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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

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Authors

Dara M. O'Brien

Rachel L. Atkinson

Ana A.C. Pacheco

Ryan Larder

Kristoffer Kortsen

Eduards Krumins

Alice J. Haddleton

Profile image of ROBERT STOCKMAN

ROBERT STOCKMAN robert.stockman@nottingham.ac.uk
Professor of Organic Chemistry



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.

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