ORGANIC CHEMISTRY PRACTICUM REPORT
MODUL V
ESTERIFICATION OF ETHYL ACETATE/METHYL ACETATE
Group 2/Thursday
Name: Muhammad Fazle Mawla Rendra
NRP : 5008241010
Name: Ahdiaska Rizqy Emilulfata
NRP : 5008241006
Lecturer
Name : Dr. Orchidea Rachmaniah, S.T., M.T
NIP : 197802142003122001
Name : [Link]. Raden Darmawan, S.T., M.T
NIP : 197805062009121001
Date of Experiment : 10 April 2025
Date of Susbmission Report : 10 April 2025
ORGANIC CHEMISTRY LABORATORY
CHEMICAL ENGINEERING
FACULTY OF INDUSTRIAL TECHNOLOGY
AND SYSTEMS ENGINEERING
INSTITUT TEKNOLOGI SEPULUH NOPEMBER
2025/2026
TABLE OF CONTENT
OBJECTIVE ....................................................................................................................... 3
THEORY ............................................................................................................................. 3
METHODS .......................................................................................................................... 4
ANALYSIS AND DISCUSSION ........................................................................................ 5
CONCLUSION ................................................................................................................... 5
OBJECTIVE
1. Synthesize ethyl acetate or methyl acetate by reacting ethanol with oxalic acid in the
presence of sulfuric acid as a catalyst, with heating.
2. Perform distillation to isolate the ester product.
3. Measure the density and determine the concentration of ethyl/methyl acetate in the
distillate.
4. Compare the effectiveness of using excess ethanol versus excess acetic acid in the
reaction.
THEORY
Esterification is a fundamental organic reaction where a carboxylic acid reacts
with an alcohol to form an ester and water. This is a reversible equilibrium reaction and
is typically slow without a catalyst. Concentrated sulfuric acid serves as a dual-purpose
catalyst in this process—it increases the rate of reaction by protonating the carbonyl
oxygen, making the carbonyl carbon more electrophilic, and it removes water from the
reaction mixture to drive the equilibrium forward (Fessenden & Fessenden, 1986). The
general reaction is:
CH₃COOH + ROH ⇌ CH₃COOR + H₂O
Le Chatelier’s principle states that the position of equilibrium will shift to
oppose any change made to the system. Therefore, the addition of excess alcohol or
removal of water promotes ester formation (Geankoplis, 2003). This concept is utilized
to enhance product yield in equilibrium-limited reactions.
The experimental setup includes reflux, which allows the reaction to occur at a
constant temperature without loss of volatile components. The reflux condenser ensures
that vaporized reactants and products are condensed and returned to the reaction
mixture, which is crucial for maintaining reactant concentration and ensuring full
conversion (Atkins & de Paula, 2010).
After ester formation, distillation is used to separate the ester from unreacted
reagents based on boiling points. For instance, ethyl acetate (boiling point ~77.1°C) and
methyl acetate (boiling point ~57.1°C) can be separated effectively from acetic acid
(boiling point ~118°C) and ethanol (boiling point ~78.4°C) (Yaws, 2015).
The distillate is further characterized by measuring its density, which is an
important physical property for verifying compound identity. Literature values for ester
densities include 0.900 g/cm³ for ethyl acetate and 0.932 g/cm³ for methyl acetate at
room temperature (Yaws, 2015).
Two versions of the experiment were conducted—one using excess alcohol and
another using excess acetic acid. This allows a comparison of how shifting reactant
concentrations influences the yield and efficiency of the esterification process. The role
of equilibrium control in chemical synthesis and process engineering is thereby
illustrated (McCabe, Smith & Harriott, 2005).
METHODS
The experiment began with assembling a reflux setup using a two-neck round-
bottom flask fitted with a thermometer and a reflux condenser. A mixture of 10 mL of
glacial acetic acid and 100 mL of ethanol or methanol was added to the flask. After
stirring the mixture briefly, 1 mL of concentrated sulfuric acid was added slowly to
catalyze the reaction.
