CHM401L - Research Proposal

Group 8 – 1MBIO3
Peralta Mark Nhel, Pondoc Charisse Mae, Quizon Ma. Abigail & Del Rosario Mikaela Katherina

A. Proposal Title.

Synthesis of Butyl Acetate via Esterification

B. Research Objectives

The objectives of this experimental research are to synthesize butyl acetate via esterification process, apply
the knowledge gained in the past four modules including the proper use of different techniques, methods and
processes for the synthesis of a particular compound and come up with a useful product out of this synthesis. Through
the experiment, the step-by-step process of esterification and its importance will be learned. Synthetic route of butyl
acetate is essential, as to other synthesis of organic compounds, thus acquiring the methods on how to make this
helps in knowing how to integrate it as additives to products that have synthetic fragrances and flavorings.

C. Literature Review

Butyl acetate, also known as butyl ethanoate, is an organic compound that is commonly used as a solvent in
the production of lacquers and other products. Because of its apple scent, it is also used as a synthetic fruit flavoring
in foods. Butyl acetate is an ester found in many types of fruit, where along with other chemicals it imparts
characteristic flavors (PubChem, n.d.). Synthesis of butyl acetate can be done easily as it involves common chemicals
and the methods that can be used are systematic.

The ester group is an important functional group that can be synthesized in a number of different ways. The
low-molecular-weight esters like butyl acetate have very pleasant odors and indeed are the major components of
the flavor and odor aspects of some fruits. Although the natural flavor may contain nearly a hundred different
compounds, single esters approximate the natural odors and are often used in the food industry for artificial flavors
and fragrances. For example, butyl acetate, as aforementioned, is an ester that is characterized as a strong aroma
and flavor in apples (Williamson, 2016).

Esters can be prepared by the reaction of a carboxylic acid with an alcohol in the presence of a catalyst such
as concentrated sulfuric acid, hydrogen chloride, p-toluene sulfonic acid, or the acid form of an ion exchange resin
(Williamson, 2016).

The most renown method of synthesizing ester is through Fischer esterification. This process uses carboxylic
acid and an alcohol that reacts in the presence of an acid catalyst to form an ester and water. The reaction mechanism
of acetic acid and 1-butanol to form butyl acetate via esterification is shown in the equation below:

RCO2 H + HOR′ → RCO2 R′ + H2 O

carboxylic acid alcohol ester water

The mechanism of the reaction involves initial protonation of the carboxyl group, attacked by the
nucleophilic hydroxyl, a proton transfer, and loss of water followed by loss of the catalyzing proton to give the ester.
Because each of these steps is completely reversible, this process is also, in reverse, the mechanism for the hydrolysis
of an ester (WSU, n.d.).

According to Ujhelyi & Modra (2012), the direct esterification process is a reversible reaction that can result
to a reaction known as equilibrium, between a carboxylic acid and an alcohol; wherein it goes very slowly, pointing
to the direction of the formation of the ester. The reaction time is slow, but the yield of the product may be increased
by increasing the concentration of the reactants. To hasten the reaction, it has to be conducted at the boiling point
of the mixture, which is accomplished by doing a reflux setup. Strong acids can also be used to catalyze the reaction,
but its presence does not affect the amount of product (Suryawanshi et al., 2014).

This experimental research will be dealing with the synthesis of butyl acetate via esterification process. After
mixing together the starting chemicals - acetic acid, n-butanol and H2SO4 catalyst - the mixture will undergo refluxing,
to make sure the reaction has gone to completion. Several step-by-step procedures such as simple distillation method
to distill the final product and ‘washing’ using separatory funnel are designed to isolate the ester product as a pure
substance, that is free from any leftover starting materials and acetic acid side product. This is a typical, though
relatively simple, organic synthesis procedure. The volume of the product obtained, i.e. the yield, will be measured
and the percent yield will be determined. The synthesized esters will also be assessed for their fragrance and may
be incorporated to products that has scent.
D. Research Methods

This experimental research will use esterification process to synthesize butyl acetate from butanol and acetic
acid. Refluxing and simple distillation method will be conducted to obtain the final product. Butan-1-ol, glacial acetic
acid, concentrated sulfuric acid, anhydrous sodium sulfate and sodium bicarbonate are the chemicals that will be
involved in the synthesis.

Procedure: In a 100-mL round-bottom flask, which is placed under an ice bath, 15 mL of glacial acetic acid and 11.5
mL of butanol will be introduced respectively. Then, 2 mL of concentrated sulfuric acid will be carefully added to the
mixture. A stirrer bar if available, or a few boiling chips will be put, and a water condenser lubricated with grease will
be fitted with the flask. The mixture will be refluxed for 45 minutes, time upon which the reaction mixture will then
be transferred into a separatory funnel. 20 mL of distilled water will be used to initially wash the organic layer. This
will be done twice. The aqueous layer will be isolated, and the organic layer will be washed again, this time, using
saturated sodium bicarbonate. The organic layer will be transferred in a beaker and excess water will be removed by
adding anhydrous sodium sulfate. The product will be decanted, and it will be placed in another round-bottom flask
with stirrer bar for the simple distillation process. Tared container should be prepared and when the distillates start
to come out, first few drops will be disregarded, and the rest will be gathered. The final product will be weighed in
order to calculate the percentage yield.

E. Timetable

Target Tasks Activity by Weeks

February March April May

Stages

3 4 1 2 3 4 1 2 3 4 1 2 3

Literature search
1

Proposal writing/ Teacher

consultations
2

Experimental
3

Summary report writing

4

Project presentation
5

F. References

Acetic acid & 1- butanol mechanism image. Retrieved from

https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Book%3A_The_Basics_of_GOB_Chemist
ry_(Ball_et_al.) /15%3A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives/15.07_Preparation_o
f_Esters

PubChem (n.d.) Butyl Acetate. Retrieved from https://pubchem.ncbi.nlm.nih.gov/compound/Butyl_acetate

Suryawanshi, M. A., Shinde, N. H., & Nagotkar, R. V. (2014). Kinetic Study of Esterification Reaction for the Synthesis
of Butyl Acetate. Retrieved from https://www.ijert.org/research/kinetic-study-of-esterification-reaction-
for-the-synthesis-of-butyl-acetate-IJERTV3IS10139.pdf

Ujhelyi, R. P., & Modra, D. (2012). Comparison of Three Synthesis Methods. Annals of West University of Timisoara,
21(2), 57-65. Retrieved from
http://www.elearningchemistry.ro/awut/userfiles/magazine1_acc/57_65_UjhelyiR_MdraD.pdf

Williamson K.L. (2016). Synthesis of Butyl Acetate. Macroscale and Microscale Organic Experiments. Retrieved from
https://www.scribd.com/doc/150540581/Preparation-of-Butyl-Acetate-pdf

Winona State University. (n.d.) Experiment 5, Organic synthesis: Fischer Esterification. Retrieved from
http://course1.winona.edu/tnalli/fall02/209expt5.pdf