Hydrogenation of monounsaturated and ethylene‐ and methylene‐interrupted diunsaturated fatty acid esters on nonmetallic palladium‐on‐resin II

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Abstract
Methycis‐9‐octadecenoate (methyl oleate;c9), methylcis‐9,cis‐13‐octadecadienoate (c9,c13) and a 50∶50 mixture of this diene with methylcis‐9,cis‐12‐octadecadienoate (methyl linoleate;c9,c12) 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, butc9,c12 is reduced easily and quickly. The ethylene‐interrupted diene reacts more slowly thanc9,c12, but considerably faster thanc9, 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. Alsoc9 isomerizes considerably during reduction. In the 50∶50 mixture,c9,c12 is hydrogenated about eight times faster thanc9,c13.
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