CHEMICAL REACTIONS OF TRIACYLGLYCEROLS

Hydrogenation
Hydrogenation is a chemical reaction we first encountered. It involves hydrogen addition
across carbon-carbon multiple bonds, which increases the degree of saturation as some double
bonds are converted to single bonds. With this change, there is a corresponding increase in the
melting point of the substance.

Hydrogenation involving just one carbon-carbon bond within a fatty acid residue of a
triacylglycerol can be diagrammed as follows:

The structural equation for the complete hydrogenation of a triacylglycerol in which all three
fatty acid residues are oleic acid (18:1) is shown in figure 19.11.

Many food products are produced via partial hydrogenation. In partial hydrogenation some,
but not all, of the double bonds present are converted into single bonds. In this manner, liquids
(usually plants soils) are converted into semi-solid materials.

Peanut butter is produced from peanut oil through partial hydrogenation. Solid cooking
shortenings and stick margarine are produced from liquid plants soils through partial
hydrogenation. Soft-spread margarines are also partial-hydrogenation products. Here, the extent
of hydrogenation is carefully controlled to make margarine soft at refrigerator temperatures
(4°C). Concern has arisen about food products obtained from hydrogenation process itself
converts some cis double bonds within fatty acid residues into trans double bonds producing
trans unsaturated fatty acids.
Oxidation
The carbon-carbon bonds present in the fatty acid residues of a triacylglycerol are subject to
oxidation with molecular oxygen (from air) as the oxidizing agent. Such oxidation breaks the
carbon-carbon bonds, producing both aldehyde and carboxylic acid products.

The short-chain aldehydes and carboxylic acids so produced often have objectionable odors,
and fats and oils containing them are said to have become rancid. To avoid this unwanted
oxidation process, commercially prepared foods containing fats and oils nearly always contain
antioxidants—substances that are more easily oxidized than the food. Two naturally occurring
antioxidants are vitamin C and vitamin E, two synthetic oxidation inhibitors are BHA and BHT.
In the presence of antioxidants, rather than food, are oxidized.

BHA (butylated hydroxyanisole) and BHT (butylated hydroxytoluene)