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Oxidation of unsaturated and hydroxy fatty acids by ruthenium tetroxide and ruthenium oxyanions
Author(s) -
Nakano Y.,
Foglia T. A.
Publication year - 1982
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/bf02680267
Subject(s) - ruthenium , chemistry , azelaic acid , oleic acid , double bond , medicinal chemistry , organic chemistry , polymer chemistry , catalysis , photochemistry , biochemistry
The reactions of ruthenium VIII tetroxide (RuO 4 ) and the ruthenium VII and VI oxyanions, perruthenate (RuO 4 − ) and ruthenate (RuO 4 = ) with hydroxy substituted and unsaturated fatty acids have been studied. At a 1:1 molar ratio, ruthenium tetroxide (RuO 4 ) and both oxyanions (RuO 4 − and RuO 4 = ) oxidized 12‐hydroxystearic acid to 12‐ketostearic acid. With 9, 10‐dihydroxystearic acid, the type of oxidation products obtained depended on the amount of ruthenium oxidant used. At high ratios of oxidant to substrate, cleavage to pelargonic and azelaic acids occurred whereas at lower ratios, partial oxidation to diketo and acyloin derivatives predominated. The oxidation of oleic acid with excess ruthenium tetroxide (RuO 4 ) or perruthenate anion (RuO 4 − ) gave the cleavage products pelargonic and azelaic acid through the intermediate formation of dihydroxy and diketo intermediates. Ruthenate anion (RuO 4 = ) did not react with the double bond of oleic acid.