Photooxidation of Polyolefins to Produce Materials with In-Chain Ketones and Improved Materials Properties

Xin Liu, Zhitao Hu, Brandon Portela, Emma Rettner, Agustin Pineda, Joel Miscall, Nicholas Rorrer, Amber Krummel, Robert Paton, Garret Miyake

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we report a selective photooxidation of commodity postconsumer polyolefins to produce polymers with in-chain ketones. The reaction does not involve the use of catalyst, metals, or expensive oxidants, and selectively introduces ketone functional groups. Under mild and operationally simple conditions, yields up to 1.23 mol % of in-chain ketones were achieved. Installation of in-chain ketones resulted in materials with improved adhesion of the materials and miscibility of mixed plastics relative to the unfunctionalized plastics. The introduction of ketone groups into the polymer backbone allows these materials to react with diamines, forming dynamic covalent polyolefin networks. This strategy allows for the upcycling of mixed plastic waste into reprocessable materials with enhanced performance properties compared to polyolefin blends. Mechanistic studies support the involvement of photoexcited nitroaromatics in consecutive hydrogen and oxygen atom transfer reactions.
Original languageAmerican English
JournalAngewandte Chemie - International Edition
DOIs
StatePublished - 2024

NREL Publication Number

  • NREL/JA-2800-92640

Keywords

  • ketone groups
  • mixed plastic waste
  • photooxidation
  • upcycling

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