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Manufacturing ethyl ethanoate

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A document to discuss the process of manufacturing ethyl ethanoate.

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August 19, 2019
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Manufacturing Ethyl ethanoate



Word equation:

Sulfuric acid

Ethanoic acid + ethanol  ethyl ethanoate + water

Sulfuric acid is used as a catalyst and heat is used to increase the rate of reaction.

A catalyst is used for this reaction as it speeds up the rate of the reaction without adding any
substance to the reaction. This is used in this reaction as this reaction is very slow so it speeds up the
process.

This is because organic compounds have low boiling points. Due to this, the compounds may turn to
vapour is exposed to high levels of heat. To prevent this, a reflux reaction is carried out. The reflux
reaction allows the compound to reach its boiling point and turn to vapour, yet when it reaches the
top of the column it will turn to liquid and fall back down. This process then repeats itself
continuously.

1. At the end of the reflux ethyl ethanoate and impurities are found in the round bottom flask.

Suggest what these 4 impurities may be:

1) Unreacted Ethanol

2) Sulphuric acid

3) Ethanal

4) Water (this is one of the products)

2. Water is added to the ethyl ethanoate and impurities.

a) What property do organic liquids have when mixed with water?

When mixed with water, they separate into two different layers.

b) Why do they separate into 2 different layers?

This is due to the liquids having different densities.

c) What happens to the impurities?

The impurities are still in the solution and so the ester that is produced is impure. These impurities
are separated through a series of measures which are separating techniques which will allow the
solution to be purified. The solution is moved to a second refluxing column where azeotrope
containing 85% ethyl acetate is removed. Water is then mixed with the distillate after when it
separates into two layers, which the top layer is fed to a refluxing column from which the residue
containing 95% ethyl acetate is distilled. This removes the impurities.

5) Sodium carbonate solution is added to ethyl ethanoate to remove an impurity.

a) Which impurity does sodium carbonate react with?

It reacts with any ethanoic acid impurities.
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