EP1383601A2 - Procede d'hydrogenation de composes carbonyles - Google Patents

Procede d'hydrogenation de composes carbonyles

Info

Publication number
EP1383601A2
EP1383601A2 EP02764063A EP02764063A EP1383601A2 EP 1383601 A2 EP1383601 A2 EP 1383601A2 EP 02764063 A EP02764063 A EP 02764063A EP 02764063 A EP02764063 A EP 02764063A EP 1383601 A2 EP1383601 A2 EP 1383601A2
Authority
EP
European Patent Office
Prior art keywords
catalyst
copper
mixture
height
diameter
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Withdrawn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
EP02764063A
Other languages
German (de)
English (en)
Inventor
Michael Koch
Steffen Maas
Wolfgang Jürgen PÖPEL
Matthias Dernbach
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1383601A2 publication Critical patent/EP1383601A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • 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
    • B01J23/72—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
    • 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
    • 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
    • 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
    • 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
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • 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
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product 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
    • 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

Definitions

  • the invention relates to a process for the catalytic hydrogenation of carbonyl compounds in the presence of copper-containing catalyst tablets and the copper-containing catalyst tablets per se.
  • No. 3,923,694 describes, for example, a catalyst of the copper oxide / zinc oxide / aluminum oxide type.
  • the disadvantage of this catalyst is that it is not mechanically stable enough during the reaction and therefore disintegrates relatively quickly. This results in a loss of activity and a build-up of differential pressure across the reactor due to the disintegrating shaped catalyst bodies. As a result, the system must be shut down prematurely.
  • DE-A 195 05 347 describes very generally a process for the production of catalyst tablets with high mechanical strength, a metal powder or a powder of a metal alloy being added to the material to be tabletted.
  • aluminum powder or copper powder is added as the metal powder.
  • a shaped body is obtained with a copper oxide / zinc oxide / aluminum oxide catalyst, however, which has a poorer side compressive strength than a shaped body which was produced without the addition of aluminum powder, and the shaped body according to the invention showed one when used as a catalyst poorer conversion activity than catalysts that were produced without the addition of aluminum powder.
  • a hydrogenation catalyst made of NiO, Zr0, Mo0 3 and CuO, which was mixed with Cu powder during the production. about selectivity or 'the activity, however, no details were provided in this document.
  • DE 198 09 418 describes a process for the catalytic hydrogenation of a carbonyl compound in the presence of a catalyst which comprises a support which primarily contains titanium dioxide and, as the active component, copper or a mixture of copper and at least one of the metals selected from the group zinc , Aluminum, cerium, a noble metal and, a metal of the VIII. Subgroup, comprises, the ' copper surface a maximum of 10 m2 / g
  • Preferred carrier materials are mixtures of titanium dioxide with aluminum oxide or zirconium oxide or aluminum oxide and zirconium oxide.
  • the catalyst material is deformed with the addition of metallic copper powder.
  • the invention was therefore based on the object to provide a process for the catalytic hydrogenation of carbonyl compounds .. _ len formatzustel-, wherein a catalyst is used, the technical * ⁇ ice ".e he ⁇ rzu1s, tCeZl" len in a simple W i ', ..a .a_u • s "rich- * .nd h -oh.e m'ec'han.isc j.h'e
  • Powder which includes the carrier material, * the ⁇ active component and, in addition to a conventional tabletting aid such as graphite, additional metallic Cu powder, to catalyst tablets with a diameter d and / or a height h less than 3 mm to high activities and selectivities as well as leads to good stability of the catalyst.
  • a conventional tabletting aid such as graphite, additional metallic Cu powder
