A ‘greener’ one-pot synthesis of monoterpene-functionalised lactide oligomers

O'Brien, Dara M.; Atkinson, Rachel L.; Cavanagh, Robert; Pacheco, Ana A.C.; Larder, Ryan; Kortsen, Kristoffer; Krumins, Eduards; Haddleton, Alice J.; Alexander, Cameron; Stockman, Robert A.; Howdle, Steven M.; Taresco, Vincenzo

Abstract

© 2020 Elsevier Ltd In this work we aimed to achieve a totally sustainable Ring Opening Polymerisation (ROP) process, by harmonising the use of naturally occurring or derivable initiators and the green solvent 2-Methyltetrahydrofuran (2-MeTHF). First, a library of novel monoterpene-alcohols and existing terpenoids was used to provide renewably sourced initiators for a metal-free ROP synthetic step. A number of these initiators are derived from waste materials, further improving their sustainability. Secondly, we selected lactide (LA) as a monomer, because not only is it derived from biomass, but its resultant polymers are biocompatible and biodegradable. Interestingly, these new polymers self-assembled in water producing well defined, biocompatible nanoparticles (NPs) via direct nanoprecipitation without the use of additional stabilisers. We have highlighted a novel and promising (ROP) approach to produce biodegradable, amphiphilic ester-based macromolecules, based on lactide and terpenes (as initiators) in a green solvent, 2-MeTHF thus reducing solvent toxicity in an efficient, simple and sustainable new synthesis. The monoterpenes may provide a highly functionalisable and bio-renewable toolbox for a new generation of ROP initiators.

Citation

O'Brien, D. M., Atkinson, R. L., Cavanagh, R., Pacheco, A. A., Larder, R., Kortsen, K., …Taresco, V. (2020). A ‘greener’ one-pot synthesis of monoterpene-functionalised lactide oligomers. European Polymer Journal, 125, 109516. https://doi.org/10.1016/j.eurpolymj.2020.109516

• Journal Article Type: Article
• Acceptance Date: Jan 16, 2020
• Online Publication Date: Jan 17, 2020
• Publication Date: Feb 15, 2020
• Deposit Date: Jan 31, 2020
• Publicly Available Date: Jul 18, 2021
• Journal: European Polymer Journal
• Print ISSN: 0014-3057
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 125
• Pages: 109516
• DOI: https://doi.org/10.1016/j.eurpolymj.2020.109516
• Keywords: Organic Chemistry; General Physics and Astronomy; Polymers and Plastics
• Public URL: https://nottingham-repository.worktribe.com/output/3839893
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0014305719323766
• Additional Information: This article is maintained by: Elsevier; Article Title: A ‘greener’ one-pot synthesis of monoterpene-functionalised lactide oligomers; Journal Title: European Polymer Journal; CrossRef DOI link to publisher maintained version: https://doi.org/10.1016/j.eurpolymj.2020.109516; Content Type: article; Copyright: © 2020 Elsevier Ltd. All rights reserved.