Novel benzimidazole ionic monomer and preparation method thereof

A technology of benzimidazole and ionic monomers, which is applied in the field of new benzimidazole ionic monomers and its preparation, and can solve the problems of inability to form ion clusters, limited applications, poor alkali resistance, etc.

Inactive Publication Date: 2018-01-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Quaternary ammonium anion exchange membranes are generally obtained by post-amination of polymer films, but this heterogeneous post-amination reaction makes it impossible to form ion clusters based on hydrophobic-hydrophilic phase separation in the membrane
In addition, the nucleophilic substitution reaction and Hofmann degradation reaction that occur when the quaternary ammonium salt group is attacked by hydroxide under alkaline conditions make the alkali resistance of the quaternary ammonium salt anion exchange membrane poor, which limits its use in Alkaline Fuel Cell Applications

Method used

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  • Novel benzimidazole ionic monomer and preparation method thereof
  • Novel benzimidazole ionic monomer and preparation method thereof
  • Novel benzimidazole ionic monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthetic steps:

[0030] 1) 4-(4-vinylbenzyloxy)benzaldehyde (1a)

[0031] 6.7g (44.0mmol) 4-vinylbenzyl chloride, 4.89g (40.0mmol) 4-hydroxybenzaldehyde, 2.25g (40.0mmol) potassium hydroxide were dissolved in 80mL DMF, reacted at room temperature for 12h, poured into 800mL water, and precipitated White precipitate. Suction filtration, while washing with 200mL water to remove inorganic salts, and dry. Then, the unreacted raw material was removed by quenching with 200 mL of petroleum ether, suction filtered, and vacuum-dried to obtain 8.4 g of a white powder product (yield: 85%).

[0032] 2) 2-(4-(4-vinylbenzyloxy)phenyl)benzimidazole (2a)

[0033] 2.38g (10.0mmol) of 1a, 1.08g (10.0mmol) of o-phenylenediamine and 0.69g (10.0mmol) of ammonium acetate were dissolved in 150mL of absolute ethanol and refluxed at 80°C for 3h. After cooling, the solvent was removed in vacuo, and the obtained solid was separated by column chromatography to obtain 1.9 g of a yellow solid p...

Embodiment 2

[0039] 1) 2,6-Dimethyl-4-(4-vinylbenzyloxy)benzaldehyde (1b)

[0040] 5.04g (33.0mmol) 4-vinylbenzyl chloride, 4.5g (30.0mmol) 2,6-dimethyl-4-hydroxybenzaldehyde, 1.68g (30.0mmol) potassium hydroxide were dissolved in 60mL DMF, and reacted at room temperature After 12 hours, it was poured into 800mL of water, and a beige precipitate was precipitated. Filter with suction while washing with 150 mL of water to remove inorganic salts, and dry. Then, the unreacted raw material was removed by quenching with 150 mL of petroleum ether, suction filtered, and vacuum-dried to obtain 6.1 g of beige crystal product (yield: 86%).

[0041] 2) 2-(2,6-Dimethyl-4-(4-vinylbenzyloxy)phenyl)benzimidazole (2b)

[0042] 2.66g (10.0mmol) of 1b, 1.08g (10.0mmol) of o-phenylenediamine and 0.69g (10.0mmol) of ammonium acetate were dissolved in 150mL of absolute ethanol and refluxed at 80°C for 3h. After cooling, the solvent was removed in vacuo, and the obtained solid was separated by column chromato...

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Abstract

The invention discloses a novel benzimidazole ionic monomer and a preparation method thereof. The structural formula of the monomer is shown in a following image, wherein R is H or a methyl group, andthrough delocalization of charges and a shielding effect of the methyl group in a molecule, the benzimidazole monomer can be stable under an alkaline condition; in addition, the ionic monomer which contains double bonds makes it easier to design polymers with other topological structures so that copolymerization of the monomer and styrene can be achieved, and by adjusting the proportion of the monomer in the copolymerization and regulating the ratio of hydrophilic groups to hydrophobic groups, anion exchange membranes with different performance can be obtained.

Description

technical field [0001] The invention belongs to the field of new materials and organic synthesis, and relates to a novel benzimidazole ion monomer and a preparation method thereof. Background technique [0002] Alkaline anion exchange membrane fuel cells have the advantages of high specific power, high power generation efficiency, and environmental friendliness, while avoiding the disadvantages of high cost and high methanol permeability of proton exchange membrane fuel cells, thus becoming a new energy source that has attracted much attention technology. The alkaline anion exchange membrane is the core component of the alkaline anion exchange membrane fuel cell, which plays the role of isolating the anode and cathode and transmitting hydroxide ions during the operation of the battery. [0003] To date, most anion exchange membranes are based on quaternary ammonium cation polymers. Quaternary ammonium anion exchange membranes are generally obtained by post-amination of pol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C08F12/32C08J5/22H01M8/102H01M8/1069
CPCY02E60/50
Inventor 和庆钢任荣
Owner ZHEJIANG UNIV
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