EP1802596A1 - Procede de fabrication d'olefinoxydes et de peroxydes, reacteur et utilisation - Google Patents

Procede de fabrication d'olefinoxydes et de peroxydes, reacteur et utilisation

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Publication number
EP1802596A1
EP1802596A1 EP05787485A EP05787485A EP1802596A1 EP 1802596 A1 EP1802596 A1 EP 1802596A1 EP 05787485 A EP05787485 A EP 05787485A EP 05787485 A EP05787485 A EP 05787485A EP 1802596 A1 EP1802596 A1 EP 1802596A1
Authority
EP
European Patent Office
Prior art keywords
reaction
catalyst
reaction space
reactor
compound
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.)
Withdrawn
Application number
EP05787485A
Other languages
German (de)
English (en)
Inventor
Steffen Schirrmeister
Bernd Langanke
Karsten BÜKER
Frank Becker
Johannes Albrecht
Georg Markowz
Rüdiger Schütte
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.)
ThyssenKrupp Industrial Solutions AG
Original Assignee
Uhde GmbH
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 Uhde GmbH filed Critical Uhde GmbH
Publication of EP1802596A1 publication Critical patent/EP1802596A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0215—Coating
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
    • C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
    • 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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
    • 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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/248—Reactors comprising multiple separated flow channels
    • B01J19/249—Plate-type reactors
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/024—Multiple impregnation or coating
    • B01J37/0246—Coatings comprising a zeolite
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00783—Laminate assemblies, i.e. the reactor comprising a stack of plates
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00819—Materials of construction
    • B01J2219/00835—Comprising catalytically active material
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00873—Heat exchange
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00891—Feeding or evacuation
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/24—Stationary reactors without moving elements inside
    • B01J2219/2401—Reactors comprising multiple separate flow channels
    • B01J2219/245—Plate-type reactors
    • B01J2219/2451—Geometry of the reactor
    • B01J2219/2453—Plates arranged in parallel
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/24—Stationary reactors without moving elements inside
    • B01J2219/2401—Reactors comprising multiple separate flow channels
    • B01J2219/245—Plate-type reactors
    • B01J2219/2461—Heat exchange aspects
    • B01J2219/2462—Heat exchange aspects the reactants being in indirect heat exchange with a non reacting heat exchange medium
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/24—Stationary reactors without moving elements inside
    • B01J2219/2401—Reactors comprising multiple separate flow channels
    • B01J2219/245—Plate-type reactors
    • B01J2219/2469—Feeding means
    • B01J2219/247—Feeding means for the reactants
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/24—Stationary reactors without moving elements inside
    • B01J2219/2401—Reactors comprising multiple separate flow channels
    • B01J2219/245—Plate-type reactors
    • B01J2219/2476—Construction materials
    • B01J2219/2477—Construction materials of the catalysts
    • B01J2219/2479—Catalysts coated on the surface of plates or inserts

