An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2C═CA.sup.3-CA.sup.4=CA.sup.5A.sup.6 [A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8C═CA.sup.9X [A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

The present invention pertains to a novel process of manufacturing the compound 2,3,3,3-tetrafluoropropene (1234yf). The compound 1234yf is the newest refrigerant with zero OPD (Ozone Depleting Potential) and zero GWP (Global Warming Potential). Thus, the invention relates to a process, involving a carbene generation route, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), of the compound 243db (2,3-dichloro-1,1,1-trifluoropropane), and optionally of the compound 2-chloro-1,1,1-trifluoropropene (1233xf) via carbene route and compound 243db (2,3-dichloro-1,1,1-trifluoropropane). The invention also relates to a process for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), wherein the compound 243db (2,3-dichloro-1,1,1-trifluoropropane) serves as a starting material, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf). Further, the invention relates to a process for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), and of the compound 243db (2,3-dichloro-1,1,1-trifluoropropane), the initial starting materials are selected from the group consisting of com-pound 123 (2,2-dichloro-1,1,1-trifluoroethane), compound 124 (2-chloro-1,1,1,2-tetrafluoroethane), and compound 125 (pentafluoroethane).

The present invention pertains to a novel process of manufacturing the compound 2,3,3,3-tetrafluoropropene (1234yf). The compound 1234yf is the newest refrigerant with zero OPD (Ozone Depleting Potential) and zero GWP (Global Warming Potential). Thus, the invention relates to a process, involving a carbene generation route, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), of the compound 243db (2,3-dichloro-1,1,1-trifluoropropane), and optionally of the compound 2-chloro-1,1,1-trifluoropropene (1233xf) via carbene route and compound 243db (2,3-dichloro-1,1,1-trifluoropropane). The invention also relates to a process for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), wherein the compound 243db (2,3-dichloro-1,1,1-trifluoropropane) serves as a starting material, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf). Further, the invention relates to a process for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), and of the compound 243db (2,3-dichloro-1,1,1-trifluoropropane), the initial starting materials are selected from the group consisting of com-pound 123 (2,2-dichloro-1,1,1-trifluoroethane), compound 124 (2-chloro-1,1,1,2-tetrafluoroethane), and compound 125 (pentafluoroethane).

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine.

A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2CCA.sup.3-CA.sup.4CA.sup.5A.sup.6[A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8CCA.sup.9X[A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine.

A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2CCA.sup.3-CA.sup.4CA.sup.5A.sup.6[A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8CCA.sup.9X[A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

An apparatus for heat transfer includes a device and a mechanism for transferring heat to or from the device. The mechanism for transferring heat includes a working fluid that includes a hexafluoropropylene trimer having Structural Formula (1) The hexafluoropropylene trimer having Structural Formula (1) is present in the working fluid in an amount of at least 85% by weight, based on the total weight of hexafluoropropylene trimer in the working fluid. ##STR00001##

An apparatus for heat transfer includes a device and a mechanism for transferring heat to or from the device. The mechanism for transferring heat includes a working fluid that includes a hexafluoropropylene trimer having Structural Formula (1) The hexafluoropropylene trimer having Structural Formula (1) is present in the working fluid in an amount of at least 85% by weight, based on the total weight of hexafluoropropylene trimer in the working fluid. ##STR00001##

An apparatus for heat transfer includes a device and a mechanism for transferring heat to or from the device. The mechanism for transferring heat includes a working fluid that includes a hexafluoropropylene trimer having Structural Formula (1) The hexafluoropropylene trimer having Structural Formula (1) is present in the working fluid in an amount of at least 85% by weight, based on the total weight of hexafluoropropylene trimer in the working fluid. ##STR00001##

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 ZCFC-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 lanthanide 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 ZCFC-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 lanthanide element or silver.