GB868494A - Process for making fluorinated organic compounds - Google Patents

Process for making fluorinated organic compounds

Info

Publication number
GB868494A
GB868494A GB30568/57A GB3056857A GB868494A GB 868494 A GB868494 A GB 868494A GB 30568/57 A GB30568/57 A GB 30568/57A GB 3056857 A GB3056857 A GB 3056857A GB 868494 A GB868494 A GB 868494A
Authority
GB
United Kingdom
Prior art keywords
radical
cf2cf
atom
fluorine
perfluoroalkyl
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
GB30568/57A
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.)
Pennwalt Corp
Original Assignee
Pennsalt Chemical Corp
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 Pennsalt Chemical Corp filed Critical Pennsalt Chemical Corp
Publication of GB868494A publication Critical patent/GB868494A/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
    • C07C17/093—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
    • C07C17/26—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
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/14—Acyclic saturated compounds containing halogen atoms containing fluorine and bromine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/16—Acyclic saturated compounds containing halogen atoms containing fluorine and iodine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/02—Monocyclic halogenated hydrocarbons
    • C07C23/06—Monocyclic halogenated hydrocarbons with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/18—Polycyclic halogenated hydrocarbons
    • 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
    • C08F14/00—Homopolymers and 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
    • C08F14/18—Monomers containing fluorine
    • C08F14/185—Monomers containing fluorine not covered by the groups C08F14/20 - C08F14/28
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/02—Halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or 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; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/18—Homopolymers or copolymers or tetrafluoroethene

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)

Abstract

Polytetrafluoroethylene is plasticized with compounds boiling above 100 DEG C. at atmospheric pressure and having the formula Rc[CF2CF (CF3)]nX where n is an integer from 3 to 20, Rc is perfluoroalkyl or perfluorochloroalkyl and X is F, Cl or Rc[CF2CF(CF3)]n, preferred compounds being C3F7[CF2CF(CF3)]nCl, C3F7 [CF2CF(CF3)]nF and <FORM:0868494/IV (a)/1> Specification 774,103 is referred to.ALSO:Organic fluorinated telomers are produced by heating at a temperature from 150 DEG to 350 DEG C. a telogen of the formula RQ with at least an equimolar portion of an unsaturated fluorinated difficultly polymerizable compound such as perfluoropropene, 2,3,3,3-tetrafluoropropene-1, perfluorocyclobutene and perfluorobutadiene for a sufficient length of time to form telomers having at least three units corresponding to the unsaturated compound in the telomer chain, Q representing bromine or iodine and R representing (a) a perfluoroalkyl, perfluorocycloalkyl or perfluoroalkenyl radical; (b) a perfluorochloroalkyl, perfluorochlorocycloalkyl, perfluorohydrocycloalkyl, perfluorochloroalkenyl or perfluorohydroalkenyl radical in which the carbon atom attached to Q is attached to at least one fluorine atom, a perfluoroalkyl radical or a R11CF2-radical where R11 is a perfluorochloroalkyl or perfluorohydroalkyl radical; or (c) an R1CXY-group where R1 is (i) fluorine, (ii) an alkyl, aryl or aralkyl radical or (iii) a halogenoalkyl, halogenoaryl or halogenoaralkyl radical containing not more than one iodine atom, where X is a fluorine or hydrogen atom or a perfluoroalkyl or R11CF2-radical containing up to 5 carbon atoms, and where Y is a fluorine, chlorine or bromine atom or a perfluoroalkyl or R11CF2-radical containing up to five carbon atoms, but where, if R is chlorine or bromine R1 is a fluorine atom or a halogenoalkyl or halogenoaralkyl radical in which there is not more than one iodine atom and in which the carbon atom linked to the -CXY-group has two substituents selected from fluorine, chlorine, perfluoroalkyl radicals containing not more than five carbon atoms, and R11CF2 radicals containing not more than five carbon atoms and has not more than one chlorine atom attached to it. Typical telogens are iodotrifluoromethane, 1-iodoperfluoropropane and 2-iodoperfluorohexane. The Specification contains lists of suitable telogens and unsaturated compounds. The telogen may be formed in situ by reaction of the unsaturated compound with iodine, bromine or iodine monochloride. The Q atom (bromine or iodine) of the product may be replaced with chlorine or fluorine by conventional methods, e.g. treatment with chlorine or cobalt trifluoride. The product of the process of the invention has the formula R(U)nQ where U designates the fluorinated unsaturated difficultly polymerizable compound and n is an integer, typical products being CF3[CF2CF(CF3)]nQ, C3F7[CF2CF(CF3)]nQ, C4F9CF(CF3)[CF2CF (CF3)]nQ, and CF2ClCFCl[CF2CF(CF3)]nQ. Specification 774,103 is referred to.
GB30568/57A 1956-10-09 1957-09-30 Process for making fluorinated organic compounds Expired GB868494A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US868494XA 1956-10-09 1956-10-09

Publications (1)

Publication Number Publication Date
GB868494A true GB868494A (en) 1961-05-17

Family

ID=22201305

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30568/57A Expired GB868494A (en) 1956-10-09 1957-09-30 Process for making fluorinated organic compounds

Country Status (2)

Country Link
FR (1) FR1223259A (en)
GB (1) GB868494A (en)

Also Published As

Publication number Publication date
FR1223259A (en) 1960-06-16

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