WO2018079727A1 - Procédé de production de 2,3,3,3-tétrafluoropropène - Google Patents

Procédé de production de 2,3,3,3-tétrafluoropropène Download PDF

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Publication number
WO2018079727A1
WO2018079727A1 PCT/JP2017/038956 JP2017038956W WO2018079727A1 WO 2018079727 A1 WO2018079727 A1 WO 2018079727A1 JP 2017038956 W JP2017038956 W JP 2017038956W WO 2018079727 A1 WO2018079727 A1 WO 2018079727A1
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WIPO (PCT)
Prior art keywords
catalyst
fluoride
metal
reactor
tetrafluoropropene
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Application number
PCT/JP2017/038956
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English (en)
Japanese (ja)
Inventor
達也 鎌塚
優 竹内
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旭硝子株式会社
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Publication of WO2018079727A1 publication Critical patent/WO2018079727A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • reaction (a) In the reaction that occurs when the fluorinated propane (1) is brought into contact with the catalyst (C1), the fluorinated propane (1) is removed by XY (HCl or HF) mainly by a two-stage reaction represented by the following formula (a). 1233yf is produced (indicated by “reaction (a-1)” in formula (a)), and then the chlorine atom at the 3-position of 1233yf is substituted with a fluorine atom to produce 1234yf (in formula (a), “Reaction (a-2)”).
  • 1234yf can be obtained by using the catalyst (C1) without particularly introducing HF into the reaction system. Can be manufactured efficiently. In this case, 1234yf may be produced while introducing HF into the reaction system.
  • the metal compound contained in the catalyst (C2) may be composed of only one kind or two or more kinds.
  • the catalyst (C2) may contain a catalyst or impurities other than the above metal compound as long as the effects of the present invention are not impaired.
  • the catalyst (C) may be used by being supported on a carrier.
  • the carrier include carbon materials such as activated carbon, carbon black, and carbon fiber, and oxide materials such as alumina, silica, titania, zirconia, alkali metal oxides, and alkaline earth metal oxides. Silica, zirconia, alkali metal oxides and alkaline earth metal oxides are preferred. Among these, activated carbon, alumina, and zirconia are particularly preferable because they have a large specific surface area and can easily carry the catalyst.
  • the specific surface area of the catalyst or catalyst pellet depends on the type of each catalyst. Generally, the smaller the value, the lower the conversion rate, and the larger the value, the lower the selectivity and the faster the deterioration.
  • the reaction shown in a) is hardly affected.
  • the specific surface area of the metal oxide catalyst and the metal oxide partial halide catalyst is preferably 10 to 400 m 2 / g, and the specific surface area of the metal halide catalyst is preferably 3 to 300 m 2 / g. .
  • it depends on the specific surface area of the binder, so it cannot be said unconditionally.
  • HCFC-22, HFC-23, and hydrogen fluoride are more preferable, and HFC-23 is particularly preferable.
  • fluorine-containing propane (1) such as 244cc which is a raw material, as an activation processing agent.
  • the catalyst can be reactivated in the reaction system, and the decrease in the activity of the catalyst can be suppressed.
  • the reactivation treatment agent is supplied to the fluorine-containing propane (1) supplied to the reactor (however, when a composition containing the fluorine-containing propane (1) is used as a raw material, 0.001 to 1000 mol% is preferred. From the viewpoint of enhancing the reactivation effect of the catalyst, 0.01 mol% or more is more preferable, 0.05% or more is more preferable, and 0.1% or more is particularly preferable. From the viewpoint of improving the volumetric efficiency of the reactor and reducing impurities derived from the reactivation treatment agent, it is preferably 100 mol% or less, more preferably 10 mol% or less, and particularly preferably 1 mol% or less.
  • the production method (I) When the production method (I) is carried out in the gas phase, it can be carried out by a method in which 244 cc of fluorinated propane (1) is allowed to flow through the reactor containing the catalyst (C1) for a predetermined time.
  • there is an advantage that the durability of the catalyst is improved by using a dilution gas.
  • the amount of the dilution gas is not particularly limited, but specifically, it is 1 to 244 cc supplied to the reactor (however, when a composition containing 244 cc is used as a raw material) An amount of 10,000 mol%, preferably 10 to 1000 mol%, more preferably 30 to 500 mol% can be mentioned. Dilution gas may be used individually by 1 type, and may use 2 or more types together.
  • the reactor used in the production method (I) is not particularly limited as long as it can withstand the temperature and pressure in the reactor described above.
  • a glass flask, an autoclave, or a cylindrical vertical reactor is used. be able to.
  • the material of the reactor glass, iron, nickel, iron, an alloy containing nickel as a main component, or the like is used.
  • the reactor may be provided with an electric heater for heating the inside of the reactor.
  • 1233yf can be used as a raw material of the manufacturing method of 1234yf of the 2nd aspect of this invention demonstrated below.
  • anhydrous aluminum chloride 25 g, 0.19 mol
  • CHCl 3 500 g, 4.19 mol
  • 224ca 100 g, 0.45 mol
  • a catalyst comprising a catalyst layer in the reactor in the same manner as the preparation of the catalyst (cf1) except that zinc oxide was changed to aluminum oxide (Al 2 O 3 , manufactured by JGC Catalysts & Chemicals) cf2) was obtained.
  • the outlet gas after dehydration was captured in a cylinder cooled with dry ice.
  • the trapped outlet gas is used as a sample and supplied to the bottom of a distillation column having a theoretical plate number of about 45.
  • Distillation is performed by batch distillation at an operating pressure of 0.8 MPa (gauge pressure), and 1234yf from the top of the distillation column. A distillate containing 99.8% was obtained.

