Green enzymatic synthesis and processing of poly (cis-9,10-epoxy-18-hydroxyoctadecanoic acid) in supercritical carbon dioxide (scCO2)

Abstract

• Use of a green and sustainable synthetic strategy to CHA-based polyesters. • Low temperature (35–55 °C) polycondensation in scCO 2 achieved. • The valuable epoxy groups of the monomers were preserved. • Our process led to reasonably high molecular weight polyesters. There is significant potential for industrial use of renewables for a wide range of materials demanded by society. Plants, trees and algae are increasingly attracting attention as sustainable sources for functionalised and polymerizable building blocks. In particular, the outer bark of the birch tree ( Betula pendula ) is a side stream of the forestry industry with so far very little utilisation besides energy recovery. It is composed of a macromolecular network, suberin, that could provide a renewable, low cost and competitive resource. Within raw suberin is the potentially very useful multifunctional extract cis -9,10-epoxy-18-hydroxyoctadecanoic acid (CHA). Our drive has been to develop a green and sustainable synthetic strategy to CHA-based polyesters, by exploiting supercritical carbon dioxide (scCO 2 ) as a reaction medium and leveraging the regio- and chemo-selective properties of the biocatalyst Novozym 435 (Lipase B). Low temperature (35–55 °C) polycondensation in scCO 2 shows significant advantages compared to traditional polymerisation methods leading to reasonably high molecular weight polyesters. The mild synthetic conditions also preserve the valuable epoxy groups of the CHA which we show can be exploited by post-polymerisation functionalisation to create sustainable resins for bio-renewable coatings.