Provided is a method that is for producing hexafluoro-1,3-butadiene, discharges small amounts of industrial wastes, and is industrially applicable. The method for producing hexafluoro-1,3-butadiene includes a reaction step of reacting a halogenated butane represented by chemical formula, CF.sub.2X.sup.1-CFX.sup.2-CFX.sup.3-CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom) in an organic solvent in the presence of zinc to eliminate the halogen atoms, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, other than the fluorine atoms to generate hexafluoro-1,3-butadiene, giving a reaction product containing the hexafluoro-1,3-butadiene, and an aftertreatment step of separating the hexafluoro-1,3-butadiene from the reaction product produced in the reaction step, then adding water to a reaction product residue after the separating, and removing the organic solvent, giving an aqueous solution of zinc halide.

Provided is a method that is for producing hexafluoro-1,3-butadiene, discharges small amounts of industrial wastes, and is industrially applicable. The method for producing hexafluoro-1,3-butadiene includes a reaction step of reacting a halogenated butane represented by chemical formula, CF.sub.2X.sup.1-CFX.sup.2-CFX.sup.3-CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom) in an organic solvent in the presence of zinc to eliminate the halogen atoms, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, other than the fluorine atoms to generate hexafluoro-1,3-butadiene, giving a reaction product containing the hexafluoro-1,3-butadiene, and an aftertreatment step of separating the hexafluoro-1,3-butadiene from the reaction product produced in the reaction step, then adding water to a reaction product residue after the separating, and removing the organic solvent, giving an aqueous solution of zinc halide.

Provided is a method that is for producing hexafluoro-1,3-butadiene, discharges small amounts of industrial wastes, and is industrially applicable. The method for producing hexafluoro-1,3-butadiene includes a reaction step of reacting a halogenated butane represented by chemical formula, CF.sub.2X.sup.1-CFX.sup.2-CFX.sup.3-CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom) in an organic solvent in the presence of zinc to eliminate the halogen atoms, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, other than the fluorine atoms to generate hexafluoro-1,3-butadiene, giving a reaction product containing the hexafluoro-1,3-butadiene, and an aftertreatment step of separating the hexafluoro-1,3-butadiene from the reaction product produced in the reaction step, then adding water to a reaction product residue after the separating, and removing the organic solvent, giving an aqueous solution of zinc halide.

A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with hydrogen fluoride in the vapor phase in the presence of a fluorination catalyst comprising a metal halide to produce E- and Z-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene further comprises contacting E- and Z-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene with base to produce 1,1,1,4,4,4-hexafluoro-2-butyne, and subsequently hydrogenating hexafluoro-2-butyne to produce Z-1,1,1,4,4,4-hexafluoro-2-butene.

A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with hydrogen fluoride in the vapor phase in the presence of a fluorination catalyst comprising a metal halide to produce E- and Z-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene further comprises contacting E- and Z-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene with base to produce 1,1,1,4,4,4-hexafluoro-2-butyne, and subsequently hydrogenating hexafluoro-2-butyne to produce Z-1,1,1,4,4,4-hexafluoro-2-butene.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.

A process for producing E-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with hydrogen fluoride in the vapor phase in the presence of a fluorination catalyst. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene further comprises contacting E-1,1,1,4,4,4-hexafluoro-2-butene with chlorine in the presence of a catalyst to produce 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane, followed by reaction with base to produce 1,1,1,4,4,4-hexafluoro-2-butyne, and subsequently hydrogenating hexafluoro-2-butyne to produce Z-1,1,1,4,4,4-hexafluoro-2-butene.

A process for producing E-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with hydrogen fluoride in the vapor phase in the presence of a fluorination catalyst. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene further comprises contacting E-1,1,1,4,4,4-hexafluoro-2-butene with chlorine in the presence of a catalyst to produce 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane, followed by reaction with base to produce 1,1,1,4,4,4-hexafluoro-2-butyne, and subsequently hydrogenating hexafluoro-2-butyne to produce Z-1,1,1,4,4,4-hexafluoro-2-butene.

According to a method for producing a perfluoroalkadiene compound represented by general formula (1): CF.sub.2═CF—(CF.sub.2).sub.n-4—CF═CF.sub.2 (1), wherein n is an integer of 4 or more, the method comprising a reaction step of adding a nitrogen-containing compound to a solution of a compound represented by general formula (2): X.sup.1CF.sub.2—CFX.sup.2—(CF.sub.2).sub.n-4—CF.sub.2—CF.sub.2X.sup.1 (2), wherein n is the same as above, X.sup.1 is the same or different and is a halogen atom other than fluorine, and X.sup.2 is a halogen atom, the perfluoroalkadiene compound can be obtained at a high yield.