EP2029274A1 - Catalyseur stable à la température pour l'oxydation en phase gazeuse - Google Patents

Catalyseur stable à la température pour l'oxydation en phase gazeuse

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Publication number
EP2029274A1
EP2029274A1 EP07725054A EP07725054A EP2029274A1 EP 2029274 A1 EP2029274 A1 EP 2029274A1 EP 07725054 A EP07725054 A EP 07725054A EP 07725054 A EP07725054 A EP 07725054A EP 2029274 A1 EP2029274 A1 EP 2029274A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
ruthenium
oxidation
carbon nanotubes
catalyst according
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Withdrawn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
EP07725054A
Other languages
German (de)
English (en)
Inventor
Aurel Wolf
Leslaw Mleczko
Oliver Felix-Karl SCHLÜTER
Stephan Schubert
Jürgen KINTRUP
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.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
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 Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP2029274A1 publication Critical patent/EP2029274A1/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Withdrawn legal-status Critical Current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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon
    • B01J21/185—Carbon nanotubes
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/462—Ruthenium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • 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
    • B01J37/03—Precipitation; Co-precipitation
    • B01J37/031—Precipitation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/01—Chlorine; Hydrogen chloride
    • C01B7/03—Preparation from chlorides
    • C01B7/04—Preparation of chlorine from hydrogen chloride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B33/00—Oxidation in general

Definitions

  • the present invention relates to a catalyst for oxidation reactions, comprising at least one active ingredient in the catalysis of oxidation reactions and a carrier therefor, characterized in that the carrier consists of carbon nanotubes.
  • the catalyst is characterized by higher stability and activity compared to prior art catalysts.
  • ruthenium for example, is used in particular as a reduction catalyst or as an oxidation catalyst (Handbook of Heterogeneous Catalysis).
  • a typical example of the use of ruthenium in an oxidation reaction is, for example, the reaction of hydrogen chloride with oxygen, as described in DE 1567788. Due to the high temperatures required here (about 350 ° C.), ruthenium is applied to oxidic carriers.
  • Ru catalysts are used mainly in liquid phases or electrochemical applications.
  • Ru / C catalysts are used as oxidation catalysts for the oxidation of methanol in a fuel cell with a carbon-supported platinum-ruthenium catalyst.
  • RuJC catalyst is used in the oxidation of carbon monoxide [Mater. Res. Soc. Symp. Proceedings 756 (2003) 397-402], as well as together with titanium in the oxidation of ethanol [J. Appl. Electrochem. 30 (4) (2000) 467-474].
  • multi-wall carbon nanotubes are increasingly used as supports for catalytically active metals due to their high electrical conductivity
  • Nanotubes replace some or all of the conventionally used Leitruß.
  • Such electrodes are often used in fuel cells, so for the oxidation of
  • multi-wall carbon nanotubes are used for reactions at high temperatures because of their stability against oxidative attack at high temperatures, as catalyst without further catalytic component.
  • they are used as the oxidation catalyst in the oxidative dehydrogenation of
  • carbon nanotubes find application in the electrochemical oxidation of catecholamines and catechols [Analyst 131 (2) (2006) 262-267], as well as glutathione [Electrochimica Acta 51 (15) (2006) 3046-3051 and in combination with platinum in the electrochemical Oxidation of cysteine [Analytica Chimica Acta 557 (1-2) (2006) 52-56].
  • the use of multi-wall carbon nanotubes in combination with the catalytically active component ruthenium is not known.
  • Oxidation under more severe conditions in terms of temperature and oxygen partial pressure is the method of catalytic hydrogen chloride oxidation with oxygen developed by Deacon in 1868:
  • the oxidation of hydrogen chloride to chlorine is an equilibrium reaction.
  • the position of the equilibrium shifts with increasing temperature to the detriment of the desired end product. It is therefore advantageous to use catalysts with the highest possible activity, which allow the reaction to proceed at low temperature.
  • the first catalysts for the hydrogen chloride oxidation with the catalytically active component ruthenium were already described in 1965 in DE 1 567 788. In this case starting from RuC13. Further Ru-based catalysts with the active material ruthenium oxide or ruthenium mixed oxide were claimed in DE-A 197 48 299.
  • the content of ruthenium oxide is 0, 1 wt .-% to 20 wt .-% and the average particle diameter of ruthenium oxide 1.0 nm to 10.0 nm.
  • Ru starting compounds such as, for example, ruthenium-carbonyl complexes, ruthenium salts of inorganic acids, ruthenium-nitrosyl complexes, ruthenium-amine.
  • Complex ruthenium complexes of organic amines or ruthenium-acetylacetonate complexes.
  • titanium dioxide in the form of rutile was used as carrier.
  • Ru catalysts have a fairly high activity, they tend to sinter and thus deactivate at higher temperatures. To increase the economy, however, a further increase in activity with good long-term stability is necessary.
  • the previously developed supported ruthenium oxidation catalysts have insufficient activity or stability. For example, for the hydrogen chloride oxidation, such catalysts have insufficient activity. Although the activity can be increased by increasing the reaction temperature, this leads to sintering / deactivation or loss of the catalytic component.
  • the object of the present invention was to provide a catalyst which effects oxidation reactions such as the oxidation of hydrogen chloride at low temperatures and with high activities.
  • Nanotubes due to a special interaction between catalytically active
  • the present invention thus provides a catalyst for oxidation reactions comprising at least one active ingredient in the oxidation reaction catalysis and a carrier therefor, characterized in that the carrier is based on carbon nanotubes.
  • a catalyst in which the catalytically active ingredient is applied to the carrier in the form of an aqueous solution or suspension and the solvent is subsequently removed.
  • a catalyst which is characterized in that the catalytically active constituent is applied to the carrier as an aqueous solution or suspension of ruthenium halides, oxides, hydroxides or oxyhalides, in each case alone or in any desired mixture, and the solvent is then removed is.
  • An oxidation reaction means such a reaction in which at least one element involved in the reaction is oxidized, i. receives a higher oxidation number.
  • Carbon nanotubes are understood to mean mainly cylindrical carbon tubes with a diameter of preferably 3 to 150 nra. The length is a multiple, preferably at least 100 times the diameter. These tubes consist of layers of ordered carbon atoms and have a different nucleus in morphology. These carbon nanotubes are also known, for example, as “carbon fibrils” or “hollow The described carboniianotubes have due to their
  • Carbon nanotubes especially those with a diameter of 3 to 150 nm and an aspect ratio length: diameter (L: D)> 100, are preferred by decomposition of hydrocarbons on a heterogeneous catalyst, the Mn, Co, preferably also in addition molybdenum, and an inert Contains carrier material prepared.
  • the carbon nanotubes are characterized by a high thermal conductivity (> 2000 W / mK) and the fullerene-like structure.
  • the former allows a high heat dissipation of the heat of reaction, as well as the latter a special stabilization of high oxidation states.
  • Another advantage is the significantly higher oxidation stability compared to amorphous carbon.
  • the carbon nanotubes used can be single-walled or multi-walled, preference is given to multi-walled, more preferably a wall number of 3 to 50.
  • the diameter is in particular 1 to 500 nm, preferably 2 to 50 nm, particularly preferably 2 to 30 nm.
  • the length of the carbon nanotubes is in particular 10 nm-10 mm, preferably 100 nm-1 mm, particularly preferably 1 to 100 ⁇ m.
  • the specific surface area of the carbon nanotubes is preferably in the range from 20 to 1000 mVg, particularly preferably from 100 to 40 mVg according to BET.
  • the carbon nanotubes used can generally be used "as-produced” or else purified beforehand
  • surface-modified carbon nanotubes are used, surface modification being the oxidative treatments of the carbon nanotubes generally known to those skilled in the art with oxidizing compounds such as acids such as HNO 3 , H 2 SO 4 , HClO 4 and mixtures thereof, or other oxidizing media such as H 2 O 2 , O 2 , O 3 , CO 2 , etc.
  • oxidizing compounds such as acids such as HNO 3 , H 2 SO 4 , HClO 4 and mixtures thereof, or other oxidizing media such as H 2 O 2 , O 2 , O 3 , CO 2 , etc.
  • other modifications such as functionalization with amine groups are also known.
  • Such carbon nanotubes and processes for their preparation are described, for example, in WO2006 / 050903 A2, the disclosure content of which fully, in particular with regard to the carbon nanotubes described therein, belongs to the disclosure content of the present invention. They are also commercially available as Baytubes® from Bayer MaterialScience AG.
  • the catalytically active main component are all constituents which catalyze an oxidation reaction.
  • the following elements or compounds thereof are suitable: ruthenium, osmium, rhodium, iridium, palladium, platinum, copper, silver, gold, rhenium, bismuth, cobalt, iron or mixtures thereof.
  • ruthenium and its compounds are used.
  • Ruthenium is in oxidic form or as a chloride compound or as
  • the catalytically active component can be applied to the support in a non-oxidic form and is converted into the oxidized form in the course of the reaction.
  • the loading of the catalytically active component is usually in the range from 0.1 to 80% by weight, preferably in the range from 1 to 50% by weight, more preferably in the range from 1 to 25% by weight, based on the total mass Catalyst and carrier.
  • the catalytic component can be applied by various methods. For example, but not limited to, wet and wet impregnation of a support with suitable starting or starting compounds in liquid or collodial form, up and co-impingement methods, as well as ion exchange and gas phase coating (CVD, PVD) may be employed. Preference is given to a combination of impregnation and subsequent precipitation with reducing (preferably hydrogen, hydrides or hydrazine compounds) or alkaline substances (preferably NaOH, KOH or ammonia).
  • reducing preferably hydrogen, hydrides or hydrazine compounds
  • alkaline substances preferably NaOH, KOH or ammonia
  • Suitable promoters are basic metals (for example alkali, alkaline earth and rare earth metals), preference is given to alkali metals, in particular Na and Cs, and alkaline earth metals, particular preference to alkaline earth metals, in particular Sr and Ba.
  • the promoters may, but are not limited to, be applied to the catalyst by impregnation and CVD processes, preference being given to impregnation, particularly preferably after application of the main catalytic component.
  • various dispersion stabilizers such as scandium compounds, manganese oxides and lanthanum oxides can be used.
  • the stabilizers are preferably applied together with the main catalytic component by impregnation and / or precipitation.
  • the catalysts can be dried under atmospheric pressure or preferably under reduced pressure under a nitrogen, argon or air atmosphere at 40 to 200 ° C. The drying time is preferably 10 minutes to 6 hours.
  • the catalysts can be used uncalcined or calcined.
  • the calcination can be carried out in reducing, oxidizing or inert phase, preferably the calcination in an air or nitrogen stream.
  • the calcination takes place in the absence of oxygen in a temperature range of 150 to 600 0 C, preferably in the range 200 to 300 ° C. In the presence of oxidizing gases, the calcination takes place in a temperature range from 150 to 400 ° C., preferably in the range from 200 to 300 ° C.
  • the catalytic process known as the Deacon process is preferably used as described above.
  • hydrogen chloride is oxidized with oxygen in an exothermic equilibrium reaction to chlorine, whereby water vapor is obtained.
  • the reaction temperature is usually 150 to 450 0 C, the usual reaction pressure is 1 to 25 bar. Since it is an equilibrium reaction, it is expedient to work at the lowest possible temperatures at which the catalyst still has sufficient activity.
  • oxygen in excess of stoichiometric amounts of hydrogen chloride. For example, a two- to four-fold excess of oxygen is customary. Since no loss of selectivity is to be feared, it may be economically advantageous to work at relatively high pressure and, accordingly, longer residence time than normal pressure.
  • Suitable preferred catalysts for the Deacon process include ruthenium oxide, ruthenium chloride or other ruthenium compounds supported on silica, alumina, titania or zirconia. Suitable catalysts can be obtained, for example, by applying ruthenium chloride to the support and then drying or drying and calcining. Suitable catalysts may, in addition to or instead of a ruthenium compound, also contain compounds of other noble metals, for example gold, palladium, platinum, osmium, iridium, silver, copper or rhenium. Suitable catalysts may further contain chromium (III) oxide.
  • the catalytic hydrogen chloride oxidation may be adiabatic or preferably isothermal or approximately isothermal, batchwise, but preferably continuously or as a fixed bed process, preferably as a fixed bed process, more preferably in tube bundle reactors to heterogeneous catalysts at a reactor temperature of 180 to 450 0 C, preferably 200 to 400 0th C, more preferably 220 to 35O ° C and a pressure of 1 to 25 bar (1000 to 25000 hPa), preferably 1.2 to 20 bar, more preferably 1.5 to 17 bar and in particular 2.0 to 15 bar are performed ,
  • Typical reactors in which the catalytic hydrogen chloride oxidation is carried out are fixed bed or fluidized bed reactors.
  • the catalytic hydrogen chloride oxidation can preferably also be carried out in several stages.
  • the oxygen can be added either completely together with the hydrogen chloride before the first reactor or distributed over the various reactors. This series connection of individual reactors can also be combined in one apparatus.
  • a further preferred embodiment of a device suitable for the method consists in using a structured catalyst bed in which the catalyst activity increases in the flow direction.
  • Such structuring of the catalyst bed can be done by different impregnation of the catalyst support with active material or by different dilution of the catalyst with an inert material.
  • an inert material for example, rings, cylinders or balls of titanium dioxide, zirconium dioxide or mixtures thereof, alumina, steatite, ceramic, glass, graphite or stainless steel can be used.
  • the inert material should preferably have similar external dimensions.
  • Suitable shaped catalyst bodies starting from carbon nanotubes are shaped bodies with arbitrary shapes, preference being given to tablets, rings, cylinders, stars, carriage wheels or spheres, particular preference being given to spheres, rings, cylinders or star strands as molds.
  • suitable carrier materials with CNTs are silicon dioxide, graphite, rutile or anatase titanium dioxide, zirconium dioxide, aluminum oxide or mixtures thereof, preferably titanium dioxide, zirconium dioxide, aluminum oxide or mixtures thereof, more preferably ⁇ - or ⁇ -aluminum oxide or mixtures thereof.
  • the shaping of the catalyst can take place after or preferably before the impregnation of the support material.
  • the conversion of hydrogen chloride in a single pass may preferably be limited to 15 to 90%, preferably 40 to 85%, particularly preferably 50 to 70%. Unreacted
  • Hydrogen chloride can be partially or completely separated into the catalytic after separation
  • Hydrogen chloride oxidation can be attributed.
  • the volume ratio of hydrogen chloride to oxygen at the reactor inlet is preferably 1: 1 and 20: 1, preferably 2: 1 and 8: 1, more preferably 2: 1 and 5: 1.
  • the heat of reaction of the catalytic hydrogen chloride oxidation can be used advantageously for the production of high-pressure steam. This can be used to operate a Phosgenation and / or distillation columns, in particular of isocyanate
  • the hydrogen chloride oxidation catalyst of the present invention is characterized by high activity at a low temperature. Without being bound by theory, it is believed that the CNTs are effective as stabilizers of high oxidation states (e.g., Ru (VUI)).
  • Example 2 Support of a Catalytically Active Component on Carbon Nanotubes
  • the damp solid was dried h and then calcined at 120 0 C in a vacuum oven 4 at 300 0 C in the air flow, whereby a ruthenium oxide catalyst supported was obtained in the CNT.
  • the product was analyzed by X-ray photoelectron spectroscopy (XPS). As a result, the ruthenium phase was found to be 72% RuO2, 20% RuO3, and 8% RuO4.
  • XPS X-ray photoelectron spectroscopy
  • Example 3 Carrier catalytically active component on titanium dioxide
  • Example 2 a catalyst ruthenium on titanium dioxide (w / w Ru with 4.7 and 10%) was prepared and calcined at 300 ° C in an air stream (3a or 3b).
  • Example 4 Use of the catalysts from Examples 2 and 3 in the HCl oxidation
  • the catalysts from Examples 2 and 3 were in a solid bed in a quartz reaction tube (diameter 10 mm) at 300 0 C with a gas mixture of 80 ml / min (STP) of hydrogen chloride and 80 ml / min (STP) oxygen flows through.
  • the quartz reaction tube was heated by an electrically heated sand fluid bed. After 30 minutes, the product gas stream was passed into 16% potassium iodide solution for 10 minutes. The resulting iodine was then back titrated with 0.1 N thiosulfate standard solution to determine the amount of chlorine introduced. The quantities of chlorine listed in Table 1 were obtained.
  • Example 6 Long-term stability of a CNT-supported catalyst
  • Example 2 The ruthenium-on-CNT catalyst of Example 2 was tested as described in Example 4, but the experimental time was extended and several samples were taken by bubbling into 16% potassium iodide solution for 10 minutes. This results in the chlorine quantities listed in FIG.
  • Example 7 Temperature dependence of the activity of a CNT-supported catalyst
  • Example 2 The ruthenium-on-CNT catalyst of Example 2 was tested as described in Example 4, but the temperature was varied in the range 200 to 300 0 C. Two control measurements at the end prove that no deactivation phenomena occurred during the temperature variation. This results in the chlorine quantities listed in FIG.
  • FIG. 3 shows a transmission electron micrograph of a catalyst according to the invention.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Composite Materials (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Catalyseur pour des réactions d'oxydation, qui contient au moins un ingrédient actif dans la catalyse de réactions d'oxydation, ainsi qu'un support, caractérisé en ce que le support est à base de nanotubes de carbone. Le catalyseur se caractérise par une stabilité et une activité plus élevées, par comparaison aux cataylseurs selon l'état de la technique.
EP07725054A 2006-05-23 2007-05-10 Catalyseur stable à la température pour l'oxydation en phase gazeuse Withdrawn EP2029274A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006024550A DE102006024550A1 (de) 2006-05-23 2006-05-23 Temperaturstabiler Katalysator für die Gasphasenoxidation
PCT/EP2007/004132 WO2007134722A1 (fr) 2006-05-23 2007-05-10 Catalyseur stable à la température pour l'oxydation en phase gazeuse

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EP2029274A1 true EP2029274A1 (fr) 2009-03-04

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EP07725054A Withdrawn EP2029274A1 (fr) 2006-05-23 2007-05-10 Catalyseur stable à la température pour l'oxydation en phase gazeuse

Country Status (9)

Country Link
US (1) US20070274899A1 (fr)
EP (1) EP2029274A1 (fr)
JP (1) JP2009537312A (fr)
KR (1) KR20090017532A (fr)
CN (1) CN101448570A (fr)
DE (1) DE102006024550A1 (fr)
RU (1) RU2440186C2 (fr)
TW (1) TW200803978A (fr)
WO (1) WO2007134722A1 (fr)

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CN101448570A (zh) 2009-06-03
RU2008150587A (ru) 2010-06-27
KR20090017532A (ko) 2009-02-18
WO2007134722A1 (fr) 2007-11-29
JP2009537312A (ja) 2009-10-29
TW200803978A (en) 2008-01-16
RU2440186C2 (ru) 2012-01-20
US20070274899A1 (en) 2007-11-29
DE102006024550A1 (de) 2007-11-29

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