WO2010055953A1 - Procédé pour produire un composé benzène comprenant au moins cinq groupes méthyle - Google Patents

Procédé pour produire un composé benzène comprenant au moins cinq groupes méthyle Download PDF

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Publication number
WO2010055953A1
WO2010055953A1 PCT/JP2009/069517 JP2009069517W WO2010055953A1 WO 2010055953 A1 WO2010055953 A1 WO 2010055953A1 JP 2009069517 W JP2009069517 W JP 2009069517W WO 2010055953 A1 WO2010055953 A1 WO 2010055953A1
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WO
WIPO (PCT)
Prior art keywords
methyl groups
catalyst
benzene compound
reaction
methanol
Prior art date
Application number
PCT/JP2009/069517
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English (en)
Japanese (ja)
Inventor
秀高 嶋津
Original Assignee
広栄化学工業株式会社
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
Application filed by 広栄化学工業株式会社 filed Critical 広栄化学工業株式会社
Publication of WO2010055953A1 publication Critical patent/WO2010055953A1/fr

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Classifications

    • 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
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
    • 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
    • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
    • B01J29/7007—Zeolite Beta
    • 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
    • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
    • 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
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • a benzene compound having at least 5 methyl groups is used, for example, as a reaction solvent when a polyvalent carboxylic acid and a polyvalent amine are subjected to a polycondensation reaction in the presence of arylboric acid to produce polyamide, polyimide or polyamideimide. It is known that It has also been reported that it is used as a neutral ligand constituting an organometallic compound that is a resistance increase inhibitor and a polymerization initiator for a lithium secondary battery.
  • this invention provides the manufacturing method as described in the following [1].
  • the catalyst uses beta zeolite as a catalyst component.
  • a method for producing a benzene compound having at least 5 methyl groups comprising: Further, the present invention provides the production methods described in [2] to [6] below as preferred embodiments relating to the production method described in [1].
  • a benzene compound having 1 to 3 methyl groups is represented by the general formula (1): (Wherein m represents an integer of 1 to 3), and a benzene compound having at least 5 methyl groups is represented by the general formula (2):
  • a benzene compound having at least 5 methyl groups can be obtained in high yield.
  • a benzene compound having at least 5 methyl groups can be obtained from methylbenzene and dimethylbenzene, which are available at low cost, in a higher yield than conventional methods. Therefore, the method of the present invention is useful.
  • a benzene compound having 1 to 3 methyl groups and a mixture thereof are used as the raw material of the present invention.
  • the benzene compound having 1 to 3 methyl groups the general formula (1): (Wherein m represents an integer of 1 to 3). Specific examples include methylbenzene, 1,2-dimethylbenzene, 1,3-dimethylbenzene, 1, 4-Dimethylbenzene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene and mixtures thereof can be used.
  • methylbenzene, 1,2-dimethylbenzene, 1,4-dimethylbenzene and 1,2,4-trimethylbenzene are preferable.
  • methanol is used as a methylating agent.
  • the methanol used is 1 mole or more, preferably 2 to 30 moles, more preferably 4 to 15 moles per mole of the benzene compound having 1 to 3 methyl groups.
  • the catalyst used in the present invention is a catalyst containing beta zeolite as a catalyst component.
  • Beta zeolite is also known as zeolite beta, ⁇ -type zeolite and the like, and is a known synthetic crystalline aluminosilicate composed of three-dimensional oxygen 12-membered ring pores.
  • beta, zeolite, silica, diatomaceous earth, kaolin, bentonite, alumina and / or silica alumina and water as a slurry and spray-dry them to form spherical microbeads.
  • the beta zeolite shaped as described above is usually calcined. Firing is performed at 300 to 800 ° C. for several hours in air or nitrogen atmosphere. In the present invention, since the temperature of the catalyst is raised in the reaction tube, the calcination is not necessarily required.
  • the present invention is usually carried out by a gas phase reaction.
  • the solvent is not particularly limited as long as it is inert to the reaction, and any solvent can be used.
  • any solvent can be used.
  • aliphatic hydrocarbons such as hexane, heptane, octane, nonane, decane and undecane
  • halogenated aliphatic hydrocarbons such as dichloromethane and 1,2-dichloroethane
  • cyclic ethers such as tetrahydrofuran and dioxane, and the like are used. be able to. You may use these individually or in mixture of 2 or more types.
  • Example 2 The reaction was conducted in the same manner as in Example 1 except that the reaction temperature was 420 ° C. The results are shown in Table 1.
  • Example 3 The reaction was conducted in the same manner as in Example 1 except that the reaction temperature was changed to 450 ° C. The results are shown in Table 1.
  • Example 4 The reaction was performed in the same manner as in Example 2 except that 1,4-dimethylbenzene (hereinafter abbreviated as 14-DMB) was used instead of 124-TMB.
  • 14-DMB 1,4-dimethylbenzene
  • the reaction product was absorbed in methylbenzene and then analyzed by gas chromatography.
  • Table 1 shows the average yield (calculated based on 12-DMB) for 2 hours from the start of the reaction.
  • Example 7 The reaction was performed in the same manner as in Example 6 except that methylbenzene (hereinafter abbreviated as MB) was used instead of 12-DMB. The results are shown in Table 1 (average yield is calculated based on MB).
  • Example 8 Preparation of catalyst B
  • 150 g of colloidal silica Colloidal silica (Nissan Chemical Industries, Snowtex) were mixed.
  • the obtained mixture was extruded and calcined at 500 ° C. to prepare catalyst B having a diameter of 1.5 mm.
  • reaction using catalyst B The reaction was performed in the same manner as in Example 1 except that the catalyst B was used instead of the catalyst A. The results are shown in Table 1.
  • Example 9 Preparation of catalyst E
  • the obtained solid was pulverized and classified to 10 to 16 mesh to prepare catalyst E.
  • Reaction using catalyst E A glass reaction tube with an inner diameter of 19 mm was packed with 16 ml of catalyst E, and carborundum was packed thereon to a length of 14 cm.
  • the reaction product was absorbed in methylbenzene and then analyzed by gas chromatography. Table 1 shows the average yield (calculated on the basis of 14-DMB) for 6 hours from the start of the reaction.
  • the reaction product was absorbed in methylbenzene and then analyzed by gas chromatography. Table 2 shows the average yield for 2 hours from the start of the reaction.
  • Comparative Example 2 Preparation of catalyst D 850 g of USY-type zeolite powder (manufactured by NE Chemcat Co., Ltd.) and 150 g of colloidal silica (manufactured by Nissan Chemical Industries, Ltd., Snowtex) were mixed. The obtained mixture was extruded and then calcined at 500 ° C. to prepare catalyst D having a diameter of 1.5 mm. (Reaction using catalyst D) The reaction was performed in the same manner as in Comparative Example 1 except that the catalyst D was used instead of the catalyst C. The results are shown in Table 2. Comparative Example 3 The reaction was performed in the same manner as in Comparative Example 2 except that 14-DMB was used instead of 124-TMB. The results are shown in Table 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé pour produire un composé benzène comprenant au moins cinq groupes méthyle, dans lequel un composé comprenant un à trois groupes méthyle est amené à réagir avec du méthanol en présence d'un catalyseur à base de bêta-zéolithe en tant que composant catalytique. 　
PCT/JP2009/069517 2008-11-13 2009-11-11 Procédé pour produire un composé benzène comprenant au moins cinq groupes méthyle WO2010055953A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008291187 2008-11-13
JP2008-291187 2008-11-13

