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OBJECTIVES

To convert Ethanol to Ethyl Acetate (Ethyl Ethanoate).

MATERIALS

Apparatus

Chemicals

Round bottom flask


Water/Liebig condenser
Retort stand
Separating funnel
Thermometer
Beakers
Conical flasks
Bunsen burner
Stoppers
Tripod stand
Rubber tubes
Analytical balance
Ice bath

Ethanol
Glacial Acetic Acid
Concentrated Sulphuric Acid
Anti-bumping granules
30 % Sodium Carbonate solution
Calcium Chloride
Granular anhydrous Calcium Chloride
Distilled water

PROCEDURE

50 mL of both 95 % ethanol and glacial acetic acid were mixed in a 250 mL round-bottomed
flask.

10 mL of concentrated H2SO4 was slowly added.


Make sure that the mixture

With cooling and shaking.

is homogenous.
The flask was fitted with a reflux water-condenser and was boiled gently for 10 minutes. The
flask and its contents were cooled.

The position of the condenser was rearranged for distillation and boiling chips were added in
the flask. A filter flask (whose side arm is joined to a rubber tube leading over the edge of
laboratory bench) was used as a receiver.
Ethyl

Acetate

is

highly

flammable!!!
About 2/3 of the mixture was distilled off.

The distillate was transferred to a separating funnel and about 25 mL of 30 % Na 2CO3


solution was added.

Funnel was stoppered, inverted and shaken, and the stopcock was opened from time to time.

The two layers were allowed to separate and the lower layer was removed.
Ensure that sodium carbonate is
removed

as

completely

as

possible.
25 g of calcium chloride was prepared in 25 mL of water.

The solution was shaken vigorously and was allowed to separate. The lower layer was
removed as completely as possible.

The Ethyl Acetate was moved into a small conical flask. A few lumps of granular anhydrous
calcium chloride were added and the liquid was shaken until it is clear.

Some anti-bumping granules were decanted to the liquid.


Arrange for distillation (with a
0~100C thermometer in the
apparatus)
The receiving flask was pre-weighed. The distilling flask was placed in a cold water bath
which is gradually heated.

The ether formed at 35 ~ 45 C was distilled off (may be discarded). The heating continued
and the fraction that boils between 74 ~ 79 C was collected.

Product was weighed and the % yield was calculated.

RESULTS

Volume of ethanol
Weight of ethanol
Volume of acetic acid
Weight of acetic acid
Theoretical yield

:
:
:
:
:

50
39.45
50
52.5
75.45

Weight of receiving flask


Weight of product + Receiving flask
Weight of Ethyl Ethanoate (Actual yield)
Percentage yield

:
:
:
:

*Calculations are shown in Appendix.

mL
g
mL
g
g

33.96
79.18
45.22
59.9

g
g
g
%

DISCUSSION
The apparatus was arranged in such a way to obtain the expected product which is
Ester (C3H8COO) through Esterification. In the Esterification process, the reactants used,
Acetic Acid (CH3COOH) and Ethanol (C2H5OH) were mixed, together with an acid catalyst,
which is Sulphuric Acid (H2SO4) by which undergo a reflux reaction to form Ester
(C3H8COO) and Water (H2O). From that, the Ester (C3H8COO) obtained was purified through
several purification processes in which required distinctive arrangements of the apparatus that
undergo the same reflux reaction. Hence, pure Ester (C3H8COO) was acquired.
H2SO4

CH3COOH

+ C2H5OH

C3H8COO + H2O

From conducting the experiment, the weight of Ethanol (C2H5OH) and Acetic Acid
(CH3COOH) were obtained by using a simple formulation, formula 1.1 (shown in Appendix).
After the weight of both Ethanol (C 2H5OH) and Acetic Acid (CH3COOH) were achieved, the
limiting reagent (Ethanol) was determined in order to identify the theoretical yield of Ethyl
Ethanoate (C3H8COO). The theoretical yield obtained for Ethyl Ethanoate (C 3H8COO) was
75.45 g. By the end of the experiment, the actual yield of Ethyl Ethanoate (C 3H8COO) was
obtained which has an amount of 45.22 g. In addition, from achieving the theoretical yield
and the actual yield, the percentage yield was then calculated which resulted with 59.9 %.
It was observed that there were two layers in the separating funnel and the bottom
layer, which was Sodium Carbonate, was removed to acquire the Ester (Ethyl Ethanoate,
C3H8COO). Next, it was observed that the ester underwent several purification processes
which are distillation, separation, evaporation. It was also observed that, during the boiling
process, pure Ester (C3H8COO) was distilled into the flask when the temperature was in
between 74 C 79 C.

