Preparation of Mono-N-sulphonylated diamines

Abstract

The present invention relates to a process for preparing mono-N-sulphonylated diamines by reacting diamines with sulphonyl halides in the presence of water, base and organic solvents.

1 . Solutions comprising compounds of the formula (I)  
     
       
         
         
             
             
         
       
       where  
       R 1  and R 2  are each independently C 1 -C 20 -alkyl, C 4 -C 15 -aryl or C 5 -C 16 -arylalkyl, or R 1  and R 2  together are a straight-chain or branched C 3 -C 12 -alkylene radical and  
       R 3  is C 1 -C 20 -alkyl, C 1 -C 20 -fluoroalkyl or C 4 -C 15 -aryl,  
       wherein the compounds of formula (I) are obtained by  
       a) reacting compounds of the formula (II)  
       
         
           
           
               
               
           
         
         where  
         R 1 , R 2  and R 3  are as defined under formula (I) 
 in the presence of water and  
 in the presence of organic solvents and  
 in the presence of a base  
 
         with sulphonyl halides of the formula (III)  
           R 3 SO 2 X  (III)  
         where  
         X is fluorine, chlorine, bromine or iodine and  
         R 3  is as defined under formula (I) and  
       
       b) at least partly removing water.  
     
   
   
       2 . A process of catalyzing reactions comprising providing solutions according to  claim 1  for application in said catalysis.  
   
   
       3 . A process for the preparation of catalysts comprising: 
 a) reacting compounds of the formula (II)                        where    R 1  and R 2  are each independently C 1 -C 20 -alkyl, C 4 -C 15 -aryl or C 5 -C 16 -arylalkyl, or R 1  and R 2  together are a straight-chain or branched C 3 -C 12 -alkylene radical and 
 in the presence of water and  
 in the presence of organic solvents and  
 in the presence of a base  
 with sulphonyl halides of the formula (III)  
   R 3 SO 2 X  (III)  
   where    X is fluorine, chlorine, bromine or iodine and    R 3  is C 1 -C 20 -alkyl, C 1 -C 20 -fluoroalkyl or C 4 -C 15 -aryl,      b) at least partly removing water and    c) reacting the solution obtained in step b) 
 with compounds of the formula (IV)  
   [MX n (R 4 )] 2   (IV)  
 where  
 M is ruthenium, rhodium or iridium,  
 R 4  is an aromatic compound which has 6 to 12 ring carbon atoms and may be substituted by up to 6 radicals which are each independently selected from the group of C 1 -C 8 -alkyl, benzyl and phenyl, or cyclopentadienyl or indenyl, each of which are substituted by up to five radicals, and  
 X is chlorine, bromine or iodine, and n is two where M is ruthenium,  
 n is one where M is rhodium or iridium.  
   
   
   
       4 . Catalysts made according to  claim 3 , wherein in formula (IV), M is ruthenium and n is two.