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Chemistry Practical Investigation Esterification

Kuguneshwry
Purpose:
The purpose of this experiment is to use alcohol(1-butanol) and ethanoic acid to produce
ester.The end product is produced through purification by distillation process.
Background:
Esters are compound which occurs naturally on earth. Esters are liquids that have pleasant odour
of flowers or fruits. Examples are isobutyl propionate which can be found in rum and wherelse
ethyl butyrate can bound in pineapple oil. Animal fats also contains ester linkage.Through
esterification process, ester can be formed from both inorganic and organic acids. Ester are not
soluble in water as esters are organic acid but they can dissolve in organic solvent.Esters are
colourless and have a pleasant odour.Esters which is used for commercial purposes,are used for
fruit additives and essences and also as a constituent of perfumes. Esters are derived from
alcohols and carboxylic acids.Esterification is a process in which hydroxyl group in alcohol and
carboxyl group of an acid is reacted by condensation with the removal of water
molecules.Esterification process are usually slow and high temperatures are used.Water
molecules needs to be removed in this process because esterification is an equilibrium
reaction.Esters are also being used in chemical industries.For example, ethyl acetate, a solvent
which is found in nail-polish remover, and to prevent polymers from becoming brittle, dialkyl
phthalates are used as plasticizers.Esters also plays an important role in medical uses.To treat
asthma, amyl nitrite is used.

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Results
Processes
Session 1:
After reflux

Observation
Bubbling of water occurred,indicating
there is a reaction between alcohol and
ethanoic
acid.If
vaporization
occurs,overheating also occurs and the
flame needs to be adjusted.There is no
colour change present.
Session 2:
The organic product and water do not mix
Isolation with water,H2 O
and they form 2 immiscible layers.
Isolation with sodium carbonate solution, The two immiscible layers of liquids is
Na2CO3
formed.During swirling, hissing sound is
produced. Effervescences is produced.At
the end of the experiment,the ester
collected will be contaminated with
unreacted acid,extracting the product
mixture with sodium bicarbonate(base)
will extract carboxylic acid impurities.
Fraction collected:
Odour
Fruity smell
Apperance
Colourless
Boiling range
122oC-123OC

Discussion
Reflux set-up is used in this experiment .Reflux is a process of heating a mixture in a vessel with
a lie-big condenser. 1-butanol is alcohol as they can be vaporizes easily in air.This volatile liquid
is highly flammable,thus reflux increases the safety of esterification process.At the top of the
reaction vessel, a condenser is set-up as to pass the volatile liquids.The condenser is passed
through with water to condense so the volatile components to condense back to liquid and drop
back into the reaction.Reflux is also set-up to build-up pressure which occurs within a closed
vessel reaction.
Esterification process is a very slow process at room temperature, thus it needs to be cataylsed
by inorganic acids.So, to escalate the yield at the end of reaction, reflux process needs to be setup.The addition of concentration of sulfuric acid,H2SO4 is to act as catalyst to speed up the
esterification process.In addition, H2SO4 forces the equilibrium to the right,which results in
higher amount of yield of ester because it acts as a dehydrating agent which has a strong affinity
towards water molecules.Only 2ml of sulfuric acid ,which is a very little amount used.This is
because large volumes of sulfuric acid is wasteful, causes difficulties in the final step and it is

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uneconomical.Esterification process is conducted at temperatures which are near to the boiling

point of alcohol, thus increasing the rate of reactions.

Equation of esterification:

CH3CH2CH2CH2OH + CH3COOH
1-Butanol

CH3COOCH2CH2CH2CH3 + H 2O

ethanoic acid

1-butylethanoate

water

There are 2 session involved in this esterification process.In the first session:
1.About 30 ml of alcohol(1-butanol) and about 30ml of ethanoic acid in 250ml of the round
bottom flask was placed.
2.2ml of concentrated sulfuric acid is added and 3 boiling chips are added into the solution.Then,
the solution in the round bottom flask is swirled .Boilling chips are added so that the solution
boils at an event rate.
3.A reflux apparatus was set-up and the mixture was set-up for 30 minutes. Let the water
circulate in the condenser(even flow) and the mixture was boiled.The flame was adjusted
throughout the experiment for steady boiling of the mixture.
4.After reflux is completed, the mixture was transferred let to cool down letting the water to
continue to move in the condenser.
Session2:
5. The cooled mixture was the poured into the separating funnel which contains 60ml of distilled
water which was clamped to the retort stand.
6.The separating funnel was closed with a stopper and shaked to allow the formation of two
immiscible layers.The aqueous layer was checked and was discarded using a beaker.
7.The washing process of the organic was repeated by using 60ml of sodium carbonate solution,
N a2 CO3 .After the N a2 CO3 was added in,stop and shake the separating funnel.Gently of the
tip of the separating funnel to allow the CO evolution is no longer vigorous and complete.Allow
2

the layers to separate.The organic phase is the upper part, while the aqueous phase is the lower
part.Allow the aqueous liquid to discard.Effervescence is produced.

