WO2007114195A1 - Procede de fabrication de propylene - Google Patents

Procede de fabrication de propylene Download PDF

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Publication number
WO2007114195A1
WO2007114195A1 PCT/JP2007/056732 JP2007056732W WO2007114195A1 WO 2007114195 A1 WO2007114195 A1 WO 2007114195A1 JP 2007056732 W JP2007056732 W JP 2007056732W WO 2007114195 A1 WO2007114195 A1 WO 2007114195A1
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WO
WIPO (PCT)
Prior art keywords
propylene
ethylene
reaction
ethanol
catalyst
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PCT/JP2007/056732
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English (en)
Japanese (ja)
Inventor
Masashi Yamaguchi
Yumiko Yoshikawa
Takahiko Takewaki
Tohru Setoyama
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Mitsubishi Chemical Corporation
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Filing date
Publication date
Application filed by Mitsubishi Chemical Corporation filed Critical Mitsubishi Chemical Corporation
Priority to KR1020087023582A priority Critical patent/KR101382804B1/ko
Priority to CN2007800113440A priority patent/CN101410353B/zh
Publication of WO2007114195A1 publication Critical patent/WO2007114195A1/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
    • 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
    • B01J29/7015—CHA-type, e.g. Chabazite, LZ-218
    • 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
    • C07C1/24—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 elimination of water
    • 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
    • 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
    • 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
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • 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

