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Type and Extent of Isomerization of Straight‐Chain Mono‐olefins during the Koch Carboxylic Acid Synthesis
Author(s) -
Möller K. E.
Publication year - 1963
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196307191
Subject(s) - isomerization , boron trifluoride , chemistry , catalysis , sulfuric acid , organic chemistry , medicinal chemistry , carboxylic acid , molecule , stereochemistry
When straight‐chain mono‐olefins, from pentene to decene, are subjected to the Koch carboxylic acid synthesis by the addition of CO and H 2 O or CH 3 OH in the presence of strongly acidic catalysts, not only the expected secondary acids, but also mixtures of a specific type of tertiary acids or their methyl esters are formed. When the catalysts contain boron trifluoride, the secondary acids are formed in ratios of isomers which are, within the scope of this investigation, independent of the experimental conditions and which agree well with the values calculated from the isomer equilibria of the corresponding n‐olefins. Using concentrated sulfuric acid as catalyst, a larger proportion of tertiary acids is obtained than with BF 3 ‐catalysis, and amongst the secondary acids, those isomers predominate in which the COOH group is situated near the centre of the molecule.