ABSTRACT

Synthesis of ethyl acetate by esterification reaction is a study to learn the influence of sulfuric
acid catalyst concentration in synthesis of ethyl acetate by esterification reaction.

In this experiment started with the mixture of acetate acid and alcohol then was done by
esterification reaction in the reflux and distillation process. During the process the sulfuric acid helped to
accelerate the esterification reaction.

The result of this experiment was obtained % yield of ethyl acetate was increasing as the
addition of sulfuric acid to the reaction. For 2 drops of H2SO4 was 26.71%, 4 drops of H2SO4 was 39.89%,
5 drops of H2SO4 was 154.42%.
I. Purpose

The purpose of this experiment was to learn the influence of sulfuric acid catalyst concentration
in synthesis of ethyl acetate by esterification reaction.

II. Theoretical Background

II. 1. Esterification reaction

Esters are compounds of the chemical structure R-COOŔ, where R and Ŕ are either alkyl or aryl
groups. The most common method for preparing esters is to heat a carboxylic acid,R-CO-OH, with an
alcohol, Ŕ- OH, while removing water that is formed. (Zeki and colleagues, 2010)

Figure 1. Esterification Reaction

(murthy, 1981)

II. 2. Factors affecting Chemical Equilibrium

(Govender, 2008)

II. 3. Reflux and distillation

(Gilbert, 2015)

(Kenkel, 2002)
Discussion

In this experiment aimed to learn the influence of sulfuric acid catalyst concentration in
synthesis of ethyl acetate by esterification reaction. Then ethyl acetate was made by esterification
reaction between acetate acid and ethanol which the acetic acid was the carboxylic acid and ethanol
was the alcohol. The principle of esterification reaction was the synthesis of ester compound by
mixturing the carboxylic acid compound with alcohol compound that catalysts an acid and was the
reversible reaction when acetate acid and ethanol were heated then would produce ester and water,
this case was caused the equilibrium reaction. Otherwise, water and ester could produce acetate acid
and ethanol again.

In general, the esterification reaction occurs very slow, thus it needs catalyst such as strong acid
and high temperature. Then, the reaction was using reflux process. Reflux process aimed to accelerate
the esterification reaction by heating without decreasing reactant’s volume. By heating then produced
the termination of double bonds from carbonyl group. Thus, it eased the OH- group to attact the
carbonyl. Then, it was resulted ethyl acetate and water (H2O). Besides reflux process, esterification
reaction then used distillation process that aimed to get pure ethyl acetate by separating the ethyl
acetate and water. The destilation process actually was to separate a substance and solution based on
the difference of boiling point.

There was the mechanism of esterification reaction with acid (H+) catalyst between acetic acid
and ethanol as follows:

DIFOTO

Before heating process of reflux, in the mixtures of acetic acid and alcohol was preceded by
addition of boiling chips. The addition of boiling chips was to spread the heat in all area of the solution,
thus all over the parts are homogenized, if boiling chips didn’t add into the solution then it took a long
time and could get overheating just to the some parts and it could get worse which can explode. After
reflux process, it was continued by distillation process. Before distillation process, the solution was
cooled for a while. The solution that was separated in this experiment was ethyl acetate and water.
Water has 100oC of boiling point and ethyl acetate was about 70oC. During the distillation, the
temperature has to keep at 70oC up to about 10 minutes.

After the distillation process, the solution was added 15 drops of 5% Na2CO3. The addition was
done to neutralize the result of distillation process, because the solution was still in acidic condition.
Thus, It be needed the Na2CO3 to neutralize the solution. After was dropped by the Na2CO3, the solution
was checked its pH by using indicator paper. The pH of solution has to be about 6 – 8. If the solution was
still not reaching about 7 yet, then it had to keep added by the Na2CO3. Na2CO3 was a salt which in the
base condition thus it can attract the rest of acids and produce sodium salt that would dissolved in
water.
 DI FOTO

During the distillation and reflux process, student was using alcohol or Bunsen burner to
produce the high temperature but has to carefully thus it could be overheating when using it.

