Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 7, Issue 2, Pages 2751-2762Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.8b05926
Keywords
Renewable resources; Glycerol; Dimethyl carbonate; Fatty acid methyl ester; Olefinic monomer; Allylic monomer; Cobalt-mediated radical polymerization; Vinyl acetate
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Funding
- European Community [641640]
- Fonds National pour la Recherche Scientifique (F.RS.-FNRS)
- Fonds Wetenschappelijk Onderzoek - Vlaanderen (FWO) [O019618F, EOS: 30902231]
- F.R.S.-FNRS
- Marie Curie Actions (MSCA) [641640] Funding Source: Marie Curie Actions (MSCA)
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In light of fossil fuel depletion and a general necessity for sustainable development, the synthesis of polymers from renewable resources is gaining more and more importance, yet industrially relevant radical polymerizations still struggle with the incorporation of renewable resources as the number of natural molecules containing suitable double bonds is limited. Herein, we present the sustainable synthesis of nonactivated allylic and olefinic carbonate monomers from renewable resources in a solventless one-pot transesterification reaction. We subsequently confirm the first controlled radical copolymerization of such challenging nonactivated monomers with vinyl acetate, in which molecular weights above 10 000 g.mol(-1) were reached. The controlled nature of the copolymerizations was verified by the low dispersities obtained and the linear increase in molecular weights with conversion. The so-prepared copolymers were purified using sustainable extractions by supercritical carbon dioxide (scCO(2)), which allowed recovery of up to 58% of unused monomer. Using FT-IR and NMR spectroscopy, the incorporation of the renewable monomers into the copolymer in up to 49 mol % was confirmed, which is the highest reported to date. The combination of a sustainable double bond functionalization pathway with controlled radical polymerizations highlights the potential of radical polymerizations in the quest for renewable polymers and introduces a new set of monomers for this technique.
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