WO2023145941A1 - エタノールの変換方法、及びその他炭化水素の製造方法 - Google Patents

エタノールの変換方法、及びその他炭化水素の製造方法 Download PDF

Info

Publication number
WO2023145941A1
WO2023145941A1 PCT/JP2023/002899 JP2023002899W WO2023145941A1 WO 2023145941 A1 WO2023145941 A1 WO 2023145941A1 JP 2023002899 W JP2023002899 W JP 2023002899W WO 2023145941 A1 WO2023145941 A1 WO 2023145941A1
Authority
WO
WIPO (PCT)
Prior art keywords
ethanol
fraction
catalyst
reaction
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2023/002899
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
鉄平 浦山
隆介 宮崎
隆 角田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Asahi Kasei Corp
Asahi Chemical Industry Co Ltd
Original Assignee
Asahi Kasei Corp
Asahi Chemical Industry Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2022137041A external-priority patent/JP2024121026A/ja
Application filed by Asahi Kasei Corp, Asahi Chemical Industry Co Ltd filed Critical Asahi Kasei Corp
Priority to KR1020247025726A priority Critical patent/KR20240131407A/ko
Priority to CA3248274A priority patent/CA3248274A1/en
Priority to JP2023577073A priority patent/JP7752192B2/ja
Priority to CN202380019397.6A priority patent/CN118647592A/zh
Priority to EP23747151.1A priority patent/EP4474371A4/en
Publication of WO2023145941A1 publication Critical patent/WO2023145941A1/ja
Anticipated expiration legal-status Critical
Priority to JP2025123845A priority patent/JP2025157508A/ja
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
    • 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
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/04—Ethene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/06—Propene
    • 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
    • C07C11/02—Alkenes
    • C07C11/10—Alkenes with five carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/107—Alkenes with six 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
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/12—Alkadienes
    • C07C11/173—Alkadienes with five carbon atoms
    • C07C11/18—Isoprene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/04—Benzene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/06—Toluene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/067—C8H10 hydrocarbons
    • C07C15/08—Xylenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
    • C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
    • C07C15/46—Styrene; Ring-alkylated styrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/18—Preparation of carboxylic acid nitriles by reaction of ammonia or amines with compounds containing carbon-to-carbon multiple bonds other than in six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
    • C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
    • C07C255/07—Mononitriles
    • C07C255/08—Acrylonitrile; Methacrylonitrile
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
    • C07C4/06—Catalytic processes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/02—Ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/04—Monomers containing three or four carbon atoms
    • C08F10/06—Propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/06—Hydrocarbons
    • C08F12/08—Styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/42—Nitriles
    • C08F20/44—Acrylonitrile
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G9/34—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils by direct contact with inert preheated fluids, e.g. with molten metals or salts
    • C10G9/36—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils by direct contact with inert preheated fluids, e.g. with molten metals or salts with heated gases or vapours
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/40—Ethylene production

