WO2019176247A1 - Procédé de fabrication d'indane - Google Patents

Procédé de fabrication d'indane Download PDF

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Publication number
WO2019176247A1
WO2019176247A1 PCT/JP2019/000250 JP2019000250W WO2019176247A1 WO 2019176247 A1 WO2019176247 A1 WO 2019176247A1 JP 2019000250 W JP2019000250 W JP 2019000250W WO 2019176247 A1 WO2019176247 A1 WO 2019176247A1
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Prior art keywords
dehydrogenation
dehydrogenation catalyst
tetrahydroindene
platinum
catalyst
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PCT/JP2019/000250
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English (en)
Japanese (ja)
Inventor
信啓 木村
瀬川　敦司
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Ｊｘｔｇエネルギー株式会社
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Publication of WO2019176247A1 publication Critical patent/WO2019176247A1/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
    • B01J23/54—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
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
    • C07C13/465—Indenes; Completely or partially hydrogenated indenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/24—Polycyclic condensed hydrocarbons containing two rings
    • 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
    • C07C5/367—Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
    • 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
    • C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
    • 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 indan.
  • INDAN is an industrially useful substance as a synthetic raw material for pharmaceuticals and chemicals or as a metallocene catalyst component.
  • THI tetrahydroindene
  • An object of the present invention is to provide a method for producing indane, which is a novel method for producing indane, in which tetrahydroindene is less diluted and tetrahydroindene can be efficiently dehydrogenated at a low temperature and in a short time.
  • the present inventors have found that a specific dehydrogenation catalyst and a specific reaction condition exhibit excellent dehydrogenation activity and high indane selectivity in tetrahydroindene dehydrogenation, and complete the present invention. It came.
  • One aspect of the present invention is a method for producing indan comprising a dehydrogenation step in which a raw material composition containing tetrahydroindene is brought into contact with a dehydrogenation catalyst under a temperature condition of 150 to 300 ° C. to obtain a reaction product containing indan.
  • the dehydrogenation catalyst includes a carrier containing aluminum, a Group 14 metal element and platinum supported on the carrier, and the Group 14 metal element with respect to the platinum in the dehydrogenation catalyst.
  • the atomic ratio of is 9.0 or more.
  • the molar fraction of the tetrahydroindene in the raw material composition may be 0.2 or more.
  • the Group 14 metal element may be tin.
  • the platinum content in the dehydrogenation catalyst may be 1% by mass or more based on the total amount of the dehydrogenation catalyst.
  • the raw material composition in the dehydrogenation step, may be brought into contact with the dehydrogenation catalyst under a pressure condition of 0.1 to 4.0 MPa.
  • the raw material composition in the dehydrogenation step, may be brought into contact with the dehydrogenation catalyst under the condition that the tetrahydroindene becomes a liquid.
  • the Group 14 metal element and the platinum may be supported on the carrier using a metal source that does not contain a chlorine atom.
  • a raw material synthesis step for obtaining tetrahydroindene by reacting butadiene with cyclopentadiene may be further provided.
  • a new method for producing indane there is provided a method for producing indane, in which tetrahydroindene is less diluted and tetrahydroindene can be efficiently dehydrogenated at a low temperature and in a short time.
  • the indane production method includes a dehydrogenation step in which a raw material composition containing tetrahydroindene is brought into contact with a dehydrogenation catalyst under a temperature condition of 150 to 300 ° C. to obtain a reaction product containing indane. ing.
  • the dehydrogenation catalyst includes a carrier containing aluminum, a Group 14 metal element and platinum supported on the carrier, and the atomic ratio of the Group 14 metal element to platinum in the dehydrogenation catalyst is 9 0.0 or more.
  • the production method by adopting a specific dehydrogenation catalyst and a specific temperature condition, dehydrogenation is achieved even under conditions where the dilution of tetrahydroindene is small, energy consumption is low, and the temperature is short. Since the conversion rate of tetrahydrindene and the selectivity of indane in the reaction are increased, indane can be obtained in high yield and the dehydrogenation efficiency of tetrahydroindene is improved.
  • the dehydrogenation catalyst used in the present embodiment is a catalyst containing a carrier containing aluminum and a Group 14 metal element and platinum supported on the carrier.
  • the Group 14 metal element means a metal element belonging to Group 14 of the periodic table in the periodic table of long-period elements based on the provisions of IUPAC (International Pure Applied Chemistry Association).
  • Examples of the Group 14 metal element include tin (Sn) and lead (Pb).
