Fluorobutene derivatives and process for producing same

Abstract

The present invention provides novel compounds 2,4,4,4-tetrafluoro-1-butene and (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes. Furthermore, the present invention provides the following novel first and second processes for producing 2,4,4,4-tetrafluoro-1-butene and (E)- and Z-1,1,1,3-tetrafluoro-2-butenes. The first process is a process for producing 2,4,4,4-tetrafluoro-1-butene by heating 1,1,1,3,3-pentafluorobutane at from about 200° C. to about 700° C. The second process is a process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes by bringing 1,1,1,3,3-pentafluorobutane with a base. By the first and second processes, it is possible to obtain respective target fluorobutenes with high selectivity.

1 . 2,4,4,4-tetrafluoro-1-butene.  
     
     
         2 . (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes.  
     
     
         3 . (E)- or (Z)-1,1,1,3-tetrafluoro-2-butene.  
     
     
         4 . A process for producing 2,4,4,4-tetrafluoro-1-butene, characterized in that 1,1,1,3,3-pentafluorobutane is heated at from about 200° C. to about 700° C.  
     
     
         5 . A process for producing 2,4,4,4-tetrafluoro-1-butene according to  claim 4 , characterized in that the heating of  claim 4  is conducted under a condition that is substantially free of a base.  
     
     
         6 . A process for producing 2,4,4,4-tetrafluoro-1-butene according to  claim 4 , characterized in that the heating is conducted by passing 1,1,1,3,3-pentafluorobutane through a reaction tube heated at from about 200° C. to about 700° C.  
     
     
         7 . A process for producing 2,4,4,4-tetrafluoro-1-butene according to  claim 5 , characterized in that the heating is conducted by passing 1,1,1,3,3-pentafluorobutane through a reaction tube heated at from about 200° C. to about 700° C.  
     
     
         8 . A process for producing 2,4,4,4-tetrafluoro-1-butene, characterized in that 1,1,1,3,3-pentafluorobutane is passed through a reaction tube heated at 400° C.-500° C. under a condition that is substantially free of a base.  
     
     
         9 . A process for producing 2,4,4,4-tetrafluoro-1-butene according to  claim 8 , characterized in that the passing of the 1,1,1,3,3-pentafluorobutane to the reaction tube according to  claim 8  is conducted with an input raw material standard contact time of 18-40 seconds.  
     
     
         10 . A process for producing and isolating 2,4,4,4-tetrafluoro-1-butene, characterized in that a mixture containing 2,4,4,4-tetrafluoro-1-butene is obtained by a process of  claim 4 , and then the mixture is subjected to a distillation.  
     
     
         11 . A process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes, characterized in that 1,1,1,3,3-pentafluorobutane is heated at from about 200° C. to about 700° C.  
     
     
         12 . A process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes, characterized in that 1,1,1,3,3-pentafluorobutane is brought into contact with a base.  
     
     
         13 . A process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes according to  claim 12 , characterized in that the contact of the 1,1,1,3,3-pentafluorobutane with the base is conducted at from 0 to 300° C.  
     
     
         14 . A process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes according to  claim 12 , characterized in that the base is a base selected from alkali metal hydroxides, alkali earth metal hydroxides and tertiary amines.  
     
     
         15 . A process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes according to  claim 13 , characterized in that the base is a base selected from alkali metal hydroxides, alkali earth metal hydroxides, and tertiary amines.  
     
     
         16 . A process for producing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes according to  claim 12 , characterized in that the contact of the 1,1,1,3,3-pentafluorobutane with the base in  claim 12  is conducted under a coexistence with water, an ether, a halogen solvent, or a phase transfer catalyst.  
     
     
         17 . A process for producing and isolating (E)-1-1-1,3-tetrafluoro-2-butene, characterized in that a reaction mixture containing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes is obtained by the contact with the base in  claim 12 , and then the mixture is subjected to a distillation.  
     
     
         18 . A process for producing and isolating (Z)-1,1,1,3-tetrafluoro-2-butene, characterized in that a reaction mixture containing (E)- and (Z)-1,1,1,3-tetrafluoro-2-butenes is obtained by the contact with the base in  claim 12 , and then the mixture is subjected to a distillation.