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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of 5-Alkoxy Eicosanoates, Secondary Ethers Derived from Meadowfoam Oil

Authors
item Isbell, Terry
item Mund, Melissa

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 14, 1997
Publication Date: N/A

Technical Abstract: Meadowfoam (Limnanthes) is a promising new winter annual seed crop grown in the Pacific Northwestern U.S. that is establishing a role as an alternate crop. One aspect in the development of meadowfoam into a commercial crop is the utilization of its unique chemical structure for the manufacture of industrially useful compounds. In an effort to address this sissue, we developed a process for making branched oxygenated fatty esters. These branched derivatives have good low temperature properties and viscosities not typically associated with vegetable oils. Ethers can be obtained from 5-hydroxy fatty acids or delta lactones using Lewis or Bronsted acid catalysts in yields of 70-90%. The conversion of delta lactone or 5-hydroxy fatty acid to 5-ethers is performed under atmospheric pressures from 80-130 C with 0.5-2 mole equivalents of acid catalyst in the presence of 2-40 equivalents of alcohol and a reaction time of 2-24 hours. Acid catalysts include mineral acids such as perchloric and sulfuric, Lewis acids such as boron triflouride and zinc chloride and heterogeneous catalysts such as clays and ion-exchange resins. Alcohols can be normal or branched chain, primary or secondary. The 5-ether fatty acids and the process for their formation has not been previously known and appears to be limited to structures where stabilized cations can be formed.

Last Modified: 9/1/2014
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