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Trans Fatty Acids in Oil Modification

The document discusses the modification of fats and oils through processes like fractionation, interesterification, and hydrogenation to enhance their stability and functionality. Fractionation separates triglycerides based on melting points, while interesterification alters the molecular composition without changing fatty acid content, improving physical properties. Hydrogenation adds hydrogen to unsaturated fatty acids to create more solid fats, but can produce trans fats, which are linked to health risks.

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0% found this document useful (0 votes)
21 views11 pages

Trans Fatty Acids in Oil Modification

The document discusses the modification of fats and oils through processes like fractionation, interesterification, and hydrogenation to enhance their stability and functionality. Fractionation separates triglycerides based on melting points, while interesterification alters the molecular composition without changing fatty acid content, improving physical properties. Hydrogenation adds hydrogen to unsaturated fatty acids to create more solid fats, but can produce trans fats, which are linked to health risks.

Uploaded by

Mykey Abiy
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd

3.

Modifications of Fats & Oils


• Why modification?
• it is desirable or necessary to convert or transform highly unsaturated
refined oils into more saturated forms;
– for greater oxidative stability or altered physical forms of plastic and solid fats
– for physical stability, and functional properties of fats and oils, and their fractions
• Fractionation, interesterification and hydrogenation (hardning) will be
considered
Fractionation
• Fractionation allows the separation of triglycerides of different melting
points or solubility and the gain of one or more stearin or olein fractions
from a fat and oil
• Oils and fats are a mixture of triacylglycerols, i.e., triple esters of glycerol
with different fatty acids.

1
Cont’d
• Therefore, fats and oils are not chemically homogenous
substances but a mixture of different triglycerides; hence
– each of these triglycerides has a defined melting point, influencing the physical
properties of the others.
• Fractionation uses this property of fats, i.e., being a mixture of
different substances of the same class.
• This enables one to separate a fat into fractions that are products of
different melting ranges.
• Fractionation is used mainly to improve functionality and/or
improve the commercial value, and to produce special products.
• The oil that is predominantly fractionated is palm oil.
• Palm oil is especially suitable for this technique because of its
composition, i.e, two almost equal parts of saturated and unsaturated
fatty acids that can very easily be separated in to an olein and a
stearin fraction. 2
Inter-esterification

• Inter-esterification of oil changes its molecular composition.


• Oils or fats are mixture of various triacylglycerol molecules having
different fatty acids and positional distribution.

• Treating oils and fats with sodium methoxide as a catalyst at 80 ˚C


causes intermolecule ester exchange, changing the molecular
composition, while leaving the fatty acid composition unchanged.

• As a result, the oil changes its physical properties such as melting


point and consistency.

3
Cont’d
• Eg. Improvement of natural lard (pig fat).
• Natural lard tends to form a rough crystal, which is difficult to handle,
during storage. This is because 64% of palmitic acid is attached to 2nd
position of triacylglycerol molecules.
• Randomizing the positional distribution of fatty acids of natural lard by
interesterification improves its physical property, making it a smooth
“rearranged lard”.
• Another example of interesterification is in the field of margarine
production.
• Interesterification of soybean oil and completely hydrogenated
soybean oil provides a material for margarine. This rearranged oil has
an advantage that it does not contain trans fatty acid, because it is
not made through partial hydrogenation.

4
Inter-esterification of triacylglycerol molecules

5
Fatty acid distribution is randomized, resulting in the change of the physical property of the oil
Cont’d
• Two types of inter-esterification are available, i.e. chemical and
enzymatic.
• In the food industry, intere-sterification can be carried out using a
chemical catalyst or an enzyme.
• Sodium methoxide is generally used as a catalyst in chemical
esterification, while lipases are used in enzymatic esterification.
• Chemical inter-esterification is a random reaction while enzymatic
inter-esterification can be random or regiospecific.

6
Comparison of interesterification methods
Chemical interesterification Enzymatic interesterification
1. Low processing cost (batch High processing cost (continuous
reactor) plug-flow reactor, lipase)
2. High processing loss (oil Minimum processing loss
saponification)
3. Low oxidative stability (tocopherol No change in oxidative stability
loss)
4. High levels of reaction by-products Low levels of reaction by-products
(MAG, DAG, glycerol)
5. Flavor reversion problem No flavor reversion
6. Highly reproducible and easily More complex operation and control
controlled

7
Hydrogenation
• Hydrogenation is the process of adding hydrogen to unsaturated fatty
acids to reduce the number of double bonds. The purpose of
hydrogenation is twofold:
– To convert liquid oils to semisolid or plastic fats
– To increase the thermal and oxidative stability of the fat, and thus the
shelf life
• Hydrogenation of unsaturated fatty acid occurs when hydrogen gas is
reacted with oil under controlled conditions of temperature and pressure,
and in the presence of a nickel, copper catalyst.
• As the reaction progresses, there is a gradual production of trans fatty
acids that increases the melting point of the fat or oil and creates a more
solid product

8
Cont’d
• A typical example of hydrogenation is in the process of margarine and
shortening production.

• Vegetable oil is hydrogenated with gaseous H2 in the presence of a metal


catalyst (usually nickel catalyst).

• If the hydrogenation is completely performed, all the double bounds are


converted to the saturated ones with the same carbon number.

• For example, complete hydrogenation of linoleic acid (18:2-6) generates


stearic acid (18:0).