Definitions

  • the present invention is directed to a process for the preparation of olefin oxides, in particular propene oxide, and peroxides by heterogeneously catalyzed gas phase oxidation in a wall reactor and to the use of particularly suitable reactors in the gas phase oxidation.
  • Another method uses a Si-containing catalyst and Lets ⁇ temperatures 425-500 0 C (comp. Gusenov HM et al. In Azerb. Khim. Zh. (1984), 47-51). In this case, a tubular reactor is used and the propene conversion is in the range of 15 to 65%.
  • Still another method uses an Fe-containing catalyst (see TM Nagiev et al., Neftekhimiya 31 (1991), 670-675).
  • the reaction yields are about 30% and the catalyst has a very short life.
  • Higher service lives and a further reduction in the reaction temperature can be achieved with an Fe '"-OH-protoporphyrin catalyst bound to aluminum oxide, which is heated at 16O 0 C and a temperature of about 16O 0 C
  • Wall reactor more precisely a microreactor
  • Kruppa and Schüth have also investigated the epoxidation reaction in a microreactor (IMRET 7, 2003).
  • Another object of the present invention is to provide a reactor which is particularly suitable for the gas-phase reaction with and peroxidic compounds.
  • the present invention relates to a process for preparing an olefin oxide by heterogeneously catalyzed gas phase epoxidation of an olefin with a peroxidic compound in the presence of water and optionally an inert gas comprising the measures: i) carrying out the gas phase epoxidation at temperatures above 100 0 C, ii) using a reactor of at least one reaction space, of which at least one dimension is smaller than 10 mm, iii) wherein the surface of the reaction space containing a layer
  • reaction space contains catalyst, preferably coated with catalyst or partially coated.
  • wall reactors are to be understood as meaning those reactors in which at least one of the dimensions of the reaction space or the reaction spaces is less than 10 mm, preferably less than 1 mm, particularly preferably less than 0.5 mm.
  • the catalyst content of the reaction space / reaction spaces can also be extended to collection or distribution spaces, wherein a different catalyst content to the reaction space in these areas may be present.
  • the reactor may have one or preferably a plurality of reaction spaces, preferably a plurality of reaction spaces running parallel to one another.
  • the dimensioning of the reaction spaces can be arbitrary, provided at least one dimension moves in the range of less than 10 mm.
  • the reaction spaces may have round, ellipsoidal, triangular or polygonal, in particular rectangular or square cross sections.
  • the or a dimension of the cross section is smaller than 10 mm, that is at least one side length or the or a diameter.
  • the cross section is rectangular or round and only one dimension of the cross section, ie one side length or the diameter moves in the range of less than 10 mm.
  • the construction material of the reactor can be arbitrary provided that it is stable under the reaction conditions, allows sufficient heat dissipation and the surface of the reaction space with the above-mentioned special materials is completely or partially coated.
  • the reactor can thus consist of metallic materials, although its reaction space or reaction spaces with aluminum oxide, zirconium oxide, tantalum oxide, silicon dioxide, tin oxide, glass and / or enamel is coated.
  • Surface layer of the reaction space is in the range of 20 to 100 wt.%, Based on the material forming the surface layer of the reaction space.
  • the reactor or at least the parts enclosing the reaction space are made of aluminum or one
  • reaction space contains all or part of the catalyst.
  • the surface of the reaction space is partially or completely coated with catalyst.
  • the catalyst can be applied to the special surface of the substrate or the reaction space is completely or partially filled with finely divided, optionally supported catalyst.
  • the catalyst filled or coated volume is porous and permeable under the reaction conditions in the reactor to the reactants so that they can also contact the particular materials.
  • the present invention thus also relates to a process for preparing a peroxidic compound by heterogeneously catalyzed gas phase reaction comprising the steps: v) carrying out the reaction by reacting a precursor for the peroxidic compound with oxygen and / or an oxygen-containing compound to the peroxidic compound at temperatures above 100 0 C, vi) use of a reactor having at least one reaction space of which at least one dimension is smaller than 10 mm, vii) in which the surface of the reaction space contains a layer
  • reaction space optionally contains catalyst, preferably coated with catalyst or partially coated.
  • Precursor of peroxidic compounds is generally oxygen.
  • the invention involves the production of hydrogen peroxide from hydrogen and oxygen in the special reactor.
  • organic molecules can be reacted with hydrogen peroxide to organoperoxidic compounds such as peracetic acid.
  • the invention also relates to a reactor for reaction with or to peroxidic compounds comprising: a) at least one reaction space of which at least one dimension is smaller than 10 mm, b) the surface of the reaction space has a layer containing alumina, zirconia, tantalum oxide, Silicon dioxide, tin oxide, glass and / or enamel, and c) the reaction space contains catalyst, preferably the surface of the reaction space is coated with catalyst or partially coated.
  • Another object of the invention is the use of specially coated reactors in the gas phase oxidation with peroxidic compounds or in the synthesis of peroxidic compounds, especially in heterogeneously catalyzed gas phase reactions.
  • the gas phase epoxidation is carried out in a microreactor having a plurality of vertically or horizontally and parallelly arranged spaces, which have at least one supply line and one discharge, wherein the spaces are formed by stacked plates or layers, and a part of the spaces is reaction spaces, of which at least one dimension is in the range of less than 10 mm, and the other part of the rooms is heat transport spaces, the supply lines to the reaction spaces having at least two distribution units and the outlets from the reaction spaces to at least one Collection unit are connected, wherein the heat transfer between reaction and heat transport spaces is carried by at least one common room wall, which is formed by a common plate.
  • a microreactor of this type which is particularly preferably used has spacer elements arranged in all chambers, contains at least partially catalyst material applied to the inner walls of the reaction chambers, has a hydraulic diameter which is defined as the quotient of four times the circumferential length of the free flow cross-section in the reaction chambers less than 4000 microns, preferably less than 1500 microns, and more preferably less than 500 microns, and a ratio between the perpendicular smallest distance between two adjacent spacer elements to the slot height of the reaction space after a coating with catalyst of less than 800 and greater than or equal to 10, preferably less than 450, and more preferably less than 100.
