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Hydrogenation of linolenate. II. Hydrazine reduction
Author(s) -
Scholfield C. R.,
Jones E. P.,
Nowakowska Janina,
Selke E.,
Dutton H. J.
Publication year - 1961
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02633234
Subject(s) - diene , linolenate , chemistry , double bond , isomerization , organic chemistry , hydrazine (antidepressant) , elution , maleic anhydride , distillation , chromatography , catalysis , fatty acid , natural rubber , copolymer , polymer
Abstract Observations by Aylward and Rao that hydrazine is a reducing agent for a number of unsaturated fatty acids were extended. The hydrazine reaction on linolenic acid was followed by periodic sampling until methyl esters prepared from the reduced acids had an iodine value of 162. These esters were shown by countercurrent distribution to consist of 26% triene, 43% diene, 26% monoene, and 5% stearate and by infrared analysis to contain no trans bonds. Oxidation of the separated monoene and diene fractions by permanganate‐periodate mixtures and gas chromatography of the dibasic acids showed that the double bonds were in the original 9, 12, and 15 positions and that the double bonds farthest from the carboxyl were reduced at a slightly faster rate. Gas chromatography of the monoene fraction indicated three components that were identified in the order of elution from the column as 9, 12, and 15 monoenes; in the diene fraction three components were identified in the order of elution as 9,12; 9,15; and 12,15 dienes. After alkali isomerization of this diene fraction, the conjugated material was reacted with maleic anhydride; the unreacted 9,15 diene isomer was separated by distillation.