Epoxidation reactions of unsaturated fatty esters with potassium peroxomonosulfate

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.K2SO4) in the presence of trifluoroacetone or methyl pyr...

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Bibliographic Details
Published in:Lipids 1998-06, Vol.33 (6), p.633-637
Main Authors: Lie Ken Jie, Marcel S. F., Pasha, Mohammed Khysar
Format: Article
Language:English
Subjects:
Epoxy Compounds - chemistry
Esterification
Esters
Fatty Acids, Unsaturated - chemistry
Indicators and Reagents
Oxidants - chemistry
Oxidation-Reduction
Solvent extraction
Sulfuric Acids - chemistry
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Summary: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.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.
ISSN:0024-4201
1558-9307
DOI:10.1007/s11745-998-0250-6