Methods for producing halogenated alkene compound and fluorinated alkyne compound

Abstract

A halogenated alkene compound and a fluorinated alkyne compound are obtained at a high conversion rate and high selectivity by employing any of the following methods (1) to (4):(1) a halogenated butane compound represented by CX1X2X3CHX4CFHCX5X6X7, wherein X1, X2, X3, X4, X5, X6, and X7 are the same or different and each is a halogen atom, to a dehydrofluorination reaction;(2) a halogenated butene compound represented by CX1X2X3CX4═CHCX5X6X7, wherein X1, X2, X3, X4, X5, X6, and X7 are as defined above, to a dehydrohalogenation reaction;(3) a halogenated alkane compound represented by CHX8A1CHX9A2, wherein A1 and A2 are each a fluorine atom or a perfluoroalkyl group, and X8 and X9 are the same or different and each is a halogen atom, to a dehydrohalogenation reaction in the presence of a catalyst in a gas phase; and(4) a halogenated alkene compound represented by CX8A1=CHA2, wherein A1, A2, and X8 are as defined above, to a dehydrohalogenation reaction in the presence of a catalyst.

1 - 24 . (canceled) 
     
     
         25 . A composition comprising a halogenated butene compound represented by formula (1A):
   CX 1 X 2 X 3 CX 4 ═CHCX 5 X 6 X 7   (1A)
   wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and X 7  are the same or different and each is a halogen atom,   the halogenated butene compound represented by formula (1A) being contained in an amount of 80.00 to 99.99 mol % based on the total amount of the composition, which is taken as 100 mol %.   
     
     
         26 . The composition according to  claim 25 , comprising, as the halogenated butene compound represented by formula (1A), an (E)-halogenated butene compound in an amount of 85.00 to 99.98 mol % based on the total amount of the composition, which is taken as 100 mol %. 
     
     
         27 . A composition comprising:
 a halogenated alkene compound represented by formula (2B):
   CX 8 A 1 =CHA 2   (2B)
 
   wherein A 1  and A 2  are the same or different and each is a fluorine atom or a perfluoroalkyl group, and X 8  is a halogen atom; and   at least one hydrofluorocarbon (HFC) compound selected from the group consisting of hexafluorobutene, hexafluorobutane, and octafluorobutane,   wherein the halogenated alkene compound represented by formula (2B) is contained in an amount of 80 mol % or more, and the hydrofluorocarbon (HFC) compound is contained in an amount of 20 mol % or less, based on the total amount of the composition, which is taken as 100 mol %.   
     
     
         28 . A composition comprising:
 a halogenated butyne compound represented by formula (3A):
   CX 1 X 2 X 3 C═CCX 5 X 6 X 7   (3A)
 
   
       wherein X 1 , X 2 , X 3 , X 5 , X 6 , and X 7  are the same or different and each is a halogen atom, or a fluorinated alkyne compound represented by formula (3B):
   CA 1 =CA 2   (3B)
 
 wherein A 1  and A 2  are the same or different and each is a fluorine atom or a perfluoroalkyl group; and 
 at least one hydrofluorocarbon (HFC) compound selected from the group consisting of trifluoromethane, difluoromethane, tetrafluoromethane, and monofluoromethane, 
 wherein the halogenated butyne compound represented by formula (3A) or the fluorinated alkyne compound represented by formula (3B) is contained in an amount of 80 mol % or more, and the hydrofluorocarbon (HFC) compound is contained in an amount of 20 mol % or less, based on the total amount of the composition, which is taken as 100 mol %. 
 
     
     
         29 . The composition according to  claim 25 , which is used as a cleaning gas, an etching gas, a refrigerant, a heat transfer medium, or a building block for organic synthesis. 
     
     
         30 . The composition according to  claim 26 , which is used as a cleaning gas, an etching gas, a refrigerant, a heat transfer medium, or a building block for organic synthesis. 
     
     
         31 . The composition according to  claim 27 , which is used as a cleaning gas, an etching gas, a refrigerant, a heat transfer medium, or a building block for organic synthesis. 
     
     
         32 . The composition according to  claim 28 , which is used as a cleaning gas, an etching gas, a refrigerant, a heat transfer medium, or a building block for organic synthesis.