WO2018139654A1 - Procédé de fabrication de 1,1,2,2-tétrafluoropropane - Google Patents

Procédé de fabrication de 1,1,2,2-tétrafluoropropane Download PDF

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Publication number
WO2018139654A1
WO2018139654A1 PCT/JP2018/002786 JP2018002786W WO2018139654A1 WO 2018139654 A1 WO2018139654 A1 WO 2018139654A1 JP 2018002786 W JP2018002786 W JP 2018002786W WO 2018139654 A1 WO2018139654 A1 WO 2018139654A1
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Prior art keywords
tetrafluoropropane
catalyst
reaction
hydrogen
producing
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PCT/JP2018/002786
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English (en)
Japanese (ja)
Inventor
真理 市野川
厚史 藤森
岡本　秀一
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Ａｇｃ株式会社
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Priority to JP2018564693A priority Critical patent/JPWO2018139654A1/ja
Publication of WO2018139654A1 publication Critical patent/WO2018139654A1/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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the present invention relates to a method for producing 1,1,2,2-tetrafluoropropane.
  • 1,1,2,2-tetrafluoropropane (CHF 2 —CF 2 —CH 3 (HFC-254cb)) is a rigid polyurethane foam blowing agent, solvent, cleaning agent, aerosol, refrigerant, working fluid, propellant, or It is useful as a raw material for them and fluororesins.
  • HFC-254cb for example, 1,3,3-trichloro-1,1,2,2-tetrafluoropropane (CClF 2 -CF 2 -CHCl 2 ( HCFC-224ca), hereinafter also referred to as 224ca. ) And 1,1,1-trichloro-2,2,3,3-tetrafluoropropane (CHF 2 —CF 2 —CCl 3 (HCFC-224 cc), hereinafter also referred to as 224 cc)) in the presence of a hydrogenation catalyst.
  • a method for producing HFC-254cb by reacting with hydrogen is known (for example, see Patent Document 1).
  • the selectivity of the target product, 254cb is as low as 1% or less.
  • the selectivity of 254 cb is low, and 3-chloro-1,1,2,2-tetrafluoropropane (CHF 2 —CF 2 —CH 2 Cl (HCFC-244ca), hereinafter 244ca) is used.
  • CHF 2 —CF 2 —CH 2 Cl HCFC-244ca
  • the present invention uses 1-chloro-1,1,2,2-tetrafluoropropane (CClF 2 —CF 2 —CH 3 (HCFC-244cc), hereinafter also referred to as 244cc), which is an easily available raw material.
  • Economically advantageous 254 cb of 1,1,2,2-tetrafluoropropane (CHF 2 —CF 2 —CH 3 (HFC-254cb), hereinafter also referred to as 254cb)) can be obtained with high selectivity.
  • the object is to provide a manufacturing method.
  • the present invention provides a method for producing 1,1,2,2-tetrafluoropropane having the following constitution.
  • 1,1,2,2-Tetra characterized by reacting 1-chloro-1,1,2,2-tetrafluoropropane and hydrogen at a temperature exceeding 200 ° C. in the presence of a catalyst A method for producing fluoropropane.
  • 254 cb is produced by reacting 244 cc with hydrogen at a temperature exceeding 200 ° C. in the presence of a catalyst.
  • the method of reacting 244 cc with hydrogen in the presence of a catalyst is not particularly limited except for the reaction temperature.
  • the reaction between 244 cc and hydrogen is performed by supplying 244 cc and hydrogen to a reaction field where the catalyst is disposed (usually in a reactor in which the catalyst is accommodated).
  • a method of supplying 244 cc and hydrogen to react in a reactor containing a catalyst will be described, but the present invention is not limited thereto.
  • the reaction between 244 cc and hydrogen may be performed in the liquid phase or in the gas phase. It is preferable to carry out the reaction in the gas phase because there are advantages that the reaction time can be shortened and the production of by-products can be suppressed.
  • the manufacturing method of this embodiment can be performed by either a batch method or a continuous method.
  • 244 cc and hydrogen are supplied to a reactor containing a catalyst, 244 cc is reacted in the reactor, and hydrogen is brought into contact with the catalyst, and the 254 cb reactor obtained by the reaction is used. The removal from is performed continuously.
  • the timing of supplying 244 cc and hydrogen into the reactor containing the catalyst is not particularly limited in both batch and continuous methods. That is, either one may be supplied first and the other may be supplied later, or both may be supplied simultaneously.
