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.

The present invention relates to a process for purifying olefin feed comprising R-5 1234yf, R-40, R-134a, R-134, R-1225zc, and OFCB, comprising the step of separating different ternary and binary azeotrope compositions comprising 1234yf. The olefin feed is obtained from the pyrolysis of tetrafluoroethylene/chlorodifluoromethane with chloromethane/methane, optionally in presence of initiator.

The present invention provides highly efficient processes for the preparation of chlorinated alkanes. The processes comprise contacting an alkene, halogenated alkene, or combinations thereof, a halogenated methane comprising at least one chlorine atom, at least one solid metallic catalyst, and a ligand forming a reaction mixture in a reactor. The product mixture does not contain a phase transfer catalyst. After a product mixture is formed, various fractions, distillation streams, and effluent streams are separated and/or treated with an aqueous alkaline substance. This treatment removes at least a portion of the metal and through recycling of the heavy fraction, treated product mixture, or combinations thereof, allows for the kinetics of the process to be maintained or increased.

The present invention provides highly efficient processes for the preparation of chlorinated alkanes. The processes comprise contacting an alkene, halogenated alkene, or combinations thereof, a halogenated methane comprising at least one chlorine atom, at least one solid metallic catalyst, and a ligand forming a reaction mixture in a reactor. The product mixture does not contain a phase transfer catalyst. After a product mixture is formed, various fractions, distillation streams, and effluent streams are separated and/or treated with an aqueous alkaline substance. This treatment removes at least a portion of the metal and through recycling of the heavy fraction, treated product mixture, or combinations thereof, allows for the kinetics of the process to be maintained or increased.

The present application provides a hydrodefluorodimerization process, which is useful in the synthesis of, for example, fluoroolefins that can be used as refrigerants, blowers and the like. The process is an early-stage fluorination process, wherein precursors containing fluorine are assembled into the desired product using a zerovalent nickel catalyst. Also provided is a liquid composition comprising one or more fluoroolefin produced by this catalytic process.

The present application provides a hydrodefluorodimerization process, which is useful in the synthesis of, for example, fluoroolefins that can be used as refrigerants, blowers and the like. The process is an early-stage fluorination process, wherein precursors containing fluorine are assembled into the desired product using a zerovalent nickel catalyst. Also provided is a liquid composition comprising one or more fluoroolefin produced by this catalytic process.

The present invention provides an improved process for preparation of 2,3,3,3-tetrafluoropropene, wherein recyclization of the reaction by-products result in equilibrium between feed and outlet composition.

The present invention provides an improved process for preparation of 2,3,3,3-tetrafluoropropene, wherein recyclization of the reaction by-products result in equilibrium between feed and outlet composition.

The present invention provides an improved process for preparation of 2,3,3,3-tetrafluoropropene, wherein recyclization of the reaction by-products result in equilibrium between feed and outlet composition.

The present application provides a hydrodefluorodimerization process, which is useful in the synthesis of, for example, fluorolefins that can be used as refrigerants, blowers and the like. The process is an early-stage fluorination process, wherein precursors containing fluorine are assembled into the desired product using a zerovalent nickel catalyst. Also provided is a liquid composition comprising one or more fluorolefin produced by this catalytic process.