GB1019788A - Process for the production of fluorinated carbonyl compounds - Google Patents

Process for the production of fluorinated carbonyl compounds

Info

Publication number
GB1019788A
GB1019788A GB4396464A GB4396464A GB1019788A GB 1019788 A GB1019788 A GB 1019788A GB 4396464 A GB4396464 A GB 4396464A GB 4396464 A GB4396464 A GB 4396464A GB 1019788 A GB1019788 A GB 1019788A
Authority
GB
United Kingdom
Prior art keywords
oxide
gives
fluoride
carbonyl
omega
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
GB4396464A
Inventor
Earl Phillip Moore
Alwin S Milian
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to GB4396464A priority Critical patent/GB1019788A/en
Publication of GB1019788A publication Critical patent/GB1019788A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • 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
    • C07C49/167—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/457—Saturated compounds containing a keto group being part of a ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/457—Saturated compounds containing a keto group being part of a ring containing halogen
    • C07C49/463—Saturated compounds containing a keto group being part of a ring containing halogen a keto group being part of a six-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Fluorinated carbonyl compounds are obtained by isomerizing a compound <FORM:1019788/C2/1> where Rf1, Rf2 and Rf3 are fluorine atoms or C1- 8 perfluoroalkyl or omega-hydroperfluoroalkyl radicals, or two together make up a C2- 8 perfluoroalkylene radical, by contact with a catalyst consisting of an acidic metal oxide, a chloride, bromide, iodide, oxychloride or oxybromide of a polyvalent metal having a valency less than its maximum co-ordination number, a transition metal carbonyl, a compound producing fluoride ions in the presence of the epoxide, a tertiary amine, a tertiary amine oxide or a tertiary amide. Depending on whether an acidic or a basic catalyst is used, the following type of reaction may occur: <FORM:1019788/C2/2> where the Rf radicals are C1- 8 perfluoroalkyl or omega-hydroperfluoroalkyl. Specified catalysts are Al2O3, TiO2, WO2; AlCl3, AlBr3, SnCl4, VOCl3, TiCl4, FeCl3, CuCl2, ZrOCl2; tungsten carbonyl, iron carbonyl; KF, KHF2, C5F, PF5, SF4, BF3 etherate, alkali metal carbonates, alkali and alkaline earth metal hydroxides, reduced transition metal oxides; trimethylamine, triethylamine, dimethylaniline, pyridine; pyridine N-oxide, trimethylamine N-oxide; dimethylformamide, dimethylacetamide and diethylbenzamide. Solvents may be used. In examples, hexafluoropropylene oxide gives hexafluoroacetone, with or without pentafluoropropionyl fluoride; perfluorocyclopentene oxide gives perfluorocyclopentanone; omega-hydro-perfluorohept-1-ene oxide gives H(CF2)6COF or H(CF2)5COCF3; tetrafluoroethylene oxide gives perfluoroacetyl fluoride; perfluoroisobutylene oxide gives perfluoroisobutyryl fluoride and (CF3)2CFCF2OC(CF3)2COF; and perfluorocyclohexene oxide gives perfluorocyclohexanone. Perfluorocyclopentene and perfluorocyclohexene (from KF and hexafluorodichlorocyclopentene, or 1,2-dichloroperfluorocyclohex-1-ene or 1,2,4,4,5,5 - hexachloro - 3,3,6,6 - tetrafluorocyclohex-1-ene respectively, in the presence of N-methylpyrrolidone) are converted to the epoxides with methanolic alkaline H2O2, and unreacted olefin removed.
GB4396464A 1964-10-28 1964-10-28 Process for the production of fluorinated carbonyl compounds Expired GB1019788A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4396464A GB1019788A (en) 1964-10-28 1964-10-28 Process for the production of fluorinated carbonyl compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4396464A GB1019788A (en) 1964-10-28 1964-10-28 Process for the production of fluorinated carbonyl compounds

Publications (1)

Publication Number Publication Date
GB1019788A true GB1019788A (en) 1966-02-09

Family

ID=10431154

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4396464A Expired GB1019788A (en) 1964-10-28 1964-10-28 Process for the production of fluorinated carbonyl compounds

Country Status (1)

Country Link
GB (1) GB1019788A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109503423A (en) * 2018-11-30 2019-03-22 天津市长芦化工新材料有限公司 Hexafluoropropylene dimmer prepares the method and perfluor isobutyronitrile and application of perfluor isobutyronitrile
CN112957648A (en) * 2021-01-28 2021-06-15 深圳供电局有限公司 Fluorine-containing fire extinguishing agent and preparation method and application thereof
CN113634263A (en) * 2021-06-16 2021-11-12 浙江诺亚氟化工有限公司 Perfluoroolefin epoxidation catalyst and application thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109503423A (en) * 2018-11-30 2019-03-22 天津市长芦化工新材料有限公司 Hexafluoropropylene dimmer prepares the method and perfluor isobutyronitrile and application of perfluor isobutyronitrile
CN112957648A (en) * 2021-01-28 2021-06-15 深圳供电局有限公司 Fluorine-containing fire extinguishing agent and preparation method and application thereof
CN113634263A (en) * 2021-06-16 2021-11-12 浙江诺亚氟化工有限公司 Perfluoroolefin epoxidation catalyst and application thereof
CN113634263B (en) * 2021-06-16 2023-04-25 浙江诺亚氟化工有限公司 Perfluoro olefin epoxidation catalyst and application thereof

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