BRAINCAKEManufacture of Aspirin
Aspirin is a painkiller made by acylating 2-hydroxybenzoic acid (salicylic acid). The OH group on the benzene ring reacts with ethanoic anhydride, turning it into an ester group. The by-product is ethanoic acid.
HOC6H4COOH + (CH3CO)2O → CH3COOC6H4COOH + CH3COOH
Ethanoyl chloride would also work, but industry uses ethanoic anhydride because it is:
• cheaper;
• less corrosive and safer to handle;
• less vigorous in its reaction, so it is easier to control;
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Key terms in this lesson
- atom economy
- The percentage of the total mass of reactants that ends up as the desired product in a reaction.
More in Carboxylic Acids and Derivatives
- Hydrolysis of Esters
- Vegetable Oils and Fats
- Soap Making
- Biodiesel
- Acyl Chlorides
- Acid Anhydrides
- Nucleophilic Addition-Elimination Mechanism
- Acylation of Water, Alcohols, Ammonia and Amines
All 16 lessons in Carboxylic Acids and Derivatives · All AQA A-level Chemistry topics