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Preparation method and application of potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate

The technology of pentafluoroethyl and cyclohexyl is applied in the field of preparation and application of potassium decafluoro-4-cyclohexyl-1-sulfonate, and can solve the problem that the yield is only 25% and the cyclic perfluoroalkanesulfonic acid is only 25%. Problems such as loss of access to potassium

Active Publication Date: 2020-05-15
PERIC SPECIAL GASES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as the Stockholm Treaty listed PFOS as 9 chemicals that are no longer produced, its by-products, various cyclic potassium perfluoroalkane sulfonates, lost access and were strictly restricted in other industries, but in the field of aviation hydraulic oil allowed to use
US 3M company patent US2732398 reports the use of p-ethylbenzenesulfonyl chloride in anhydrous hydrogen fluoride electrolyzer to prepare potassium perfluoroalkylsulfonate by electrochemical fluorination, but the yield is only 25%.

Method used

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  • Preparation method and application of potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate
  • Preparation method and application of potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate
  • Preparation method and application of potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate

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Experimental program
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Effect test

Embodiment 1

[0025] (1) React p-ethylbenzenesulfonyl chloride and potassium fluoride in acetonitrile. Control the reaction temperature at (80±5)°C. After 8 hours of reaction, the reaction system will naturally return to room temperature. First filter to remove solid impurities, and then carry out distillation collection p-ethylbenzenesulfonyl fluoride;

[0026] (2) The p-ethylbenzenesulfonyl fluoride collected in step (1) is added in the anhydrous hydrogen fluoride electrolyzer, and n-butanethiol is added in the electrolytic solution (hydrogen fluoride and potassium fluoride) and n-butanethiol is electrolyzed The mass fraction in the liquid is 0.5%, the temperature of the electrolyte is controlled at 0°C, a voltage of 5.5V is applied to the electrode for electrolysis, and the electrolysis is carried out for 8 hours. The electrolysis product is collected by liquid separation to obtain decafluoro-4-(perfluoroethyl) ring Crude hexyl-1-sulfonyl fluoride;

[0027] (3) The crude product of deca...

Embodiment 2

[0032] (1) React p-ethylbenzenesulfonyl chloride and cesium fluoride in dimethyl sulfoxide. Control the reaction temperature at (60±5)°C. After 8 hours of reaction, the reaction system will naturally return to room temperature, and first filter to remove solid impurities. Carry out distillation again and collect p-ethylbenzenesulfonyl fluoride;

[0033] (2) The p-ethylbenzenesulfonyl fluoride collected in step (1) is added in the anhydrous hydrogen fluoride electrolyzer, and n-butanethiol is added in the electrolytic solution (hydrogen fluoride and potassium fluoride) and n-butanethiol is electrolyzed The mass fraction in the solution is 0.6%, the temperature of the electrolyte is controlled at 5°C, and a voltage of 5V is applied to the electrode for electrolysis. After electrolysis for 12 hours, the electrolysis product is collected by liquid separation to obtain decafluoro-4-(perfluoroethyl)cyclohexyl - Crude 1-sulfonyl fluoride;

[0034] (3) The crude product of decafluoro...

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Abstract

The invention relates to a preparation method and an application of potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate, and belongs to the technical field of fine fluorine chemical engineering. P-ethylbenzenesulfonyl chloride used as a raw material is converted into p-ethylbenzenesulfonyl fluoride, electrolytic fluorination is performed in the presence of n-butyl mercaptan, the electrolysis yield reaches 50% or higher, decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonyl fluoride obtained through electrolysis is rectified and then hydrolyzed by an aqueous KOH solution to obtain the potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate with the purity being greater than 98%, and the prepared potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate has a very good application prospect in aviation hydraulic oil.

Description

technical field [0001] The invention relates to the preparation and application of potassium decafluoro-4-(pentafluoroethyl)cyclohexyl-1-sulfonate, which belongs to the technical field of fine fluorine chemical industry. Background technique [0002] Perfluoroalkylsulfonyl fluoride is a general term for perfluoroalkylsulfonyl compounds, and its general formula is: R f SO 2 F(R f = CF 3 , C 2 f 5 , C 3 f 7 ...). Due to the introduction of fluorine atoms, perfluoroalkyl compounds exhibit extremely low surface energy, high chemical stability and water and oil repellency, and have high thermal stability. Perfluoroalkylsulfonyl fluoride also has a reactive group (-SO 2 F), can be used as an intermediate in many organic reactions to prepare various fluorine-containing materials. [0003] During the preparation of perfluorooctane sulfonyl fluoride by electrochemical fluorination, the yield of perfluorooctane sulfonyl fluoride is only 43% to 50%, and other by-products incl...

Claims

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Application Information

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IPC IPC(8): C07C309/25C07C303/32C25B3/08C10M135/10C10N40/08C10N10/02C25B3/28
CPCC07C303/32C07C303/44C07C303/02C10M135/10C07C2601/14C10M2219/044C25B3/28C07C309/25C07C309/85C07C309/86
Inventor 耿谦马毅斌张雷户帅帅徐海云郭绪涛王斌罗文键
Owner PERIC SPECIAL GASES CO LTD
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