  • the present invention relates to a method for producing propylene by contacting at least one of ethanol and ethylene in a reactor in the presence of a catalyst.
  • the present invention also relates to a method for producing polypropylene using the produced propylene.
  • polymers using plant-derived raw materials have recently attracted attention as polymers with a low environmental impact, and some polymers are also emerging in the field.
  • Polypropylene a general-purpose resin, mainly uses crude oil. Propylene power is produced as a raw material. If propylene can be produced using plant-derived raw materials (bioethanol), it is expected that the effect of reducing environmental impact will be very large.
  • Patent Document 1 US Pat. No. 4,148,835
  • Patent Document 1 states that an alcohol having 1 to 4 carbon atoms is used as a raw material, and the raw material is not limited to methanol, but is specifically disclosed in the examples. Alcohol is only methanol, and no examples using ethanol as a raw material are described.
  • ZSM-5 which is an aluminosilicate generally known as a catalyst for MT0
  • SAPO-34 a catalyst for MT0
  • ethanol was used as a raw material.
  • the raw ethanol was immediately dehydrated. It has been found that it produces pure ethylene. And once ethylene was produced, the subsequent reaction was very slow. It was found that the yield of propylene was very low.
  • methanol is used as a raw material, olefins such as ethylene are produced from methanol, and the produced ethylene and raw material methanol react to produce propylene efficiently. Tested with 1.
  • propylene as described above can be produced using plant-derived raw materials (bioethanol), it is expected that the effect of reducing environmental impact will be very large.
  • plant-derived raw materials bioethanol
  • ethanol is used as a raw material.
  • the method for producing propylene has not been sufficiently studied, and it has been desired to establish a method for producing propylene in high yield using ethanol as a raw material.
  • An object of the present invention is to provide a method for obtaining propylene in high yield with at least one of ethanol and ethylene.
  • the present invention also provides a method for producing polypropylene from propylene produced by this method.
  • the first gist of the present invention is a method for producing propylene by bringing at least one of ethanol and ethylene into contact with a catalyst in a reactor, wherein the catalyst comprises:
  • the present invention relates to a method for producing propylene characterized by containing an aluminosilicate having a pore diameter of less than 5 nm as a catalytically active component.
  • the second gist of the present invention resides in a method for producing propylene, characterized in that, in the above method, the catalytically active component is an aluminosilicate having an 8-membered ring or a 9-membered ring.
  • the third gist of the present invention resides in a method for producing propylene, characterized in that the structure of the aluminosilicate is CHA in the above method.
  • a fourth aspect of the present invention is that in the above method, the aluminosilicate SiO / AlO module is used.
  • the present invention relates to a method for producing propylene, wherein the ratio of 2 2 3 is 5 or more.
  • a fifth aspect of the present invention is a propylene production method characterized in that in the above method, propylene is produced while continuously regenerating the catalyst in an equipment equipped with a fluidized bed reactor and a regenerator. Manufacturing method.
  • the sixth gist of the present invention is that, in the above method, at least one conversion rate of ethanol and ethylene (conversion rate from at least one of ethanol and ethylene to a compound other than ethanol and ethylene).
  • the present invention resides in a method for producing propylene, characterized in that the reaction is carried out under such a condition that it is 20% or more and 80% or less.
  • a seventh aspect of the present invention resides in a method for producing propylene, characterized in that, in the above method, at least a part of ethylene contained in the reactor outlet gas is recycled to the reactor.
  • An eighth aspect of the present invention resides in a method for producing polypropylene, characterized in that polypropylene is produced using propylene produced by the above-described method for producing propylene as a raw material.
  • propylene can be produced in high yield with at least one of ethanol and ethylene.
  • polypropylene which is a general-purpose resin
  • bioethanol which is a plant-derived raw material
  • the catalyst used in the present invention is an aluminosilicate having a pore diameter of less than 0.5 nm as a catalyst active component.
  • the pore size mentioned here refers to the crystallographic free diameter of the channels stipulated by the International Zeolite Association (IZA) and is described in ATLAS OF ZEOLITE FRAMEWORKTYPES FIFTH RIVISED EDITION 2 Yes. Therefore, the pore diameter of less than 0.5 nm means that If the shape of the flannel is a perfect circle, it means that the diameter is less than 0.5 nm. If the shape of the pore is an ellipse, it means that the minor axis is less than 0.5 nm.
  • the pore size of the aluminosilicate is 0.5 nm or more, there is a disadvantage that by-products other than propylene (butene, pentene, etc.) increase, and at least one of ethanol and ethylene is high. It is not possible to produce propylene in a yield. Although the details of the mechanism of action that propylene can be produced in high yield from at least one of ethanol and ethylene by using an aluminosilicate with a pore size of less than 0.5 nm are not clear, It is considered that ethanol and ethylene can be activated by the expression of propylene and that propylene can be selectively produced with a small pore size.
  • propylene the target product
  • the pores can emerge from the pores. Butene and pentene, which are by-products, are too large in size. It is estimated that it remains in the pores. This mechanism is thought to improve the selectivity of propylene.
  • the lower limit of the pore diameter of the aluminosilicate is not particularly limited.
  • aluminosilicate composed of only eight-membered rings, for example, AFX, CAS, CHA, DDR, ERI, ESV, GIS, GOO, ITE, JBW, KFI, LEV, LTA, MER, MON, MTF, PAU, PHI, RH0, RTE, RTH, etc.
  • Aluminosilicates having these structures can be synthesized based on known information.
  • US4544538A describes a method for synthesizing an aluminosilicate having a CHA structure (the crystallographic channel diameter defined by IZA is 0.38 nm). It is disclosed.
  • an aluminosilicate having a framework density of 18. OTZnm 3 or less is more preferable, and AFX, CHA, DDR, ERI, LEV, RHO can be exemplified. Most preferred is CHA.
  • the framework density (unit: TZnm 3 ) is the T atom (atom other than oxygen among the atoms constituting the zeolite skeleton) present per unit volume (lnm 3 ) of zeolite.
