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Ethylene adduct of conjugated octadecadienoic acids. II. OZONIZATION products

Permanent URL:
http://handle.nal.usda.gov/10113/30824
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Abstract:
Methyl 8-(4-n-hexylcyclohex-2-enyl) octanoate obtained by esterifying the adduct of ethylene and trans,trans-9,11-octadecadienoic acid was ozonized in methanol as a participating solvent. The resultant cyclic methoxyhemiperacetal was reduced with powdered zinc to the dialdehyde, methyl 9,12-diformylstearate, which was isolated as the tetramethyldiacetal. This dialdehyde readily air-oxidizes to give methyl 9,12-dicarboxystearate. Heating the cyclic methoxyhemiperacetal slowly from 25 to 100 C in vacuo results in an unusual decomposition reaction which gives hydrogen and methyl 9 (12)-carbomethoxy-12(9)-carboxystearate as the primary products and methyl 9 (12)-carbomethoxystearate as the major by-product. Treatment of the cyclic hemiperacetal with hydrogen peroxide in formic acid gave unexpectedly dihydroxystearic acid as one of the products.
Author(s):
Dufek, E.J. , Cowan, J.C. , Friedrich, J.P.
Note:
20090709 20090801 00000000
Source:
The journal of the American Oil Chemists' Society Feb 1970, 47 (2)
Language:
English
Publisher:
American Oil Chemists' Society
Year:
1970
Collection:
Journal Articles, USDA Authors, Peer-Reviewed
Rights:
Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted.