometric e*ui(alence point with ! m$ of a !.& M /a=H solution. -3how calculation %elow.

,rial & Mass of aspirin sample -g. Molarity of /a=H -molG$. )nitial %uret reading -m$. Final %uret reading -m$. Holume of /a=H used -m$. Moles of /a=H used Kffecti(e Molar Mass -gGmol. MMMMMMMMMMMM 0ercent purity of aspirin -J. -3how calculations %elow for &st run. A(erage J purity of aspirin -J. MMMMMMMMMMMM

,rial

Aspirin 3ynthesis

0re>$a% +uestions &. A !.#<B g sample of aspirin prepared in the la%oratory is dissol(ed in D#J ethanol, diluted with water, and titrated to the phenolphthalein endpoint with &E.# m$ of a !.&<# M /a=H a. How many moles of acetylsalicyclic acid are present in the sampleN

%. Calculate the J purity of acetylsalicyclic acid in the aspirin sample

c. Letermine the num%er of grams of acetylsalicyclic acid that will react with #.!! m$ of a !.&!! M /a=H solution

d. )n the e;periment <.!! g of salicyclic acid reacts with an e;cess amount of acetic anhydride. Calculate the theoretical yield of acetylsalicyclic acid for this synthesis

. $ooking at the reaction used to prepare aspirin, can you suggest a reason why it might %e possi%le to o%tain an KMM of less than &<E.& N

Aspirin 3ynthesis

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