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Sulfonated compound containing phosphinyl structure and preparation method thereof

A compound and sulfonation technology, applied in the chemical industry, can solve the problem of less performance characterization, and achieve the effects of comprehensive performance improvement, high proton conductivity, and enhanced interaction force

Inactive Publication Date: 2008-04-30
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Through literature search to prior art, it is found that J.E.McGrath et al published "Synthesis and characterization of sulfonated poly( Arylene ether)s based on functionalized triphenyl phosphine oxide for proton exchange membranes” (preparation and characterization of polyethers containing triphenylphosphine oxide groups for proton exchange membranes), which reported that bis(4-fluorophenyl) phenyl The work of synthesizing bis(4-fluorophenyl)-3'-sodium phenylphosphine oxide by sulfonation of phosphine oxide, and combining it with bis(4-fluorophenyl)phenylphosphine oxide and 4,4'- Sulfonated polyarylphosphine oxides prepared by copolymerization of biphenols, but less work has been done on their property characterization

Method used

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  • Sulfonated compound containing phosphinyl structure and preparation method thereof
  • Sulfonated compound containing phosphinyl structure and preparation method thereof
  • Sulfonated compound containing phosphinyl structure and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Add 5 grams of two (4-halophenyl) phenylphosphine oxides and 7.5 milliliters of 35% fuming sulfuric acid in a 50 milliliter three-neck round bottom flask equipped with mechanical stirring, react at 0 to 60 ° C for 3 hours, then The reaction was carried out at 90 and 110° C. for 2 hours and 8 hours, respectively. After cooling, the reaction solution was poured into a mixture of ice and water, salted out with sodium chloride, and the light red oily substance sank to the bottom, extracted with butanone, and the extract was evaporated to dryness by a rotary evaporator to obtain a crude product, which was dissolved in water. Neutralize with sodium hydroxide and then decolorize with activated carbon, evaporate water by rotary evaporator, use methanol / ethyl acetate as eluent for column separation, and vacuum dry to obtain the target product 3-sodium sulfonate-4-halobenzene Base-3'-sodium sulfonate phenyl-4"-halophenylphosphine oxide, the yield is 80%. The structure of the prod...

Embodiment 2

[0030] Add 3 grams of two (4-halophenyl) phenylphosphine oxides and 4.5 milliliters of 30% fuming sulfuric acid in a 50 milliliter three-necked round bottom flask equipped with mechanical stirring, react at 0 to 60 ° C for 2.5 hours, and then The reaction was carried out at 90 and 110° C. for 1 hour and 9 hours, respectively. After cooling, the reaction solution was poured into a mixture of ice and water, salted out with sodium chloride, and the light red oily substance sank to the bottom, extracted with butanone, and the extract was evaporated to dryness by a rotary evaporator to obtain a crude product, which was dissolved in water. Neutralize with sodium hydroxide and then decolorize with activated carbon, evaporate water by rotary evaporator, use methanol / ethyl acetate as eluent for column separation, and vacuum dry to obtain the target product 3-sodium sulfonate-4-halobenzene Base-3'-sodium sulfonate phenyl-4 "-halophenylphosphine oxide, yield 75%. Product structure obtain...

Embodiment 3

[0032] Add 10 grams of two (4-halophenyl) phenylphosphine oxides and 20 milliliters of 50% fuming sulfuric acid in a 100 milliliter three-necked round bottom flask equipped with mechanical stirring, react at 0 to 90 ° C for 4 hours, and then The reaction was carried out at 110 and 130° C. for 3 hours and 10 hours, respectively. After cooling, the reaction solution was poured into a mixture of ice and water, salted out with sodium chloride, and the light red oily substance sank to the bottom, extracted with butanone, and the extract was evaporated to dryness by a rotary evaporator to obtain a crude product, which was dissolved in water. Neutralize with sodium hydroxide and then decolorize with activated carbon, evaporate water by rotary evaporator, use methanol / ethyl acetate as eluent for column separation, and obtain the target product bis(3-sodium sulfonate-4- Halophenyl)-3'-sulfonate sodium phenylphosphine oxide, yield 70%. The structure of the product was obtained by infra...

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Abstract

The invention discloses sulphonated compound including a phosphine oxide structure, and the preparation method thereof, in particular to 3-sodium sulfonate-4-halogen phenyl-3a-sodium sulfonate phenyl-4a-halogen phenyl phosphine oxide and di (3-sodium sulfonate-4-halogen phenyl)-3a-sodium sulfonate phenyl phosphine oxide and the preparation method thereof. The compound is obtained by taking di (4-halogen phenyl) phenyl phosphine oxide as the raw material through the sulphonation reaction, and the structural formula is shown as follows: the compound can have the nucleophilic aromatic substitution reaction with a bifunctional monomer including two active hydrogens under the alkaline condition, thus sulphonated polymer including a phosphine oxide structural unit is obtained, the performance of the sulphonated polymer is excellent, and the sulphonated polymer yearns for being used for proton exchange membrane materials or other functional materials. X is F, Cl, Br, or I, and Y is H or -SO3Na.

Description

technical field [0001] The invention relates to a compound in the technical field of chemical industry and a preparation method thereof, in particular to a sulfonated compound containing an oxygen phosphine structure and a preparation method thereof. Background technique [0002] Currently, research on proton exchange membranes is very active. Nafion membrane is widely used because of its good comprehensive performance, but it still has serious disadvantages, such as the serious decrease in proton conductivity when the temperature is higher than 100 °C. Proton exchange membrane fuel cells (PEMFC) have many advantages when operating at medium and high temperatures (120-150°C), such as improved electrode reaction kinetics, enhanced CO2 resistance of catalysts, and simplified water and heat management. Therefore, increasing the operating temperature of PEMFC is an important way to improve its performance. SiO2 doping and modifying existing proton exchange membrane materials i...

Claims

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Application Information

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IPC IPC(8): C07F9/53
Inventor 马旭辉张春杰肖谷雨颜德岳
Owner SHANGHAI JIAO TONG UNIV
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