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United States Department of Agriculture

Agricultural Research Service

Title: Method for the Development of Delta-Lactones Ad Hydroxy Acids from Unsaturated Fatty Acids and Their Glycerides
See also: US Patent Office Full Record

Patent Number: 6022982
Docket Number: 1799
Serial Number: 9211017
Date Patented: 02/08/2000

Technology Description:

The invention relates to a novel process for producing delta-lactones and 5-hydroxy fatty acids from unsaturated fatty acidssuch as oleic, palmitoleic, linoleic, linolenic, and erucic acids, and their glycerides. The delta-lactones may be produced byreacting one or more unsaturated fatty acids in the presence of an acid catalyst and at a temperature between about 20oC to70oC. Yields of the delta-lactones may be increased even further by reaction in the presence of dipolar, nonparticipating, 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 bepracticed using naturally occurring plant oils directly, without the need for any preliminary steps of saponification or steamsplitting. A variety of plant and a vegetable oils may be used including soybean, cottonseed, corn, olive, peanut, palm, sesame,sunflower, and canola oils. 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. Hydroxyfatty acids are useful as lubricants and greases, and in cosmetics, soaps, detergents, and fabric softeners.


Please refer to USPN 6,022,982, which issued on February 8, 2000. 


Terry A. Isbell
New Crops Research, NCAUR
1815 N. University Street
Peoria, Illinois 61604
(309) 681-6533
Steven C. Cermak
(Same address as first inventor)

Last Modified: 10/1/2015