Upcycling Poly(succinates) with Amines to N-substituted Succinimides over Succinimide Anion-based Ionic Liquids

Overview

Journal Nat Commun

Specialty Biology

Date 2024 Jan 24

PMID 38267443

Authors

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

Affiliations

Soon will be listed here.

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 HO, [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, HO, 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.

Citing Articles

Upcycling waste commodity polymers into high-performance polyarylate materials with direct utilization of capping agent impurities.

Li C, Yan G, Dong Z, Zhang G, Zhang F Nat Commun. 2025; 16(1):2482.

PMID: 40074773 PMC: 11903651. DOI: 10.1038/s41467-025-57821-7.

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