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Hydrogenation of cis ‐9, cis ‐12‐, cis ‐9, trans ‐12‐ and trans ‐9, trans ‐12‐ Octadecadienoates
Author(s) -
Scholfield C. R.
Publication year - 1972
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/bf02609231
Subject(s) - isomerization , cis–trans isomerism , catalysis , chemistry , double bond , platinum , conjugated system , nickel , medicinal chemistry , copper , stereochemistry , organic chemistry , polymer
The products formed by hydrogenation of methyl cis ‐9, trans ‐12‐ and trans ‐9, trans ‐12‐octadecadienoates with nickel and platinum catalysts have been compared with those from methyl esters of the naturally occurring all‐ cis linoleate. Hydrogen uptake is slower for the trans isomers. Much of the monoene consisted of esters with double bonds at the 9 and 12 positions with their original geometric configurations. Monoenoic esters with double bonds at the 10 and 11 positions were predominately trans and apparently formed by conjugation before hydrogenation. Nickel produced more isomerization than platinum but less than previously reported for copper. With both catalysts hydrogenation proceeded both directly and through conjugated intermediates, in contrast to copper in which all hydrogenation is believed to follow conjugation.