Method for storing quaternary ammonium salt

Abstract

A method of improving the stability of a quaternary ammonium salt and a method of efficiently preparing the quaternary ammonium salt having improved stability.

1 . A method of preserving a quaternary ammonium salt represented by the following general formula (I),  
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, R 2  is an alkyl group having 1 to 4 carbon atoms, and X is halogen atom,  
         (a) in the form of a hydrous quaternary ammonium salt containing 60 to 99% by weight of said quaternary ammonium salt and 40 to 1% by weight of water;  
         (b) by dissolving 100 parts by weight of said quaternary ammonium salt in 200 to 4000 parts by weight of water, and by freezing the thus obtained aqueous solution; or  
         (c) by decreasing the content of a triazine compound represented by the following general formula (II),  
         
           
             
             
                 
                 
             
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, and X is a halogen atom,  
         contained as an impurity in the quaternary ammonium salt down to smaller than 1% by weight and preserving said quaternary ammonium salt at a temperature of not higher than 25° C.  
       
     
     
         2 . A hydrous quaternary ammonium salt containing 60 to 99% by weight of a quaternary ammonium salt represented by the following general formula (I),  
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, R 2  is an alkyl group having 1 to 4 carbon atoms, and X is a halogen atom,  
         and 40 to 1% by weight of water.  
       
     
     
         3 . A quaternary ammonium salt represented by the following general formula (I),  
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, R 2  is an alkyl group having 1 to 4 carbon atoms, and X is a halogen atom,  
         containing a triazine compound represented by the following general formula (II),  
         
           
             
             
                 
                 
             
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, and X is a halogen atom,  
         in an amount of smaller than 1% by weight.  
       
     
     
         4 . A quaternary ammonium salt according to  claim 3 , wherein the quaternary ammonium salt represented by the above-mentioned general formula (I) is the one obtained by reacting a triazine compound represented by the above-mentioned general formula (II) with a morpholine compound represented by the following general formula (III),  
       
         
           
           
               
               
           
         
         wherein R 2  is an alkyl group having 1 to 4 carbon atoms.  
       
     
     
         5 . A quaternary ammonium salt according to  claim 3  or  4 , wherein the content of water is smaller than 1% by weight.  
     
     
         6 . A method of preparing a quaternary ammonium salt according to any one of  claims 1  to  4 , comprising reacting a triazine compound represented by the following general formula (II),  
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms,  
         and X is a halogen atom,  
         with a morpholine compound represented by the following general formula (III),  
         
           
             
             
                 
                 
             
           
         
         wherein R 2  is an alkyl group having 1 to 4 carbon atoms,  
         in an organic solvent in the presence of water of an amount of from 0.1 to 10 mols per mol of the triazine compound.  
       
     
     
         7 . A method of preparing a quaternary ammonium salt according to  claim 5 , comprising reacting a triazine compound represented by the following general formula (II),  
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, and X is a halogen atom,  
         with a morpholine compound represented by the following general formula (III),  
         
           
             
             
                 
                 
             
           
         
         wherein R 2  is an alkyl group having 1 to 4 carbon atoms,  
         in an organic solvent other than alcohol in the presence of water or alcohol of an amount of from 0.1 to 10 mols per mol of said triazine compound, and removing the organic solvent and water or alcohol.  
       
     
     
         8 . A condensing agent comprising a hydrous quaternary ammonium salt  claim 2 .  
     
     
         9 . A condensing agent containing 100 parts by weight of a quaternary ammonium salt represented by the following general formula (I),  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, R 2  is an alkyl group having 1 to 4 carbon atoms, and X is a halogen atom,  
       and 200 to 4000 parts by weight of water.  
     
     
         10 . A condensing agent comprising a quaternary ammonium salt represented by the following general formula (I),  
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, R 2  is an alkyl group having 1 to 4 carbon atoms, and X is a halogen atom,  
         containing a triazine compound represented by the following general formula (II),  
         
           
             
             
                 
                 
             
           
         
         wherein R 1  is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms, and X is a halogen atom,  
         in an amount of smaller than 1% by weight.  
       
     
     
         11 . A method of preparing an amide compound by reacting a carboxylic acid compound with an amine compound by using a condensing agent of any one of  claims 8  to  10 .  
     
     
         12 . A method of preparing an ester compound by reacting a carboxylic acid compound with an alcohol compound by using a condensing agent of any one of  claims 8  to  10 .