The conjugation and epoxidation of fish oil

摘要

Wilkinson's catalyst [RhCl(PPh3)(3)] has been used to conjugate fish oils in high yields under very mild reaction conditions. A catalyst load of 0.35 mol% of RhCl(PPh3)(3), 0.43 mol% of (o-CH3C6H4)(3)P, and 0.87 mol% of SnCl2 (.) 2H(2)O in ethanol solvent at 60degreesC for 2 d produces 82% conjugated Norway fish oil ethyl ester in a 91 % yield. A Capelin triglyceride fish oil affords 90% conjugated fish oil in 93% yield. The Sharpless epoxidation procedure has also been employed to epoxidize fish oils. Using 0.34 mol% of CH3ReO3, 8.15 mol% of pyridine, and 1.03 equivalents of aq. 30% hydrogen peroxide in methylene chloride solvent at 25degreesC for 6 h, the Norway fish oil ethyl ester can be 100% epoxidized in an 86% yield. The Capelin fish oil gives 100% epoxiclized fish oil in a 72% yield. Decreasing the amounts of CH3ReO3 and pyridine used in the reaction results in partially epoxiclized fish oils.