ORGANIC

CHEMISTRY LABORATORY
REPORT 8: FISCHER ESTER SYNTHESIS
INSTRUCTOR: PhD. Hoàng Lê Sơn

TEACHING ASSISTANT: Nguyễn Thanh Phong

DATE OF SUBMISSION: 22-07-2019

Group member:

1. Trương Thị Ngọc Hằng - BTBCIU16041

2. Võ Minh Hạnh - BTBCIU16083

3. Nguyễn Hồng Anh Phương - BTBCIU16015

4. Nguyễn Tấn Phú - BTBCIU16057

 I. Abstract
Esters are derived from carboxylic acids involved with the reaction between
carboxylic acids and alcohols in sulfuric acid and tosic acid considered as a
catalyzed. The synthesis of esters were performed by three steps following
reflux reaction, liquid-liquid extraction, and simple distillation. The esterification
of n-butanol with acetic acid under acidic reaction was produced butyl acetate
with an overall 41.8% yield and the boiling point gave 124.6℃.

II. Introduction
Esterification of alcohols with carboxylic acids is one of the most important reactions
in organic synthesis. Acetates are a type of fine chemicals that play a crucial role in
the modern chemical industry such as flavorings in food industry, for solvent
extraction in pharmaceutical industry, textile industry. As a most familiar catalyst,
H2SO4 could used and give high yield.

Figure 1 : The esterification of Butyl acetate
Butyl acetate is an organic compound which occurs naturally in food products.
However, it can also be produced chemically. It is commonly used as a solvent in
the production of lacquers and paints. It is a colorless liquid with a low viscosity,
having a sweet banana-like odor. This liquid is volatile but flammable in
nature. n-Butyl acetate easily dissolves nitrocellulose, a nitric acid ester used in
lacquers. Therefore, it is used as a solvent in the manufacture of nitrocellulose
lacquers.
There were 3 steps to synthesized Butyl acetate in the experiment 8. Fistly,
reflux reaction made the reaction could occur without losing product or
chemical reagent that used in reaction. Secondly, liquid-liquid extraction could
extract Butyl acetate out of samples. Finally, Simple distillation could separate
and purify the esters, and determine the boiling point.

III. Materials and chemicals

1. Materials:
Some equipments which is used for this experiment are n-butanol , acetic acid ,
sulfuric acid solution ( for solvent ) , sodium bicarbonate ( for washing ) ,cylinder
100ml , 10 ml ( for measuring) , beaker with 250ml and 100ml ( for measuring) ,
separatory funnel (250ml), Reflux apparatus and distillation apparatus ( main
equipments)
 2. Methods:
a. Part A: Refluxing
First, the reflux device was ready, including the stand, heating mantle and water
pump. Next, 100mL of n–butanol and 75mL of acetic acid were continually
transmitted into a 100mL clean cylinder into a round bottom flask. Then 5ml of
H2SO4 was closely added using the 10mL cylinder and dropper. After the solution
preparation was finished, the reflux device was finished by clamping the flask in
location and then closely lowering the condenser to the flask and tightly connecting
the junctions. Then the pump was switched on and the water moved inside the
condenser. The batch was permitted to boil for about an hour. Finally, the flask was
removed and cooled down to room temperature or the water bath was used to
decrease temperature but slightly.
b. Part B : Extraction and distillation
At first, the mixture was slowly and carefully transferred into separatory funnel and
clamped into the stand tightly. The first liquid – liquid extraction was performed by
washing the mixture with water for three times. Adding 16 g of sodium bicarbonate
in 200 ml to making solution. This solution was separated to 2 or 3 part to washing
the mixture . There may have pressure inside the funnel, so after shaking, the cap
could be removed for a few seconds to reduce the pressure. Next , getting final
solvent by eliminating the washed solvent. Finally, the sample was weighed before
being transferred for distillation to a round-bottom flask. Distillation apparatus was
set up and the sample was heated to the boiling point of butyl acetate. To remove
the impurities, the first small volume distilled was discarded. The product was
gathered and weighed after distillation to calculate the ester's percentage yield.

IV. Result
The final solution obtained after 3 methods.
Reflux reaction:

Figure 2: reflux reaction allows reaction to occur without changing volume.

Liquid-liquid extraction: washing by cold water and sodium bicarbonate 3 times.

