Issue 16, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Jan 2020
Accepted
19 Apr 2020
First published
01 May 2020
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2020,22, 5267-5273

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, 22, 5267 DOI: 10.1039/D0GC00338G

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements