Interesterification & Hydrogenation

INTERESTERIFICATION

Introduction:
Interesterification is the process of rearranging the fatty esters within and between
triglycerides resulting in most cases, a change in the physical properties of the oil/fat. It is
a useful modification method to give the oil/fat the functionality required for a finished
product. It is applied directly to naturally derived oils/fats or to hydrogenated or
fractioned oil. The effect can be either a random distribution of the fatty acids,
corresponding to the law of probability, or a directed distribution, e.g. by segregation of
the newly formed high melting esters from the reaction mixture through controlled
crystallization during Interesterification.

Process of Interesterification:

The random or chemical Interesterification is the most applied IE modification process of

oils and fats as it is simpler, cheaper and easier to carryout compared to directed or
enzymatic IE. Chemical IE can be carried out by applying the following conditions:
a) Heat at > 300 deg C
b) Heat with caustic soda at 200 deg C
c) Heat with sodium methoxide or ethoxide at 80-100 deg C.
d) Heat with sodium/potassium alloy at 0 deg C.
Of the above options only third and fourth options are widely used in the industry today.
For an optimized IE reaction, the base oil should be in the most refined condition.
Presence of water, fatty acids and peroxides will retard the catalytic activity of the
catalysts. Thus, the oil should be neutralized or deodorized and dried under vacuum prior
to the IE reaction. Water is used to terminate the IE reaction once equilibrium is reached.
The subsequent reaction is washing and drying. The end point of the IE reaction is
determined by observing the colour changes during the operation. Once the reaction is
complete the colour of the oil changes from brown to dark brown.

Effects of Interesterification (IE) on Oils and fats properties:

1. During IE there is no change in the chain length and saturation of the fatty acid.
2. IE may increase or decrease the MP of an oil/fat. Each type of oil/fat or blend has its
own pattern of melting point after IE.Randomization of a blend of oils and fats will
usually have significant difference in the MP of the resultant oil/fat blend. For e.g.
MP of palm oil increases from 39 to 47 after IE.
3. IE also changes the MP behavior of a fat or blend due to the changes in the
triglyceride components. For e.g. cocoa butter which has a sharp melting profile,
changes into a rather flat melting behavior after IE due to the formation of high
melting triglycerides. The table below shows the effect of IE on SFI (solid fat
content) of palm oil. (Before and after IE)

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4. There is no change in fatty acid composition before and after IE.However, the carbon
number of the oil or blend will change as the fatty acids have been rearranged
randomly within and between the triglycerides.
5. Nutritionally IE contributes in many ways, apart from eliminating/reducing trans fatty
acids, the amount of polyunsaturated fatty acids in the cis form is higher, providing
higher essential fatty acid activity.
6. Interesterification also helps to stabilize and increase the amount of desired beta
prime (β’) crystals which are needed for a smooth texture and functional properties as
in case of shortening. An IE blend of palm stearin and sunflower oil has
comparatively more β’ crystals than the direct blend of two.

Attached below are some relevant articles on IEF and its application for detailed study.

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oil and
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interesterification.pdf
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aspects of IEF.pdf ical vs enzymatic IEF.pdf

HYDROGENATION

Introduction:
Hydrogenation is a means of converting liquid oils to semi-solid plastic fats suitable for
shortening and margarine manufacture. Hydrogen gas is added to the double bonds of the
fatty acid moieties on the triglyceride molecules, in the presence of a suitable catalyst
(normally nickel). This results in an increase in the oxidative and thermal stability of the
fat or oil. The gaseous hydrogen reacts with the double bonds of the unsaturated fatty
acid as shown below:
HC=CH + H2---- H2 C-C H2

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Process of Hydrogenation:

For successful hydrogenation, the crude oil is pretreated to remove almost all impurities.
It is degummed, neutralized and bleached and catalyst poisons, phosphatides and soaps
are removed. All hydrogenation process are performed batch wise in cylindrical vessels
of carbon steel constructions and are equipped with a high speed agitator which maintains
the hydrogen gas in finely dispersed bubbles within the circulating hot oil. When the
desired degree of hydrogenation has been attained, as determined by the Refractive index,
the oil is transferred to another tank of same size and allowed to cool. The nickel catalyst
is removed by filtration, which can be aided by addition of small amount of acid activated
earth and citric acid to ensure complete removal of the colloidal nickel catalyst.

The greater the degree of unsaturation of a fatty acid, the greater is its tendency to add
hydrogen. Thus, linolenic acid with three double bonds tends to be hydrogenated before
linoleic acid, which in turn tends to be hydrogenated before oleic acid.

Effect of Hydrogenation:

During the hydrogenation of oils there is a considerable tendency toward the formation of
isomeric unsaturated fatty acids with properties different from the naturally occurring
forms. Such isomers may originate from one or more of the following reactions:
1) Addition of hydrogen at a double bond;
2) Conversion of natural cis to Trans form;
3) Migration of the double bond.

During hydrogenation, there is an increase in the melting point of the fat and hence this
process is also known as hardening. Parallely, there is a reduction in the Iodine value, a
measure of the degree of unsaturation of the oil. Hydrogenation imparts desirable
characteristics such as harder consistency and better oxidation stability which improves a
products’ resistance to rancidity.

Hydrogenation of oil with reduced Trans fat:

The trans selectivity of conventional nickel based hydrogenation catalysts can be

improved by changing the hydrogenation reaction condition. Altering conditions like
lowering the temperature, increasing hydrogen pressure, increasing stirrer speed and
lowering the catalyst loading results in reduced trans fatty acid levels. New catalytic
hydrogenation technologies are being developed to produce HVO with <10% trans fat.
Platinum based catalysts have been shown to reduce formation of trans isomers. Another
approach under development to reduce trans fat levels in HVO is the use of
electrochemical hydrogenation. Attached below is one such article on reduced trans fat in
HVO.

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