  • the object was achieved by a process for the catalytic hydrogenation of a carbonyl compound or a mixture of two or more carbonyl compounds in the presence of catalyst tablets which contain an inorganic carrier containing TiO 2, copper as an active component or a mixture of copper with at least one of the Metals selected from the group zinc, aluminum, cerium, a noble metal and a metal of subgroup VIII, and whose copper surface is at most 10 m 2 / g, characterized in that the diameter d and / or the height h of the tablet is smaller Is 3 mm.
  • the catalyst used in the process according to the invention is characterized in that the active component copper is applied to the support material used, with respect to the method of application no ⁇ restrictions exist. 5 In particular, the following application methods can be considered:
  • the carrier is dried and
  • the impregnation can be carried out according to the so-called "incipient wetness” method, in which the carrier is moistened with the drinking solution to a maximum of saturation 15 in accordance with its water absorption capacity.
  • the impregnation can also take place in the supernatant solution.
  • the inorganic carrier material is used in the " impregnation as a preformed mass, for example as a powder, balls, strands or “tablets. Use as a powder is particularly preferred.
  • a copper salt solution preferably mij: Spda solution
  • An aqueous suspension of the carrier material is used as a template.
  • the precipitation catalyst can be produced in a two-stage process.
  • a "powder in accordance with the arrival spent" is a ⁇ manufactured un-dried.
  • This powder 45 is transferred into an aqueous suspension and as a template equivalent to . ' . used in the embodiment (i).
  • Precipitated precipitation resulting from., A) or b),. 5 are filtered in a conventional manner and preferably washed free of alkali.
  • Another additive is . ,for the production; of; .Katalysators, .. slegi1ich to-the above-described powder and "to graphite ,. , metallic Cu powder added-J.
  • .Katalysators, .. slegi1ich to-the above-described powder
  • graphite to-the above-described powder
  • metallic Cu powder added-J are preferred, based on that
  • the catalyst tablets can be symmetrical, that means height h and diameter “d, S ⁇ ind the same, or asymmetrical, that means height h and ⁇ purchmes.ser.d, different. Values, whereby d and / or -h ⁇ but less than ..3 mm ,. are.
  • the ratio d: h can be a maximum of 1: 2, 0 that means the maximum ⁇ value for the tablet height ⁇ corresponds to this. double the diameter of the tablet.
  • the lateral compressive strength was determined in the context of the present application using a device of the "Z 2.5 / T 919" type from Zwick (Ulm), the abrasion according to ASTM Designation D 4058-81. The measurements were carried out under a nitrogen atmosphere in order to avoid re-oxidation of the catalysts.
  • the smoothed catalyst is activated either before or after installation in the reactor.
  • the catalyst is installed in the reactor and the hydrogenation solution is fed directly under hydrogen pressure.
  • the catalyst is charged with reducing gases, for example hydrogen, preferably hydrogen / inert gas mixtures, in particular hydrogen / nitrogen mixtures, at temperatures of 100 to 300, preferably 150 to 250, in particular 180, before charging the hydrogenation solution. pre-reduced to 240 ° C.
  • reducing gases for example hydrogen, preferably hydrogen / inert gas mixtures, in particular hydrogen / nitrogen mixtures, at temperatures of 100 to 300, preferably 150 to 250, in particular 180, before charging the hydrogenation solution. pre-reduced to 240 ° C.
  • a characteristic size of the catalysts according to the invention is their specific copper surface. It is calculated from the N 2 0 consumption determined by oxidation of surface copper atoms with gaseous N0 in a heated sample of the catalyst.
  • the sample is first treated for 10 minutes with 10 mbar hydrogen at a temperature of 240 ° C. Then the
  • the sample In a second stage, the sample with N 2 0 at a temperature of 70 ° C at a pressure . of 266 mbar for 2 hours ⁇ , with decomposition of the N0 being observed on the sample.
  • the sample is then evacuated to less than 10 -3 mbar and then the increase in the mass of the catalyst due to the formation of copper oxide on the surface thereof is determined.
  • the present 'invention also relates to catalytic converters 5 tortablette, the carrier containing an inorganic, Ti0, as active component -copper * or- one; mixture of copper with at least - - least one of the / .Metalle * nowadays know herein. ". aluminum, cerium ,, - r a noble metal: .ünd" from -Der- group * zinc, • a metal of the VIII * .- ⁇ ⁇ - * ⁇ *.
  • Subgroup and includes 'the copper surface up to 10 m / g is 0, characterized in that the diameter d and / or the height h of the tablets * less than' is 3 mm.
  • the preferred area of use for the catalyst tablets produced according to the invention is hydrogenation in a fixed bed.
  • the embodiment as a fluidized bed reaction with catalyst material in a swirling and swirling motion is also possible.
  • the hydrogenation can be carried out in the gas phase or in the liquid phase.
  • the process according to the invention is suitable for the hydrogenation of carbonyl compounds such as, for example, aldehydes and ketones to give the corresponding alcohols, * aliphatic and: cycloaliphatic saturated and unsaturated carbonyl compounds being preferred. 5 With aromatic carbonyl compounds, it can ⁇ desired by-products come by hydrogenation of the aromatic nucleus.
  • CarbonyLyeritatien - can - other • functional.e.; - groups such as hydroxy .; or * wear A inog groups; Unsaturated ;: Carbonyl compounds iW ß rcteri in the .Rege "-to the corresponding- 0 saturated -Alcohol " : hydrie " rt :. * The term ⁇ " Carbonyl-
  • Enalization products such as 2-ethylhexenal, 2-methylpentenal, 2, 4-diethylqctenal or 2,4-dimethyl-heptenal are particularly preferred.
  • Preferred hydroxy aldehydes * are C 3 -C 2 -hydroxy aldehydes, such as by. Ald oil reaction from aliphatic and cycloaliphatic aldehydes and ketones with * themselves or F r - aldehyde are accessible. "Examples are 3-hydroxypropanal . ' , ' Dimethylolethanal, Trimethylöletharial (Pefitaerythr ' itäl) 3-Hyctroxybu-
  • ketones are acetone, butarion, 2-pentanone, 3-pentanone,
  • Carboxylic acid esters such as.
  • the C ⁇ -C ⁇ o-alkyl esters of the above-mentioned carboxylic acids especially methyl formate, ethyl acetate, butyl butylate, dimethyl terephthalate, dimethyl adipate, dimethyl maleate, (methyl) acrylic acid methyl
  • Carboxylic anhydrides e.g. the anhydrides of the 5 carboxylic acids mentioned above, in particular acetic anhydride, propionic anhydride, benzopic anhydride and maleic anhydride;
  • the process according to the invention is particularly preferably used for the hydrogenation of aldehydes and hydroxyaldehydes.
  • the carbonyl compound to be hydrogenated can the hydrogenation reactor _ are fed alone or as a mixture with the product of ⁇ , hydrogenation reaction 0, i -where • be -i ⁇ , - d> ies in unve -rd_ün-nt> he Fo. Rm '. or he under
  • additional solvent can happen.
  • Suitable additional solvents in particular water, alcohols such as 'methanol, ethanol and the alcohol, "produced under' the Christsbeding ⁇ ngen.
  • Preferred solvents are water, THF, NMP and ether, such as, for example, dimethyl, diethyl ether, MTBE, and water is particularly preferred.
  • the hydrogenation both in the bottom and in the downflow mode, in each case preferably carried out in the cycle mode, 0 is generally carried out at a temperature of 50 to 250 ° C., preferably at 70 to 20 ° C., particularly preferably at 100 to 140 ° C. and a pressure of 15, up to 250 t bar, preferably ⁇ 20 to 200, particularly preferably - 2P5 '*, b ** is> -1-00 bar through.
  • a catalyst was carried * precipitation.
  • a suspension of Ti0 2 was used in water.
  • the precipitated material formed during the precipitation was filtered, washed and dried at 120 ° C.
  • the dried powder was for two hours at 200 ° C calcined and data. t. to below, addition of 3 wt .-% of graphite, and 20 wt .-% metallic 0 Kupferpulverzu tablets -mi 3 mm 'diameter' -'und 3 MITIM * height ' ⁇ " ⁇ '" ve press ⁇ " These ⁇ tablets; would be -2 hours; egg; : Calcined at 450 ° C.
  • the finished catalyst ⁇ contained 60% . CüO . _and 40 ;;% Ti0 2 ; ⁇ at ⁇ a vibrating weight of * ; 1498 pounds g / ⁇ ; a; Hg-P ⁇ re ⁇ yol ⁇ en from; 0.21 r ml / g,: *. a surface according to * BET " of 23/6 m ?; g-, - a copper surface 5 of 1.7 m2 g, a ' ' lateral compressive strength of -54, 5 N. ' ⁇ "' • '
  • DMB dimethylol butanal
  • TMP trimethylol propane
  • a mixture of 30% DMB and * 70% water was used as the starting solution.
  • This mixture was heated in a reactor of the volume 210 ml (130 ml Haupreaktor and 80 ml after-reactor) in J circulation mode at a flow of 7.5 1 / h and a temperature of 120 ° C 0 (primary reactor) or 130 ° C "( postreactor) hydrogenated using the * ' ⁇ catalysts A and B at 90 bar, wherein the catalyst loading "was between 0.2 kg DMB / (l cat -h) and 2 kg of DMB / (l cat -h).

