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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of Secondary Ethers Derived from Meadowfoam Oil

Authors
item Isbell, Terry
item Mund, Melissa

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 25, 1998
Publication Date: N/A

Interpretive Summary: What makes meadowfoam a marketable crop? It's different from the other crops because it has a unique oil. We need to take advantage of that uniqueness in the things we make from meadowfoam oil. Oil products whose molecules branch, like a tree, melt and pour at lower temperatures and last longer in lubricants than unbranched ones, but the branched ones couldn't be made easily from traditional vegetable oils. We took advantage of the uniqueness of meadowfoam oil structure to add alcohols to it and make branches called ethers. Meadowfoam ethers are a new ingredient, not economically possible before, which will be useful in a wide variety of industrial products.

Technical Abstract: Secondary ethers can be obtained from meadowfoam derived delta lactones or 5-hydroxy fatty acids using Lewis or Bronstead acid catalysts in good yield (70-90%). The conversion of delta lactone or 5-hydroxy fatty acid to 5-ethers is performed under atmospheric pressures from 67-125C with 0.5-6.4 mole equivalents of acid catalyst in the presence of 2-40 equivalents of alcohol and a reaction time of 1-140 hours. Acid catalysts include mineral acids such as perchloric and sulfuric, Lewis acids such boron triflouride and heterogeneous catalysts such as clays and ion-exchange resins. Primary alcohols such as methanol, butanol, decanol and oleyl alcohol or branched chain alcohols like 2-ethylhexanol can be used to make secondary ether fatty esters. The 5-ether fatty esters and the process for their formation has not been previously known and appears to be limited to structures where stabilized cations can be formed. The novel ethers were fully characterized using NMR and GC-MS.

Last Modified: 9/2/2014
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