chm457 4

Title
Preparation of Acetylsalicylic Acid (Aspirin)
Objectives
To learn how to prepare Acetylsalicylic Acid (Aspirin)
Introduction
Aspirin is the common name for the compound acetylsalicylic acid, widely
used as a fever reducer and as a pain killer. 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. To prepare aspirin, salicylic acid is reacted with an
excess of acetic anhydride. A small amount of a strong acid is used as a catalyst
which speeds up the reaction. In this experiment, phosphoric acid will be used as the
catalyst.
Since acetic acid is very soluble in water, it is easily separated from the aspirin
product. The aspirin isolated in this step is the “crude product”. A “purified product”
can be obtained through recrystallization of the crude product in hot ethanol. In this
experiment, the crude product will be the desired product. The percent yield of the
crude product will be determined for this reaction. The purity of the product will also
be analyzed.
The melting point range of pure aspirin is 138-140 C and the melting point range of
the salicylic acid starting material is 158-161 oC. If impurities are present in your
crude sample, the melting point range for your product will be lower than the range of
pure aspirin. Also, your melting point range may be greater than 2 degrees.
Procedures
Preparation of Acetylsalicylic Acid (Aspirin)
2.0 g of salicylic acid was placed in a 125 ml Erlenmeyer flask. 5.0 ml of acetic
anhydride and followed by 5 drops of concentrated sulfuric acid were added to the
same flask. The flask was swirled gently until salicylic acid dissolved. The flask was
then heated on hot water bath at 50oC for 10 minutes. The flask was cooled at romm
temperature which the acetylsalicylic acid began to crystallize. The walls of flask was
scratched with a glass rod and cooled down slightly in an ice bath if the crystallization
does not occur. After crystal formation was completed, 50 ml of water was added and
the mixture was cooled in an ice bath.
Vacuum filtration
The product was collected by vacuum filtration using Buchner funnel. Small amount
of cold water was used to aid the transfer of crystal to the funnel. The cold water was
also used to rinse the crystals for several times. The air through the crystals was
drawed on the Buchner funnel by suction process until the crystals were free of
solvent for 10 minutes. The crystals was removed for air drying. The crude product
was weighed and it may contain some unreacted salicylic acid. The percentage yield
of crude acteylsalicylic acid was calculated.
Ferric Chloride Test for Purity

The test was conducted when the sample of crude acetylsalicylic acid was not
completely dried. Three test tubes was obtained and 0.5 ml water was put into each
test tube. A small amount of salicylic acid was dissolved in the first test tube. A
similar amount of product was added into the second test tube. The third test tube was
only contains water which is solvent that will serve as the control.
One drop of 1% ferric chloride solution was added to each test tube and the colour
canges was recorded. Formation of an iron-ohenol complex with Fe(III) gave a
definite colour ranging from red to violet.
Recrystallization
If the product contains unreacted salicylic acid, the product was the dissolved in a 2-3
ml minimum hot ethyl acetate in a 25 ml Erlenmeyer flask. The flask was gently and
continuously heated in a hot water bath. The mixture was cooled at room temperature
while the aspirin crystallized. The acetyl acetate was evaporated and the solution was
cooled in ice bath. Next, the product was collected by vacuum filtration using
Buchner funnel. The remaining material was rinsed out of the flask with a few ml of
cold petroleum ether. The residual solvents was disposed in the waste container for
nn-halogenated organic waste. The purity of aspirin was tested again using ferric
chloride test. The melting point of the aspirin was obtained with a completely dried
sample.

chm457 4

Uploaded by

Copyright:

Available Formats

chm457 4

Uploaded by

Document Information

Original Description:

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

chm457 4

Uploaded by

Copyright:

Available Formats

Title

Preparation of Acetylsalicylic Acid (Aspirin)

To learn how to prepare Acetylsalicylic Acid (Aspirin)

Preparation of Acetylsalicylic Acid (Aspirin)

Ferric Chloride Test for Purity

You might also like