  • the previously supplied component is retained in the reactor, and the other component is supplied to the reactor so that 244 cc, hydrogen, catalyst, May be contacted for a predetermined time.
  • 244 cc and hydrogen may be supplied to the reactor from separate supply pipes, or may be mixed in advance and supplied from one supply pipe.
  • the manufacturing method of the present embodiment is preferably a continuous method in terms of manufacturing efficiency.
  • the manufacturing method of the present embodiment will be described with respect to a method of reacting 244 cc with hydrogen in a gas phase in a continuous manner.
  • the amount of hydrogen used is preferably about 0.1 to 5.0 moles, more preferably 0.5 to 3.0 moles per mole of 244 cc. If the amount of hydrogen is not less than the lower limit, the conversion rate is improved. Moreover, if the quantity of hydrogen is below the said upper limit, the production
  • (244cc) 244 cc used in the production method of the present embodiment is a compound represented by the general formula (A): CClF 2 CF 2 CH a Cl (3-a) (wherein a is an integer of 0 to 2).
  • the compound (A) can be easily produced by bringing it into contact with hydrogen in the presence of a hydrogenation catalyst to cause a reduction reaction.
  • this reduction reaction one of the compounds (A) in which a is an integer of 0 to 2 may be used alone, or two or more compounds (A) having different a may be used as raw materials. It is good.
  • a compound in which a is 0 is 1,1,1,3-tetrachloro-2,2,3,3-tetrafluoropropane (CClF 2 -CF 2 -CCl 3 (CFC-214cb ), Hereinafter also referred to as 214cb), the compound in which a is 1 is 224ca, and the compound in which a is 2 is 1,3-dichloro-1,1,2,2-tetrafluoropropane (CCIF 2 -CF 2 -CClH 2 (HCFC-234cc), hereinafter also referred to as 234cc).
  • 214cb and 224ca can be obtained by reacting tetrafluoroethylene (TFE) with one or both of CCl 4 and CHCl 3 in the presence of a Lewis acid catalyst such as aluminum chloride.
  • TFE tetrafluoroethylene
  • 234 cc is obtained by hydrogenating one or both of 214cb and 224ca obtained above in the presence of, for example, a palladium catalyst, or reacting TFE and CH 2 Cl 2 in the presence of a Lewis acid catalyst as described above. Can be obtained.
  • Reduction reaction by contacting a compound represented by the above general formula (A) obtained by these methods, specifically 214cb, 224ca, 234cc, etc. with hydrogen in the presence of a hydrogenation catalyst such as a palladium catalyst. By doing so, a composition containing 244 cc can be obtained.
  • a hydrogenation catalyst such as a palladium catalyst.
  • the composition containing 244 cc obtained by the above method may contain 244 cc, TFE, 214 cb, 224 ca, 234 cc, CH 2 Cl 2 , CCl 4 , CHCl 3, etc. in addition to 244 cc. is there.
  • the composition containing 244 cc obtained by the above method may be used as a raw material as it is, and known methods such as distillation, extractive distillation, azeotropic distillation, membrane separation, two-layer separation, adsorption, etc.
  • a material having an increased purity of 244 cc may be used as a raw material.
  • 244 cc and other compounds other than hydrogen may be supplied to the reactor containing the catalyst.
  • examples of other compounds include the above-mentioned 244 cc production raw materials and by-products produced in addition to 244 cc when 244 cc is produced.
  • by-products generated from the other compounds should be removed by known means such as distillation, extractive distillation, azeotropic distillation, membrane separation, two-layer separation, and adsorption. Is possible.
  • the other compound is preferably a compound that is inactive under the reaction conditions of the reaction between 244 cc and hydrogen.
  • Catalyst The catalyst used in the production method of the present invention is not particularly limited as long as it has a function of promoting the reaction between 244 cc and hydrogen.
  • Catalysts include Group 4 elements such as zirconium, Group 6 elements such as molybdenum, Group 7 elements such as rhenium, Group 8 elements such as iron, ruthenium and osmium, and Group 9 elements such as cobalt, rhodium and iridium. Examples thereof include metals such as elements, Group 10 elements such as palladium, nickel and platinum, and Group 11 elements such as gold.
  • the catalyst preferably contains at least one metal selected from platinum, palladium, rhodium, ruthenium, nickel, rhenium, molybdenum and zirconium from the viewpoint of improving the conversion rate of 244 cc and the selectivity of 254 cb.
