aspirin (asa) orgo 232 betty weiss

8/17/2019 Aspirin (Asa) Orgo 232 Betty Weiss

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PREPARATION OF ASPIRIN BY

SYNTHESIS AND CRYSTALLIZATION

Instructor : Dilusha Harischandra PhD

Student: Betty Weiss


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PREPARATION OF ASPIRIN BY SYNTHESIS AND CRYSTALIZATION

By: B!tt" #!iss

Date of experiment:

A$ril %&'()

INTROD*CTION

Aspirin belongs to a group of organic compounds known as esters. Aspirin is an analgesic ,an

antipyretic and anti-inflammatory agent. Bayer coined the name “A!"#"$% for their new product to

reflect its acetyl nature and its natural occurrence in the piraea plant. Aspirin alters the oxygenase

acti&ity of prostaglandin synthetase by mo&ing the acetyl group to a terminal amine group of the

en'yme. "t interferes with the cyclooxygenase-( and cyclooxygenase-) en'ymes.

"n the *th century B.+. the reek physician ippocrates describes an extract of willow tree bark, a

bitter powder that could be used to reduce fe&ers.

"n (/0 1dward tone 2a clergyman3 had collected obser&ations from around the country on the effect

of willow bark on the relief of fe&er due to malaria.

"n (4056s a cottish physician found that extract of willow bark relie&ed symptoms of acute

rheumatism.

"n (456s !rofessor &on $encki of Basle demonstrated that salicin, the pharmacological ancestor of

salicylates was con&erted into salicylic acid in the body after it is eaten with another chemical.

alicylic acid can cause irritation to the mucous membranes of the mouth and esophagus and se&erely

upset stomach. 7arge doses up to 4 grams of sodium salicylates were used to treat arthritis, which was

not tolerated by many patients without causing se&ere stomach irritation.


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Fi+ur! ( : alicin is an alcoholic 8- glucoside. Fi+ur! & : alicylic acid 2)-ydroxyben'oic acid3

"n (490 a erman chemist elix offman was working for the Bayer pharmaceutical company under

Arthur 1ichengrun and his research led to the synthesis of AA acetylsalicylic acid.

Bayer named the drug “Aspirin%, the drug was so popular that the name “aspirin% became a generic

name and Bayer6s rights to the trademark were lost or sold in many countries. Aspirin6s profitability

led to fierce competition and the proliferation of aspirin brands and products. Aspirin6s popularity

declined only after the de&elopment of paracetamol 2acetaminophen3 in (9*/ and ibuprofen in (9/).

SYNTHESIS OF ASPIRIN ,ASA-

Aspirin can be produced in one step chemical process by reacting salicylic acid with acetyl anhydride.

;he synthesis of aspirin is classified as an esterification,it6s a reaction between a carboxylic acid and


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an alcohol which is cataly'ed by mineral acid.Aspirin is both an organic esther and an organic acid .

Salic"lic acid Ac!tic anh"drid! Ac!t"lsalic"lic acid Ac!tic acid

C.H)O/ C%H)O/ C0H1O% C&H%O&

2ATERIALS


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REA3ENTS AND PROPERTIES

(4

Salic"lic acid

C.H)O/

>>: (04.() g?mol

>!: (*9 @ +

B!: )55-)(( @ +

a'ard: alicylic acid is capable of penetrating and breaking down fats and lipids, causing moderate

chemical burns of the skin at &ery high concentrations. hen ingested, salicylic acid may ha&e

possible ototoxic effect it can induce hearing loss in 'inc-deficient indi&iduals. "n late pregnancy has

been associated with bleeding, especially intracranial bleeding. alicylic acid o&erdose can lead

to salicylate intoxication, which often presents clinically in a state of metabolic acidosis. e&eral

studies also support an association between exposure to salicylic acid and #eyeCs syndrome.


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&4

Ac!tic anh"drid!

C%H)O/

>>: (5).59 g?mol

>!: -0.( @+

B!: (09.4@+

a'ard: Acetic anhydride is an irritant and combustible liuid. ;he &apor of acetic anhydride is

harmful, when mixed with hydrogen peroxide an excess of acetic anhydride can form an explosi&e.