9
Cont’d

Hydrogenation

Complete hydrogenation of linoleic acid, giving stearic acid

10
Cont’d
• Vegetable oil is too soft for margarine or shortening because it is liquid.
• Saturated fat obtained by complete hydrogenation is too hard.
• Margarine requires something in the middle, i.e. not too hard and not too
soft.
• Margarine and shortening makers “partially hydrogenate” their product.
• They only add hydrogen atoms until the oil is at the desired consistency.
• When they stop the incomplete hydrogenation process, unsaturated fatty
acids are in varying stages of hydrogenation.
• Some molecules are mostly hydrogenated, while others are not. And the
double bonds have often shifted to unnatural positions, resulting in the
generation of trans fatty acids or trans fat, which is thought to increase risk
of coronary heart disease.

11

Common questions

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Inter-esterification affects the nutritional profile of fats and oils by altering their physical properties without changing the fatty acid profile, thus not introducing trans fats, which is a significant advantage over partial hydrogenation . This process maintains the overall nutritional quality while improving usable properties like texture and stability for food applications. Unlike hydrogenation, which can produce unhealthy trans fats, inter-esterification allows for creating products like margarine that do not negatively impact health through trans fat intake .

Fractionation involves separating triglycerides based on different melting points or solubility, which allows the extraction of different fractions like stearin or olein from fats and oils, primarily to improve functionality or commercial value . In contrast, inter-esterification involves altering the molecular composition by redistributing fatty acids within triglyceride molecules, which modifies physical properties such as melting point and consistency, without changing the fatty acid composition. This can be done chemically or enzymatically and is used to prevent trans fat formation in products like margarine .

The primary purpose of modifying fats and oils through methods like hydrogenation and inter-esterification is to enhance their oxidative stability and alter their physical properties to suit specific applications. Hydrogenation converts liquid oils into more solid forms to improve thermal and oxidative stability, which extends the shelf life of products, as seen in margarine production where partial hydrogenation adjusts the consistency of the product . Inter-esterification, especially when done enzymatically, allows modification of molecular composition without forming trans fats, improving physical properties such as melting point and consistency, thus enhancing functionality and commercial value .

The structural heterogeneity of fats and oils, as mixtures of various triacylglycerol molecules with different fatty acids, impacts industrial processing methods such as fractionation and inter-esterification significantly. In fractionation, this heterogeneity allows for the separation of components with different melting points, improving the functionality and value of the final products . For inter-esterification, the positional and molecular diversity allows for the redistribution of fatty acids, altering physical properties and improving the quality of products like margarine without forming trans fats . This intrinsic variability is essential for tailoring fat products to desired specifications in the food industry.

Temperature is crucial in the inter-esterification process as it facilitates the exchange of esters among triglyceride molecules. The process typically occurs around 80°C, which ensures efficient catalysis, often using sodium methoxide in chemical methods . Appropriate temperature control ensures that the molecular composition of the oil is altered effectively, changing physical properties such as melting point and consistency without impacting fatty acid composition, ultimately enhancing the oil's functionality for applications like improving the handling qualities of natural lard and margarine production .

The hydrogenation process used in margarine and shortening production can lead to the formation of trans fatty acids due to incomplete hydrogenation, where double bonds of unsaturated fatty acids shift to unnatural trans positions. Trans fats are associated with increased risk of coronary heart disease because they can contribute to higher levels of LDL cholesterol and lower levels of HDL cholesterol, thus negatively impacting heart health .

Palm oil is particularly suitable for fractionation because it has nearly equal parts of saturated and unsaturated fatty acids, allowing for the easy separation into olein and stearin fractions . This process enhances its marketability by improving functionality and commercial value, as it produces specialized products with specific melting ranges which are desirable for various applications, such as confectionery and non-dairy creamers . The ability to cater to diverse market needs makes palm oil a versatile and valuable commodity in the food industry.

The primary challenge in controlling the hydrogenation process to achieve the desired consistency in products like margarine is avoiding complete hydrogenation, which makes the product too hard, while also preventing the formation of trans fats from incomplete hydrogenation. Achieving balance requires precise control over the addition of hydrogen, temperature, pressure, and catalyst presence . To address these challenges, manufacturers often rely on partial hydrogenation, carefully stopping the process at the right moment to ensure the oil is at the desired consistency without producing excessive trans fats, though some trans fats may still form inadvertently .

Enzymatic inter-esterification offers several advantages over chemical inter-esterification. It minimizes processing loss as it avoids oil saponification, maintains oxidative stability since tocopherol loss is avoided, and produces lower levels of reaction by-products such as monoglycerides and diglycerides . Additionally, enzymatic methods eliminate the problem of flavor reversion and allow for more controlled specific reactions (regiospecific), though they are more complex to operate and control compared to the highly reproducible and easily managed chemical process .

Key steps in the hydrogenation of oils include adding hydrogen to unsaturated fatty acids at controlled temperatures and pressures in the presence of a metal catalyst like nickel. These conditions facilitate the conversion of liquid oils into semisolid or solid fats by reducing double bonds within the fatty acids. The impact on the final product includes an increase in melting point and oxidative stability, which extends the shelf life and changes the texture of the product, making it suitable for applications like margarine . Partial hydrogenation, however, may result in trans fat formation which has health implications .

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