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

Sagnelli, Domenico; Vestri, Ambra; Curia, Silvio; Taresco, Vincenzo; Santagata, Gabriella; Johansson, Mats K.G.; Howdle, Steven M.

Abstract

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 (scCO2) 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 scCO2 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.

Citation

Sagnelli, D., Vestri, A., Curia, S., Taresco, V., Santagata, G., Johansson, M. K., & Howdle, S. M. (2021). Green enzymatic synthesis and processing of poly (cis-9,10-epoxy-18-hydroxyoctadecanoic acid) in supercritical carbon dioxide (scCO2). European Polymer Journal, 161, Article 110827. https://doi.org/10.1016/j.eurpolymj.2021.110827

• Journal Article Type: Article
• Acceptance Date: Oct 11, 2021
• Online Publication Date: Oct 16, 2021
• Publication Date: Dec 5, 2021
• Deposit Date: Oct 29, 2021
• Publicly Available Date: Apr 17, 2023
• Journal: European Polymer Journal
• Print ISSN: 0014-3057
• Electronic ISSN: 1873-1945
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 161
• Article Number: 110827
• DOI: https://doi.org/10.1016/j.eurpolymj.2021.110827
• Keywords: Organic Chemistry; Polymers and Plastics; General Physics and Astronomy; Materials Chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/6544055
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0014305721005619?via%3Dihub