GB849061A - Improvements in fluorocarbon-radical-containing organic compounds - Google Patents

Improvements in fluorocarbon-radical-containing organic compounds

Info

Publication number
GB849061A
GB849061A GB27394/56A GB2739456A GB849061A GB 849061 A GB849061 A GB 849061A GB 27394/56 A GB27394/56 A GB 27394/56A GB 2739456 A GB2739456 A GB 2739456A GB 849061 A GB849061 A GB 849061A
Authority
GB
United Kingdom
Prior art keywords
chloride
fluorocarbon
product
give
reacts
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
GB27394/56A
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.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing 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 Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of GB849061A publication Critical patent/GB849061A/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
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises fluorocarbon derivatives of the general formula: <FORM:0849061/IV(a)/1> (in which n is an integer up to 50, Rf is a fluorocarbon radical, X is Cl or Br, and the other valencies are satisfied by atoms and/or radicals having combined Hammett sigma (para) parameter values of algebraic sum not greater than +0,4), and a method of preparing these compounds (but without restruction on the value of n) by the action of fluorocarbon sulphonyl chlorides or bromides on the appropriate olefinic compounds containing hydrogen attached to an olefinic carbon atom and free from chainterminating groups, in the presence of a free radical initiator and with liberation of SO2. In an example, reaction of allyl chloride with perfluoromethanesulphonyl chloride at 145 DEG C. in the presence of di-tert.-butyl peroxide yields inter alia a non-volatile telomeric product. It is also stated that the vinyl ester of the product obtained from n-perfluorooctanesulphonyl chloride and 10-hendecenoic acid can be polymerised in the presence of acetyl peroxide to a hard, opaque wax-like product having excellent restance to wetting by both water and oil.ALSO:The invention comprises fluorocarbon derivatives of the general formula: <FORM:0849061/IV(b)/1> (in which n is an integer up to 50, Rf is a fluorocarbon radical, X is Cl or Br, and the other valencies are satisfied by atoms and/or radicals having combined Hammett sigma (para) parameter values of algebraic sum not greater than +0,4, and a method of preparing these compounds (but without restriction on the value of n) by the action of fluorocarbon sulphonyl chlorides or bromides on the appropriate olefinic compounds containing hydrogen attached to an olefine carbon atom and free from chainterminating groups, in the presence of a free radical initiator and with liberation of SO2. In examples, 1-octene reacts with perfluoro-4-ethylcyclo-hexanesulphonyl chloride, to give the product 4-C2F5-c-C6F10CH2.C6CH13 10-hendecenoic acid reacts with perfluo-octanesulphonyl chloride to give C8F17CHCl(CH2)8COOH; cyclohexene reacts with perfluoroctanesulphonyl chloride to give <FORM:0849061/IV(b)/2> allyl chloride reacts with perfluoromethane sulphonyl chloride to give <FORM:0849061/IV(b)/3> as well as the 1 : 1 adduct; a mixture of telomers of higher ratio is also obtained; a list of other perrfluorohydrocarbon sulphonyl chlorides and olefines including hydroxy, acidylamino, keto, carboxylic and ester groups as reactants is given. The free radical initiators include UV light and t.-butyl peroxide; other specified substituents in the olefin include ether, cyclic sulphone, and cyclic ketone groups and an acetylenic alcohol is mentioned. It is also stated that the product from n-perfluoro-octanesulphonyl chloride and 10-hendecenoic acid yields a vinyl ester by mixing it with excess of vinyl acetate in acid solution in the presence of catalytic amounts of mercuric acetate.
GB27394/56A 1955-09-06 1956-09-06 Improvements in fluorocarbon-radical-containing organic compounds Expired GB849061A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US849061XA 1955-09-06 1955-09-06

Publications (1)

Publication Number Publication Date
GB849061A true GB849061A (en) 1960-09-21

Family

ID=22187943

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27394/56A Expired GB849061A (en) 1955-09-06 1956-09-06 Improvements in fluorocarbon-radical-containing organic compounds

Country Status (1)

Country Link
GB (1) GB849061A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0132879A2 (en) * 1983-07-28 1985-02-13 ENICHEM SYNTHESIS S.p.A. Solid lubricant and process for preparing it
US4788012A (en) * 1986-05-28 1988-11-29 Rhone-Poulenc Chimie Process for the preparation of benzyl trifluoromethyl sulfide
WO2001058833A1 (en) * 2000-02-11 2001-08-16 Rhodia Chimie Method for functionalising a double bond
WO2008000680A1 (en) * 2006-06-27 2008-01-03 Clariant International Ltd Fluorous telomeric compounds and polymers containing same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0132879A2 (en) * 1983-07-28 1985-02-13 ENICHEM SYNTHESIS S.p.A. Solid lubricant and process for preparing it
EP0132879A3 (en) * 1983-07-28 1986-11-12 Enichimica Secondaria S.P.A. Solid lubricant and process for preparing it
US4788012A (en) * 1986-05-28 1988-11-29 Rhone-Poulenc Chimie Process for the preparation of benzyl trifluoromethyl sulfide
WO2001058833A1 (en) * 2000-02-11 2001-08-16 Rhodia Chimie Method for functionalising a double bond
WO2008000680A1 (en) * 2006-06-27 2008-01-03 Clariant International Ltd Fluorous telomeric compounds and polymers containing same

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