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Hydrogenation of monounsaturated and ethylene‐ and methylene‐interrupted diunsaturated fatty acid esters on nonmetallic palladium‐on‐resin II
Author(s) -
Van der Plank P.,
Van Oosten H. J.
Publication year - 1979
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/bf02671760
Subject(s) - isomerization , chemistry , ethylene , palladium , catalysis , methylene , acetone , double bond , solvent , medicinal chemistry , diene , hydrogen , organic chemistry , natural rubber
Methy cis ‐9‐octadecenoate (methyl oleate; c 9), methyl cis ‐9, cis ‐13‐octadecadienoate ( c 9, c 13) and a 50∶50 mixture of this diene with methyl cis ‐9, cis ‐12‐octadecadienoate (methyl linoleate; c 9, c 12) have been hydrogenated on a nonmetallic palladium‐onresin catalyst in acetone as a solvent at 40 C and atmospheric hydrogen pressure. The monoene is hydrogenated very slowly, but c 9, c 12 is reduced easily and quickly. The ethylene‐interrupted diene reacts more slowly than c 9, c 12, but considerably faster than c 9, because active methylene‐interrupted dienes are intermediates by double‐bond migration. This isomerization process also results in the formation of inactive polymethylene‐interrupted dienes, which accumulate during hydrogenation. Also c 9 isomerizes considerably during reduction. In the 50∶50 mixture, c 9, c 12 is hydrogenated about eight times faster than c 9, c 13.