Issue 11, 2023

Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis

Abstract

The chemical depolymerisation of poly(bisphenol A carbonate) (BPA-PC) was studied using α-hydroxyketones as nucleophiles to give bisphenol A as the original monomer and the corresponding vinylene carbonates as co-products. The optimisation revealed that 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) is an efficient organocatalyst to perform this reaction under mild conditions (25 °C in 2-MeTHF). The success of TBD was attributed to the fact that it can both activate α-hydroxyketones and BPA-PC, through hydrogen bonding. The substrate scope was then investigated with a range of α-hydroxyketones to give vinylene carbonates (symmetrical and unsymmetrical, aromatic, heteroaromatic and alkyl) with moderate to high yields (30–97%, 13 examples). Scale-up experiments were also conducted to highlight the synthetic utility of this method. Finally, it was demonstrated that vinylene carbonates can be produced from waste polycarbonate contained in compact disks (CDs) and other BPA-PC containing materials, thus providing a safe and economical access to these species.

Graphical abstract: Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis

Supplementary files

Article information

Article type
Paper
Submitted
22 11 2022
Accepted
27 4 2023
First published
04 5 2023
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2023,25, 4282-4291

Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis

K. Onida, M. Fayad, S. Norsic, O. Boyron and N. Duguet, Green Chem., 2023, 25, 4282 DOI: 10.1039/D2GC04413G

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