  • Pieces It means a number, and this value is determined by the structure of the zeolite.
  • the SiO / A10 molar ratio of aluminosilicate as the catalytically active component is 5 or more.
  • the upper limit of the molar ratio of SiO / AlO is usually 1000
  • the molar ratio can be determined by conventional methods such as X-ray fluorescence and chemical analysis.
  • the catalytically active component may be used as it is in the reaction as a catalyst, or may be granulated and molded using a substance or binder that is inert to the reaction, or may be used in the reaction by mixing them. good.
  • the substance and binder inert to the reaction include alumina or alumina zone, silica, silica gel, quartz, and mixtures thereof.
  • the composition of the catalytically active component described above is a composition of only the catalytically active component that does not contain a substance inactive to these reactions or a binder.
  • the catalyst according to the present invention contains a substance or binder that is inert to these reactions, the catalyst active component and the substance or binder that are inert to these reactions are combined with the catalyst.
  • the catalyst is composed of only the catalytically active component.
  • the particle size of the catalyst varies depending on the conditions during the synthesis. Usually, the average particle size is 0.01 ⁇ m to 50 0 / m. If the particle size of the catalyst is too large, the surface area showing the catalytic activity will be small, and if it is too small, the handleability will be inferior, which is not preferable in either case. This average particle diameter can be determined by SEM observation or the like.
  • the method for preparing the catalyst used in the present invention is not particularly limited, and can be prepared by a known method generally called hydrothermal synthesis.
  • the composition can be changed after hydrothermal synthesis by modification such as ion exchange, dealumination treatment, impregnation and loading.
  • the catalyst used in the present invention may be prepared by any method as long as it has the above-mentioned physical properties and further composition when subjected to the reaction.
  • reaction raw materials Next, ethanol, ethylene and the like used as reaction raw materials in the present invention will be described.
  • Ethanol used as a raw material for the reaction is not particularly limited.
  • those obtained by various known methods such as those produced by hydration of ethylene, those produced from synthesis gas, and those produced by fermentation using plant-derived polysaccharides as raw materials are arbitrarily selected.
  • a compound in which a compound (particularly water) resulting from each production method is arbitrarily mixed may be used as it is, or purified ethanol may be used.
  • the ethylene used for the reaction raw material can be obtained by synthesizing FT (Fischer-Tropsch) using raw materials such as oil feedstock, those produced by catalytic cracking or steam cracking, and hydrogen ZCO mixed gas obtained by coal gasification. , Obtained by ethane dehydrogenation or oxidative dehydrogenation, obtained by propylene metathesis reaction and homozygous reaction, obtained by MTO reaction, obtained by ethanol dehydration reaction, etc. A known product obtained by various methods can be arbitrarily used. At this time, a compound in which a compound other than ethylene caused by each production method is arbitrarily mixed may be used as it is, or purified ethylene is used. May be.
  • ethylene contained in the reactor outlet gas may be recycled and used.
  • the reaction raw material may contain olefins having 4 or more carbon atoms in addition to the ethanol and ethylene.
  • the olefin having 4 or more carbon atoms is not particularly limited.
  • the olefins contained in the reactor outlet gas may be recycled and used. Since a part of olefin having 4 or more carbon atoms is converted to propylene, the consistent yield of propylene can be improved by recycling the olefin in the reactor outlet gas in this way.
  • oxygen-containing compounds other than ethanol are present, it is acceptable.
  • Oxygen content other than ethanol examples include methanol and dimethyl ether.
  • the form of the reactor to be used is not particularly limited, but a continuous fixed bed reactor or a fluidized bed reactor is usually selected. A fluidized bed reactor is preferred.
  • granular materials inert to the reaction such as quartz sand, alumina, silica, silica-alumina, etc. are combined with the catalyst. You may mix and fill. In this case, there is no particular limitation on the amount of granular material inert to the reaction such as quartz sand. In addition, it is preferable that this granular material is a particle size comparable as a catalyst from the surface of uniform mixing property with a catalyst.
  • reaction substrate (reaction raw material) may be divided and supplied to the reactor for the purpose of dispersing heat generated by the reaction.
  • a catalyst regenerator is attached to the reactor, the catalyst extracted from the reactor is continuously sent to the regenerator, and the catalyst regenerated in the regenerator is continuously supplied. It is preferable to carry out the reaction while returning to the reactor.
  • examples of the catalyst regenerator include those that regenerate the catalyst introduced from the reactor by treating it with nitrogen gas containing oxygen or water vapor.
  • the concentration of at least one of ethanol and ethylene in all feed components fed to the reactor ie, substrate concentration
  • the sum of ethanol and ethylene is preferably 90 mol% or less in all feed components. . More preferably, it is 5 mol% or more and 70 mol% or less. If the substrate concentration is too high, aromatic compounds and paraffins are prominently produced, and the yield of propylene tends to decrease. If the substrate concentration is too low, the reaction rate becomes slow, so a large amount of catalyst is required and the reactor tends to be too large. Therefore, use the diluents described below as necessary to achieve such substrate concentrations. It is preferred to dilute at least one of ethanol and ethylene.
  • impurities contained in the reaction raw material may be used as they are, or a separately prepared diluent may be mixed with the reaction raw material and used.
  • the diluent may be mixed with the reaction raw material before entering the reactor, or may be supplied to the reactor separately from the reaction raw material.
  • the space velocity mentioned here is the flow rate of at least one of ethanol and ethylene, which are reaction raw materials per weight of the catalyst (catalytic active component), where the weight of the catalyst is used for granulating and molding the catalyst. It is the weight of the catalytically active component that does not contain the inactive component and binder.
  • the flow rate is the total flow rate (weight / hour) of at least one of ethanol and ethylene (ie, the total when ethanol and ethylene are used).
