Disclosed is a process for the preparation of cis-1,1,1,4,4,4-hexafluoro-2-butene comprising contacting 1,1,1-trifluorotrichloroethane with hydrogen in the presence of a catalyst comprising ruthenium to produce a product mixture comprising 1316mxx, recovering said 1316mxx as a mixture of Z- and E-isomers, contacting said 1316mxx with hydrogen, in the presence of a catalyst selected from the group consisting of copper on carbon, nickel on carbon, copper and nickel on carbon and copper and palladium on carbon, to produce a second product mixture, comprising E- or Z-CFC-1326mxz, and subjecting said second product mixture to a separation step to provide E- or Z-1326mxz. The E- or Z-1326mxz can be dehydrochlorinated in an aqueous basic solution with an alkali metal hydroxide in the presence of a phase transfer catalyst to produce hexafluoro-2-butyne, which can then be selectively hydrogenated to produce Z-1,1,1,4,4,4-hexafluoro-2-butene using either Lindlar's catalyst, or a palladium catalyst further comprising a lantanide element or silver.

Disclosed is a process for the preparation of cis-1,1,1,4,4,4-hexafluoro-2-butene comprising contacting 1,1,1-trifluorotrichloroethane with hydrogen in the presence of a catalyst comprising ruthenium to produce a product mixture comprising 1316mxx, recovering said 1316mxx as a mixture of Z- and E-isomers, contacting said 1316mxx with hydrogen, in the presence of a catalyst selected from the group consisting of copper on carbon, nickel on carbon, copper and nickel on carbon and copper and palladium on carbon, to produce a second product mixture, comprising E- or Z-CFC-1326mxz, and subjecting said second product mixture to a separation step to provide E- or Z-1326mxz. The E- or Z-1326mxz can be dehydrochlorinated in an aqueous basic solution with an alkali metal hydroxide in the presence of a phase transfer catalyst to produce hexafluoro-2-butyne, which can then be selectively hydrogenated to produce Z-1,1,1,4,4,4-hexafluoro-2-butene using either Lindlar's catalyst, or a palladium catalyst further comprising a lantanide element or silver.

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 method of separating 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) and 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) includes providing an untreated composition including 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) and 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a). The untreated composition is treated with an adsorbent to form a treated composition in which the concentration of 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) is less than 93 percent of the concentration of the 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) in the untreated composition based on a treatment time of 24 hours.

A method of separating 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) and 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) includes providing an untreated composition including 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) and 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a). The untreated composition is treated with an adsorbent to form a treated composition in which the concentration of 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) is less than 93 percent of the concentration of the 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) in the untreated composition based on a treatment time of 24 hours.

A process is provided comprising contacting and reacting the compound CF.sub.3CF.sub.2CHXCl, wherein X is H or Cl, or the compound CF.sub.3CF═CXCl, wherein X is H or Cl, with hydrogen in the presence of a catalyst consisting essentially of Cu, Ru, Cu—Pd, Ni—Cu, and Ni—Pd, to obtain as a result thereof reaction product comprising hydrofluoropropenes or intermediates convertible to said hydrofluoropropenes, notably CF.sub.3CF═CH.sub.2 and CF.sub.3CH═CHF.

A process is provided comprising contacting and reacting the compound CF.sub.3CF.sub.2CHXCl, wherein X is H or Cl, or the compound CF.sub.3CF═CXCl, wherein X is H or Cl, with hydrogen in the presence of a catalyst consisting essentially of Cu, Ru, Cu—Pd, Ni—Cu, and Ni—Pd, to obtain as a result thereof reaction product comprising hydrofluoropropenes or intermediates convertible to said hydrofluoropropenes, notably CF.sub.3CF═CH.sub.2 and CF.sub.3CH═CHF.

A process is provided comprising contacting and reacting the compound CF.sub.3CF.sub.2CHXCl, wherein X is H or Cl, or the compound CF.sub.3CF═CXCl, wherein X is H or Cl, with hydrogen in the presence of a catalyst consisting essentially of Cu, Ru, Cu—Pd, Ni—Cu, and Ni—Pd, to obtain as a result thereof reaction product comprising hydrofluoropropenes or intermediates convertible to said hydrofluoropropenes, notably CF.sub.3CF═CH.sub.2 and CF.sub.3CH═CHF.