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

Abstract

L'invention concerne un procédé d'hydrogénation catalytique d'un composé carbonylé ou d'un mélange d'au moins deux composés carbonylés en présence de pastilles catalytiques qui comprennent un support inorganique contenant du TiO2 et, comme composant actif, du cuivre ou un mélange de cuivre et d'au moins un métal, choisi dans le groupe comprenant le zinc, l'aluminium, le cérium, un métal noble et un métal du sous-groupe VIII, et dont la surface de cuivre est égale au maximum à 10 m<2>/g, ces pastilles se caractérisant par un diamètre d et/ou une hauteur h inférieurs à 3 mm.
EP02764063A 2001-04-21 2002-04-17 Procede d'hydrogenation de composes carbonyles Withdrawn EP1383601A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10119719 2001-04-21
DE10119719A DE10119719A1 (de) 2001-04-21 2001-04-21 Verfahren zur Hydrierung von Carbonylverbindungen
PCT/EP2002/004250 WO2002085825A2 (fr) 2001-04-21 2002-04-17 Procede d'hydrogenation de composes carbonyles

Publications (1)

Publication Number Publication Date
EP1383601A2 true EP1383601A2 (fr) 2004-01-28

Family

ID=7682322

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02764063A Withdrawn EP1383601A2 (fr) 2001-04-21 2002-04-17 Procede d'hydrogenation de composes carbonyles

Country Status (11)

Country Link
US (1) US6787677B2 (fr)
EP (1) EP1383601A2 (fr)
JP (1) JP2004525981A (fr)
KR (1) KR100839292B1 (fr)
CN (1) CN1260192C (fr)
AU (1) AU2002338398A1 (fr)
BR (1) BR0208908A (fr)
DE (1) DE10119719A1 (fr)
MX (1) MXPA03008674A (fr)
MY (1) MY128614A (fr)
WO (1) WO2002085825A2 (fr)

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DE10313702A1 (de) * 2003-03-27 2004-10-07 Basf Ag Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen
DE10357715A1 (de) * 2003-12-09 2005-07-14 Basf Ag Verfahren zur Herstellung von definierten Gemischen aus THF, BDO und GBL durch Gasphasenhydierung
DE102004033556A1 (de) * 2004-07-09 2006-02-16 Basf Ag Katalysatorformkörper und Verfahren zur Hydrierung von Carbonylverbindungen
US7388116B2 (en) * 2006-06-06 2008-06-17 Basf Aktiengesellschaft Hydrogenation of methylolalkanals
CN102159311B (zh) 2008-09-19 2013-07-10 巴斯夫欧洲公司 使用铝-铜催化剂连续制备胺的方法
TWI564072B (zh) * 2011-11-09 2017-01-01 China Petrochemical Technology Co Ltd Hydrogenation catalyst and preparation method thereof
US9040757B2 (en) 2013-03-08 2015-05-26 Pioneer Energy Synthesis of high caloric fuels and chemicals
US9080119B2 (en) 2011-11-10 2015-07-14 Pioneer Energy Synthesis of high caloric fuels and chemicals including pentanol from coal, natural gas, and biomass
CN104245653B (zh) 2011-11-10 2017-08-25 先趋能量公司 高热燃料和化学品的合成
DE102012019123B4 (de) * 2012-09-28 2021-10-21 Clariant International Ltd. Hydrierkatalysator und Verfahren zu dessen Herstellung durch die Verwendung von unkalziniertem Ausgangsmaterial
RU2609264C1 (ru) 2015-12-09 2017-01-31 Акционерное Общество "Газпромнефть - Московский Нпз" (Ао "Газпромнефть - Мнпз") Способ получения высокооктановых компонентов из олефинов каталитического крекинга
KR102245932B1 (ko) * 2017-10-23 2021-04-28 주식회사 엘지화학 트리메틸올프로판의 제조방법
KR102238560B1 (ko) * 2017-12-29 2021-04-08 한화솔루션 주식회사 고선택 전환이 가능한 탄소 기반의 귀금속-전이금속 촉매 및 이의 제조방법
CN112138670B (zh) * 2020-10-15 2023-12-08 中国石油大学(华东) 一种含铜锌铝的催化剂及其制备方法和用途
KR102477904B1 (ko) * 2020-10-27 2022-12-15 금호석유화학 주식회사 촉매 성형체, 그 제조방법 및 이를 이용한 환형 케톤의 제조방법

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DE19505347B4 (de) 1994-03-02 2008-10-02 Basf Se Verfahren zur Herstellung von Katalysator-Tabletten mit hoher mechanischer Festigkeit
DE19809418A1 (de) * 1998-03-05 1999-09-09 Basf Ag Verfahren zur Hydrierung von Carbonylverbindungen
DE19859776B4 (de) 1998-12-23 2008-06-19 Basf Se Verfahren zur Herstellung von Aminen
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Also Published As

Publication number Publication date
MXPA03008674A (es) 2003-12-12
KR20030093323A (ko) 2003-12-06
WO2002085825A3 (fr) 2003-02-20
KR100839292B1 (ko) 2008-06-17
JP2004525981A (ja) 2004-08-26
CN1525886A (zh) 2004-09-01
CN1260192C (zh) 2006-06-21
MY128614A (en) 2007-02-28
BR0208908A (pt) 2004-04-20
US6787677B2 (en) 2004-09-07
US20040082821A1 (en) 2004-04-29
WO2002085825A2 (fr) 2002-10-31
AU2002338398A1 (en) 2002-11-05
DE10119719A1 (de) 2002-10-24

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