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., Krumins, E., Haddleton, A. J., Alexander, C., Stockman, R. A., Howdle, S. M., & 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.