Preparation of Banana flavor from isoamyl acetate via

Fisher esterification

Bala, Diana Patricia D., Balasabas, Ruth Marienelle R. *, Baustista, Kenneth Patrick T.,
Cabalonga, Allyssa Jiselle M.

College of Science, University of Santo Tomas, Espana Blvd, Manila.

Abstract

Isoamyl acetate is an ester which has a banana flavor characteristic. Esters can be synthetically
produced via the Fisher reaction which is an acid-catalyzed reaction of and alcohol and a carboxylic acid.
The objective of this experiment is to produce the assigned ester specifically isoamyl acetate or banana
essence via fisher reaction and calculate its percent yield. There are two experimental methods involved in
the production of isoamyl acetate. The first method is the reflux, where in the reaction of isoamyl alcohol
and acetic anhydride was carried out with the presence of sulfuric acid as the acid catalyst to produce
isoamyl acetate. And the second method is the liquid to liquid extraction of the desired product from the
mixture using a separatory funnel. At the end of this experiment, 2.2302g of isoamyl acetate was produced
and the percent yield of the isoamyl acetate was calculated. The calculated percent yield is 74.80%.

Introduction

Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl

alcohol and acetic anhydride. Esters are a group of organic compounds derived from an

alcohol and a carboxylic acid and generally possess a distinctive odor. Most organic

fragrances and fruit flavors belong to this class of compounds. Consequently, these

compounds are not used in body perfumes because generally, esters are unstable to

perspiration and tends to break down forming carboxylic acids which possess unpleasant

odor. Isoamyl acetate has a strong odor which is also described as similar to that of a

banana and a pear. It is one of the most important flavor compounds used in food

industries because of its banana flavor characteristic. Esters can be synthetically

produced through the Fischer reaction. The synthesis of Esters via Fisher reaction or
Fisher esterification is an acid-catalyzed reaction of an alcohol and a carboxylic acid. In

this experiment, isoamyl acetate or the Banana essence is produced from the reaction of

isoamyl alcohol and acetic anhydride.

Esters are obtained by refluxing a carboxylic acid and an alcohol in the presence

of an acid catalyst. Refluxing a reaction mixture is a simple and efficient way to maintain

a constant reaction temperature. Reflux refers to an experimental method that involves

heating a reaction mixture to the boiling point temperature of the reaction solvent and

inducing the solvent to re-condense back into the reaction flask using a condenser. The

advantage of this technique is that the mixture can be left for a long period of time without

the need to add more solvent or the fear that the reaction vessel will boil up to the extent

of drying because any vapor is immediately condensed back into the reaction flask.

On the other hand, extraction is another experimental method specifically a

separation technique that was used is this experiment. Extraction is separating or

removing a compound from a solid or liquid mixture using a solvent. There are two types

of extraction, the solid phase extraction and the liquid-liquid extraction. Solid phase

extraction is a technique designed for rapid, selective sample preparation and purification

prior to chromatographic analysis. While liquid to liquid extraction is separating

compounds based on their relative solubilities in two different immiscible liquids. In liquid-

liquid extraction, a solution containing a mixture of compounds is shaken with a second

solvent that is immiscible with it. The compounds in the mixture then distribute between

the two liquid layers or phases. The two layers will be separated using a separatory funnel

to obtain the needed product.

 The objective of this experiment is to produce the assigned ester isoamyl acetate

or banana essence via fisher reaction and calculate its percent yield.

Methodology

The Methodology of this experiment is divided into three parts, the preparation of

reactants, the reflux set-up and the liquid-liquid extraction.

Preparation of the Reactants

2.5mL of isoamyl alcohol and 2.6mL of acetic anhydride was placed in 2 separate

clean and dry test tubes and was transferred into an ice bath. After the ice bath, 3 drops

of concentrated sulfuric acid (H2SO4) was added to acetic anhydride. The mixture was

then slowly added to the test tube containing isoamyl alcohol in a dropwise manner.

The Reflux Set-up

The mixture of acetic anhydride, sulfuric acid and isoamyl alcohol was poured into

the reflux setup. The reflux set-up used in this experiment comprises of a condensing

system at a 90-degree angle with the reaction flasks. Two pieces of boiling chips were

added to the mixture in the reflux set-up. The mixture was placed into 70°C to 80°C water

bath for 30 minutes. After 30 minutes, the mixture was removed from the reflux set-up

and was cooled for 1 minute. The mixture was then transferred to a small beaker with

crushed ice. When the ice has completely melted, the mixture was transferred into a

separatory funnel.

Liquid-liquid Extraction
 The mixture was added with 15mL saturated sodium bicarbonate (NaHCO3) and

bubbles began to form. The separatory funnel was covered and swirled after the bubbling

ceased. After the swirling, the mixture had two layers; the upper layer and the lower layer.

The lower layer of the mixture was drained and discarded. On the other hand, the upper

layer was added with 15mL saturated sodium chloride (NaCl). The separatory funnel was

covered and swirled. The resulting mixture again had two layers. The lower layer was

drained and discarded. While, the upper layer was transferred to a clean and dry beaker

containing a 1/2 spatula sodium sulfate (Na2SO4). The resulting liquid was decanted. The

residue was discarded while the decantate or the extracted isoamyl acetate was

transferred into a vial using a dropper and was weighed. Lastly, the percent yield was

calculated.

Results and Discussion

2.5mL isoamyl alcohol and 2.6mL acetic anhydride was used in this experiment.

