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Oxidation of alkenes with use of phase transfer catalysis
Author(s) -
Foglia T. A.,
Barr P. A.,
Malloy A. J.
Publication year - 1977
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/bf02909055
Subject(s) - chemistry , potassium permanganate , catalysis , phase transfer catalyst , aqueous solution , inorganic chemistry , permanganate , halide , sodium hypochlorite , polymer chemistry , organic chemistry
and summary The use of phase transfer catalysis (PTC) as an aid in the oxidation of long chain olefins with aqueous potassium permanganate (KMnO 4 ) in neutral and alkaline media and with aqueous ruthenium tetroxide (RuO 4 ) is reported. The phase transfer catalysts (PTCT) were either quaternary ammonium halides or crown ethers. The long chain olefins studied were 1‐pentadecene, 9‐octadecene, and methyl oleate. PTC not only increases the rate of these reactions but also gives good yields of reaction products. For example, cis ‐9‐octadecene in methylene chloride reacted with aqueous KMnO 4 to give either dihydroxyoctadecane (80%) or pelargonic, acid (80%) depending upon pH, when tetrabutylammonium bromide was used as the PTCT. When RuO 4 in conjunction with a PTCT was used as the oxidant, a quantitative yield of myristic acid was obtained from 1‐pentadecene. The RuO 4 oxidant was conveniently regenerated in situ from RuO 2 and sodium hypochlorite. This regeneration is facilitated with a PTCT.