Highly branched perfluoroolefins, super-stable perfluoroalkyl radicals and production methods thereof

Abstract

The present invention is to provide a method for producing a highly branched perfluoroolefin conveniently in a high yield, a novel highly branched perfluoroolefin, a method for producing a super-stable perfluoroalkyl radical and a novel super-stable perfluoroalkyl radical. The present invention is a production method of a perfluoroolefin which comprises reacting a hexafluoropropene trimer with a trialkylperfluoroalkylsilane in an aprotic polar solvent using a fluoride ion as a catalyst.

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         10 . A production method of a super-stable perfluoroalkyl radical 
 which comprises producing a super-stable perfluoroalkyl radical represented by the following general formula (1R):      [(CF 3 ) 2 CF][(CF 3 ) 2 CY]Ra—CF(CF 3 )Z   (1R)    in the formula, Ra represents a carbon atom having one unpaired electron, Y and Z are the same or different and each represents F or Rf, and Rf represents a straight or branched perfluoroalkyl group having 1 to 16 carbon atoms, provided that Y and Z are not simultaneously F,    by fluorinating a highly branched perfluoroolefin represented by the following general formula (1):      [(CF 3 ) 2 CF][(CF 3 ) 2 CY]C═C(CF 3 )Z   (1)    in the formula, Y, and Z are the same or different and each represents F or Rf, Rf represents a straight or branched perfluoroalkyl group having 1 to 16 carbon atoms, provided that Y and Z are not simultaneously F.    
     
     
         11 . The production method of the super-stable perfluoroalkyl radical according to  claim 10 , 
 wherein the fluorination is conducted using a fluorine gas.    
     
     
         12 . The production method of the super-stable perfluoroalkyl radical according to  claim 11 , wherein the fluorine gas is a pure one.  
     
     
         13 . The production method of the super-stable perfluoroalkyl radical according to  claim 10 , 
 wherein the highly branched perfluoroolefin is one obtained by reacting a hexafluoropropene trimer with a trialkylperfluoroalkylsilane represented by the following general formula (2):                          in the formula, Rf represents a straight or branched perfluoroalkyl group having 1 to 16 carbon atoms, R 1 , R 2  and R 3  are the same or different and each represents an alkyl group having 1 to 3 carbon atoms,    in an aprotic polar solvent using a fluoride ion as a catalyst.    
     
     
         14 . The production method of the super-stable perfluoroalkyl radical according to  claim 10 , 
 wherein Y and Z are the same or different and each represents F or a trifluoromethyl group, provided that Y and Z are not simultaneously F.    
     
     
         15 . The production method of the super-stable perfluoroalkyl radical according to  claim 10 , 
 wherein the highly branched perfluoroolefin is    perfluoro(2,4-dimethyl-3-isopropyl-2-pentene), perfluoro(2,4,4-trimethyl-3-isopropyl-2-pentene) or perfluoro(4,4-dimethyl-3-isopropyl-2-pentene).    
     
     
         16 . A production method of a reduced-carbon super-stable perfluoroalkyl radical 
 which comprises producing a super-stable perfluoroalkyl radical (AR) represented by the following general formula (3R):      [(CF 3 ) 2 CF] 2 Ra—CF(CF 3 )Rf   (3R)    in the formula, Ra represents a carbon atom having one unpaired electron and Rf represents a straight or branched perfluoroalkyl group having 1 to 16 carbon atoms,    by fluorinating a highly branched perfluoroolefin (B) represented by the following general formula (4):      [(CF 3 ) 2 CF][(CF 3 ) 2 CRf]C═C(CF 3 )Rf   (4)    in the formula, each Rf is the same or different from 5 each other and is defined as described above.    
     
     
         17 . The production method of the reduced-carbon super-stable perfluoroalkyl radical according to  claim 16 , 
 wherein Rf represents a trifluoromethyl group.    
     
     
         18 . A super-stable perfluoroalkyl radical (BR) represented by the following general formula (4R):  
         [(CF 3 ) 2 CF][(CF 3 ) 2 CRf]Ra—CF(CF 3 )Rf   (4R)  
       in the formula, Ra represents a carbon atom having one unpaired electron and each Rf is the same or different from each other and represents a straight or branched perfluoroalkyl group having 1 to 16 carbon atoms.  
     
     
         19 . The super-stable perfluoroalkyl radical according to  claim 18 , which is perfluoro(2,4,4-trimethyl-3-isopropyl-3-pentyl).  
     
     
         20 . A super-stable perfluoroalkyl radical (CR) represented by the following general formula (5R):  
         [(CF 3 ) 2 CF][(CF 3 ) 2 CRf]Ra—CF 2 (CF 3 )   (5R)  
       in the formula, Ra represents a carbon atom having one unpaired electron and Rf represents a straight or branched perfluoroalkyl group having 1 to 16 carbon atoms.  
     
     
         21 . The super-stable perfluoroalkyl radical according to  claim 20 , 
 which is perfluoro(4,4-dimethyl-3-isopropyl-3-pentyl).