WO2022014488A1 - Procédé de production de 1-chloro-2,3,3-trifluoropropène - Google Patents

Procédé de production de 1-chloro-2,3,3-trifluoropropène Download PDF

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Publication number
WO2022014488A1
WO2022014488A1 PCT/JP2021/025938 JP2021025938W WO2022014488A1 WO 2022014488 A1 WO2022014488 A1 WO 2022014488A1 JP 2021025938 W JP2021025938 W JP 2021025938W WO 2022014488 A1 WO2022014488 A1 WO 2022014488A1
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reaction
catalyst
chloro
production method
metal compound
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PCT/JP2021/025938
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English (en)
Japanese (ja)
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卓也 岩瀬
厚史 藤森
真理 市野川
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Ａｇｃ株式会社
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Priority to CN202180048922.8A priority Critical patent/CN115803308A/zh
Priority to JP2022536321A priority patent/JPWO2022014488A1/ja
Publication of WO2022014488A1 publication Critical patent/WO2022014488A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/22—Halogenating
    • B01J37/26—Fluorinating
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • 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

Definitions

  • the present invention relates to a method for producing 1-chloro-2,3,3-trifluoropropene.
  • 1-Chloro-2,3,3-trifluoropropene (hereinafter, also referred to as 1233yd) is 3,3-dichloro-1,1,1,2,2-pentafluoropropane (hereinafter, also referred to as 225ca). , 1,3-Dichloro-1,1,2,2,3-pentafluoropropane (hereinafter also referred to as 225cc), new cleaning agents with a smaller global warming coefficient (GWP), refrigerants, foaming agents, solvents, And a compound used in aerosol applications.
  • GWP global warming coefficient
  • 1233yd has Z isomers and E isomers, which are geometric isomers, depending on the position of the substituent on the double bond.
  • Z is added after the compound name or the abbreviation of the compound.
  • (E) is attached, it indicates that it is a Z isomer or an E isomer of each compound.
  • 1233yd (Z) represents the Z isomer
  • 1233yd (E) represents the E isomer.
  • An object of the present invention is to provide a method for producing 1233 yd in a gas phase, which has a high conversion rate of raw materials, can obtain 1233 yd with a high selectivity, and produces a small amount of impurities.
  • the metal compound catalyst is a metal compound catalyst containing at least one metal element selected from the group consisting of Cr, Al, Zn, Ti and Ni.
  • the metal compound catalyst is a metal oxide, a metal fluoride, or a metal oxide fluoride.
  • the metal compound catalyst is aluminum oxide or chromium oxide.
  • the activation of the metal compound catalyst is performed by bringing the chlorine atom-free fluorine compound and the metal compound catalyst into contact with each other in a gas phase. The manufacturing method described.
  • the method for producing 1233 yd of the present invention is a method for obtaining 1233 yd using 244ca as a raw material.
  • the 244ca defluorinated hydrogen reaction (hereinafter, also simply referred to as “defluorinated hydrogen reaction”) according to the production method of the present invention is a reaction represented by the following formula (1).
  • the conversion rate of 244ca, which is a raw material, is high, and the amount of 1-chloro-3,3-difluoropropine, which is an impurity, is small.
  • the hydrogen fluoride reaction in the production method of the present invention is carried out in the gas phase from the viewpoint of reducing the amount of waste after production and increasing the productivity.
  • the hydrogen fluoride reaction in the gas phase means that 244ca in a gaseous state is subjected to a hydrogen fluoride reaction.
  • the production method of the present invention is characterized in that a metal compound catalyst activated with a fluorine atom containing no chlorine atom in the gas phase is used, and 244ca is subjected to a hydrogen fluoride reaction in the gas phase in the presence thereof.
  • the method for producing 1233yd of the present invention uses 244ca as a raw material.
  • 244ca is a compound known as a raw material or an intermediate for producing a fluorine-containing compound, and is easily available.
  • the method for obtaining 244ca is not particularly limited, and for example, as shown in the formula (2), 2,2,3,3-tetrafluoropropanol (TFPO) is chloride in the presence of N, N-dimethylformamide (DMF). It can be produced by a method of chlorination with thionyl (SOCl 2). This method can be carried out in the liquid phase or the gas phase.
