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WO2009110402A1 - Procédé de production du paraxylène - Google Patents

Procédé de production du paraxylène Download PDF

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Publication number
WO2009110402A1
WO2009110402A1 PCT/JP2009/053813 JP2009053813W WO2009110402A1 WO 2009110402 A1 WO2009110402 A1 WO 2009110402A1 JP 2009053813 W JP2009053813 W JP 2009053813W WO 2009110402 A1 WO2009110402 A1 WO 2009110402A1
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WO
WIPO (PCT)
Prior art keywords
reaction
ethylene
raw materials
petroleum
dimethylfuran
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/JP2009/053813
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English (en)
Japanese (ja)
Inventor
慶次郎 高西
三郎 曽根
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.)
Toray Industries Inc
Original Assignee
Toray Industries Inc
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 Toray Industries Inc filed Critical Toray Industries Inc
Priority to JP2009510628A priority Critical patent/JPWO2009110402A1/ja
Publication of WO2009110402A1 publication Critical patent/WO2009110402A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • 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
    • C07C1/247—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by splitting of cyclic ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • 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

  • the present invention relates to a method for producing para-xylene.
  • non-petroleum resin materials such as polylactic acid have been actively developed and adopted in the material field as well as non-petroleum energy such as photovoltaic power generation.
  • condensation resins such as polyethylene terephthalate (PET) and polybutylene terephthalate (PBT) are used in a wide range of fields including parts such as packaging materials, optical materials, electrical and electronic equipment, and automobiles.
  • PET polyethylene terephthalate
  • PBT polybutylene terephthalate
  • These are condensation polymers made from petroleum-derived compounds, such as dicarboxylic acid compounds such as terephthalic acid and diol compounds.
  • 1,3-propanediol which is a non-petroleum diol, has been developed, and it has been used as a resin raw material for this series. For this reason, there has been an active movement to use biomass raw materials in consideration of environmental impacts. .
  • the dicarboxylic acid compound that is the other raw material particularly terephthalic acid that is often used
  • the synthesis starting material is paraxylene, which is a petroleum-derived raw material
  • Single-step synthesis of para-xylene from bio raw materials has been eagerly desired.
  • non-petroleum compounds that is, bio-based compounds into various synthetic synthons
  • biochemical techniques such as enzymatic methods and artificial synthetic techniques.
  • furan compounds that can be synthesized from sugar chain compounds such as glucose and fructose have recently attracted attention.
  • An object of the present invention is to provide a method for producing paraxylene using 2,5-dimethylfuran and ethylene as raw materials.
  • terephthalic acid can be synthesized from non-petroleum-derived raw materials. That means that a raw material of a general-purpose resin having a terephthalic acid structure such as PET can be converted from a petroleum material to a non-petroleum biomass material.
  • a raw material of a general-purpose resin having a terephthalic acid structure such as PET can be converted from a petroleum material to a non-petroleum biomass material.
  • Such technology has a tremendous effect on reducing environmental impact, and it can be said that it is an important technology that can greatly contribute to the construction of a sustainable social structure.
  • the present inventors as a method for synthesizing para-xylene using 2,5-dimethylfuran as a raw material, used Diels-Alder reaction as shown in the following formula 1 for 2,5-dimethylfuran and ethylene. Then, a method of dehydrating the obtained bicyclo compound as represented by the following formula 2 was devised.
  • Diels-Alder reaction can easily proceed in the presence of no catalyst or various catalysts (metal salts such as titanium, zirconium, hafnium, aluminum, zinc, etc.) Is widely known.
  • metal salts such as titanium, zirconium, hafnium, aluminum, zinc, etc.
  • the Diels-Alder reaction of ethylene without a substituent has a problem that it has a high activation energy and is difficult to proceed.
  • the present invention makes it possible to produce para-xylene using dimethylfuran and ethylene synthesized from glucose, which is a non-petroleum raw material, as raw materials.
  • glucose which is a non-petroleum raw material
  • the raw material of petroleum-based general-purpose resin having a terephthalic acid structure could be converted into non-petroleum biomass material, and the technology that greatly contributed to the construction of a sustainable social structure could be established by its environmental impact reduction effect.
  • the para-xylene production method of the present invention uses 2,5-dimethylfuran (hereinafter abbreviated as DMF) and ethylene as raw materials, and performs Diels-Alder reaction (hereinafter abbreviated as DA reaction) (the following formula 1).
  • DMF 2,5-dimethylfuran
  • DA reaction Diels-Alder reaction
  • para-xylene is produced by subjecting the bicyclo compound (1) to a dehydration reaction (the following formula 2).
  • the feed ratio of ethylene and DMF (ethylene / DMF) as raw materials is preferably 1 or greater than 1.
  • a charge ratio (ethylene / DMF) of greater than 1 means an excess of ethylene.
  • a more preferable charging ratio is 1 or more and 50 or less, more preferably 1 or more and 10 or less.
  • the progress of the reaction is greatly influenced by pressure because the boiling point of ethylene, which is one of the raw materials, is extremely low. For this reason, the DA reaction is preferably carried out by enclosing the raw materials in a sealed container or while continuously injecting the respective raw materials into the reaction tube.
  • the reaction temperature is preferably 40 to 250 ° C, more preferably 80 to 200 ° C, and further preferably 120 to 180 ° C.
  • the reaction pressure depends on the amount of raw material charged and the reaction vessel volume when using a sealed container, and on the cross-sectional area and the liquid feed pressure of the raw material when using a reaction tube. In either case, the reaction pressure appropriately changes depending on the temperature and the volume of the container, but is preferably 1 atm or more and 100 atm or less.
  • the dehydration reaction of Formula 2 for converting the bicyclo compound (1) to paraxylene proceeds by allowing the bicyclo compound (1) to act on an organic condensing agent such as an inorganic salt, inorganic oxide, or carbodiimide having a dehydrating action. Can be made.
  • an organic condensing agent such as an inorganic salt, inorganic oxide, or carbodiimide having a dehydrating action.
  • the bicyclo compound (1) can be isolated and purified by allowing an inorganic salt such as sodium sulfate or magnesium sulfate or a composite oxide such as silica / alumina to be present as a dehydration catalyst.
  • the DA reaction and the dehydration reaction can be performed continuously, and the efficiency of the reaction can be improved.
  • the dehydration catalyst used in this case is more preferably a composite oxide containing silica / alumina.
  • the amount of the dehydration catalyst is preferably 0.1 mol% or more and 20 mol% or less with respect to DMF as a raw material.
  • a catalyst can also be used for the DA reaction.
  • DA catalyst metal salts such as titanium, zirconium, hafnium, aluminum, zinc, and antimony, complex compounds, and the like are preferably used. It is also preferable that the DA catalyst and the dehydration catalyst coexist.
  • the amount of DA catalyst is preferably 0.1 mol% or more and 10 mol% or less with respect to DMF as a raw material.
  • Example 5 mL (0.48 g) of DMF (molecular weight 96), 0.05 mmol (12.5 mg) of titanocene dichloride, silica-alumina composite oxide particles (particle size: 0.1 to 5 ⁇ m) 81 mg: 0.6 mmol) of the silica-alumina composite oxide with a molecular weight of 135, which was replaced with nitrogen, and then sealed with a rubber stopper with a glass cock. Subsequently, a balloon filled with ethylene gas was connected to the glass cock part, and the glass ampoule part was cooled with liquid nitrogen. After confirming that the gaseous ethylene had finished condensing in the ampule container, the cock was closed and the ampule was sealed.
  • this ampoule was put into an oil bath heated to 180 ° C. for 3 hours for reaction. Thereafter, the ampule was taken out and the container was again cooled with liquid nitrogen, and then the ampule was opened. The opened ampoule was gradually heated to room temperature and the excess ethylene gas was removed by natural evaporation. The weight of the organic matter remaining in the ampoule was 0.51 g. It was confirmed that the main component of the organic substance was para-xylene ( 1 H-NMR). As a result of quantification using an internal standard, the yield of paraxylene was 0.49 g.
  • the present invention makes it possible to produce para-xylene using dimethylfuran and ethylene synthesized from glucose, which is a non-petroleum raw material, as raw materials.
  • glucose which is a non-petroleum raw material
  • the raw material of petroleum-based general-purpose resin having a terephthalic acid structure could be converted into non-petroleum biomass material, and the technology that greatly contributed to the construction of a sustainable social structure could be established by its environmental impact reduction effect.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Cette invention concerne un procédé de production du paraxylène, qui utilise le 2,5-diméthylfuranne et l'éthylène comme matières premières, et comprend une réaction de Diels-Alder et une réaction de déshydratation. Dans ce procédé, le diméthylfuranne synthétisé à partir de glucose qui n'est pas une substance synthétique et l'éthylène sont utilisés comme matières premières pour produire le paraxylène.
PCT/JP2009/053813 2008-03-03 2009-03-02 Procédé de production du paraxylène Ceased WO2009110402A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009510628A JPWO2009110402A1 (ja) 2008-03-03 2009-03-02 パラキシレンの製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008051656 2008-03-03
JP2008-051656 2008-03-03

