The hydroesterificative copolymerization of bioderived α,ω-enols such as 10-undecenol (derived from castor oil) and CO has been demonstrated to give polyester. Novel monomers for hydroesterificative polymerization have been made through the combination of 10-undecenol and diol building blocks: isosorbide, p-xylene glycol, and ethylene glycol. A screen of various pressures, acids, and phosphine ligands has enabled polymerizations at lower pressures and with a commercially available catalyst system. Moderate molar masses (Mn = 6-10 kg/mol) were achieved using a simple catalyst system of Pd(OAc)2, PPh3 and TsOH.H2O. The resulting polymers were found to give a range of glass transition temperatures (-19 to 15 oC), dependent on the monomer functional groups. Additionally, this polymerization technique has been shown to work with bioderived monomers made from 10-undecenol and feedstocks such as vanillin and 5-hydroxy-2-methyl-furfuraldehyde. This demonstrates the effectiveness of hydroesterification to access bioderived polyesters with attractive cyclic and aromatic features.

Expanded versatility of hydroesterificative Polymerization via bioderived monomers

ACS Spring Meeting 2021

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