  • TFPO 2,2,3,3-tetrafluoropropanol
  • DMF N, N-dimethylformamide
  • SOCl 2 thionyl
  • a general reactor such as a glass flask, a SUS autoclave, and a glass lining reactor can be used as the reactor.
  • a glass flask it is preferable to install a glass distillation column filled with Raschig ring and simultaneously generate and separate 244ca.
  • the amount of DMF added to 1 mol of TFPO is preferably 0.001 to 0.2 mol, and the amount of thionyl chloride added is preferably about 0.5 to 1.5 mol.
  • DMF acts catalytically to promote the reaction. Since the reaction of the formula (2) proceeds quantitatively in equimolar amounts, it is not necessary that either of them is excessive.
  • thionyl chloride at a rate such that the temperature fluctuation due to the reaction progress is within 30 ° C.
  • thionyl chloride reacts with water and is hydrolyzed to SO 2 and HCl.
  • 2,2,3,3-tetrafluoropropanesulfonic acid chloride is also hydrolyzed to decompose into TFPO, SO 2 and HCl. In order to prevent these, it is preferable to replace the atmosphere in the reactor with dry nitrogen gas.
  • the addition of thionyl chloride causes TFPO to react with thionyl chloride to produce 2,2,3,3-tetrafluoropropanesulfonic acid chloride.
  • 2,2,3,3-tetrafluoropropanesulfonic acid chloride is heated, it undergoes a sulfur dioxide desulfurization reaction to produce 244ca.
  • the temperature at the time of heating is 70 ° C. to 150 ° C., preferably 90 ° C. to 130 ° C.
  • the rate of temperature rise is arbitrary, but it is slowed down to about 1 to 2 ° C./min in order to avoid insufficient treatment of the produced sulfur dioxide and insufficient recovery of the produced 244ca.
  • the solvent has a boiling point higher than the reaction temperature of the 2,2,3,3-tetrafluoropropanesulfonic acid chloride decomposition reaction, and is a solvent that does not easily react with the compound involved in the reaction represented by the formula (2) and is aprotic. It is preferable to use a solvent. Specific examples include dimethyl sulfoxide, DMF and the like.
  • the amount of the solvent used is preferably about 0.5 to 3 mol with respect to 1 mol of 2,2,3,3-tetrafluoropropanesulfonic acid chloride.
  • the sulfur dioxide desulfurization reaction of 2,2,3,3-tetrafluoropropanesulfonic acid chloride it is preferable to prepare a reactor similar to the above and carry out the liquid phase reaction. That is, 244ca is produced by dropping 2,2,3,3-tetrafluoropropanesulfonic acid chloride in a reactor where a solvent is added and the mixture is heated to a temperature at which a sulfur dioxide reaction occurs.
  • the reaction temperature of the sulfur dioxide removal reaction is 70 ° C. to 150 ° C., preferably 90 ° C. to 130 ° C.
  • the atmosphere in the reaction vessel is preferably replaced with dry nitrogen gas.
  • the crude product of 244ca produced through the reaction of the formula (2) is usually a gaseous crude product, and is treated to remove hydrochloric acid and sulfur dioxide by a method such as washing with water to remove calcium chloride or molecular sieve.
  • a desiccant such as the above and subjecting it to a method such as cold trap, impurities can be removed and the composition containing 244ca can be recovered.
  • the obtained composition containing 244ca can be used as it is or by further purifying it, for example, as a composition having a purity of 99.5% by mass or more and used in the production method of the present invention.
  • a composition having a high purity of 244ca that has undergone a purification step may be used in addition to the 244ca having a purity of 100%, and contains components other than 244ca and 244ca (for example, impurities).
  • a composition containing 244ca may be used.
  • the impurity is an impurity active in the defluorinated hydrogen reaction in the present invention, it is preferable to remove it in advance.
  • TFPO should be removed from the product as much as possible. Is preferable.
