Title: Synthesis, Recrystallization and Melting Point Determination of Aspirin Aim
Title: Synthesis, Recrystallization and Melting Point Determination of Aspirin Aim
Title: Synthesis, Recrystallization and Melting Point Determination of Aspirin Aim
Aim
The aim of this experiment is to synthesize aspirin via reaction between salicylic acid and
ethanoic acid. It is carried out also to form aspirin at a high level of purity and yield.
Introduction
Acetylsalicylic acid (C9H8O4) or generally known as Aspirin, is one of the most famous medicine
used as it can cure many diseases. This includes its ability to be an antipyretic (reduces fever),
analgesic (reduces pain without producing anesthesia or loss of consciousness), antiinflammatory (relieve the pain and swelling with association to arthritis and rheumatism) and
many more. Aspirin was the first non-steroidal anti-inflammatory drug to be discovered and is a
derivative of salicylate, which can be found in plants such as willow trees and myrtle. The
synthesis of Aspirin is carried out to calculate for the percentage yield of aspirin.
Results
Weight of recrystallized product =3.61 g
Melting point range = 137 C
Literature m.p. = 138-140 C
% yield calculation
Molecular formula of ethanoic acid = CH3COOH
Molecular weight of ethanoic acid = 12 + (1*3) + 12 + 16 + 16 + 1 = 60 g/mol
mCH 3 COOH
M CH 3 COOH
8g
60 g /mol
= 0.133 mol
mC 7 H 6 O 3
M C 7 H6O3
5g
138 g/mol
= 0.036 mol
Discussion
In this reaction, ethanoic acid and salicylic acid is reacted under a temperature of 60C with the
help of a catalyst which was sulfuric acid. While the reaction continued, the color of the reaction
mixture changed from white to colorless. This was due to the increased heat, which increased
solubility and allowed the white salicylic acid crystals to dissolve, forming a colorless mixture.
However it about one and a half hour for the mixture to become a colorless solution.
After recrystallization, filtration and drying, our product yield was a mere 55.7%. The
yield was relatively low. This was because a lot of product was lost during filtration. A filter
paper was used to filter out the moisture from the final product. When the moisture was absorbed
by the filter paper, some aspirin was left behind on the filter paper. There were aspirin product
was also lost when transferring the wet product to the crucibles. This was done before sending
for drying. Yields of up to 90% will rarely, if ever, be reached.
The derived value of aspirins melting point was 137C. The theoretical value from
different literatures is in between the range of 138C to 140C. The experimental melting point
value is very close to the theoretical range, thus concludes that that part of the experiment was
achieved. The low yield and purity that we obtained in this experiment are not only due to the
experimental procedure and mechanism, but also to other experimental flaws. The low yields
could be due to several factors, such as disturbance during crystallization, incomplete reaction
and overheating. Also, with current experimental procedures it is difficult to determine whether
the reaction has reached full completion. A trace amount of salicylic acid and ethanoic acid might
still be present in the reaction mixture. Further tests for purification should be conducted to
analyze the overall purity of the aspirin product.
References
1. Synthesis of Aspirin. 2016. Synthesis of Aspirin. [ONLINE] Available at:
https://www.scribd.com/doc/50085284/Synthesis-of-Aspirin. [Accessed 18 March 2016].
2. Williamson, K. L. (2006). Synthesis of acetylsalicylic acid (aspirin). Macroscale and
Microscale OrganicExperiments, 2, 379.