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Preparation method of perfluorovinyl ether sulfonyl fluoride

A technology of perfluorovinyl ether and sulfonyl fluoride, which is applied in the preparation of sulfonic acid, organic chemistry and other directions, can solve the problems such as the reaction process is not mild enough, loss and by-product influence, high fluorine waste liquid waste gas and other problems, and reduce the reaction steps. , The post-processing is simple and the effect of avoiding waste acid gas

Active Publication Date: 2018-11-23
SHANDONG DONGYUE WEILAI HYDROGEN ENERGY MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sulfonate undergoes a two-step reaction to obtain the final product. During the chlorination process, hydrogen chloride and hydrogen fluoride waste gas are generated, which strongly corrodes the reactor, and phosphoric acid waste liquid is generated after post-treatment. The loss of the reaction process and the impact of by-products reduce the yield.
[0004] The preparation method of perfluoroalkene ether sulfonyl fluoride directly prepared by using perfluoroalkene ether sulfonate as raw material, Daikin company patent US7005545 proposes to use hydrogen fluoride as solvent and sulfur tetrafluoride as fluorinating agent to obtain a medium yield product, but The reagents used in this reaction are highly toxic and corrosive, and the reaction process is not gentle enough, requiring high temperature and high pressure reaction, and the post-treatment is complicated, resulting in excessive high-fluorine waste liquid and waste gas

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] CF 2 = CFOCF 2 CFCF 3 OCF 2 CF 2 SO 2 Preparation of F:

[0023] In a 2L three-necked flask, add 800 mL of tetraethylene glycol dimethyl ether, and then add CF under stirring 2 = CFOCF 2 CFCF 3 OCF 2 CF 2 SO 3 Na 460g, slowly drop the fluorinating reagent CHClFCF at room temperature 2 N(C 2 h 5 ) 2 201g, the dropwise addition time was controlled within 1 hour. After the dropwise addition, the temperature was continued to rise to 80°C for 3 hours. After the reaction was completed, 370g of fractions below 160°C were distilled, with a yield of 83% and a purity of 95.3%.

Embodiment 2

[0025] CF 2 = CFOCF 2 CFCF 3 OCF 2 CF 2 SO 2 Preparation of F:

[0026] In a 5L three-necked flask, add 3000mL of methanol, CF 2 = CFOCF 2 CFCF 3 OCF 2CF 2 SO 3 Dissolve Na 200g in methanol solution, then add 800g gel-type cationic resin (IEC=1.19mmol / g), stir for more than 12 hours, and reclaim the methanol solvent from the solution obtained by suction filtration, then continue to wash the resin, continue to concentrate the suction filtrate, wash The number of times is more than 3 times, and then the concentrates are combined to obtain 177g of the corresponding sulfonic acid, and the crude yield is 93%.

[0027] In a 2L three-necked flask, add 800 mL of tetraethylene glycol dimethyl ether, and then add the above CF under stirring 2 = CFOCF 2 CFCF 3 OCF 2 CF 2 SO 3 H 175g, slowly drop the fluorinating reagent CHClFCF at room temperature 2 N(C 2 h 5 ) 2 83g, the dropwise addition time was controlled within 1 hour. After the dropwise addition, the temperatu...

Embodiment 3

[0029] CF 2 = CFOCF 2 CFCF 3 OCF 2 CF 2 SO 2 Preparation of F:

[0030] In a 2L three-necked flask, add 800 mL of tetraethylene glycol dimethyl ether, and then add CF under stirring 2 = CFOCF 2 CFCF 3 OCF 2 CF 2 SO 3 Na 460g, slowly add fluorinated reagent CF dropwise at room temperature 3 CHFCF 2 N(C 2 h 5 ) 2 290g, the dropping time was controlled within 1 hour, and after the dropping was completed, the temperature was continued to rise to 80°C for 3 hours. After the reaction was completed, 346g of fractions below 160°C were distilled, with a yield of 83% and a purity of 96.2%.

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Abstract

The invention belongs to the technical field of perfluorinated resin, and particularly relates to a preparation method of Perfluorovinyl ether sulfonyl fluoride. A CF2=CF(OCF2CFX)mO(CF2)nSO2F productis directly generated from perfluorovinyl ether sulfonate CF2=CF(OCF2CFX)mO(CF2)nSO2OM by a one-step reaction under the action of a fluorinating reagent CHClFCF2N(C2H5)2,CF3CHFCF2N(C2H5)2. The preparation method has the advantages of simple process, easiness in operation, low reagent cost, avoidance of the production of waste acid gas and waste liquid as well as the increase of multi-step wastageand by-products; reaction steps are reduced, and the use of high-toxicity and high-risk reagents is avoided at the same time, and the yield can be up to 80 percent or more.

Description

technical field [0001] The invention belongs to the technical field of perfluororesin, and in particular relates to a preparation method of perfluorovinyl ether sulfonyl fluoride. Background technique [0002] Perfluorosulfonic acid ionomers have been used in the chlor-alkali industry and proton exchange membrane fuel cells since the 1970s. After decades of application and promotion, the technology has become more mature, and it has been widely used in many fields of the chemical industry. The use of perfluorosulfonic acid ion exchange membranes in electrolyzers and fuel cells is a known technology. Although many polymers can be prepared into ion exchange membranes, they are suitable as membrane materials for chlor-alkali ion membranes and fuel cell proton exchange membranes, and ion exchange membranes with ion exchange groups such as sulfonic acid groups and perfluorinated structures are more suitable. In the prior art, the preparation of perfluoroionic polymers containing...

Claims

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Application Information

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IPC IPC(8): C07C303/02C07C309/82
CPCC07C303/02C07C309/82
Inventor 史大阔张永明牛晓刚魏刚张帅
Owner SHANDONG DONGYUE WEILAI HYDROGEN ENERGY MATERIAL CO LTD
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