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Cationic N-substituted aniline ionic liquid and preparation method thereof

An aniline and cationic technology, applied in organic chemistry and other fields

Inactive Publication Date: 2020-05-05
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] But, so far, there is no any report about the ionic liquid containing N-substituted aniline structure

Method used

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  • Cationic N-substituted aniline ionic liquid and preparation method thereof
  • Cationic N-substituted aniline ionic liquid and preparation method thereof
  • Cationic N-substituted aniline ionic liquid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0041] According to a preferred embodiment of the present invention, step 1 includes the following sub-steps:

[0042] Step 1-1, preparing N-phenylethanolamine, and then adding hydrobromic acid at -5 to 5°C;

[0043] Step 1-2: Stir at low temperature (-10-10°C) for 20-40 minutes, then stir at room temperature (20-40°C) for 20-40 minutes to react;

[0044] Step 1-3, post-treatment after the reaction to obtain the N-phenylethanolamine hydrobromide.

[0045] In a further preferred embodiment, in step 1-1, the molar ratio of N-phenylethanolamine to hydrobromic acid is 1:(1-3), preferably 1:(1-2).

[0046] In a further preferred embodiment, in step 1-3, the post-treatment is carried out as follows: first rotary evaporation, redissolving, then performing water removal treatment and filtering, and finally rotary evaporation to remove the solvent.

[0047] According to a preferred embodiment of the present invention, step 2 includes the following sub-steps:

[0048] Step 2-1, addin...

Embodiment 1

[0074] Add 6.8780g of N-phenylethanolamine to a 100mL round bottom flask, add 8.1355g of hydrobromic acid at 0°C, stir in an ice-water bath for 30min, and then stir at room temperature for 30min. Remove water by rotary evaporation, add chloroform to dissolve and dry with anhydrous sodium sulfate, filter, and remove solvent by rotary evaporation to obtain light yellow N-phenylethanolamine hydrobromide solid. The yield was 86.3%.

[0075] Add 4.68mmol of N-phenylethanolamine hydrobromide into a two-neck flask, add 5mL of chloroform to dissolve, pass argon to remove oxygen, slowly drop 0.6mL of phosphorus tribromide into the flask, and stir in a water bath at 40°C for 5h. The reaction was quenched by adding 5 mL of deionized water, extracted three times with chloroform, and the organic phase was rotary evaporated to obtain N-phenylbromoethylamine hydrochloride as a white solid with a yield of 62.9%.

[0076] Dissolve N-phenylbromoethylamine hydrochloride in water, adjust the pH ...

Embodiment 2

[0080] Repeat the process of Example 1 to prepare N-phenylbromoethylamine.

[0081] Take 3.1011g of N-phenylbromoethylamine, 1.0560g of imidazole and 10mL of acetonitrile in a round bottom flask, and magnetically stir in an oil bath at 70°C for 5h. Precipitate with ether and wash with acetonitrile three times to obtain a white solid. Dry at 60°C under vacuum.

[0082] The NMR spectrum of the product is as figure 2 As shown, the test conditions: 1 H NMR, 400MHz, solvent is dimethyl sulfoxide (DMSO), obtains following result through analysis: the position of the hydrogen in the product structure is as follows figure 2 In the structural formula, the chemical shift δ of H at m is 9.03ppm (1H), the chemical shift δ of H at g and h is 7.76ppm (2H), and the chemical shift δ of H at e is 7.05ppm (4H), d , The chemical shift δ of H at f is 6.54ppm (6H), the chemical shift δ of H at b is 4.25ppm (4H), and the chemical shift δ of H at a is 3.37ppm (4H). The displacement of each pea...

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Abstract

The invention discloses a cationic N-substituted aniline ionic liquid, wherein an N-substituted aniline structure is contained in positive ions, and preferably, the structure of the cationic N-substituted aniline ionic liquid is shown as formula (I). A preparation method of the cationic N-substituted aniline ionic liquid comprises the following steps: firstly preparing N-phenylethanolamine hydrobromide, then preparing N-phenylethanolamine bromide from N-phenylethanolamine hydrobromide, and finally reacting N-phenylethanolamine bromide with compounds as shown in formulas (II-1) to (II-14) to obtain the cationic N-substituted aniline ionic liquid. The cationic N-substituted aniline ionic liquid has the properties and applications of common ionic liquid (such as serving as a reaction medium,an additive of a polymer material and the like), can be used as a monomer, can also be used as a reaction monomer to prepare ionic liquid polyaniline derivative through self oxidative polymerization or oxidative copolymerization with other monomers, and can also be combined with other polymerization means (such as free radical polymerization and the like) to prepare ionic liquid polyaniline derivatives and compounds of the ionic liquid polyaniline derivatives and other polymers.

Description

technical field [0001] The invention relates to the field of ionic liquids, in particular to an N-substituted aniline ionic liquid, in particular to a cationic N-substituted aniline ionic liquid and a preparation method thereof. Background technique [0002] Ionic liquids are composed of cations and anions, and are generally liquid below 100 °C. Ionic liquids have many special properties, such as: designable structure, non-volatile, non-flammable and explosive, good chemical and thermal stability, wide electrochemical window, and can be used as reaction catalysts and solvents. Among the ionic liquids synthesized and studied more at present, the cations are mainly 1,3-dialkylimidazolium cations, alkylpyridinium cations, quaternary ammonium salt cations, quaternary phosphonium salts, etc., and the anions are mostly BF 4 - 、PF 6 - 、Tf 2 N - 、CF 3 COO - Wait. [0003] However, so far, there has not been any report on ionic liquids containing N-substituted aniline struct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/61C08G73/02
CPCC07D233/61C08G73/0266
Inventor 李君田璐武英黄俐研刘正平
Owner BEIJING NORMAL UNIVERSITY
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