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Periodate‐permanganate oxidations for determining location and amount of unsaturation in monounsaturated fatty acids
Author(s) -
Jones E. P.,
Stolp J. A.
Publication year - 1958
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/bf02672657
Subject(s) - azelaic acid , dibasic acid , degree of unsaturation , oleic acid , chemistry , permanganate , organic chemistry , periodate , yield (engineering) , chromatography , biochemistry , materials science , metallurgy
Conclusions Periodate‐permanganate oxidation of three samples of oleic acid considered to be of high purity has given reproducible but less than theoretical amounts of total dibasic acids. Recovery approximated 92% with about 90.3% of the expected azelaic acid. Recovery of other dibasic acids indicated that about 1.5% of the total unsaturation of these samples of oleic acid was present in positions 8 or 10 in the fatty acid molecule. Oxidation of elaidic acid produced from one of the oleic acids has given total dibasic acid yield of about 96%, with a smaller amount of its total unsaturation in the same position as in the parent oleic acid. Oxidation of high purity 9,10‐dihydroxystearic acid has given essentially quantitative yield of total dibasic acids. The method described should be useful in determining the composition of similar unsaturated positional isomers. Controls showing the effect of the method on azelaic acid and on a mixture of azelaic acid with pelargonic have shown essentially quantitative recovery of azelaic acid. Failure to establish quantitative recovery on oxidation of oleic acid must be caused by some unknown factor during oxidation per se . The experimental technique described was satisfactory for quantitative studies of the type undertaken. Oxidation of moderate‐purity, mono‐unsaturated fatty acids, such as erucic, 10‐undecenoic, and vaccenic acid, has given mixed dibasic acids corresponding to the respective positions of unsaturation. The data indicate that the method described shows the position of minor unsaturation within about 1%.