GB744256A - Improvements in or relating to telomerization process - Google Patents
Improvements in or relating to telomerization processInfo
- Publication number
- GB744256A GB744256A GB12880/53A GB1288053A GB744256A GB 744256 A GB744256 A GB 744256A GB 12880/53 A GB12880/53 A GB 12880/53A GB 1288053 A GB1288053 A GB 1288053A GB 744256 A GB744256 A GB 744256A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- sulphuryl
- tetrafluoroethylene
- chlorotrifluoroethylene
- fluoride
- 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
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Distillable telomers of the formula W-(X)n-W or W-(X,Y)n-W, where W is chlorine, bromine or fluorine, X and Y are halo-olefinic monomers and n is greater than 1, are made by telomerizing the monomer or monomers under anhydrous conditions with a sulphuryl halide in the presence of a polymerization catalyst. Suitable monomers are vinyl chloride, bromide and fluoride, vinylidene chloride and fluoride, 2-chloropropene, a -chloro- and -bromo-styrenes, trifluoroethylene, tetrafluoroethylene, tetrachloropropene, chlorotrifluoroethylene, bromotrifluoroethylene, unsym.-dibromodifluoro- and dichlorodifluoro-ethylenes, chlorobutadiene, perfluorobutadiene, perfluorocyclobutene, perfluorocyclobutadiene, phenyl perfluoroethylene, a -methyl-phenyl difluoroethylene and perfluoroacrylonitrile; tetrafluoroethylene with chlorotrifluoroethylene and trichloroethylene or sym.-dichlorodifluoroethylene with chlorotrifluoroethylene or tetrafluoroethylene. The preferred catalyst is benzoyl peroxide activated with sulphur dioxide, but dichlorobenzoyl, di-t-butyl and trichloracetyl peroxides, tetraethyl lead, oxygen and sunlight may be used. The sulphuryl halide may be sulphuryl chloride, bromide or fluoride, fluorosulphuryl chloride or bromosulphuryl chloride. The process may be carried out batchwise, using an inert solvent such as carbon tetrachloride, tetrachlorethylene, tetrachlorethane and 1,2,2-trifluorotrichlorethane if desired, under autogenous pressure, or continuously. The products may be purified by heating to remove excess sulphuryl chloride, solvent and monomer, treating with silica gel, alumina or activated carbon and washed with aqueous ammonia or alkali to remove acids and then fractionally distilled. The liquid, greasy or waxy products may be used as lubricants, hydraulic fluids, heat-transfer media, dielectric fluids, potting compounds, rubber softeners and plasticizers, e.g. for polytetrafluorethylene and polychlorotrifluorethylene. The properties of polychlorotrifluorethylene plasticized with various fractional distillates of its telomer are tabulated.ALSO:Distillable telomers of the formula W-(X)n -W or W-(X, Y)n-W, where W is chlorine, bromine or fluorine, X and Y are halo-olefinic monomers and n is greater than 1, are made by telomerizing the monomer or monomers under anhydrous conditions with a sulphuryl halide in the presence of a polymerization catalyst. Suitable monomers are vinyl chloride, bromide and fluoride, vinylidene chloride and fluoride, 2-chloropropene, a -chloro- and bromo-styrenes, trifluoroethylene, tetrafluoroethylene, tetrachloropropene, chlorotrifluoroethylene, bromotrifluoroethylene, unsym.-dibromodifluoro- and dichlorodifluoro-ethylenes, chlorobutadiene, perfluorobutadiene, perfluorocyclobutene, perfluorocyclobutadiene, phenyl perfluoroethylene, a -methyl-phenyl difluoroethylene and perfluoroacrylonitrile; tetrafluoroethylene with chlorotrifluoro-ethylene and trichloroethylene or sym.-dichlorodifluoroethylene with chlorotrifluoroethylene or tetrafluoroethylene. The preferred catalyst is benzoyl peroxide activated with sulphur dioxide, but dichlorobenzoyl, di-t-butyl and trichloracetyl peroxides, tetraethyl lead, oxygen and sunlight may be used. The sulphuryl halide may be sulphuryl chloride, bromide or fluoride, fluorosulphuryl chloride or bromosulphuryl chloride. The process may be carried out batchwise, using an inert solvent such as carbon tetrachloride, tetrachlorethylene, tetrachlorethane and 1,2,2 - trifluorotrichlorethane if desired, under autogenous pressure or continuously. The products may be purified by heating to remove excess sulphuryl chloride, solvent and monomer, treating with silica gel, alumina or activated carbon and washed with aqueous ammonia or alkali to remove acids and then fractionally distilled. The liquid, greasy or waxy products may be used as lubricants, hydraulic fluids, heat-transfer media, dielectric fluids, potting compounds, rubber softeners and plasticizers. The physical properties of the four-carbon (C4Cl4F6) or six-carbon (C6Cl5F9) chlorotrifluoroethylene telomers are given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US744256XA | 1952-06-19 | 1952-06-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB744256A true GB744256A (en) | 1956-02-01 |
Family
ID=22119494
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12880/53A Expired GB744256A (en) | 1952-06-19 | 1953-05-08 | Improvements in or relating to telomerization process |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE954644C (en) |
GB (1) | GB744256A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1115873B (en) * | 1957-03-20 | 1961-10-26 | Minnesota Mining & Mfg | Damping and gyroscopic fluid |
-
1953
- 1953-05-08 GB GB12880/53A patent/GB744256A/en not_active Expired
- 1953-05-27 DE DEK18220A patent/DE954644C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1115873B (en) * | 1957-03-20 | 1961-10-26 | Minnesota Mining & Mfg | Damping and gyroscopic fluid |
Also Published As
Publication number | Publication date |
---|---|
DE954644C (en) | 1956-12-20 |
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