  • the space velocity is between the preferred instrument 0. LHR _ 1 between 500Ita 1 from 0. 01Hr _ 1 of 100 Hr _1 is more preferable. If the space velocity is too high, ethylene in the reactor outlet gas increases and propylene yield decreases, which is preferable. Also, if the space velocity is too low, undesirable by-products such as norafines are produced and the propylene yield is reduced, which is preferable.
  • the lower limit of the reaction temperature is usually about 200 ° C or higher, preferably 300 ° C or higher, and the upper limit of the reaction temperature is usually 700 ° C or lower, preferably 600 ° C or lower. If the reaction temperature is too low, a large amount of unreacted raw material with a low reaction rate tends to remain, and the yield of propylene also decreases. On the other hand, if the reaction temperature is too high, the yield of propylene is significantly reduced.
  • reaction pressure The upper limit of the reaction pressure is usually 2 MPa (absolute pressure, the same applies hereinafter) or less, preferably IMPa or less, and more preferably 0.7 MPa or less.
  • the lower limit of the reaction pressure is not particularly limited, but is usually 1 kPa or more, preferably 50 kPa or more. If the reaction pressure is too high, the amount of undesired by-products such as paraffins increases, and the yield of propylene tends to decrease. If the reaction pressure is too low, the reaction rate tends to be slow.
  • the conversion rate of at least one of ethanol and ethylene is 20% or more and 80% or less. It is preferable to carry out the reaction under conditions. If the conversion is less than 20%, unreacted ethanol or ethylene is large, and the propylene yield is low, which is not preferable. On the other hand, if it exceeds 80%, undesirable by-products such as paraffins increase and the propylene yield decreases, which is preferable.
  • the conversion rate is more preferably 20% or more and 70% or less.
  • the catalyst can be operated at a preferred conversion rate by adjusting the residence time of the catalyst in the reactor and the residence time in the regenerator.
  • reactor effluent a mixed gas containing the reaction products propylene, ethylene, by-products and a diluent is obtained.
  • the propylene concentration in the mixed gas is usually 1 to 95% by weight, preferably 2 to 80% by weight.
  • this mixed gas may contain ethanol. It is preferable to carry out the reaction under such reaction conditions that the reactor outlet gas does not contain any ethanol. This facilitates separation of the reaction product and the unreacted raw material.
  • This mixed gas usually contains ethylene. It is preferable that at least a part of the ethylene in the mixed gas is recycled to the reactor and reused as a reaction raw material.
  • by-products include olefins, paraffins, aromatic compounds, and water having a carbon number or higher.
  • Propylene, ethylene, by-products and reaction products as reactor outlet gas products
  • the mixed gas containing the diluent and the diluent may be introduced into a known separation / purification facility, and recovered, purified, recycled, and discharged according to the respective components.
  • the components inert to the reaction can be reused as a diluent.
  • the method for producing polypropylene of the present invention is a method for producing polypropylene using propylene produced by the above-described method for producing propylene of the present invention.
  • the method for producing this polypropylene is not particularly limited, and propylene may be polymerized in the presence of a propylene polymerization catalyst according to a conventional method.
  • This aluminosilicate has a short pore diameter and a major diameter of 0.38 nm.
  • the conversion rate is ethanol-ethylene conversion rate ((number of moles of ethanol fed to number of moles of ethylene at reactor outlet)). / Moles of ethanol supplied). Also generate each The selectivity of the product was calculated as the carbon mol% of the component excluding ethylene in the reactor outlet gas, and the propylene yield was calculated as the product of ethanol-ethylene conversion and propylene selectivity.
  • the space velocity of ethanol is 0. Ethanol concentration 30 vol 0/0, except for changing the nitrogen to 70% by volume, the reaction was carried out in the same catalysts and reaction conditions as in Example 1. 4.5 hours after the start of the reaction, the product was analyzed by gas chromatography.
  • the catalyst is a proton type aluminosilicate with LEV structure.
  • the catalyst is a proton type aluminosilicate with MFI structure (MH—ZSM5), SiO 2 / Al 2 O 311 (molar ratio), and pores with a short diameter of 0.51 nm and a long diameter of 0.55 nm
  • the reaction was carried out under the same reaction conditions as in Example 1 except that a pore having a minor axis of 0.53 nm and a major axis of 0.56 nm was used. 2.0 hours after the start of the reaction, the product was analyzed by gas chromatography. Table 1 shows the reaction results.
  • the reaction was carried out under the same reaction conditions as in Example 1 except that peptone type silicoaluminophosphate (SAP O_34) having a CHA structure synthesized according to US Pat. No. 4440871 was used as a catalyst. 3.3 hours after the start of the reaction, the product was analyzed by gas chromatography. Table 1 shows the reaction results. This silicoaluminophosphate has pores with a short diameter and a long diameter of 0 ⁇ 38 nm.
  • SAP O_34 peptone type silicoaluminophosphate having a CHA structure synthesized according to US Pat. No. 4440871
  • a catalyst As a catalyst, it is a proton type aluminosilicate with FAU structure.
  • the present invention provides a method for obtaining propylene in a high yield with at least one of ethanol and ethylene, and a method for producing polypropylene from the propylene produced by this method.
  • the present invention can reduce the environmental burden by producing polypropylene, which is a general-purpose resin, using propylene, which is produced using bioethanol, which is a plant-derived raw material.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé de fabrication de propylène à partir d'au moins un élément parmi l'éthanol et l'éthylène, avec un rendement élevé. L'invention concerne notamment un procédé de fabrication de propylène, au moins un élément parmi l'éthanol et l'éthylène étant mis en contact avec un catalyseur dans une cuve de réaction. Ce procédé de fabrication de propylène est caractérisé en ce qu'un aluminosilicate ayant une taille de pores inférieure à 0,5 nm est utilisé en tant que catalyseur. Le catalyseur est de préférence composé d'un aluminosilicate comportant un cycle à 8 ou 9 éléments, plus préférablement un aluminosilicate ayant une structure CHA. La fabrication de polypropylène en tant que résine polyvalente à partir de propylène, lui-même produit à partir de bioéthanol, une matière première d'origine végétale, permet de réduire l'impact sur l'environnement.
PCT/JP2007/056732 2006-03-30 2007-03-28 Procede de fabrication de propylene WO2007114195A1 (fr)

