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Omega‐formylalkanoates by ozonization of unsaturated fatty esters
Author(s) -
Anders D. E.,
Pryde E. H.,
Cowan J. C.
Publication year - 1965
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/bf02541138
Subject(s) - chemistry , organic chemistry , methanol , polyunsaturated fatty acid , aldehyde , solvent , ozonolysis , linoleic acid , fatty acid , catalysis
Abstract Ozonization of the methyl esters of 11‐eicosenoic, linoleic, erucic and linolenic acids gave a number of different homologous methyl ३‐formylalkanoates. Complete ozonization of the monounsaturated esters formed C 11 and C 13 compounds with 90% conversion; partial ozonization of the polyunsaturated esters gave C 12 and C 15 products with maximum conversions at ca. 75% consumption of fatty ester. Thus, methyl linoleate gave 52 and 23% conversions to the 9‐ and 12‐carbon products, and methyl linolenate gave 29, 27 and 19% conversions to the 9‐, 12‐ and 15‐carbon products. Yields of aldehyde or acetal esters in distilled products were 70舑90% in preparative‐scale experiments. Kinetic analysis showed that ozone attack was essentially random. Methanol was used as a participating solvent.