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Experiment 1

SYNTHESIS OF ASPIRIN
I.

Discussion
The experiment was divided into three parts: (1) synthesis of aspirin, (2) purifying the
aspirin by recrystallization, (3) melting point determination. It lasted three meetings due to the
lengthy time required to dry the product.
The main objective of the experiment is to synthesize acetylsalicylic acid (C 9H8O4) or
aspirin from salicylic acid (C7H6O3) via esterification reaction and to test the purity of the
product.
In the first part of the experiment, 3 ml of acetic anhydride is added to 2.1084 grams of
salicylic acid, a crystalline white powder placed in a dry Erlenmeyer flask. Subsequently, the
mixed solution was heated via hot water bath in the presence of an acid catalyst, sulfuric acid
(H2SO4) to make the reaction rate faster. The heating was done to increase the solubility rate and
to favor the formation of products since it is an exothermic reaction. As the reaction continues
the salicylic acid decomposes and the acetylsalicylic acid remains dissolved in the hot solution.
When the entire solid has dissolved, the excess acetic anhydride was hydrolyzed to acetic acid by
adding distilled water. The distilled water was added drop-wise since acetic anhydride is very
reactive toward water. Also the water was added after heating and not at the start of the
experiment to prevent the reaction of acetic anhydride with water at the beginning of the
experiment, otherwise no aspirin product will be obtain from the reaction. The two reactions
involve are shown below.

Synthesis of aspirin

Hydrolysis of acetic anhydride

To lower the solubility as well as to precipitate the aspirin product, 10 grams of crushed
ice was added into the flask and allowed to cool in an ice bath with occasional stirring.
Subsequently, the solution appeared cloudy-white.
The white aspirin crystals were collected via filtration using Buchner funnel. Since
aspirin is insoluble in cold water, cold distilled water was used to wash the remaining crystals in
the flask.

In this manner, aspirin products remain undissolved. Cold water acts as a purifying

agent since it eliminates impurities such as acetic acid and sulfuric acid which are soluble in
water at any temperature. However, there may be any remaining unreacted salicylic acid since it
is only slightly soluble in water thus cannot be removed completely in washing.
The aspirin crystals collected was considered as crude product. The crude aspirin
weighed 8.7876 grams, an experimental value far from the theoretical yield calculated as:
mass of aspirin=2.1084 g salicylic acid x
2.7503 g aspirin

1 mol salicylic acid


1 mol aspirin
180.17 g of aspirin
x
x
138.12 g salicylic acid 1 mol salicylic acid
1 mol aspirin

The percent yield was calculated as:


experimental yield
theoretical yield

Percentage yield =

8.7876 g
2.7503 g

x 100

x 100

320
An enormous error was obtained. When the sample is weighed, it was not completely
dried. It was due to personal errors of the group who performed the experiment. They were
thinking that if they leave the product uncovered inside the locker, dust particles coming from
the walls of the locker may fall on it and will contribute to impurities of the product. Therefore,
they placed the product on an evaporating dish then covered it with a watch glass.

The second part of the experiment was purification of aspirin by recrystallization. The
crude aspirin was placed in an Erlenmeyer flask then 6 ml of ethanol was added. Ethanol is used
to dissolve aspirin along with the impurities such as salicylic acid. The flask was then subjected
to heat via a hot water bath to further dissolve the remaining solid. Afterwards, 10 ml of distilled
water was added to the flask and slowly cooled at room temperature before cooling it in an ice
bath for another five minutes with occasional stirring. All the remaining impurities were
eliminated by washing with cold water then filtered via suction filtration. The product collected
was considered as the purified aspirin and was allowed to dry inside the locker.
The weight of the recovered sample was 1.5055 grams. The percentage yield of purified
aspirin was calculated as:
Percentage yield =

experimental yield
theoretical yield

x 100

1.5055 g
2.7503 g

x 100

55
The factor that contributes to the low percentage yield of purified aspirin was the weight
of the product recovered. It did not dry completely by the time it was weighed.
In the third part of the experiment, the melting point of the crude and purified aspirin was
determined using electrothermal apparatus. The lower the melting point means more impurities
are present in the sample. The samples were placed into the capillary tubes having two trials for
each sample. The resulting melting point range of the crude sample for the trials one and two
were 127.8 C - 128.4 C and 127.8 C - 128.8 C, respectively. Purified or recrystallized aspirin
resulted to melting point range of 130.3C - 132.2C and 130.3C - 132.7C for trials one and
two, respectively. Comparing the results to the actual melting point of the aspirin 138 C - 140
C, it can be seen that the recrystallized product is near to the literature value, hence it is nearly
pure.
The possible factors that affect the resulting purity of the product were the temperature
and the amount of the water used in the washing of the crude product resulting to failure in
eliminating impurities.

II.

Conclusion
Aspirin was synthesized from salicylic acid via the process of esterification reaction. The
addition of catalyst and heating was done to speed up the reaction. The impurities in product
collected were eliminated by washing the product with cold water and recrystallization.
The melting point range of the purified sample is closer to the actual or theoretical
melting point value of aspirin than that of the crude samples melting point range.

The chain of errors were the (1) uncompleted filtration that affects the time of drying, (2)
the time of drying that affects the weight of the sample, (3) the weight of the samples that
contributes to the erroneous percentage yield.

III. References
[1] Full report: Synthesis of
aspirin.http://theuplbcollegestudent.blogspot.com/2011/05/full-report-synthesis-ofaspirin.html (accessed Aug 23, 2016)
[2] Synthesis of Aspirin results and Discussion. http://docslide.us/documents/synthesisof-aspirin-results-and-discussion.html (accessed Aug 23, 2016)
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[3] Aspirin Synthesis. http://www.lahc.edu/classes/chemistry/arias/Exp%205%20%20AspirinF11.pdf (accessed Aug 23, 2016)


[4] Experiment 8 Synthesis of Aspirin. http://www.laney.edu/wp/chelifossum/files/2012/01/8-Synthesis-of-Aspirin.pdf (accessed Aug 23, 2016)

[5] Experiment 6 Synthesis of Aspirin (Acetylsalicylic Acid). .


http://mason.gmu.edu/~jschorni/chem211lab/Chem%20211-212%20Aspirin.pdf
(accessed Aug 23, 2016)