EP1440051A1 - Procede pour la production de 6-methylheptan-2-one et utilisation de cette derniere - Google Patents

Procede pour la production de 6-methylheptan-2-one et utilisation de cette derniere

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Publication number
EP1440051A1
EP1440051A1 EP02777243A EP02777243A EP1440051A1 EP 1440051 A1 EP1440051 A1 EP 1440051A1 EP 02777243 A EP02777243 A EP 02777243A EP 02777243 A EP02777243 A EP 02777243A EP 1440051 A1 EP1440051 A1 EP 1440051A1
Authority
EP
European Patent Office
Prior art keywords
carried out
catalyst
hydrogenation
methylbutanal
methyl
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Withdrawn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
EP02777243A
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German (de)
English (en)
Inventor
Klaus-Diether Wiese
Guido Protzmann
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.)
Evonik Operations GmbH
Original Assignee
Oxeno Olefinchemie GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Oxeno Olefinchemie GmbH filed Critical Oxeno Olefinchemie GmbH
Publication of EP1440051A1 publication Critical patent/EP1440051A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds

Definitions

  • the present invention relates to a three-stage process for the preparation of 6-methylheptan-2-one from isobutene and the use of the product thus produced.
  • 6-methylheptanone is an intermediate for the production of isophytol, a building block for the synthesis of vitamin E. It is also the starting material for the synthesis of tetrahydrolinalool, dihydrogeraniol and other flavorings.
  • the title compound can also be obtained by hydrogenating 6-methyl-5-hepten-2-one or 6-methyl-3,5-heptadien-2-one over nickel or other catalysts (Izv. Akad. Nauk SSSR, Ser. Khim (5) (1972) 1052). Since the two starting materials are expensive, the target product cannot be produced economically in this way.
  • EP 0 816 321 A discloses a two-stage process for the preparation of 6-methylhepten-2-one.
  • 3-methylbutanal is aldol condensed with acetone.
  • the raw product is hydrogenated to the target product.
  • the aldol condensation is carried out batchwise in an autoclave at a pressure of 1.9 bar and a temperature of 72 ° C.
  • Acetone is introduced and 3-methylbutanal and 2% sodium hydroxide solution are added dropwise over 175 minutes.
  • the organic phase is separated off. This is hydrogenated for 7 hours at 120 ° C. and a pressure of 5 to 9 bar on 5% Pd / activated carbon.
  • the hydrogenation discharge is after filtering off the catalyst worked up by distillation.
  • the yield of the target product over both stages is 62% based on 3-methylbutanal.
  • This method has the disadvantages that both stages are carried out discontinuously, with a relatively long cycle time, which in turn results in low space-time yields.
  • EP 0 765 853 describes a further two-stage process for the preparation of 2-methylheptan- 2-one.
  • 3-methylbutanal is reacted with acetone to 4-hydroxy-6-methylheptan-2-one and in a lower yield to 6-methyl-3-hepten-2-one. This is done to increase the selectivity by reacting the aldehyde with acetone in a molar ratio of 1: 3 to 1:10 with a base in a molar ratio to the to aldehyde of 0.1 to 20%.
  • the low base addition is said to increase the selectivity, i. H. avoid the self-condensation of the aldehyde or acetone.
  • the disadvantage of this reaction procedure is that the space-time yield is too low for an industrial process.
  • this mixture is hydrogenated with simultaneous elimination of water.
  • aqueous alkali or alkaline earth lyes are used as catalysts.
  • precipitated acetate is filtered off and the two intermediates are obtained by distillation.
  • the distillate is hydrogenated in the presence of an acid (p-toluenesulfonic acid) at 100 ° C. and a pressure of 8 bar on a contact made of 5% Pd / activated carbon.
  • the catalyst is filtered off from the hydrogenation discharge, the organic phase is separated off and the target product is separated off therefrom by distillation.
  • the yield of 6-methylheptan-2-one is 65% over both stages, based on 3-methylbutanal.
  • This process has several disadvantages: the base used in the first stage is neutralized with acetic acid. As a result, the process is burdened by additional material costs. The resulting acetates have to be disposed of, which entails additional costs.