Figure 3: sample was washed with cold Figure 4: sample was washed with
water 3 times sodium bicarbonate 3 times

 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

Simple distillation:

Figure 5: 4 solutions were collected with different range of temperature.
After collecting 3 samples, they were measured the index infraction.
Table 1: infractive index of 3 samples.

Sample 104-116 (oC) 116-123 (oC) 123-124.5 (oC) Average

Infractive index 1.3924 1.3922 1.3923 1.2923

The amount of ester yielded was calculated and compared to theoretical amount.
*Theoretical yield:
CH3COOH + C4H9OH à CH3COOC4H9 + H2O
! !×! !.!"!/!"×!"!"
• The number of CH3COOH: n (CH3COOH) = ! = !
=!"!/!"#
=1.31mol
! !×! !.!"!/!"×!""!"
• The number of C4H9OH: n (C4H9OH)= ! = !
= !"!/!"#
=1.09mol
• The number of ester: n (CH3COOC4H9) = n (C4H9OH) = 1.09mol (because the amount
of acetic acid was excess, so ester was calculated according to alcohol)
• Theoretical amount of ester: m (CH3COOC4H9) = n x M= 1.09mol x 116g/mol=126.4g

*Actual yield:
Total weight of beaker was 92.41g include 47.38g of beaker.

Organic Chemistry Laboratory 5

 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

• Therefore, the amount of ester was 45.03g butyl acetate (92.41g - 47.38g = 45.03g)
!".!"
• % Yield of ester = !"#.! x100 = 35.63%
V. Discussion
In this experiment, three techniques including reflux reaction, liquid-liquid extraction
and distillation were conducted.
In the first part of the reaction while refluxing, sulfuric acid was added to the acetic acid
and butanol solution and the solution turned a brownish pink color. During the reflux
the solution got darker as the reaction progressed and began to have a banana smell,
which indicated that there was production of butyl acetate. This product is an ester that
is colorless and flammable liquid at room temperature. Next, in the separatory funnel,
there were a series of washes in order to extract the butyl acetate from the mixture.
Sodium bicarbonate was added to neutralize the acid. During this step in the
experiment the solution had bubbles of air due to the production of carbon dioxide
from the sodium bicarbonate and thus needed to be vented out. After distillation the
solution turned clear and the banana smell got stronger.
Furthermore, the presence of butyl acetate could be identified not only by characteristic
smell of banana, but also by boiling point determination. In this case, the solution
collected at the end of esterification process had the boiling point of 123-124.5℃, which
closed to the theory index of 126.1℃. Besides, to identify, confirm, and physically and
chemically characterize the final product in Fisher Esterification, some methods like
using high-temperature gas chromatography or mass spectrometry or colorimetric
method could be conducted.
Nonetheless, the esterification reaction of butanol and acetic acid produced butyl
acetate with an overall 35.63% yield. Therefore, some sources of error that were
important to note because they could have influenced the direction of the results. For
example, during the sodium bicarbonate wash stage in the separatory funnel, the cap
flew out while venting and a small amount of the mixture spilled on the countertop.
This incident could have contributed the decrease in the percent yield. In addition, this
experiment addressed two chemistry principles that helped increase the efficiency of
the reaction while minimizing waste in the environment. The first one is that the H2SO4
catalyst was used to speed up the reaction because they are superior to stoichiometric
reagents. Likewise, this experiment provided an organic solvent free procedure, which
prevented waste.



Organic Chemistry Laboratory 6


 International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry

VI. Conclusion
Fischer ester synthesis is widely used in sector as well as in laboratories. In our
experiment, the synthesis of butyl acetate was achieved an acid-catalyzed Fischer
esterification from acetic acid and n- butanol by reflux and liquid-liquid extraction.
Every single step in the synthesis of ester process is important. After the test, the
percent yield of butyl acetate is about 35.63%, and the refractive index of fraction is
approximately with the standard (the refractive index of butyl acetate is 1.341)

VII. Reference
• Organic Chemistry Laboratory Manual of the experiment 5,6,7. Ho Chi Minh:
International University, HCMC, 2018.
• Butyl Acetate by Fischer Esterification from CHEM 121 at Loyola Marymount
University. Ben Johnstone Fruit Smells 2/10/2015

Organic Chemistry Laboratory 7