Issue 5, 2024

Selective poly(vinyl ether) upcycling via photooxidative degradation with visible light

Abstract

Poly(vinyl ethers) (PVEs) have many applications, such as adhesives, lubricants, and anticorrosive agents, thanks to their elastic, nonirritating, and chemically inert properties. The recycling of PVEs remains largely underexplored, and current methods lack generality towards other polymer classes. Thus, the chemical upcycling of PVE into small molecule feedstocks would provide an alternative approach to combat these current issues. Here, we report a visible light-mediated method of upcycling poly(isobutyl vinyl ether) (PIBVE) into small molecules via photooxidative degradation using chlorine or bromine radicals. PIBVE can be degraded to low molecular weight oligomers within 2 h, producing good yields of alcohols, aldehydes, and carboxylic acids. Mechanistic studies suggest that hydrogen atom transfer (HAT) from the backbone or the side chain leads to small molecule generation via oxidative cleavages. Additionally, this protocol was applied to a copolymer of poly(methyl acrylate-co-isobutyl vinyl ether) to demonstrate the preference for the degradation of polymers bearing more electron-rich C–H bonds through a judicious choice of abstraction agent. Ultimately, we show that photooxidative degradation enables the selective chemical upcycling of PVEs as a method of plastic waste valorization.

Graphical abstract: Selective poly(vinyl ether) upcycling via photooxidative degradation with visible light

Supplementary files

Article information

Article type
Edge Article
Submitted
20 okt 2023
Accepted
22 dec 2023
First published
27 dec 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 1840-1845

Selective poly(vinyl ether) upcycling via photooxidative degradation with visible light

D. L. Langer, S. Oh and E. E. Stache, Chem. Sci., 2024, 15, 1840 DOI: 10.1039/D3SC05613A

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