Publications (1)

Publication Number Publication Date
WO2009110402A1 true WO2009110402A1 (fr) 2009-09-11

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2009/053813 Ceased WO2009110402A1 (fr) 2008-03-03 2009-03-02 Procédé de production du paraxylène

Country Status (2)

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JP (1) JPWO2009110402A1 (fr)
WO (1) WO2009110402A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010151346A1 (fr) * 2009-06-26 2010-12-29 Uop Llc Voie glucide pour l'obtention de paraxylène et d'acide téréphtalique
WO2013040514A1 (fr) * 2011-09-16 2013-03-21 Micromidas Inc. Procédés de fabrication de para-xylène et d'acide téréphtalique
WO2013185149A1 (fr) * 2012-06-05 2013-12-12 University Of Massachusetts Procédé de conversion d'une matière hydrocarbonée en un produit hydrocarboné fluide comprenant du p-xylène
WO2014043468A1 (fr) * 2012-09-14 2014-03-20 Micromidas Inc. Procédés d'obtention de para-xylène et d'acide téréphtalique
US8889938B2 (en) 2012-03-15 2014-11-18 Micromidas, Inc. Methods of producing para-xylene
WO2015042407A1 (fr) 2013-09-20 2015-03-26 Micromidas, Inc. Procédés de production de 5-(halogénométhyl)furfural
JP2015520131A (ja) * 2012-04-20 2015-07-16 ザ コカ・コーラ カンパニーＴｈｅ Ｃｏｃａ‐Ｃｏｌａ Ｃｏｍｐａｎｙ バイオマスからパラ−キシレンを調製する方法
US9115155B1 (en) 2014-03-20 2015-08-25 Eastman Chemical Company Low-pressure synthesis of cyclohexanedimethanol and derivatives
US9321714B1 (en) 2014-12-05 2016-04-26 Uop Llc Processes and catalysts for conversion of 2,5-dimethylfuran derivatives to terephthalate
WO2016114668A1 (fr) 2015-01-16 2016-07-21 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Procédé de préparation de composés phénoliques à partir de biomasse
CN106256807A (zh) * 2015-06-19 2016-12-28 中国石油化工股份有限公司 四氢呋喃类化合物芳构化生产芳烃的方法
JP2017137293A (ja) * 2015-10-12 2017-08-10 中国石油化工股▲ふん▼有限公司 芳香族炭化水素、ｐ−キシレン及びテレフタル酸を製造する方法
US10392317B2 (en) 2012-09-14 2019-08-27 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid
US10604498B2 (en) 2013-03-14 2020-03-31 Micromidas, Inc. Methods for purifying 5-(halomethyl)furfural
CN115368375A (zh) * 2021-05-19 2022-11-22 中国石油化工股份有限公司 一种制备氧杂-降冰片烯的方法
WO2023127644A1 (fr) * 2021-12-27 2023-07-06 東レ株式会社 Procédé de fabrication d'hydrocarbure aromatique, procédé de fabrication de polymère et appareil de fabrication d'hydrocarbure aromatique
WO2025225714A1 (fr) * 2024-04-26 2025-10-30 東レ株式会社 Procédé de production de 2,5-diméthylfurane, procédé de production de para-xylène, procédé de production d'acide téréphtalique, procédé de production de polyester, para-xylène, acide téréphtalique, composition de polyester, matériau fibreux, matériau de résine, matériau de film, produit fibreux, produit de résine et produit de film

