Name: Dina L.

Lacson

Date of Experiment: August 16, 2016

Experiment # 1
SYNTHESIS OF ASPIRIN
I.

Discussion
Aspirin is the common name for the compound acetylsalicylic acid, widely used as an

antipyretic agent for reducing fever, as an analgesic agent which is to reduce pain and as an
anti-inflammatory. Nowadays, salicylic acid is administered in the form of aspirin which is
less irritating to the stomach than salicylic acid. It is an acetyl derivative of salicylic acid
which is a white, crystalline, weakly acidic substance with a melting point at 135C. In this
experiment, aspirin was synthesized through esterification reaction between Salicylic Acid
and Acetic Anhydride in the presence of concentrated sulfuric acid. Esters are the products of
the reaction of acids with alcohols, as shown as from the balance chemical equation below:

From the chemical equation the acetylsalicylic acid can be prepared by the reaction
between salicylic acid and acetic anhydride. A small amount of sulfuric acid (strong acid)
was used as a catalyst to hasten the reaction between the salicylic acid and acetic anhydride.
In this reaction, the hydroxyl group from benzene ring was reacted with acetic acid to form
ester functional group so this reaction is referred as esterification reaction. This shows that
the oxygen in salicylic acid attacks one of the carbons in acetic anhydride. Also, the
mechanism shows how acetic acid was separated from the acetylsalicylic acid. During the
reaction process, a molecule of water splits off and the remaining carboxylic acid and alcohol
fragments become attached producing an ester (alcohol + carboxylic acid). In this
experiment, the salicylic acid was the limiting reactant and the acetic anhydride was in

excess. According to Le Chateliers principle, the presence of excess acetic anhydride forces
equilibrium towards the desired product, which in this case is aspirin.
In the first part of the experiment, 2.1252 g of salicylic acid (C7H6O3) was prepared
and mixed with acetic anhydride. Acetic anhydride is very corrosive and has an extremely
disagreeable odor. With sulfuric acid acting as a catalyst, together, the mixture was hazardous
enough which was why this part was done in a fume hood. Heating of the mixture was done
and a clear yellow liquid was observed. Heating was employed so that salicylic acid would
melt and react with acetic anhydride and also to control the aspirin crystal formation and the
rate of reaction. However, the mixture should not be heated for a very long time for the
reason that it will just allow for the hydrolysis of the ester (acetic anhydride), which will just
yield back to salicylic acid. On the other hand, water was added after heating. This is to
prevent the reaction of acetic anhydride with water at the start of the experiment, if this had
happened, no aspirin could have formed. In this manner, acetic anhydride was decomposed
after the formation of aspirin. Each molecule of acetic anhydride forms two molecules of
acetic acid in its reaction with water. The acetic acid couples with the -OH group on the
salicylic acid molecule in a dehydration reaction to produce Aspirin and water. The water
produced reacts further with the acetic anhydride to perpetuate the reaction.
Purification is needed to eliminate any salicylic acid and acetic anhydride that did not
react, as well as the acetic acid product and sulfuric acid. The process is needed to make sure
that there is no impurities in the last product as much as possible. Thus the separation of
acetylsalicylic acid from other materials was accomplished and the product also washed with
distilled water after the crystal was formed because the water can decrease the solubility of
acetylsalicylic acid and dissolves the left impurities. Isolation was done through suction
filtration using Buchner funnel. The crude product was then weighed and it weighed 3.2990
g. This is quite far from the theoretical yield because it still contains impurities. This data
was then used to calculate the percent recovery of aspirin.
Recrystallization process was formed to more purify the product. Ethanol was used as
solvent in order to prevent the decomposition of salicylic acid because water can make
aspirin partially decompose while heating the solution. When the dissolution process is
endothermic, solubility increases with rising temperature. As the sample is allowed to cool
slowly to room temperature, the compound becomes less soluble and crystals come out of

