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

IF 14.7 1区综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES

Nature Communications Pub Date : 2024-01-24 DOI:10.1038/s41467-024-44892-1

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

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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.

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在琥珀酰亚胺阴离子型离子液体上将聚（琥珀酸盐）与胺升级循环为 N-取代的琥珀酰亚胺

将废弃聚合物化学转化为高附加值化学品对循环经济和可持续发展具有重要意义。在此，我们报告了通过琥珀酰亚胺阴离子基离子液体（ILs，如 1,8-二氮杂双环[5.4.0]十一-7-烯琥珀酰亚胺，[HDBU][Suc]），将含胺的聚琥珀酸盐（PSS）升级循环为 N-取代的琥珀酰亚胺。在 H2O 的辅助下，[HDBU][Suc]）表现出最佳性能，可以在温和和无金属的条件下将一系列 PSS 完全转化为琥珀酰亚胺衍生物和相应的二元醇。机理研究表明，阳离子-阴离子限制了 IL、H2O、酯基和氨基/酰胺基团之间的氢键相互作用，增强了氨基/酰胺基团中 N 原子的亲核性，提高了酯基中羰基 C 原子的亲电性。氨基/酰胺 N 原子攻击酯基的羰基 C 原子，导致聚酯中的羰基 C-O 键断裂，形成酰胺基。这种策略对于将聚(三亚甲基戊二酸酯)氨解成戊二酰亚胺和将聚(1,4-丁烯己二酸酯)氨解成己内酰胺也很有效。

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来源期刊

Nature Communications Biological Science Disciplines-

CiteScore

24.90

自引率

2.40%

发文量

6928

审稿时长

3.7 months

期刊介绍： Nature Communications, an open-access journal, publishes high-quality research spanning all areas of the natural sciences. Papers featured in the journal showcase significant advances relevant to specialists in each respective field. With a 2-year impact factor of 16.6 (2022) and a median time of 8 days from submission to the first editorial decision, Nature Communications is committed to rapid dissemination of research findings. As a multidisciplinary journal, it welcomes contributions from biological, health, physical, chemical, Earth, social, mathematical, applied, and engineering sciences, aiming to highlight important breakthroughs within each domain.