Student number:21828003

Initials:S.P
Surname:Ntshingila
Course:Beng Tech Chemical engineering
Experiment 3
Preparation of Aspirin from salicylic acid and acetic
anhydride

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 Table of content
aim 3

introduction 3

reaction scheme 4

table of chemicals 4

procedure 6

mechanism 7

results 8

discussion 9

conclusion 10

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Aspirin from salicylic acid and acetic anhydride

Aim
This aim of this experiment focuses on the synthesis of aspirin from acetic anhydride and salicylic acid
while using concentrated sulfuric acid as a catalyst for the experiment

Introduction

Aspirin, also known as acetylsalicylic acid, is a medication used to reduce pain, fever, or inflammation.
Specific inflammatory conditions which aspirin is used to treat include Kawasaki disease, pericarditis,
and rheumatic fever. The use of aspirin had its origin in the 18th century, when it was found that an
extract from the bark of willow trees was useful in reducing pain and fever. The active ingredient in
willow bark was later found to be salicylic acid. Nowadays, salicylic acid is administered in the form of
aspirin which is less irritating to the stomach than salicylic acid. To prepare aspirin, salicylic acid is
reacted with an excess of acetic anhydride with concentrated sulphuric acid acting as a catalyst

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Reaction scheme

C7H6O3 + C4H6O3 → C9H8O4 + CH3COOH

Salic acid + Acetic anhydride → aspirin + acetic acid

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Table of chemicals

table of chemicals/ reagents

No. of
name quantity melting points boiling points hazards
moles

Acetic Anhydride is a
HIGHLY CORROSIVE
CHEMICAL and
contact can severely
irritate and burn the
skin and eyes with
possible eye damage.
* Breathing Acetic
acetic anhydride 4.32g 0.042 -73.1 139.8
Anhydride can
irritate the nose,
throat and mouth.
High concentrations
can cause severe
lung damage with
coughing and/or
shortness of breath

Combustible. Finely
dispersed particles
salicylic acid 2.0g 0.014 158.6 211
form explosive
mixtures in air.
May be harmful if
inhaled. Causes
aspirin 2.5g 0.019 135 140
respiratory tract
irritation

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Procedure
1. Use a centigram balance to weigh 2 g of salicylic acid into a clean dry 125 cm 3 conical flask,
2. Add 4.0 cm3 of acetic acid in to the flask with precaution
3. Add 5 drops of concentrated sulphuric acid with will serve as a catalyst
4. Gently swirl the mixture and cover it with aluminum foil to prevent water from entering the
flask
5. Heat the mixture in the flask in a boiling water bath for 30 minutes
6. Remove the flask from the water bath, allow it cool then proceed to add 10 cm 3 of ice water into
the flask
7. Put the flask in the ice water bath for 5 minutes to crystalize the aspirin
8. Add 25 cm3 of ice water into the flask
9. Use a stirring rod to break any lumps if they form
10. Use the glass funnel and the filter paper to filter the mixture
11. Connect the glass funnel to the filter flask connected to the vacuum tram to easily separate the
mixture
12. Scrape and transfer the aspirin into a weighed watch glass
13. Dry the aspirin in the oven for 20 minutes at 95 C
14. Weigh the aspirin

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Reaction mechanism

A mechanism showing the formation of acetylsalicylic acid (Aspirin) from acetic anhydride and salicylic
acid.

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Results
1) Molar mass of SA
C: (12.01g) x 7= 84.07g
H: (1.01g) x 6= 6.06g
O: (16.00g) x 3= 48.00

=138.13g/mol salicylic acid

 
2) Molar mass of Aspirin
C: (12.01g) x 9= 108.09 g
H: (1.01g) x 8= 8.08 g
O: (16.00g) x 4= 64.00 g 

=180.17g/mol aspirin

Since salicylic acid (SA) Is a limiting reagent

1 mol SA 1mole aspirin 180.17 g aspirin

=2g x ( ) x ( ) x ( )
138.13 g SA 1 mole SA 1 mole aspirin
=2.61g theoretical yield

Measured aspirin from the experiment

=2.5g

Therefore

actual yield
Percentage yield= x 100
theoretical yield
2.5
= x 100
2.7
=92.59%

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Discussion

Initially when mixing acetic anhydride and salicylic acid, the mixture becomes colourless, but once boiled
it changes to a semi-brown colour. And also, during crystallization when you add ice cold water int the
mixture, it will eventually change to opaque/ whiteish colour

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Conclusion

From this experiment, I have learnt how to carry out suction filtration in the right way and to be cautious
at all time when handling chemicals and so on. The major experimental findings are that, accuracy and
attentiveness is very important in this experiment to obtain aspirin that is pure. However, there will be
some environmental effects that will still affect the experiment to a small extent.

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