Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids

Fengtian Wu; Yuepeng Wang; Yanfei Zhao; Shaojuan Zeng; Zhenpeng Wang; Minhao Tang; Wei Zeng; Ying Wang; Xiaoqian Chang; Junfeng Xiang; Zongbo Xie; Buxing Han; Zhimin Liu

doi:10.1038/s41467-024-44892-1

Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids

Nat Commun. 2024 Jan 24;15(1):712. doi: 10.1038/s41467-024-44892-1.

Authors

Fengtian Wu^{1

2}, Yuepeng Wang^{1

3}, Yanfei Zhao^{1

3}, Shaojuan Zeng⁴, Zhenpeng Wang¹, Minhao Tang^{1

3}, Wei Zeng^{1

3}, Ying Wang^{1

3}, Xiaoqian Chang^{1

3}, Junfeng Xiang¹, Zongbo Xie², Buxing Han^{1

3}, Zhimin Liu^{5

6}

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, Key Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190, Beijing, P. R. China.
² Jiangxi Province Key Laboratory of Polymer Micro/Nano Manufacturing and Devices, Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Economic Development Zone, Guanglan Avenue 418, Nanchang, 330013, P. R. China.
³ University of Chinese Academy of Sciences, Beijing, 100049, P. R. China.
⁴ Beijing Key Laboratory of Ionic Liquids Clean Process, State Key Laboratory of Multiphase Complex Systems, Institute of Process Engineering, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
⁵ Beijing National Laboratory for Molecular Sciences, Key Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190, Beijing, P. R. China. liuzm@iccas.ac.cn.
⁶ University of Chinese Academy of Sciences, Beijing, 100049, P. R. China. liuzm@iccas.ac.cn.

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.

Abstract

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