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KR1020087023582A KR101382804B1 (ko) 2006-03-30 2007-03-28 프로필렌의 제조 방법
CN2007800113440A CN101410353B (zh) 2006-03-30 2007-03-28 丙烯的制造方法

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JP2006094538 2006-03-30
JP2006-094538 2006-03-30

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WO2009037992A1 (fr) * 2007-09-18 2009-03-26 Asahi Kasei Chemicals Corporation Procédé de fabrication de propylène
JP2009221030A (ja) * 2008-03-13 2009-10-01 Asahi Kasei Chemicals Corp シリカ成形体
WO2010101121A1 (fr) * 2009-03-02 2010-09-10 旭化成ケミカルズ株式会社 Procédé de production de propylène
JP2011511036A (ja) * 2008-02-07 2011-04-07 トータル・ペトロケミカルズ・リサーチ・フエリユイ 結晶性シリケート上でのアルコールの脱水
JP2011511037A (ja) * 2008-02-07 2011-04-07 トータル・ペトロケミカルズ・リサーチ・フエリユイ 不活性成分の存在下でのアルコールの脱水
JP2011078962A (ja) * 2009-08-11 2011-04-21 Mitsubishi Chemicals Corp 触媒の再生方法
US8598399B2 (en) 2010-03-08 2013-12-03 Dow Global Technologies Llc Catalyst composition for direct conversion of ethanol to propylene
JP5478253B2 (ja) * 2007-09-18 2014-04-23 旭化成ケミカルズ株式会社 プロピレンの製造方法