  • 244ca is subjected to a hydrogen fluoride reaction in the presence of a metal compound catalyst activated by a fluorine compound containing no chlorine atom.
  • This defluorinated hydrogen reaction is carried out by a method in which the raw material 244ca is brought into contact with the activated metal compound catalyst in the gas phase.
  • Metal compound catalyst examples of the metal compound catalyst before activation in the present invention include metal oxides, metal fluorides, and metal oxide fluorides.
  • the metal compound catalyst one type may be used alone, or two or more types may be used in combination.
  • the metal element contained in the metal compound catalyst may be one kind or two or more kinds.
  • the metal compound may be a mixture of two or more kinds of metal compounds having different metal elements, or may be a metal compound containing two or more kinds of metal elements. good.
  • the metal compound catalyst before activation is a metal compound containing at least one metal element selected from the group consisting of Co, Fe, Pd, Sn, Mg, La, Cr, Al, Zn, Ti and Ni.
  • the metal compound contains at least one metal element selected from the group consisting of Cr, Al, Zn, Ti and Ni.
  • metal oxides include chromium oxide, aluminum oxide, zinc oxide, titanium oxide, nickel oxide and the like.
  • the fluoride of the metal may be a hydrate, and examples thereof include chromium fluoride, aluminum fluoride, titanium fluoride, zinc fluoride, titanium fluoride, and nickel fluoride.
  • the fluorinated metal oxide include those in which chromium oxide, aluminum oxide, zinc oxide, titanium oxide, nickel oxide and the like are partially fluorinated.
  • metal compound catalyst metal oxides are preferable, and aluminum oxide and chromium oxide are more preferable, from the viewpoint of conversion and selectivity.
  • the metal compound catalyst may be supported on a carrier.
  • the carrier include an alumina carrier, a silica carrier, and a silica alumina carrier.
  • the carrier may have a catalytic activity that promotes the defluorinated hydrogen reaction.
  • an activated metal compound catalyst is used.
  • the activation here means that the fluorine compound containing no chlorine atom and the metal compound catalyst are brought into contact with each other in the gas phase.
  • the activated metal compound catalyst is preferably partially fluorinated.
  • the fluorine compound containing no chlorine atom one type may be used alone, or two or more types may be used in combination.
  • hydrogen fluoride, fluorinated alkane, and fluorinated alkene are preferable, and hydrogen fluoride and fluorinated alkane are more preferable.
  • fluorine compound containing no chlorine atom a fluorine compound containing hydrogen fluoride and a chlorine atom having 1 to 3 carbon atoms is preferable, and a fluorine compound containing hydrogen fluoride and a chlorine atom having 1 to 2 carbon atoms is more preferable.
  • Fluorine compounds free of hydrogen fluoride and chlorine atom having 1 carbon atom are most preferable.
  • Examples of the fluorine compound containing no chlorine atom having 1 carbon atom include trifluoromethane and difluoromethane.
  • Examples of the fluorine compound containing no chlorine atom having 2 carbon atoms include pentafluoroethane, 1,1,2,2-tetrafluoroethane, 1,1,1-trifluoroethane and the like.
  • Examples of the fluorine compound containing no chlorine atom having 3 carbon atoms include hexafluoropropane, 1,2,3,3-tetrafluoropropene and the like.
  • As the fluorine compound containing no chlorine atom hydrogen fluoride, trifluoromethane and difluoromethane are preferable, and hydrogen fluoride and trifluoromethane are more preferable from the viewpoint of conversion rate of raw materials and suppression of impurities.
  • a gaseous chlorine atom-free fluorine compound is introduced into a solid metal compound catalyst filled in a reactor and brought into contact with the catalyst.
  • the method can be mentioned.
  • the raw material 244ca is introduced into the reactor to cause a defluorinated hydrogen reaction.
  • a method in which a mixed gas of a raw material 244ca and a fluorine compound containing no chlorine atom is introduced into a reactor filled with a metal compound catalyst in a solid state to activate the metal compound catalyst and perform a defluorinated hydrogen reaction at the same time. But it may be.
  • the former method is preferable from the viewpoint of sufficiently activating the metal compound catalyst.
  • the metal compound catalyst is activated outside the reactor with a fluorine compound gas containing no chlorine atom, the activated metal catalyst is filled in the reactor, and the raw material 244ca is introduced to defluoride. It can also be reacted with hydrogen.
  • the temperature of the catalyst activation treatment in the present invention (hereinafter, also referred to as activation treatment temperature) is preferably 100 to 400 ° C, more preferably 150 to 400 ° C, still more preferably 200 to 400 ° C, and 250 to 400 ° C. Is particularly preferable, and 250 to 350 ° C. is most preferable.
  • the metal compound catalyst can be sufficiently activated. If the activation treatment temperature does not reach the above range, the activity of the metal compound catalyst may be insufficient and the conversion rate of the raw material may decrease. If the activation treatment temperature exceeds the above range, the activity and lifetime of the metal compound catalyst may decrease.
  • the reaction time (the time refers to the contact time between the fluorine compound containing no chlorine atom and the metal compound catalyst) is preferably 0.1 to 100 seconds, more preferably 1 to 80 seconds. Most preferably 5 to 60 seconds. Within the above range, the metal compound catalyst can be sufficiently activated. If the reaction temperature is high, the reaction time is short, and if the reaction temperature is low, the reaction time is preferably long.
  • the pressure inside the reactor that undergoes the hydrogen defluorination reaction is preferably 0 to 2 MPa.
  • a gaseous raw material 244ca is introduced into an activated metal compound catalyst packed in a reactor, and the two are brought into contact with each other to cause a defluorinated hydrogen reaction.
  • the defluorinated hydrogen reaction may be carried out by a batch method or a continuous method (including a semi-continuous type or a continuous flow type), and is preferably performed by a continuous method from the viewpoint of production efficiency.
  • a continuous method including a semi-continuous type or a continuous flow type
  • the material of the reactor is not particularly limited as long as it is a material that is inert to the raw material, solvent, reaction product and the like and has corrosion resistance. Examples of the material of the reactor include alloys such as glass, iron, nickel, and stainless steel containing iron as a main component.
  • the temperature of the defluorinated hydrogen reaction (hereinafter, also referred to as reaction temperature) is preferably 200 to 400 ° C, more preferably 250 to 400 ° C, and most preferably 275 to 400 ° C. preferable.
  • reaction temperature is preferably 200 to 400 ° C, more preferably 250 to 400 ° C, and most preferably 275 to 400 ° C. preferable.
  • the generation of impurities can be suppressed and 1233 yd can be obtained with a high selectivity. If the reaction temperature does not reach the above range, the reaction rate and the reaction yield may decrease, and if unreacted 244ca remains in excess, it may be difficult to separate from 1233yd.
  • reaction temperature exceeds the above range, the amount of 1-chloro-3,3-difluoropropine produced by further defluorinating hydrogen of 1233yd may increase, and the selectivity of 1233yd may decrease. There is sex.
  • the reaction time (the time refers to the contact time between the raw material and the activated metal compound catalyst) is from the viewpoint of suppressing the conversion rate of the raw material and the formation of impurities. , 0.1 to 100 seconds, more preferably 1 to 80 seconds, and most preferably 5 to 60 seconds. If the reaction temperature is high, the reaction time is short, and if the reaction temperature is low, the reaction time is preferably long.
  • the pressure inside the reactor that undergoes the hydrogen defluorination reaction is preferably 0 to 2 MPa.
  • the content of 1-chloro-3,3-difluoropropine is 10% by mass or less with respect to the total amount of the reaction crude liquid from the viewpoint of the selectivity of 1233 yd. Is preferable, and it is more preferably 5% by mass or less, and most preferably 1% by mass or less.
  • the crude reaction solution in the present invention is a crude solution containing unreacted raw materials and reaction products. If unreacted 244ca remains, it is also possible to concentrate 244ca by distillation and recycle it as a raw material of the present invention.
  • the acid content that is, the content of chloride ion and fluorine ion, is preferably less than 10 mass ppm, more preferably less than 1 mass ppm, and most preferably less than 0.1 mass ppm, respectively, with respect to the total amount of purified 1233 yd. Is.
  • the water concentration in the purified 1233 yd is preferably less than 2000 mass ppm, more preferably less than 1500 mass ppm, still more preferably less than 1000 mass ppm, and most preferably less than 100 mass ppm.
  • the oxygen concentration in the purified 1233 yd is preferably 1000 mass ppm or less, more preferably 500 mass ppm or less. Outside the above range, decomposition of 1233 yd may occur and degreasing cleaning performance may be impaired.
  • the purified 1233 yd containing 1233 yd with high purity may be only one of 1233 yd (Z) or 1233 yd (E), but the ratio of 1233 yd (Z) is preferably high in consideration of productivity.
  • the content of 1233 yd (Z) is preferably 50% by mass or more, more preferably 75 to 98% by mass, and particularly preferably 90 to 98% by mass.
  • the preheating temperature is preferably 244 ca or more and 200 ° C. or less.
  • the boiling point of the compound is the value of the pressure 1.013 ⁇ 10 5 Pa (absolute pressure).
  • the defluorinated hydrogen reaction in the gas phase it is preferable to mix 244ca with a diluting gas and supply it to the reactor in order to suppress the formation of by-products.
  • a diluting gas an inert gas such as nitrogen gas, helium gas, or argon gas can be used.
  • the amount of the diluted gas is preferably 0.1 to 10 mol with respect to 1 mol of 244ca supplied to the reactor.
  • 244ca may be preheated before being mixed with the diluted gas, or may be preheated after mixing.
  • Examples 1, 5 and 6 are examples of the present invention, and Examples 2 to 4 are comparative examples.
  • composition analysis of the obtained reaction product was performed using gas chromatography (GC).
  • GC gas chromatography
  • DB-1301 length 60 m ⁇ inner diameter 250 ⁇ m ⁇ thickness 1 ⁇ m, manufactured by Agilent Technologies, Inc.
  • 244ca was produced by the following method.
  • the following method is a method for obtaining 244ca by chlorinating TFPO with thionyl chloride as shown in the above formula (2).
  • Example 1 An insertion tube (material: SUS316, diameter: 3 mm) is introduced in the center of a vertical fixed floor reactor (material: SUS316, inner diameter 22.6 mm x height 200 mm), and a K-type thermocouple is inserted into it. The temperature was measured. Alumina (manufactured by JGC Catalysts and Chemicals Co., Ltd., N612N) was filled in the central part of the reactor, and this was used as a catalyst layer. The catalyst layer was heated to 300 ° C. by an electric furnace while supplying nitrogen gas at 300 mL / min and dried.
  • Alumina manufactured by JGC Catalysts and Chemicals Co., Ltd., N612N
  • trifluoromethane (R-23) was supplied at 300 mL / min, and the catalyst was activated for about 10 hours until the composition of the outlet gas was stabilized.
  • a raw material preheating mixing line heated to 70 ° C. connecting a gas feed line and a raw material supply line was connected to the upper part of the reactor. Nitrogen was supplied from the gas feed line to the raw material preheating mixing line by adjusting the gas flow rate using a mass flow controller.
  • the raw material 244ca was supplied to a raw material preheating mixing line heated to 70 ° C. through a raw material supply line by adjusting the liquid flow rate using a plunger pump. The product was continuously removed from the bottom of the reactor.
  • Example 2 to 4 A vertical fixed-bed reactor (material: SUS316, inner diameter 22.6 mm x height 200 mm) was used as the reactor, and alumina (manufactured by JGC Catalysts and Chemicals Co., Ltd., N612N) was used as the catalyst. The catalyst was dried at ° C. After that, chlorodifluoromethane (R-22) was supplied at 300 mL / min, and the catalyst was activated for about 10 hours until the composition of the outlet gas was stabilized. The reaction was carried out in the same procedure as in Example 1 except that the reaction temperature and other reaction conditions were changed to the conditions shown in Table 1. The reaction conditions and results are shown in Table 1.
