Efficient Photolytic Breakdown of Waste Polystyrene Foam Using an “All-in-One” Photo-HAT Reagent at Ambient Conditions

Yusra Bahar Cakir, Ragip Talha Uzun, Huseyin Cem Kiliclar*, Kerem Kaya*, Steffen Jockusch, Yusuf Yagci, Baris Kiskan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Upcycling/recycling of waste polymers to reduce the exponentially increasing plastic pollution is an environmental subject of great importance. Accordingly, in this work, we propose the use of an “all-in-one” photolytic hydrogen atom transfer (photo-HAT) reagent (phenacyl bromide) that can in situ generate bromine radicals, acetophenone, HBr, and H2O2, resulting in a total of four well-established, potent intermediates for the photodegradation/photodepolymerization of waste polystyrene (PS) foam. Under ambient conditions, using ethyl acetate solvent and the stated photo-HAT catalyst, waste PS (Mn > 120 kg/mol) breaks down to oligomers with less than eight styrene units (Mn < 0.76 kg/mol) and to several organic compounds, such as aromatic ketones, oxygenated alkenes in conjunction with acetophenone and trace benzoic acid. A plausible reaction mechanism demonstrating the role of each in situ generated intermediate involved in this photodegradation is proposed. Herein, we present an efficient metal-free photo-oxidative degradation method for commercial PS using a cheap organic reagent at ambient sustainable conditions. Ultimately, this study provides a promising alternative to recent waste polymer valorization methods involving toxic transition metal salts and halogenated solvents.

Original languageEnglish
JournalACS Sustainable Chemistry and Engineering
DOIs
Publication statusAccepted/In press - 2024

Bibliographical note

Publisher Copyright:
© 2024 American Chemical Society.

Keywords

  • hydrogen atom transfer (HAT)
  • light-induced C−H abstraction
  • photo-oxidative degradation
  • polymer degradation
  • upcycling

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