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Abstract
Acetylsalicylic acid , known as Aspirin, is one of the popular and
versatile medicines that cure diseases. It is considered a powerful drug for
relieving pain (analgesic), reducing fever (antipyretic), and reducing swelling
(anti-inflammatory). The synthesis of acetylsalicylic acid is derived from
salicylic acid which can be extracted in willow trees and allowing it to react
with acetic anhydride and a catalyst through the principle of crystallization.
I. Introduction
Salicylic anhydride decomposes. The
acid is density of acetic anhydride is 1.082
a fine white g/ml in liquid state and its
crystal and molecular weight is 102.09 g/mol.
odorless. It is Acetic anhydride is most widely
extracted in used for the conversion of cellulose
willow and to cellulose acetate, which is a
poplar bark that component of photographic film
has been used and other coated materials. It is
as an analgesic Figure 1 Structural also known as acetyl ether.
for centuries. formula of Salicylic
The boiling Acid
point of
salicylic acid is 211°C and the
melting point is 159°C. The density
of salicylic acid is 1.44 g/mol.
Salicylic acid is very reactive in
moisture, light, heat, and
incompatibilities such as iron salts, Figure 2 Structural formula of
lead acetate, iodine and nitrous Acetic anhydride
ether. It is used in medicine such Crystallization is one of the
as making aspirin and most used purifying methods in
pharmaceutical applications, organic experiments. It is a
including methyl salicylate. process of crystal formation in a
solution. Organic compounds that
Acetic anhydride is are solid in room temperature are
a colorless liquid with a pungent usually purified by crystallization.
vinegar-like odor when it reacts The substance to be purified is
with water to form acetic acid. The dependent to its solubility in
boiling point of acetic anhydride is change of temperature whether in
140°C and the melting point is a hot or cold solvent. It is the main
-73°C. It is soluble in ether, factor that affects crystallization.
chloroform and benzene. It is The substance to be crystallized
soluble in water when acetic should show the ideal solubility
behavior in solvent. A substance slowly and cautiously in 150-ml
can be purified when both the beaker filled with 5 ml distilled
desired substance and the impurity water. When the mixture subsided,
have similar solubility at its boiling the mixture was stirred in 1 minute
point temperature, and when the while a drop of room temperature
impurity represents only a small water was added at a time, until it
fraction of total solid. The desired reached a maximum of 40 drops or
substance will crystallize on the solution became cloudy. When
cooling, but the impurities will not. the solution became clear, a few
drops of water were added
The objectives obtained in dropwise until crystals of aspirin
this experiment are the following: reappeared. When there are no
(1) to be able to explore the crystals found, the inner walls of
chemical process in the synthesis the beaker was scratched gently
of aspirin; (2) and to calculate for using the stirring rod to induce
the percentage yield of the crystal formation. Once the crystals
synthesized aspirin. of aspirin appeared, the test tube
was rinsed with a small volume of
II. Methodology ice-cold water from the wash
To synthesize aspirin, a 250- bottle. A 20-ml of ice cold water
ml beaker filled with three-fourths was added into the 150-ml beaker
of tap water was subjected to boil. then the beaker was packed in ice
The beaker is supported by the for at least 10 minutes to allow the
iron ring and iron stand. A 250-ml aspirin to be crystallized. The
plastic wash bottle filled with aspirin crystals were filtered using
distilled water was packed ice a pre-weighed filter paper and it
which was placed in a larger was dried overnight. Then, dried
beaker. While boiling, exactly aspirin crystals were weighed.
2.00 g salicylic acid was tared in a
watch glass and it was transferred To test the purity of the
in a clean, dry 20-cm test tube. synthesized aspirin, it was
Exactly 5.00 ml acetic anhydride subjected to ferric chloride test for
was dispensed to the test tube and salicylic acid. 1 ml water was
5 drops of concentrated sulfuric placed in 6 10-cm test tubes. A
acid was added. The small amount of each sample was
mixture is stirred using a stirring added in every test tube using a
rod until the salicylic acid was microspatula. Salicylic acid was
dissolved. The burner was turned placed in the first test tube,
off when the water in the beaker powdered commercial aspirin in the
began to boil vigorously. The test second test tube, synthesized
tube was placed in a hot water aspirin in the third test tube,
bath to allow the mixture the react benzoic acid in the fourth test tube
within a temperature range of 70°C and 1 ml of benzoic acid in the fifth
to 80°C in 20-30 minutes. The test tube. The sixth test tube filled
content of the test tube was stirred with 1 ml water was the control
well in 1 minute. Then, the test used. The sample used was
tube was removed from the water dissolved in 1 ml water then a drop
bath and its contents were poured of 2% aqueous solution of ferric
chloride was added using a Pasteur
pipette. The observed color
produced was noted.
III. Discussion
Table 1. Reaction of Acetic Anhydride and Salicylic Acid
Weight of watch glass + salicylic acid…….55.9455 g
Weight of empty watch glass………………....53.9374 g
Weight of salicylic acid…………...………….......2.0081 g
Volume of acetic anhydride……………………....….5.00 ml
Volume of concentrated sulfuric acid…...…….…....5 drops
Weight of filter paper + product ...…………..2.8310 g
Weight of dry filter paper....…………..…...……0.2000 g
Weight of product ...…………..…………………....2.6310 g
Limiting reagent:
Acetic anhydride:
Salicylic acid:
Theoretical yield:
Percentage yield: