GB589167A - Improvements in or relating to the production of fluorinated derivatives of aliphatic hydrocarbons - Google Patents

Improvements in or relating to the production of fluorinated derivatives of aliphatic hydrocarbons

Info

Publication number
GB589167A
GB589167A GB664845A GB664845A GB589167A GB 589167 A GB589167 A GB 589167A GB 664845 A GB664845 A GB 664845A GB 664845 A GB664845 A GB 664845A GB 589167 A GB589167 A GB 589167A
Authority
GB
United Kingdom
Prior art keywords
hydrogen fluoride
fluorine
prepared
fluorinating agent
halogen
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
GB664845A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB664845A priority Critical patent/GB589167A/en
Publication of GB589167A publication Critical patent/GB589167A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/093Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/208Preparation 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

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

Antimony halo-fluorides, used as fluorinating agents in reaction with halogenated aliphatic hydrocarbons to yield hydrocarbon having three fluorine atoms attached to one carbon atom (see Group IV), are prepared by reacting anhydrous hydrogen fluoride with an antimony pentahalide not containing fluorine, the amount of hydrogen fluoride present being at least equivalent to that required to convert the whole of the pentahalide to the pentafluoride. The compounds have a composition represented by the general formula SbFn x5-n + (5-n) HF where X is a halogen other than fluorine and n, which is an integer not less than 3, represents the number of halogen atoms replaced by fluorine. Preferably, the process is carried out in a closed vessel at temperatures rising to 125 DEG C. or higher under the corresponding antogenic pressures. In example (1), 600 parts by weight of antimony pentachloride and 200 parts of anhydrous hydrogen fluoride are heated in an autoclave for four hours, the temperature and pressure being 130 DEG C. and 900-1,000 lbs. yielding a compound of the composition SbF3Cl2.2HF.ALSO:Fluorinated aliphatic hydrocarbons or halohydrocarbons, in which three fluorine atoms are attached to one carbon atom and which may or may not contain further fluorine atoms attached to other carbon atoms and other halogens, are prepared by reacting in a closed vessel, a halogenated aliphatic hydrocarbon containing at least three halogen atoms in the molecule and having three halogen atoms, at least one of which is a halogen other than fluorine attached to one carbon atom, at a temperature of at least 30 DEG C. and at the corresponding autogenic pressure, with a fluorinating agent obtained by reacting anhydrous hydrogen fluoride with an antimony pentahalide not containing fluorine, the amount of hydrogen fluoride present being at least equivalent to that required to convert the whole of the antimony pentahalide to the pentafluoride; the fluorinating agent has the composition SbFnX5-n+(5 - n)HF, where X is halogen other than fluorine and n, an integer not less than 3, is the number of atoms of halogen in the original pentahalide replaced by fluorine. Preferably, an antimony pentahalide containing halogen other than fluorine is reacted in an autoclave with anhydrous hydrogen fluoride in an amount equivalent to at least 5 moles per mole. of pentahalide at a temperature of at least 125 DEG C., suitably 150 DEG C., then the autoclave is vented to remove hydrogen chloride liberated in the reaction and the material to be fluorinated, say dichloro difluoromethane, is charged into the autoclave which is again heated to about 160 DEG C. The autoclave is cooled, excess pressure released and the gaseous reaction products scrubbed to remove traces of acid. The spent fluorinating agent may be regenerated by adding thereto an amount of anhydrous hydrogen fluoride equivalent to that consumed in the previous fluorination and then heating as described above. In this manner alternate regenerations and fluorinations may be carried out or the two operations may be combined. Accordingly, a continuous process may be effected by adding hydrogen fluoride and halohydrocarbon continuously while withdrawing the fluorinated product. In examples: (1) monochlorotrifluoromethane was prepared by reaction of dichloro-difluoromethane and a fluorinating agent of the composition SbF3Cl2.2HF prepared from 600 parts antimony pentachloride and 200 parts anhydrous hydrogen fluoride (see Group III); further batches were prepared by reacting the spent fluorinating agent with a mixture of additional halomethane and an amount of hydrogen fluoride equal to that used in the previous operation or by first regenerating the fluorinating agent and then reacting it with more halomethane; (3) fluoroform was prepared by reacting chloroform with the fluorinating agent described in (1), further batches being prepared by adding chloroform and hydrogen fluoride to the spent agent; (4) fluoroform was prepared as in (2) from monochlorodifluoromethane and hydrogen fluoride, using a spent fluorinating agent prepared as in (1); (5) 1,1,1-trifluoro-2-chloroethane was prepared as in (2) from 1,1-difluoro-1,2-dichloroethane, using as fluorinating agent the product obtained from 600 parts antimony pentachloride and 240 parts hydrogen fluoride. By the process described, methyl chloroform may be converted to methyl fluoroform and carbon tetrachloride to monochlorotrifluoromethane. The trifluoromethanes are useful as refrigerants. Specification 391,168 and U.S.A. Specifications 2,005,705, 2,005,710, 2,024,095, 2,062,743 and 2,230,925 are referred to.
GB664845A 1945-03-16 1945-03-16 Improvements in or relating to the production of fluorinated derivatives of aliphatic hydrocarbons Expired GB589167A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB664845A GB589167A (en) 1945-03-16 1945-03-16 Improvements in or relating to the production of fluorinated derivatives of aliphatic hydrocarbons

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB664845A GB589167A (en) 1945-03-16 1945-03-16 Improvements in or relating to the production of fluorinated derivatives of aliphatic hydrocarbons

Publications (1)

Publication Number Publication Date
GB589167A true GB589167A (en) 1947-06-12

Family

ID=9818263

Family Applications (1)

Application Number Title Priority Date Filing Date
GB664845A Expired GB589167A (en) 1945-03-16 1945-03-16 Improvements in or relating to the production of fluorinated derivatives of aliphatic hydrocarbons

Country Status (1)

Country Link
GB (1) GB589167A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE936090C (en) * 1952-08-02 1955-12-07 Hoechst Ag Process for the preparation of ª ‰ -position fluorinated ethanesulfofluorides
US4851595A (en) * 1987-07-07 1989-07-25 E. I. Du Pont De Nemours And Company Liquid phase halogen exchange process for the manufacture of 1,1,1,2-tetrafluoroethane
US4885416A (en) * 1985-10-18 1989-12-05 E. I. Du Pont De Nemours And Company Fluorination process
EP0414370A1 (en) * 1989-07-24 1991-02-27 E.I. Du Pont De Nemours And Company Halogen-exchange process
US5315046A (en) * 1990-02-26 1994-05-24 Kali-Chemie Ag Process for preparing ethane derivatives
US5608127A (en) * 1990-02-09 1997-03-04 E. I. Dupont De Nemours And Company Halogen exchange process for manufacture of hydrochlorofluoropropanes
US7319175B2 (en) 2001-12-21 2008-01-15 Solvay Fluor Und Derivate Gmbh Catalyst synthesis of halogenated compounds with catalyst regeneration with elemental halogen

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE936090C (en) * 1952-08-02 1955-12-07 Hoechst Ag Process for the preparation of ª ‰ -position fluorinated ethanesulfofluorides
US4885416A (en) * 1985-10-18 1989-12-05 E. I. Du Pont De Nemours And Company Fluorination process
US4851595A (en) * 1987-07-07 1989-07-25 E. I. Du Pont De Nemours And Company Liquid phase halogen exchange process for the manufacture of 1,1,1,2-tetrafluoroethane
EP0414370A1 (en) * 1989-07-24 1991-02-27 E.I. Du Pont De Nemours And Company Halogen-exchange process
US5608127A (en) * 1990-02-09 1997-03-04 E. I. Dupont De Nemours And Company Halogen exchange process for manufacture of hydrochlorofluoropropanes
US5315046A (en) * 1990-02-26 1994-05-24 Kali-Chemie Ag Process for preparing ethane derivatives
US7319175B2 (en) 2001-12-21 2008-01-15 Solvay Fluor Und Derivate Gmbh Catalyst synthesis of halogenated compounds with catalyst regeneration with elemental halogen

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