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United States Department of Agriculture

Agricultural Research Service

Title: New Industrial Products from Unique Derivatives of New Crop Oils

Authors
item Isbell, Terry
item Frykman, Hans
item Mund, Melissa

Submitted to: International Society of Fats
Publication Type: Abstract Only
Publication Acceptance Date: September 12, 1997
Publication Date: N/A

Technical Abstract: A key aspect of the commercialization of a new crop is the ability to take advantage of the unique chemical components in the plant for industrial products. This presentation describes several new classes of chemical derivatives developed in our laboratories which exploit an oil's unique chemical structure. These classes are broken into the following categories sestolides, delta-lactones, 5-substituted fatty acids and geminal substituted fatty acids. Estolides are oligomeric esters from fatty acids acids that have low melting and pour points. Industrial products from estolides are being developed in the cosmetics and lubricants area in coop- eration with industrial partners. Delta-lactones have been produced in high yield from triglycerides and fatty acids by a mineral acid catalyzed process that utilizes transition state stabilization theory to capture the kinetic product. Delta-lactones are 6-membered cyclic esters with very hig greactivities toward nucleophiles such as alcohols and amines. The reactivity of delta-lactones has allowed the production of a wide range of 5-hydroxy amides and esters, including some that were not previously possible from fatty acids or their derivatives. A number of new products such as 5-alkoxy esters have been made, and these ethers have good low temperature properties and viscosities not typically associated with vegetable oils. Lastly, the chemistry of hypochlorite has been exploited to produce geminal branched fatty acids using alcohols and common household bleach. Initial reaction products from this reaction are 5-chloro-6-alkoxy fatty acids, 6-chloro-delta-lactones or 5,6-dihydroxy fatty acids depending on the reaction conditions. These new oxygenated fatty acids are being evaluated for possible applications based on their physical properties.

Last Modified: 7/24/2014
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