WO2002034672A1 - Verfahren zur herstellung von formselektiven katalysatoren und deren verwendung - Google Patents
Verfahren zur herstellung von formselektiven katalysatoren und deren verwendung Download PDFInfo
- Publication number
- WO2002034672A1 WO2002034672A1 PCT/EP2001/011806 EP0111806W WO0234672A1 WO 2002034672 A1 WO2002034672 A1 WO 2002034672A1 EP 0111806 W EP0111806 W EP 0111806W WO 0234672 A1 WO0234672 A1 WO 0234672A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ammonium
- zeolite catalyst
- zeolite
- metal
- catalysts
- Prior art date
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Classifications
-
- 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
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/86—Catalytic processes
- B01D53/8621—Removing nitrogen compounds
- B01D53/8625—Nitrogen oxides
- B01D53/8628—Processes characterised by a specific catalyst
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/86—Catalytic processes
- B01D53/8668—Removing organic compounds not provided for in B01D53/8603 - B01D53/8665
-
- 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
- B01J29/061—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing metallic elements added to the zeolite
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
-
- 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 invention relates to a process for the production of shape-selective catalysts based on zeolites or mesoporous silicates by incorporating catalytically active metal oxides as non-lattice species in their channel and cavity structure, and the use of the catalysts prepared in this way
- Catalytically active metal ions can be applied evenly by ion exchange or impregnation on the surface or built into the crystal framework.A subsequent reduction to pure metal is possible - Zeolite catalysts are thermally stable up to at least 600 ° C, sometimes even there and by burning off carbon deposits
- Zeolite catalysts which contain metals and / or metal oxides in the crystal lattice are known.
- US Pat. No. 5,756,861 and US Pat. No. 5,672,777 describe a ZSM-5 zeolite for the oxidation of benzenes
- EP 0 889 018 also discloses a zeolite catalyst doped with Fe 2 O 3.
- US 5 110 995 describes very small proportions of catalytically active iron additives in zeolites.
- the foreign metals are usually added in the synthesis of the zeolite in the form of soluble salts, such as nitrates, and incorporated into the crystal composite of the Si / Al lattice by the hydrothermal crystallization at high temperatures. This results in the substitution of an Si atom, with a Bronsted atom Acid center can arise
- Bronsted acid centers are generally generated when metal ions are incorporated into the crystal lattice, while so-called Lewis acid centers are formed when metal oxides are deposited, for example in the channel structure of the zeolite
- the task was to develop a zeolite catalyst which is thermally stable, contains catalytically active metals, metal complexes and / or metal oxides in the manner of a "ship in a bottle” complex and can be used for the oxidation of organic substrates
- the metals introduced via carbonyl, cyano and / or isonitrile complexes can be incorporated into the channel and flute structure of a zeolite in such a way that on the one hand they have a catalytic effect, but on the other hand they have little or no Bronsted acidity , for example by incorporating metal ions into the lattice structure
- the invention is therefore a process for the preparation of subgroup metal-containing zeolite catalysts by hydrothermal synthesis with subsequent calcination, which is characterized in that the subgroup metals are in the form of complexes of the general formula
- the invention furthermore relates to the use of the zeolite catalysts produced according to the invention in processes for the oxidation of organic substrates (for example benzene to phenol or in general for the hydroxylation of aromatic compounds), as a denitrification catalyst (for example in automotive exhaust gas catalysts and in power plants) and in fuel cells
- organic substrates for example benzene to phenol or in general for the hydroxylation of aromatic compounds
- denitrification catalyst for example in automotive exhaust gas catalysts and in power plants
- X and Y represent a volatile component such as water or ammonia in the hydrothermal synthesis of the zeolite catalysts.
- the subgroup metals can thus be pure carbonyl, cyano and / or isonitrile complexes, mixed complexes or else mixed with other volatile ligands Carbonyl, cyano or isonitrile complexes are introduced into the hydrothermal synthesis of the zeolite catalysts.
- Examples of such complexes are, for example, NH 4 [Fe (CO) 4 (CN)], Fe (CO) 4 (CNR), Fe (CNR) 4 (CN) 2 , where R can be an alkyl group, preferably a methyl or ethyl group
- the catalysts produced according to the invention preferably have pores with a diameter below 15 angstroms, particularly preferably a pore diameter of 4 to 7 angstroms.
- a preferred structural form are zeolites of the MFI or ZSM-5, MEL or ZSM-11 type, but also ferrierite and beta
- the subgroup metals are introduced into the catalyst in the form of the complexes of the formula I according to the invention, for example in the form of cyano complexes, isonitrile complexes and / or carbonyl complexes, via a so-called template synthesis.
- the calcination which preferably takes place at temperatures above 500 ° C., finely divided remains Metal oxide in the channel or cavity structure of the zeolite. This metal oxide can, if necessary, be led to the elemental metal by hydrogen.
- the metal oxides formed by the calcination process are preferably used
- the complexes of the formula I used according to the invention should on the one hand be water-soluble, on the other hand they should remain stable in an alkaline environment.
- the subgroup metals are therefore preferred in the form of carbonyl or cyano complexes which are stable in an alkaline environment during the hydrothermal synthesis of the zeolite catalysts the calcination of a removable cation is preferred, in particular an ammonium compound (JNTH) is used here.
- All types of subgroup metal cyanocomplexes are particularly suitable, those with 6 coordination sites, for example with an octahedral structure, with 4 coordination sites, for example with a planar or tetrahedral structure, are particularly preferred are those based on the metals vanadium, chromium, molybdenum, tungsten, manganese, titanium, zirconium, hafnium, technelium, rhenium, iron, ruthenium, osmium, copper, cobalt, rhodium, nickel, iridium, palladium, platinum, gallium, silver and / or gold, ammonium tetracyanomckelat, ammomumtetracyanopalladat, ammoniumtetracyan ⁇ platinat, Ammonium hexacyanoruthenate, ammonium hexacyanoplatinate, ammonium hexacyanocobalate, ammonium hexacyanochromate
- both mononuclear and multinuclear carbonyls of different structures of the above-mentioned metals are suitable, here iron pentacarbonyl is preferred.
- the isonitrile complexes can also be used in pure form or as mixed complexes of the metals of the formula I claimed according to the invention
- iron is used as the catalytically active subgroup metal, this can, according to the invention, be added, for example, as ammonium hexacyanoferrate to the reaction mixture.
- the iron can be in bivalent and / or trivalent form. It is also possible to use other stable complexes, for example in hot water or Add iron carbonyls soluble in alkaline medium, e.g. iron pentacarbonyl
- a conventional titanium silicalite which according to US Pat. No. 4,410,501, for example, can be made from a hydrolyzable one Titanium compound, such as TiCl 4 , TiOCl 2 , tetraalkoxytitanium, preferably tetraethoxytitanium, and is prepared from tetraethylorthosilicate and tetrapropylammonium hydroxide, can be modified according to the invention with ammonium hexacyanoferate or iron carbonyls, as a result of which it is also suitable for the applications according to the invention
- the acidity of the catalysts can be used in the calcination process or a subsequent hydrothermal treatment with a gas containing water vapor
- the zeolite Catalyst at a temperature of 300 to 950 ° C, preferably 450 to 800 ° C with a gas which is from 1 to 100 mol%, preferably from 10 to 100 mol% and very particularly preferably from 50 to 99 mol% of water vapor contains treated Suitable procedures can be found, for example, in WO 95/27560 (1995) or in DE 196 34 406 (1996). Such treatment can further increase the Lewis acidity
- trivalent metals such as aluminum, for example triisobutylaluminum
- the use of trivalent metals, such as aluminum, for example triisobutylaluminum enables the acid strength of the catalyst which may be required to be set precisely if little or almost no presence of acid centers, in particular Bronsted acid centers, is required, such as in the case of oxidation reactions , if the molar ratio of SiO 2 Al 2 O 3 present according to the calcination is at most 1 10 "2.
- the catalyst according to the invention particularly preferably contains no aluminum
- the process according to the invention preferably gives catalysts with a molar ratio of SiO 2 to subgroup metal of 1 10 "D to 1 3 x 10 " 2 (based on the calcined catalyst). It can be advantageous if the molar ratios are in narrower ranges, such as from 1 10 "4 to 1 5 x 10 " 2 or from 1 10 " ⁇ to 1 10 " 2 These ratios apply to SiO 2 to subgroup metal or subgroup metal oxide.
- the molar ratio of SiO 2 is increased Fe 2 O ⁇ preferably between 1 10 "5 (minimum) to 1 1.5 x 10 " 2 (maximum), preferably between 1 10 "4 (minimal) to 1 10 " 2 (maximum), particularly preferably between 1 0, 6 x 10 ⁇ (minimum) to 1 0.9 x 10 "3 (maximum)
- a tetraalkyl orthosilicate such as, for example, tetrahethyl orthosilicate, any other silicate in colloidal form or a silicate of an alkali metal salt, can be used.
- the organic base can be a tetraalkyl ammonium hydroxide, such as tetrapropyl ammonium hydroxide
- the transition metal can be ammonium hexacyanometalate or Ammonium tetracyanometallate added to the reaction mixture
- other stable complexes such as carbonyls soluble in hot water or alkaline medium
- transition metal citrates and transition metal acetylacetonates are unsuitable , because they are permanently installed in the grid and, especially if they are not tetravalent, create strong acid centers
- ammonium hexacyano- or ammonium tetrahedral metalates or metal carbonyls are deposited as oxides on the surface of the zeolite in addition to being deposited on non-lattice sites. This is generally not disadvantageous. In individual cases, an additional catalytic effect can even result from this
- catalysts produced according to the invention can also be used in membranes with pore diameters below 2000 angstroms. In the case of pore diameters of 50 to 1000 angstroms, ultrafiltration membranes are particularly affected. If the catalysts are used in the production of nanofiltration membranes, the pore diameter varies between 5 and 50 angstroms with a pore diameter of Approx. 5 angstroms, these membranes are also suitable for gas separation. In connection with membrane applications, they can also be used in batteries or fuel cells. It is therefore entirely possible to use the zeolite catalyst containing secondary gauze metal in fuel cells
- the catalysts prepared according to the invention can be used in a wide range of industrial chemistry applications, such as isomerization reactions, hydrogenation reactions, dehydration reactions, alkylation reactions, disproportionation reactions, alcohol formation from olefins, epoxidation, coupling reactions, substitution reactions, cycloaddition and cycloreversion reactions, ether formation, alcohol cracking, alcohol cracking Fischer-Tropsch synthesis of alcohols or hydrocarbons, methanol synthesis from synthesis gas or methane, but especially for oxidation reactions of organic substrates with atmospheric oxygen, hydrogen peroxide, organic peroxides or nitrous oxide
- the use of the zeolite catalyst containing subgroup metals according to the invention is particularly preferred for the oxidation of organic substrates, in particular for the production of substituted and unsubstituted hydroxyaromatics.
- the zeolite catalysts containing auxiliary gauze metals according to the invention can be used in particular as catalysts for the production of phenol from benzene
- cresol from toluene phenol from the corresponding benzene derivative substituted with several methyl groups, trimethylphenol and trimethylhydroquinone from trimethylbenzene, nitrophenol from nitrobenzene, halogen-substituted phenol from halogen-substituted benzene or aminophenol from aminobenzene
- the zeolite catalysts according to the invention can also be used as catalysts in the preparation of polyhydroxylated substituted and unsubstituted benzenes such as pyrocatechols, hydroquinones, pyrogallol and phloroglucin.
- polyalkyl substituted benzenes can be hydroxylated using the zeolite catalysts according to the invention.
- trimethylbenzene can be In this way, can be oxidized to trimethylphenol or trimethylhydroquinone.
- tocopherols can be produced using the zeolite catalyst containing secondary yolk metal. This is, for example, a route to synthesize ⁇ -tocopherol (vitamin E), from which it follows that the catalyst according to the invention can be used as Catalyst can be used in the production of ⁇ -tocopherol
- propylene oxide starting from propene and hydrogen peroxide or nitrous oxide. This can take place both in the liquid phase and in the gas phase.
