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Novel fluorine-containing polybenzimidazole polymer, fluorinated organic diacid monomer as intermediate of the fluorine-containing polybenzimidazole polymer, and their preparation method

A technology of polybenzimidazole and benzimidazole, which is applied in the field of preparation of functional polymer materials, can solve problems that need to be further improved, strong intermolecular force, membrane oxidation degradation, etc., and is suitable for large-scale production and excellent oxidation resistance The effect of performance and easy availability of raw materials

Active Publication Date: 2014-09-17
TSINGHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the operation of hydrogen-air PEMFC cells, the oxidation stability of the membrane must be considered, which is due to the H produced during the reaction of the PEMFC cathode electrode. 2 o 2 And -OH or / and -OOH free radicals will erode the molecular chains in the membrane, resulting in oxidative degradation of the membrane
Since the main chain of polybenzimidazole is carbon-carbon bond and carbon-hydrogen bond, its oxidation resistance stability needs to be further improved compared with perfluorosulfonic acid membrane
At the same time, traditional polybenzimidazole materials have poor solubility due to their rigid molecular chain structure and strong intermolecular forces.

Method used

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  • Novel fluorine-containing polybenzimidazole polymer, fluorinated organic diacid monomer as intermediate of the fluorine-containing polybenzimidazole polymer, and their preparation method
  • Novel fluorine-containing polybenzimidazole polymer, fluorinated organic diacid monomer as intermediate of the fluorine-containing polybenzimidazole polymer, and their preparation method
  • Novel fluorine-containing polybenzimidazole polymer, fluorinated organic diacid monomer as intermediate of the fluorine-containing polybenzimidazole polymer, and their preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1) Preparation of fluorinated organic diacid monomer

[0052] in N 2 Add 172g of 2,3-difluoro-4 methylbenzoic acid, 25g of hydrazine hydrate, and 750g of polyphosphoric acid into the three-necked flask under protection (the molar ratio of the three is 2:1:15), start stirring, and slowly heat to 60°C for reaction. After 3 hours, the temperature was raised to 120°C for 8 hours. The reaction mixture was poured into 5 L of water, and the white precipitate was collected by filtration. The precipitate was neutralized with 1% NaOH aqueous solution, washed with water until neutral, and dried in vacuum to obtain 182 g of white intermediate 2. 5-bis(2,3-difluoro-4methylphenyl)oxadiazole. Take 32.2g (0.1mol) of this intermediate and add it to a 2L three-necked flask, then add 40g of water and 100g of pyridine, heat to reflux, slowly add potassium permanganate in portions, add 47.4g (0.3mol), and reflux for 100h. The mixture was poured into 10% hydrochloric acid with excess mass ...

Embodiment 2

[0058] 1) Preparation of fluorinated organic diacid monomer

[0059] in N 2 Add 114g of 2,3,5,6-tetrafluoro-4-methylbenzoic acid, 12.5g of hydrazine monohydrate, and 380g of polyphosphoric acid into the three-necked flask under protection (the molar ratio of the three is 2.2:1:15), and open Stir, slowly heat to 80 ° C for 3 h, heat up to 200 ° C for 24 h, pour the reaction mixture into 3 L of water, filter and collect the white precipitate, and dissolve the resulting precipitate with a mass concentration of 1% Na 2 CO 3 After the aqueous solution was neutralized, it was washed with water until neutral, and dried in vacuum to obtain 116 g of white intermediate 2,5-bis(2,3,5,6-tetrafluoro-4methylphenyl)oxadiazole. Add 39.4g (0.1mol) of the obtained intermediate into a 2L three-necked flask, then add 100g of water and 100g of pyridine, heat to reflux, slowly add potassium permanganate in portions, add 63g (0.4mol), and react under reflux for 20h. The substance was poured into ...

Embodiment 3

[0065] 1) Preparation of fluorinated organic diacid monomer

[0066] Add 218g of 2,3,4,6-tetrafluoro-5-methylbenzoic acid, 25g of hydrazine monohydrate, and 260g of polyphosphoric acid into the there-necked flask under the protection of argon (the molar ratio of the three is 2.1:1:5) , start stirring, slowly heat up to 80°C for 4h, heat up to 200°C for 16h, pour the reaction mixture into 3L of water, collect the precipitate by filtration, and remove the resulting precipitate with a mass concentration of 1% Na 2 CO 3 The aqueous solution was neutralized, washed with water until neutral, and dried in vacuum to obtain 197 g of white intermediate (2,3,4,6-tetrafluoro-5-methylphenyl)oxadiazole. Take 39.4g (0.1mol) of this intermediate and add it to a 2L three-necked flask, then add 120g of water and 60g of pyridine, heat to reflux, slowly add potassium permanganate in portions, add 158g (1.0mol), and react under reflux for 2h. Poured into excess mass concentration of 10% hydrochl...

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Abstract

The invention discloses a fluorine-containing polybenzimidazole polymer, a fluorinated organic diacid monomer as an intermediate of the fluorine-containing polybenzimidazole polymer, and their preparation method. The novel fluorine-containing polybenzimidazole polymer is shown in a structural formula 4. The fluorinated organic diacid is shown in a structural formula 3. The preparation method comprises the following steps that methyl-substituted fluorine-containing benzoic acid and hydrazine hydrate undergo a condensation reaction in polyphosphoric acid to produce fluorinated oxadiazolene xylene; the fluorinated oxadiazolene xylene as an intermediate is oxidized into a fluorinated organic diacid monomer by potassium permanganate or nitric acid; and the fluorinated organic diacid monomer, a composite diacid monomer and a tetramine monomer undergo a polycondensation reaction in polyphosphoric acid to produce the novel fluorine-containing polybenzimidazole polymer. The fluorine-containing polybenzimidazole polymer has good solubility and oxidation-resistant stability and can be used as a high-temperature proton exchange membrane, a separating membrane, a sensor, a high temperature-resistant fiber, a composite material, a binder and other function material for a fuel cell.

Description

technical field [0001] The invention belongs to the technical field of preparation of functional polymer materials, and in particular relates to a fluorine-containing polybenzimidazole polymer and its intermediate fluorinated organic diacid, as well as their preparation method and application. Background technique [0002] As a new generation of power generation technology, fuel cell has attracted more and more attention due to its green and high-efficiency characteristics. The proton exchange membrane fuel cell (PEMFC) with polymer proton exchange membrane as the electrolyte is an outstanding representative of fuel cells. Its advantages are simple structure, high energy efficiency, environmental friendliness and zero emission, and low temperature and fast start. , Distributed small power supply stations and other aspects have shown broad application prospects, and governments and large companies of all countries have invested heavily in research and development. The core m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/107C08G73/18C08L79/04C08J5/18C08J7/00H01M8/10
CPCY02E60/521Y02E60/50Y02P70/50
Inventor 尚玉明王树博王金海王要武谢晓峰李存璞
Owner TSINGHUA UNIV
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