Process for fluorination of sulphonyl halide compounds

Abstract

The present disclosure relates to the preparation of a compound of formula (I) comprising an —SO 2 F function, R—SO 2 F, by reacting a compound of formula (II), R′—SO 2 X, with a fluorinating agent, the process carried out in the liquid phase in the presence of hydrofluoric acid using an antimony-based fluorination catalyst, wherein R, R′, and X are described herein.

What is claimed is: 
     
         1 . A non-electrochemical process for preparing a fluorinated compound of formula (I) comprising at least one —SO 2 F function, wherein the compound of formula (I) is prepared by reacting a compound of formula (II) with at least one fluorinating agent, wherein the process is carried out in the liquid phase in the presence of hydrofluoric acid using an antimony-based fluorination catalyst:
   R—SO 2 F   (I)
 
 where R is selected from the group consisting of R1, R2 and R3: 
 R1=—C n H a F b  with n=1-10, a+b=2n+1, b≧1; 
 R2=—C x H y F z —SO 2 F with x=1-10, y+z=2x and z≧1; 
 R3=Φ-C c H h F f  with c=1-10; h+f=2c and f≧1; Φ denoting a phenyl group;
   R′—SO 2 X   (II)
 
 
 where R′ is selected from the group consisting of R′1, R′2 and R′3: 
 R′1=—C n H a X b  with n=1-10, a+b=2n+1, b≧1; 
 R′2=—C x H y X z —SO 2 X with x=1-10, y+z=2x and z≧1; 
 R′3=Φ-C c H h X f  with c=1-10; h+f=2c and f≧1; Φ denoting a phenyl group; 
 X is a halogen atom selected from the group consisting of chlorine and bromine. 
 
     
     
         2 . The preparation process as claimed in  claim 1 , wherein the radicals R1 and R′1 are perhalogenated so that b=3 and a=0. 
     
     
         3 . The preparation process as claimed in  claim 1 , wherein the radical R of the compound (I) is the radical R1 wherein n=1, a=0 and b=3, or n=1, a=1, b=2 or else n=1, a=2 and b=1. 
     
     
         4 . The preparation process as claimed in  claim 1 , wherein the compound of formula (II) is obtained by radical halogenation of a compound of formula R′ H —SO 2 X (formula III), where R′ H  is selected from the group consisting of R′ H 1, R′ H 2 and R′ H 3:
 R′ H 1=—C n H 2n+1  with n=1-10; 
 R′ H 2=—C x H 2x —SO 2 X with x=1-10; 
 R′ H 3=Φ-C c H 2c  with c=1-10; 
 X is a halogen atom selected from the group consisting of chlorine and bromine. 
 
     
     
         5 . A process for preparing a compound selected from the group consisting of a sulfonimide compound (R—SO 2 ) 2 NH and salts thereof, (R—SO 2 ) 2 NMe, and a fluorinated compound having a sulfonic acid function —SO 2 OH and having a formula R—SO 2 OH, said process comprising:
 a step of preparing a compound R—SO 2 F of formula (I) as claimed in  claim 1 , 
 a step wherein said fluorinated compound of formula (I) is used as a reactive compound for the synthesis of a sulfonimide compound (R—SO 2 ) 2 NH and salts thereof, (R—SO 2 ) 2 NMe, or of a fluorinated compound having a sulfonic acid function —SO 2 OH and having a formula R—SO 2 OH,
 where R is selected from the group consisting of R1, R2 and R3: 
 R1=—C n H a F b  with n=1-10, a+b=2n+1, b≧1; 
 R2=—C x H y F z —SO 2 F with x=1-10, y+z=2x and z≧1; 
 R3=Φ-C c H h F f  with c=1-10; h+f=2c and f≧1; Φ denoting a phenyl group. 
 
 
     
     
         6 . The process as claimed in  claim 5 , wherein the compound synthesized is selected from the group consisting of bis(trifluoromethanesulfonyl)imide of formula (CF 3 SO 2 ) 2 NH and lithium bis(trifluoromethanesulfonyl)imide of formula (CF 3 SO 2 ) 2 NLi (LiTFSI) or selected from the group consisting of bis(fluorosulfonyl)imide of formula (F—SO 2 ) 2 NH and lithium bis(fluorosulfonyl)imide of formula (F—SO 2 ) 2 NLi (LiFSI). 
     
     
         7 . The process as claimed in  claim 5 , wherein the compound synthesized is trifluoromethanesulfonic acid of formula CF 3 SO 2 OH. 
     
     
         8 . An electrolyte salt, antistatic agent precursor or surfactant precursor, wherein said electrolyte salt, antistatic agent precursor or surfactant precursor is a sulfonimide compound or salt thereof obtained by the process defined in  claim 5 .