Issue 70, 2018, Issue in Progress

Small-scale screening of novel biobased monomers: the curious case of 1,3-cyclopentanediol

Abstract

In this work, we report on the small scale polycondensation and consecutive analysis of novel polyesters based on the potentially renewable 1,3-cyclopentanediol (CPdiol). To avoid evaporation of monomers during thin-film polymerization reactions, trimer pre-polyesters have been synthesized from the corresponding acid-chlorides with diol monomers. Polymerization of these trimers was explored by thermogravimetric analysis to identify potential side reactions, and to assess the ideal polymerization temperature. In general we observe that trans-1,3-cyclopentanediol exhibits good thermal stability up to 200 °C, whereas thermal dehydration of the alcohol end-groups occurs upon further heating. In contrast, for cis-1,3-cyclopentanediol, the ester bonds of the cyclopentane end-groups become labile, thereby generating carboxylic acid end-groups, and 3-cyclopentenol already at 180 °C. The thermal dehydration reactions yield double bond end-groups, which in turn facilitate cross-linking through cross-coupling and Diels–Alder reactions, leading to an increase in molecular weight. Despite the limited thermal stability of CPdiol, here we demonstrate that polymerization of CPdiol can successfully be achieved in thin-film polycondensation conditions at 180 °C, yielding molecular weights well above 10 kg mol−1.

Graphical abstract: Small-scale screening of novel biobased monomers: the curious case of 1,3-cyclopentanediol

Supplementary files

Article information

Article type
Paper
Submitted
24 Oct 2018
Accepted
21 Nov 2018
First published
29 Nov 2018
This article is Open Access
Creative Commons BY license

RSC Adv., 2018,8, 39818-39828

Small-scale screening of novel biobased monomers: the curious case of 1,3-cyclopentanediol

G. J. Noordzij, C. H. J. T. Dietz, N. Leoné, C. H. R. M. Wilsens and S. Rastogi, RSC Adv., 2018, 8, 39818 DOI: 10.1039/C8RA08811J

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