Chapter 5:

Fatty Esters
By : Muhammad Imran Ismail
Faculty of Chemical Engineering,
UiTM Caw. Johor, Pasir Gudang Campus

Lecture 5.1 CHE 321 OLEOCHEMICAL TECHNOLOGY

 Syllabus Content
WEEK CH CHAPTER/CONTENT
1 1.0 Overview on development of oleochemical industries.

2-3 2.0 Oleochemical technology in Malaysia

4-5 3.0 Raw material feedstock for the oleochemical industries.

6-7 4.0 Fatty acids.

8-9 5.0 Fatty Esters.

10-11 6.0 Fatty alcohols.

Latest technology available in oleochemical industries and future
12-13 7.0 challenges.

14 8.0 Plant visit to palm oil refinery.

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 Chapter 5: Fatty Acid

5.1 Production of fatty esters and its derivatives.

5.2 Flow chart

5.3 Uses and application of fatty esters.

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 LEARNING
OUTCOMES
The student should be able to:

• Define fatty esters.

• Describe the production processes of fatty esters and

its derivatives.

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The composition of
fatty esters
 Fatty Esters
Term : Fatty ester is a type of ester that result from
the combination of a fatty acid with an alcohol.

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 What are ester?
• Esters are derived from carboxylic acids. A carboxylic acid contains the -COOH
group

A common ester - ethyl ethanoate

• The most commonly discussed ester is ethyl ethanoate. In this case, the
hydrogen in the -COOH group has been replaced by an ethyl group. The
formula for ethyl ethanoate is:

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 • Notice that the ester is named the opposite way around
from the way the formula is written.
• The "ethanoate" bit comes from ethanoic acid.
• The "ethyl" bit comes from the ethyl group on the end.

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Flowchart & Production of
fatty esters
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 Commercial processes for production of fatty esters are:

(A) Transesterification of oil and fats

(B) Esterification of fatty acids

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(A) TRANSESTERIFICATION
Transesterification:
 Glycerides react with alcohol to produce mixture of fatty acid

ester and alcohol.

 These reactions are
often catalyzed by the
addition of
an acid or base catalyst.

 The reaction can also be

accomplished with the help of
enzymes (biocatalysts)
particularly lipases
 MethylOleate
Recycle of Methanol

FAME
purification

Water
Waste

Methanol By-product
Recovery purification
Column

Glycerol

Base case flowsheet

 3 minutes energy break..

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(B) ESTERIFICATION
 Esterification is a chemical reaction used for making esters. The reaction in which a
Caboxylic acid combines with an alcohol in the presence of a catalyst (commonly
concentrated sulfuric acid) to form an ester [CH3COOC2H5] is called Esterification
reaction. It is a reversible reaction.
 Example:
Acetic acid esterification in excess Ethanol in the presence of concentrated
H2SO4 as a catalyst results in an ester (ethyl actate) with the removal of water
molecule.
 Due to this, esterification reaction is also called 'Dehydration reaction'.
 The chemical composition of the acid, alcohol and catalyst used also affect the rate
of reaction. Strong acid makes the rate of formation of acids very fast.
Direct Esterification of Fatty
Acids with Alcohol
Continuous Esterification Process
• At the top of the column, fatty acid is
introduced while water & excess methanol
are continuously withdrawn bottom of the
column
• Fresh methanol is introduced and methyl
ester is counter current continuously
withdrawn
Different
FAME and Fatty Acid
 DIFFERENCES
Fatty Acid Methyl Fatty Acid
Ester
Non-corrosive Corrosive
Transesterification Fat Splitting
Low Boiling Point and High Boiling Point
Easy to be Distilled

More Heat Stable Less Heat Stable