Method for the development of delta-lactones and hydroxy acids from unsaturated fatty acids and their glycerides

An improved process for the production of high yields of delta-lactones and 5-hydroxy fatty acids from unsaturated fatty acids such as oleic acid is disclosed. The delta-lactones may be produced by reacting one or more DELTA9 to DELTA15 unsaturated fatty acids in the presence of an acid catalyst and...

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Bibliographic Details
Published inUnited States Department of Agriculture patents no. 6
Main Authors Isbell, T.A, Cermak, S.C
Format Publication
LanguageEnglish
Published 2000
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Summary:An improved process for the production of high yields of delta-lactones and 5-hydroxy fatty acids from unsaturated fatty acids such as oleic acid is disclosed. The delta-lactones may be produced by reacting one or more DELTA9 to DELTA15 unsaturated fatty acids in the presence of an acid catalyst and at a temperature between about 20 to 70 degrees C. Moreover, yields of the delta-lactones may be increased even further by reaction in the presence of dipolar, non-participating, non-aqueous solvents. The unsaturated fatty acids may be free or esterified with glycerol or other aliphatic alcohols, and the delta-lactones may be produced by reacting mono-, di- or triglycerides of the unsaturated fatty acids with the same catalysts. Because the delta-lactones may be produced from the triglycerides of unsaturated fatty acids, the instant process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification or steam splitting. Optionally, the delta-lactones so formed may be further reacted to produce 5-hydroxy fatty acids. These 5-hydroxy fatty acids may be produced by reaction of the delta-lactones with an alkali in an aqueous solution.
Bibliography:http://hdl.handle.net/10113/6539