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Chemical Recycling of Thiol Epoxy Thermosets via Light-Driven C–C Bond Cleavage

Cite this: J. Am. Chem. Soc. 2023, 145, 20, 11151–11160
Publication Date (Web):May 11, 2023
https://doi.org/10.1021/jacs.3c00958
Copyright © 2023 American Chemical Society

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    Abstract

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    Epoxy thermosets are high-volume materials that play a central role in a wide range of engineering applications; however, technologies to recycle these polymers remain rare. Here, we present a catalytic, light-driven method that enables chemical recycling of industrially relevant thiol epoxy thermosets to their original monomer at ambient temperature. This strategy relies on the proton-coupled electron transfer (PCET) activation of hydroxy groups within the polymer network to generate key alkoxy radicals that promote the fragmentation of the polymer through C–C bond β-scission. The method fully depolymerizes insoluble thiol epoxy thermosets into well-defined mixtures of small-molecule products, which can collectively be converted into the original monomer via a one-step dealkylation process. Notably, this process is selective and efficient even in the presence of other commodity plastics and additives commonly found in commercial applications. These results constitute an important step toward making epoxy thermosets recyclable and more generally exemplify the potential of PCET to offer a more sustainable end-of-life for a diverse array of commercial plastics.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.3c00958 Additional source data for this study are accessible at DOI:10.5281/zenodo.7877010.

    • Experimental procedures, characterization data, and spectral data (PDF)

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    Cited By

    This article is cited by 3 publications.

    1. Steffan K. Kristensen, Alexander Ahrens, Bjarke S. Donslund, Troels Skrydstrup. Perspective on the Development of Monomer Recovery Technologies from Plastics Designed to Last. ACS Organic & Inorganic Au 2024, Article ASAP.
    2. Jinju Kim, Gyuri Kim, Jee-Hoon Kim, Hyun Woo, Yoonseong Jung, Hyejin Jang, Min Sang Kwon. Thioester-Based Latent Curing Agent for Thermally Conductive Epoxy Composites. ACS Applied Polymer Materials 2024, 6 (8) , 4568-4578. https://doi.org/10.1021/acsapm.4c00047
    3. Chengcheng Hu, Yu Jin, Wangmao Tian, Kangle Yan, Jie Wang, Liang Yuan. Photodegradable Dynamic Polyurethane Networks via Dithioacetals. Macromolecules 2024, 57 (4) , 1725-1733. https://doi.org/10.1021/acs.macromol.3c01875