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Making Scents of Esters

Mark Riley

Introduction Esters have a very sweet fruity smell. Naturally occurring esters are found in fruits.
An ester is a product of the reaction of an acid (usually organic) and an alcohol (the
hydrogen of the acid R-COOH is replaced by an alkyl group R'). Esters mainly result
from the condensation (a reaction that produces water) of a carboxylic acid and an
alcohol. The process is called esterification. This reaction can be catalyzed by the
presence of H+ ions. Sulphuric acid, H2SO4, is often used as a catalyst for this
reaction. Esters have the general formula R-COOR.

Task Practical Report

Aim Produce three different esters by using a range of carboxylic acids and alcohols.
Determine the ester formed by using the smell given off by the products and the
chemical equations for the three different reactions.

Details Ethanoic acid was used as the carboxylic acid for all three reactions. The alcohols
used were ethanol, methanol and propanol. The reaction of ethanoic acid with
ethanol will be discussed in detail and results and equations will be given for all
three reactions.

Mark Riley 3107631608 Making Esters from Alcohols and Acids Chem 4 - Lesley Hirst 1
THE EXPERIMENT

Procedure

1. Place 1 drop of concentrated sulphuric acid in a test tube


2. Add 10 drops of ethanoic acid (or propanoic acid) to the sulfuric acid in the tube.
3. Add 10 drops of ethanol (or other alcohol) to the mixture.
4. Put about 10 cm3 of water into the 250 cm3 beaker. Carefully lower the tube into the beaker so
that it stands upright.
5. Heat the beaker gently on a tripod and gauze until the water begins to boil, then stop heating.
6. Stand for 1 minute in the hot water. If the mixture in the tube boils, use the tongs to lift it out of
the water until boiling stops, then return it to the hot water.
7. After 1 minute, carefully remove the tube and allow it to cool.
8. When cool, pour the mixture into a test-tube half-full of 0.5 M sodium carbonate solution. There
will be some effervescence. Mix well by pouring back into the specimen tube repeat if necessary.
A layer of ester will separate and float on top of the aqueous layer.
9. Smell the product by gently wafting the odour towards your nose with your hand do not put your
nose near the top of the tube!
10. Repeat this procedure for up to three more different esters. Compare the odours of the different
esters prepared by your group and by other groups. Write word equations for each reaction, and
(for advanced students) chemical equations using structural formulae.

Equipment

Safety glasses
test tubes
dropping pipettes
250mL beaker
test tube rack
Bunsen burner
heat resistant mat
tripod
gauze
retort stand
chemicals.

Mark Riley 3107631608 Making Esters from Alcohols and Acids Chem 4 - Lesley Hirst 2
RESULTS

Test 1.

An ester is formed whenever a carboxylic acid reacts with an alcohol. In this first reaction, the alcohol used
was ethanol and the carboxylic acid used was Ethanoic Acid. A small amount of concentrated H2 SO4
(Sulphuric Acid) was used as a catalyst. H2 SO4 is a dehydrating agent and removes water from the
products. The alcohol (ethanol) loses OH and the carboxylic acid (ethanoic acid) loses a H. The method
used for this reaction is only suitable for preparing small amounts and the ester formed in this reaction
could only be characterised by odour.

Prior to mixing the solutions an equation was written for the reaction and ethyl ethanoate was predicted
as being the ester that would be formed.

Once this reaction was complete, the ester could not be determined as the strong odour given off by
unreacted ethanol made it impossible to smell the actual ester. The experiment was performed again with
much care given to the accuracy of measurements. This time the ester formed could easily be smelt and
group members agreed that the odour was very similar to nail polish remover. After some investigation, it
was confirmed that the aroma given off by ethyl ethanoate is of nail polish remover (although some
believe it to smell like pear).

ethanol + ethanoic acid ethyl ethanoate + water.


C2H5OH(aq) + CH3CO2H(aq) CH3CO2C2H5(aq) + H2O(l)

Mark Riley 3107631608 Making Esters from Alcohols and Acids Chem 4 - Lesley Hirst 3
RESULTS

Test 2.

Alcohol used- Methanol

Carboxylic Acid used- Ethanoic Acid

Smell- Paint/Glue (similar to ethyl ethanoate)

methanol + ethanoic acid methyl ethanoate + water.


CH3OH(aq) + CH3CO2H(aq) CH3CO2CH3(aq) + H2O(l)

Test 3.

