SYNTHESIS OF

ASPIRIN
GROUP 4 [2CHEA]

Cruz, Russel
De Juan, Abigail
Delos Santos, Kristian

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INTRODUCTION
- Background
- Concepts
- Objectives

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Background
● Acetylsalicylic acid, commonly known as aspirin, is an anti-inflammatory
pain reliever. It is an anti prostaglandin and a blood thinning agent.

● Discovered in the 18th century, when it was found that extract from barks of
willow trees was useful in reducing pain and fever.

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Concepts
● Aspirin can be produced by reacting salicylic acid in the presence of an acid
catalyst. [1]

● A substitution reaction in which the alcohol group (-OH group in salicylic

acid) reacts with acetic Anhydride to form an ester, aspirin. [1]

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Objectives
● to be able to successfully synthesize aspirin from salicylic acid

● to be able to purify aspirin via ethanol as recrystallization solvent

● to evaluate the purity of the synthesized aspirin through

ferric chloride test based from previous data from past experiments.

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METHODOLOGY
- Materials
- Process

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Materials
● Lab Instruments:
Erlenmeyer Flask, Beaker, Gauze, Tripod, Bunsen Burner, Iron
Stand, clamp, and filter paper.

● Chemicals used:
2.4 g salicylic acid, 6 ml acetic anhydride, & Concentrated H2SO4

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Process
A. Synthesis of Aspirin
1. Mix the salicylic acid (solid) & acetic anhydride (liquid) and 5 drops of
H2SO4
2. Heat the mixture at 80°C in 10 mins.
3. Cool down to room temp and add distilled water in it.
4. Put the flask in an ice bath for 10 minutes as soon crystals start to form. If
there is no crystal yet, try gently scratch the walls of flask by a glass
stirring rod
5. Filter the solution containing the crystals through a filter paper by using a
funnel and vacuum pump
6. Rinse the crystals with cold water and dry the crystals in air for a few
minutes.
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9
Process
B. Recrystallization of Aspirin
1. Dissolve the crude aspirin in 5 ml of ethanol in an
Erlenmeyer flask
2. Add 30 ml hot distilled water, then heat the solution until
it dissolves completely
3. Let the solution cool down to room temperature
4. Put the solution on an ice bath for 5 mins. Or until
crystallization is complete
5. Filter the solution with a filter paper, using a funnel and
vacuum pump.
6. Rinse the crystals with cold water, then dry it by air in
suction

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Process
C. Ferric Chloride Test
1. In each test tubes, put 1 ml of methanol in each in each
test tube
2. Add salicylic acid to test tube A, prepared aspirin to test
tube B and commercial aspirin at test tube C
3. Add FeCl3 to each test tube
4. Take note at the color changes in every test tube

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RESULTS AND DISCUSSION
- Computations
- Analysis

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Result and Discussion
Salicylic acid is suspended in excess of acetic
anhydride that serves as the reactant and
solvent [2]. Acetic anhydride is hydrolyzed
and splits in two where the first half forms the
aspirin, and the other forms the acetic acid.
The first half (COCH3) is exchanged to the
phenolic hydrogen in the salicylic acid to
form an ester.

Figure 2. Chemical Reaction of Aspirin Synthesis

Figure 3. Mechanism of Esterification
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 Result and Discussion
Table 1. Data from previous Experiment Table 2. Calculated Data from Previous Experiment

Salicylic Acid (kg) 2.4 g Limiting Reactant Salicylic Acid

Acetic Anhydride (mL) 6.0 mL Excess Reactant Acetic Anhydride

Acetic Anhydride (g/mL) 1.08 g/mL Theoretical Yield 3.132 g

Aspirin Produced (g) 2.92 g Percentage Yield 93.23%

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Result and Discussion

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Result and Discussion Figure 2. Iron(III)-Phenol Complexation
Table 3. Results from Ferric Chloride Test

Sample Color

Salicylic Acid Purple

Commercial Aspirin White

Prepared Aspirin White

Figure 3. Iron(III)-Phenol Complex

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 CONCLUSION AND
RECOMMENDATION

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Conclusion
1. The aspirin produced was pure.
2. The experiment process was efficient.
3. Alcohol-water solvent sufficiently recrystallized the aspirin.

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Recommendation
1. Recrystallized product needs to be better purified.
2. The experiment should be more closely and entirely conducted under the
fume hood to prevent and decrease exposure to atmospheric air.
3. A temperature controlled hot water bath could also be helpful in better
recrystallization, as well as more distilled water to aid in the dissolution of
acetic anhydride from the crystals.

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Thank You

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References:
[1] Experiment 8 - Synthesis of Aspirin [Pdf]. (n.d.). laney.edu/cheli-fossum/wp-content/uploads/sites/210/2012/01/8-
Synthesis-of-Aspirin.pdf

[2] Aspirin Synthesis and Analysis [Pdf]. (2014, December 13).

http://faculty.sites.uci.edu/chem1l/files/2014/12/D03MANAspirinSynAnalysis.pdf

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