Metathesis Reactions Applied to Plant Oils and Polymers Derived from the Ensuing Products

CaO Catalyzed Transesterification of Ethyl 10-Undecenoate as a Model Reaction for Efficient Conversion of Plant Oils and Their Application to Depolymerization of Aliphatic Polyesters

“…On the basis of these results, we thus have an interest in applying the catalyst for conversion of FAEs to fine chemicals including the monomer synthesis of biobased aliphatic polyesters. ,− ,− This is because the conventional monomer synthesis with ethyl (or methyl) 10-undecenoate (derived from castor oil) by transesterification generally requires excess 1,1′-carbonyl diimidazole, p -toluene sulfonic acid, or NaOMe or NEt 3 and 4,4-dimethylaminopyridine, whereas reports for the catalytic transesterification in the presence of Sc­(CF 3 SO 3 ) 3 or Cu/V 2 O 5 were also known. In particular, α,ω-dienes derived from a castor oil derivative, ω-undecenoate containing a terminal olefinic double bond and carboxylate (exemplified as ethyl 10-undecenoate in this study), prepared by transesterification are useful feedstock for the synthesis of biobased linear polyesters via acyclic diene metathesis (ADMET) polymerization and subsequent olefin hydrogenation. ,, This is because ADMET polymerization provides a wide variety of polyesters that are not available by the other methods (like polycondensation), as exemplified in many reports for the synthesis of α,ω-dienes derived from fatty acids and its derivatives. ,,− Therefore, development of a clean, efficient catalytic method has been desired for the synthesis of fine chemicals and monomer synthesis. ,− …”