Chemical Upcycling of Waste Poly(bisphenol A carbonate) to 1, 4, 2‐Dioxazol‐5‐ones and One‐Pot C−H Amidation. Issue 19 (2nd July 2021)

• Record Type: Journal Article
• Authors: Jung, Hyun Jin; Park, Sora; Lee, Hyun Sub; Shin, Hyun Gyu; Yoo, Yeji; Baral, Ek Raj; Lee, Jun Hee; Kwak, Jaesung; Kim, Jeung Gon
• Is Part Of: ChemSusChem. Volume 14:Issue 19(2021)
• Page Start: 4301
• Page End: 4306
• Publication Date: 2021-07-02
• Subjects: C−H amidation -- chemical recycling -- dioxazolone -- polycarbonate -- upcycling; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.202100885
• Languages: English
• ISSNs: 1864-5631

Abstract

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. Abstract : Make it green : Chemical upcycling of poly(bisphenol A carbonate) (PC) to synthetically valuable 1, 4, 2‐dioxazol‐5‐one is realized. In addition to toxic bisphenol A recovery, waste PC replaces phosgene or its derivatives in a carbonylation reaction, boosting the metrics of green chemistry.