超声辅助的异喹啉-离子液体的合成和表征

doi:10.3785/j.issn.1008-9497.2022.04.012

浙江大学学报（理学版）

2022, Vol. 49

Issue (4): 481-488 DOI: 10.3785/j.issn.1008-9497.2022.04.012

化学

超声辅助的异喹啉-离子液体的合成和表征

尹洋¹,马东¹,陈颖露¹,颜逸韬¹,商志才¹,俞建忠²(

),吴军¹(

)

^1.浙江大学化学系，浙江杭州 310027
^2.浙江省农业科学院农产品质量安全与营养研究所农产品质量安全国家重点实验室，浙江杭州 310021

Ultrasound-assisted synthesis and characterization of isoquinoline-based ionic liquids

Yang YIN¹,Dong MA¹,Yinglu CHEN¹,Yitao YAN¹,Zhicai SHANG¹,Jianzhong YU²(

),Jun WU¹(

)

^1.Department of Chemistry，Zhejiang University，Hangzhou 310027，China
^2.State Key Laboratory for Quality and Safety of Agro-Products，Institute of Agro-Product Safety and Nutrition，Zhejiang Academy of Agricultural Sciences，Hangzhou 310021，China

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摘要：

为解决传统加热法合成异喹啉-离子液体存在的问题，开发了一种超声辅助合成异喹啉-离子液体的方法。通过异喹啉季铵化过程的对比研究，证明了该方法具有环保性强、产率高、反应时间短等优点。将其扩展至阴离子交换反应，发现超声辐射法有效促进了异喹啉溴化物与简单阴离子［N（CF₃SO₂）₂］^-和［PF₆］^-，以及与复杂阴离子2，4-二氯苯氧乙酸的阴离子交换反应。对所得到的异喹啉-离子液体进行了结构表征以及热行为和溶解度的研究和讨论。结果表明，所得液体具有良好的热稳定性，为快速、高效建立绿色多功能化离子液体库奠定了基础。

关键词： 超声; 异喹啉; 离子液体; 绿色方法

Abstract:

To solve the problems in the conventional thermal heating synthesis of isoquinoline-based ionic liquids, an ultrasound-assisted synthesis of isoquinoline-based ionic liquids was developed. The comparative study of the quaternization process of isoquinoline proved that the method has apparent advantages over conventional thermal heating, i.e., ecofriendly nature, higher yield, and shorter reaction time. The ultrasonic method was then extended to the anion exchange reaction. The results demonstrated that the use of ultrasound irradiation efficiently promoted the anion-exchange reaction of isoquinolinium bromides with simple anions [N(CF₃SO₂)₂]^- and [PF₆]^-. It was also found that the anion-exchange reactions of isoquinolinium bromides with complex 2,4-dichlorophenoxyacetic acid anion were realized under ultrasonic conditions, which could not be achieved under the conventional heating method. The structure characterization, thermal behavior, and solubility of the obtained ionic liquids were investigated and discussed. All ionic liquids exhibited good thermal stability. This article thus provides a rapid and efficient method for the establishment of a multifunctionalized ionic liquids library.

Key words: ultrasound isoquinoline ionic liquids green method

收稿日期: 2021-04-06 出版日期: 2022-07-13

CLC:

O 62

基金资助: 国家自然科学基金资助项目(31471807)

通讯作者: 俞建忠,吴军 E-mail: jhxsyiz@163.com;wujunwu@zju.edu.cn

作者简介: 尹洋（1994—），ORCID：https：//orcid.org/0000-0002-7198-0718，女，硕士，主要从事功能化离子液体研究.

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引用本文:

尹洋,马东,陈颖露,颜逸韬,商志才,俞建忠,吴军. 超声辅助的异喹啉-离子液体的合成和表征[J]. 浙江大学学报（理学版）, 2022, 49(4): 481-488.

Yang YIN,Dong MA,Yinglu CHEN,Yitao YAN,Zhicai SHANG,Jianzhong YU,Jun WU. Ultrasound-assisted synthesis and characterization of isoquinoline-based ionic liquids. Journal of Zhejiang University (Science Edition), 2022, 49(4): 481-488.

链接本文:

https://www.zjujournals.com/sci/CN/10.3785/j.issn.1008-9497.2022.04.012 或 https://www.zjujournals.com/sci/CN/Y2022/V49/I4/481

图1 异喹啉-离子液体的两步合成

表1 最佳反应条件的筛选

表2 异喹啉季铵化反应在超声辐射法与传统加热法下的对比

表3 超声辐射法下异喹啉的季铵化反应

图2 异喹啉与2-溴丙酸甲酯的选择性反应

表4 超声辐射法下阴离子交换反应

表5 异喹啉-离子液体和盐的热分析

图3 不同链长的烷基取代基的异喹啉溴化物的热分析

表6 25 ℃下异喹啉-离子液体和盐的溶解度

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