Use this class practical to produce aspirin in a microscale esterification reaction using phosphoric acid as a catalyst

In this experiment, students prepare aspirin (2-ethanoyloxybenzenecarboxylic acid) from the reaction between salicylic acid (2-hydroxybenzoic acid) and ethanoic anhydride. The esterification reaction is catalysed by phosphoric acid, and forms white crystals.

The practical work should take around 20 minutes.

Equipment

Apparatus

  • Beaker, 10 cm3
  • Hot plate
  • Measuring cylinder, 5 cm3
  • Beaker, 50 cm3
  • Test tube
  • Small filter funnel

Chemicals

  • 2-hydroxybenzoic acid (salicylic acid)
  • Ethanoic anhydride
  • Phosphoric acid (85%)

Procedure

  1. Half-fill a 50 cm3 beaker with deionised water, and heat to 70–80 °C.
  2. Weigh 0.23 g of 2-hydroxybenzoic acid (salicylic acid) into a test tube.
  3. Add 25 drops of ethanoic anhydride followed by one drop of 85% phosphoric acid.
  4. Place in the water bath and leave for 15 minutes.
  5. While still warm add 1.5 cm3 of deionised water (use the measuring cylinder) and cool to room temperature until crystallisation begins, then cool in an ice bath.
  6. Filter through a small filter funnel and recrystallise in a test-tube using a mixture of 0.7 cm3 ethanol and 2 cm3 of deionised water.

Health, safety and technical notes

  • Read our standard health and safety guidance.
  • Wear eye protection throughout (splash-resistant goggles to BS EN166 3).
  • This experiment should be done in a fume cupboard.
  • 2-Hydroxybenzoic acid is harmful if swallowed or in contact with the skin and can cause eye damage.
  • Ethanoic anhydride is CORROSIVE, harmful if swallowed or inhaled and flammable.
  • Phosphoric acid (85%) is CORROSIVE.

Teaching notes

The reaction that takes place in this experiment is illustrated by the diagram below.

A diagram illustrating the reaction and structures of salicylic acid and ethanoic anhydride to produce aspirin

Source: Royal Society of Chemistry

The esterification reaction between salicylic acid and ethanoic anhydride produces aspirin

Observations

This esterification reaction, which uses reactive ethanoic anhydride and phosphoric acid catalyst, is quite fast at microscale. A good yield of white crystals should be formed.

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