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United States Department of Agriculture

Agricultural Research Service

Title: Fatty Alcohols Through Hydroxylation of Symmetrical Alkenes with Selenium Dioxide / TERT.-BUTYLHYDROPEROXIDE

item Knothe, Gerhard
item Bagby, Marvin
item Weisleder David,

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: May 25, 1995
Publication Date: N/A

Interpretive Summary: In search of fatty materials suitable as additives to develop or improve several commercial products, novel fatty alcohols (compounds with resemblance to fatty acids derived from numerous agricultural products) were made. The unusual feature of these compounds is that the structure making them alcohols is at the center rather than the end of the molecule. These compounds possess interesting physical and chemical characteristics. They may be useful for preparing biodiesel, lubricants, cosmetics and greases.

Technical Abstract: Several symmetrical alkenes were reacted with the selenium dioxide / tert.-butylhydroperoxide system to give three hydroxylated products each. These products were those of allylic mono- and dihydroxylation (meso and threo dihydroxy compounds) of the double bond. Some dihydroxy products were hydrogenated to give saturated 1,4-diols. The compounds were characterized by NMR. The products have potential for application in commercial products such as biodiesel, lubricants, greases and cosmetics.

Last Modified: 4/20/2015
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