Preparation of imides containing a fluorosulfonyl group

Abstract

A process for preparing a fluoro compound of formula: R2—(SO2)—NX—(SO2)—F (III) including: (a) a first step for obtaining the chloro compound of formula: R1—(SO2)—NX—(SO2)—Cl; (II) this first step including the reaction of the sulfamide of formula: R0—(SO2)—NH2 (I) with a sulfurous acid and a chlorinating agent; and (b) a second step for obtaining the fluoro compound of formula (III), this second step including the reaction of the chloro compound of formula (II) with anhydrous hydrofluoric acid in at least one organic solvent; in which: X represents either a hydrogen atom or a monovalent cation M; R1 represents an electron-withdrawing group having a positive Hammett parameter σp; if R1 represents Cl, then R0 represents OH; otherwise, R0 is identical to R1; and if R1 represents Cl, then R2 represents F; otherwise, R2 is identical to R1.

1 . A composition comprising at least 99.9% by mass of an imide salt of formula:
   R 2 —(SO 2 )—NM—(SO 2 )—F  (IIIb)
   
       in which M represents a monovalent cation and R 2  represents an electron-withdrawing group having a positive Hammett parameter σ p , the composition comprising a mass content of total fluorides of from 1 to 500 ppm, and/or a mass content of total chlorides of from 1 to 200 ppm. 
     
     
         2 . The composition as in  claim 1 , in which the mass content of total fluorides is from 1 to 500 ppm, and the mass content of total chlorides is from 1 to 200 ppm. 
     
     
         3 . The composition as in  claim 1 , in which the mass content of total fluorides is from 1 to 250 ppm and/or the mass content of total chlorides is from 1 to 100 ppm. 
     
     
         4 . The composition as in  claim 1 , in which the mass content of total fluorides is from 1 to 250 ppm and the mass content of total chlorides is from 1 to 100 ppm. 
     
     
         5 . The composition as in  claim 1 , comprising a mass content of nitrates of less than or equal to 250 ppm; and/or comprising a mass content of sulfates of less than or equal to 250 ppm. 
     
     
         6 . The composition as in  claim 1 , comprising a mass content of nitrates of less than or equal to 250 ppm; and comprising a mass content of sulfates of less than or equal to 250 ppm. 
     
     
         7 . The composition as in  claim 1 , comprising a mass content of nitrates of less than or equal to 150 ppm; and/or comprising a mass content of sulfates of less than or equal to 150 ppm. 
     
     
         8 . The composition as in  claim 1 , comprising a mass content of nitrates of less than or equal to 150 ppm; and comprising a mass content of sulfates of less than or equal to 150 ppm. 
     
     
         9 . The composition as in  claim 1 , in which:
 M represents Li or Na or K; and/or   R 2  represents F, CF 3 , CHF 2 , CH 2 F, C 2 HF 4 , C 2 H 2 F 3 , C 2 H 3 F 2 , C 2 F 5 , C 3 F 7 , C 3 H 2 F 5 , C 3 H 4 F 3 , C 3 HF 6 , C 4 F 9 , C 4 H 2 F 7 , C 4 H 4 F 5 , C 5 F 11 , C 3 F 6 OCF 3 , C 2 F 4 OCF 3 , C 2 H 2 F 2 OCF 3 , CF 2 OCF 3 , C 6 F 13 , C 7 F 15 , C 8 F 17  or C 9 F 19 .   
     
     
         10 . The composition as in  claim 1 , in which:
 M represents Li or Na or K; and   R 2  represents F.   
     
     
         11 . The composition as in  claim 1 , in which the imide salt is LiN(SO 2 F) 2 , LiN(SO 2 CF 3 )(SO 2 F), LiN(SO 2 C 2 F 5 )(SO 2 F), LiN(SO 2 CF 2 OCF 3 )(SO 2 F), LiN(SO 2 C 3 HF 6 )(SO 2 F), LiN(SO 2 C 4 F 9 )(SO 2 F), LiN(SO 2 C 5 F H )(SO 2 F), LiN(SO 2 C 6 F 13 )(SO 2 F), LiN(SO 2 C 7 F 15 )(SO 2 F), LiN(SO 2 C 8 F 17 )(SO 2 F) or LiN(SO 2 C 9 F 19 )(SO 2 F) 
     
     
         12 . The composition as in  claim 1 , in which the imide salt is LiN(SO 2 F) 2 . 
     
     
         13 . The composition as in  claim 1 , in which:
 the mass content of total fluorides is from 1 to 250 ppm; and   the mass content of total chlorides is from 1 to 100 ppm,   
       the composition comprising:
 a mass content of nitrates of less than or equal to 250 ppm; 
 a mass content of sulfates of less than or equal to 250 ppm; 
 a mass content of nitrates of less than or equal to 150 ppm; and 
 a mass content of sulfates of less than or equal to 150 ppm, in which:
 M represents Li or Na or K; 
 R 2  represents F; and 
 the imide salt is LiN(SO 2 F) 2 .