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Isomerization studies: III. decarbonylation of oleoyl chloride preparation of C 19 dicarboxylic acids
Author(s) -
Barr P. A.,
Foglia T. A.,
Schmeltz I.
Publication year - 1975
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/bf02545276
Subject(s) - dicarboxylic acid , diene , chemistry , isomerization , decarbonylation , carboxylation , organic chemistry , catalysis , chloride , hydroformylation , medicinal chemistry , rhodium , natural rubber
Mixtures of siomeric C 17 diene hydrocarbons were obtained when oleoyl chloride was decarbonylated in the presence of a transition metal catalyst. The choice of catalyst determined the composition of diene mixture produced. Diene mixtures were characterized as a mixture of conjugated and 1,4‐ dienes, or as a mixture of isolated double bond dienes. Carboxylation of the conjugated C 17 diene by hydroformylationoxidation procedure gave a C 18 monocarboxylic acid as the major product, whereas with nonconjugated C 17 diene, the major product was a C 19 dicarboxylic acid. Application of the Koch carboxylation procedure to C 17 diene mixtures gave a C 19 dicarboxylic acid mixture as the major product. This latter acid mixture was structurally different from diacids obtained from the hydroformylation‐oxidation procedure.