WO2002094434A1 - Ni/tio2-hydrierkatalysator - Google Patents

Ni/tio2-hydrierkatalysator Download PDF

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Publication number
WO2002094434A1
WO2002094434A1 PCT/EP2002/005423 EP0205423W WO02094434A1 WO 2002094434 A1 WO2002094434 A1 WO 2002094434A1 EP 0205423 W EP0205423 W EP 0205423W WO 02094434 A1 WO02094434 A1 WO 02094434A1
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WO
WIPO (PCT)
Prior art keywords
catalyst
nickel
hydrogenation
tio
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.)
Ceased
Application number
PCT/EP2002/005423
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German (de)
English (en)
French (fr)
Inventor
Dominic Vanoppen
Ekkehard Schwab
Jörn Müller
Ulrich Penzel
Gunter Georgi
Bernd Weidner
Dietrich Tittelbach-Helmrich
Jürgen Dahlhaus
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BASF SE
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BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to US10/478,475 priority Critical patent/US7408086B2/en
Priority to KR1020037015078A priority patent/KR100874678B1/ko
Priority to EP02750940A priority patent/EP1397208B1/de
Priority to HU0400780A priority patent/HU229646B1/hu
Priority to JP2002591144A priority patent/JP4338400B2/ja
Priority to MXPA03010591A priority patent/MXPA03010591A/es
Priority to DE50206151T priority patent/DE50206151D1/de
Publication of WO2002094434A1 publication Critical patent/WO2002094434A1/de
Anticipated expiration legal-status Critical
Ceased 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
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
    • 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
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/063—Titanium; Oxides or hydroxides thereof
    • 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
    • B01J23/74—Iron group metals
    • B01J23/755—Nickel
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/391—Physical properties of the active metal ingredient
    • B01J35/393—Metal or metal oxide crystallite size
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • B01J35/45—Nanoparticles
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/70—Catalysts, in general, characterised by their form or physical properties characterised by their crystalline properties, e.g. semi-crystalline
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/70—Catalysts, in general, characterised by their form or physical properties characterised by their crystalline properties, e.g. semi-crystalline
    • B01J35/77—Compounds characterised by their crystallite size
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • 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
    • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
    • B01J2235/15—X-ray diffraction
    • 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
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth 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
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/83—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with rare earths or actinides

Definitions

  • the present invention relates to a hydrogenation catalyst which contains nickel on a TiO 2 support.
  • the catalyst is used in particular for the hydrogenation of nitroaromatic compounds to give corresponding aromatic amino compounds.
  • nickel-containing catalysts as hydrogenation catalysts has been known for a long time.
  • Russian Journal of Applied Chemistry, Vol. 70, No. 8, 1997, pages 1236 to 1253 the preparation of such nickel-containing catalysts is described in detail.
  • the catalysts described contain nickel primarily on silicon dioxide or aluminum oxide as a support. They can be produced by precipitation onto the support or by coprecipitation.
  • SiO 2 / TiO 2 supports are also used, it being stated that TiO 2 as a modifier can lead to mechanically stable catalysts.
  • DD-A-152 065 relates to a process for the hydrogenation of nitroaromatics with stirrable suspension catalysts.
  • the catalyst is prepared by precipitation of a nickel salt solution in the presence of silica gel with a certain particle size distribution.
  • DD-A-284 371 relates to a process for the reduction of nitroaromatics in the presence of a Ni / SiO 2 catalyst.
  • the catalyst is supported on a support with a size of more than 1 mm and passivated after activation. Before the reaction, the catalyst is ground in the reactor.
  • No. 3,868,332 relates to a hydrogenation catalyst which is used in particular for converting benzene into cyclohexane.
  • the catalyst is produced by co-precipitation of nickel and silicate ions in the presence of a porous silica carrier.
  • WO 95/14647 relates to a process for the oligomerization of olefins to highly linear oligomers.
  • An oxidic catalyst is used, the nickel oxide, Contains silicon dioxide and titanium dioxide and an alkali metal oxide.
  • the catalyst is prepared by co-precipitating a nickel salt solution with a sodium silicate solution onto finely divided titanium dioxide powder. Nickel is present in oxidic form and the catalyst is used as a fixed bed in the form of compressed tablets. The use as a hydrogenation catalyst is not described.
  • DE-A-199 09 176 and DE-A-199 09 168 relate to hydrogenation catalysts which contain nickel and often zirconium on a support containing zirconium.
  • the catalyst In the hydrogenation of nitroaromatic compounds to aromatic amino compounds, the catalyst is exposed to a strongly alkaline medium.
  • a catalyst dispersed in the reaction medium is subjected to high mechanical stress when the reaction mixture is circulated or when it is stirred. It should have a particle size distribution such that it is both readily dispersible and easy to separate under operating conditions.
  • the object of the present invention is to provide a catalyst for the hydrogenation of nitroaromatic compounds which shows the above range of properties and avoids the disadvantages of the known catalysts.
  • a catalyst comprising nickel on a TiO 2 support , obtainable by co-precipitation of nickel and at least one further metal, selected from Si, Zr, Hf, alkaline earth metals, Y, La, Ce and optionally at least a doping metal, selected from groups 5 to 1 1 of the Periodic Table of the Elements, from a solution containing corresponding metal salts, on a particulate TiO 2 support , then drying, calcining and reducing and optionally passivating to the nickel-containing catalyst.
  • Catalysts are obtained which are chemically stable both in a strongly alkaline medium and under heavy mechanical stress, for example by a Circulatory pumps are physically stable.
  • particulate catalysts are obtained which, under operating conditions, have both good dispersibility and good separability and allow good mass transfer.
  • the joint precipitation of nickel and a further carrier precursor also allows an advantageous particle size distribution of the catalyst and the formation of small nickel crystallites, which lead to a high activity of the catalyst.
  • the average particle size (d 50 ) of the catalyst is preferably at least 3 ⁇ m, particularly preferably at least 4 ⁇ m, in particular at least 5 ⁇ m. It is preferably at most 80 ⁇ m, particularly preferably at most 40 ⁇ m.
  • the nickel crystallite size is preferably at least 4 nm, particularly preferably at least 7 nm. It is preferably at most 20 nm, particularly preferably at most 15 nm. Ranges from 7 to 15 nm and in particular 10 to 12 nm are particularly preferred. These crystallite sizes allow a high activity of the catalyst, whereby the crystallites can still be passivated on the surface in order to make the catalyst manageable in air. With smaller particle sizes, the crystallites are more easily oxidized during passivation. Larger crystallite sizes decrease the activity of the catalyst for a given amount of nickel.
  • the proportion of nickel in the catalyst according to the invention is preferably 20 to 80% by weight, particularly preferably 40 to 70% by weight, in particular 50 to 65% by weight, based on the entire catalyst and based on nickel as metal.
  • the weight ratio of the oxide of the at least one further metal to the TiO 2 support is preferably (0.2 to 4): 1, particularly preferably (0.5 to 2): 1, in particular (0.8 to 1.2): 1 , Similar amounts of TiO 2 support and oxide of at least one other metal (other support precursors) are specifically used.
  • At least one doping metal is used, its amount, based on the oxide and the entire catalyst, is 0.1 to 10% by weight, particularly preferably 1 to 7% by weight.