Publications (1)

Publication Number Publication Date
WO2010055953A1 true WO2010055953A1 (fr) 2010-05-20

Family

ID=42170080

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2009/069517 WO2010055953A1 (fr) 2008-11-13 2009-11-11 Procédé pour produire un composé benzène comprenant au moins cinq groupes méthyle

Country Status (2)

Country Link
JP (1) JP5512237B2 (fr)
WO (1) WO2010055953A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5583717A (en) * 1978-12-14 1980-06-24 Mobil Oil Alkylation of aromatic hydrocarbon compound
JPH03287549A (ja) * 1990-04-02 1991-12-18 Mitsui Petrochem Ind Ltd ヘキサメチルベンゼンの製造方法
JPH05294852A (ja) * 1992-04-17 1993-11-09 Japan Energy Corp ヘキサメチルベンゼンの製造方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5583717A (en) * 1978-12-14 1980-06-24 Mobil Oil Alkylation of aromatic hydrocarbon compound
JPH03287549A (ja) * 1990-04-02 1991-12-18 Mitsui Petrochem Ind Ltd ヘキサメチルベンゼンの製造方法
JPH05294852A (ja) * 1992-04-17 1993-11-09 Japan Energy Corp ヘキサメチルベンゼンの製造方法

Also Published As

Publication number Publication date
JP5512237B2 (ja) 2014-06-04
JP2010138167A (ja) 2010-06-24

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