Reactive phenolic solvents applied to the synthesis of renewable aromatic polyesters with high isosorbide content

Bruno Bottega Pergher; Narcisa Girigan; Sietse Vlasblom; Daniel H Weinland; Bing Wang; Robert-Jan van Putten; Gert-Jan M Gruter

doi:10.1039/d2py01578a

Reactive phenolic solvents applied to the synthesis of renewable aromatic polyesters with high isosorbide content

Polym Chem. 2023 Jun 26;14(27):3225-3238. doi: 10.1039/d2py01578a. eCollection 2023 Jul 11.

Authors

Bruno Bottega Pergher¹, Narcisa Girigan¹, Sietse Vlasblom¹, Daniel H Weinland¹, Bing Wang², Robert-Jan van Putten^{1

2}, Gert-Jan M Gruter^{1

2}

Affiliations

¹ Van't Hoff Institute of Molecular Sciences, University of Amsterdam P.O. Box 94720 1090GS Amsterdam The Netherlands g.j.m.gruter@uva.nl.
² Avantium Chemicals BV Zekeringstraat 29 1014BV Amsterdam The Netherlands.

Abstract

High boiling point phenolic reactive solvents like p-cresol could play a key role in improving the synthesis of aromatic polyesters with a high content of secondary diols such as isosorbide. Previously, our group showed that this method significantly improves the synthesis of poly(isosorbide succinate). In this work, terephthalic acid and 2,5-furandicarboxylic acid were used as building blocks for the synthesis of high T_g polyesters with high isosorbide content (>30 mol% of diols) and high molecular weight (M_n > 24 kg mol^-1). A number of reactive and non-reactive solvents were tested in this work, and the results clearly point to a significant improvement when using reactive solvents, in terms of molecular weight and polycondensation time, especially for the case of p-cresol. The synthesis method was successfully scaled to 1 kg, showing promise for production at industrial scale. A method to remove these solvents (including end groups) from the polymers, which uses small excesses of isosorbide (1.5-3.0%) in the feed, is also presented.