  • the catalysts of the invention have a high mechanical stability, so that when they are used as a dispersed catalyst they experience a reduction in particle size in the course of use, but this remains in a range which allows the catalyst to be separated off with a settier. The separation via a settier simplifies the separation of the catalyst from the reaction mixture and the subsequent recycling of the catalyst.
  • the specific carrier combination gives the catalyst according to the invention the advantageous spectrum of properties.
  • the catalyst according to the invention can also be passivated in order to make it storable and easy to handle in the air.
  • reference can be made, for example, to DE-A-199 09 175.
  • the catalyst can be subjected to one or more shaping steps during production. For example, after the precipitation and drying, before or after the calcination, it is possible to bring the catalyst into a desired shape, to reduce it, to passivate it and then to convert it into catalyst particles of the desired particle size.
  • the precipitated catalyst precursor can be filtered off from the precipitation solution and dried, whereupon lumps from the filter cake are calcined, reduced, passivated and in turn ground.
  • Other possible shaping steps are tableting and extrusion.
  • the catalyst according to the invention is generally prepared by precipitation as follows:
  • TiO 2 powder (for example S 150 from Kemira) is reduced to a particle diameter ⁇
  • water glass is now added as the Si source.
  • the pH is adjusted to a value between 5 and 10
  • a solution of Ni nitrate and any additional salts such as Zr acetate, Ce nitrate, Mg nitrate are pumped in within 30 min and the pH is kept constant at a value between 5 and 10 by simultaneous pumping of a soda solution and optionally a water glass solution.
  • the mixture is then stirred for 30 minutes while blowing in air.
  • the pH is brought to a value of at least 7.5 with soda solution.
  • the precipitate is filtered off and washed until it is free of nitrates.
  • the filter cake is dried (12 h, 120 ° C) and then calcined (4 h, 400 ° C).
  • the product obtained in this way is comminuted to an average particle diameter of ⁇ 100 ⁇ m and reduced in a stream of hydrogen at 400 to 550 ° C. for 4 h.
  • the invention also relates to a process for the preparation of a catalyst as defined above, in which the process steps specified are carried out.
  • the invention also relates to the use of the catalyst for the hydrogenation of nitroaromatic compounds.
  • the invention also relates to a process for the preparation of aromatic amino compounds by hydrogenation of corresponding nitroaromatic compounds, the hydrogenation being carried out in the presence of a catalyst as defined above.
  • nitroaromatic compounds can be used.
  • the nitroaromatic compounds are preferably selected from nitrobenzene, nitrotoluene and dinitrotoluene.
  • Corresponding aromatic amino compounds to be produced are aniline, o-toluidine, p-toluidine and toluenediamine.
  • the hydrogenation according to the invention can be carried out continuously or batchwise in the liquid and gas phases. It is preferably carried out in the liquid phase.
  • the reaction can be carried out in the presence of a suitable solvent.
  • the hydrogenation is particularly preferably carried out in a dispersion of the catalyst.
  • the hydrogenation is preferably carried out at a temperature in the range from 60 to 200 ° C., particularly preferably 100 to 140 ° C. and a hydrogen pressure of 5 to 100 bar, particularly preferably 20 to 30 bar.
  • the catalysts prepared by the above method were examined by XRD to determine the nickel crystallite size.
  • the dso value was determined from the particle size distribution. This can be done, for example, in a Sympatec-Helos suspension cell, water with 1 g / 1 sodium pyrophosphate being used as the dispersant.
  • To determine the mechanical stability of the catalysts they were ground in the Ultraturrax for 1, 3 or 10 min. If reduction was carried out at different temperatures, the temperatures are given. The results are summarized in Table 1 below.
  • the components other than TiO 2 were each precipitated on TiO 2 .
  • the percentages relate to the oxide weight, for Ni to the metal weight
  • the catalysts were used to hydrogenate dinitrotoluene (DNT) to toluenediamine (TDA).
  • DNT dinitrotoluene
  • TDA toluenediamine
  • the procedure was as follows: A 300 ml autoclave was filled with 0.8 g of a freshly reduced catalyst, 100 ml of n-butanol, 20 g of DNT, pressed up to 25 bar with hydrogen and heated to 80.degree. The hydrogen uptake in 1 / min was taken as a measure of the activity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
PCT/EP2002/005423 2001-05-21 2002-05-16 Ni/tio2-hydrierkatalysator Ceased WO2002094434A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US10/478,475 US7408086B2 (en) 2001-05-21 2002-05-16 Ni/TiO2 hydrogenation catalyst
KR1020037015078A KR100874678B1 (ko) 2001-05-21 2002-05-16 Ｎｉ/ｔｉｏ2 수소화 촉매
EP02750940A EP1397208B1 (de) 2001-05-21 2002-05-16 Ni/tio2-hydrierkatalysator
HU0400780A HU229646B1 (en) 2001-05-21 2002-05-16 Ni/tio2 hydrogenation catalyst
JP2002591144A JP4338400B2 (ja) 2001-05-21 2002-05-16 Ｎｉ／ＴｉＯ２−水素化触媒
MXPA03010591A MXPA03010591A (es) 2001-05-21 2002-05-16 Catalizador de hidrogenacion ni/ti02.
DE50206151T DE50206151D1 (de) 2001-05-21 2002-05-16 Ni/tio2-hydrierkatalysator