There are many errors that might occur during the experimentation process which will
drastically influence the results obtained. One of the errors might be caused by physical
errors (caused by experimenters). The lack of efficiency and focus of the experimenters in
conducting the experiment would strongly affect the results especially in recording down
readings. Furthermore, during the experiment, the rearrangement of the apparatus might have
taken too much time thus resulting in the evaporation of the substance. From that, the actual
yield did not synchronize well with the theoretical yield calculated. Moreover, parallax error
and misreading of the analytical balance might contribute to the errors during the process of
experimentation. For instance, the actual volume needed for Ethanol was 50 mL but the
volume measured was only 46 mL. Thus, the mass weighed ended with a different amount in
which affects the end result.

CONCLUSION
As a conclusion, I have learned that Ester could be obtained when Carboxylic Acid is
added together with Alcohol with the aid of an acid catalyst through the Esterification
process, in this case, Acetic Acid (CH3COOH) and Ethanol (C2H5OH) with Sulphuric Acid as
the catalyst. It was observed that the results acquired support the theory on the conversion of
Ethanol to Ethyl Ethanoate. Furthermore, it was observed that pure Ester was obtained when
the thermometer is at the level between 74 C 79 C. A percentage yield of Ethyl
Ethanoate of 59.9 % was able to recover from the Esterification process. From that, the
objective of the experiment has been achieved based on the results and the quantity of Ester
(Ehtyl Ethanoate) that had been gained.
To achieve maximum precision and accurate results, the possible errors that might
occur during the experiment have been strictly controlled. The process of weighing the
Ethanol and Acetic Acid was carried out with intensive caution to avoid any errors in the
experiment which will drastically affect the end results. Not just that, parallax and physical
errors that might be caused by the experimenters have also been controlled by confirming the
measured samples with team members. By the end of the experiment, we were able to acquire
pure Ester through the Esterification method and this would definitely improve our technical
and laboratory skills. Moreover, this experience would really affects us in terms of efficiency
and competency in dealing with laboratory equipments as a Chemical Engineering
Technologist in the future.

TUTORIAL
Post Laboratory Questions
[1]
a) Write and balance the equation for the reaction of acetic acid with
ethanol to produce ethyl ethanoate and water.
H2SO4

CH3COOH

+ C2H5OH

C3H8COO + H2O

b) In the reaction of above example, how many grams of ethyl


ethanoate would be produced if 50 ml of ethanol were react with 50
ml acetic acid? Which is the limiting reagent?
(given ethanol:
0.8 g/ml and acetic acid : 1.06 g/ml and ethyl acetate: 0.9 g/ml).

Mass of Ethanol

ethanol =

Mass of Acetic Acid

mass
volume

acetic acid =

mass
volume

mass = ethanol volume

mass = acetic acid volume

mass = (0.8)(50)

mass = (1.06)(50)

mass = 40 grams

mass = 53 grams

Limiting Reagent

40 g CH3CH2OH

1 mol CH 3 COOH
1 mol CH 3 CH 2OH

1 mol CH 3 CH 2 OH
46.02 g CH 3 CH 2OH

Only 52.17
g of Acetic

60.02 g CH 3 COOH
1mol CH 3 COOH

8
= 52.17 grams of CH3COOH

Acid were used to react with 40 g Ethanol. Hence, Ethanol is the limiting
reactant.

c) Calculate the percentage yield if 50.0 g of ethyl ethanoate was


obtained from the experiment.

