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[Chemical Engineering Laboratory 1

]

Preparation of Aspirin and Oil of
Wintergreen
Candidate’s Name

:

SAM KAR YEN

Student ID

:

SCM - 027837

Group Member’s Name

:
NG LIANG AIK
KOW JING YANG
FONG KAH WEI
TAN YEN BING
TAI SIM YEE
BRENDA CHOO MUN JENG
LIM SIN NIE
TAN WOAN GIUN
RONALD SELVAM
OLIVER PRASATH

Lecturer/ Supervisor

:

DR WONG VOON LOONG

Date of Submission

:

13th MARCH 2015

such as odour of strawberries and mint. To synthesis oil of wintergreen. To synthesis aspirin. Acetylsalicylic acid is commonly known as aspirin while methyl salicylate as oil of wintergreen. Esters basically have strong and pleasant scents. Suction filtration is performed to separate the residue. both the products collected were tested with 1% of iron (III) chloride. Three drops of concentrated sulphuric acid was added as a catalyst to speed up the reaction. all the changes were recorded. .1. In this way. many esters will be used as flavourings and perfume agents. as well as ointments for the relief of muscle pain. Formed aspirin is allowed to air dry. An ester compound can be formed by reaction of a carboxylic acid (compound containing –COOH group) and an alcohol (compound containing an –OH group). acetylsalicylic acid and methyl salicylate was synthesised. salicylic acid was mixed with methyl alcohol. Through this experiment. we can know that two different esters compound can be synthesised by the same chemical which is salicylic acid. ABSTRACT In this laboratory experiment. The reaction is termed as esterification. Sulphuric acid acts as a catalyst to increase the rate of reaction by lowering the activation energy. Finally. The odour released was noted before and after heating. 2. INTRODUCTION Organic compound synthesis and uses are very important section is this modern world. The residue was washed for several times as acetic anhydride is decomposed by the addition of water for the formation of aspirin. acetic anhydride and five drops of concentrated sulphuric acid was added to salicylic acid. Acetylsalicylic acid and methyl salicylate are both an ester.

as an anti-inflammatory medication to reduce redness and as an antipyretic to reduce fever.1 Acetylsalicylic acid Acetylsalicylic acid also known as aspirin. 1% FeCl3 solution is added to test for the presence of phenol.2 Methyl salicylate Methyl salicylate has a common name as oil of wintergreen. acetic anhydride was used instead of acetic acid in this experiment. . It is prepared by esterification of the carboxylic acid group (-COOH). Theoretically. has the potentiality as an analgesic to reduce minor pains. to accomplish the esterification more quickly. It is because acetic anhydride is more reactive. Thus. O OH OH + O H+ O O HO + O OH O O O Salicylic acid Acetic anhydride Acetylsalicylic acid acid Acetic acid 2. The colours range from green through blue and red through violet. Most of the phenols will form coloured complexes with iron (III) chloride. FeCl 3. However. of salicylic acid with methyl alcohol. OH OH + OH O Salicylic acid + H+ HO H2 O O O Methyl alcohol Methyl salicylate Phenol is a compound in which the hydroxyl group (-OH) attached to a phenyl ring (-C 6H5). Methyl salicylate is used as a flavouring agent and the in rubbing liniments that can relief the muscle cramping because it can penetrate through skin.2. Methyl salicylate will release a pleasant minty scents. This compound presents in both salicylic acid and methyl salicylate but not in acetylsalicylic acid. aspirin can be synthesised by heating salicylic acid and acetic acid for a certain period of time.

H2SO4 Distilled water 3. 3. 3.3 Chemical         Acetic anhydride 1% iron(III) chloride solution.2 Apparatus       125ml Erlenmeyer Flask 10ml graduated cylinder Filter paper 600ml beaker Large test tube Water bath 3.4 Cautions  If acetic anhydride and concentrated H2SO4 come in contact with skin. Experimental Method 3. Instead of disposing any chemicals down the sink.1 Objectives    To synthesis acetylsalicylic acid To synthesis methyl salicylate To review the phenol function group reacts with iron(III) chloride. Immediately wash the area with large amount of water if you get any of these  reagents on you.5 Procedure (i) Synthesis of Aspirin Add 3g of salicylic acid in a 125ml Erlenmeyer flask . can cause severe burns. use the waste containers provided. FeCl3 Salicylic acid Ice Absolute ethanol Methyl alcohol Concentrated sulphuric acid.3.

(ii) Synthesis of Oil of Wintergreen Place 1g of salicylic acid and 5ml of methyl alcohol in large test tube .Add 6ml of acetic anhydride and 5 drops of concentrated H2SO4 Mix the reagent by swirling the flask Place the flask in 80oC of water bath for 20 minutes Cool down to room temperature Add 40ml of distilled water to the mixture. Cool the mixture in ice bath Filter the crystals and wash with water Allow the crystal to air dry Obtain and record the mass of crystal.

Results and Analysis (i) Synthesis of Aspirin  Mass of salicylic acid = 3.00 g  Mass of crystallized aspirin .Add 3 drops of concentrated H2SO4 Place the test tube in 70oC of water bath for 15 minutes Note the odour Add a drop of 1% FeCl3 Note the colour changes 4.