  • the method for preparing the dehydrogenation catalyst is not particularly limited, and may be a method of further supporting platinum after supporting the Group 14 metal element on the support. After supporting the platinum on the support, the Group 14 metal is supported. It may be a method of further supporting an element, or a method of simultaneously supporting a Group 14 metal element and platinum on a carrier.
  • the carrier containing aluminum, the Group 14 metal element, and platinum may each exist as an oxide, or may exist as a complex oxide with other metals, and may be a metal salt or a metal simple substance. May exist as
  • the dehydrogenation catalyst may contain other metal elements in addition to aluminum, a Group 14 metal element and platinum.
  • other metal elements include lithium (Li), sodium (Na), potassium (K), magnesium (Mg), calcium (Ca), zinc (Zn), iron (Fe), indium (In), and selenium. (Se), antimony (Sb), nickel (Ni), gallium (Ga), and the like.
  • the dehydrogenation catalyst may be a catalyst in which a support metal including aluminum is supported on a support metal including a Group 14 metal element and platinum. In another embodiment, the dehydrogenation catalyst may be a catalyst in which an active metal containing platinum is supported on a support containing aluminum and a Group 14 metal element.
  • the support is preferably an inorganic oxide support containing aluminum.
  • the inorganic oxide containing aluminum may be an oxide containing aluminum as a metal, or may be a composite oxide of aluminum and another metal.
  • As an oxide containing aluminum as a metal for example, alumina (Al 2 O 3 ) may be used.
  • composite oxides of aluminum and other metals include composite oxides of aluminum and magnesium (Mg), composite oxides of aluminum and tin (Sn), and composite oxides of aluminum and lead (Pb).
  • a composite oxide of aluminum and zinc (Zn), selenium (Se), iron (Fe), indium (In), or the like may be used.
  • the inorganic oxide carrier containing aluminum examples include a carrier containing an inorganic oxide such as alumina, alumina magnesia, silica alumina, zirconia alumina, and spinel structure (magnesium spinel).
  • the aluminum content in the carrier may be 25% by mass or more based on the total amount of the carrier, and is preferably 50% by mass or more.
  • 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 conversion rate of indan tends to be further improved.
  • 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. Thereby, it can be set as the support
  • the specific surface area of the carrier is measured by a BET specific surface area meter using a nitrogen adsorption method.
  • the method for preparing the carrier is not particularly limited, and examples thereof include a sol-gel method, a coprecipitation method, and a hydrothermal synthesis method.
  • the platinum content in the dehydrogenation catalyst may be 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1.0% by mass or more, based on the total amount of the dehydrogenation catalyst.
  • the supported amount of platinum is preferably 5.0% by mass or less, more preferably 3.0% by mass or less, based on the total amount of the dehydrogenation catalyst. With such a supported amount, the platinum particles formed on the catalyst are likely to 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 atomic ratio of the Group 14 metal element to platinum in the dehydrogenation catalyst is 9.0 or more.
  • the ratio is preferably 500 or less, and more preferably 100 or less. If the ratio is in the above range, the yield of indane tends to be further improved.
  • the content of the Group 14 metal element in the dehydrogenation catalyst is not particularly limited, and may be appropriately changed within a range that satisfies the above ratio, for example.
  • the amount of the Group 14 metal element supported is, for example, 15% by mass or more, preferably 20% by mass or more, based on the total amount of the dehydrogenation catalyst. Further, the supported amount of the Group 14 metal element is, for example, 45% by mass or less, preferably 40% by mass or less, based on the total amount of the dehydrogenation catalyst.
  • the group 14 metal element in the dehydrogenation catalyst may be at least one selected from the group consisting of germanium (Ge), tin (Sn), and lead (Pb), for example.
  • germanium Ge
  • tin Sn
  • Pb lead
  • the dehydrogenation catalyst may be one in which platinum and tin are supported on a carrier using a platinum source and a tin source.
  • platinum source include tetraammineplatinum (II) acid, tetraammineplatinum (II) acid salt (eg, nitrate), tetraammineplatinum (II) acid hydroxide solution, dinitrodiammine platinum (II) nitric acid solution, hexahydroxo
  • Examples thereof include a platinum (IV) acid nitric acid solution and a hexahydroxoplatinum (IV) acid ethanolamine solution.
  • the tin source include sodium stannate and potassium stannate.
  • a metal source which does not contain a chlorine atom As a platinum source and a tin source, it is preferable to use a metal source which does not contain a chlorine atom. By using a metal source that does not contain a chlorine atom, corrosion of the apparatus can be suppressed and tetrahydroindene can be dehydrogenated more efficiently.
  • 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 precursor of a supported metal (Group 14 metal element source and platinum source), and the carrier containing the solution is kneaded. Thereafter, the solvent is removed by drying, and the obtained solid is fired, whereby the supported metal can be supported on the support.
  • a supported metal Group 14 metal element source and platinum source
  • 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 be formed by a method such as an extrusion method or a tableting method.
  • the dehydrogenation catalyst may further contain a molding aid as long as the physical properties and catalyst performance of the catalyst are not impaired from the viewpoint of improving the moldability.
  • the molding aid may be at least one selected from the group consisting of thickeners, surfactants, water retention agents, plasticizers, binder raw materials, and the like.
  • the molding process for molding the dehydrogenation catalyst may be performed at an appropriate stage of the dehydrogenation catalyst manufacturing process in consideration of the reactivity of the molding aid.
  • the shape of the dehydrogenation catalyst is not particularly limited, and can be appropriately selected depending on the form in which the catalyst is used.
  • the shape of the dehydrogenation catalyst may be a pellet shape, a granule shape, a honeycomb shape, a sponge shape, or the like.
  • a dehydrogenation catalyst that has been subjected to a reduction treatment as a pretreatment may be used.
  • the reduction treatment can be performed, for example, by holding the dehydrogenation catalyst at 40 to 600 ° C. in a reducing gas atmosphere.
  • the holding time may be, for example, 0.05 to 24 hours.
  • the reducing gas may contain hydrogen, carbon monoxide, etc., for example.
  • the raw material composition containing tetrahydroindene is brought into contact with the dehydrogenation catalyst under a temperature condition of 150 to 300 ° C. Thereby, dehydrogenation reaction of tetrahydroindene occurs, and a reaction product containing indane is obtained.
  • the raw material composition may further contain components other than tetrahydroindene.
  • the raw material composition may further contain inert gas such as nitrogen and argon, steam, hydrogen, oxygen, carbon monoxide, carbon dioxide gas, alkanes, olefins and the like.
  • the molar fraction of tetrahydroindene in the raw material composition is preferably 0.2 or more.
  • the molar fraction of tetrahydroindene in the raw material composition is more preferably 0.25 or more.
  • the upper limit of the molar fraction of tetrahydroindene in the raw material composition is not particularly limited, but may be, for example, 0.95 or less, and preferably 0.9 or less.
  • the dehydrogenation step may be performed, for example, by using a reactor filled with a dehydrogenation catalyst and circulating the raw material product 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 adiabatic 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 temperature at which the raw material composition is brought into contact with the dehydrogenation catalyst is the reaction temperature of the dehydrogenation reaction, and can also be referred to as the temperature in the reactor. If the reaction temperature of the dehydrogenation reaction is 300 ° C. or lower, side reactions are suppressed, and the yield of indane tends to be further improved. If the reaction temperature of the dehydrogenation reaction is 150 ° C. or higher, the dehydrogenation reaction of tetrahydroindene proceeds sufficiently, and the yield of indane tends to increase.
  • the pressure condition for bringing the raw material composition into contact with the dehydrogenation catalyst may be, for example, 0.01 to 20.0 MPa, 0.05 to 10.0 MPa, It may be 1 to 4.0 MPa.
  • the dehydrogenation reaction is likely to proceed when the reaction pressure is low.
  • the reaction pressure is within the above range, the dehydrogenation reaction is likely to proceed, resulting in higher reaction efficiency. There is a tendency to be obtained.
  • the condition for bringing the raw material composition into contact with the dehydrogenation catalyst may be a condition in which tetrahydroindene becomes liquid. If the inside of the reactor satisfies the above conditions, the yield of indane will be higher. For example, it is sufficient that the tetrahydroindene is liquefied, and the atmospheric pressure in the reactor can be appropriately adjusted according to the temperature in the reactor, and the temperature in the reactor depends on the atmospheric pressure in the reactor. It can be adjusted appropriately.
  • the liquid space velocity (hereinafter referred to as “LHSV”) may be 0.01 h ⁇ 1 or more, and 0.1 h ⁇ One or more may be sufficient. With such LHSV, the conversion rate of tetrahydroindene can be further increased. Also, LHSV may be in 100h -1 or less, may be 20h -1 or less. When LHSV is in the above range, the reactor size can be further reduced.
  • LHSV is the ratio (F / L) of the feed rate (feed rate / time) F of the raw material to the capacity L of the dehydrogenation catalyst in the continuous reaction apparatus.
  • the usage-amount of a raw material and a catalyst may select the more preferable range suitably according to reaction conditions, the activity of a catalyst, etc., and LHSV is not limited to the said range.
  • the reactor may be further filled with a catalyst other than the above dehydrogenation catalyst (hereinafter also referred to as “first dehydrogenation catalyst”).
  • a solid catalyst (hereinafter also referred to as “second dehydrogenation catalyst”) that catalyzes the dehydrogenation reaction from indane to indene is further provided after the first dehydrogenation catalyst of the reactor. It may be filled.
  • the first dehydrogenation catalyst is particularly excellent in the reaction activity of the dehydrogenation reaction from tetrahydroindene to indane. Therefore, by filling the second dehydrogenation catalyst after the first dehydrogenation catalyst, the tetrahydroindene is converted into indene. Can be manufactured more efficiently.
  • any catalyst can be used as long as it is a catalyst for indane dehydrogenation.
  • the second dehydrogenation catalyst chromium / Al 2 O 3 catalyst, platinum / Al 2 O 3 catalyst, Fe—K catalyst, oxidative dehydrogenation catalyst often used as a catalyst for dehydrogenation reaction Bi-Mo based catalysts that are often used can be used.
  • the production method according to the present embodiment may further include a raw material synthesis step of obtaining tetrahydroindene by reacting butadiene and cyclopentadiene.
  • the raw material synthesis step may be provided, for example, before the dehydrogenation step.
  • the tetrahydroindene has a high conversion rate and a high indane selectivity even under conditions where the dilution of tetrahydroindene is low, the reaction temperature is low, and the energy consumption is low for a short time. Dehydrogenation can be performed. Therefore, according to the manufacturing method according to the present embodiment, indane can be efficiently manufactured from tetrahydroindene. Further, the catalyst does not contain chlorine, and is suitable for industrial production. For these reasons, the manufacturing method according to the present embodiment is very useful when industrially producing indan.
  • Catalyst synthesis example 2 A catalyst was prepared in the same manner as in Catalyst Synthesis Example 1 except that platinum was impregnated and supported on the alumina-tin oxide support A so that the platinum content was 3.0% by mass to obtain a dehydrogenation catalyst A-2. It was.
  • Catalyst Synthesis Example 3 A catalyst was prepared in the same manner as in Catalyst Synthesis Example 1 except that platinum was impregnated and supported on alumina-tin oxide support A so that the amount of platinum supported was 0.5% by mass to obtain dehydrogenation catalyst A-3. It was.
  • an aqueous solution obtained by dissolving 1.60 g of sodium stannate (manufactured by Kishida Chemical Co., Ltd., Na 2 SnO 3 .3H 2 O) in 20 ml of water was mixed, dried at 130 ° C. overnight, and then at 550 ° C. for 3 hours. Firing was performed. Thereafter, by repeatedly washing with water, tin was impregnated and supported so that the tin content was 12.1% by mass to obtain an alumina-tin oxide carrier B.
  • the platinum was impregnated and supported so as to be 3.0% by mass, dried at 130 ° C. overnight, and calcined at 550 ° C. for 3 hours to obtain a dehydrogenation catalyst B-1.
  • the reaction product of the dehydrogenation reaction was collected from the tubular reactor when 120 minutes and 180 minutes passed from the start of the reaction.
  • the reaction start time is the time when the supply of the raw material composition is started.
  • the collected product was analyzed using a gas chromatograph (Agilent, GC-7890, FID-GC) equipped with a hydrogen flame detector. Based on the gas chromatograph, each component (unit: mass%) of the collected reaction product was quantified. The results are shown in Table 1.
  • the conversion rate of tetrahydroindene is defined by the following formula (1)
  • the selectivity of indane is defined by formula (2)
  • the yield of indane is defined by formula (3).
  • RC in Formula (1) is the conversion rate (%) of tetrahydroindene.
  • RS in Formula (2) is the selectivity (%) of indane.
  • RY in Formula (3) is the yield (%) of indane.
  • m0 is the number of moles of tetrahydroindene in the raw material composition.
  • M1 in the formulas (1) and (2) is the number of moles of tetrahydroindene in the reaction product.
  • M2 in the formulas (2) and (3) is the number of moles of indane in the reaction product.
  • Example 2 The same procedure as in Example 1 was performed except that the dehydrogenation catalyst A-2 was used in place of the dehydrogenation catalyst A-1 and the reaction pressure was 0.4 MPa. The results are shown in Table 1.
  • Example 3 Example except that the dehydrogenation catalyst A-2 was used instead of the dehydrogenation catalyst A-1, and the reaction product of the dehydrogenation reaction was collected from the tubular reactor only when 120 minutes had elapsed from the start of the reaction. 1 was performed. The results are shown in Table 1.
  • Example 4 The same procedure as in Example 1 was performed except that dehydrogenation catalyst A-3 was used instead of dehydrogenation catalyst A-1. The results are shown in Table 1.
