Synthesis of methyl imidazole amine ionic liquid for ATRP reaction system

XUE Teng; ZHOU Jian; FU Tantan; TANG Erjun; ZHAO Dishun

doi:10.3969/j.issn.0438-1157.20161132

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Synthesis of methyl imidazole amine ionic liquid for ATRP reaction system

更新时间：2025-11-26

- Synthesis of methyl imidazole amine ionic liquid for ATRP reaction system
- CIESC Journal Issue S2, Pages: 159-163(2016)
- 作者机构：
  
  河北科技大学化学与制药工程学院,河北,石家庄,050018
- 作者简介：
- 基金信息：
- DOI：10.3969/j.issn.0438-1157.20161132
  CLC： TQ032.4}
- Online First：30 December 2016，
  
  Published：30 December 2016
- 稿件说明：
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XUE Teng, ZHOU Jian, FU Tantan, et al. Synthesis of methyl imidazole amine ionic liquid for ATRP reaction system[J]. CIESC Journal, 2016, (S2): 159-163.
DOI：

XUE Teng, ZHOU Jian, FU Tantan, et al. Synthesis of methyl imidazole amine ionic liquid for ATRP reaction system[J]. CIESC Journal, 2016, (S2): 159-163. DOI： 10.3969/j.issn.0438-1157.20161132.

摘要

以N-甲基咪唑为骨架引入1，2-二氯乙烷合成中间体氯化1-氯乙基-3-甲基咪唑（[CeMIM]Cl），再与1，3-丙二胺反应合成了氯化1-（丙基氨基）乙基-3-甲基咪唑离子液体（[N2C3MIM]Cl）。通过FT-IR、1H NMR对[N2C3MIM]Cl进行分析测试，确证了其化学结构。通过循环伏安法测得[N2C3MIM]Cl具有较低的氧化还原电势，为-0.522 V，与有机配体相比[N2C3MIM]Cl具有较好的配位性能。将[N2C3MIM]Cl与CuBr配位用于催化甲基丙烯酸甲酯（MMA）的原子转移自由基聚合（ATRP）反应，经凝胶渗透色谱法（GPC）测试证明[N2C3MIM]Cl对ATRP反应具有较好的可控性。原子吸收光谱测定聚合产物PMMA中Cu2+的残留量仅为270 mg·kg-1，表明与传统有机配体相比，[N2C3MIM]Cl有利于催化剂与聚合产物的分离。

Abstract

1-(Propyl amine)ethyl-3-methyl chloride ionic liquid ([N2C3MIM]Cl) was prepared on the base of N-methylimidazole by 1

2-dichloroethane to obtain the intermediates 1-chloro-ethyl-3-methyl chloride ionic liquid ([CeMIM]Cl)and then reacting with 1

3-propanediamine.The chemical structure of [N2C3MIM]Cl was confirmed by FT-IR and 1H NMR.[N2C3MIM]Cl possessed a lower REDOX potential (-0.522 V) through cyclic voltammetry measurement

[N2C3MIM]Cl presented a perfect coordination property compared with organic ligands.The obtained ionic liquid[N2C3MIM]Cl coordinated with CuBr was used to catalyze atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA)and it indicated by gel permeation chromatography (GPC) that the coordination ionic liquid[N2C3MIM]Cl presented the perfect controllability to the ATRP reactions.The residues of Cu2+ in polymerization product PMMA was only 270 mg·kg-1 by atomic absorption spectrometry determination.It showed that[N2C3MIM]Cl was conducive to the separation of catalyst from the obtained product compared with the traditional organic ligands.

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