WO2017138667A1 - Procédé de fabrication d'hydrocarbure insaturé, et procédé de fabrication de diène conjugué - Google Patents

Procédé de fabrication d'hydrocarbure insaturé, et procédé de fabrication de diène conjugué Download PDF

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WO2017138667A1
WO2017138667A1 PCT/JP2017/005145 JP2017005145W WO2017138667A1 WO 2017138667 A1 WO2017138667 A1 WO 2017138667A1 JP 2017005145 W JP2017005145 W JP 2017005145W WO 2017138667 A1 WO2017138667 A1 WO 2017138667A1
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catalyst
carrier
group
alkane
dehydrogenation
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PCT/JP2017/005145
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English (en)
Japanese (ja)
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隼二 若林
竜也 一條
信啓 木村
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Ｊｘエネルギー株式会社
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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
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/08—Alkenes with four carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/12—Alkadienes
    • C07C11/16—Alkadienes with four carbon atoms
    • C07C11/167—1, 3-Butadiene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • 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 unsaturated hydrocarbons and a method for producing conjugated dienes.
  • Examples of the method for producing butadiene include a method for producing conjugated diene by direct dehydrogenation of n-butane using a dehydrogenation catalyst (Patent Document 1), and a conjugated diene by oxidative dehydrogenation of n-butene. There is known a method for manufacturing (Patent Documents 2 to 4).
  • the present inventors have found that alkanes can be efficiently converted into unsaturated hydrocarbons by a catalyst in which a specific metal element is supported on a specific support, and the present invention has been completed.
  • One aspect of the present invention includes a step of bringing a raw material gas containing an alkane into contact with a dehydrogenation catalyst to obtain a product gas containing at least one unsaturated hydrocarbon selected from the group consisting of an olefin and a conjugated diene.
  • the present invention relates to a method for producing saturated hydrocarbons.
  • the dehydrogenation catalyst is a catalyst in which a carrier containing Al and a Group 2 metal element is supported on a carrier metal containing a Group 14 metal element and Pt, and is measured by the ammonia TPD method of the carrier.
  • the total acid amount is 15 ⁇ mol / g or less.
  • the total acid amount measured by the ammonia TPD method of the carrier may be 10 ⁇ mol / g or less.
  • the Group 14 metal element supported on the carrier may be Sn.
  • the raw material alkane may be an alkane having 4 to 10 carbon atoms.
  • the alkane may be butane, where the olefin may be butene and the conjugated diene may be butadiene.
  • a first step of bringing a raw material gas containing alkane into contact with a first dehydrogenation catalyst to obtain a first product gas containing olefin And a second step of obtaining a second product gas containing a conjugated diene by contacting with the dehydrogenation catalyst.
  • the first dehydrogenation catalyst is a catalyst in which a support containing Al and a Group 2 metal element is supported on a support metal containing a Group 14 metal element and Pt, and the ammonia TPD method of the support is used.
  • the total acid amount measured at is 15 ⁇ mol / g or less.
  • a novel method for producing unsaturated hydrocarbons there is provided a method for producing unsaturated hydrocarbons capable of efficiently obtaining unsaturated hydrocarbons from alkanes. Moreover, according to this invention, the manufacturing method of conjugated diene which can obtain a conjugated diene from alkane efficiently is provided.
  • the method for producing an unsaturated hydrocarbon includes a product gas containing at least one unsaturated hydrocarbon selected from the group consisting of an olefin and a conjugated diene by bringing a raw material gas containing an alkane into contact with a dehydrogenation catalyst.
  • the process (henceforth a dehydrogenation process) obtained.
  • the dehydrogenation catalyst is a catalyst in which a carrier containing Al and a Group 2 metal element is supported on a supported metal containing a Group 14 metal element and Pt. Further, the total acid amount of the carrier measured by the ammonia TPD method is 15 ⁇ mol / g or less.
  • an alkane by using a dehydrogenation catalyst in which a specific metal is supported on a specific support, an alkane can be reacted at a high conversion rate to obtain an unsaturated hydrocarbon.
  • the alkane may be, for example, a chain or a ring.
  • Examples of the chain alkane include butane, pentane, hexane, heptane, octane, decane, and the like.
  • examples of the linear alkane include n-butane, n-pentane, n-hexane, n-heptane, n-octane, and n-decane.
  • Examples of the branched alkane include isobutane, isopentane, 2-methylpentane, 3-methylpentane, 2,3-dimethylpentane, isoheptane, isooctane, and isodecane.
  • cyclic alkane examples include cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclodecane, and methylcyclohexane.
  • the source gas may contain one kind of alkane or two or more kinds.
  • the partial pressure of alkane may be 1.0 MPa or less, may be 0.1 MPa or less, or may be 0.01 MPa or less.
  • the alkane conversion rate can be further improved.
  • the partial pressure of alkane in the raw material gas is preferably 0.001 MPa or more, and more preferably 0.005 MPa or more, from the viewpoint of reducing the reactor size with respect to the raw material flow rate.
  • the raw material gas may further contain an inert gas such as nitrogen or argon.
  • the source gas may further contain steam.
  • the steam content is preferably 1.0 times mole or more, more preferably 1.5 times mole or more with respect to the alkane.
  • the catalyst activity may be more significantly suppressed.
  • content of a steam may be 50 times mole or less with respect to alkane, for example, Preferably it is 10 times mole or less.
  • olefins examples include butene, pentene, hexene, heptene, octene, nonene, decene, and the like, and these may be any isomers.
  • conjugated diene examples include 1,3-butadiene, 1,3-pentadiene, isoprene, 1,3-hexadiene, 1,3-heptadiene, 1,3-octadiene, 1,3-nonadiene, and 1,3-decadiene.
  • the product gas may contain one kind of unsaturated hydrocarbon, and may contain two or more kinds of unsaturated hydrocarbons.
  • the product gas may include olefins and conjugated dienes.
  • the dehydrogenation catalyst is a solid catalyst that catalyzes the dehydrogenation reaction of alkane, and is a catalyst in which a supported metal containing a Group 14 metal element and Pt is supported on a support containing Al and a Group 2 metal element.
  • the Group 2 metal element contained in the support may be at least one selected from the group consisting of Be, Mg, Ca, Sr and Ba.
  • the support may be, for example, a metal oxide support containing Al and a Group 2 metal element.
  • the metal oxide support may be, for example, a support containing alumina (Al 2 O 3 ) and a Group 2 metal oxide, or may be a composite oxide of Al and a Group 2 metal.
  • the total acid amount of the carrier is 15 ⁇ mol / g or less.
  • alkane can be converted to an unsaturated hydrocarbon at a high conversion rate.
  • the total acid amount of the carrier is preferably 10 ⁇ mol / g or less, and more preferably 6 ⁇ mol / g or less.
  • the total acid amount of the carrier may be 0.1 ⁇ mol / g or more, or 1.0 ⁇ mol / g or more.
  • the total acid amount of the carrier indicates the total amount of acid points of the carrier measured by the ammonia TPD method.
  • the ammonia TPD method can be carried out, for example, with the apparatus and measurement conditions described in “Niwa; Zeolite, 10, 175 (1993)”.
  • the specific surface area of the carrier may be, for example, 30 m 2 / g or more, and preferably 50 m 2 / g or more. Thereby, the effect of increasing the conversion rate of alkane is produced.
  • the specific surface area of the carrier may be, for example, 1000 m 2 / g or less, and preferably 500 m 2 / g or less. By having such a specific surface area, a carrier having sufficient strength that can be suitably used industrially can be obtained.
  • the method for preparing the carrier is not particularly limited, and may be, for example, a coprecipitation method, a deposition method, a kneading method, an impregnation method, a pore filling method, or the like.
  • the impregnation method or the pore filling method is preferable from the viewpoint of easily obtaining the above-mentioned preferable total acid amount.
  • a support is prepared by adding alumina to a solution in which an inorganic salt of a Group 2 metal is dissolved, stirring, removing the solvent under reduced pressure, drying and firing. Can do.
  • the dehydrogenation catalyst carries a supported metal containing a Group 14 metal element and Pt.
  • the Group 14 metal element may be at least one selected from the group consisting of Ge, Sn, and Pb, and is preferably Sn.
  • the amount of the Group 14 metal element supported may be, for example, 0.1 parts by mass or more with respect to 100 parts by mass of the support, and preferably 1.0 part by mass or more. Further, the supported amount of the Group 14 metal element may be, for example, 80 parts by mass or less, and preferably 50 parts by mass or less with respect to 100 parts by mass of the carrier. With such a supported amount, catalyst deterioration is further suppressed, and high activity tends to be maintained for a longer period of time.