  • the present invention therefore relates to a process for the preparation of 6-methyl-heptan-2-one characterized by a) hydroformylation of isobutene to 3-methylbutanal b) base-catalyzed aldol condensation of 3-methylbutane with acetone to 6-methylhept-3- en-2-one, the molar ratio of 3-methylbutanal to the base used being more than 1: 0.3 and c) hydrogenation of 6-methylhept-3-en-2-one to 6-methyl-heptan-2-one ,
  • the 6-methyl-heptan-2-one produced according to the invention can be used to prepare isophytol, tetrahydrolinalool or dihydrogeraniol.
  • the isobutene used as the starting material for the production of 6-methylheptan-2-one by the process according to the invention can come from many sources.
  • Isobutene can be used as a pure substance or as an isobutene-containing mixture of substances, e.g. B. with other C 4 hydrocarbons.
  • Technical mixtures containing isobutene are the C section of an FCC, the C 4 section of a steam cracker, raffinate I, obtained from the C section of a steam cracker by butadiene extraction, or a hydrogenated C 4 section of a steam cracker, where most of the butadiene has been selectively hydrogenated to linear butenes.
  • Other isobutene-containing streams are mixtures which have been obtained by dehydrogenating hydrocarbon streams containing isobutane.
  • isobutene-rich streams are generated by the isomerization of C 4 streams with linear butenes.
  • isobutene is obtained from a C 4 cut after two reprocessing processes.
  • the first step that the two processing variants have in common is the removal of most of the butadiene. If butadiene can be marketed well or if it is self-consumed, it is separated by extraction or extractive distillation. In other cases, it is selectively hydrogenated to linear butenes up to a residual concentration of approximately 2000 ppm. What remains in both cases is a hydrocarbon mixture (raffinate I or hydrogenated crack C 4 ) which, in addition to the saturated hydrocarbons, contains n-butane and isobutane, the olefins, isobutene, 1-butene and 2-butenes.
  • Isobutene is separated from this hydrocarbon mixture by reaction with methanol to give Memyl-tert.-butyleth.er (MTBE).
  • MTBE Memyl-tert.-butyleth.er
  • the cleavage of MTBE provides a mixture of methanol and isobutene, which can be easily separated into the two components.
  • isobutene can be obtained after reaction with water via the intermediate tert-butanol and its cleavage.
  • an almost butadiene-free C 4 cut (C 4 stream from FCC, raffinate I or hydrogenated crack C) can be hydroisomerized in a reactive column.
  • a top product can be obtained which consists of isobutane and isobutene.
  • the hydroformylation of isobutene with synthesis gas to 3-methylbutanal is known.
  • Cobalt or rhodium catalysts can be used. In cobalt catalysis (DE 39 02 892 AI) the yield is up to 74%.
  • 2,2-dimethylpropanal and isobutane are formed.
  • Favorable yields are achieved in the hydroformylation with rhodium catalysts in the presence of organic phosphite ligands.
  • the hydroformylation of isobutene to 3-methylbutanal using a catalyst system consisting of rhodium and a bisphosphite is e.g. For example, in US 4,668,651, US 4,769,498 and WO 85-03702. No.
  • 4,467,116 describes, inter alia, the terminal hydroformylation of ⁇ -olefins dialkylated in the 2-position.
  • Catalyst systems consist of Rhodium and a triarylphosphine exist, at least one aryl radical in the ortho position carrying a bulky substituent.
  • a catalyst system which consists of rhodium and a phosphite of the general structure I.
  • Ar 15 Ar 2 and Ar 3 are aromatic radicals which can be substituted or unsubstituted, in each case the same or different.
  • Suitable aromatic radicals are, for example, the phenyl, the naphthyl, phenanthryl or the anthracyl radical. At least one of the aromatic radicals bears a group R i in the ortho position to the phosphite oxygen and a further substituent X i in the m or p position.
  • Ri can in turn be aliphatic, cycloaliphatic, aromatic or heterocyclic. Purely aliphatic residues have the general structure II.
  • Ra, Rb and Rc can be the same or different and denote hydrocarbon radicals with 1 to 6 carbon atoms.
  • Ri is preferably a phenyl or tert-butyl group.
  • Xi is a hydrocarbon or ether residue with 1 to 6 carbon atoms each.
