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Ethyl Ethanoate Production

Chemistry (Year 12) - Chemical Synthesis

Melanie Gamble

Industrially, ethyl ethanoate is predominately produced in 2 steps.

Step 1: The hydration of ethene to form ethanol in the presence of a phosphoric acid catalyst:

Step 2: Esterification of ethanol with ethanoic acid to produce ethyl ethanoate:

In Step 1, ethanol is produced via the hydration of ethene with steam:

This reaction is both reversible and exothermic, therefore a moderate temperature of 300 - 350°C is used to make a compromise between the reaction rate and yield.

The reaction has a ratio of 2 gas moles of reactants to 1 gas mole of products, therefore a high pressure of 60 - 70 atm is used to maximise both the reaction rate and yield of the reaction.

The use of the phosphoric acid catalyst also increases the overall reaction rate.

In the chemical industry, Step 1 (to produce ethanol) occurs accross two reaction chambers.

Initially, the ethanol and steam are pumped into a chamber at a temperature of 300 - 350°C and a pressure of 60 - 70 atm.

They are then passed through layers of silica mesh coated with a phosphoric acid catalyst to produce ethanol.

Any unreacted reagents are then pumped into a second chamber, where they are cooled. Ethanol has the lowest boiling point and can be collected at the bottom of the chamber. The leftover ethene and steam are cycled through the system again to obtain a higher yield.

A schematic of industrial ethanol production is depicted below:

Now that ethanol has been formed we can move on to the next step.

In Step 2, ethanoic acid is reacted with ethanol in the presence of a sulfuric acid catalyst to produce ethyl ethanoate. This is an esterification reaction.

As this reaction only involves aqueous species, it occurs at room temperature and atmospheric pressure.

Industrially, this reaction takes place in large distillation chambers so that the ethyl ethanoate can be distilled off as soon as it is formed, to prevent the reverse reaction from occurring.

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