  • the amount of Pt supported may be, for example, 0.01 parts by mass or more, preferably 0.1 parts by mass or more with respect to 100 parts by mass of the carrier. Further, the amount of Pt supported may be, for example, 5.0 parts by mass or less, preferably 3.0 parts by mass or less, with respect to 100 parts by mass of the carrier. With such a loading amount, the Pt particles formed on the catalyst have a size suitable for the dehydrogenation reaction, and the platinum surface area per unit platinum weight increases, so that a more efficient reaction system can be realized.
  • the supporting method of the supporting metal is not particularly limited, and examples thereof include an impregnation method, a deposition method, a coprecipitation method, a kneading method, an ion exchange method, and a pore filling method.
  • a carrier is added to a solution containing a supported metal precursor, and the solution is stirred. Thereafter, the solvent is removed under reduced pressure, and the solid obtained after drying is calcined, whereby the supported metal can be supported on the carrier.
  • the precursor of the supporting metal may be, for example, a metal salt or a complex.
  • the metal salt of the supported metal may be, for example, an inorganic salt, an organic acid salt, or a hydrate thereof.
  • Inorganic salts may be, for example, sulfates, nitrates, chlorides, phosphates, carbonates and the like.
  • the organic acid salt may be, for example, acetate, oxalate and the like.
  • the supported metal complex may be, for example, an alkoxide complex or an ammine complex.
  • the stirring temperature may be 0 to 60 ° C.
  • the stirring time may be 10 minutes to 24 hours.
  • the drying conditions may be, for example, a drying temperature of 100 to 250 ° C. and a drying time of 3 to 24 hours.
  • Calcination can be performed, for example, in an air atmosphere or an oxygen atmosphere. Firing may be performed in one stage, or may be performed in two or more stages.
  • the firing temperature may be any temperature that can decompose the precursor of the supported metal, and may be, for example, 200 to 1000 ° C., or may be 400 to 800 ° C.
  • at least one step should just be the said baking temperature.
  • the firing temperature at the other stage may be in the same range as described above, for example, and may be 100 to 200 ° C.
  • the dehydrogenation catalyst may further contain a molding aid from the viewpoint of improving moldability.
  • the molding aid may be, for example, a thickener, a surfactant, a water retention material, a plasticizer, a binder material, or the like.
  • the shape of the dehydrogenation catalyst is not particularly limited, and may be, for example, a pellet shape, a granule shape, a honeycomb shape, a sponge shape, or the like.
  • the dehydrogenation step is a step in which a raw material gas is brought into contact with a dehydrogenation catalyst to perform a dehydrogenation reaction of alkane to obtain a product gas containing unsaturated hydrocarbons.
  • the dehydrogenation step may be performed, for example, by using a reactor filled with a dehydrogenation catalyst and circulating a raw material gas through the reactor.
  • a reactor various reactors used for a gas phase reaction with a solid catalyst can be used. Examples of the reactor include a fixed bed reactor, a radial flow reactor, and a tubular reactor.
  • the reaction type of the dehydrogenation reaction may be, for example, a fixed bed type, a moving bed type, or a fluidized bed type.
  • the fixed bed type is preferable from the viewpoint of equipment cost.
  • the reaction temperature of the dehydrogenation reaction may be 300 to 800 ° C. or 500 to 700 ° C. from the viewpoint of reaction efficiency. If reaction temperature is 500 degreeC or more, there exists a tendency for the production amount of unsaturated hydrocarbon to increase further. If reaction temperature is 700 degrees C or less, there exists a tendency for high activity to be maintained over a long period of time.
  • the reaction pressure that is, the atmospheric pressure in the reactor may be 0.01 to 1 MPa, 0.05 to 0.8 MPa, or 0.1 to 0.5 MPa.
  • the reaction pressure is in the above range, the dehydrogenation reaction is more likely to proceed, and a further excellent reaction efficiency tends to be obtained.
  • the weight space velocity (hereinafter referred to as “WHSV”) may be 0.1 h ⁇ 1 or more, and 1.0 h it may also be -1 or more, may be at 100h -1 or less, may be 30h -1 or less.
  • WHSV is the ratio (supply rate / catalyst mass) of the feed rate (supply rate / time) of the raw material gas to the catalyst mass in a continuous reaction apparatus.
  • the usage amount of the raw material gas and the catalyst may be appropriately selected in a more preferable range according to the reaction conditions, the activity of the catalyst, etc., and WHSV is not limited to the above range.
  • the reactor may be further filled with a catalyst other than the dehydrogenation catalyst (hereinafter also referred to as the first dehydrogenation catalyst).