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2 CH 3COOH + CO32- 2 CH 3COO- + H 2O + CO 2
CH3COOH + HCO3- CH3COO- + H2O + CO2

8.The process was repeated by washing again with 60ml of distilled water.The aqueous layer was
then discarded again.
9.The organic product was then transferred to a conical flask containing 3 spoons of anhydrous
calcium carbonate,Ca 2 CO3 .The mixture was swirled by covering up using a beaker and allow
the solution to stand for about 10-15 minutes.
10.The organic liquid is then poured into a clean, dry 250ml of round bottom flask and 3 boiling
chips was added.
11.Distillation apparatus was set-up and the ester is distillated from the organic liquid.The
boiling range,colour and odour was recorded.
The boiling range for the distillate is between 1220 C-1230 C.Distillation is an important process
as the mixtures in it can be separated based on their boiling pointsThrough the column,vapors
from the solution are passed through,while the its temperature reduces by the length.Components
with higher boiling points drops back into the solution in the round-bottom flask by
condensation.
A few precaution were taken while conducting this experiment:
1-butanol/ ethanoic acid: It is a flammable vapor and liquid.It is unsafe if this alcohol is draw
into the lungs(respiratory tract irritation).The vapours may cause dizziness,nausea,headache and
drowsiness.May damage the skin tissue/skin irritations/skin dryness or eye infection.Harmful if
swallowed.
Concentrated sulfuric acid,H2 SO4 : is a corrosive causes burns if is spattered in the eyes or on
the skin.To prevent this concentrated acid to spilt on the skin and eyes, long-handed lab coats
and safety goggles are worn through out this experiment. Also, rinse eyes or skins with the
running tap water for at least 10 minutes, see a doctor if needed.
Round-bottom flask: At the end of this experiment, the round-bottom flask would be hot as a
result if distillation.Cool down the glassware before removing.
All the aqueous solutions are disposed into the aqueous water beaker,while ester collected, acids
and alcohol are all disposed into the organic waste container.

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The esters which are obtained at the end of this experiment is low in yield ,a few modification
and step are required to improve the yield and to increase the purity of ester.Since esterification
process is a reversible reaction,reactants and products are in equilibrium,could be a big amount
starting amount,resulting in poor yield of ester. According to Le Chateliers principle,the
equilibrium can be driven to the right,only by putting one of the reactant in excess.Its either
alcohol or acids can be put into excess.Finally, the ester collected is higher in yield.

Systematic and random errors also present in this experiment.First and foremost,the
systematic error detected is the thermometer reading during the distillation of organic mixture is
not accurate as the reading varies between a certain range.This could keep the reaction from
occurring. Random errors detected is during the observation of the scent of the esters were
collected was not accepted. Scents are unique to different people. All this errors could have been
minimized by using a suitable measuring system.
The impacts to environment as a results of the synthesis of ester is :
Octylphenoxypolyethoxyethanol phosphate ester which are the components of pesticides is
toxic, a cholinesterase inhibitors, a known or probable carcinogen, and a pollutant.This chemical
can pollute the clean air.Plants may die as a results of high levels of toxidity.Carbon cycle is
disturbed.
Basically, I felt very happy and extremely satisfied working with my partner. Before the
experiment was carried out, we go through all the procedures together and helped out each other
on things that we did not understand. We brained storm together so that all the procedures will
not be left out. During the experiment is carried out, we divided the task into two.This is done to
avoid hassles when the experiment is conducted. After the experiment is carried out, we cleaned
the tables and rinsed the apparatus together.I am hoping to work with my partner again in future
as I am lucky to get her as a good experiment partner.

Conclusion
Different carboxylic acids and alcohols if combined produces their own ester.This new ester
formed between 1-butanol and ethanoic acid can help food manufacturing companies for
flavoring artificial food.