New renewably-sourced polyesters from limonene-derived monomers

Abstract

The functionalisation of limonene has enabled the synthesis of two renewably-sourced monomers for the formation of terpene-derived polyesters. Three methods for the synthesis of the novel hydroxy-acid 6 are reported and their green-credentials scrutinised through comparison of their sustainability-metrics. Step-growth homo-polymerisation of 6 is demonstrated to yield a low molecular weight (2.6 kDa) novel polyester with 100% of its carbon content originating from the terpene starting material. The corresponding diol 2 is shown to act as a co-monomer with a renewable diacid. The resultant polyesters display impressive M_ns of up to 30 kDa with T_gs between −6 and 24 °C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.