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Quaternary phosphonium salts with p-toluenesulfonate as anions as well as synthesis method, preparation method and application of quaternary phosphonium salts

A technology of p-toluenesulfonate and synthesis method, which is applied in the direction of sulfonate preparation, chemical instruments and methods, and active ingredients of phosphorus compounds, etc. It can solve the problems of high molecular weight, harsh synthesis conditions and routes, and influence on the use effect of quaternary phosphonium compounds. , to achieve the effect of less chemical reagents, high yield and simple steps

Active Publication Date: 2018-07-20
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0038] (3) The molecular weight of the prepared quaternary phosphonium compound is relatively large, which is more suitable for use as an ionic liquid for catalysts, batteries, etc., and these quaternary phosphonium salt fungicides with long-chain molecular structures have very high foam, which affects the use effect ;
[0039] (4) In the methods disclosed in many patents, there are many production steps, the required synthesis conditions and routes are relatively harsh, and some toxic chemical reagents that have obvious impact on the environment are used, and the cost is relatively high.

Method used

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  • Quaternary phosphonium salts with p-toluenesulfonate as anions as well as synthesis method, preparation method and application of quaternary phosphonium salts
  • Quaternary phosphonium salts with p-toluenesulfonate as anions as well as synthesis method, preparation method and application of quaternary phosphonium salts
  • Quaternary phosphonium salts with p-toluenesulfonate as anions as well as synthesis method, preparation method and application of quaternary phosphonium salts

Examples

Experimental program
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Effect test

Embodiment 1

[0096] Embodiment 1: Preparation of diethylene glycol monomethyl ether triphenyl-p-toluenesulfonate

[0097] Dissolve 12.2mmol of diethylene glycol monomethyl ether compound in 15ml of THF, then add 18.3mmol of p-toluenesulfonyl chloride under stirring conditions, and finally add 16.07mmol of p-toluenesulfonyl chloride dropwise slowly within 1 hour under stirring conditions in an ice-water bath. mol of KOH aqueous solution 2.5ml; remove the ice-water bath, return to room temperature and stir for 7 hours; pour the resulting suspension into 10ml of CH 2 Cl 2 and 5ml of ice water, the aqueous layer was washed with CH 2 Cl 2 extraction; then the organic phases were combined and washed three times with distilled water, followed by anhydrous MgSO 4 After drying for 12 hours, filtering and removing the solvent, the crude product was washed three times with petroleum ether, and finally the petroleum ether was removed, and the white liquid product was obtained by vacuum drying, whic...

Embodiment 2

[0099] Embodiment 2: Preparation of polyethylene glycol monomethyl ether (Mw=350) triphenyl-p-toluenesulfonate

[0100] Dissolve 20 mmol of polyethylene glycol monomethyl ether (Mw = 350) in 20 ml of anhydrous CH 2 Cl 2 and added 6.7ml of triethylamine, then slowly added p-toluenesulfonyl chloride TsCl (22mmol of TsCl dissolved in 30ml of anhydrous CH 2 Cl 2 ) solution and drop it off within 1 hour. After removing the ice-water bath and returning to room temperature, stirring was continued for 24 hours. The resulting mixture was washed three times with 1 mol of HCL solution, 30 ml each time, and then the organic layer was washed with anhydrous NaHCO 3 Dry, filter and concentrate. Finally, the crude product was washed three times with petroleum ether, 30 ml each time; the solvent was evaporated and concentrated to obtain a light yellow oily compound, which was polyethylene glycol monomethyl ether (Mw=350) p-toluenesulfonate.

[0101] Dissolve 5mmol of polyethylene glycol ...

Embodiment 3

[0102] Embodiment 3: Preparation of polyethylene glycol monomethyl ether (Mw=750) triphenylphosphine p-toluenesulfonate

[0103] Dissolve 20 mmol of polyethylene glycol monomethyl ether (Mw=750) in 20 ml of anhydrous CH 2 Cl 2 and added triethylamine (6.7ml), then slowly added p-toluenesulfonyl chloride TsCl (4.2g, 22mmol TsCl dissolved in 30ml anhydrous CH 2 Cl 2 ) solution and drop it off within 1 hour. After removing the ice-water bath and returning to room temperature, stirring was continued for 24 hours. The resulting mixture was washed three times with 1 mol of HCl solution, 30 ml each time, and then the organic layer was washed with anhydrous NaHCO 3 Dry, filter and concentrate; finally, the crude product is washed three times with petroleum ether, 30ml each time; the solvent is removed by evaporation and concentration to obtain a light yellow oily compound, which is polyethylene glycol monomethyl ether (Mw=750) p-toluenesulfonate .

[0104] Dissolve 5mmol of poly...

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Abstract

The invention discloses quaternary phosphonium salts with p-toluenesulfonate as anions as well as a synthesis method, a preparation method and an application of the quaternary phosphonium salts. The synthesis method adopts a simple two-step synthesis route, that is, diethylene glycol monomethyl ether / methoxypolyethylene glycols reacts with p-methyl benzene sulfonic chloride to prepare diethylene glycol monomethyl ether / methoxypolyethylene glycol p-toluenesulfonate, then, diethylene glycol monomethyl ether / methoxypolyethylene glycol p-toluenesulfonate further reacts with triphenylphosphonium toobtain diethylene glycol monomethyl ether / methoxypolyethylene glycol-triphenyl phosphine p-toluenesulfonate. Through the simple synthesis route, the product has good dissolution property and cell penetrability, better antibacterial and killing performance for microbes and an anti-tumor function.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a class of quaternary phosphonium salts. Background technique [0002] Since Messinger et al. synthesized tetrahydroxymethylphosphonium salt in 1888, quaternary phosphonium salt and its derivatives have been developed rapidly. Compared with quaternary ammonium salt cationic surfactants, quaternary phosphonium salt cationic surfactants, as a new class of cationic surfactants, have the characteristics of low foam, fast penetration, wide pH adaptability, and strong stripping ability. Since the 1990s, the development of quaternary phosphonium salts has entered a brilliant and mature period. It is during this period that new products are born and the application fields continue to expand. So far, more than 1,000 kinds of quaternary phosphonium salts have been synthesized. Quaternary phosphonium salts have the advantages of high efficiency, broad-spectrum bactericidal properties, low do...

Claims

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Application Information

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IPC IPC(8): C07F9/54C07C309/30C07C303/32A61K31/66A61P35/00A61P31/04
CPCC07C309/30C07F9/5442
Inventor 敖宁建吴海伟顾留群林越威李洲
Owner JINAN UNIVERSITY
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