Imidazole type functional ion liquid having N-substituted amide structure fragment, and its prepn. method

A technology of ionic liquids and structural fragments, applied in the direction of organic chemistry, etc., to achieve good application prospects, improve efficiency, improve catalytic activity and selectivity

Inactive Publication Date: 2006-04-12
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Up to now, there has been no report on the synthesis of functionalized ionic liquids containing amide moieties via ionic phase reactions

Method used

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  • Imidazole type functional ion liquid having N-substituted amide structure fragment, and its prepn. method
  • Imidazole type functional ion liquid having N-substituted amide structure fragment, and its prepn. method
  • Imidazole type functional ion liquid having N-substituted amide structure fragment, and its prepn. method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1. Preparation of 1-ethyl-3-(N,N-diethylcarbamoylmethyl) imidazole tetrafluoroborate (DEEImBF 4 )

[0046] A, prepare 1-ethyl-3-carboxymethylimidazolium tetrafluoroborate (CMEImBF 4 ) ionic liquid

[0047] Chloroacetic acid 94g, (1.0mol), was added in batches to N-ethylimidazole 94g, (1.0mol), heated at 70-80°C for 4h, cooled, washed twice with 20mL acetonitrile, and evaporated to dryness to obtain 1- Ethyl-3-carboxymethylimidazolium chloride (CMEImCl), yield 95%. CMEImCl94g, (0.5mol) and NaBF 4 54g, (0.5mol) was dissolved in 500mL water, reacted at 80°C for 4h, cooled slightly, fully extracted with dichloromethane, combined organic phase, MgSO 4 Drying, evaporation of solvent to obtain viscous liquid 1-ethyl-3-carboxymethylimidazolium tetrafluoroborate (CMEImBF 4 ), yield 86%.

[0048] B. Preparation of 1-ethyl-3-(N, N-diethylcarbamoylmethyl) imidazole tetrafluoroborate (DEEImBF 4 ) ionic liquid

[0049] CMEImBF 4 Add 0.2 (mol), diethylamine (0.2mol), ...

Embodiment 2

[0051] Example 2. Preparation of 1-ethyl-3-(N-n-butylcarbamoylmethyl) imidazole tetrafluoroborate (BEImBF 4 )

[0052] According to the CMEImBF prepared in Example 1 4 (0.2mol), n-butylamine 14.6g, (0.2mol), DIC (0.2mol) were added to a 100mL flask, heated to reflux for 1-2h, stopped, washed thoroughly with ether to remove other impurities in the reaction, and then distilled Dry solvent. Get BEImBF 4 , the yield was 89%, and it was a yellow liquid at room temperature.

[0053]

Embodiment 3

[0054] Example 3. Preparation of 1-ethyl-3-(C-(morpholin-4-yl)-formylmethyl)imidazole tetrafluoroborate (MEImBF 4 )

[0055] According to the CMEImBF prepared in Example 1 4 (0.2mol), Morpholine 26.1g, (0.3mol), DIC (0.2mol), CaCl 2 (0.2mol) was added into a 100mL flask, heated to reflux for 10-12 hours, stopped, centrifuged to remove insoluble inorganic salts, and other impurities in the reaction were removed by distillation. Get MEImBF 4 , the yield was 83%, and it was a yellow liquid at room temperature.

[0056]

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Abstract

This invention provides functional ion liquid of a imidazole type with N-amido- structural segment, the structure is shown as the formula: it is characterized by : when nú¢2 or 3ú¼Rú¢alkyl with straight or branched chain of C1-C12ú”R1R2ú¢Híóstraight alkyl of C1-C12íóbranched alkyl of C1-C12íó -(CH2)m- or -(CH2CH2)2-Oú¼mú¢4-5ú” Xú¢ClíóBF4íóPF6íóCF3SO3(TfO)íóCF3COO(TA),N(CF3SO2)2(NTf2) or NO3íúThe characteristics and innovation of this invent are: 1. preparing functional ion liquid of an Imidazole type with N-amido- structural segment, enriching variety of ion liquid. 2. Providing a preparation method of one familiar functional ion liquid from another one familiar functional ion liquid through ion phase reaction. 3. This invention has the characteristics of broad source of raw material for reaction, low cost, simple equipment , convenient operation, mild reaction condition, easy controlled condition, good quality of the products, high purity, high yield etc., it is suitable for commercial production and application.

Description

technical field [0001] The invention relates to an imidazole functionalized ionic liquid containing N-substituted amide structural fragments and a preparation method for an ionic phase, and belongs to the field of new chemical materials and their preparation. Background technique [0002] Ionic liquids are substances that are liquid at or near room temperature (<100° C.) and are composed of organic cations and inorganic anions. The early research on ionic liquids was mainly concentrated in the field of electrochemistry, and ionic liquids are also widely used in the research of organic synthesis reactions. The main advantage of the application of ionic liquids in organic synthesis reactions is that the reactions carried out in ionic liquids can not only effectively eliminate the environmental pollution caused by the use of molecular solvents, but also obtain better yields or selectivities. Sometimes ionic liquids can also It shows a certain catalytic effect, so that many ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/02
Inventor 刘宝友魏福祥韩菊董建芳
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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