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CHAMBERS, R.D. ET AL.: "Polyhalogenated heterocyclic compounds. Part 41. Cycloaddition reactions involving hexafluorobut-2-yne and 1, 1, 1, 2, 4, 4, 4-heptafluorobut-2-ene", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, 1996, pages 1095 - 1100 *
FRAILE, J.M. ET AL.: "Tandem diels-alder aromatization reactions of furans under unconventional reaction conditions - experimental and theoretical studies", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, pages 2891 - 2899 *
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Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102482177B (zh) * 2009-06-26 2014-10-29 环球油品公司 对二甲苯和对苯二甲酸的碳水化合物途径
CN102482177A (zh) * 2009-06-26 2012-05-30 环球油品公司 对二甲苯和对苯二甲酸的碳水化合物途径
AU2010263188B2 (en) * 2009-06-26 2012-12-20 Uop Llc Carbohydrate route to para-xylene and terephthalic acid
WO2010151346A1 (fr) * 2009-06-26 2010-12-29 Uop Llc Voie glucide pour l'obtention de paraxylène et d'acide téréphtalique
US9260359B2 (en) 2011-09-16 2016-02-16 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid
CN103814005B (zh) * 2011-09-16 2017-12-29 微麦德斯公司 对二甲苯和对苯二甲酸的制造方法
CN103814005A (zh) * 2011-09-16 2014-05-21 微麦德斯公司 对二甲苯和对苯二甲酸的制造方法
JP2014528939A (ja) * 2011-09-16 2014-10-30 マイクロマイダス インコーポレイテッド パラ−キシレンおよびテレフタル酸の生産方法
WO2013040514A1 (fr) * 2011-09-16 2013-03-21 Micromidas Inc. Procédés de fabrication de para-xylène et d'acide téréphtalique
US9890101B2 (en) 2011-09-16 2018-02-13 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid
US8889938B2 (en) 2012-03-15 2014-11-18 Micromidas, Inc. Methods of producing para-xylene
US10125060B2 (en) 2012-03-15 2018-11-13 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid
JP2015520131A (ja) * 2012-04-20 2015-07-16 ザ コカ・コーラ カンパニーＴｈｅ Ｃｏｃａ‐Ｃｏｌａ Ｃｏｍｐａｎｙ バイオマスからパラ−キシレンを調製する方法
WO2013185149A1 (fr) * 2012-06-05 2013-12-12 University Of Massachusetts Procédé de conversion d'une matière hydrocarbonée en un produit hydrocarboné fluide comprenant du p-xylène
WO2014043468A1 (fr) * 2012-09-14 2014-03-20 Micromidas Inc. Procédés d'obtention de para-xylène et d'acide téréphtalique
US10392317B2 (en) 2012-09-14 2019-08-27 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid
JP2015531786A (ja) * 2012-09-14 2015-11-05 マイクロマイダス，インコーポレイテッド パラ−キシレンおよびテレフタル酸の生成方法
US10604498B2 (en) 2013-03-14 2020-03-31 Micromidas, Inc. Methods for purifying 5-(halomethyl)furfural
EP4166546A1 (fr) 2013-09-20 2023-04-19 Origin Materials Operating, Inc. Procédés de production de 5-(halométhyl)furfural
WO2015042407A1 (fr) 2013-09-20 2015-03-26 Micromidas, Inc. Procédés de production de 5-(halogénométhyl)furfural
US10710970B2 (en) 2013-09-20 2020-07-14 Micromidas, Inc. Methods for producing 5-(halomethyl)furfural
US11299468B2 (en) 2013-09-20 2022-04-12 Origin Materials Operating, Inc. Methods for producing 5-(halomethyl)furfural
US12281089B2 (en) 2013-09-20 2025-04-22 Origin Materials Operating, Inc. Methods for producing 5-(halomethyl)furfural
US9115155B1 (en) 2014-03-20 2015-08-25 Eastman Chemical Company Low-pressure synthesis of cyclohexanedimethanol and derivatives
US9321714B1 (en) 2014-12-05 2016-04-26 Uop Llc Processes and catalysts for conversion of 2,5-dimethylfuran derivatives to terephthalate
WO2016114668A1 (fr) 2015-01-16 2016-07-21 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Procédé de préparation de composés phénoliques à partir de biomasse
CN106256807A (zh) * 2015-06-19 2016-12-28 中国石油化工股份有限公司 四氢呋喃类化合物芳构化生产芳烃的方法
JP2017137293A (ja) * 2015-10-12 2017-08-10 中国石油化工股▲ふん▼有限公司 芳香族炭化水素、ｐ−キシレン及びテレフタル酸を製造する方法
CN115368375A (zh) * 2021-05-19 2022-11-22 中国石油化工股份有限公司 一种制备氧杂-降冰片烯的方法
WO2023127644A1 (fr) * 2021-12-27 2023-07-06 東レ株式会社 Procédé de fabrication d'hydrocarbure aromatique, procédé de fabrication de polymère et appareil de fabrication d'hydrocarbure aromatique
WO2025225714A1 (fr) * 2024-04-26 2025-10-30 東レ株式会社 Procédé de production de 2,5-diméthylfurane, procédé de production de para-xylène, procédé de production d'acide téréphtalique, procédé de production de polyester, para-xylène, acide téréphtalique, composition de polyester, matériau fibreux, matériau de résine, matériau de film, produit fibreux, produit de résine et produit de film

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