- the zeolite catalyst according to the invention is also to be used for this process
- these catalysts can be used in fuel cells, in particular for coating the Electrodes are used.
- ammonium hexacyanoplatinate can be used, for example, which, after being incorporated as an oxide into the channel and cavity structure of a zeolite, can be reduced to atomic, finely divided platinum with, for example, hydrogen
- the catalysts prepared according to the invention can be used in processes for the oxidation of organic substrates, for example benzene or benzene derivatives, by catalytically oxidizing the substrate with a gas containing dinitrogen monoxide at temperatures between 100-800 ° C., preferably 300-500 ° C.
- the process is particularly suitable for the production of phenol from benzene
- Tubular reactors are usually used for this reaction. Larger test reactors, for example, have an inner diameter of 0.05 m and a length of slightly more than 3.0 m. However, commercially available differential circuit reactors (see examples) are also frequently used for laboratory-scale treatments
- nitrous oxide Various sources can be considered for nitrous oxide.
- the catalytic decomposition of ammonium nitrate at 100-160 ° C with manganese, copper, lead, bismuth, cobalt and nickel catalysts provides a mixture of nitrous oxide, nitrogen oxide and nitrogen dioxide so that the gas does not can be used directly for the oxidation of benzene
- the oxidation of ammonia with oxygen on platinum or bismuth oxide catalysts at 200-500 ° C. and the reaction of nitrogen oxide with carbon monoxide on platinum catalysts are somewhat cheaper. In the first case, however, water is formed as a by-product, in the second case carbon dioxide.
- the nitrous oxide produced in this way can usually not directly used for the benzene oxidation Likewise, the nitrous oxide that is produced in the production of adipic acid cannot be used directly for the oxidation, but must be subjected to a separate cleaning step. In particular, the oxygen and NOx contained in the exhaust gas are disruptive
- nitrous oxide which are based in principle on ammonia and atmospheric oxygen, so that nitrous oxide is available at low cost.
- nitrous oxide N 2 O
- the gas containing nitrous oxide can contain inert gases such as nitrogen and noble gases. Ammonia and water vapor as well as traces of other nitrogen oxides or air can also be present
- Microwave technology can of course also be used in the production of phenol and its derivatives starting from benzene or the corresponding benzene derivatives to increase the selectivity and the conversion. Phenol and its derivatives can be excited to rotate by microwaves and are therefore particularly easily detached from the catalyst
- the activity of the catalyst is determined by GC on the basis of the measured conversion.
- the BET surface areas are all between 400 and 600 m 2 / g, the mean value of the pore size is approximately between 5 and 7 angstroms, determined according to Horvath and Kawazoe
- Iron (IlI) citrate monohydrate 6J3 g
- Ammonium hexacyanoplatinate 1 11 g Average pore size about 6.5 angstroms BET surface area 480 m 2 / g
- Reaction temperatures of 300 to 500 ° C can be set below the A rapidly rotating turbine is attached to the catalytic converter, which draws in the reaction mixture at high speed and feeds it back into the reactor inlet via an external pipe. This procedure can be used to rule out diffusion limitations on the catalyst surface.
- Defined quantities of benzene can be added to this circuit , N 2 O and an inert gas, such as nitrogen, can be supplied and continuously removed in any ratios.
- Volume flows of 500 Nml / min are usually set with a ratio of inert gas / N 2 O / benzene of 19 3 1. Gaseous samples are taken from this circuit injected directly into a gas chromatograph to analyze the composition of the reaction mixture.
- the reactor is used in this way as a continuously operated Ruhr kettle.
- the volume flow in the inner circuit is orders of magnitude higher than the continuously supplied amount of gas.
- the reaction You can choose any time, and constancy will appear after just a few hours
- the BET surface areas of the compounds produced are approximately 450 m 2 / g, the mean value of the pore size is 0.55 nm.