40 g CH3CH2OH

1 mol CH 3 CH 2 OH
46.02 g CH 3 CH 2OH

1 mol CH 3 COOCH 2 CH 3
1mol CH 3 CH 2 OH

76.03 g CH 3 COOCH 2CH 3


1mol CH 3 COOCH 2CH 3
= 66.08 grams of CH3COOCH2CH3

actual yield

Percentage yield = theorytical yield 100


%
=

50.00 g
66.08 g

100 %

= 75.66 %

[2]What is the function of reflux water condenser?


A reflux water condenser is a Liebig condenser arranged vertically above
the reaction flask; vapours are condensed and returned to the flask, the
contents of which can therefore be boiled for long periods without any loss
of material.

[3]Why must the concentrated sulphuric acid be added slowly and with
cooling?
The concentrated sulphuric acid on dilution gives out a lot of heat; the
slow addition with cooling is needed to avoid splashing if the mixture gets
hot.

[4]What is the function of sodium carbonate solution and anhydrous


calcium chloride?

10

( Sodium Carbonate )The distillate contains a very small of ethanoic acid


and maybe some sulphuric acid.
Sodium carbonate solution removes
this.

(Anhydrous Calcium Chloride ) The solid calcium chloride is a dehydrating


agent; it removes any remaining a very small of water from the product.

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[5]Explain the phenomena of 2 layers formed in the separating funnel.

A separating funnel is used in liquid-liquid extractions to separate the


components of a mixture between two immiscible solvent phases of different
densities. Liquids, such as oil and water can be separated by using a
separating funnel. The mixture is put into a separating funnel, shaken and
allowed to settle. The liquid with higher density, in this case water forms the
lower layer. Remove the stopper and open the tap after standing. The water
runs out through the tap. The oil remains in the funnel and can be run out into
another beaker.

Separating funnel is a used in liquid-liquid extractions to separate (partition)


the components of a mixture into two immiscible solvent phases of different
densities. Typically, one of the phases will be aqueous, and the other a nonpolar lipophilic organic solvent. All of these solvents form a clear delineation
between the two liquids. The two layers formed are usually known as the
organic and aqueous phases. Most organic solvents float on top of an
aqueous phase, though important exceptions are most halogenated solvents.
The organic solvent used for the extraction must not react with the substance
to be extracted or with water. It should also have a low boiling point so it can
be easily removed from the product.

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REFERENCES

[1] [Anonymous, 2013], http://en.wikipedia.org/wiki/Ethyl_ethanoate,


[13.3.2013]

[2] http://www.blurtit.com/q591973.html, [13.3.2013]

[3] http://en.wikipedia.org/wiki/Separatory_funnel, [13.3.2013]

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APPENDIX
Calculations (RESULTS)

m = V
At V = 50 mL, = 789 kg/m3

Mass of ethanol ( C2H6O ) =

789

kg
g
1 m3

1000

( 50 mL )
3
kg 106 mL
m

= 39.45 g of ethanol

At V = 50 mL, = 1.05 g/cm3

Mass of acetic acid ( C2H4O2 ) =

1.05

g
10 6 cm 3

( 50 mL )
cm3 106 mL

= 52.5 g of acetic acid

Limiting Reactant

1 mol ethanol
1 mol acetic acid 60.05 acetic acid

=51.42 g acetic acid


(39.45 g ethanol 46.08
g ethanol
1mol ethanol
1mol acetic acid )

39.45 g ethanol only reacted with 51.42 g acetic acid, thus having excess acetic acid.
Ethanol is the limiting reactant.

Theoretical Yield

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1 mol ethanol
1 mol ethyl ethanoate 88.105 g ethy l ethanoate

(39.45 g ethanol 46.068


g ethanol
1mol ethanol
1 mol ethyl ethanoate )
75.45 g ethyl ethanoate

Weight of Ethyl Ethanoate ( Actual Yield )


79.18 33.96 = 45.22 g

Percentage Yield

Yield
45.22 g
100 =
100 )=59.9
( T hActual
eoretical Yield
75.45 g

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