Interesterification

Muhammad Asif Ali

Interesterification

• The term interesterification refers to the fats and oils reaction in

which fatty acid esters react with other esters or fatty acids to
produce new esters by an interchange of fatty acid groups.

• Because of the random rearrangement of the fatty acids of the

natural oil, the interesterification process is also commonly referred
to as randomization, rearrangement, or modification.
 Interesterification
• The interesterification processes can alter the original order of distribution of the
fatty acids in the triglyceride-producing products with melting and crystallization
characteristics different from the original oil or fat.

• Unlike hydrogenation, interesterification neither affects the degree of saturation

nor causes isomerization of the fatty acid double bond.

• It does not change the fatty acid composition of the starting material, but
rearranges the fatty acids on the glycerol molecule. The process of
interesterification can be considered as the redistribution of the fatty acids
 Application of Interesterification in US
• Interesterification was not a preferred process in the United States except
for some very specific applications:

(1) Modification of lard to function as a plastic shortening

(2) Random rearrangement of lauric oil based confectionery or coating fats

Types of Interesterification
Types of chemical interesterification or rearrangement processes
practiced are:

1. Random Chemical Interesterification Processes

2. Directed Chemical Interesterification Process

3. Enzymatic interesterification
Chemical Rearrangement
Catalyst
Chemical Rearrangement Catalyst
• Fatty acid rearrangement may occur without the use of a catalyst at a
temperature of 475°F (250°C) or higher, but most processors use alkali
metal alkylates or alkali metals to speed up the reaction.

• Fats reacted at high temperatures without the assistance of a catalyst

proceed slowly to equilibrium and have other undesirable changes as
well (i.e., isomerization, polymerization, and decomposition).
 Examples
Some of the chemical rearrangement catalysts commercially utilized include:

• Sodium methylate

• Sodium potassium alloy

• Sodium or potassium hydroxide

The compounds described above are probably not the real chemical
interesterification catalysts, but serve as initiators in the process of forming
the true interesterification catalyst
 Acid termination losses
a. Catalyst: One gram of sodium methylate catalyst yields the interesterified product,
5.519 grams of methyl esters, 5.67 grams of sodium soap, 2.13 grams of diglycerides.
The loss for the catalyst level used can be calculated as 11.2 pounds product loss for
each pound of catalyst used.

b. Bleaching-earth oil retention: It may be assumed that the bleaching earth will retain
its weight in neutral oil or a 0.1% bleaching earth will remove the phosphate or citric
acid salts and retain 0.1% neutral oil.

c. Deodorizer losses: Deodorization to a 0.05% FFA would necessitate a loss of the FFA
content above this level
 Water termination losses
This neutralization process adds the entrained oil losses experienced with
water washing to those for the acid termination. The only savings for this
procedure are the acid costs; however, the oil quality improvement with
water termination may justify the added expense
Endpoint Control
 Endpoint Control
• A brown color develops when the chemical reaction begins and deepens as
the reaction continues. In most operations, the reaction is allowed to
proceed to a fixed time period after the appearance of brown color before
sampling to determine if the reaction has been completed.

• The reaction is most often confirmed by monitoring changes for a

characteristic particular to the source oil or mixture of oils processed, which
usually involve evaluations for specific product changes.
 Endpoint Control

The effect of interesterification of glyceride mixtures differs in different

cases, depending on the composition of the original fat, mixture of fats, or
prior processing.
 Endpoint Control
Some of the evaluations used to determine interesterification endpoint are
discussed below:
• Melting point
• Fiber Optic Spectrometer Monitoring
• Solids Fat Index
• Differential Scanning Calorimetry
• Glyceride Compositional Analysis
Melting Point
• Interesterification may raise, lower, or have no effect on the melting
point of a fat or oil depending on the starting glyceride composition.

• Common vegetable oils, including soybean, cottonseed, palm, cocoa

butter, and coconut oil, show a rise in the melting point; in contrast,
the melting points of animal fats, such as lard, tallow, and butter fat,
remain unaltered or only slightly lowered after interesterification.
Fiber Optic Spectrometer Monitoring
• A method based on a quantitative measurement of oil spectral
changes after the catalyst (sodium methoxide) addition during
interesterification has been developed.

• This technology monitors interesterification online with a fiber optic

spectrometer, tracks the progress of the reaction, and minimizes the
catalyst dosage and reaction time.
Fiber Optic Spectrometer Monitoring
• To initiate and complete interesterification, the oil absorbance must
reach levels of 0.4 and 1.0 at 374 nm, respectively.

• It is claimed that the reaction time and the dosage of sodium

methoxide can be significantly reduced and that the rearranged oils
have higher oxidative stabilities due to reduced tocopherol
inactivation compared to conventional randomization.
 Solids Fat Index
• Solids fat index (SFI) analysis control requires measurement at several
temperatures for definite results to identify a change, and it is very time
consuming.

• However, small changes in melting point evaluations may be accompanied by

more significant changes in the SFI content and slope for the curve
throughout the range of functionality-important temperatures.

• The changes in trisaturate and desaturate glycerides with interesterification

are reflected in the SFI contents before and after the reaction.
 Solids Fat Index
• SFI analysis are useful for formulation and to confirm that the
predetermined results have been attained, but are probably too time
consuming for interesterification endpoint control.
 Differential Scanning Calorimetry
• Differential scanning calorimetry (DSC) is most useful for studying the kinetics of
crystallization and melting of triglyceride mixtures under dynamic conditions.

• The heating and cooling thermograms resulting from DSC show distinct
differences between some nonrandomized fats and oils. The basis of the cooling
curve is that fat crystals give off heat upon solidifying from liquid oils and absorb
heat upon melting.

• Large crystals give up heat so rapidly during formation that the temperature of
the fat may raise rapidly during the chilling cycle.
 Glyceride Compositional Analysis
• The basic change that occurs due to interesterification is in the glyceride
composition. Therefore, analysis that can identify the glyceride
composition should be the most definite endpoint possible.

• High-performance liquid chromatography (HPLC) methods can separate

triglycerides according to their level of saturation or on the basis of
molecular weighs.