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- Title
Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids.
- Authors
Wu, Fengtian; Wang, Yuepeng; Zhao, Yanfei; Zeng, Shaojuan; Wang, Zhenpeng; Tang, Minhao; Zeng, Wei; Wang, Ying; Chang, Xiaoqian; Xiang, Junfeng; Xie, Zongbo; Han, Buxing; Liu, Zhimin
- Abstract
The chemical transformation of waste polymers into value-added chemicals is of significance for circular economy and sustainable development. Herein, we report upcycling poly(succinates) (PSS) with amines into N-substituted succinimides over succinimide anion-based ionic liquids (ILs, e.g, 1,8-diazabicyclo[5.4.0]undec-7-ene succinimide, [HDBU][Suc]). Assisted with H2O, [HDBU][Suc]) showed the best performance, which could achieve complete transformation of a series of PSS into succinimide derivatives and corresponding diols under mild and metal-free conditions. Mechanism investigation indicates that the cation-anion confined hydrogen-bonding interactions among IL, H2O, ester group, and amino/amide groups, strengthens nucleophilicity of the N atoms in amino/amide groups, and improves electrophilicity of carbonyl C atom in ester group. The attack of the amino/amide N atom on carbonyl C of ester group results in cleavage of carbonyl C-O bond in polyester and formation of amide group. This strategy is also effective for aminolysis of poly(trimethylene glutarate) to glutarimides, and poly(1,4-butylene adipate) to caprolactone diimides. Ionic liquids have been employed in dissolution and chemical degradation of waste polymers. Here the authors report a cation-anion confined hydrogen-bonding catalysis strategy to deconstruct poly(succinates) into N-substituted succinimides over ionic liquids.
- Subjects
SUCCINATES; SUCCINIMIDES; POLYESTERS; AMIDES; CHEMICAL amplification; IONIC liquids; GLYCOLS; CIRCULAR economy; POLYBUTENES
- Publication
Nature Communications, 2024, Vol 15, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-024-44892-1