02 mol  Theoretical grams of aspirin (mol wt of aspirin = 180 amu) 180 g × 0.36 g ×100 = 3. the aspirin was left for two days from the experiment day to air dry. Then it slightly changed to brownish colour after few seconds. The mass of dried aspirin weighed 3.56 % When FeCl3 was added to salicylic acid.11g and the mass of filter paper is 0.02 mol = 138 g g (1 amu = 1 ) mol  Theoretical number of moles of aspirin = Moles of salicylic acid used =0.02 mol = mol = 3.36 g The total mass of crystallized aspirin was weighed 12.mass of filter paper = 3.  Moles of salicylic acid used (mol wt of salicylic acid=138amu) 1mol × 2.= Total mass of crystallized aspirin .36 g=0. the colour changed from white to purple colour. .11g – 0.75g.75 g = 2.60 g  Percent yield grams aspirin obtained × 100 = theoretica l grams aspirin 2. but to get the mass of dry crystallized aspirin.135g.60 g = 65.

5. the colour changed from light pink to purple. (ii) Synthesis of Oil of Wintergreen Methyl salicylate releases a pleasant minty odour. To obtain the percentage yield. Then part of it changed to brownish colour after few seconds. divide mass of aspirin obtained with theoretical mass of aspirin. Theoretically. the colour changed from very light pink to purple colour. When FeCl3 was added to the product. When Fecl3 was added to recrystallized aspirin.When Fecl3 was added to aspirin. a change of colour is observed from colourless to purple colour.0 Discussion (i) Synthesis of acetylsalicylic acid O OH OH + O H+ O HO O O O + OH O O Salicylic acid Acetic anhydride Acetylsalicylic acid acid Acetic acid Acetylsalicylic acid is also well known as aspirin. number of moles .

of aspirin is equal to number of moles of salicylic acid used. acetic anhydride was used instead of acetic acid in this experiment. ratio of salicylic acid used and aspirin formed is 1:1mol in the process of esterification. Cold as opposed to warm water was used to wash the aspirin that prepared because aspirin is more soluble in warm water. However. more precipitates is gained. Cold water would not dissolve as much as warm water do. It is because acetic anhydride is more reactive. The suction filtration process in this experiment is to separate the residue which is unreacted salicylic acid and acetic anhydride. if the aspirin dissolves in warm water. . Thus. When 1% of FeCl3 is added to the aspirin obtained. a bad yield will be gained. there is still water content in the aspirin. the colour changed from light pink to purple because it was impure. As the temperature lowers. It is because according to the equation above. H2SO4 acts as a catalyst in this experiment. to accomplish the esterification more quickly. There is a colour change from white to purple colour when 1% of FeCl3 is added to the salicylic acid because of the presence of phenol ring in it. The residue was washed for several times as acetic anhydride is decomposed by the addition of water for the formation of aspirin. no changes of colour will occur when FeCl3 were added to pure aspirin because the phenolic (-OH) of salicylic acid is protected by the acetate group (-OOCCH3). To obtain the mass of aspirin without the water content. However. H2SO4 will not increase the aspirin obtained but will lower the activation energy to formed a product. this minimizes the product loss. so that the rate of reaction is faster. If the experimental yield of aspirin obtained is greater than 100%. the product formed is allowed to air dry. means the aspirin is not completely dry. the mass of aspirin recorded is higher than the mass of the theoretically aspirin. The crystal can only be caught by the filter paper.

When FeCl3 is added to oil of wintergreen. online. 6. It is because the phenol group in it. Both products are an ester. online.0 Conclusion In this experiment.edu/sites/apsu. from  http://www. can know that methyl salicylate will release a pleasant minty odour. Methyl salicylate has a common name which is Oil of Wintergreen. However.edu/files/chemistry/SP11_1021_Synthesis_of_Aspirin_a  nd_Oil_of_Wintergreen. retrieved on 9th March 2015. the aspirin obtained was impure.academia.0 References  Acetylsalicylic Acid (Aspirin) Synthesis.(ii) Synthesis of Methyl salicylate The reaction occurred between salicylic acid and methyl alcohol is also known as esterification. The minty odour released is because esters basically will release strong and pleasant odour. Colour changes are observed when 1% of FeCl3 is added to both products to test the presence of phenol group.apsu.edu/4728996/Acetylsalicylic_Acid_Aspirin_Synthesis Synthesis of Aspirin and Oil of Wintergreen. The concentrated H2SO4 added in the reaction acts as a catalyst to overcome the activation energy to form methyl salicylate. from https://www. the colour changed from colourless to purple colour. so there was a colour changes. pure aspirin would not have any colour changes when tested with FeCl3. retrieved on 9th March 2015. From the common name. 7. Theoretically.pdf Experiment 1: Preparation of aspirin and Oil of Wintergreen from Laboratory Handbook . both the synthesised product is formed by the common chemical which is salicylic acid undergoes the process of esterification.