Polymers and polymer building blocks from meadowfoam oil

Abstract

Meadowfoam oil methyl ester was metathetically cleaved with ethylene catalyzed by Re2O7-B2O3/Al 2O3-SiO2 + SnBu4 or bis(tricyclohexyl phosphine) benzylidene ruthenium dichloride yielding α-olefins, α,ω-dienes and 5-hexenoic acid methyl ester as the main product. The corresponding ω-epoxy fatty acid ester was achieved by chemoenzymatic epoxidation with H2O2 in the presents of Novozym® 435. Glutaric acid mono methyl ester was synthesized by ruthenium-catalyzed oxidative cleavage with peracetic acid. Hydrocarboxylation with carbon monoxide/methanol yielded pimelic acid dimethyl ester. Metathetical dimerization of 5-hexenoic acid methyl ester yielded 5-decen-dioic acid dimethyl ester, which was subsequently polycondensed with ethylene glycole and 1,4-butanediol to high molecular weight polyesters. The ω-unsaturated ester was directly copolymerized with ethylene by an insertion-type palladium-catalyzed reaction to a high molecular weight functional polyolefin. The 5-epoxy hexanoic acid ester was polymerized to a comb like polyether. © 2003 Elsevier B.V. All rights reserved.