Definitions

  • the content of elemental phosphorus in the catalyst indicates a value measured using a fluorescent X-ray spectrometer.
  • the content of elemental phosphorus can be measured using a commercially available fluorescent X-ray analyzer under normal conditions according to the instruction manual. Measurement conditions can be a tube voltage of 50 kV and a tube current of 50 mA using P-K ⁇ rays.
  • the content of elemental silver in the catalyst indicates a value measured using a fluorescent X-ray spectrometer.
  • the content of elemental silver can be measured using a commercially available fluorescent X-ray analyzer under normal conditions according to the instruction manual. Measurement conditions can be a tube voltage of 50 kV and a tube current of 50 mA using P-K ⁇ rays.
  • a separation step In the separation step, the target compound is separated from the reaction gas.
  • a separation step can separate ethylene, propylene and aromatic compounds from the reaction gas.
  • the recycling step at least part of the fraction A is recycled to the reaction step as part of the mixed raw material.
  • the fraction C obtained from the cooling step is the first distillation column 2, and the fraction A mainly containing hydrocarbons having 1 to 3 carbon atoms and the fraction mainly containing hydrocarbons having 4 to 6 carbon atoms.
  • B Furthermore, by supplying the fraction A to the second distillation column 8, the fraction A is a fraction A-1 mainly containing hydrocarbons having 2 carbon atoms and a fraction A-1 mainly containing hydrocarbons having 3 carbon atoms.
  • A-2 By using the fraction A-1 as a recycled raw material, the propylene concentration in the mixed raw material is lowered, and propylene can be produced efficiently.
  • the method for producing hydrocarbons according to the present embodiment includes contacting a mixed raw material containing ethylene and ethanol with a catalyst in an adiabatic reactor to obtain a reaction gas containing an olefin having 3 or more carbon atoms. .
  • the details of the production method are as described in the above ethanol conversion method, and the preferred embodiments thereof are also the same.
  • the method for producing propylene according to this embodiment includes: a propylene separation step of separating a fraction mainly containing propylene from the reaction gas obtained by the ethanol conversion method; including.
  • the method for producing an acrylonitrile-based polymer according to this embodiment includes: A step of polymerizing a polymerizable composition containing acrylonitrile obtained by the method for producing acrylonitrile described above; including.
  • the polymerizable composition may contain acrylonitrile alone as a monomer, or may contain other monomers having unsaturated bonds.
  • Effective raw material supply mass flow rate (kg/hr) Ethylene flow rate (kg/hr) + Ethylene conversion ethanol flow rate (kg/hr) + C4-C6 olefin flow rate (kg/hr) + Carbon numbers other than ethanol from 1 to 6 oxygenate flow rate (kg/hr)
  • Effective raw material supply mass flow rate (kg/hr) Ethylene flow rate (kg/hr) + Ethylene conversion ethanol flow rate (kg/hr) + C4-C6 olefin flow rate (kg/hr) + Carbon numbers other than ethanol from 1 to 6 oxygenate flow rate (kg/hr)
  • a mixed feed gas ethylene 1.0 kg/hr, ethanol 4.6 kg/hr, steam 0.7 kg/hr
  • the raw material introduced into the reactor 1 has an ethylene/ethanol molar ratio of 0.80 and an olefin having 4 to 6 carbon atoms/ethylene molar ratio of 0.23.
  • Table 9 shows the composition of the components (mainly hydrocarbons having 4 or more carbon atoms) recycled from the fraction B contained in the raw material.
  • the average propylene yield from the start of the reaction to the end of the reaction is 24.5% by mass, and the coke yield of the zeolite-containing catalyst after 48 hours of operation is 321 mass ppm.
  • the recovery yield of propylene obtained at the outlet of the separation step is 14.8% by mass, and the recovery yield of aromatic compounds is 13.4% by mass.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Materials Engineering (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/JP2023/002899 2022-01-31 2023-01-30 エタノールの変換方法、及びその他炭化水素の製造方法 Ceased WO2023145941A1 (ja)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020247025726A KR20240131407A (ko) 2022-01-31 2023-01-30 에탄올의 변환 방법 및 그 외 탄화수소의 제조 방법
CA3248274A CA3248274A1 (en) 2022-01-31 2023-01-30 ETHANOL CONVERSION PROCESS AND PROCESS FOR PRODUCING ANOTHER HYDROCARBON
JP2023577073A JP7752192B2 (ja) 2022-01-31 2023-01-30 エタノールの変換方法、及びその他炭化水素の製造方法
CN202380019397.6A CN118647592A (zh) 2022-01-31 2023-01-30 乙醇的转化方法和其它烃的制造方法
EP23747151.1A EP4474371A4 (en) 2022-01-31 2023-01-30 ETHANOL CONVERSION PROCESS AND PROCESS FOR PRODUCING ANOTHER HYDROCARBON
JP2025123845A JP2025157508A (ja) 2022-01-31 2025-07-24 エタノールの変換方法、及びその他炭化水素の製造方法

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2022-012969 2022-01-31
JP2022012969 2022-01-31
JP2022088596 2022-05-31
JP2022-088596 2022-05-31
JP2022-137041 2022-08-30
JP2022137041A JP2024121026A (ja) 2022-08-30 2022-08-30 エタノール及びエチレンの変換方法、プロピレンの製造方法、芳香族化合物の製造方法、並びに、エタノール及びエチレンの変換装置

Publications (1)

Publication Number Publication Date
WO2023145941A1 true WO2023145941A1 (ja) 2023-08-03

Family

ID=87471695

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/002899 Ceased WO2023145941A1 (ja) 2022-01-31 2023-01-30 エタノールの変換方法、及びその他炭化水素の製造方法

Country Status (6)

Country Link
EP (1) EP4474371A4 (https=)
JP (2) JP7752192B2 (https=)
KR (1) KR20240131407A (https=)
CA (1) CA3248274A1 (https=)
TW (1) TWI900821B (https=)
WO (1) WO2023145941A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024070182A1 (ja) * 2022-09-30 2024-04-04 旭化成株式会社 エタノールの変換方法、炭化水素の製造方法、プロピレンの製造方法、芳香族化合物の製造方法、及び、エタノールの変換装置