/4

Sul5uric acid conc!ntrat!d


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H&SO%

>>: 94.59 g?mol

>!: (5 @+

B!: 00 @+

a'ard: igh concentration of sulfuric acid causes &ery se&ere burns, if ingested it damages internal

organs irre&ersibly and may e&en be fatal. "t6s also highly corrosi&e.

%4

Ethanol

C&H)O

>>: !: -((< @+

B!: 4.0@+

a'ard: 1thanol is a &olatile, flammable colorless liuid with a slight chemical odor. Death from

ethanol consumption is possible when blood alcohol le&els reach


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• eight (.5 g of salicylic acid and place into*.5 ml 1rlenmeyer flask.

• Add ).* ml of acetic anhydride to the flask and swirl.

• +arefully add 0 drops of concentrated sulfuric acid catalyst to the reaction mixture and swirl.

• eat the flask in the hot water bath for (5 minutes, stirring with a glass-stirring rod until the

salicylic acid dissol&es completely.

• Add *.5 ml of deioni'ed ice water to decompose any excess of acetic anhydride.

• !repare an ice water bath in a aintain the &acuum until the crystals are relati&ely dry.

RECRYSTALLIZATION OF THE ASPIRIN

;ransfer the aspirin crystals into *5 ml beaker.

Add < ml of ethanol and () ml of distillated water.

arm the mixture in a /5 @+ water bath until the crystals dissol&e completely.

• +o&er the beaker with watch glass, set aside to cool to room temperature.

• !lace the beaker in the ice water bath to complete recrystalli'ation.

• Determine the mass of the aspirin crystals.

• Determine the melting point of the aspirin sample and run an "#.


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Fi+ur! %: Displaying crude and recrystalli'ed aspirin.

Fi+ur! 6: Displaying beautiful needle-like crystals of

acetylsalicylic acid.

RES*LTS AND CONCL*SIONS

>ass of salicylic acid: (.5(*4g

>ass of crude aspirin: (./)/*g 2(.*)4g = 5.()/0g mass of filter paper3

>ass of purified aspirin: 5.))95 g 25.0


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;heoretical yield of aspirin: 5.550 mol + x (45.) +?(mol + E (.0)g

P!rc!nt "i!ld o5 as$irin: (.4/6 7

5.))95g?(.0)gx(55E (.0*F

2!ltin+ $oint o5 as$irin: (/%41 8C

tarting melting point: (0).0 @+

inal end melting point: (0


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Fi+ur! ): Displaying "# of the product 2aspirin3

Based on "#, melting point and comparing the literature " came to the conclusion that my product is a

purified aspirin.

Fi+ur! .: Displaying literature "# of aspirin


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Mass Spectrum

acetoxybenzoic acid C9H8O4 (Mass of molecular ion: 180)

Source Temperature: 250 °C

Sample Temperature: 25 °C

Direct, 70 eV

Peak Data:

15.0 1.3 38.0 1.6 39.0 4.4 42.0 1.2

43.0 30.3 50.0 1.1 53.0 1.5 62.0 1.3

63.0 4.8 64.0 5.0 65.0 4.7 81.0 1.8

92.0 24.7 93.0 3.4 120.0 100.0 121.0 14.7

122.0 1.2 138.0 65.2 139.0 5.1 180.0 1.6

Fi+ur! 1: Displaying literature > of aspirin


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1H NMR 399.65 MHz

C9 H8 O4 0.039 g: 0.5 ml CDCl3

o-acetoxybenzoic acid


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Fi+ur! 0: Displaying literature ( $># of aspirin

13C NMR 50.18 MHz

C9 H8 O4 0.039 g: 0.5 ml CDCl3

o-acetoxybenzoic acid


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Fi+ur! (': Displaying literature (0 + $># of aspirin

inal taught take an aspirin 45 mg a day, please see below:


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Fi+ur! ((: Aspirin bottle from (490

Fi+ur! (&: Aspirin packaging from Bayer pharmaceutical 2)5(*3


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REFERENCES

Glmsted, H. A. ynthesis of Aspirin: A eneral +hemistry 1xperiment. Journal of Chemical

Education (994 , 75.

aspirin (asa) orgo 232 betty weiss

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