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Wholly aromatic side-chain-type sulfonated dichloro monomer and preparation method thereof

A technology for sulfonating dichloride and dichloride monomers, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as the limitation of sulfonic acid group activity, and achieve the effect of improving proton conductivity

Inactive Publication Date: 2014-06-25
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The microphase separation structure formed by this sulfonated polyarylethersulfone membrane has excellent water resistance and stability, but because the sulfonic acid group is attached to the main chain of the molecule, the activity of the sulfonic acid group is limited

Method used

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  • Wholly aromatic side-chain-type sulfonated dichloro monomer and preparation method thereof
  • Wholly aromatic side-chain-type sulfonated dichloro monomer and preparation method thereof
  • Wholly aromatic side-chain-type sulfonated dichloro monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A fully aromatic side chain type sulfonated dichloro monomer, the structural formula and reaction formula are as follows:

[0029]

[0030] Preparation of 2,2'-benzophenone-4,4'-dichlorodiphenylsulfone:

[0031] Under the condition of nitrogen protection and magnetic stirring, 11.5g (40mmol) of 4,4'-dichlorodiphenyl sulfone and 200mL tetrahydrofuran solvent were added to a dry 500mL reaction flask, and the temperature of the system was lowered to Below -60°C, add 33mL (84mmol) of n-butyllithium solution dropwise to the reaction system, and keep the temperature not higher than -55°C, react for 2 hours after the dropwise addition, then add 11.45g (84mmol) of dry zinc chloride, React at low temperature below -60°C for 2 hours, add 16.0g (84mmol) of cuprous iodide, gradually increase the temperature from -60°C to -30°C for 1 hour, finally add 11.8g (84mmol) of benzoyl chloride, and control the temperature at React below -10°C for more than 5 hours. After the reaction, w...

Embodiment 2

[0039] A fully aromatic side chain type sulfonated dichloro monomer, the structural formula and reaction formula are as follows:

[0040]

[0041] Preparation of 2,2'-benzophenone-4,4'-dichlorodiphenylsulfone:

[0042]Under the condition of nitrogen protection and magnetic stirring, 11.5g (40mmol) of 4,4'-dichlorodiphenyl sulfone and 200mL tetrahydrofuran solvent were added to a dry 500mL reaction flask, and the temperature of the system was lowered to Below -60°C, add 33mL (84mmol) of n-butyllithium solution dropwise to the reaction system, and keep the temperature not higher than -55°C, react for 2 hours after the dropwise addition, then add 11.45g (84mmol) of dry zinc chloride, React at low temperature below -60°C for 2 hours, add 7.52g (84mmol) of cuprous nitrile, and gradually raise the temperature from -60°C to -30°C for 1 hour, finally add 11.8g (84mmol) of benzoyl chloride, and control the temperature at React below -10°C for more than 5 hours. After the reaction, ...

Embodiment 3

[0046] A fully aromatic side chain type sulfonated dichloro monomer, the structural formula and reaction formula are as follows:

[0047]

[0048] Preparation of 2,2'-di-p-phenoxybenzophenone-4,4'-dichlorodiphenylsulfone:

[0049] Under nitrogen protection and magnetic stirring conditions, add 11.5g (40mmol) of 4,4'-dichlorodiphenyl sulfone and 240mL tetrahydrofuran solvent to a dry 500mL reaction flask, and use a liquid nitrogen-acetone low temperature bath to reduce the system temperature to Below -60°C, add 33mL (84mmol) of n-butyllithium solution dropwise to the reaction system, and keep the temperature not higher than -55°C, react for 2 hours after the dropwise addition, then add 11.45g (84mmol) of dry zinc chloride, React at a low temperature below -60°C for 2 hours, add 16.0g (84mmol) of cuprous iodide, gradually increase the temperature from -60°C to -30°C for 1 hour, and finally add 19.5g (84mmol) of 4-phenoxybenzyl Acyl chloride, the temperature is controlled bel...

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Abstract

The invention relates to a wholly aromatic side-chain-type sulfonated dichloro monomer and a preparation method thereof, belonging to the technical field of chemical engineering macromolecules. The preparation method comprises the steps: with 4,4'-dichloro sulfobenzide as a raw material, reacting the 4,4'-dichloro sulfobenzide with a metallo-organic compound to generate a metallo-organic compound intermediate, and reacting the metallo-organic compound intermediate with acyl chloride compounds of different structures to prepare a series of wholly aromatic side-chain-type dichloro monomers, and performing a sulfonation reaction of fuming sulphuric acid or chlorosulfonic acid to prepare a series of wholly aromatic side-chain-type sulfonated dichloro monomers. Sulfonic acid groups in aromatic sulfonated dichloro monomer molecules are connected to a side group; because the sulfonic acid group and a main chain are separated by an aromatic side group, a sulfonated polymer prepared by the aromatic sulfonated dichloro monomers is expected to enable the main chain of the sulfonated polymer to be more stable and easily form a microphase separation structure, thus the proton conduction rate is increased. The wholly aromatic side-chain-type sulfonated dichloro monomer is wide in application prospect in the aspects of proton conducting membranes for fuel cells, separating membranes, ion exchange membranes for the chlor-alkali industry.

Description

technical field [0001] The invention relates to a fully aromatic side chain type sulfonated dichloro monomer and a preparation method thereof, belonging to the technical field of chemical polymers. Background technique [0002] In recent years, the application prospects of sulfonated polymers in proton exchange membrane fuel cells have attracted much attention. Among them, sulfonated polyarylethersulfone is famous for its excellent film-forming properties, excellent mechanical properties, heat resistance and solvent resistance. It has become the most promising class of materials for practical applications. Sulfonated polyarylethersulfone membrane is a kind of proton exchange membrane material with good performance, which has the advantages of high electrical conductivity, good thermal stability and chemical stability. However, the electrical conductivity is heavily dependent on the degree of sulfonation of the polymer. When the degree of sulfonation increases, both the wate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07C315/04
Inventor 陈康成韩丁波赵之平刘文芳
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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