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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of 6-Hydroxy Delta-Lactones and 5,6-Dihydroxy Eicosanoic/ Docosenoic Acids from Meadowfoam Fatty Acids Via a Lipase Mediated Self Epoxidation

item Frykman, Hans
item Isbell, Terry

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 24, 1997
Publication Date: N/A

Interpretive Summary: "Environmentally friendly" or "green" products are those that quickly degrade in the environment, have little or no long lasting affect in the soil or water, and are not harmful to humans and wildlife species exposed to their use. When consumers look for green products at the supermarket or at the auto parts store they may have concerns about how effective the products will be compared to established conventional products. However, research is showing that when green products meet traditional or more stringent specifications, they provide superior performance with lower consumption. They have the added advantage of being derived from renewable agricultural resources. USDA scientists are developing a whole range of "green" and highly effective lubricants, detergents, personal care and coating products from agricultural sources utilizing newly developed techniques. Meadowfoam is an oilseed plant currently grown in Oregon and produces an oil with unique structures for the manufacture of the above mentioned products. To achieve our goal of developing detergents and coatings we devised a procedure to "activate" the fatty acids from meadowfoam oil. These processes are called epoxidation and lactonization and are very efficient, yielding an activated building block for further chemical conversions. We can now synthesize highly effective detergents and coatings from this building block, an important advance in developing meadowfoam as an alternative crop for American farmers.

Technical Abstract: Meadowfoam fatty acids were reacted with hydrogen peroxide in a lipase catalyzed auto catalytic system, forming a mixture of 5,6-epoxyeicosanoic and 5,6,13,14-diepoxydocosanoic acids in 98% yield. The epoxy acids were cyclized to 6-hydroxy delta-eicosanoic/docosanoic lactones by sulfuric acid catalysis in high yield (99%). 5,6 Dihydroxy eicosanoic acid could be obtained from 6-hydroxy delta-lactones by a simple alkaline work up procedure. Meadowfoam fatty acids were converted (77% yield) in a one pot reaction to 6-hydroxy delta-lactones by in situ performic acid epoxidation and subsequent addition of sulfuric acid.

Last Modified: 4/22/2015
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