Epoxidation reactions of unsaturated fatty esters with potassium peroxomonosulfate.

Abstract:

:Epoxidation of the double bond in methyl oleate, octadec-11E-en-9-ynoate, ricinoleate (12-hydroxy-octadec-9Z-enoate), iso-ricinoleate (9-hydroxy-octadec-12Z-enoate), and 12-oxo-octadec-9Z-enoate with potassium peroxomonosulfate (oxone, 2 KHSO5.KHSO4.K2SO4) in the presence of trifluoroacetone or methyl pyruvate gave the corresponding monoepoxy derivatives. Reaction of Oxone with methyl linoleate and octadeca-9Z,11E-dienoate furnished the corresponding diepoxystearate derivative. Methyl 9,12-dioxo-octadec-10Z-enoate was obtained when a C18 furanoid fatty ester (methyl 9,12-epoxy-9,11-octadecadienoate) was treated with Oxone. The yield of these reactions was very high (85-99%), and the epoxy derivatives were readily isolated by solvent extraction. The products were identified by spectroscopic methods.

journal_name

Lipids

journal_title

Lipids

authors

Lie Ken Jie MS,Pasha MK

doi

10.1007/s11745-998-0250-6

subject

Has Abstract

pub_date

1998-06-01 00:00:00

pages

633-7

issue

6

eissn

0024-4201

issn

1558-9307

journal_volume

33

pub_type

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