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Dicarboxy diphenylsulfone containing sulphonate group and preparation thereof

A technology containing sulfonate and diphenyl sulfone, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problem of fewer types of dicarboxylic monomers, and achieve improved proton conductivity and oxidation resistance Effect

Inactive Publication Date: 2012-10-10
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are few types of dicarboxylic monomers containing sulfonate groups, which are difficult to meet the needs of applications. Therefore, it is necessary to continuously research and develop dicarboxylic monomers containing sulfonate groups with various structures in order to prepare polymers with excellent properties.

Method used

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  • Dicarboxy diphenylsulfone containing sulphonate group and preparation thereof
  • Dicarboxy diphenylsulfone containing sulphonate group and preparation thereof
  • Dicarboxy diphenylsulfone containing sulphonate group and preparation thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Synthesis of 4'-sodium sulfonate-2,5-dimethylbenzene sulfide: Add 5 grams (0.03617mol) of 2,5-dimethylbenzene in a dry flask equipped with a stirrer, air guide tube and condensation water trap Thiophenol, 7.5255 grams (0.03798mol) of sodium p-fluorobenzenesulfonate, 3.6242 grams (0.05245mol) of anhydrous potassium carbonate, 50mL of N-methylpyrrolidone and 50mL of toluene were stirred at room temperature and dissolved completely. Then heat to 140°C, reflux for 4 hours to dehydrate, and completely distill the toluene; then raise the temperature to 190°C, and continue the reaction for 24 hours. After the reaction was completed, cool to room temperature, and the precipitate was suction-filtered to obtain a filter cake, which was dissolved in water and salted out with sodium chloride to obtain 9.73g of 4'-sodium sulfonate-2,5-dimethylphenylsulfide , yield 85%.

Embodiment 2

[0037] Synthesis of 4'-sodium sulfonate-2,5-dimethylbenzene sulfide: Add 10 grams (0.07234mol) of 2,5-dimethylbenzene to a dry flask equipped with a stirrer, air guide tube and condensation trap Thiophenol, 15.051 g (0.07596 mol) of sodium p-fluorobenzenesulfonate, 7.2484 g (0.1049 mol) of anhydrous potassium carbonate, 150 mL of N, N-dimethylformamide and 150 mL of toluene were stirred at room temperature to dissolve completely. Then heat to 140°C, reflux for 4 hours to dehydrate, and completely distill the toluene; then raise the temperature to 170°C, and continue the reaction for 48 hours. After the reaction was completed, cool to room temperature, and the precipitate was suction-filtered to obtain a filter cake, which was dissolved in water and salted out with sodium chloride to obtain 20.14g of 4'-sodium sulfonate-2,5-dimethylphenylsulfide , yield 88%.

[0038] The specific characterization results are as follows:

[0039] figure 1 is 4'-sodium sulfonate-2,5-dimethylph...

Embodiment 3

[0042] Add 5 grams of 4'-sodium sulfonate-2,5-dimethylphenylene sulfide and 0.3 grams of sodium hydroxide into a three-necked flask equipped with a stirring device containing 150 mL of water, and raise the temperature to 70 ° C while stirring, Add a total of 15 grams of potassium permanganate in batches, react for 8 hours, filter the reaction mixture while it is hot, acidify the filtrate with hydrochloric acid, precipitate white crystals, filter with suction, and recrystallize the filter cake with water to obtain 5.8 grams of 4'-sodium sulfonate -2,5-dicarboxyphenyl sulfone, the yield is 90%.

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Abstract

The invention discloses a dicarboxyl diphenyl sulfone containing sulfonate group belonging to the technical field of chemical industry and a preparation method thereof. Sulfonated polybenzimidazole, sulfonated polybenzoxazole and sulfonated polybenzothiazole can be prepared by directly copolymerizing the dicarboxyl diphenyl sulfone containing sulfonate group and dicarboxyl monomer respectively with tetramines aromatic monomer, tetramines aromatic group dihydroxyl monomer or tetramines aromatic group dimercapto monomer, therefore, sulfonic acid groups are positioned on side group benzene ringsof polymers; besides, the solubility property, proton conductivity and antioxidation of sulfonated products are greatly improved and the compound can be applied to the field of proton exchange membranes. The general formula of the dicarboxyl diphenyl sulfone containing sulfonate group of the invention is shown as follows, wherein, M indicates lithium, sodium, potassium, rubidium or cesium ion.

Description

technical field [0001] The invention relates to a dicarboxydiphenyl sulfone in the technical field of chemical industry and a preparation method thereof, in particular to a sulfonate group-containing dicarboxydiphenyl sulfone and a preparation method thereof. Background technique [0002] Polybenzimidazole, polybenzoxazole and polybenzothiazole are a large class of high-performance aromatic heterocyclic polymers with good mechanical properties, high thermal stability and good chemical stability, and are considered to be excellent proton exchange membranes. Matrix material. Polybenzimidazole-based proton exchange membrane materials have been extensively researched and applied in the field of fuel cells. Sulfonated polybenzimidazole, sulfonated polybenzoxazole and sulfonated polybenzothiazole can be combined with aromatic tetramine monomer, aromatic diamine group and dicarboxylic monomer containing sulfonate group respectively. Prepared by copolymerization of dihydroxy monom...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/44C07C315/02
Inventor 谭宁肖谷雨颜德岳
Owner SHANGHAI JIAOTONG UNIV