  • Example 5 If the reaction is carried out in the same procedure as in Example 1 except that the catalyst is activated with hydrogen fluoride or difluoromethane instead of trifluoromethane, the same result as in Example 1 is obtained. As such examples, (Example 5) and (Example 6) are shown below.
  • Example 5 A vertical fixed-bed reactor (material: SUS316, inner diameter 22.6 mm x height 200 mm) was used as the reactor, and alumina (manufactured by JGC Catalysts and Chemicals Co., Ltd., N612N) was used as the catalyst. The catalyst was dried at ° C. After that, hydrogen fluoride was supplied at 100 mL / min to activate the catalyst for about 10 hours. The reaction was carried out in the same procedure as in Example 1 except that the reaction temperature and other reaction conditions were changed to the conditions shown in Table 2. The reaction conditions and results are shown in Table 2.
  • Example 6 A vertical fixed-bed reactor (material: SUS316, inner diameter 22.6 mm x height 200 mm) was used as the reactor, and alumina (manufactured by JGC Catalysts and Chemicals Co., Ltd., N612N) was used as the catalyst. The catalyst was dried at ° C. Then, difluoromethane (R-32) was supplied at 300 mL / min to activate the catalyst for about 10 hours. The reaction was carried out in the same procedure as in Example 1 except that the reaction temperature and other reaction conditions were changed to the conditions shown in Table 2. The reaction conditions and results are shown in Table 2.
  • the reaction is carried out using 244ca, which is easily available and can be stably supplied, without using a special operation or a reaction device, thereby having a high reaction rate and a high selectivity of 1233yd. It has become possible to apply industrial-scale mass production.

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

Abstract

La présente invention concerne un procédé de production de 1233yd en phase vapeur, ledit procédé ayant un taux de conversion élevé d'une matière de départ et permettant d'obtenir le 1233yd avec une sélectivité élevée, tout en supprimant la production d'une certaine quantité d'impuretés.　L'invention porte sur un procédé de production de 1-chloro-2,3,3-trifluoropropène par soumission de 3-chloro-1,1,2,2-tétrafluoropropane à une réaction d'élimination du fluorure d'hydrogène en phase vapeur en présence d'un catalyseur, ledit procédé étant caractérisé en ce qu'on utilise comme catalyseur un catalyseur à base d'un composé métallique, qui est activé en phase vapeur par un composé fluoré qui ne contient pas d'atome de chlore.
PCT/JP2021/025938 2020-07-15 2021-07-09 Procédé de production de 1-chloro-2,3,3-trifluoropropène WO2022014488A1 (fr)

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CN202180048922.8A CN115803308A (zh) 2020-07-15 2021-07-09 1-氯-2,3,3-三氟丙烯的制造方法
JP2022536321A JPWO2022014488A1 (fr) 2020-07-15 2021-07-09

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994014737A1 (fr) * 1992-12-29 1994-07-07 Daikin Industries, Ltd. Procede de production de 1,1,2,2,3-pentafluoropropane
JPH11507870A (ja) * 1995-06-08 1999-07-13 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー 酸化クロムの処理及びフッ化ビニルの触媒的製造
JP2014511351A (ja) * 2011-01-21 2014-05-15 アルケマ フランス 気相触媒フッ素化
JP2020079230A (ja) * 2018-10-09 2020-05-28 ダイキン工業株式会社 パーフルオロアルキン化合物の製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994014737A1 (fr) * 1992-12-29 1994-07-07 Daikin Industries, Ltd. Procede de production de 1,1,2,2,3-pentafluoropropane
JPH11507870A (ja) * 1995-06-08 1999-07-13 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー 酸化クロムの処理及びフッ化ビニルの触媒的製造
JP2007191394A (ja) * 1995-06-08 2007-08-02 E I Du Pont De Nemours & Co 酸化クロムの処理及びフッ化ビニルの触媒的製造
JP2014511351A (ja) * 2011-01-21 2014-05-15 アルケマ フランス 気相触媒フッ素化
JP2020079230A (ja) * 2018-10-09 2020-05-28 ダイキン工業株式会社 パーフルオロアルキン化合物の製造方法

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