  • olefins it is possible to use all compounds which have one or more double bonds. Straight-chain or branched as well as cyclic olefins can be used. The olefins can also be used as mixtures.
  • the olefinic starting materials have at least two carbon atoms. Olefins of any number of carbon atoms can be used, provided that they are sufficiently thermally stable under the conditions of gas phase epoxidation.
  • olefins having 2 to 6 C atoms Preference is given to using olefins having 2 to 6 C atoms. Examples thereof are ethene, propene, 1-butene, 2-butene, isobutene and also pentenes and hexenes, including cyclohexene and cyclopentene, or mixtures of two or more of these olefins, but also higher olefins.
  • the process is particularly preferably suitable for the preparation of propene oxide from propene.
  • hydro or organic peroxides can be used with any hydrocarbon radicals, provided that they are sufficiently thermally stable under the conditions of the gas phase reaction.
  • hydrogen peroxide can be used all evaporable compositions containing H 2 O 2 .
  • aqueous solutions of 30 to 90% by weight of hydrogen peroxide are used, which are evaporated and fed to the wall reactor.
  • the gaseous hydrogen peroxide is recovered by evaporation in a suitable apparatus.
  • highly concentrated H 2 O 2 solutions are preferably fed to the evaporator. As a result, the energy consumption is reduced.
  • any catalysts for the gas phase oxidation of olefins can be used with hydrogen peroxide.
  • One class of suitable and preferred catalysts are molecular sieves, especially synthetic zeolites.
  • a particularly preferred catalyst from the series of molecular sieves is based on titanium-containing molecular sieves of the general formula (SiO 2 ) i -x (TiO 2 ) x , such as titanium silicalite-1 (TS1) with MFI crystal structure, titanium silicalite-2 (TS-2) MEL crystal structure, titanium beta zeolite with BEA crystal structure and titanium silicalite-48 having the crystal structure of zeolite ZSM 48.
  • the TiO 2 content in TS-1 is preferably in the range of 2 to 4%. Titanium silicalites are commercially available. Instead of pure titanium silicalites and combination products, which except
  • Titansilikalit also amorphous or crystalline oxides such as SiO 2 , TiO 2 , Al 2 O 3 and / or ZrO 2 included.
  • crystallites of titanium silicalite may be homogeneously distributed with the crystallites of the other oxides and form granules or be located as an outer shell on a core of other oxides.
  • organometallic catalysts for example organo-iron (protoporphyrin) or organo-titanium compounds on a suitable support.
  • organometallic catalysts for example organo-iron (protoporphyrin) or organo-titanium compounds on a suitable support.
  • preferred catalysts used are preferably inorganic, in particular oxidic compounds which contain as catalyst-active element one or more elements of the 4th to 6th subgroup of the Periodic Table and / or an arsenic and / or selenium compound.
  • the catalytic effect of these compounds is, without excluding other mechanisms, seen in the fact that the peroxidic starting material is activated by the porous structure of the catalyst and / or by the ability of the catalyst for the reversible formation of peroxo compounds.
  • catalysts examples include vanadium oxides, vanadates and their h ⁇ Cb adducts.
  • epoxidation catalysts contain molybdenum or tungsten.
  • molybdenum or tungsten examples are MoO 3 and WO 3 , molybdenum and tungstic acids, alkali metal and alkaline earth metal alkoxide and tungstates, unless their basicity leads to hydrolysis of the epoxide, homo- and heteropolymolybdates and tungstates
  • H2Ü2 adducts of the mentioned classes of substances such as peroxomolybdic acid, peroxotungstic acid, Peroxomolybdate and Peroxowolframate, which can also be formed in situ during the epoxidation of other Mo and W compounds.
  • Catalysts for the production of hydrogen peroxide are e.g. Gold, palladium or other precious metals on suitable supports, e.g. on carbons or on SiO 2.
  • suitable supports e.g. on carbons or on SiO 2.
  • no catalyst is generally needed for the preparation of organoperoxidischer compounds.
  • the catalyst was combined with a binder which was inert to the epoxidation reaction Part or applied to all walls of the reaction space.
  • a particular challenge lies in the properties of the binder that are as inert as possible to the gaseous peroxidic compound.
  • inactive binders for liquid applications. However, most substances show marked differences in their catalytic decomposition properties compared with gaseous peroxidic compounds.
  • a coating containing aluminum, silica or silicate has proven to be particularly preferred.
  • These preferred catalytic coatings can be formed by mixing the inactive binder with the active component, preferably with the powdered active component, by shaping and annealing.
  • catalysts are used whose effective component is applied to a porous support.
  • a particularly large internal volume can be generated, which leads to particularly high reaction yields
  • the starting materials for the processes according to the invention are fed to the wall reactor.
  • the feeds may contain other components, for example water vapor and / or other inert gases.
  • the processes are typically carried out continuously.
  • olefin to be epoxidized can in principle be used in any ratio to the peroxidic component, preferably to the hydrogen peroxide.
  • the gas phase reactions are carried out at a temperature above 100 0 C, preferably at a temperature above 140 0 C.
  • Preferred reaction temperatures are in the range 140-700 0 C, in particular in the range of 140 to 250 ° C.
  • the gas phase reactions take place in a pressure range from 0.05 to 4 MPa, preferably 0.1 to 0.6 MPa.
  • the work-up of the reaction mixture can be carried out in the manner known to those skilled in the art.
  • the inventive method is characterized by the simple reaction, high space-time yields at the same time high selectivity of the valuable oxidizing agent.
  • the evaporator made of glass 100 0 C
  • the gaseous mixture leaving the evaporator and consisting of 18 ml / min of H 2 O 2 , 53 ml / min of propene, 247 ml / min of N 2 and the water fractions was reacted at different temperatures of 100 to 180 ° C. in the microreactor.
  • the reactor was coated therewith with 0.3 g of titanium silicalite-1 catalyst.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé destiné à des réactions faisant intervenir des composés peroxydiques ou produisant des composés peroxydiques dans un réacteur à parois dont la chambre de réaction présente un revêtement matériel spécifique. Le procédé selon l'invention permet d'obtenir de meilleurs rendements espace-temps et de meilleures sélectivités.
EP05787485A 2004-10-15 2005-09-16 Procede de fabrication d'olefinoxydes et de peroxydes, reacteur et utilisation Withdrawn EP1802596A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004050506A DE102004050506A1 (de) 2004-10-15 2004-10-15 Verfahren zur Herstellung von Olefinoxiden und Peroxiden, Reaktor und dessen Verwendung
PCT/EP2005/009965 WO2006042598A1 (fr) 2004-10-15 2005-09-16 Procede de fabrication d'olefinoxydes et de peroxydes, reacteur et utilisation