solution. Any soluble impurities present in unsaturated amounts will remain in solution.
Thus, the impurities can now be separated from the compound by vacuum filtration.
Correct results for this experiment cannot be obtained if the aspirin decomposes. The
impurities in salicylic acid will decompose from incomplete reaction with acetic anhydrate so
after recrystallization, there is no impurities in the last product. This will cause the
precipitation of the acetylsalicylic acid (aspirin) and will react with any remaining acetic
anhydride. After which, ice cold distilled water was added. White, solid product (aspirin) was
beginning to be created at this point. The flask is then chilled in an ice-water bath for about 5
minutes until crystallization of the aspirin is complete. The aspirin crystals are collected on a
Buchner funnel and washed with additional ice cold distilled water, then the Acetic
anhydride decomposes to water soluble acetic acid. Aspirin has a low solubility in cold
water, so excess reactants could be washed away with cold water. Any other reaction
ingredients that were soluble passed through the filter paper which left the Aspirin free of any
excess acid. The product was a fine, solid, white powder. Compared to salicylic acid, the
crude product has finer particles.
The crude aspirin contains salicylic acid as its principal impurity, and
recrystallization gives us a convenient purification method. In this part, a small amount of
crude aspirin was separated for later comparison and a huge amount was placed in an
Erlenmeyer flask to be purified by recrystallization. In this purification method, the crude
aspirin was dissolved in a 6mL of ethanol and was heated in a hot water bath. Once the solid
was dissolved, 10mL distilled water was added and the solution was cooled slowly to room
temperature. The acetylsalicylic acid recrystallized, and the solid impurities remained
dissolved in the solution. The solid aspirin was again collected using vacuum filtration, then
a more pure aspirin product was supposed to be formed but due to some errors carried out
during the experiment such as heating and washing the sample, the obtained product did not
appear to be pure aspirin.
Based on the results of the calculation, the theoretical yield for this experiment is
2.772g while the actual yield is 2.169g. The percentage yield we obtained is 78.25%. The
percent yield is slightly near to 100 %. The computed % recovery of the recrystallized
aspirin weighing 1.491g is 68.76 %. These discrepancies on the data may be due to the
personal or systematic errors during the experiment. Lastly, melting point is a property

possessed by a certain compound. The melting point range of pure aspirin is 138-140 degree
Celsius and the melting point range of the salicylic acid starting material is 158-161 degree
Celsius. Impurities are present in the crude sample when the melting point range of the
resulting product is theoretically lower than the range of pure aspirin.
For the melting point data, the range of the crude sample was 127.5-129.2 C and the
range of the purified sample was 129.9-132.4 C. Comparing the results to the literature
value of 135C, both the purified and crude had a precise value but since the purified sample
has a narrower range, it is logically more comparable to the literature value. The melting
point of the crude and recrystallized aspirin was determined using a MP determination test.
Results showed that crude aspirin had a wider MP range compared to the recrystallized
aspirin. This means that there is still more impurities in the crude than in the recrystallized
aspirin.
Calculations
*Theoretical Yield

Mass of Aspirin=2.1252 g Salicyic Acid

1 mol Salicylic Acid

g
138.121
Salicylic Acid
mol

Aspirin
() 1 mol1 molSalicylic
Acid ) (

180.157 g
Aspir
mol
1 mol Aspirin

= 2.7720 g
*Percent Yield
% yield =

Actual yield
x 100
Theoretical yield

2.1691 g
= 2.7720 g x 100=78.25
II.

*Percent Recovery
Pure
% recovery= Impure x 100
1.4914 g
= 2.1691 g x 100=68.76 %

Conclusion
Aspirin was prepared from the reaction of salicylic acid and acetic anhydride.

Sulfuric acid was used as a catalyst. It was heated to have a higher rate of reaction. The
mixture was then cooled for the material to undergo crystallization. Upon addition of cold
water, acetic acid was formed and thus eliminated. The crystals were separated through
suction filtration. The other impurities, such as salicylic acid, from the preparation of aspirin

were removed in the process of recrystallization. Crystallization is a process wherein

molecules are arranged from a liquid state into a solid state. A method to check the purity of
the sample is to determine its melting point and compare the obtained value to the literature
melting point of the substance. A more pure substance has a narrow melting point range due
to less presence of impurities that may vary the melting point range. A less pure substance
has a wider range of melting point since it contains a larger presence of impurities that
widens the range. The melting point range of the purified and crude samples were compared
to the literature value and it showed that the purified sample is logically near to the
literature value because of its narrow range.
III.

References

McMurry, John. (2000). Organic Chemistry. 7th Edition USA.

Organic Chemistry II Laboratory Manual (2016): Department of Chemistry, College
of Arts and Sciences.

Aspirin(Acetylsalicylic

acid).

Retrieved

September

23,

2012

from

http://homepage/smc/edu/gallogly_ethan /files/Aspirin%20Synthesis.pdf

Brown, Lemay and Bursten. 2009. 11th Ed. Chemistry: The Central Science. Prentice
Hall, 534-537

Schmid, G. H. Organic Chemistry. (1991). St. Louis, Missouri: Mosby-Year Book,

Inc.