  • the production method includes contacting the product gas containing the olefin obtained in the dehydrogenation step (hereinafter also referred to as the first product gas) with the second dehydrogenation catalyst to dehydrate the olefin.
  • a step of performing an elementary reaction to obtain a second product gas containing a conjugated diene (hereinafter also referred to as a second dehydrogenation step) may be further provided. According to such a production method, a product gas containing more conjugated diene can be obtained.
  • any olefin dehydrogenation catalyst can be used without particular limitation.
  • a noble metal catalyst a catalyst containing Fe and K, a catalyst containing Mo and the like can be used.
  • Carrier Synthesis Example 1 ⁇ Preparation of carrier A-1> 15 g of alumina classified to 0.5 to 1 mm (Neobead GB-13, manufactured by Mizusawa Chemical Co., Ltd., pH of a suspension suspended in water at a concentration of 1% by mass: 7.9) A solution of .8 g Mg (NO 3 ) 2 .6H 2 O dissolved in 56 mL water was added. The obtained mixed solution was stirred at 40 ° C. and 0.015 MPaA for 30 minutes using a rotary evaporator, and stirred at 40 ° C. and normal pressure for 30 minutes. Thereafter, water was removed under reduced pressure while stirring the mixture. The resulting solid was dried in an oven at 130 ° C. overnight.
  • the dried solid was calcined at 550 ° C. for 3 hours and at 800 ° C. for 3 hours under air flow.
  • a solution obtained by dissolving 18.8 g of Mg (NO 3 ) 2 ⁇ 6H 2 O in 56 mL of water was again added to the obtained solid, and the same procedure was repeated to obtain carrier A-1.
  • the Mg content was 17.4% by mass based on the total mass of the carrier. Further, in the carrier A-1, the total acid amount was 5.9 ⁇ mol / g.
  • Carrier Synthesis Example 2 ⁇ Preparation of carrier A-2> 37 g of alumina classified to 0.5 to 1 mm (Neobead GB-13, manufactured by Mizusawa Chemical Industry Co., Ltd., pH of a suspension suspended in water at a concentration of 1% by mass: 7.9) A solution of .6 g Mg (NO 3 ) 2 .6H 2 O dissolved in 56 mL water was added. The obtained mixed solution was stirred at 40 ° C. and 0.015 MPaA for 30 minutes using a rotary evaporator, and stirred at 40 ° C. and normal pressure for 30 minutes. Thereafter, water was removed under reduced pressure while stirring the mixture. The resulting solid was dried in an oven at 130 ° C. overnight. Next, the solid after drying was calcined at 550 ° C. for 3 hours and at 800 ° C. for 3 hours under air flow to obtain carrier A-2.
  • the content of Mg was 17.2% by mass based on the total mass of the carrier. Further, in the carrier A-2, the total acid amount was 8.9 ⁇ mol / g.
  • Catalyst synthesis example 2 ⁇ Preparation of catalyst A-2> A catalyst was prepared in the same manner as in Catalyst Synthesis Example 1 except that Support A-2 was used instead of Support A-1, and Catalyst A-2 was obtained.
  • Carrier Synthesis Example 3 ⁇ Preparation of carrier A-3> 105.5 g of Al (NO 3 ) 3 .9H 2 O and 36.1 g of Mg (NO 3 ) 2 .6H 2 O were added to 1 L of ion-exchanged water and vigorously stirred. While stirring the aqueous solution, a solution obtained by diluting concentrated aqueous ammonia twice was added dropwise at a rate of 0.1 mL / s until pH 10 was reached, stirred for 30 minutes, and then allowed to stand for 30 minutes. The precipitate was filtered and washed with 1.3 L of ion exchange water twice. Subsequently, the obtained precipitate was dried in an oven at 130 ° C. overnight. Finally, the dried solid was calcined in three stages of 300 ° C. for 1 hour, 500 ° C. for 2 hours, and 800 ° C. for 4 hours under air flow to obtain carrier A-3.
  • the Mg content was 15.2% by mass based on the total mass of the carrier. Further, in the carrier A-3, the total acid amount was 10.6 ⁇ mol / g.
  • Catalyst Synthesis Example 3 ⁇ Preparation of catalyst A-3> A catalyst was prepared in the same manner as in Catalyst Synthesis Example 1 except that Support A-3 was used instead of Support A-1, and Catalyst A-3 was obtained.
