Ultrasound‐assisted oxidative cleavage of acetylenic and ethylenic bonds in unsaturated fatty esters with potassium permanganate | Zendy

Lie Ken Jie Marcel S. F. | Zendy; Kalluri Prabhavathi | Zendy

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Ultrasound‐assisted oxidative cleavage of acetylenic and ethylenic bonds in unsaturated fatty esters with potassium permanganate

Author(s) -

Lie Ken Jie Marcel S. F.,

Kalluri Prabhavathi

Publication year - 1996

Publication title -

lipids

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.601

H-Index - 120

eISSN - 1558-9307

pISSN - 0024-4201

DOI - 10.1007/bf02587916

Subject(s) - chemistry , potassium permanganate , double bond , fatty acid , oxidative cleavage , unsaturated fatty acid , acetic acid , carboxylic acid , substrate (aquarium) , organic chemistry , yield (engineering) , bond cleavage , catalysis , oceanography , materials science , metallurgy , geology

The effect of ultrasound on the oxidation of unsaturated fatty esters was investigated. Unsaturated fatty esters containing acetylenic or olefinic bonds or both were oxidatively cleaved with KMnO 4 in aqueous acetic acid (AcOH/H 2 O, 1:1, vol/vol for olefinic fatty esters and AcOH/H 2 O, 9:1, vol/vol for acetylenic fatty esters) to yield the corresponding carboxylic acid moieties in quantitative yields, when the reactions were conducted under ultrasound (20 kHz, 53 W/cm 2 , 8–15 min). The methyl ester derivatives of the carboxylic acid moieties formed were identified by gas‐liquid chromatographic analysis. The procedure constitutes a facile method for the determination of the position of the unsaturated center (olefinic or acetylenic) in an unsaturated fatty ester substrate, especially where the unsaturated system consists of an acetylenic bond.

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