New renewably-sourced polyesters from limonene-derived monomers

Thomsett, Megan R.; Moore, Jonathan C.; Buchard, Antoine; Stockman, Robert A.; Howdle, Steven M.

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 Mns of up to 30 kDa with Tgs between −6 and 24 °C. These materials have been shown to depolymerise under basic conditions for reclamation of the diol monomer 2.

Citation

Thomsett, M. R., Moore, J. C., Buchard, A., Stockman, R. A., & Howdle, S. M. (2019). New renewably-sourced polyesters from limonene-derived monomers. Green Chemistry, 21(1), 149-156. https://doi.org/10.1039/c8gc02957a

• Journal Article Type: Article
• Acceptance Date: Nov 26, 2018
• Online Publication Date: Nov 26, 2018
• Publication Date: Jan 7, 2019
• Deposit Date: Mar 4, 2019
• Publicly Available Date: Nov 27, 2019
• Journal: Green Chemistry
• Print ISSN: 1463-9262
• Electronic ISSN: 1463-9270
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 21
• Issue: 1
• Pages: 149-156
• DOI: https://doi.org/10.1039/c8gc02957a
• Keywords: Pollution; Environmental chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/1603077
• Publisher URL: https://pubs.rsc.org/en/Content/ArticleLanding/2019/GC/C8GC02957A#!divAbstract
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : Megan R. Thomsett (ORCID); : Jonathan C. Moore (ORCID); : Jonathan C. Moore (ResearcherID); : Antoine Buchard (ORCID); : Antoine Buchard (ResearcherID); : Robert A. Stockman (ORCID); : Robert A. Stockman (ResearcherID); : Steven M. Howdle (ORCID); : Single-blind; : Received 18 September 2018; Accepted 26 November 2018; Accepted Manuscript published 26 November 2018; Advance Article published 4 December 2018; Version of Record published 2 January 2019
• Contract Date: Mar 4, 2019