  • Catalyst Synthesis Example 4 ⁇ Preparation of catalyst A-4> A catalyst was prepared in the same manner as in Catalyst Synthesis Example 1 except that alumina (Neobead GB-13, manufactured by Mizusawa Chemical Industry Co., Ltd.) classified to 0.5 to 1 mm was used as a support. Got. The total acid amount of alumina used as the carrier in Catalyst Synthesis Example 4 was 26.5 ⁇ mol / g.
  • a mixed gas raw material gas
  • the molar ratio of n-butane, N 2 and water in the raw material gas was adjusted to 1: 5: 3.
  • the feed rate of the raw material gas to the tubular reactor was adjusted to 62 mL / min.
  • the WHSV with respect to the total amount of the catalyst was adjusted to 1.0 h- 1 .
  • the pressure of the raw material gas in the tubular reactor was adjusted to atmospheric pressure.
  • the product (product gas) of the dehydrogenation reaction was collected from the tubular reactor. Further, when 300 minutes passed from the reaction start time, the product (product gas) of the dehydrogenation reaction was collected from the tubular reactor.
  • the reaction start time is the time when the supply of the source gas is started.
  • the product gas collected at each time point was analyzed using a gas chromatograph (TCD-GC) equipped with a thermal conductivity detector. As a result of analysis, it was confirmed that the product gas contains butene and 1,3-butadiene. Based on the gas chromatograph, the butene concentration (unit: mass%) and the butadiene concentration (unit: mass%) in the product gas collected at each time point were quantified.
  • the butane conversion rate is defined by the following formula (1)
  • the butadiene yield is defined by the following formula (2)
  • the butene yield is defined by the following formula (3).
  • R Y1 M a / M 0 ⁇ 100 (1)
  • R Y2 M b / M 0 ⁇ 100 (2)
  • R Y3 M P / M 0 ⁇ 100 (3)
  • R Y1 in Formula (1) is a butane conversion
  • M 0 is the number of moles of n- butane in the feed gas
  • M a is the number of moles of n- butane in the product gas.
  • R Y1 is the butadiene yield
  • M 0 is the number of moles of n-butane in the raw material gas
  • M b is the number of moles of 1,3-butadiene in the product gas.
  • the butane conversion rate, butene yield and butadiene yield after 60 minutes were 64.7%, 51.2%, 9.8%, butane conversion rate and butene yield after 360 minutes, respectively.
  • the rate and butadiene yield were 58.7%, 46.3%, and 9.6%, respectively.
  • Example 2 The dehydrogenation reaction of n-butane and the analysis of the product gas were performed in the same manner as in Example 1 except that the catalyst A-2 was used instead of the catalyst A-1.
  • the butane conversion rate, butene yield and butadiene yield after 60 minutes from the start of the reaction were 66.9%, 53.4%, 8.8%, butane conversion rate and butene yield after 360 minutes, respectively.
  • the rate and butadiene yield were 59.0%, 46.9%, and 9.0%, respectively.
  • Example 3 The dehydrogenation reaction of n-butane and the analysis of the product gas were performed in the same manner as in Example 1 except that the catalyst A-3 was used instead of the catalyst A-1.
  • the butane conversion rate, butene yield and butadiene yield after 60 minutes from the start of the reaction were 42.3%, 34.3%, 6.0%, butane conversion rate and butene yield after 360 minutes, respectively.
  • the rate and butadiene yield were 35.2%, 27.9%, and 5.6%, respectively.
  • Table 1 shows the results of Examples 1 to 3 and Comparative Example 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract

L'invention concerne un procédé de fabrication d'hydrocarbure insaturé qui comporte une étape au cours de laquelle un gaz matière de départ contenant un alcane est mis en contact avec un catalyseur de déshydrogénation, permettant ainsi d'obtenir un gaz produit contenant au moins une sorte d'hydrocarbure insaturé choisie parmi un groupe constitué d'oléfine et de diène conjugué. Le catalyseur de déshydrogénation supporte sur un support contenant un Al et un élément métallique du groupe 2, un métal supporté contenant un élément métallique du groupe 14 et un Pt. L'acidité totale du support mesurée par désorption à température programmée d'ammoniac, est inférieure ou égale à １５μｍｏｌ／ｇ.
PCT/JP2017/005145 2016-02-12 2017-02-13 Procédé de fabrication d'hydrocarbure insaturé, et procédé de fabrication de diène conjugué WO2017138667A1 (fr)

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