GB904263A - Perfluoroalkyl alkanols - Google Patents

Perfluoroalkyl alkanols

Info

Publication number
GB904263A
GB904263A GB1628462A GB1628462A GB904263A GB 904263 A GB904263 A GB 904263A GB 1628462 A GB1628462 A GB 1628462A GB 1628462 A GB1628462 A GB 1628462A GB 904263 A GB904263 A GB 904263A
Authority
GB
United Kingdom
Prior art keywords
perfluorooctyl
reduced
give
acid
alcohol
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
GB1628462A
Inventor
Arthur H Ahlbrecht
Samuel Smith
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
Priority to GB1628462A priority Critical patent/GB904263A/en
Publication of GB904263A publication Critical patent/GB904263A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/22—Esters containing halogen
    • C08F20/24—Esters containing halogen containing perhaloalkyl radicals

Landscapes

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

Abstract

The invention comprises the compounds Rf(CH2)mOH, where Rf is a perfluoroalkyl radical having 3-12 carbon atoms and m is 3-12. These compounds may be prepared by the desulphonylative addition of a perfluoroalkane sulphonyl halide to a terminally unsaturated alcohol, esterified alcohol, or carboxylic acid, followed by reductive dehalogenation to replace halogen by chlorine, and hydrolysis if an esterified alcohol was used or reduction if an acid was used. In Examples, (1) C8F17SO2Cl is reacted with 4-pentenoic acid to give 4-chloro-5-(perfluorooctyl)-pentanoic acid, which is hydrogenated to 5-perfluorooctyl pentanoic acid, and this is reduced to 5-perfluorooctyl-pentanol; (2) C8F17SO2Cl is reacted with alkyl acetate to give 2-chloro-3-(perfluorooctyl) propyl acetate, which is dehydrohalogenated to 3-(perfluorooctyl) alkyl alcohol, and this is reduced to 3-(perfluorooctyl) propanol; (3) ethyl perfluorobutyrate is condensed with methyl acetate to give C3F7COCH2COOCH3, this is reduced to C3F7CHOHCH2COOCH3, which is dehydrated to C3F7CH:CHCOOCH3; this is hydrogenated to the saturated ester, which is reduced to C3F7(CH2)3OH.
GB1628462A 1958-08-11 1958-08-11 Perfluoroalkyl alkanols Expired GB904263A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1628462A GB904263A (en) 1958-08-11 1958-08-11 Perfluoroalkyl alkanols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1628462A GB904263A (en) 1958-08-11 1958-08-11 Perfluoroalkyl alkanols

Publications (1)

Publication Number Publication Date
GB904263A true GB904263A (en) 1962-08-29

Family

ID=10074548

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1628462A Expired GB904263A (en) 1958-08-11 1958-08-11 Perfluoroalkyl alkanols

Country Status (1)

Country Link
GB (1) GB904263A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1214660B (en) * 1963-10-09 1966-04-21 Du Pont Process for the preparation of fluoroalkanols
US4098806A (en) * 1976-03-05 1978-07-04 Produits Chimiques Ugine Kuhlmann Process for functionalizing perfluorohalogenoalkanes
US5852148A (en) * 1991-07-10 1998-12-22 Minnesota Mining & Manufacturing Company Perfluoroalkyl halides and derivatives
US6048952A (en) * 1991-07-10 2000-04-11 3M Innovative Properties Company Perfluoroalkyl halides and derivatives
WO2001058833A1 (en) * 2000-02-11 2001-08-16 Rhodia Chimie Method for functionalising a double bond

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1214660B (en) * 1963-10-09 1966-04-21 Du Pont Process for the preparation of fluoroalkanols
US4098806A (en) * 1976-03-05 1978-07-04 Produits Chimiques Ugine Kuhlmann Process for functionalizing perfluorohalogenoalkanes
US5852148A (en) * 1991-07-10 1998-12-22 Minnesota Mining & Manufacturing Company Perfluoroalkyl halides and derivatives
US6048952A (en) * 1991-07-10 2000-04-11 3M Innovative Properties Company Perfluoroalkyl halides and derivatives
US6365769B1 (en) 1991-07-10 2002-04-02 3M Innovative Properties Company Perfluoroalkyl halides and derivatives
WO2001058833A1 (en) * 2000-02-11 2001-08-16 Rhodia Chimie Method for functionalising a double bond

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