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.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.
Lie Ken Jie
M S
MS
Department of Chemistry, The University of Hong Kong, Hong Kong. hrsclkj@hkucc.hku.hk
Pasha
M K
MK
D004852:Epoxy Compounds / Q000737:chemistry; D004951:Esterification; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D007202:Indicators and Reagents; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D013464:Sulfuric Acids / Q000737:chemistry*
D004852:Epoxy Compounds; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; D016877:Oxidants; D013464:Sulfuric Acids; C048813:potassium peroxymonosulfuric acid