The flask was heated on a hot plate until a constant reflux temperature was
reached (~71°C). The mixture was maintained under reflux for two hours, allowing the
reaction to proceed while avoiding the loss of volatile compounds.
Upon completion, the reaction mixture was cooled to room temperature and
transferred to a distillation setup. The mixture was gradually heated, and the distillate—
primarily the ester—was collected around its expected boiling point (~77°C for ethyl
acetate). The distillate was collected in a pre-weighed container for later density
determination.
Density was measured using a pycnometer. First, the mass of the empty
pycnometer was recorded. It was then filled with the ester, and the mass was recorded
again. Using the known volume of the pycnometer
This procedure was repeated with a new mixture where the acetic acid was in
excess instead of the alcohol. Both trials were used to compare the influence of reactant
ratios on the ester yield.
ANALYSIS AND DISCUSSION
The esterification reaction successfully produced esters with distinct fruity
odors, characteristic of compounds like ethyl acetate and methyl acetate. The presence
of these odors along with the colorless appearance of the distillate indicated successful
synthesis and initial purification. This qualitative confirmation was supplemented by
density measurements.
The experiment demonstrated the efficiency of using sulfuric acid as a catalyst
and dehydrating agent. The reaction mixture was kept under controlled conditions via
reflux, which helped maintain constant temperature and minimized reactant loss. These
precautions are standard in organic synthesis and help ensure reproducible results.
Distillation technique worked effectively due to differences in boiling points of
the products and remaining reactants. Literature-supported physical data were useful in
identifying the compounds collected. The measured densities closely matched standard
values for ethyl acetate and methyl acetate, further confirming the identity and relative
purity of the synthesized esters (Yaws, 2015).
The use of excess ethanol significantly increased the yield of ester product
compared to the trial with excess acetic acid. This observation supports Le Chatelier’s
principle. Increasing the concentration of ethanol, a reactant, shifted the equilibrium
toward ester production. This reinforces the idea that manipulating concentrations is a
valuable strategy for increasing product yield in reversible chemical reactions (Atkins
& de Paula)
The experiment also emphasizes the importance of operational techniques in
organic chemistry. Refluxing, distillation, and density analysis are foundational
methods in both educational and industrial labs. The ability to measure the success of
a chemical reaction using both qualitative and quantitative methods provides a
comprehensive understanding of the reaction process.
CONCLUSION
In this experiment, esters such as ethyl acetate and methyl acetate were
successfully synthesized through acid-catalyzed esterification of acetic acid with
ethanol or methanol. The use of concentrated sulfuric acid played a critical role in
catalyzing the reaction and shifting the equilibrium by removing water.
Reflux ensured controlled heating, and distillation enabled effective separation
of the ester product. Density measurement confirmed the identity of the esters
synthesized. Comparing the use of excess ethanol versus excess acetic acid highlighted
the practical application of Le Chatelier’s principle.
Greater ester yield was observed with excess alcohol, confirming the principle’s
predictive value in chemical equilibrium. The experiment effectively demonstrated the
synthesis, purification, and analysis of esters while reinforcing core chemical
engineering and organic chemistry principles.
REFRENCES
Atkins, P., & de Paula, J. (2010). Physical Chemistry (9th ed.). Oxford: Oxford
University Press.
Fessenden, Y., & Fessenden, R. (1986). Kimia Organik (3rd ed.). Jakarta: Erlangga.
Fieser, L. F. (1992). Organic Experiments (7th ed.). Toronto: DC Heath and Company.
Geankoplis, C. J. (2003). Transport Processes and Separation Process Principles (4th
ed.). New Jersey: Prentice Hall.
McCabe, W. L., Smith, J. C., & Harriott, P. (2005). Unit Operations of Chemical
Engineering (7th ed.). New York: McGraw-Hill.
Yaws, C. L. (2015). The Yaws Handbook of Physical Properties for Hydrocarbons and
Chemicals (2nd ed.). Houston: Gulf Publishing Company.