Title: Synthesis, Recrystallization and Melting Point Determination of Aspirin

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.

Materials and Procedure

Materials and apparatus:
Ethanoic acid, salicylic acid, sulfuric acid, reflux condenser, heater, stirrer, round bottomed flask,
conical flask
Procedures
Synthesis of Aspirin
1. A 250 cm3 round bottom flask containing ethanoic acid (8.0g) and concentrated sulphuric
acid (3 drops) was collected.
2. 5 g of salicylic acid was collected.
3. The salicylic acid was added in small portions to the ethanoic acid/concentrated sulphuric
acid mixture
4. The flask was gently swirled after each addition of salicylic acid so that it is mixed with,
and dissolves in, the ethanoic acid.
5. When all the salicylic acid was added there were still some solid which did not dissolve.
6. A reflux condenser was connected to the round bottom flask and the reaction mixture was
heated under reflux in a water bath for about one and a half hour at 60C.
7. The reaction mixture was then left to cool.
8. The crude aspirin crystallized from solution at this stage.

Figure 1: Experimental Setup of Aspirin Synthesis

Recrystallization and Melting Point Determination

1. 20 cm3 of ethanol was added to the crystallized aspirin and was refluxed for about 20
minutes
2. Dissolved solution was the transferred to the beaker to be cooled.
3. Crystals were left to be formed.
4. Once crystals were formed, they were filtered using a filter paper and washed with cold
ethanol.
5. The filtered aspirin was then sent to the dryer to be dried for 15 minutes.
6. Once dried, samples were filtered again by being pressed in between filter papers to get a
dryer sample.
7. Once samples was completely dried, the weight of the aspirin was measured and
recorded.
8. Melting point of aspirin was determined by adding a sample of aspirin in a test tube and
placing the testing in an oil bath.
9. The oil bath was then heated until the aspirin starts to melt. Temperature of the melting
point was observed and recorded.

Figure 2: Filtration Process 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

Number of moles of ethanoic acid =

mCH 3 COOH
M CH 3 COOH

8g
60 g /mol

= 0.133 mol

Molecular formula of salicylic acid = C7H6O3

Molecular weight of salicylic acid = (12*7) + (1*6) + (16*3) = 138 g/mol

Number of moles of salicylic acid =

mC 7 H 6 O 3
M C 7 H6O3

5g
138 g/mol

= 0.036 mol

The limiting reagent = salicylic acid

Molecular formula of aspirin = C9H8O4
Molecular weight of aspirin = (12*9) + (1*8) + (16*4) = 180 g/mol
Theoretical yield = no. of moles of limiting reagent * Molecular weight of the product
= 0.036 mol * 180 g/mol
Theoretical yield = 6.48 g
Actual yield = 3.61 g
% yield = (actual yield/theory yield) x 100
% yield = (3.61/6.48)*100
% yield = 55.7%

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.

Figure 3: Weight of Final Product of Aspirin Collected

Conclusion and Recommendation

In this experiment, the reaction of salicylic acid with ethanoic acid produced acetylsalicylic acid
with a yield of 55.7% which was quite a low amount of yield. The product obtained had a
melting point of 137C. The theoretical melting point of 138C -140C, which showed a high
purity in the product obtained. More tests such as TLC to determine the purity of the aspirin
product should be carried out in order to obtain a purer final 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.