  • the hydroformylation of isobutene or a hydrocarbon mixture which contains isobutene as the only unsaturated compound, according to step a), is preferably carried out using the catalyst system described above, consisting of rhodium and a triaryl phosphite, carried out in a homogeneous reaction (a liquid phase).
  • the reaction here takes place in a temperature range from 60 ° C. to 180 ° C., preferably in the range from 90 ° C. to 150 ° C.
  • the reaction pressure is between 10 bar and 200 bar, preferably between 20 bar and 100 bar.
  • a mixture of carbon monoxide and hydrogen in a molar ratio of 1/10 to 10/1 is used as the hydroformylation agent.
  • the rhodium concentration is 5 to 500 ppm by weight, preferably 10 to 200 ppm by weight. 1 to 50 moles of triaryl phosphite, preferably 5 to 30 moles, are used per mole of rhodium.
  • the reaction can be carried out batchwise, but a continuous procedure is advantageous.
  • the reaction product is expediently separated by distillation into unreacted isobutene, 3-methylbutanal, high boilers which contain the catalyst, and by-products. Unreacted isobutene and the catalyst are returned to the hydroformylation reactor.
  • step b Aldol condensation
  • the aldol condensation of 3-methylbutanal with acetone to 6-methylhept-3-en-2-one is preferably carried out as a two-phase reaction.
  • the reaction in step b) can be carried out continuously or batchwise, in a tubular reactor, flow tube or in a stirred tank.
  • the aldol condensation is base-catalyzed, preferred bases are inorganic, aqueous systems with a base concentration of 0.1 to 15% by weight. Common bases are alkali solutions such as NaOH, KOH, K 2 O, Na 2 O or NaHCO 3 , Na 2 CO 3 , K 2 CO 3 , acetates, formates or triethylamine.
  • Aldol condensation not only produces the desired product 6-methylhept-3-en-2-one, but also the by-products 4-methyl-3-penten-2-one (4-MP), 3-methyl-2-isopropyl- 2-butenal (3-MiPB), 5-methyl-2-isopropyl-2-hexenal (5-MiPH), 4-hydroxy-6-methylheptan-2-one (6-HMH).
  • the connections are subject to e.g. B. also an enol tautomerism, where all tautomeric forms of 6-methylhept-3-en-2-one are to be understood as a product of value.
  • step b) is carried out by dispersing an organic phase containing methyl butanal in a continuous phase containing the catalyst.
  • the reaction can be carried out in a tubular reactor, the catalyst in the continuous phase and the starting material in an organic, disperse phase is included and the loading factor B of the reactor is equal to or greater than 0.8 and the mass ratio between the continuous and disperse phase is greater than 2.
  • aqueous solutions of hydroxides are preferred as catalyst phases
  • Hydrogen carbonates, carbonates or carboxylates are used in the form of their alkali or alkaline earth compounds, in particular sodium and potassium hydroxide solutions.
  • the concentration of the catalyst in the catalyst solution is between 0.1 and 15% by mass, in particular between 0.1 and 5% by mass.
  • 3-methylbutanal, acetone and optionally a solvent are expediently fed into the catalyst phase in front of the respective reactor.
  • the molar ratio between 3-methylbutanal and acetone is 5/1 to 1/10, preferably 1/1 to 1/5.
  • the reaction takes place in a temperature range from 40 ° C. to 150 ° C., preferably in the range from 50 ° C. to 120 ° C.
  • the reaction time is between 0.1 and 20 minutes, preferably between 0.2 and 5 minutes.
  • the catalyst phase is separated from the reaction discharge and returned to the reactor. Unreacted feedstocks, some product, water and optionally solvent are preferably distilled off before the phase separation.
  • the distillate separates Condensation in an aqueous and organic phase, which can be returned to the reactor. After separation of the educts, in particular acetone, by distillation, the aqueous phase is preferably discarded in part to remove the water of reaction and partly returned to the process after optional use as washing liquid.
  • the product phase separated from the catalyst can optionally be worked up by distillation to pure 2-methylhept-3-en-2-one after a water wash. Another possibility is to use the crude product separated from the catalyst in the next stage. This procedure makes it possible to produce the desired ⁇ , ⁇ -unsaturated ketone in a selectivity of 95% based on 3-methylbutanal.
