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Method for producing sulfuric acid fluorinated surfactants

A technology of fluorosurfactant and sulfate ester salt is applied in the field of preparation of sodium 2-ethyl sulfate, and achieves the effects of less waste, high reaction yield and low surface tension

Inactive Publication Date: 2009-04-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few documents related to the preparation method of sulfate ester fluorosurfactants containing perfluoroalkenyl

Method used

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  • Method for producing sulfuric acid fluorinated surfactants
  • Method for producing sulfuric acid fluorinated surfactants

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of embodiment 1N-hydroxyethyl-N-methyl-4-perfluoroalkenyloxybenzenesulfonamide

[0023]In a 500mL four-neck flask, add 225mL chlorobenzene, 124.5g (0.2mol) 4-perfluorononenyloxybenzenesulfonyl chloride (Lianyungang Taizhuo New Material Co., Ltd.), 15.0g (0.2mol) 2-methylaminoethanol , 21.2g (0.2mol) of anhydrous sodium carbonate, stirred, heated to 100°C, and kept stirring at the temperature for 12h. The reaction solution was distilled under reduced pressure until no solvent came out. Cool to room temperature, wash the obtained viscous oil, let it stand, and recrystallize with chlorobenzene to obtain 122.6 g of white crystal N-hydroxyethyl-N-methyl-4-perfluorononenyloxybenzenesulfonamide, the yield 92.7%.

Embodiment 2

[0024] The preparation of embodiment 2N-hydroxyethyl-N-methyl-4-perfluoroalkenyloxybenzenesulfonamide

[0025] React according to the method of Example 1, but the 2-methylaminoethanol feed intake is 75.1g (1.0mol), 21.2g (0.1mol) of anhydrous sodium carbonate is changed to 24g (0.6mol) sodium hydroxide, and the amidation reaction temperature is changed to 120°C, keep the temperature and stir for 24h. The reaction solution was distilled under reduced pressure until no solvent came out. Cool to room temperature, wash the obtained viscous oil, let it stand, and recrystallize with chlorobenzene to obtain 124.7.0 g of white crystal N-hydroxyethyl-N-methyl-4-perfluorononenyloxybenzenesulfonamide. The rate is 94.3%.

Embodiment 3

[0026] The preparation of embodiment 3N-hydroxyethyl-N-methyl-4-perfluoroalkenyloxybenzenesulfonamide

[0027] Carry out reaction according to embodiment 1 method, but solvent is changed into 270mL trichloroethane, 2-methylaminoethanol feed intake is 24.0g (0.32mol), 21.2g (0.1mol) anhydrous sodium carbonate is changed into 40.5g (0.4mol) Triethylamine, the amidation reaction temperature was changed to 80°C, and the temperature was kept stirring for 16h. The reaction solution was distilled under reduced pressure until no solvent came out. Cool to room temperature, wash the obtained viscous oil, let it stand, and recrystallize with chlorobenzene to obtain 123.0 g of white crystal N-hydroxyethyl-N-methyl-4-perfluorononenyloxybenzenesulfonamide, the yield 93.0%.

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Abstract

The invention discloses a preparation method for a sulfuric acid ester salt fluorine surfactant. The method comprises the following steps: taking 4-perfluoro alkene oxygen group benzene sulfonyl chloride and 2-methylamino alcohol as raw materials, taking inorganic base or organic base as an acid-binding agent, and carrying out an amidation reaction in an organic solvent 1 to obtain N- ethoxyl-N-methyl-4-perfluoro alkene oxygen group benzene sulfonyl chloride; and carrying out the esterification reaction of N-ethoxyl-N-methyl-4-perfluoro alkene oxygen group benzene sulfonyl chloride and sulfur trioxide in an organic solvent 2 for 1.5 to 15 hours, carrying out distillation to remove the solvent when the esterification reaction is finished, adding water for dissolution, then adding inorganic base aqueous solution with the mass content of between 10 and 50 percent into the solution till the reaction system is neutral, stirring the reaction system for reaction, and finally obtaining sulphuric acid 2-( N-methyl-4- perfluoro alkene oxygen group benzene sulfonyl chloride)ethyl ester sodium. The preparation method has a convenient raw material source, a simple synthesis method and few wastes. In particular, sulfur trioxide (SO3) and N- ethoxyl-N-methyl-4- perfluoro alkene oxygen group benzene sulfonyl chloride are adopted to carry out the esterification reaction, thereby bringing about high reaction yield.

Description

(1) Technical field [0001] The invention relates to a preparation method of a sulfate ester fluorine surfactant, in particular to a preparation method of sodium 2-(N-methyl-4-perfluoroalkenyloxybenzenesulfonamide) ethyl sulfate. (2) Background technology [0002] Since the 1950s, fluorosurfactants have developed rapidly. In 1974, Mizuno et al. used hexafluoropropylene trimer as raw material to synthesize a series of fluorosurfactants. When the mass concentration was 0.01%, the surface tension of the aqueous solution was about 30mN / m [JP 51011084, 1976]. In 2003, Stébé reported a "star-shaped" nonionic fluorosurfactant with double hydrophilic chains and double lipophilic chains. When the concentration is 0.002% to 0.02%, the surface tension of the aqueous solution can be reduced to about 30mN / m[ Journal of Fluorine Chemistry, 2003, 119(2): 191-205]. In 2006, Nakamura synthesized a multi-branched fluorosurfactant from glycerol oligomers, and the surface tension of its 0.1% a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/02C09K23/02
Inventor 史鸿鑫沈海民项菊萍武宏科
Owner ZHEJIANG UNIV OF TECH
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