Publications (1)

Publication Number Publication Date
EP1802596A1 true EP1802596A1 (fr) 2007-07-04

Family

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Application Number Title Priority Date Filing Date
EP05787485A Withdrawn EP1802596A1 (fr) 2004-10-15 2005-09-16 Procede de fabrication d'olefinoxydes et de peroxydes, reacteur et utilisation

Country Status (17)

Country Link
US (1) US20080306288A1 (fr)
EP (1) EP1802596A1 (fr)
JP (1) JP2008516900A (fr)
KR (1) KR20070063004A (fr)
CN (1) CN101044129A (fr)
AU (1) AU2005297530A1 (fr)
BR (1) BRPI0516517A (fr)
CA (1) CA2584049A1 (fr)
DE (1) DE102004050506A1 (fr)
EA (1) EA013086B1 (fr)
EG (1) EG24502A (fr)
HR (1) HRP20070150A2 (fr)
MX (1) MX2007004501A (fr)
NO (1) NO20072459L (fr)
NZ (1) NZ554394A (fr)
WO (1) WO2006042598A1 (fr)
ZA (1) ZA200702469B (fr)

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CN109999821B (zh) * 2019-03-12 2021-11-16 内蒙古工业大学 一种表面处理的铝合金催化剂的制备及其应用
CN112979587B (zh) * 2019-12-12 2022-12-02 中国科学院大连化学物理研究所 一种微通道反应器合成环氧丙烷的方法
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EA013086B1 (ru) 2010-02-26
NO20072459L (no) 2007-06-29
CA2584049A1 (fr) 2006-04-27
ZA200702469B (en) 2008-12-31
AU2005297530A1 (en) 2006-04-27
KR20070063004A (ko) 2007-06-18
DE102004050506A1 (de) 2006-04-20
US20080306288A1 (en) 2008-12-11
NZ554394A (en) 2009-10-30
JP2008516900A (ja) 2008-05-22
EA200700873A1 (ru) 2007-08-31
MX2007004501A (es) 2007-05-09
CN101044129A (zh) 2007-09-26
HRP20070150A2 (en) 2007-08-31
EG24502A (en) 2009-08-18
WO2006042598A1 (fr) 2006-04-27
BRPI0516517A (pt) 2008-09-16

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