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United States Department of Agriculture

Agricultural Research Service

Title: Production of Fatty Polyols by Hydrolysis after Enzymatic Epoxidation

Authors
item Piazza, George
item Foglia, Thomas

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: July 25, 2004
Publication Date: August 2, 2004
Citation: Piazza, G.J., Foglia, T.A. 2004. Production of fatty polyols by hydrolysis after enzymatic epoxidation {abstract}. American Oil Chemists' Society Industrial Applications of Renewable Resources. Poster No. 4.

Technical Abstract: Peroxygenase is an enzyme that can oxidize double bonds to form epoxides. Oat seeds are a particularly good source of peroxygenase, but the work needed to isolate and immobilize this enzyme multiplies its cost. Therefore, the feasibility of using ground oat seeds as an inexpensive source of peroxygenase was explored. Although oat seeds contain a very active lipase, it was found that fatty amides were not affected by the lipase and were good substrates for peroxygenase. Free fatty acids were also good substrates. Reaction conditions for producing high yields of epoxides from free fatty acids or fatty amides were determined in either all aqueous media or in media that were composed mostly of hexane. The enzymatic epoxidation showed regioselectivity that greatly reduced epoxidation of adjacent double bonds; thus, for example, when linolenic acid or its amide derivative was epoxidized, the primary product was the diepoxide with the central double bond remaining unreacted. Linoleic acid and its derivatives gave a large amount of the monoepoxide, and the diepoxide was formed at a relatively slow rate. When enzymatically epoxidized vegetable oils from several sources were subjected to acidic hydrolysis, the products contained mostly di- and tetrapolyols. In contrast, polyols obtained from commercially available epoxidized esters gave greater amounts of dihydrofuran derivatives because they contained high amounts of adjacent epoxides, and these rearrange to dihydrofurans upon hydrolysis. Thus the enzymatically derived polyols have different chemical properties than those obtained from commercial epoxides. These difference could be exploited to produce new materials with unique chemical properties.

Last Modified: 10/24/2014
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