- the determination is carried out according to Horvath and
- the activity of the catalyst is determined by GC on the basis of the measured benzene conversion
- Component for silicon tetraalkyl orthosilicates e.g. tetraethyl orthosilicate
- Component for tetravalent subgroup metals metal tetrahalides, metal oxohalides, metal tetraalkoxy compounds, eg titanium tetraethylate, zirconium isopropylate
- Catalyst like 4 5 but produced with appropriate amounts of ammonium hexacyanoferrate (according to the invention)
- Catalyst not according to the invention made with iron acetylacetonate
- Catalyst not according to the invention produced with iron citrate. Analysis of the end product (% by weight) 1.6 TiO 2
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01988696A EP1334067A1 (de) | 2000-10-26 | 2001-10-12 | Verfahren zur herstellung von formselektiven katalysatoren und deren verwendung |
US10/399,781 US20040063568A1 (en) | 2000-10-26 | 2001-10-12 | Method for the production of form-selective catalysts and use thereof |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10053085.0 | 2000-10-26 | ||
DE10053085 | 2000-10-26 | ||
DE10139316.4 | 2001-08-09 | ||
DE10139316A DE10139316A1 (de) | 2000-10-26 | 2001-08-09 | Verfahren zur Herstellung von formselektiven Katalysatoren und deren Verwendung |
Publications (1)
Publication Number | Publication Date |
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WO2002034672A1 true WO2002034672A1 (de) | 2002-05-02 |
Family
ID=26007500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2001/011806 WO2002034672A1 (de) | 2000-10-26 | 2001-10-12 | Verfahren zur herstellung von formselektiven katalysatoren und deren verwendung |
Country Status (3)
Country | Link |
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US (1) | US20040063568A1 (de) |
EP (1) | EP1334067A1 (de) |
WO (1) | WO2002034672A1 (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2011053478A1 (en) * | 2009-10-26 | 2011-05-05 | Saudi Arabian Oil Company | Visible light-enhanced enzymatic promotion of hydrocarbon reactions |
US9630899B1 (en) * | 2015-10-26 | 2017-04-25 | Chang Chun Plastics Co. Ltd. | Process for producing hydroquinone and derivates |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1160419B (de) * | 1958-09-24 | 1964-01-02 | Union Carbide Corp | Verfahren zur Herstellung von metallbeladenen zeolithischen Molekularsieben |
EP0071136A2 (de) * | 1981-07-30 | 1983-02-09 | Bayer Ag | Zinkhaltige Aluminiumsilikat-Katalysatoren, Verfahren zu ihrer Herstellung und ihre Verwendung |
EP0198721A2 (de) * | 1985-04-17 | 1986-10-22 | CHEVRON U.S.A. Inc. | Verfahren zur Herstellung eines Zeolitischen Reformierkatalysators |
DE19829515A1 (de) * | 1998-07-02 | 2000-02-10 | Kowalak Stanislav | Metallmodifizierten Zeolith enthaltender Katalysator |
-
2001
- 2001-10-12 WO PCT/EP2001/011806 patent/WO2002034672A1/de not_active Application Discontinuation
- 2001-10-12 US US10/399,781 patent/US20040063568A1/en not_active Abandoned
- 2001-10-12 EP EP01988696A patent/EP1334067A1/de not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1160419B (de) * | 1958-09-24 | 1964-01-02 | Union Carbide Corp | Verfahren zur Herstellung von metallbeladenen zeolithischen Molekularsieben |
EP0071136A2 (de) * | 1981-07-30 | 1983-02-09 | Bayer Ag | Zinkhaltige Aluminiumsilikat-Katalysatoren, Verfahren zu ihrer Herstellung und ihre Verwendung |
EP0198721A2 (de) * | 1985-04-17 | 1986-10-22 | CHEVRON U.S.A. Inc. | Verfahren zur Herstellung eines Zeolitischen Reformierkatalysators |
DE19829515A1 (de) * | 1998-07-02 | 2000-02-10 | Kowalak Stanislav | Metallmodifizierten Zeolith enthaltender Katalysator |
Also Published As
Publication number | Publication date |
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US20040063568A1 (en) | 2004-04-01 |
EP1334067A1 (de) | 2003-08-13 |
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