The reason for this is to force the equilibrium to the right. Excess of either the carboxylic

acid or the alcohol must be used to drive the equilibrium to the right in order to get a

decent yield of the ester product. Each step of the reaction mechanism of fisher

esterification is reversible and, therefore, the reaction reaches equilibrium. Le Chatelier’s

principle suggests that the amount of ester produced in an equilibrium reaction might be

increased either by using an excess of one of the reactants or by removing one of the

products. In practice, an excess of carboxylic acid or alcohol, whichever is more readily

available, is added, and/or water is removed as the reaction proceeds.

 The synthesis of Esters via Fisher reaction or Fisher esterification is an acid-

catalyzed reaction of an alcohol and a carboxylic acid. In this experiment, concentrated

sulfuric was added to acetic anhydride acid to serve as the acid catalyst of the reaction.

Also, Fischer esterification is conducted at reflux. The purpose of reflux is to heat

a reaction mixture at its boiling temperature to form products, without losing any of the

compounds in the reaction flask. A condenser is set vertically into the top of the reaction

flask. Any compound that vaporizes will condense when it enters the cool environment of

the reflux condenser and will then drain back into the reaction flask. The reflux set-up

used in this experiment comprises of a condensing system at a 90-degree angle that

allows condensed solvent to go back to the reaction pot.

Going back to the reflux set-up part of the methodology, boiling chips were added

before heating the reflux set-up in a water bath. A boiling chip is a tiny, unevenly shaped

piece of substance added to liquids which allows more calm boiling. The pores inside

these boiling chips provide cavities both to trap air and to provide spaces where bubbles

of solvent vapor can form. These bubbles ensure even boiling and prevent bumping and

boiling over and loss of the solution. But remember never add a boiling chip to a solvent

which is already hot, because it can cause the solvent to boil over violently.

The prescribed temperature in heating the mixture is 70°C to 80°C for 30minutes.

This serves the purpose of further increasing the rate of reaction. Since, the fisher

esterification is reversible, maintaining the temperature in the range of 70°C to 80°C

prevents the reaction from reversing. The time used in heating the mixture allows more

ester to be produced.
 Swirling the separatory funnel gently allows the distinction of the two liquid layers;

the organic/upper layer and the aqueous/lower layer. On the other hand, extracting with

saturated sodium chloride (NaCl) solution is used to remove water in the organic solution

because water will affect the process of distillation. While, extracting with sodium

bicarbonate (NaHCO3) neutralizes or removes the excess acetic anhydride and any

sulfuric acid (H2SO4) present in the organic layer of the mixture. Finally, mixing sodium

sulfate (Na2SO4) is used to form solid residues in order to separate the desired liquid

product, isoamyl acetate.

Table 1: Summary of Results

At the end of the experiment, 2.2302g of isoamyl acetate was synthesized through

the fisher esterification of isoamyl alcohol and acetic anhydride. This amount of the

product is called the actual yield. It is obtained by subtracting the weight of the empty vial,

which is 12.7717g from the weight of the vial with the extracted isoamyl acetate (banana

essence), which is 15.0119g. The calculated theoretical yield is 2.9816g (Figure1).

Lastly, the calculated percent yield is 30.61% (Figure 2).

Figure 1: Computation of the Theoretical yield.

Figure 2: Computation of the Percent yield.

Conclusion

Isoamyl acetate is an ester that possess an odor similar to that of a banana and

was synthesized through the fisher esterification of isoamyl alcohol and acetic anhydride.

Esters are produced by refluxing a carboxylic acid and an alcohol in the presence of an

acid catalyst. After the reflux, series of the liquid to liquid extraction must be done to obtain

the liquid product, isoamyl acetate or the banana essence. The percent yield was

calculated through the obtained actual yield of 2.2302g and the calculated theoretical

yield of 2.9816g. The percent yield of the isoamyl acetate produced is 74.80%.
References

Books

Solomons, G., Fryhle, C., & Synder, S. (2014) Organic Chemistry. United States

of America: John Wiley & Sons, Inc.

Christian, G., Dasgupta, P., & Schug, K. (2014) Analytical Chemistry. United

States of America: John Wiley & Sons, Inc.

Online Sources

Preparation of Isoamyl Acetate. (n.d.). Retrieved February, 07, 2016, from

http://www.umsl.edu/~chickosj/Ch263/Isoamyl%20acetate.pdf.

Synthesis of esters using acetic anhydride. (n.d.). Retrieved February, 07, 2016,

from http://course1.winona.edu/tnalli/spring05/209labs/expt5.pdf.

Synthesis of Isoamyl Acetate Using the Fisher Esterification. (n.d.). Retrieved

February, 07, 2016, from https://www.allbestessays.com/Science/Synthesis-of-Isoamyl-

Acetate-Using-the-Fischer-Esterification/9166.html.

Organic Chemistry Laboratory Reflux. (n.d.). Retrieved February, 07, 2016, from

http://www.organicchem.org/oc2web/lab/exp/lp/lpreflux.html.

Extraction (Chemistry) (n.d.). Retrieved February, 08, 2016, from

https://en.wikipedia.org/wiki/Extraction_(chemistry).

Liquid to liquid extraction. (n.d.). Retrieved February, 08, 2016,

fromhttps://en.wikipedia.org/wiki/Liquid%E2%80%93liquid_extraction.
 Extraction. (n.d.). Retrieved February, 08, 2016, from

http://orgchem.colorado.edu/Technique/Procedures/Extraction/Extraction.html.

Boiling Chips. (n.d.). Retrieved February, 07, 2016, from

http://orgchem.colorado.edu/Technique/Procedures/Distillation/Boilingchips.html.

Isoamyl acetate. (n.d.). Retrieved February, 07, 2016, from

https://en.wikipedia.org/wiki/Isoamyl_acetate.

Fisher-Speier esterification. (n.d.). Retrieved February, 08, 2016, from

https://en.wikipedia.org/wiki/Fischer%E2%80%93Speier_esterification.