The present invention provides improved processes for preparing halogenated alkanes. The processes comprise contacting at least one alkene, a halogenated alkene, or combinations thereof with a halogenated methane with at least one chlorine atom to form a liquid phase. This liquid phase is then contacted with at least one catalytic species which initiates the reaction with at least one alkene, a halogenated alkene, or combinations thereof with a halogenated methane with at least one chlorine atoms.

The present invention provides improved processes for preparing halogenated alkanes. The processes comprise contacting at least one alkene, a halogenated alkene, or combinations thereof with a halogenated methane with at least one chlorine atom to form a liquid phase. This liquid phase is then contacted with at least one catalytic species which initiates the reaction with at least one alkene, a halogenated alkene, or combinations thereof with a halogenated methane with at least one chlorine atoms.

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 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 provides a method of converting a brominated hydrocarbon to a chlorinated hydrocarbon that involves contacting together the brominated hydrocarbon and a chlorinated ion exchange resin that has a water content of less than or equal to 30 percent by weight, based on the total weight of the chlorinated ion exchange resin and the water. The brominated hydrocarbon includes at least one replaceable bromo group, where each replaceable bromo group is independently covalently bonded to an sp.sup.3 hybridized carbon. Contact between the brominated hydrocarbon and the chlorinated ion exchange resin results in replacement of at least one replaceable bromo group of the brominated hydrocarbon with a chloro group, and correspondingly conversion of at least a portion of the brominated hydrocarbon to the chlorinated hydrocarbon.

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 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.