GB745818A - Improvements in or relating to a process for producing fluorohalo-derivatives of saturated aliphatic hydrocarbons - Google Patents
Improvements in or relating to a process for producing fluorohalo-derivatives of saturated aliphatic hydrocarbonsInfo
- Publication number
- GB745818A GB745818A GB1481852A GB1481852A GB745818A GB 745818 A GB745818 A GB 745818A GB 1481852 A GB1481852 A GB 1481852A GB 1481852 A GB1481852 A GB 1481852A GB 745818 A GB745818 A GB 745818A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methane
- hydrogen
- fluoride
- chlorine
- bromine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/204—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being a halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Fluoro-chloro or bromo-substituted derivatives of methane, ethane and propane are prepared by a process wherein methane, ethane, ethylene, propane, or one of these hydrocarbons in which part of the hydrogen has been replaced by chlorine or bromine are treated, for the purpose of substituting both fluorine and chlorine or bromine for hydrogen, in the vapour phase and in the presence of a metallic halide oxidation catalyst with chlorine, bromine, hydrogen chloride, hydrogen bromide or a mixture of two or more of these and hydrogen fluoride and sufficient oxygen to form water by combination with all the hydrogen present in the hydrogen fluoride and other hydrogen halide initially present and also with that portion of the hydrogen originally combined with carbon and which becomes replaced by halogen during the rection. In a modification of the process, there is used the starting material already containing chlorine or bromine and the chlorine, bromine, hydrogen chloride or hydrogen bromide is introduced only in sufficient quantity to start and maintain the reaction, whereby fluorine only is substituted in the starting material. In both processes, the fluorine of the hydrogen fluoride replaces, not hydrogen, but chlorine or bromine in an intermediately formed chlorinated or brominated starting material. The processes are generally effected under atmospheric pressure at temperatures between 400 DEG and 500 DEG C. Fluorination may be allowed to proceed to various intermediate stages by adjustment in the amounts of reactants. The preferred catalyst is aluminium fluoride impregnated with cupric chloride and which may also contain chromic fluoride; chromic fluoride itself may be used as catalyst. In an example, methane and chlorine in equimolar amounts and air and hydrogen fluoride in 100 per cent excess are passed through a heated steel reactor containing aluminium fluoride-cupric chloride catalyst (see Group III) at 400-500 DEG C. with a contact time of 23 seconds resulting in a 30 per cent yield of difluoro dichloromethane; halving the amount of chlorine is stated to result in production of monochloro-difluoro-methane. Other reactions are described by means of equations whereby methane is converted into trichlorofluoro - methane, chloro - trifluoro - methane, monochloro - monofluoro - methane, dibromodifluoro - methane or bromo - chloro - difluoromethane; ethane or ethylene is converted into pentachloro - fluoro - ethane; monochloromethane is converted into trichloro-fluoromethane; and dichloro-methane is converted into dichloro-difluoro-methane. According to the Provisional Specification the processes may be applied to the treatment of aliphatic hydrocarbons or chlorinated, brominated or fluorinated aliphatic hydrocarbons and the proportion of hydrogen fluoride used may be so adjusted that complete fluorination may be effected and fluorocarbons produced as in the production of tetrafluoro-methane from dichloro-methane.ALSO:An aluminium fluoride catalyst impregnated with cupric chloride, useful in certain hydrofluorinations of organic compounds (see Group IV(b)), is prepared by pelleting aluminium silicofluoride containing 9 per cent sodium chloride and heating the pellets to 950 DEG C., whereby silicon tetrafluoride is set free, and then impregnating the pellets with a saturated solution of cupric chloride and drying. The catalyst may also contain chromic fluoride as a promotor.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1481852A GB745818A (en) | 1952-06-12 | 1952-06-12 | Improvements in or relating to a process for producing fluorohalo-derivatives of saturated aliphatic hydrocarbons |
