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Scalable synthesis and polymerisation of a β-angelica lactone derived monomer

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Abstract

Bio-based levulinic acid is easily ring-closed to α-angelica lactone (α-AL). α-AL can be isomerized to the conjugated β-AL under the influence of base, but since this is an equilibrium mixture it is very hard to devise a scalable process that would give pure β-AL. This problem was circumvented by distilling the equilibrium mixture to obtain a 90 : 10 mixture of β- and α-AL in 88% yield. This mixture was used for Diels–Alder reactions on 3 terpenes and on cyclopentadiene in up to 100 g scale. The latter DA adduct was subjected to a ROMP reaction catalysed by the Grubbs II catalyst. The resulting polymer has some similarities to poly-norbornene but is more polar. The polymer can be processed into films with very good transparency.

Graphical abstract: Scalable synthesis and polymerisation of a β-angelica lactone derived monomer

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Article information


Submitted
27 Jan 2020
Accepted
19 Apr 2020
First published
01 May 2020

This article is Open Access

Green Chem., 2020, Advance Article
Article type
Paper

Scalable synthesis and polymerisation of a β-angelica lactone derived monomer

A. Dell'Acqua, B. M. Stadler, S. Kirchhecker, S. Tin and J. G. de Vries, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC00338G

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