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WO2011024299A1 (fr) * 2009-08-30 2011-03-03 豊田通商株式会社 Fibre protégée par un film pour garniture intérieure d'automobile et élément intérieur d'automobile
WO2024014878A1 (fr) * 2022-07-12 2024-01-18 경상국립대학교 산학협력단 Composite plastique biosourcé comprenant du polypropylène biosourcé, son procédé de fabrication et ses utilisations

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JPH04217928A (ja) * 1990-03-23 1992-08-07 Sued Chemie Ag 低級オレフィンの製造方法
JP2005520763A (ja) * 2002-03-15 2005-07-14 エクソンモービル・ケミカル・パテンツ・インク 高シリカシャバサイト、その合成及びオキシジェネート類のオレフィン類への変換におけるその使用
JP2005232121A (ja) * 2004-02-23 2005-09-02 Mitsubishi Chemicals Corp プロピレンの製造方法

Cited By (11)

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WO2009037992A1 (fr) * 2007-09-18 2009-03-26 Asahi Kasei Chemicals Corporation Procédé de fabrication de propylène
JP5478253B2 (ja) * 2007-09-18 2014-04-23 旭化成ケミカルズ株式会社 プロピレンの製造方法
US9192922B2 (en) 2007-09-18 2015-11-24 Asahi Kasei Chemicals Corporation Propylene production process
JP2011511036A (ja) * 2008-02-07 2011-04-07 トータル・ペトロケミカルズ・リサーチ・フエリユイ 結晶性シリケート上でのアルコールの脱水
JP2011511037A (ja) * 2008-02-07 2011-04-07 トータル・ペトロケミカルズ・リサーチ・フエリユイ 不活性成分の存在下でのアルコールの脱水
US9061954B2 (en) 2008-02-07 2015-06-23 Total Research & Technology Feluy Dehydration of alcohols on crystalline silicates
JP2009221030A (ja) * 2008-03-13 2009-10-01 Asahi Kasei Chemicals Corp シリカ成形体
WO2010101121A1 (fr) * 2009-03-02 2010-09-10 旭化成ケミカルズ株式会社 Procédé de production de propylène
US8450551B2 (en) 2009-03-02 2013-05-28 Asahi Kasei Chemicals Corporation Method for producing propylene
JP2011078962A (ja) * 2009-08-11 2011-04-21 Mitsubishi Chemicals Corp 触媒の再生方法
US8598399B2 (en) 2010-03-08 2013-12-03 Dow Global Technologies Llc Catalyst composition for direct conversion of ethanol to propylene

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TW200800853A (en) 2008-01-01
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