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5436203A (en) * 1977-08-09 1979-03-16 Petroleo Brasileiro Sa Process for preparing ethene
WO2005056504A1 (ja) 2003-12-12 2005-06-23 Mitsubishi Chemical Corporation プロピレンの製造方法
JP2007502796A (ja) * 2003-08-19 2007-02-15 トータル・ペトロケミカルズ・リサーチ・フエリユイ オレフィンの生産
JP2007291076A (ja) * 2006-03-30 2007-11-08 Mitsubishi Chemicals Corp プロピレンの製造方法
JP2007290991A (ja) * 2006-04-24 2007-11-08 Idemitsu Kosan Co Ltd 含酸素化合物からのオレフィン類の製造方法
US20110288358A1 (en) * 2008-12-11 2011-11-24 Lurgi Gmbh Method for producing a product containing c3h6 and c2h4
US20130245290A1 (en) * 2011-09-07 2013-09-19 Shell Oil Company Process for preparing ethylene and propylene
US20140018593A1 (en) 2011-03-23 2014-01-16 Lurgi Gmbh Process and plant for the production of low-molecular olefins
WO2014025021A1 (ja) 2012-08-10 2014-02-13 旭化成ケミカルズ株式会社 オレフィン又はアルコールの転化方法及びプロピレン又は芳香族化合物の製造方法
JP5426983B2 (ja) 2009-09-30 2014-02-26 旭化成ケミカルズ株式会社 Ｚｓｍ−５型ゼオライトの製造方法
WO2015029355A1 (ja) 2013-08-30 2015-03-05 東ソー株式会社 ペンタシル型ゼオライト及びその製造方法
CN110560155A (zh) 2019-09-17 2019-12-13 大连理工大学 一种由生物乙醇一步法直接生产丙烯的复合型催化剂的制备方法及应用
CN110871107A (zh) 2019-11-06 2020-03-10 厦门大学 一种用于低碳醇和石脑油耦合催化裂解制低碳烯烃的催化剂及其制备方法与应用

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2799004B2 (ja) * 1989-10-06 1998-09-17 三井化学株式会社 プロピレンの製造方法およびそれに用いる断熱型反応装置
EP1792885A1 (en) * 2005-11-29 2007-06-06 BP Chemicals Limited Process for producing ethylene
BRPI0605173A (pt) * 2006-12-05 2008-07-22 Braskem Sa processo de produção de uma ou mais olefinas, olefina, e, polìmero
CN101239870B (zh) * 2007-02-07 2011-08-17 中国石油化工股份有限公司 甲醇和乙醇转化制低碳烯烃的方法
CN103274884A (zh) * 2008-02-07 2013-09-04 道达尔石油化学产品研究弗吕公司 由乙醇制造烯烃的方法
CN101659592B (zh) * 2009-09-10 2014-02-12 惠生工程（中国）有限公司 一种粗甲醇直接制备丙烯的方法
JP5966776B2 (ja) * 2012-08-31 2016-08-10 三菱化学株式会社 プロピレン製造用触媒の製造方法
JP5978887B2 (ja) * 2012-09-25 2016-08-24 三菱化学株式会社 プロピレン及び直鎖ブテンの製造方法
WO2021006245A1 (ja) * 2019-07-05 2021-01-14 積水化学工業株式会社 エチレンの製造方法、及び重合体の製造方法

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5436203A (en) * 1977-08-09 1979-03-16 Petroleo Brasileiro Sa Process for preparing ethene
JP2007502796A (ja) * 2003-08-19 2007-02-15 トータル・ペトロケミカルズ・リサーチ・フエリユイ オレフィンの生産
WO2005056504A1 (ja) 2003-12-12 2005-06-23 Mitsubishi Chemical Corporation プロピレンの製造方法
JP2007291076A (ja) * 2006-03-30 2007-11-08 Mitsubishi Chemicals Corp プロピレンの製造方法
JP2007290991A (ja) * 2006-04-24 2007-11-08 Idemitsu Kosan Co Ltd 含酸素化合物からのオレフィン類の製造方法
US20110288358A1 (en) * 2008-12-11 2011-11-24 Lurgi Gmbh Method for producing a product containing c3h6 and c2h4
JP5426983B2 (ja) 2009-09-30 2014-02-26 旭化成ケミカルズ株式会社 Ｚｓｍ−５型ゼオライトの製造方法
US20140018593A1 (en) 2011-03-23 2014-01-16 Lurgi Gmbh Process and plant for the production of low-molecular olefins
US20130245290A1 (en) * 2011-09-07 2013-09-19 Shell Oil Company Process for preparing ethylene and propylene
WO2014025021A1 (ja) 2012-08-10 2014-02-13 旭化成ケミカルズ株式会社 オレフィン又はアルコールの転化方法及びプロピレン又は芳香族化合物の製造方法
WO2015029355A1 (ja) 2013-08-30 2015-03-05 東ソー株式会社 ペンタシル型ゼオライト及びその製造方法
CN110560155A (zh) 2019-09-17 2019-12-13 大连理工大学 一种由生物乙醇一步法直接生产丙烯的复合型催化剂的制备方法及应用
CN110871107A (zh) 2019-11-06 2020-03-10 厦门大学 一种用于低碳醇和石脑油耦合催化裂解制低碳烯烃的催化剂及其制备方法与应用

