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United States Department of Agriculture

Agricultural Research Service

Title: The Rate of Ring Opening of Gamma and Delta-Lactones Derived from Meadowfoam Fatty Acids

item Isbell, Terry
item Plattner, Beth - INDIANA UNIVERSITY

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: September 13, 1996
Publication Date: N/A

Interpretive Summary: Vegetable oils are used to manufacture biodegradable detergents, personal care ingredients and lubricants. The cost to make these items, and often the difficult process to convert them, prevents the oils from being used. A new crop called meadowfoam has an oil with unique structure. This unique oil can be converted to a basic ingredient called delta-lactone. The delta-lactone races to form detergent, lubricant and cosmetic type molecules at 9000 times as fast as ordinary oils. Expect many new products to be on the market from delta-lactones and a smile on the faces of meadowfoam growers who will benefit from this new discovery.

Technical Abstract: Delta-lactones derived from meadowfoam (limnanthes) fatty acids were reacted with amine and alcohol nucleophiles in a second order reaction to provide the acyclic 5-hydroxy eicosanoic acid esters and amides. The rate of reaction for the ring opening of delta-lactones was compared to the rate of ring opening of gamma-lactones and the rate of derivatization of meadowfoam fatty acids. Delta-lactones showed a much larger rate for the formation of derivatives than the corresponding gamma-lactones or fatty acids. Delta-lactone had a rate constant >7700 times larger for the formation of butyl ester than meadowfoam fatty acids. The formation of amides from delta-lactones is even faster than the esterification reaction and requires no catalyst or solvent when conducted at the melting point of the lactone.

Last Modified: 4/22/2015
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