  • the catalyst may be one of the above metals or two or more.
  • the catalyst composed of two or more metals may be a mixture of two or more metals or an alloy of two or more metals.
  • group 9 elements, group 10 elements palladium and platinum are particularly preferable in that the selectivity of 254cb is further improved.
  • the catalyst is preferably used by being supported on a carrier in order to improve the reactivity.
  • the carrier is not particularly limited as long as it can sufficiently carry the catalyst.
  • the carrier preferably includes at least one carrier selected from alumina, activated carbon, zirconia, and silica. As the carrier, alumina and activated carbon are preferable, and activated carbon is more preferable in that the conversion rate of 244 cc and the selectivity of 254 cb are further improved.
  • One type of carrier may be used alone, or two or more types may be used in combination.
  • the activated carbon examples include activated carbon obtained from plant raw materials such as wood, charcoal, fruit husk and coconut husk, and mineral raw materials such as peat, lignite and coal.
  • the carrier for supporting the hydrogenation catalyst activated carbon obtained from plant raw materials is preferable from the viewpoint of catalyst durability, and coconut shell activated carbon is particularly preferable.
  • the shape of the activated carbon may be any shape, and examples thereof include formed coal having a length of about 2 to 10 mm, crushed coal having a size of about 4 to 50 mesh, and granular coal.
  • alumina supporting palladium, activated carbon supporting palladium, activated carbon supporting platinum, and the like are preferable because the catalytic activity can be maintained for a long time.
  • the amount of the catalyst supported on the carrier is preferably 0.1 to 10% by mass, more preferably 0.5 to 3% by mass, more preferably 1.0 to 3% by mass is more preferable, and 1.5 to 2.5% by mass is most preferable. If the supported amount of the catalyst is at least the lower limit value, the reaction rate between the raw material and hydrogen and the conversion rate of 244 cc can be improved. If the supported amount of the catalyst is not more than the upper limit value, it is easy to suppress an excessive temperature rise of the catalyst due to the heat of reaction, and it is easy to reduce the production of by-products.
  • the reaction temperature when 244 cc and hydrogen are reacted in a gas phase is a temperature exceeding 200 ° C., preferably about 210 to 350 ° C., more preferably 250 to 300 ° C. If the reaction time is not less than the lower limit, the conversion rate of 244 cc is good, and if the reaction time is not more than the upper limit, the production of by-products can be suppressed and catalyst deterioration can be suppressed.
  • the reaction temperature refers to the temperature in the reactor where 244 cc reacts with hydrogen, more specifically, the temperature of the catalyst.
  • the contact time (reaction time) of 244 cc and hydrogen in the reactor is preferably about 4 to 120 seconds, more preferably about 8 to 100 seconds. If the contact time is equal to or greater than the lower limit value, the conversion rate of 244 cc is good, and if the contact time is equal to or less than the upper limit value, generation of by-products can be suppressed.
  • the contact time can be controlled by adjusting the supply amount (flow rate) of 244 cc and hydrogen to the reactor.
  • the reaction pressure can be normal pressure or under pressure, but it is preferable to carry out the reaction at normal pressure from the viewpoint of ease of industrial implementation.
  • a diluent gas may be further supplied into the reactor.
  • a diluent gas By supplying the diluting gas into the reactor and allowing it to flow and adjusting the concentration of 244 cc and hydrogen contacted with the catalyst, an excessive temperature rise of the catalyst due to the heat of reaction can be suppressed, and the reaction can be performed safely.
  • an inert gas such as nitrogen gas or a rare gas, or chlorofluorocarbons inert to the hydrogenation reaction of this embodiment can be used. Of these, nitrogen gas is preferred as the dilution gas. Dilution gas may be used individually by 1 type, and may use 2 or more types together.
  • the amount of dilution gas supplied into the reactor is easy to maintain the maximum temperature of the catalyst low, easily reduce the production of by-products, and suppress the deterioration of the catalyst and maintain the catalyst activity for a long time.
  • 0.1 mol or more is preferable with respect to 1 mol of 244cc, and 0.5 mol or more is more preferable.
  • the supply amount of the dilution gas is preferably 10 mol or less, more preferably 5 mol or less, and further preferably 3 mol or less with respect to 1 mol of 244 cc from the viewpoint of the recovery rate of the dilution gas.
  • the reactor used in the production method of the present embodiment is not particularly limited as long as it is a reactor that can be filled with a catalyst, preferably a catalyst support, to form a catalyst layer.
