Chemical Upcycling of Waste Poly(bisphenol A carbonate) to 1,4,2-Dioxazol-5-ones and One-Pot C-H Amidation

Hyun Jin Jung; Sora Park; Hyun Sub Lee; Hyun Gyu Shin; Yeji Yoo; Ek Raj Baral; Jun Hee Lee; Jaesung Kwak; Jeung Gon Kim

doi:10.1002/cssc.202100885

Chemical Upcycling of Waste Poly(bisphenol A carbonate) to 1,4,2-Dioxazol-5-ones and One-Pot C-H Amidation

ChemSusChem. 2021 Oct 5;14(19):4301-4306. doi: 10.1002/cssc.202100885. Epub 2021 Jul 2.

Authors

Hyun Jin Jung¹, Sora Park¹, Hyun Sub Lee¹, Hyun Gyu Shin¹, Yeji Yoo¹, Ek Raj Baral¹, Jun Hee Lee², Jaesung Kwak³, Jeung Gon Kim¹

Affiliations

¹ Department of Chemistry and Research Institute of Physics and Chemistry, Jeonbuk National University, Jeonju, 54896, Republic of Korea.
² Department of Advanced Materials Chemistry, Dongguk University, Gyeongju, 38066, Republic of Korea.
³ Infectious Diseases Therapeutic Research Center, Korea Research Institute of Chemical Technology (KRICT), Deajeon, 34114, Republic of Korea.

PMID: 34129287
DOI: 10.1002/cssc.202100885

Abstract

Chemical upcycling of poly(bisphenol A carbonate) (PC) was achieved in this study with hydroxamic acid nucleophiles, giving rise to synthetically valuable 1,4,2-dioxazol-5-ones and bisphenol A. Using 1,5,7-triazabicyclo[4.4.0]-dec-5-ene (TBD), non-green carbodiimidazole or phosgene carbonylation agents used in conventional dioxazolone synthesis were successfully replaced with PC, and environmentally harmful bisphenol A was simultaneously recovered. Assorted hydroxamic acids exhibited good-to-excellent efficiencies and green chemical features, promising broad synthetic application scope. In addition, a green aryl amide synthesis process was developed, involving one-pot depolymerization from polycarbonate to dioxazolone followed by rhodium-catalyzed C-H amidation, including gram-scale examples with used compact discs.

Keywords: C−H amidation; chemical recycling; dioxazolone; polycarbonate; upcycling.

Abstract

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