After that, the result of distillation was put into beaker glass and was added about 3-5 drops
CaCl2. The addition of CaCl2 was aimed to separate the ethyl acetate compound that was used from dirts
that were in the solution. Also, it can make ion Ca2+ could attract carbonate ions that was added before,
thus it was formed precipitate of salts CaCl2 and CaCO3 with colored white.

REAKSI CACL2 DAN CACO3 ADA DIFOTO

After obtained pure ethyl acetate. Ethyl acetate was added by MgSO4 The addition of MgSO4 was to
attract the H2O that it could be still in the ethyl acetate

Reaksi MGSO4 DAN AIR

GRAFIKK.
V. Conclusion

The influence of sulfuric acid catalyst concentration in synthesis of ethyl acetate by esterification
of reaction was as the bigger amount of sulfuric acid that was added, then the bigger of the results of
ethyl acetate. Because, as the bigger amount of catalyst, the reaction would be faster and the reaction
results would be bigger. From the experiment results, the volume of ethyl acetate was increasing by the
increasing of the yield. Although, the second data volume was lower than the first data, that was caused
some error treatment during the experiment.

VI. References

Gilber, J. C., & Martin, S. F. (2015). Experimental Organic Chemistry: A Miniscale & Microscale Approach.
Boston, MA: Cengage Learning

Govender, M., & Hansraj, S. (2008). Turbophysics Grade 12. South Africa: Turbo Publications.

Kenkel, J. (2002). Analytical Chemistry for Technicians, Third Edition. USA: Lewis Publishers

Nathan, S. S., & Murthy, S. K. (1981). Organic Chemistry: Made Simple. London, Great Britain: William
Heinemann Ltd.

Zeki, A., & Al-Hassani, M. H., & Al-Jendeel, H. A. (2010). Kinetic Study of Esterification Reaction.
https://www.iasj.net/iasj?func=fulltext&aId=2335
III. Experimental Methods

III. 1. Tools

The tools in this experiment were beaker glass (100mL), graduated cylinder (50 mL), erlenmeyer
(50mL), watch glass, analytical balance, stirring rod, drop pipette, alcohol burner, Reflux apparatuses
(round bottom flask(50ml), condenser, clamp, and retort stand), Distillation apparatuses(round bottom
flask(50ml), fractioning column, thermometer, retort stand), separatory funnel.

III. 2. Materials

The materials in this experiment were 12.5ml mixtures of acetic acid-ethanol, boiling chips, 5%
Na2CO3, CaCl2 solution, 1 gr MgSO4

III. 3. Procedures

In the first experiment, the 25 mL mixtures of acetate acid and ethanol was put in round bottom
flask. Then the sulfuric acid was added into the 50 ml round bottom flask. The addition of sulfuric acid
was divided into 2 drops for the first experiment then 4 drops for the second experiment and 5 drops of
sulfuric acid for the last experiment. Then boiling chips was added into the round bottom flask.

Each experiment was tested by heating the mixtures in the reflux process. During the reflux
process, the mixtures were heated about 5 minutes. After reflux process, the mixtures were cooled then
was put into the destilation. During the destilation process, the mixtures were heated about 70oC in 10
minutes. After destilation process, the mixtures were neutralized by 5% Na2CO3 gradually, Then was
checked by universal indicator. Each of the experiments has different drops when were neutralized by
5% Na2CO3.

After that, The mixtures were put into separatory flunnel and added CaCl2 saturated solution
gradually to separate the ester layer. Then put the ester layer into 50 mL Erlenmeyer and was added 1
gram of MgSO4. Then the ester or ethyl acetate was put into 10 mL graduated cylinder that was known
its weight by weighing firstly and was obtained its mass. After that, was noted the volume, density, color
and the odor of the ethyl acetate in the practicum report.