Assignment 4.2 Making a nail varnish remover.
Ethyl Ethanoate
Properties:
Ethyl Ethanoate is the product of the reaction between ethanol and acetic acid. It
has a melting point of -84ºC and a boiling point of 77ºC which means it is a liquid
at room temperature. It is a colourless liquid, it is highly miscible with all
common organic solvents, which make it a common solvent for cleaning and
paint removal.
Found in alcoholic beverages, fruit juices and beer ethyl ethanoate has a fruity
scent that can be commonly recognised in glues, nail polish remover and
cigarettes.
Due to its agreeable aroma and low cost, this chemical is commonly used and
manufactured in large scale in the world.
Uses in industry.
Ethyl Ethanoate is useful in many industries due to its “fruity” smell and
colourless appearance.
Industry Applications Role/benefit
Flavour and essence Food Flavour Used largely to prepare
bananas, pineapple and
grape scent food fl avours.
Chemical manufacture Producti on of acetamide, Organic chemical raw
acetyl acetate, methyl materials
Cosmeti cs Aroma enhancer In perfume to enhance
aroma
Paint manufacture Solvent Dissolve and dilute the
paints
Methods of production in industry:
In industry a continuous process is used to maximise efficiency as it is a
continuous process in which the product process is not interrupted, the product
can then be further processed.
The main method to produce ethyl ethanoate involves the esterification of
ethanol with acetic acid.
A mixture of acetic acid with ethanol and sulphuric acid is preheated in a small
amount and fed to an esterifying column where it is refluxed. The mixture then
goes to a second refluxing column where a ternary azeotrope containing 85%
ethyl acetate is removed. The distillate is then mixed with water after which it
separates into two layers. Top layer is directed to a refluxing column from which
the residue containing 95% ethyl ethanoate is distilled to remove any impurities.
-Fischer method
Ethyl acetate is traditionally synthesised from by heating ethanol with ethanoic
acid in the presence of a catalytic amount of a strong acid such as sulphuric acid.
Page 1 of 8
, Fischer esterification is a special type of esterification by refluxing a carboxylic
acid and an alcohol in the presence of an acid catalyst.
CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O
The reaction can be accelerated by acid catalysis.
-Tishchenko reaction
Reaction of acetaldehyde using aluminium triethoxide as a catalyst.
2 CH3CHO → CH3COOC2H5
This method has been proposed by two different routes; (i) dehydrogenative
process, which uses copper or palladium-based catalyst and (ii) the oxidative
one, which employs, PdO supported catalysts.
Making ethyl ethanoate in the laboratory
Aim: Prepare a sample of ethyl ethanoate.
Apparatus:
-50cm3 round bottom flask -Condenser -15cm 3
ethanol
-Anti-bumping granules -Electric mantle or hotplate
-1cm3 concentrated sulfuric acid -10cm 3 glacial ethanoic acid
Method
- Add 10cm3 of glacial ethanoic acid with 15cm3 ethanol to the round bottom flask
-Add a couple of anti-bumping granules(this will stop the reaction from getting
too vigorous)
-Attach the flask to the condenser
-Connect condenser to the cold water to allow water to flow
-heat up using electric mantle
-Reflux for 30 minutes
-Turn the heat off and allow to cool.
Testing the purity of ethyl ethanoate
Purity
Purity is an element that contains a single substance without any other element
altering it.
Why do we test for purity?
-Purity can have a significant impact on the chemical properties of a substance.
It can reduce melting point or increase melting point
A pure Substance can form predictable results from chemical reactions, That is
why when researching chemists use substances of high purity.
Page 2 of 8
Ethyl Ethanoate
Properties:
Ethyl Ethanoate is the product of the reaction between ethanol and acetic acid. It
has a melting point of -84ºC and a boiling point of 77ºC which means it is a liquid
at room temperature. It is a colourless liquid, it is highly miscible with all
common organic solvents, which make it a common solvent for cleaning and
paint removal.
Found in alcoholic beverages, fruit juices and beer ethyl ethanoate has a fruity
scent that can be commonly recognised in glues, nail polish remover and
cigarettes.
Due to its agreeable aroma and low cost, this chemical is commonly used and
manufactured in large scale in the world.
Uses in industry.
Ethyl Ethanoate is useful in many industries due to its “fruity” smell and
colourless appearance.
Industry Applications Role/benefit
Flavour and essence Food Flavour Used largely to prepare
bananas, pineapple and
grape scent food fl avours.
Chemical manufacture Producti on of acetamide, Organic chemical raw
acetyl acetate, methyl materials
Cosmeti cs Aroma enhancer In perfume to enhance
aroma
Paint manufacture Solvent Dissolve and dilute the
paints
Methods of production in industry:
In industry a continuous process is used to maximise efficiency as it is a
continuous process in which the product process is not interrupted, the product
can then be further processed.
The main method to produce ethyl ethanoate involves the esterification of
ethanol with acetic acid.
A mixture of acetic acid with ethanol and sulphuric acid is preheated in a small
amount and fed to an esterifying column where it is refluxed. The mixture then
goes to a second refluxing column where a ternary azeotrope containing 85%
ethyl acetate is removed. The distillate is then mixed with water after which it
separates into two layers. Top layer is directed to a refluxing column from which
the residue containing 95% ethyl ethanoate is distilled to remove any impurities.
-Fischer method
Ethyl acetate is traditionally synthesised from by heating ethanol with ethanoic
acid in the presence of a catalytic amount of a strong acid such as sulphuric acid.
Page 1 of 8
, Fischer esterification is a special type of esterification by refluxing a carboxylic
acid and an alcohol in the presence of an acid catalyst.
CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O
The reaction can be accelerated by acid catalysis.
-Tishchenko reaction
Reaction of acetaldehyde using aluminium triethoxide as a catalyst.
2 CH3CHO → CH3COOC2H5
This method has been proposed by two different routes; (i) dehydrogenative
process, which uses copper or palladium-based catalyst and (ii) the oxidative
one, which employs, PdO supported catalysts.
Making ethyl ethanoate in the laboratory
Aim: Prepare a sample of ethyl ethanoate.
Apparatus:
-50cm3 round bottom flask -Condenser -15cm 3
ethanol
-Anti-bumping granules -Electric mantle or hotplate
-1cm3 concentrated sulfuric acid -10cm 3 glacial ethanoic acid
Method
- Add 10cm3 of glacial ethanoic acid with 15cm3 ethanol to the round bottom flask
-Add a couple of anti-bumping granules(this will stop the reaction from getting
too vigorous)
-Attach the flask to the condenser
-Connect condenser to the cold water to allow water to flow
-heat up using electric mantle
-Reflux for 30 minutes
-Turn the heat off and allow to cool.
Testing the purity of ethyl ethanoate
Purity
Purity is an element that contains a single substance without any other element
altering it.
Why do we test for purity?
-Purity can have a significant impact on the chemical properties of a substance.
It can reduce melting point or increase melting point
A pure Substance can form predictable results from chemical reactions, That is
why when researching chemists use substances of high purity.
Page 2 of 8
