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Selective synthesis of propenyl‐branched diunsaturated fatty esters via catalytic codimerization of ethyl linoleate and propylene
Author(s) -
Erb Benjamin,
Dierker Markus,
Ohlmann Dominik M.,
Gooßen Lukas J.
Publication year - 2016
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201500197
Subject(s) - chemistry , catalysis , organic chemistry , fatty acid , interesterified fat , ethyl ester , lipase , enzyme
A bimetallic catalyst system consisting of RhCl 3 and Pd(MeCN) 2 Cl 2 efficiently promotes the conversion of ethyl linoleate selectively to mono‐propenylated diunsaturated products. The reaction proceeds in high yields under mild conditions. The key advantage of the new process is that it is based on the readily available linoleate rather than a preformed conjuenic acid ester. Practical applications: The new protocol opens up a high yielding and environmentally friendly method for the introduction of side chains with a defined length into fatty acid derivatives. The products are of profound potential interest for industrial applications, e.g., in lubricants, cosmetics, plastics, and coatings, as branched fatty acids are known to have a lower solidifying point and viscosity and an increased solubility than their linear counterparts. Rh/Pd‐catalyzed selective conversion of ethyl linoleate to mono‐propenylated diunsaturated products under mild conditions.