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United States Department of Agriculture

Agricultural Research Service


item Isbell, Terry
item Mund, Melissa

Submitted to: Industrial Crops and Products International Conference Proceedings
Publication Type: Abstract Only
Publication Acceptance Date: 10/21/1999
Publication Date: N/A
Citation: N/A

Interpretive Summary:

Technical Abstract: A range of studies was performed to utilize the unique chemistry of the delta5 unsaturation. Meadowfoam fatty acids and oil was cyclized in high yield (75-90%) to delta-lactones. Delta-lactones are kinetic products that are formed through the capture of a delta5 carbocation in an acid catalyzed cyclization. Strong mineral acids such as perchloric and sulfuric promote the reaction with optimum reaction temperatures near 40 C. Polar non-participating solvents such as methylene chloride aid in the formation of delta-lactone over the preferred thermodynamic product, gamma-lactone. Delta-lactones are useful as reactive intermediates which lead to derivatives of 5-hydroxy fatty acids. Delta-lactones were converted to a variety of amides in near quantitative yield with amines at 50 C in the absence of solvent. In a similar fashion, alcohols react with delta-lactone to give 5-hydroxy esters. Both amination and esterification reactions proceed with observed relative rates of 7000 to 9000 times faster than meadowfoam fatty acids. This reactivity was also utilized to synthesize secondary ethers from delta-lactones in high yield (70-94%) with a variety of primary alcohols in the presence of mineral or Lewis acids. Estolides, esters formed from the addition of one fatty acid across the backbone of a second fatty acid, were also synthesized form meadowfoam fatty acids with catalytic amounts of perchloric acid.

Last Modified: 05/27/2017
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