Basra University College of science and Technology

Pharmacy department

ORGANIC CHEMISTRY LABORATORY

Title of Report :-

Preparation of aspirin

Students Names :

‫علي مكي عبد الحسن‬

Supervised by:
Dr: Ahmed makki
THEORY:

Aspirin is a drug that is usually used to relieve minor aches and pain and other
medical uses such as anti-inflammatory medication. Aspirin is an ester that has
high molecular weight and it not soluble in water hence the solid can be separated
by crystallization process. Synthesis of Aspirin is known as esterification.
Acetic anhydride is uses as it is cheap and forms a by-product, acetic acid which is
not corrosive and can be recovered to make more acetic anhydride unlike other
acetylating agents that also can be used.
All addition of chemicals to aspirin is done in the fume hood. Fume hood is a local
ventilation device that is designed to limit exposure to hazardous or noxious fumes,
vapors and dust. A fume hood is a large piece of equipment five enclosed sides of a
work area, the bottom of which is most commonly located at a standing work
height.
The three main purpose of the fume hood are as follows:
1. Protect the user carrying out the experiment
2. Protect the product and experiment from undesired reactions.
3. Protect the environment from emission of harmful products.
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. The excess acetic acid
will be quenched with the addition of water. The aspirin product is not very soluble
in water so the aspirin product will precipitate when water is added. The synthesis
reaction of aspirin is shown below

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Aspirin still has its side effects. Note that the carboxylic acid functional group
remains intact. This may result in hemorrhaging of the stomach walls even with
normal dosages. The acidic irritation can be reduced through the use of buffering
agents, like antacids, in the form of magnesium hydroxide, magnesium carbonate,
and aluminum glycinate when mixed with aspirin (Buffering). While the ester can
be formed from acetic acid and salicylic acid, a better preparative method uses
acetic anhydrides in the reaction instead of acetic acid. An acid catalyst, like
sulfuric acid or phosphoric acid, is used to speed up the process.
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 C. 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.
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 product will be analyzed by three
different methods: melting point, titration, and spectroscopic assay.

Mechanism:

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Tools and Material:

1. Salicylic acid
2. Conical flask
3. Acetic acid anhydride
4. Filter paper
5. Water bath
6. Acid H2So4
7. distilled water
8. Conical flask 100ml

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procedure:

1. Place about 2 g of salicylic acid in the conical flask. In the fume hood, add
5.0 mL of acetic anhydride into the flask. Add 5 drops of conc. H2SO4
(catalyst) to the flask.
2. The mixture is heated in water bath for 10 to 15 minutes to (50-60) ℃ in
order to complete the reaction. Stir if needed to dissolve the salicylic acid.
Heat the water to boiling, and shut off the flame. Keep the flask in the hot
water bath for 15 minutes.
3. While the flask is still in the water bath, slowly add 2 mL of distilled water
to the flask to decompose any excess acetic anhydride.
4. Cool the mixture to room temperature or under the tap water.
5. Add (35 ml) of water with stirring.
6. Collect the product by filtration and wash it with cold water.
7. Transfer the filter paper and aspirin to a pre-weighed watch glass and allow
to dry in your

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Data:

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Discussion:
The purpose In this experiment is the synthesize of aspirin from acetic anhydride
and salicylic acid using sulfuric acid as a catalyst to speed up the reaction

According to my experiment and the results, I conclude that my end product is not
really pure. This can be seen from the calculation made based on my experiment
using this formula,

Percent yield is the amount of substance we have obtained in total in the

experiment. The experimental yield percentage is different from the theoretical
percentage is because there is loss of product often occurring during the isolation
and purification steps. The percent yield of the aspirin obtained from my
experiment is 38.5% yield.

The higher the yield percentage, the higher the purity of the aspirin will be.
Therefore, according to my results, the aspirin obtained is relatively impure.
However, the low percent yield can also mean that the reactant has not reacted
completely or the reaction is not complete.

However, there is also another possibility for the lower percent yield value. It is
the addition of water when carrying out suction filtration. As we have to wash
down the crystals before we carry out the suction filtration, some crystals might
have dissolved. Hence, the amount of water we use to wash down the crystals
during suction filtration might have affected the percent yield too.

 salicylic acid is administered in the form of aspirin so that it becomes less

irritating to the stomach than salicylic acid.

 Adding water to the reaction to reduce the excess of acetic anhydride.

 The aspirin will precipitate in water because it is not very soluble in water,
While acetic acid will easily separate from the aspirin product because acetic
acid is very soluble in water.

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 Adding water to the reaction to reduce the excess of acetic anhydride.

 Adding a small amount of a strong acid such as sulfuric acid used as a catalyst
to speeds up the reaction.

 The purpose of cooling is so that crystals of aspirin appear or can be shown.

 The mixture is heated in water bath for 10 to 15 minutes in order to complete

the reaction and to break the bond between carbon-oxygen and acetic
anhydride.

References:

 J. Olmsted III, Synthesis of Aspirin – A General Chemistry

Experiment, Journal of Chemical Education, 75 (1998), 1261.
 Royal Society of Chemistry. (2007). Aspirin- the wonder medicine.
 "Zorprin, Bayer Buffered Aspirin (aspirin) dosing, indications, interactions,
adverse effects, and more". Medscape Reference.
 Brayfield A, ed. (14 January 2014). "Aspirin". Martindale: The Complete
Drug Reference. Pharmaceutical Press.
 Algra AM, Rothwell PM (May 2012). "Effects of regular aspirin on long-
term cancer incidence and metastasis: a systematic comparison of evidence
from observational studies versus randomised trials"