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Reactions of carbon monoxide with unsaturated fatty acids and derivatives: A review
Author(s) -
Pryde E. H.,
Frankel E. N.,
Cowan J. C.
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/bf02582478
Subject(s) - carboxylation , isomerization , carbon monoxide , chemistry , catalysis , organic chemistry , carbonylation , bifunctional , triphenylphosphine , polymer chemistry
The important reactions of carbon monoxide with unsaturated fatty derivatives that are reviewed in this paper include hydroformylation (the oxo reaction), Koch carboxylation and Reppe carbonylation. With oleic acid as a substrate, the products are C 19 bifunctional compounds e.g., formyl‐ or carboxy‐stearic acid. Double bond isomerization before carbon monoxide addition is characteristic of these catalytic reactions; additionally, rearrangement to introduce methyl branching occurs in the Koch carboxylation. Isomerization does not occur when a rhodium‐triphenylphosphine catalyst replaces cobalt in the oxo reaction. Properties of the C 19 dicarboxylic acids differ and depend upon method of preparation: Many areas of application have been reported for C 19 compounds‐lubricants, plasticizers, polyurethanes, epoxy resins, leather and other coatings, unsaturated polyester resins and transparent polyamide plastics.