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10124600A DE10124600A1 (de) 2001-05-21 2001-05-21 Ni/Ti02-Hydrierkatalysator
DE10124600.5 2001-05-21

Publications (1)

Publication Number Publication Date
WO2002094434A1 true WO2002094434A1 (de) 2002-11-28

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PCT/EP2002/005423 Ceased WO2002094434A1 (de) 2001-05-21 2002-05-16 Ni/tio2-hydrierkatalysator

Country Status (10)

Country Link
US (1) US7408086B2 (enExample)
EP (1) EP1397208B1 (enExample)
JP (1) JP4338400B2 (enExample)
KR (1) KR100874678B1 (enExample)
CN (1) CN1261209C (enExample)
AT (1) ATE320849T1 (enExample)
DE (2) DE10124600A1 (enExample)
HU (1) HU229646B1 (enExample)
MX (1) MXPA03010591A (enExample)
WO (1) WO2002094434A1 (enExample)

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CN102718666A (zh) * 2012-05-29 2012-10-10 吴江市屯村颜料厂 一种对甲苯胺的制备方法

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US20060025301A1 (en) * 2004-07-30 2006-02-02 Reddy Benjaram M Process for preparing nanosized, thermally stable, and high surface area multi-component metal oxides
CN100441293C (zh) * 2005-09-26 2008-12-10 天津大学 氯代硝基苯加氢合成氯代苯胺负载型镍催化剂及制备方法
JP4724860B2 (ja) * 2005-10-19 2011-07-13 国立大学法人 大分大学 水素製造用触媒の製造方法
US8067332B2 (en) * 2006-05-03 2011-11-29 Samsung Sdi Co., Ltd. Methanation catalyst, and carbon monoxide removing system, fuel processor, and fuel cell including the same
KR101000684B1 (ko) * 2007-10-11 2010-12-10 세종대학교산학협력단 이산화티타늄 나노튜브분말 및 이를 이용한 고압수소저장탱크 삽입용 판형 필름의 제조방법
EP2203250B1 (en) * 2007-10-19 2015-04-08 Shell Internationale Research Maatschappij B.V. Catalyst for the hydrogenation of unsaturated hydrocarbons and process for its preparation
PT2429983T (pt) 2009-05-14 2017-11-08 Basf Se Método para a produção de anilina
CN103480380B (zh) * 2013-09-03 2015-04-22 万华化学集团股份有限公司 一种用于固定床苯胺精馏残渣资源化利用的催化剂及其制备方法
CN104130194B (zh) * 2014-08-12 2016-08-31 南通醋酸化工股份有限公司 一种5-氨基苯并咪唑酮的合成方法
JP6824168B2 (ja) * 2014-12-19 2021-02-03 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイＳｈｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌｅ Ｒｅｓｅａｒｃｈ Ｍａａｔｓｃｈａｐｐｉｊ Ｂｅｓｌｏｔｅｎ Ｖｅｎｎｏｏｔｓｈａｐ 触媒の調製方法
CN109803949B (zh) * 2016-10-10 2023-04-14 巴斯夫欧洲公司 在硝基化合物的连续液相氢化中使用碱金属离子、碱土金属离子或稀土金属离子进行催化剂改性
CN106902835B (zh) * 2017-02-27 2019-07-09 浙江林江化工股份有限公司 一种铈改性负载型镍基催化剂及其制备方法和应用
JP7088690B2 (ja) * 2017-02-28 2022-06-21 東ソー株式会社 芳香族化合物の製造方法
CN111960948B (zh) * 2020-09-16 2022-07-26 肯特催化材料股份有限公司 一种四丁基溴化铵的合成工艺
CN116832871B (zh) * 2022-03-23 2025-08-29 万华化学集团股份有限公司 一种纳米Ni催化剂的制备方法及其应用

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EP1397208B1 (de) 2006-03-22
HU229646B1 (en) 2014-03-28
DE10124600A1 (de) 2002-11-28
KR20040000481A (ko) 2004-01-03
EP1397208A1 (de) 2004-03-17
HUP0400780A2 (hu) 2004-07-28
MXPA03010591A (es) 2004-03-09
US20040147783A1 (en) 2004-07-29
ATE320849T1 (de) 2006-04-15
JP4338400B2 (ja) 2009-10-07
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HUP0400780A3 (en) 2012-05-29
US7408086B2 (en) 2008-08-05

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