A2 Experiment 13.

5(3) Teachers’ Guide

The Synthesis of Ethyl Ethanoate

 This preparation is a good introduction to equilibrium manipulation and introduces

one of the three methods of making esters.
 Techniques used in this preparation: cooling, distillation, drying, heating using oil and
water baths, use if separating funnels to wash and purify products, drying.
 Ethoxyethane is produced through the reaction of ethanol with concentrated sulphuric
acid, the initial distillate comes over between 65oC and 70oC:

C2H5OH + C2H5OH → C2H5OC2H5 + H2O

 The ether is removed during the final distillation and the first distillate coming over
below 73oC should be discarded.

This is quite a complex preparation and showing the video prior to the experiment
definitely helps. Use Tape 75: 35:05 to 42:59, the timing is in minutes.

Comments on the method

 A twin necked still head should be used with the separating funnel dropping straight
into the 100cm3 flask.
 Students should clamp the 100cm3 flask into a 400cm3 beaker BEFORE pouring in
the oil. 200cm3 each.
 If possible get pupils to set up the apparatus in a single period before the double.
 Pupils find the concept of adding reagent at the same rate as the distillate comes over
difficult.
 Bottoms of flasks and thermometers should be wiped with tissue to remove oil before
putting onto trays.
 After the distillation the apparatus can be disassembled, but the oil should be left in
the beaker to cool.
 Please put all the beakers in one fume cupboard.

Technicians Guide

Issue: Tape 75, Leeds University Organic preparations

Conc. sulphuric acid 2 Bottles
Ethanol 2 Bottles
Glacial ethanoic acid 2 Bottles
Saturated sodium carbonate solution 1 Bottle
Anhydrous calcium chloride lumps 50g – dry in oven overnight
Calcium chloride hydrate (.6H2O) 10g solid per pair
Winchester of yellow paraffin oil
Glass anti-bumping granules
0 – 360oC thermometers
Gloves

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A2 Experiment 13.5(3) Student Sheet

The Synthesis of Ethyl Ethanoate

Theory:

Ethyl ethanoate (ethyl acetate) is an ester. The general method of ester preparation can be
summarised as the reversible reaction: ‘acid + alcohol → ester + water’. Concentrated
sulphuric acid is used to catalyse the reaction and to remove water from the right hand side of the
equilibrium, increasing the yield of ester.

CH3COOH + C2H5OH h CH3COOC2H5 + H2O

Calcium chloride removes water by forming a series of hydrates; it also reacts with
alcohols to form similar compounds, and can thus remove unchanged ethanol in the crude ethyl
ethanoate. The calcium chloride solution added first in step 6 reacts with excess ethanol, when
the solid is added in step 7 it removes water.

Safety:

 Wear goggles and a lab coat. Use gloves for handling organic reagents.
 Perform experiment in a fume cupboard if available.
 When concentrated sulphuric acid is mixed with ethanol considerable heat is evolved - add it
slowly and carefully.
 Glacial ethanoic acid is an irritant and can cause burns.

Method:

1. Pour 10cm3 of ethanol into a 100cm3 round bottomed flask. Put this into a water bath;
carefully add 10cm3 concentrated sulphuric acid and swirl. Wipe off the water from the
flask with tissue paper.

2. Clamp the flask inside an empty 400cm3 beaker supported on a tripod and gauze.

3. Fit a two-necked adapter to the round bottomed flask. Place a separating funnel into the
adapter so that liquid can run vertically down the flask.

4. Put a mixture of 10cm3 ethanol and 10cm3 glacial ethanoic acid in the dropping funnel.

5. Pour about 200cm3 of yellow paraffin oil into a 400cm3 beaker, enough to cover the
initial level of liquid in the 100cm3 flask by about 1cm.

6. Set up the apparatus for distillation with a 0-100 oC thermometer and a small conical flask
to receive the ester.

7. Heat the oil-bath until the temperature reaches 150 oC – measured with 0-360oC
thermometer. Stir regularly with a glass rod. Turn off the Bunsen.
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A2 Experiment 13.5(3) Student Sheet

8. Run about 2cm3 of the mixture in from the dropping funnel. There after run it in at the
same rate as the ester distils over into the collecting flask. The ester will distil over at
between 65o and 75oC. Keep distilling until no more ester comes over. Reheat the oil if
necessary to keep it at 140o – 150oC.

Purification of ethyl ethanoate

9. Remove the distillate and wash with 20cm3 saturated aqueous sodium carbonate solution
in a separating funnel. Discard the lower aqueous layer.

10. Shake the impure ester with a solution made by dissolving 10g hydrated calcium chloride
in 10cm3 water. Separate and discard the lower layer.

11. Stand the ester over a few lumps of anhydrous calcium chloride until the liquid clears –
20 minutes. The liquid may then be filtered or decanted, and distilled in clean dry
Quickfit. Pure ethyl ethanoate boils at 73oC. Note here the boiling point of your sample.

Results:

Temperature of distillation during preparation:…………………………………………………….

Temperature of distillation during purification:……………………………………………………

Comment on the two temperatures above:………………………………………………………….

Mass of ester obtained:…………………………………………………………………………….

Percentage yield calculation;

Volume of ethanol used:……………………………………………………………………………

Mass of ethanol = ……………………………..Moles of ethanol used:…………………………...

Mass of ethanoic acid used:……………………Moles used;………………………………………