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Synthesis of Aspirin (2EMT - Group 1, 2009)

Synthesis of Aspirin (2EMT - Group 1, 2009)

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Published by Mary Christelle
Group 1 Laboratory Report for Experiment 12
Synthesis of Aspirin

University of Sto. Tomas
Faculty of Pharmacy
Department of Medical Technology

Group 1 Laboratory Report for Experiment 12
Synthesis of Aspirin

University of Sto. Tomas
Faculty of Pharmacy
Department of Medical Technology


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Categories:Types, Research, Science
Published by: Mary Christelle on Oct 12, 2009
Copyright:Attribution Non-commercial


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Synthesis of Aspirin (Acetylsalicylic acid)Authors: ABESAMIS, M., ACOSTA, M., AGUSTIN, F.,
,BAGSICAN, M.AbstractAcetylsalicylic acid, known as Aspirin, is one of the popular andversatile medicines that cure diseases. It is considered a powerful drug forrelieving pain (analgesic), reducing fever (antipyretic), and reducing swelling(anti-inflammatory). The synthesis of acetylsalicylic acid is derived fromsalicylic acid which can be extracted in willow trees and allowing it to reactwith acetic anhydride and a catalyst through the principle of crystallization.I.IntroductionSalicylicacid isa fine whitecrystal andodorless. It isextracted inwillow andpoplar bark thathas been usedas an analgesicfor centuries.The boilingpoint osalicylic acid is 211°C and themelting point is 159°C. The densityof salicylic acid is 1.44 g/mol.Salicylic acid is very reactive inmoisture, light, heat, andincompatibilities such as iron salts,lead acetate, iodine and nitrousether. It is used in medicine suchas making aspirin andpharmaceutical applications,including methyl salicylate.Acetic anhydride isa colorless liquid with a pungentvinegar-like odor when it reactswith water to form acetic acid. Theboiling point of acetic anhydride is14C and the melting point is-73°C. It is soluble in ether,chloroform and benzene. It issoluble in water when aceticanhydride decomposes. Thedensity of acetic anhydride is 1.082g/ml in liquid state and itsmolecular weight is 102.09 g/mol.Acetic anhydride is most widelyused for the conversion of celluloseto cellulose acetate, which is acomponent of photographic filmand other coated materials. It isalso known as acetyl ether.Crystallization is one of themost used purifying methods inorganic experiments. It is aprocess of crystal formation in asolution. Organic compounds thatare solid in room temperature areusually purified by crystallization.The substance to be purified isdependent to its solubility inchange of temperature whether ina hot or cold solvent. It is the mainfactor that affects crystallization.The substance to be crystallizedshould show the ideal solubility
Figure 1 Structuralformula of SalicylicAcidFigure 2 Structural formula of Acetic anhydride
behavior in solvent. A substancecan be purified when both thedesired substance and the impurityhave similar solubility at its boilingpoint temperature, and when theimpurity represents only a smallfraction of total solid. The desiredsubstance will crystallize oncooling, but the impurities will not.The objectives obtained inthis experiment are the following:(1) to be able to explore thechemical process in the synthesisof aspirin; (2) and to calculate forthe percentage yield of thesynthesized aspirin.II.MethodologyTo synthesize aspirin, a 250-ml beaker filled with three-fourthsof tap water was subjected to boil.The beaker is supported by theiron ring and iron stand. A 250-mlplastic wash bottle filled withdistilled water was packed icewhich was placed in a largerbeaker. While boiling, exactly2.00 g salicylic acid was tared in awatch glass and it was transferredin a clean, dry 20-cm test tube.Exactly 5.00 ml acetic anhydridewas dispensed to the test tube and5 drops of concentrated sulfuricacid was added. Themixture is stirred using a stirringrod until the salicylic acid wasdissolved. The burner was turnedoff when the water in the beakerbegan to boil vigorously. The testtube was placed in a hot waterbath to allow the mixture the reactwithin a temperature range of 70°Cto 80°C in 20-30 minutes. Thecontent of the test tube was stirredwell in 1 minute. Then, the testtube was removed from the waterbath and its contents were pouredslowly and cautiously in 150-mlbeaker filled with 5 ml distilledwater. When the mixture subsided,the mixture was stirred in 1 minutewhile a drop of room temperaturewater was added at a time, until itreached a maximum of 40 drops orthe solution became cloudy. Whenthe solution became clear, a fewdrops of water were addeddropwise until crystals of aspirinreappeared. When there are nocrystals found, the inner walls of the beaker was scratched gentlyusing the stirring rod to inducecrystal formation. Once the crystalsof aspirin appeared, the test tubewas rinsed with a small volume of ice-cold water from the washbottle. A 20-ml of ice cold waterwas added into the 150-ml beakerthen the beaker was packed in icefor at least 10 minutes to allow theaspirin to be crystallized. Theaspirin crystals were filtered usinga pre-weighed filter paper and itwas dried overnight. Then, driedaspirin crystals were weighed.To test the purity of thesynthesized aspirin, it wassubjected to ferric chloride test forsalicylic acid. 1 ml water wasplaced in 6
test tubes. Asmall amount of each sample wasadded in every test tube using amicrospatula. Salicylic acid wasplaced in the first test tube,powdered commercial aspirin in thesecond test tube, synthesizedaspirin in the third test tube,benzoic acid in the fourth test tubeand 1 ml of benzoic acid in the fifthtest tube. The sixth test tube filledwith 1 ml water was the controlused. The sample used wasdissolved in 1 ml water then a dropof 2% aqueous solution of ferric
chloride was added using a Pasteurpipette. The observed colorproduced was noted.Another test of purity usedwas starch test. A 2 ml of waterwas placed in 3
test tube. Asmall amount of each sample wasadded in every test tube. Thepowdered commercial aspirin wasplaced in the first test tube andsalicylic acid in the second testtube. The third test tube with 2 mlwater was the control used. A dropof iodine solution was added ineach test tube. The observed colorproduced was noted.Methyl salicylate wasprepared in a similar manner asaspirin but at a lower temperature.Exactly 1.00 g of salicylic acid wasplaced in a 20-cm test tube. A 5 mlof methyl alcohol and 3 drops of concentrated sulfuric acidwas added to the test tube. Themixture is stirred until the salicylicacid is dissolved in alcohol. Then,the test tube was subjected in70°C water bath for 15 minutes.The mint aroma produced inferredthe presence of methyl salicylate.III.DiscussionThesynthesized acetylsalicylic acid isprepared by allowing salicylic acidto react in acetic anhydride with astrong acid as a catalyst such asconcentrated sulfuric acid andphosphoric acid. The principles incrystallization are applied to obtainthe desired product, aspirin. Thedifference in solubility of thesynthesized acetylsalicylic acid toits mother liquor at a lowertemperature will crystallize toobtain the desired substance. InTable 1, the used materials andsubstances are presented withtheir corresponding weight orvolume. The weight and volumewere accurately measured usingthe apparatus.
Figure 3 Structural formulaof Aspirin (Acetylsalicylicacid)

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