  • a catalyst preferably a catalyst support
  • Examples of the material for the reactor include glass, iron, nickel, and alloys containing these as main components.
  • the catalyst preferably a catalyst-supporting carrier
  • the catalyst may be accommodated in either a fixed bed type or a fluidized bed type.
  • a fixed bed type it may be either a horizontal fixed bed type or a vertical fixed bed type, but in a mixed gas composed of multiple components, the concentration distribution of each component is generated depending on the location due to the difference in specific gravity. It is preferable to use a vertical fixed floor type.
  • the 244 cc and hydrogen supplied to the reactor are kept as they are when they are mixed in advance, or they are usually mixed in the vicinity of the inlet of the reactor in the direction from the inlet side to the outlet when they are separated. It distribute
  • the product gas discharged from the outlet of the reactor contains 244 cc which is an unreacted raw material, hydrogen, various by-products and HCl in addition to 254 cb which is a target substance.
  • the by-product is, for example, a compound having 6 carbon atoms (C6 compound) in which 244 cc and 254 cb produced, 244 cc or 254 cb are bonded (C1 compound), a compound having 1 carbon (C1 compound) in which 244 cc or 254 cb is decomposed, or 2 carbon atoms.
  • Components other than 254cb in the outlet gas can be removed to the extent desired by distillation or the like. Further, 244 cc in the outlet gas can also be separated by distillation or the like. The separated 244 cc can be recycled as a production raw material of 254 cb by returning it to the reactor again. By recycling the unreacted raw material in this manner, the productivity of 254cb as a whole can be increased even when the conversion rate of 244cc in the reaction of 244cc and hydrogen is low.
  • reaction of 244cc and hydrogen when performing the manufacturing method of this embodiment in a liquid phase, you may perform reaction of 244cc and hydrogen using a solvent, and without solvent.
  • a solvent alcohols such as ethanol and isopropyl alcohol, acetic acid, ethyl acetate, pyridine and the like can be used as the solvent.
  • 244 cc can be liquefied by pressurization.
  • the reaction temperature is preferably from room temperature (about 25 ° C.) to about 150 ° C.
  • the reaction pressure is preferably from atmospheric pressure to about 5 MPa.
  • the reaction time is usually preferably about 1 to 72 hours.
  • the reaction time is preferably 1 to 9 hours.
  • 244cb can be easily obtained with high selectivity using 244cc that is easily available as a raw material, which is economically advantageous.
  • Examples 1 to 13 are examples of the present invention, and Examples 14 to 19 are comparative examples.
  • anhydrous aluminum chloride 25 g, 0.19 mol
  • CHCl 3 500 g, 4.19 mol
  • 224ca 100 g, 0.45 mol
  • reaction solution was cooled to room temperature and analyzed by gas chromatography.
  • the conversion of CHCl 3 was 33% and the selectivity of 224ca was 84%.
  • 102 g of molecular sieve 4A was added and stirred overnight to dehydrate.
  • 224ca (230 g, 1.05 mol) was manufactured by distilling and purifying the crude product obtained by separating the stirred crude liquid by filtration.
  • a gas phase reactor made of SUS316, diameter 25 mm, length 30 cm
  • activated carbon pellets 15 g supporting palladium at a ratio of 2.0 mass%
  • the temperature was raised to 130 ° C. while flowing nitrogen (N 2 ) gas (500 NmL / min).
  • N 2 nitrogen
  • the catalyst was dried until the moisture in the crude gas after passing through the reactor became 20 ppm or less.
  • the supply of nitrogen was stopped, the reaction tube was heated to 200 ° C. while supplying hydrogen (180 mL / min), and then 224ca (0.44 g / min) was supplied.
  • the crude gas from the reaction tube was washed with water, and then acid and moisture were removed through an alkali washing tower and molecular sieve 5A, and then collected in a cold trap.
  • the conversion rate of 224ca was 98%, and 234cc was obtained with a selectivity of 24% and 244cc with a selectivity of 70%.
  • a total of 500 g (2.27 mol) of 224ca was reacted above to give 298 g of crude product.
  • the obtained crude product was subjected to normal pressure rectification in a 25-stage rectification column to obtain 244 cc (210 g, 1.4 mol).
  • Example 1 First, a gas phase reactor (made of Inconel (registered trademark) 600, a reaction tube having a diameter of 26 mm and a length of 60 cm) including a cylindrical reaction tube equipped with a salt bath furnace is used with respect to 100% by mass of activated carbon (crushed coal). A palladium catalyst supporting palladium at a ratio of 0.5% by mass was filled to form a catalyst layer having a height of 40 cm. After heating the reactor to 250 ° C. in a salt bath furnace, 244 cc and hydrogen are supplied so that the ratio of the molar flow rate per unit time of 244 cc and hydrogen (H 2 ) (244 cc / H 2 ) is halved. For 30 seconds to obtain a product gas.
  • a gas phase reactor made of Inconel (registered trademark) 600, a reaction tube having a diameter of 26 mm and a length of 60 cm
  • a palladium catalyst supporting palladium at a ratio of 0.5% by mass was filled to form a catalyst layer
  • the generated gas was analyzed using gas chromatography (GC).
  • DB-1301 length 60 m ⁇ inner diameter 250 ⁇ m ⁇ thickness 1 ⁇ m, manufactured by Agilent Technologies
  • the conversion and selectivity were calculated by the following formulas.
  • Examples 2 to 8 The reaction was performed in the same manner as in Example 1 except that the reaction conditions were changed as shown in Tables 1 and 2. Tables 1 and 2 show the conversion rate of 244 cc and the selectivity of each compound produced together with the reaction conditions. In Examples 5 and 6, in addition to 244 cc, hydrogen, nitrogen was also supplied. The nitrogen supply molar ratio is also shown in Table 2.
  • Example 9 to 13 The reaction was performed in the same manner as in Example 1 except that the catalyst was changed to activated carbon pellets carrying palladium at a ratio of 2.0% by mass and the reaction conditions were changed as shown in Table 3. The conversion rate of 244 cc and the selectivity of each compound produced are shown in Table 3 together with the reaction conditions.
  • Example 14 to 17 The raw material was changed from 244cc to 214cb, and activated carbon pellets carrying palladium at a ratio of 2.0% by mass were used as a catalyst. Moreover, reaction conditions were set as shown in Table 4. The reaction was performed in the same manner as in Example 1 except for these. The composition of the product gas was analyzed by GC in the same manner as in Example 1, and the conversion rate of 214 cb as a raw material and the selectivity of each compound produced were calculated by the above formula.
  • Example 18 The reaction was carried out in the same manner as in Example 1 except that the reaction conditions were changed as shown in Table 5.
  • Table 5 shows the conversion rate of 244 cc and the selectivity of each compound produced together with the reaction conditions.

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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)
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Abstract

L'invention fournit un procédé de fabrication de ＨＦＣ－２５４ｃｂ avantageux d'un point de vue économique, qui permet d'obtenir un 1,1,2,2-tétrafluoropropane (ＨＦＣ－２５４ｃｂ) aisément et selon une sélectivité élevée, à l'aide de matières premières faciles à se procurer. Plus précisément, l'invention concerne un procédé de fabrication de 1,1,2,2-tétrafluoropropane qui est caractéristique en ce qu'il inclut la réaction à une température dépassant 200°C d'un 1-chloro-1,1,2,2-tétrafluoropropane (ＨＣＦＣ－２４４ｃｃ) et d'un hydrogène, en présence d'un catalyseur.
PCT/JP2018/002786 2017-01-30 2018-01-29 Procédé de fabrication de 1,1,2,2-tétrafluoropropane WO2018139654A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990008753A1 (fr) * 1989-02-02 1990-08-09 Asahi Glass Company Ltd. Procede de production d'un 2,2-difluoropropane contenant de l'hydrogene
JPH02207037A (ja) * 1989-02-06 1990-08-16 Asahi Glass Co Ltd ジフルオロメチレン基を有するテトラヒドロフルオロプロパン類およびテトラヒドロクロロフルオロプロパン類の製造方法
JPH0383937A (ja) * 1989-08-25 1991-04-09 Asahi Glass Co Ltd ジクロロペンタフルオロプロパンの製法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990008753A1 (fr) * 1989-02-02 1990-08-09 Asahi Glass Company Ltd. Procede de production d'un 2,2-difluoropropane contenant de l'hydrogene
JPH02207037A (ja) * 1989-02-06 1990-08-16 Asahi Glass Co Ltd ジフルオロメチレン基を有するテトラヒドロフルオロプロパン類およびテトラヒドロクロロフルオロプロパン類の製造方法
JPH0383937A (ja) * 1989-08-25 1991-04-09 Asahi Glass Co Ltd ジクロロペンタフルオロプロパンの製法

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