Method for preparing bis(fluorosulfonyl)imide acid and salts thereof

A fluorosulfonyl and imidic acid technology, applied in imine disulfonic acid/nitrilotrisulfonic acid, chemical instruments and methods, nitrosyl chloride, etc., can solve the problem that is not suitable for bis(fluorosulfonyl) Amino acid industrial production, restrictions, medium strong corrosion and heat release, etc.

Pending Publication Date: 2021-11-26
RHODIA OPERATIONS SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Other techniques have been developed, for example, using chlorosulfonyl isocyanate in the presence of oleum and ammonium fluoride (JP 2012-162470) or additionally using urea and fluorosulfonic acid, but these techniques suffer from strong corrosion of the medium and also limited by the exotherm of the reaction
These disadvantages make these techniques less suitable for the industrial production of bis(fluorosulfonyl)imidic acid (HFSI) and its salts

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0037] A solution of sulfamic acid (22.4 g; 230 mmol) in 30 g of o-dichlorobenzene was charged into a 500 ml C276 Hastelloy reactor. Fluorosulfonic acid (1.2 g; 12 mmol) was added and the autoclave was closed. The medium is heated to a temperature of 92°C. Sulfuryl fluoride (47 g; 0.46 mol) was added in such a way as to maintain the pressure below P=37 bar. This addition takes place within 9 hours.

[0038] The temperature was then returned to room temperature and the reactor was depressurized. Analysis of the reaction medium by fluorine 19 NMR showed formation of the expected bis(fluorosulfonyl)imidic acid in 52% yield.

example 2

[0040] A solution of sulfamic acid (22.4 g; 230 mmol) in 300 g of dichloroethane was charged into a 500 ml C276 Hastelloy reactor. Fluorosulfonic acid (1.2 g; 12 mmol) was added and the autoclave was closed. The medium is heated to a temperature of 92°C. Sulfuryl fluoride (47 g; 0.46 mol) was added in such a way as to maintain the pressure below P=37 bar. This addition was performed within 10 hours.

[0041] The temperature was then returned to room temperature and the reactor was depressurized. Analysis of the reaction medium by fluorine 19 NMR showed the formation of the expected bis(fluorosulfonyl)imidic acid in a yield of 53%.

example 3

[0043] Charge 200 g of dichloroethane into a 500 ml C276 Hastelloy reactor, then close the reactor and keep stirring at room temperature and purging with nitrogen. Thionyl fluoride (60 g; 0.34 mol) was then added to the reactor under pressure. A solution of sulfamic acid (22.3 g; 0.23 mol) in dichloroethane (100 g) and then chlorosulfonic acid (26.8 g; 0.23 mol) were added to the autoclave. Then, the temperature was maintained at 80° C. for 17 hours. The observed pressure reached 22 bar at the end of the reaction at this temperature. After returning to room temperature, the reactor was depressurized.

[0044] The medium passes through 19 Analysis by F NMR indicated that the bis(fluorosulfonyl)imidic acid was obtained in 77% yield.

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PUM

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Abstract

The invention relates to a method for preparing bis(fluorosulfonyl)imide acid. The method includes the reaction of sulphamic acid or one of the salts thereof with a halogenosulfuric acid and at least one fluorinating agent selected from SOF2, F-SO2-F and SF4, and the subsequent recovery of bis(fluorosulfonyl)imide acid. The invention also relates to a method for producing salts of bis(fluorosulfonyl)imide from the bis(fluorosulfonyl)imide acid produced.

Description

[0001] This application is a divisional application of the following applications: filing date: December 3, 2014; application number: 2014800733157; invention title: "method for preparing bis(fluorosulfonyl) imidic acid and its salt". 1. Technical field [0002] A subject of the present invention is a process for the preparation of bis(fluorosulfonyl)imide acids (HFSI) and salts thereof, in particular lithium bis(fluorosulfonyl)imide LiFSI. 2. Background technology [0003] The production of HFSI and LiFSI is extensively described in the literature. Among the different techniques described, most utilize fluorination reactions either with HF or with metal fluorides. The use of metal fluorides is problematic because it is often not very effective and uses expensive reagents such as fluorosulfonic acid. For example, fluorination using potassium fluoride in nitromethane or other polar organic solvents is not very efficient in terms of yield (WO 2002 / 053494). Other techniques h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C01B21/093H01M10/0567H01M10/0568C10M125/22C10N30/00
CPCC01B21/0935H01M2300/0025H01M10/0568C01B21/086C01B21/093Y02E60/10
Inventor O·比西纳
Owner RHODIA OPERATIONS SAS
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