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

Abstract

L'invention concerne un procédé de production efficace de 2,3,3,3-tétrafluoropropène à partir de matières premières facilement accessibles par une opération de réaction simple à l'aide d'un catalyseur sûr et économique mais hautement actif. Un procédé de production de 2,3,3,3-tétrafluoropropène dans lequel du 2,3,3,3-tétrafluoropropène est obtenu par la mise en contact d'un propane contenant du fluor représenté par la formule générale (1) (CF 2 Cl-CFX-CH 2 Y, dans laquelle l'un de X et Y est H et l'autre est F ou Cl) avec un catalyseur qui comprend un fluorure de métal qui comprend au moins un fluorure d'un métal choisi parmi les métaux alcalins, les métaux alcalino-terreux, l'aluminium et le zirconium (à condition que, lorsque l'un de X et Y dans la formule générale (1) est H et l'autre est Cl, le propane contenant du fluor est mis en contact avec le catalyseur qui comprend le fluorure de métal en présence de fluorure d'hydrogène).
PCT/JP2017/038956 2016-10-28 2017-10-27 Procédé de production de 2,3,3,3-tétrafluoropropène WO2018079727A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016211686 2016-10-28
JP2016-211686 2016-10-28

Publications (1)

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WO2018079727A1 true WO2018079727A1 (fr) 2018-05-03

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009148191A1 (fr) * 2008-06-05 2009-12-10 Daikin Industries, Ltd. Procédé de fabrication d'un composé contenant du fluor par réaction de réarrangement
JP2011529448A (ja) * 2008-07-30 2011-12-08 ダイキン工業株式会社 ２，３，３，３−テトラフルオロプロペンの製法
JP2012526043A (ja) * 2009-05-12 2012-10-25 ダイキン工業株式会社 含フッ素プロパンの製造方法
JP2016132648A (ja) * 2015-01-21 2016-07-25 ダイキン工業株式会社 フルオロプロペンの製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009148191A1 (fr) * 2008-06-05 2009-12-10 Daikin Industries, Ltd. Procédé de fabrication d'un composé contenant du fluor par réaction de réarrangement
JP2011529448A (ja) * 2008-07-30 2011-12-08 ダイキン工業株式会社 ２，３，３，３−テトラフルオロプロペンの製法
JP2012526043A (ja) * 2009-05-12 2012-10-25 ダイキン工業株式会社 含フッ素プロパンの製造方法
JP2016132648A (ja) * 2015-01-21 2016-07-25 ダイキン工業株式会社 フルオロプロペンの製造方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BURGIN, MARIA 0. ET AL.: "Unimolecular reaction kinetics of CF2ClCF2 CH 3 and CF2ClCF2 CD 3: Experimental evidence for a Novel 1, 2-FC1 Rearrangement pathway", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 105, 2001, pages 1615 - 1621, XP002448571, DOI: doi:10.1021/jp002511d *
HEARD, GEORGE L. ET AL.: "1, 2-FC1 Rearragement as an Intermediate step in the unimolecular 1,3-HCl elimination from chlorofluoropropanes", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 105, 2001, pages 1622 - 1625, XP055416203, DOI: doi:10.1021/jp0025126 *
HENNE, ALBERT L. ET AL.: "Fluorinated Derivatives of Propane and Propylene . VI", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 68, 1946, pages 496 - 497, XP002448570, DOI: doi:10.1021/ja01207a041 *

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