  • Example 5 3.7 cc of dehydrogenation catalyst A-2 was charged into a tubular reactor, and the reaction tube was connected to a fixed bed flow type reactor. After raising the temperature of the reaction tube to 180 ° C., hydrogen was circulated at 99 mL / min for 30 minutes while maintaining the temperature. Thereafter, tetrahydroindene (manufactured by Tokyo Chemical Industry Co., Ltd.), N 2 and steam (water) were respectively supplied to the reactor, and tetrahydroindene was dehydrogenated at a reaction temperature of 180 ° C. and 0.15 MPa.
  • the LHSV was set to 1.8h- 1 . Under these reaction conditions, tetrahydroindene in the raw material composition is liquid.
  • the reaction product of the dehydrogenation reaction was collected from the tubular reactor when 120 minutes and 180 minutes passed from the start of the reaction.
  • the reaction start time is the time when the supply of the raw material composition is started.
  • the collected reaction product was analyzed using a gas chromatograph (Agilent, GC-7890, FID-GC) equipped with a hydrogen flame detector. Based on the gas chromatograph, each component (unit: mass%) of the collected reaction product was quantified. The results are shown in Table 1.
  • Example 2 The same procedure as in Example 3 was performed except that the reaction temperature was 470 ° C. and the LHSV was 2.4 h ⁇ 1 . The results are shown in Table 2.
  • Example 3 The same procedure as in Example 1 was performed except that the dehydrogenation catalyst A-2 was used in place of the dehydrogenation catalyst A-1, the reaction temperature was 310 ° C., and the reaction pressure was 0.1 MPa. The results are shown in Table 2.
  • Example 4 The reaction was performed in the same manner as in Example 5 except that the reaction temperature was 140 ° C. In this reaction condition, tetrahydroindene in the raw material composition is liquid. The results are shown in Table 2.
  • tetrahydroindene manufactured by Tokyo Chemical Industry Co., Ltd.
  • N 2 and steam (water) were respectively supplied to the reactor, and tetrahydroindene was dehydrogenated at a reaction temperature of 260 ° C. and 0.2 MPa.
  • the LHSV was set to 1.8h- 1 .
  • the reaction product of the dehydrogenation reaction was collected from the tubular reactor when 120 minutes and 180 minutes passed from the start of the reaction.
  • the reaction start time is the time when the supply of raw materials is started.
  • the collected reaction product was analyzed using a gas chromatograph (Agilent, GC-7890, FID-GC) equipped with a hydrogen flame detector. Based on the gas chromatograph, each component (unit: mass%) of the collected reaction product was quantified. The results are shown in Table 2.
  • indane as a new method for producing indane, it is possible to provide a method for producing indane, in which tetrahydroindene is less diluted and tetrahydroindene can be efficiently dehydrogenated at a low temperature and in a short time.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract

L'invention concerne un procédé de fabrication d'indane qui comporte une étape de déshydrogénation au cours de laquelle une composition de matière de départ contenant un tétrahydroindène est mise en contact avec un catalyseur de déshydrogénation sous des conditions de température comprise entre 150 et 300°C, et un produit de réaction contenant un indane est obtenu. Ledit catalyseur de déshydrogénation contient un support contenant un aluminium, et un élément métallique du groupe 14 ainsi qu'une platine supportés par ce support. Le rapport atomique dudit élément métallique du groupe 14 vis-à-vis de ladite platine dans ledit catalyseur de déshydrogénation, est supérieur ou égal à 9,0.
PCT/JP2019/000250 2018-03-13 2019-01-08 Procédé de fabrication d'indane WO2019176247A1 (fr)

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Cited By (2)

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WO2022154048A1 (fr) * 2021-01-15 2022-07-21 Ｅｎｅｏｓ株式会社 Procédé de production d'indane et d'hydrindane
CN115385770A (zh) * 2022-10-10 2022-11-25 安徽金禾化学材料研究所有限公司 一种制备1,1,2,3,3-五甲基-4,5,6,7-四氢茚满的方法

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WO2022154048A1 (fr) * 2021-01-15 2022-07-21 Ｅｎｅｏｓ株式会社 Procédé de production d'indane et d'hydrindane
CN115385770A (zh) * 2022-10-10 2022-11-25 安徽金禾化学材料研究所有限公司 一种制备1,1,2,3,3-五甲基-4,5,6,7-四氢茚满的方法
CN115385770B (zh) * 2022-10-10 2023-10-03 安徽金禾化学材料研究所有限公司 一种制备1,1,2,3,3-五甲基-4,5,6,7-四氢茚满的方法

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