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Polymers and polymer building blocks from meadowfoam oil |
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| Authors: | S Warwel F Brüse C Demes M Kunz |
| Institution: | Institute for Lipid Research, Federal Centre for Cereal, Potato and Lipid Research, Piusallee 68, D-48147, Münster, Germany |
| Abstract: | Meadowfoam oil methyl ester was metathetically cleaved with ethylene catalyzed by Re2O7–B2O3/Al2O3–SiO2 + SnBu4 or bis(tricyclohexyl phosphine) benzylidene ruthenium dichloride yielding  -olefins, ,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. |
| Keywords: | Meadowfoam oil Olefin metathesis Chemoenzymatic epoxidation Oxidative cleavage Insertion polymerization Polycondensation |
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