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.

This disclosure relates to bridged bis(N-heterocyclic carbene)palladium(II) complexes, methods of preparing the complexes, and methods of using the complexes in Suzuki-Miyaura coupling reactions.

This disclosure relates to bridged bis(N-heterocyclic carbene)palladium(II) complexes, methods of preparing the complexes, and methods of using the complexes in Suzuki-Miyaura coupling reactions.

A method of producing a fluorine-containing compound is a method of producing a compound (30) having partial structure (3) by an insertion reaction of compound (20) into compound (10) that has partial structure (1), in the presence of an ionic catalyst formed from a specific monovalent anion and a counter cation. In the formulas, * represents a bonding site, and X.sup.1 and R.sup.1 to R.sup.4 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or an organic group having a carbon number of 1 to 20 which may have a substituent.

##STR00001##

A method of producing a fluorine-containing compound is a method of producing a compound (30) having partial structure (3) by an insertion reaction of compound (20) into compound (10) that has partial structure (1), in the presence of an ionic catalyst formed from a specific monovalent anion and a counter cation. In the formulas, * represents a bonding site, and X.sup.1 and R.sup.1 to R.sup.4 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or an organic group having a carbon number of 1 to 20 which may have a substituent.

##STR00001##

A method of producing a fluoroolefin includes contacting a compound of formula (1), R.sub.fCH═CHF, with a fluorinated ethylene compound of formula (2), CX.sub.1X.sub.2═CX.sub.3X.sub.4 in the presence of a Lewis acid catalyst. In the compound of formula (1), R.sub.f is a C.sub.1-C.sub.10 perfluorinated alkyl group. In the compound of formula (2), X.sub.1, X.sub.2, X.sub.3, and X.sub.4 are each independently H, Cl, or F and at least one of X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is F. The resulting composition comprises a compound of formula (3), R.sub.fCF.sub.3(CX.sub.5X.sub.6CX.sub.7X.sub.8).sub.nCH═CHCX.sub.9X.sub.10CX.sub.11X.sub.12F. In the compound of formula (3), X.sub.5, X.sub.6, X.sub.7, X.sub.8, X.sub.9, X.sub.10, X.sub.11, and X.sub.12 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of each of H, Cl, and F corresponds to the total number of each of H, Cl, and F provided by the fluorinated ethylene compound of formula (2).

A method of producing a fluoroolefin includes contacting a compound of formula (1), R.sub.fCH═CHF, with a fluorinated ethylene compound of formula (2), CX.sub.1X.sub.2═CX.sub.3X.sub.4 in the presence of a Lewis acid catalyst. In the compound of formula (1), R.sub.f is a C.sub.1-C.sub.10 perfluorinated alkyl group. In the compound of formula (2), X.sub.1, X.sub.2, X.sub.3, and X.sub.4 are each independently H, Cl, or F and at least one of X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is F. The resulting composition comprises a compound of formula (3), R.sub.fCF.sub.3(CX.sub.5X.sub.6CX.sub.7X.sub.8).sub.nCH═CHCX.sub.9X.sub.10CX.sub.11X.sub.12F. In the compound of formula (3), X.sub.5, X.sub.6, X.sub.7, X.sub.8, X.sub.9, X.sub.10, X.sub.11, and X.sub.12 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of each of H, Cl, and F corresponds to the total number of each of H, Cl, and F provided by the fluorinated ethylene compound of formula (2).

A method of producing a fluoroolefin includes contacting a compound of formula (1), R.sub.fCH═CHF, with a fluorinated ethylene compound of formula (2), CX.sub.1X.sub.2═CX.sub.3X.sub.4 in the presence of a Lewis acid catalyst. In the compound of formula (1), R.sub.f is a C.sub.1-C.sub.10 perfluorinated alkyl group. In the compound of formula (2), X.sub.1, X.sub.2, X.sub.3, and X.sub.4 are each independently H, Cl, or F and at least one of X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is F. The resulting composition comprises a compound of formula (3), R.sub.fCF.sub.3(CX.sub.5X.sub.6CX.sub.7X.sub.8).sub.nCH═CHCX.sub.9X.sub.10CX.sub.11X.sub.12F. In the compound of formula (3), X.sub.5, X.sub.6, X.sub.7, X.sub.8, X.sub.9, X.sub.10, X.sub.11, and X.sub.12 are each independently H, Cl, or F, n is an integer of 0 or 1, and the total number of each of H, Cl, and F corresponds to the total number of each of H, Cl, and F provided by the fluorinated ethylene compound of formula (2).