Provided is a method for producing (alkyl)arene compounds represented by Formulae 3-1, 3-2, and 3-3 by the Friedel-Crafts alkylation reaction of alkyl halide compounds and arene compounds using organic phosphine compounds as a catalyst.

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Catalytic methods for synthesis of super linear alkenyl arenes and alkyl arenes are provided. The methods are capable of synthesizing super linear alkyl and alkenyl arenes from simple arene and olefin starting materials and with high selectivity for linear coupling. Methods are also provided for making a 2,6-dimethylnapthalene (DMN) or 2,6-methylethylnapthalene (MEN).

Catalytic methods for synthesis of super linear alkenyl arenes and alkyl arenes are provided. The methods are capable of synthesizing super linear alkyl and alkenyl arenes from simple arene and olefin starting materials and with high selectivity for linear coupling. Methods are also provided for making a 2,6-dimethylnapthalene (DMN) or 2,6-methylethylnapthalene (MEN).

Provided is a method for producing a perfluoroalkylated compound at low cost, safely and with high efficiency. A method for producing a perfluoroalkylated compound, comprising reacting a bis(perfluoroalkanoyl) peroxide with a compound having a carbon-carbon unsaturated bond and/or an aromatic ring having a hydrogen atom bonded thereto in the presence of a copper catalyst.

Provided is a method for producing a perfluoroalkylated compound at low cost, safely and with high efficiency. A method for producing a perfluoroalkylated compound, comprising reacting a bis(perfluoroalkanoyl) peroxide with a compound having a carbon-carbon unsaturated bond and/or an aromatic ring having a hydrogen atom bonded thereto in the presence of a copper catalyst.

The invention discloses a method for preparation of alkylated, fluoro alkylated, chloro alkylated and fluorochloro alkylated compounds by a heterogeneous Co-catalysed alkylation or fluoro, chloro and fluorochloro alkylation with alkyl halides, fluoro alkyl halides, chloro alkyl halides or fluorochloro alkyl halides respectively.

The invention discloses a method for preparation of alkylated, fluoro alkylated, chloro alkylated and fluorochloro alkylated compounds by a heterogeneous Co-catalysed alkylation or fluoro, chloro and fluorochloro alkylation with alkyl halides, fluoro alkyl halides, chloro alkyl halides or fluorochloro alkyl halides respectively.

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 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.