FR1078266D FR1078266A (en) | 1952-06-12 | 1953-06-11 | Improved process for obtaining fluorohalogenated derivatives of saturated aliphatic hydrocarbons |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1481852A GB745818A (en) | 1952-06-12 | 1952-06-12 | Improvements in or relating to a process for producing fluorohalo-derivatives of saturated aliphatic hydrocarbons |
Publications (1)
Publication Number | Publication Date |
---|---|
GB745818A true GB745818A (en) | 1956-03-07 |
Family
ID=10048025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1481852A Expired GB745818A (en) | 1952-06-12 | 1952-06-12 | Improvements in or relating to a process for producing fluorohalo-derivatives of saturated aliphatic hydrocarbons |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1078266A (en) |
GB (1) | GB745818A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3078662A (en) * | 1959-02-24 | 1963-02-26 | Gulf Research Development Co | Non-corrosive vanadiumcontaining fuels |
US3541165A (en) * | 1962-12-28 | 1970-11-17 | Montedison Spa | Process for obtaining halogenated fluorine-containing hydrocarbons |
US4052470A (en) * | 1975-12-22 | 1977-10-04 | Allied Chemical Corporation | Process for the production of chlorofluorinated acyclic hydrocarbons |
US4052468A (en) | 1975-12-22 | 1977-10-04 | Allied Chemical Corporation | Process for the production of chlorofluorinated cycloaliphatic hydrocarbons |
US4060555A (en) * | 1975-12-22 | 1977-11-29 | Allied Chemical Corporation | Process for the production of chlorofluorinated aliphatic ketones |
FR2360538A1 (en) * | 1975-12-22 | 1978-03-03 | Allied Chem | Chlorofluorinated hydrocarbons prepn. by oxychlorofluorination - in increased yields by addn. of (partially) halogenated hydrocarbons |
US4194990A (en) * | 1977-02-11 | 1980-03-25 | Allied Chemical Corporation | Catalyst and process for the production of chlorofluorinated hydrocarbons |
US5354928A (en) * | 1990-05-11 | 1994-10-11 | Societe Atochem | Process for the manufacture of 1,1,1,2-tetrafluorochloroethane and of pentafluoroethane |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2871274A (en) * | 1955-02-16 | 1959-01-27 | Dow Chemical Co | Oxybromination of chlorodifluoromethane |
-
1952
- 1952-06-12 GB GB1481852A patent/GB745818A/en not_active Expired
-
1953
- 1953-06-11 FR FR1078266D patent/FR1078266A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3078662A (en) * | 1959-02-24 | 1963-02-26 | Gulf Research Development Co | Non-corrosive vanadiumcontaining fuels |
US3541165A (en) * | 1962-12-28 | 1970-11-17 | Montedison Spa | Process for obtaining halogenated fluorine-containing hydrocarbons |
US4052470A (en) * | 1975-12-22 | 1977-10-04 | Allied Chemical Corporation | Process for the production of chlorofluorinated acyclic hydrocarbons |
US4052468A (en) | 1975-12-22 | 1977-10-04 | Allied Chemical Corporation | Process for the production of chlorofluorinated cycloaliphatic hydrocarbons |
US4060555A (en) * | 1975-12-22 | 1977-11-29 | Allied Chemical Corporation | Process for the production of chlorofluorinated aliphatic ketones |
FR2360538A1 (en) * | 1975-12-22 | 1978-03-03 | Allied Chem | Chlorofluorinated hydrocarbons prepn. by oxychlorofluorination - in increased yields by addn. of (partially) halogenated hydrocarbons |
FR2361153A1 (en) * | 1975-12-22 | 1978-03-10 | Allied Chem | CATALYTIC MIXTURES, ESPECIALLY FOR THE PRODUCTION OF ORGANIC CHLOROFLUORA COMPOUNDS |
US4194990A (en) * | 1977-02-11 | 1980-03-25 | Allied Chemical Corporation | Catalyst and process for the production of chlorofluorinated hydrocarbons |
US5354928A (en) * | 1990-05-11 | 1994-10-11 | Societe Atochem | Process for the manufacture of 1,1,1,2-tetrafluorochloroethane and of pentafluoroethane |
Also Published As
Publication number | Publication date |
---|---|
FR1078266A (en) | 1954-11-17 |
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