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Sulfonated aromatic dicarboxilic acid and preparation method thereof

A technology for sulfonating aromatic dicarboxylic acid and disulfonic acid, which is applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problem of limited types of sulfonated aromatic diacids, few types of commercial aromatic diacid raw materials, and difficulty in meeting application requirements, etc. problem, to achieve the effect of excellent mechanical properties

Inactive Publication Date: 2009-03-11
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Document Journal of Polymer Science, Part A: Polymer Chemistry 2002, 40, 3703-3710 reported the preparation of a sulfonated aromatic diacid by direct sulfonation reaction using a commercial aromatic diacid (isophthalic acid) as raw material method, but there are very few types of commercial aromatic diacid raw materials, and the types of sulfonated aromatic diacids that can be prepared from these raw materials are very limited, which is difficult to meet the growing application requirements

Method used

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  • Sulfonated aromatic dicarboxilic acid and preparation method thereof
  • Sulfonated aromatic dicarboxilic acid and preparation method thereof
  • Sulfonated aromatic dicarboxilic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 5.59g (30mmol) 2,2'-diphenol, 7.27g (60mmol) 4-fluorobenzonitrile and 16.6g (120mmol) potassium carbonate were added to 100ml of mechanical stirring, nitrogen inlet and reflux condenser In the reactor, add 30ml of N-methylpyrrolidone and react at 180°C for 20 hours. After cooling down to room temperature, the product is poured into water, filtered, and the product is vacuum-dried to obtain 2,2'-bis(4-nitrile 10.48 g of phenoxy)biphenyl, and the yield was 90%.

[0025] 10.48g (27mmol) of 2,2'-bis(4-cyanophenoxy)biphenyl, 7.84g (140mmol) of potassium hydroxide and 190ml of ethylene glycol were added to the reactor and reacted at 180°C for 20 hour, after cooling down to room temperature, the reaction solution was poured into water, added hydrochloric acid to acidic (PH=1), filtered, and the product was vacuum-dried to obtain 2,2'-di(4-carboxyphenoxy)biphenyl 9.77g, producing The rate is 85%.

[0026] Add 9.77g (23mmol) of 2,2'-bis(4-carboxyphenoxy)biphenyl and 135ml of c...

Embodiment 2

[0028] 7.45g (40mmol) 2,2'-diphenol, 9.69g (80mmol) 4-fluorobenzonitrile and 16.6g (120mmol) potassium carbonate were added to 100ml of mechanical stirring, nitrogen inlet and reflux condenser In the reactor, add 60ml of N-methylpyrrolidone and react at 180°C for 24 hours. After cooling down to room temperature, the product is poured into water, filtered, and the product is vacuum-dried to obtain 2,2'-bis(4-nitrile 13.6 g of phenoxy)biphenyl, and the yield was 88%.

[0029] 13.6g (35mmol) of 2,2'-bis(4-cyanophenoxy)biphenyl, 9.8g (175mmol) of potassium hydroxide and 200ml of ethylene glycol were added to the reactor and reacted at 180°C for 20 Hours, after cooling down to room temperature, the reaction solution was poured into water, added hydrochloric acid to acidic (PH=1), filtered, and the product was vacuum-dried to obtain 12.7 g of 2,2'-bis(4-carboxyphenoxy)biphenyl, producing The rate is 85%.

[0030] Add 12.7g (29.8mmol) of 2,2'-bis(4-carboxyphenoxy)biphenyl and 100ml...

Embodiment 3

[0032] 5.59g (30mmol) 4,4'-diphenol, 7.27g (60mmol) 4-fluorobenzonitrile and 16.6g (120mmol) potassium carbonate were added to 100ml of mechanical stirring, nitrogen inlet and reflux condenser In the reactor, add 30ml of N-methylpyrrolidone, react at 180°C for 20 hours, and after cooling down to room temperature, pour the product into water, filter, and dry the product in vacuum to obtain 4,4'-bis(4-nitrile 9.9 g of phenoxy)biphenyl, and the yield was 85%.

[0033]Add 9.9g (25.5mmol) of 4,4'-bis(4-cyanophenoxy)biphenyl, 7.28g (130mmol) of potassium hydroxide and 180ml of ethylene glycol into the reactor and react at 180°C After 20 hours, after cooling down to room temperature, the reaction solution was poured into water, hydrochloric acid was added to make it acidic (PH=1), filtered, and the product was dried in vacuum to obtain 8.9 g of 4,4'-bis(4-carboxyphenoxy)biphenyl, The yield was 82%.

[0034] Add 8.9g (21mmol) of 4,4'-bis(4-carboxyphenoxy)biphenyl and 120ml of concen...

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Abstract

The invention discloses sulfonated aromatic dicarboxylic acid and a preparation method thereof. The sulfonated aromatic dicarboxylic acid is prepared by the following steps: 2, 2'-biphenol or 4, 4'-biphenol and 4-halogen benzonitrile are taken as raw materials to synthesize dicyanoarylene first, the dicyanoarylene is hydrolyzed to produce aromatic diacid, and then the aromatic diacid is sulfonated to obtain the sulfonated aromatic dicarboxylic acid. The sulfonated aromatic dicarboxylic acid can prepare sulfonated polyamide by reacting with diamine, and can prepare sulfonated polybenzimidazole by reacting with tetraarylamine or hexamine. Sulfonated polyamide and sulfonated polybenzimidazole crosslinking membranes have excellent mechanical properties, heat resistance, and solvent resistance, and are widely applied to aspects such as proton conducting membranes and separation membranes for fuel cells, ion exchange membranes for chlor-alkali industry and so on.

Description

technical field [0001] The invention relates to a class of organic compounds and a preparation method thereof, in particular to a sulfonated aromatic dicarboxylic acid and a preparation method thereof. Background technique [0002] In recent years, sulfonated polymers have attracted much attention due to their application prospects in polymer electrolyte fuel cells. Usually sulfonated polymers can be obtained in two ways: one is to sulfonate the polymer directly with a sulfonating agent. Although this method is simple to operate, it is easy to cause low sulfonation and degradation of the polymer chain, and the The degree of sulfonation is not easy to control, so the obtained sulfonated polymer has poor mechanical properties; the second is to polymerize the sulfonated monomer under certain conditions. This method is relatively complicated, but the sulfonation can be controlled by selecting the monomer degree, and obtain polymers with high molecular weight. Sulfonated dicarb...

Claims

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Application Information

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IPC IPC(8): C07C309/42C07C303/06
Inventor 徐宏杰房建华姜建梓印杰
Owner SHANGHAI JIAO TONG UNIV
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