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Stanley B. Elliott
Bedford Ohio
Keywords
saponiÞcation
Van Nostrand’s Encyclopedia of Chemistry, Copyright © 2005 John Wiley & Sons, Inc. 1
The diglyceride formed is subsequently split to the monoglyceride,
which Þnally is converted to glycerol, if sufÞcient alkali is present.
Thus, the reaction is a bimolecular one rather than quadrimolecular,
as is commonly indicated. In actual practice, the fats used are
complex glycerides of a number of saturated and unsaturated acids,
rather than the stearin shown here.
Technologically, the saponiÞcation operation varies in degree of
difÞculty depending on the ester. The reaction rate differs for
different esters, for one thing, bu another determining factor is the
contact area possible between the alkali and the ester. In the case
mentioned above, the fat at the start is insoluble and immiscible in
water, so that reaction in a nonagitated vessel would be very slow,
occurring only at the limited interface.
Though saponiÞcation is the dominant reaction when the techniques
described above are used, in many instances side reactions may
occur which may profoundly modify the products. Oxidation, of
course, is one of the more obvious things to guard against, since
many times the esters being treated are unsaturated. Both isomer-
ization and polymerization, however, may occur under the alkaline
conditions obtaining, the unconjugated polyethenoid acids becom-
ing conjugated during treatment. This especially appears to be true
in the case of highly unsaturated compounds. However, by properly
controlling reactants and conditions, saponiÞcation remains a very
ßexible and useful industrial and laboratory operation possible of
wide application and at low cost.
See also Soaps.