The invention relates to a new process for the manufacture or synthesis, respectively, of fluorinated benzenes and fluorinated benzophenones, and derivatives thereof, in particular of fluorobenzenes and derivatives thereof. The present invention particularly pertains to a novel environmentally friendly process for the synthesis of fluorinated benzenes and benzophenones as raw materials for the manufacture of polyaryletherketones (PAEKs).

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.

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.

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 disclosure provides a method for producing a reaction gas containing R-1132(E) with selectivity higher than that of known methods. Specifically, the present disclosure provides a method for producing a reaction gas containing (E)-1,2-difluoroethylene (R-1132(E)), (1) the method comprising a step of subjecting a starting material gas containing one or more fluoromethanes selected from the group consisting of chlorodifluoromethane (R-22), difluoromethane (R-32), and fluoromethane (R-41) to a reaction that involves thermal decomposition to obtain the reaction gas, and (2) the starting material gas having a water vapor content of 1 volume % or less.

The present disclosure provides a method for producing a reaction gas containing R-1132(E) with selectivity higher than that of known methods. Specifically, the present disclosure provides a method for producing a reaction gas containing (E)-1,2-difluoroethylene (R-1132(E)), (1) the method comprising a step of subjecting a starting material gas containing one or more fluoromethanes selected from the group consisting of chlorodifluoromethane (R-22), difluoromethane (R-32), and fluoromethane (R-41) to a reaction that involves thermal decomposition to obtain the reaction gas, and (2) the starting material gas having a water vapor content of 1 volume % or less.

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).

The invention relates to a new process for the manufacture or synthesis, respectively, of fluorinated benzenes and fluorinated benzophenones, and derivatives thereof, in particular of fluorobenzenes and derivatives thereof. The present invention particularly pertains to a novel environmentally friendly process for the synthesis of fluorinated benzenes and benzophenones as raw materials for the manufacture of polyaryletherketones (PAEKs).

The invention relates to a new process for the manufacture or synthesis, respectively, of fluorinated benzenes and fluorinated benzophenones, and derivatives thereof, in particular of fluorobenzenes and derivatives thereof. The present invention particularly pertains to a novel environmentally friendly process for the synthesis of fluorinated benzenes and benzophenones as raw materials for the manufacture of polyaryletherketones (PAEKs).