Alcohol used- Propanol

Carboxylic Acid used- Ethanoic Acid

Smell- Pear

propanol + ethanoic acid propyl ethanoate + water.


C3H7OH(aq) + CH3CO2H(aq) CH3CO2C3H7(aq) + H2O(l)

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QUESTIONS

Question 1.

This method is only suitable for the preparation of small samples for characterization by odour. If you
wanted to prepare enough ester for characterization by boiling point you would need to use a different
technique.

Production of an ester on a larger scale.

1. Add ethanol, ethanoic acid and very small amount of sulphuric acid (dependent on the amount of
carboxylic acid & alcohol used) to a flask and attach a Liebig condenser. See figure 1.
2. Bring the mixture to a boil under reflux for 1 hour using a suitable heat source such as a heat
mantle or oil bath. (open flame not recommended) Using this boiling point to determine or confirm
the ester is unreliable as alcohols (& even small chains of carboxylic acids) can have boiling points
close to and sometimes even lower than esters (ethanol has a very low BP of 78.1C vs ethyl
ethanoate BP 77.1C ), especially if the ester is very large (long chain).
3. Remove the heating source and allow mixture to cool to room temperature.
4. Pour the mixture into a separating funnel and add a small amount (Approximately the same volume
as the mixture) of cold water. Rinse the reaction flask with 5-10 mL of water and also add that to
the separating funnel See figure 2.
5. Gently shake the separator funnel (attach stopper first), allow to rest, then remove the aqueous
layer leaving only the organic layer.
6. Add sodium bicarbonate solution to the separating funnel which will extract any remaining acid
and again form an aqueous layer which will then again be removed. Check that the aqueous layer
removed is basic and if not repeat this step until it is.
7. Rinse again with a small amount of water and let separate. (adding aqueous sodium chloride can
help in layer separation. Remove the lower aqueous layer and again discard it.
8. When the water has been removed, pour the ester from the top of the separating funnel into
another reaction flask. See figure 3.
9. Assemble a distillation apparatus with a thermometer attached and distill the ester into a cooled
receiver. Carefully watch the thermometer so the boiling point can be noted and the ester can be
confirmed as ethyl ethanoate (Boiling point is approximately 77.1C) or to determine the ester if
the alcohol and carboxylic acid are unknown.

Figure 1. Figure 2. Figure 3.

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QUESTIONS

Question 2.

Which industries might use synthetic esters? Why?

Food industry- Flavouring of food in particular of lollies & sweets. Also margarine & preservatives.

Cosmetic industry- Create nice smelling perfumes and add pleasant aromas to other products such as
shampoos and lotions such as

Beverage industry- To give drinks nice flavours such as cordials.

Alcohol industry- Again to add flavor. Most obviously the uses such as Propyl-2-methylpropanoate in
Rum.

Medicines- Especially childrens medicines to add nice fruity flavours.

Clothing industry- Synthetic fibres such as polyester.

Energy industry- Such as to make biodiesel fuels.

Mechanical industry- Such as use as lubricants on machinery.

Question 3.

Why do many living things produce esters?

Living things store much of their energy as esters, known as fats or oils. Many of the flavours and odours of
fruits are esters. The formation and breakdown of esters are reactions that occur frequently in living
things. Esters are part of the basic building blocks for all lipids and are a component of phospholipids and
fats. They assist in function and integrity of healthy skin, cholesterol metabolism, and prostaglandin
production. Esters help maintain resilience and lubrication of all cells. They break up cholesterol deposits
on arterial walls, thereby preventing hardening of and within the arteries. Esters are necessary for the
function of the thyroid and adrenal glands. Carnivorous plants (such as the Venus Fly Trap) produce esters
to attract pray as do many flowers produce esters to attract bees.

(Tutorvista 2009: Internet; HSC Online 2007: Internet)

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Bibliography

Bibliography

NSW HSC online., 2007, Estrification, [online], available from:


http://www.hsc.csu.edu.au/chemistry/core/acidic/chem935/chem935net.html [30 October 2009]

TutorVista., 2008, Esters, [online], available from: http://www.tutorvista.com/search/esters [31 October


2009]

Organic Chemistry Portal., 2007, Fischer Esterification, [online], available from: http://www.organic-
chemistry.org/namedreactions/fischer-esterification.shtm [30 October 2009]

Great site for drawing chemistry diagrams easily http://www.emolecules.com

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