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"Adiabatic Fixed-Bed Reactors", 2014, ELSEVIER, pages: 5 - 24
"Stud. Surf. Sci. Catal.", vol. 33, 1987, pages: 167 - 215
"The Hydrothermal Synthesis of Zeolites", CHEMICAL REVIEWS, vol. 103, 2003, pages 663 - 702
See also references of EP4474371A4

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024070182A1 (ja) * 2022-09-30 2024-04-04 旭化成株式会社 エタノールの変換方法、炭化水素の製造方法、プロピレンの製造方法、芳香族化合物の製造方法、及び、エタノールの変換装置

Also Published As

Publication number Publication date
EP4474371A4 (en) 2026-02-18
JP7752192B2 (ja) 2025-10-09
JPWO2023145941A1 (https=) 2023-08-03
TW202340124A (zh) 2023-10-16
CA3248274A1 (en) 2025-01-17
JP2025157508A (ja) 2025-10-15
KR20240131407A (ko) 2024-08-30
EP4474371A1 (en) 2024-12-11
TWI900821B (zh) 2025-10-11

Similar Documents

Publication Publication Date Title
DK2238094T3 (en) DEHYDRATION OF ALCOHOLS ON CRYSTALLINIC SILICATES
KR101217915B1 (ko) 에탄올로부터의 올레핀의 제조 방법
US20110105815A1 (en) Process to Make Olefins from Ethanol
JPWO2000010948A1 (ja) エチレンおよびプロピレンの製造方法
KR20120094033A (ko) 프로필렌 생성을 향상시키기 위한 스팀 크래커 유닛의 디보틀네킹
WO1996010548A1 (en) Process for producing aromatic hydrocarbon
JP2025157508A (ja) エタノールの変換方法、及びその他炭化水素の製造方法
US20150119617A1 (en) Process for Converting Oxygenates to Olefins
TWI886774B (zh) 乙醇之轉換方法、含沸石之觸媒、含沸石之觸媒之製造方法、及烴等之製造方法
JP2023177331A (ja) アルコールの変換方法、及び炭化水素の製造方法
TWI860006B (zh) 乙醇之轉換方法、烴之製造方法、丙烯之製造方法、芳香族化合物之製造方法、及乙醇之轉換裝置
CN118647592A (zh) 乙醇的转化方法和其它烃的制造方法
JP2008056593A (ja) プロピレンの製造方法
TWI908470B (zh) 輕質烯烴之製造方法
JP7836744B2 (ja) エタノールの変換方法、炭化水素の製造方法、プロピレンの製造方法、芳香族化合物の製造方法、並びに、エタノールの変換装置
JP2024052594A (ja) エタノールの変換方法、炭化水素の製造方法、プロピレンの製造方法、芳香族化合物の製造方法、並びに、エタノールの変換装置
JP2024052593A (ja) エタノールの変換方法、炭化水素の製造方法、プロピレンの製造方法、芳香族化合物の製造方法、並びに、エタノールの変換装置
JP2025118099A (ja) エタノールの変換方法、ｃ２－３オレフィンの製造方法、及び触媒の再生方法
JP2025081054A (ja) 軽質オレフィンの製造方法
WO2016109372A1 (en) An oxygenate conversion process
WO2015000941A1 (en) A method of converting oxygenates to olefins
WO2015082368A1 (en) A process for converting oxygenates to olefins

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23747151

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2023577073

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 18728322

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2401004890

Country of ref document: TH

ENP Entry into the national phase

Ref document number: 20247025726

Country of ref document: KR

Kind code of ref document: A

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112024014729

Country of ref document: BR

WWE Wipo information: entry into national phase

Ref document number: 202380019397.6

Country of ref document: CN

WWE Wipo information: entry into national phase

Ref document number: 2023747151

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2023747151

Country of ref document: EP

Effective date: 20240902

ENP Entry into the national phase

Ref document number: 112024014729

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20240718