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.

Clay stabilization compositions include one or a plurality of triamino compounds and/or derivatives thereof, fluids containing an effective amount of the clay stabilization compositions and methods for making and using same.

Clay stabilization compositions include one or a plurality of triamino compounds and/or derivatives thereof, fluids containing an effective amount of the clay stabilization compositions and methods for making and using same.

Disclosed herein is a process comprising contacting a haloalkane reactant with an olefin in the presence of a catalyst system that consists of metallic iron and a phosphine to produce a haloalkane insertion product, wherein said haloalkane reactant is an alkane substituted with at least one halogen selected from the group consisting of F, Cl, and combinations thereof. Also disclosed herein is a process comprising contacting CF.sub.3CCl.sub.3 with CH.sub.2═CHX in the presence of a catalyst system that consists of metallic iron and a phosphine to make CF.sub.3CCl.sub.2CH.sub.2CHClX, wherein X═F or Cl. Also disclosed are further reactions in a sequence to produce HFO-1336ze and HCFO-1335zd. Also disclosed herein is a new composition comprising the compound CF.sub.3CF.sub.2CH═CHCl.

Disclosed herein is a process comprising contacting a haloalkane reactant with an olefin in the presence of a catalyst system that consists of metallic iron and a phosphine to produce a haloalkane insertion product, wherein said haloalkane reactant is an alkane substituted with at least one halogen selected from the group consisting of F, Cl, and combinations thereof. Also disclosed herein is a process comprising contacting CF.sub.3CCl.sub.3 with CH.sub.2═CHX in the presence of a catalyst system that consists of metallic iron and a phosphine to make CF.sub.3CCl.sub.2CH.sub.2CHClX, wherein X═F or Cl. Also disclosed are further reactions in a sequence to produce HFO-1336ze and HCFO-1335zd. Also disclosed herein is a new composition comprising the compound CF.sub.3CF.sub.2CH═CHCl.

Disclosed is a process for producing a chlorinated C3-6 alkane comprising providing a reaction mixture comprising an alkene and carbon tetrachloride in a principal alkylation zone to produce chlorinated C3-6 alkane in the reaction mixture, and extracting a portion of the reaction mixture from the principal alkylation zone, wherein: a) the concentration of the chlorinated C3-6 alkane in the reaction mixture in the principal alkylation zone is maintained at a level such that the molar ratio of chlorinated C3-6 alkane:carbon tetrachloride in the reaction mixture extracted from the alkylation zone does not exceed 95:5 when the principal alkylation zone is in continuous operation; and/or b) the reaction mixture extracted from the principal alkylation zone additionally comprises alkene and the reaction mixture is subjected to a dealkenation step in which at least about 50% or more by weight of the alkene present in the reaction mixture is extracted therefrom and at least about 50% of the extracted alkene is fed back into the reaction mixture provided in the principal alkylation zone; and/or c) the reaction mixture present in the principal alkylation zone and extracted from the principal alkylation zone additionally comprises a catalyst, and the reaction mixture extracted from the principal alkylation zone is subjected to an aqueous treatment step in which the reaction mixture is contacted with an aqueous medium in an aqueous treatment zone, a biphasic mixture is formed and an organic phase comprising catalyst is extracted from the biphasic mixture.

Disclosed is a process for producing a chlorinated C3-6 alkane comprising providing a reaction mixture comprising an alkene and carbon tetrachloride in a principal alkylation zone to produce chlorinated C3-6 alkane in the reaction mixture, and extracting a portion of the reaction mixture from the principal alkylation zone, wherein: a) the concentration of the chlorinated C3-6 alkane in the reaction mixture in the principal alkylation zone is maintained at a level such that the molar ratio of chlorinated C3-6 alkane:carbon tetrachloride in the reaction mixture extracted from the alkylation zone does not exceed 95:5 when the principal alkylation zone is in continuous operation; and/or b) the reaction mixture extracted from the principal alkylation zone additionally comprises alkene and the reaction mixture is subjected to a dealkenation step in which at least about 50% or more by weight of the alkene present in the reaction mixture is extracted therefrom and at least about 50% of the extracted alkene is fed back into the reaction mixture provided in the principal alkylation zone; and/or c) the reaction mixture present in the principal alkylation zone and extracted from the principal alkylation zone additionally comprises a catalyst, and the reaction mixture extracted from the principal alkylation zone is subjected to an aqueous treatment step in which the reaction mixture is contacted with an aqueous medium in an aqueous treatment zone, a biphasic mixture is formed and an organic phase comprising catalyst is extracted from the biphasic mixture.

Disclosed is a process for producing a chlorinated C3-6 alkane comprising providing a reaction mixture comprising an alkene and carbon tetrachloride in a principal alkylation zone to produce chlorinated C3-6 alkane in the reaction mixture, and extracting a portion of the reaction mixture from the principal alkylation zone, wherein: a) the concentration of the chlorinated C3-6 alkane in the reaction mixture in the principal alkylation zone is maintained at a level such that the molar ratio of chlorinated C3-6 alkane:carbon tetrachloride in the reaction mixture extracted from the alkylation zone does not exceed 95:5 when the principal alkylation zone is in continuous operation; and/or b) the reaction mixture extracted from the principal alkylation zone additionally comprises alkene and the reaction mixture is subjected to a dealkenation step in which at least about 50% or more by weight of the alkene present in the reaction mixture is extracted therefrom and at least about 50% of the extracted alkene is fed back into the reaction mixture provided in the principal alkylation zone; and/or c) the reaction mixture present in the principal alkylation zone and extracted from the principal alkylation zone additionally comprises a catalyst, and the reaction mixture extracted from the principal alkylation zone is subjected to an aqueous treatment step in which the reaction mixture is contacted with an aqueous medium in an aqueous treatment zone, a biphasic mixture is formed and an organic phase comprising catalyst is extracted from the biphasic mixture.

A method of producing carbon tetrachloride includes providing a chloromethanes stream, combining the chloromethanes stream with chlorine and additional carbon tetrachloride to form a reaction mixture, wherein the reaction mixture includes at least stoichiometric levels of chlorine, introducing electromagnetic radiation to the reaction mixture and subjecting the reaction mixture to suitable reaction conditions to form product carbon tetrachloride, and collecting a product stream including the product carbon tetrachloride.