A method of producing a hydrofluoroolefin includes reacting a chlorofluoroolefin that is represented by Formula (I) or Formula (II) and that has 8 or less carbon atoms with a hydrogen molecule, in the presence of an intermetallic compound containing at least one first metal that is selected from the group consisting of palladium, platinum, rhodium, copper and iridium, and containing a second metal that is different from the first metal, to obtain a hydrofluoroolefin in which a hydrogen atom is substituted for at least a chlorine atom represented by Cl among chlorine atoms contained in Formula (I) or Formula (II).

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A method of producing a hydrofluoroolefin includes reacting a chlorofluoroolefin that is represented by Formula (I) or Formula (II) and that has 8 or less carbon atoms with a hydrogen molecule, in the presence of an intermetallic compound containing at least one first metal that is selected from the group consisting of palladium, platinum, rhodium, copper and iridium, and containing a second metal that is different from the first metal, to obtain a hydrofluoroolefin in which a hydrogen atom is substituted for at least a chlorine atom represented by Cl among chlorine atoms contained in Formula (I) or Formula (II).

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To provide a method for producing a hydrofluoroolefin, wherein formation of an over-reduced product having hydrogen added to an aimed hydrofluorolefin and an over-reduced product having some of fluorine atoms in the aimed product replaced with hydrogen atoms, as by-products, is suppressed.

A method for producing a hydrofluoroolefin, which comprises reacting a specific chlorofluoroolefin with hydrogen in the presence of a catalyst supported on a carrier, to obtain a specific hydrofluoroolefin, wherein the catalyst is a catalyst composed of particles of an alloy containing at least one platinum group metal selected from the group consisting of palladium and platinum, and gold, and the proportion of the gold at the surface of the alloy particles is from 5 to 30 mass % per 100 mass % in total of the platinum group metal and the gold at the surface of the alloy particles.

To provide a method for producing a hydrofluoroolefin, wherein formation of an over-reduced product having hydrogen added to an aimed hydrofluorolefin and an over-reduced product having some of fluorine atoms in the aimed product replaced with hydrogen atoms, as by-products, is suppressed.

A method for producing a hydrofluoroolefin, which comprises reacting a specific chlorofluoroolefin with hydrogen in the presence of a catalyst supported on a carrier, to obtain a specific hydrofluoroolefin, wherein the catalyst is a catalyst composed of particles of an alloy containing at least one platinum group metal selected from the group consisting of palladium and platinum, and gold, and the proportion of the gold at the surface of the alloy particles is from 5 to 30 mass % per 100 mass % in total of the platinum group metal and the gold at the surface of the alloy particles.

To provide a method for producing a hydrofluoroolefin, wherein formation of an over-reduced product having hydrogen added to an aimed hydrofluorolefin and an over-reduced product having some of fluorine atoms in the aimed product replaced with hydrogen atoms, as by-products, is suppressed.

A method for producing a hydrofluoroolefin, which comprises reacting a specific chlorofluoroolefin with hydrogen in the presence of a catalyst supported on a carrier, to obtain a specific hydrofluoroolefin, wherein the catalyst is a catalyst composed of particles of an alloy containing at least one platinum group metal selected from the group consisting of palladium and platinum, and gold, and the proportion of the gold at the surface of the alloy particles is from 5 to 30 mass % per 100 mass % in total of the platinum group metal and the gold at the surface of the alloy particles.

A process for the joint preparation of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene, comprising: (a) starting materials comprising at least one compound having the structure of formula I, II or III is reacted with hydrogen fluoride, producing 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane, and 1,2,3-trichloro-1,1,3-trifluoropropane; in the compounds of said formulae CF.sub.2−mCl.sub.m=CCl-CHF.sub.2−nCl.sub.n (Formula I), CF.sub.3−pCl.sub.pCHCl=CH.sub.2Cl (Formula II), and CF.sub.3−xCl.sub.xCF.sub.2−yCl.sub.yCHF.sub.2−zCl.sub.z (Formula III), m=0, 1, 2; n=1, 2; p=2, 3; x=1, 2, 3; y=1, 2; z=1, 2 and 4≦x+y+z≦6; (b) the 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane and 1,2,3-trichloro-1,1,3-trifluoropropane undergo dechlorination, producing 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene; and (c) the 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene are reacted with hydrogen fluoride, simultaneously yielding 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropen.

FIG. 1 is designated as the drawing of the Abstract.

A process for the joint preparation of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene, comprising: (a) starting materials comprising at least one compound having the structure of formula I, II or III is reacted with hydrogen fluoride, producing 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane, and 1,2,3-trichloro-1,1,3-trifluoropropane; in the compounds of said formulae CF.sub.2−mCl.sub.m=CCl-CHF.sub.2−nCl.sub.n (Formula I), CF.sub.3−pCl.sub.pCHCl=CH.sub.2Cl (Formula II), and CF.sub.3−xCl.sub.xCF.sub.2−yCl.sub.yCHF.sub.2−zCl.sub.z (Formula III), m=0, 1, 2; n=1, 2; p=2, 3; x=1, 2, 3; y=1, 2; z=1, 2 and 4≦x+y+z≦6; (b) the 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane and 1,2,3-trichloro-1,1,3-trifluoropropane undergo dechlorination, producing 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene; and (c) the 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene are reacted with hydrogen fluoride, simultaneously yielding 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropen.

FIG. 1 is designated as the drawing of the Abstract.

A process for the joint preparation of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene, comprising: (a) starting materials comprising at least one compound having the structure of formula I, II or III is reacted with hydrogen fluoride, producing 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane, and 1,2,3-trichloro-1,1,3-trifluoropropane; in the compounds of said formulae CF.sub.2−mCl.sub.m=CCl-CHF.sub.2−nCl.sub.n (Formula I), CF.sub.3−pCl.sub.pCHCl=CH.sub.2Cl (Formula II), and CF.sub.3−xCl.sub.xCF.sub.2−yCl.sub.yCHF.sub.2−zCl.sub.z (Formula III), m=0, 1, 2; n=1, 2; p=2, 3; x=1, 2, 3; y=1, 2; z=1, 2 and 4≦x+y+z≦6; (b) the 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane and 1,2,3-trichloro-1,1,3-trifluoropropane undergo dechlorination, producing 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene; and (c) the 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene are reacted with hydrogen fluoride, simultaneously yielding 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropen.

FIG. 1 is designated as the drawing of the Abstract.

The present invention aims to provide an efficient method for obtaining a desired isomer of HFO-1132 from a composition comprising trans-1,2-difluoroethylene (HFO-1132(E)) and cis-1,2-difluoroethylene (HFO-1132(Z)). The present invention provides, as a means for solving the problem, a method for producing HFO-1132(E) and/or HFO-1132(Z), comprising steps (1) to (3): (1) supplying a composition comprising HFO-1132(E) and/or HFO-1132(Z) to a reactor filled with a catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z); (2) separating the reaction product obtained in step (1) into a first stream comprising the HFO-1132(E) as a main component, and a second stream comprising the HFO-1132(Z) as a main component; and (3) recycling the first stream or the second stream obtained in step (2) to the reactor, to subject the first stream or the second stream to the isomerization reaction.

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.