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

Publication date: Available online 17 January 2020Source: European Polymer JournalAuthor(s): Dara M.O'Brien, Rachel L. Atkinson, Robert Cavanagh, Ana A.C. Pacheco, Ryan Larder, Kristoffer Kortsen, Eduards Krumins, Alice J. Haddleton, Cameron Alexander, Robert A. Stockman, Steven M. Howdle, Vincenzo TarescoAbstractIn 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-renewabl...
Source: European Polymer Journal - Category: Chemistry Source Type: research