GB798407A - Preparation of hexafluorobutadiene - Google Patents

Preparation of hexafluorobutadiene

Info

Publication number
GB798407A
GB798407A GB3627656A GB3627656A GB798407A GB 798407 A GB798407 A GB 798407A GB 3627656 A GB3627656 A GB 3627656A GB 3627656 A GB3627656 A GB 3627656A GB 798407 A GB798407 A GB 798407A
Authority
GB
United Kingdom
Prior art keywords
cfcl
hexafluoro
butadiene
cfcl2
tetrachloro
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
Application number
GB3627656A
Inventor
Robert Palmer Ruh
Ralph Anderson Davis
Keith Adair Allswede
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Priority to GB3627656A priority Critical patent/GB798407A/en
Publication of GB798407A publication Critical patent/GB798407A/en
Expired legal-status Critical Current

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
    • C07C17/20—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
    • C07C17/208—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 MX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • 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
    • C07C21/19—Halogenated dienes
    • C07C21/20—Halogenated butadienes

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

Hexafluoro-1,3-butadiene is prepared by heating 1,2 - dichloro - 1,2 - difluoroethylene in a closed vessel at a temperature in the range 100 DEG to 400 DEG C. for a time sufficiently long to form 1,3,4,4 - tetrachloro - 1,2,3,4 - tetrafluorobutene-1, chlorinating this to 1,1,2,3,4,4-hexachloro - 1,2,3,4 - tetrafluorobutane, fluorinating this to 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane and dechlorinating this latter compound to hexafluoro-1,3-butadiene with zinc in the presence of a lower alkanol having less than 6 carbon atoms per molecule. In the above process an antimony fluorohalide, antimony fluoride and chlorine or hydrofluoric acid in the presence of a vapour phase fluorination catalyst, such as chromium fluoride may be used as fluorinating agents, whilst gaseous chlorine in the presence of actinic light may be used as a chlorinating agent; also the conversion of 1,2,3,4 - tetrachloro - 1,1,2,3,4,4 - hexafluorobutane to hexafluoro-1,3-butadiene is carried out under essentially anhydrous conditions. An example describes the preparation of hexafluoro - 1,3 - butadiene wherein a mixture of cis- and trans-1,2-dichloro-1,2-difluoroethylenes, boiling at about 22 DEG C., is heated under pressure to form a mixture from which the dimer CFCl=CF-CFCl-CFCl2 is separated by fractional distillation. The dimer is chlorinated by gaseous chlorine in direct sunlight to form CFCl2-CFCl-CFCl-CFCl2 which is again fractionally distilled and then heated with SbF3Cl2 to form a mixture of fluorinated chlorohydrocarbons C4ClF9, C4Cl2F8, C4Cl3F7, C4Cl4F6, C4Cl5F5. The C4Cl4F6 fraction is heated with powdered zinc in absolute ethanol when gaseous CF2=CF-CF=CF2 is evolved and condensed.
GB3627656A 1956-11-27 1956-11-27 Preparation of hexafluorobutadiene Expired GB798407A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3627656A GB798407A (en) 1956-11-27 1956-11-27 Preparation of hexafluorobutadiene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3627656A GB798407A (en) 1956-11-27 1956-11-27 Preparation of hexafluorobutadiene

Publications (1)

Publication Number Publication Date
GB798407A true GB798407A (en) 1958-07-23

Family

ID=10386633

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3627656A Expired GB798407A (en) 1956-11-27 1956-11-27 Preparation of hexafluorobutadiene

Country Status (1)

Country Link
GB (1) GB798407A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10336669B2 (en) 2016-04-04 2019-07-02 Arkema France Method for preparing hexafluorobutadiene
US10351493B2 (en) 2016-04-04 2019-07-16 Arkema France Method for preparing polyunsaturated perfluorinated compounds
US11192838B2 (en) 2017-05-22 2021-12-07 Showa Denko K.K. Production method for hexafluoro-1,3-butadiene

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10336669B2 (en) 2016-04-04 2019-07-02 Arkema France Method for preparing hexafluorobutadiene
US10351493B2 (en) 2016-04-04 2019-07-16 Arkema France Method for preparing polyunsaturated perfluorinated compounds
US11192838B2 (en) 2017-05-22 2021-12-07 Showa Denko K.K. Production method for hexafluoro-1,3-butadiene

Similar Documents

Publication Publication Date Title
US2885427A (en) Fluorination of trichloroethylene
Haszeldine 716. Addition of free radicals to unsaturated systems. Part V. The direction of addition to 1: 1-difluoroprop-1-ene, 3: 3: 3-trifluoro-2-trifluoromethylprop-1-ene, and 3-chloro-3: 3-difluoro-2-trifluoromethylprop-1-ene
Tarrant et al. Free Radical Additions Involving Fluorine Compounds. IV. The Addition of Dibromodifluoromethane to Some Fluoroölefins1
Henne et al. Ionization constants of fluorinated acids. III. Unsaturated acids
US2739987A (en) Production of fluorine-substituted
Haszeldine 550. Reactions of fluorocarbon radicals. Part V. Alternative syntheses for trifluoromethylacetylene (3: 3: 3-trifluoropropyne), and the influence of polyfluoro-groups on adjacent hydrogen and halogen atoms
Henne et al. The Preparation and Directed Chlorination of 1, 1, 1-Trifluoropropane
US3024290A (en) Process for replacing vinylic halogens with fluorine
US3287425A (en) Fluorinated compounds and their preparation
GB798407A (en) Preparation of hexafluorobutadiene
US4078007A (en) Fluorine substitution in 1,1,1-trihalomethanes
Haszeldine et al. 540. Addition of free radicals to unsaturated systems. Part XIV. The direction of radical addition to trifluoroethylene
US2566807A (en) Method of preparing chlorofluoroethylenes
US4138355A (en) Fluorine substitution in 1,1,1-trihalomethanes
GB938070A (en) New fluorination process
US2921099A (en) Process for the preparation of bromochlorofluoroethanes
US2404706A (en) Fluorination
US2959624A (en) Process for preparing 1, 1, 1-trifluoro-2-chloro-2-bromethane from 1, 1, 2-trifluoro-1-bromo-2-chlorethane
Fried et al. Substitution and Addition Reactions of the Fluoroölefins. III. 1 SN2'Substitution Reactions of Chlorofluoroallyl Chlorides with Halide Ions2
GB1013991A (en) Separation of fluorinated compounds
US2724004A (en) Preparation of 1, 1-difluoro-1, 2, 2-trichloroethane
USRE23425E (en) Polyfluorinated compounds
NO123589B (en)
GB466509A (en) Manufacture of fluorine compounds of aliphatic hydrocarbons
Fuller et al. 626. Some isomeric hexafluorocyclobutanes and pentafluorocyclobutenes