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Aspirin

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SYNTHESIS OF ASPIRIN

LEGASPI Jhoe Cynder; LIWAG, James Timothy; MANGABAT, Allison Mae;


MARIANO, Jedidiah, MELAD, Mikee

UNIVERSITY OF SANTO TOMAS
FACULTY OF PHARMACY

Background of the study

Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever
reducer and as a pain killer

While Salicylic acid, whose name comes from Salix, the willow family of plants, was derived from willow
bark extracts. In folk medicine, willow bark teas were used as headache remedies and other tonics.
Nowadays, salicylic acid is administered in the form of aspirin which is less irritating to the stomach than
salicylic acid.

Materials:
Hard glass test tubes, 10-mL graduated cylinder, dropping pipette, beaker, thermometer,
stirring rod, filter paper, funnel

Methods
We weighed 2grams of salicylic acid and we transferred it to a hard glass test tube. Then we
added exactly 5mL of acetic anhydride. 5 drops of concentrated Sulphuric acid was added to the salicylic
acid and the mixture was stirred until it dissolved. The test tube containing the compound was placed in
a waterbath with a temperature of 70-80C for 20 to 30 minutes with occasional stirring. Room
temperature water was added until the mixture turned cloudy. When we removed the solution from the
water bath, we scratched the inner wall of the test tube and rinsed it with ice cold water. On a beaker,
we placed the rinsing and added 20mL of ice water to it and stirred. We allowed the aspirin to crystallize
by placing the beaker on an ice bath for 10 minutes. Then we filtered the solution in a pre-weighed filter
paper and allowed to dry. Afterward, the aspirin was weighed and placed in an amber bottle.

On the next part, we tried to determine the melting point of the synthesized aspirin. We placed
the aspirin inside capillary tubes then tied it to a thermometer and placed it in cooking oil. Then the
melting point range was measured. The 'melting point' is the range from the appearance of the first
liquid droplet until complete melting of the crystals. The expected melting point of aspirin is 138-140 C.

Purity of Aspirin was tested with 2 different tests; The Ferric Chloride Test for Salicylic acid and
the starch test. Wherein in the Ferric Chloride test for salicylic acid, each test tube contained Salicylic
acid, commercially available aspirin, prepared aspirin, Benzoic acid, Benzyl alcohol and Control which is
water, respectively then a drop of Ferric Chloride was added in each test tube and the color was noted.
While in the Starch test, each test tube contained prepared aspirin, commercially available aspirin and
the control which is water. A drop of iodine solution was added in each and the color was noted.





Conclusions

It can be concluded that Acetylsalicylic acid, commonly known as aspirin, could be synthesized using
salicylic acid, and acetic anhydride catalyzed with sulfuric acid. Aspirin can be made using the process of
esterification. It is when a carboxylic acid which is the salicylic acid and an alcohol, which is the acetic
anhydride that became an acetic acid, an alcohol, combine to form an ester, acetylsalicylic acid.
The aspirin is insoluble in cold water, so it can be isolated by filtering the chilled reaction solution.
Purification is necessary to remove any unreacted salicylic acid and acetic anhydride, as well as the
acetic acid product and phosphoric acid. Acetic anhydride is made to decompose by the addition of
water once the formation of aspirin is complete.
Also, the prepared Aspirin is very much similar to the commercially available aspirin except that when
starch test was made to both the prepared and commercially available aspirin, only the commercially
available aspirin showed a positive result which was light violet indicating the presence of starch in it.
Starch is widely used as a binder in medicines.

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