Disclosed is a manufacturing method of 1,2-dichlorohexafluorocyclopentene. The first reaction uses dicyclopentadiene as a starting material and nitrogen gas or another inert gas as a diluting agent in a gas-phase thermal cracking reaction to obtain cyclopentadiene. The second reaction uses cyclopentadiene as a starting material in a liquid phase chlorination reaction with chlorine gas to obtain 1,2,3,4-tetrachlorocyclopentane. The third reaction uses 1,2,3,4-tetrachlorocyclopentane as a starting material in a gas-phase chlorination and fluorination reaction with hydrogen fluoride and chlorine gas in the presence of a chromium-based catalyst to obtain 1,2-dichlorohexafluorocyclopentene. The method uses easily acquired starting material and a stable fluorination catalyst, provides a high yield for a target product, and is applicable for large-scale continuous gas-phase production of 1,2-dichlorohexafluorocyclopentene.

Disclosed is a manufacturing method of 1,2-dichlorohexafluorocyclopentene. The first reaction uses dicyclopentadiene as a starting material and nitrogen gas or another inert gas as a diluting agent in a gas-phase thermal cracking reaction to obtain cyclopentadiene. The second reaction uses cyclopentadiene as a starting material in a liquid phase chlorination reaction with chlorine gas to obtain 1,2,3,4-tetrachlorocyclopentane. The third reaction uses 1,2,3,4-tetrachlorocyclopentane as a starting material in a gas-phase chlorination and fluorination reaction with hydrogen fluoride and chlorine gas in the presence of a chromium-based catalyst to obtain 1,2-dichlorohexafluorocyclopentene. The method uses easily acquired starting material and a stable fluorination catalyst, provides a high yield for a target product, and is applicable for large-scale continuous gas-phase production of 1,2-dichlorohexafluorocyclopentene.

A method for producing a fluorinated compound comprises: the provision of a gaseous flow comprising hydrofluoric acid; the provision of at least one liquid flow of a chlorinated compound and the vapourisation thereof by mixing with the gaseous flow, the resulting mixture being a gaseous mixture; and the catalytic reaction of the chlorinated compound with hydrofluoric acid in a gaseous phase and the collection of a product flow. The invention also relates to a facility for carrying out the method.

A method for producing a fluorinated compound comprises: the provision of a gaseous flow comprising hydrofluoric acid; the provision of at least one liquid flow of a chlorinated compound and the vapourisation thereof by mixing with the gaseous flow, the resulting mixture being a gaseous mixture; and the catalytic reaction of the chlorinated compound with hydrofluoric acid in a gaseous phase and the collection of a product flow. The invention also relates to a facility for carrying out the method.

A method for producing a fluorinated compound comprises: the provision of a gaseous flow comprising hydrofluoric acid; the provision of at least one liquid flow of a chlorinated compound and the vapourisation thereof by mixing with the gaseous flow, the resulting mixture being a gaseous mixture; and the catalytic reaction of the chlorinated compound with hydrofluoric acid in a gaseous phase and the collection of a product flow. The invention also relates to a facility for carrying out the method.

A process is disclosed for making CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2 and/or CF.sub.3CClCH.sub.2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX.sub.3CH.sub.2CH.sub.2X, halopropenes of the formula CX.sub.3CHCH.sub.2 and halopropenes of the formula CX.sub.2CHCH.sub.2X, wherein each X is independently F or Cl, with HF and Cl.sub.2 in a reaction zone to produce a product mixture comprising HF, HCl, CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2, and CF.sub.3CClCH.sub.2; and recovering the CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2 and/or CF.sub.3CClCH.sub.2 from the product mixture. Also disclosed is a process for making CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF, and/or CF.sub.3CHCHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX.sub.3CHCH.sub.2 and halopropenes of the formula CX.sub.2CHCH.sub.2X, wherein each X is independently F or Cl, with HF and Cl.sub.2 in a reaction zone to produce a product mixture comprising HF, HCl, CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF and CF.sub.3CHCHCl; and recovering the CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF, and/or CF.sub.3CHCHCl from the product mixture. The molar ratio of HF to the total amount of starting materials fed to the reaction zone for both of these processes is at least stoichiometric, and the molar ratio of Cl.sub.2 to total amount of starting material fed to the reaction zone for both of these processes is 2:1 or less.

A process is disclosed for making CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2 and/or CF.sub.3CClCH.sub.2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX.sub.3CH.sub.2CH.sub.2X, halopropenes of the formula CX.sub.3CHCH.sub.2 and halopropenes of the formula CX.sub.2CHCH.sub.2X, wherein each X is independently F or Cl, with HF and Cl.sub.2 in a reaction zone to produce a product mixture comprising HF, HCl, CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2, and CF.sub.3CClCH.sub.2; and recovering the CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2 and/or CF.sub.3CClCH.sub.2 from the product mixture. Also disclosed is a process for making CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF, and/or CF.sub.3CHCHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX.sub.3CHCH.sub.2 and halopropenes of the formula CX.sub.2CHCH.sub.2X, wherein each X is independently F or Cl, with HF and Cl.sub.2 in a reaction zone to produce a product mixture comprising HF, HCl, CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF and CF.sub.3CHCHCl; and recovering the CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF, and/or CF.sub.3CHCHCl from the product mixture. The molar ratio of HF to the total amount of starting materials fed to the reaction zone for both of these processes is at least stoichiometric, and the molar ratio of Cl.sub.2 to total amount of starting material fed to the reaction zone for both of these processes is 2:1 or less.

A process is disclosed for making CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2 and/or CF.sub.3CClCH.sub.2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX.sub.3CH.sub.2CH.sub.2X, halopropenes of the formula CX.sub.3CHCH.sub.2 and halopropenes of the formula CX.sub.2CHCH.sub.2X, wherein each X is independently F or Cl, with HF and Cl.sub.2 in a reaction zone to produce a product mixture comprising HF, HCl, CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2, and CF.sub.3CClCH.sub.2; and recovering the CF.sub.3CF.sub.2CH.sub.3, CF.sub.3CFCH.sub.2 and/or CF.sub.3CClCH.sub.2 from the product mixture. Also disclosed is a process for making CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF, and/or CF.sub.3CHCHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX.sub.3CHCH.sub.2 and halopropenes of the formula CX.sub.2CHCH.sub.2X, wherein each X is independently F or Cl, with HF and Cl.sub.2 in a reaction zone to produce a product mixture comprising HF, HCl, CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF and CF.sub.3CHCHCl; and recovering the CF.sub.3CH.sub.2CHF.sub.2, CF.sub.3CHCHF, and/or CF.sub.3CHCHCl from the product mixture. The molar ratio of HF to the total amount of starting materials fed to the reaction zone for both of these processes is at least stoichiometric, and the molar ratio of Cl.sub.2 to total amount of starting material fed to the reaction zone for both of these processes is 2:1 or less.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.