  • step b) it is possible to use a solvent.
  • the use of a solvent often results in an increase in the selectivity of the aldol condensation, control of the water discharge from the catalyst solution and simplification of the water separation from the aldol condensate.
  • a solvent is preferably used in which 3-methylbutanal, acetone and 6-methylhept-3-enone are soluble, the base or the continuous phase being insoluble in the solvent.
  • Such a solvent should have the following properties: It dissolves products and starting materials and is hardly soluble even in the catalyst phase. It is inert in the aldol condensation and optionally in the hydrogenation. It can be separated from the target products 6-methylhept-3-en-2-one and / or 6-methylheptan-2-one by distillation.
  • Suitable solvents are, for example, ethers or hydrocarbons such as toluene or cyclohexane.
  • solvents are preferred which form a minimum heterotrope with water, so that the separation of the water from the aldol condensate is particularly simple. Therefore, cyclohexane or toluene are preferred solvents.
  • step c The 6-methylhept-3-en-2-one obtained by crossed aldol condensation is selectively converted into 6-methylheptane in pure form or as a mixture which can contain acetone, 3-methylbutanal, water, solvents and high boilers. 2-one hydrogenated. This is preferably done on fixed bed Catalysts and / or acidic catalysts. Acid catalysts often contain acidic carrier material or carrier material soaked in acidic substances.
  • catalysts which can contain palladium, platinum, rhodium and / or nickel as the hydrogenation-active component.
  • the metals can be used in pure form, as compounds with oxygen or as alloys.
  • Preferred catalysts are those in which the hydrogenation-active metal is applied to a support.
  • Suitable carrier materials are aluminum oxide, magnesium oxide, silicon oxide, titanium dioxide and their mixed oxides and activated carbon. Of these catalysts, particularly preferred catalysts are palladium on activated carbon and palladium on aluminum oxide.
  • the palladium content is 0.1 to 5% by mass, preferably 0.2 to 1% by mass.
  • the hydrogenation can be carried out continuously or batchwise and both in the gas phase and in the liquid phase. Hydrogenation in the liquid phase is preferred because the gas phase process requires a greater amount of energy because of the necessary cycle control of large gas volumes.
  • Different process variants can be selected for continuous liquid phase hydrogenation. It can be carried out adiabatically or practically isothermally, ie with a temperature rise of less than 10 ° C, in one or more stages. In the latter case, the reactors can be operated adiabatically or practically isothermally or one can be operated adiabatically and the others practically isothermally.
  • the hydrogenation is carried out in the liquid / gas mixed phase or in the liquid phase in three-phase reactors in cocurrent, the hydrogen being finely distributed in the liquid to be hydrogenated in a manner known per se.
  • the reactors are preferably operated with high liquid loads of 15 to 300, in particular 25 to 150 m 3 per m 2 cross section of the empty reactor and hour.
  • a hydrogenation process for the production of 6-methylheptan-2-one is, for example, the liquid phase hydrogenation in two or more reactors, all of which are operated with product recycling, as described in US Pat. No. 5,831,135.
  • the selective hydrogenation in the process according to the invention from 6-methylhept-3-en-2-one to 6-methylheptan-2-one takes place in the temperature range 0 to 200 ° C., in particular 40 to 150 ° C.
  • the reaction pressure is between 1 and 200 bar, preferably 1 to 30 bar, in particular 1 to 15 bar.
  • the selective hydrogenation has the advantage that with practically 100% conversion, the target product is obtained in a yield of over 99%. Any saturated carbonyl compounds present in the starting material, such as 3-methylbutanal or acetone, are almost not hydrogenated.
  • the 6-methylheptan-2-one produced by the process according to the invention is an intermediate for the production of isophytol, a building block for the synthesis of vitamin E. Furthermore, this compound is used for the production of tetrahydrolinalool, dihydrogeraniol and other flavorings.
  • the test was carried out in a test facility consisting of a bubble column reactor, a thin-film evaporator and a distillation device.
  • the isobutene was introduced below, together with an excess of synthesis gas and a high-boiling solvent containing the catalyst, into the bubble column. Unreacted synthesis gas was removed at the top of the reactor.
  • the liquid fractions residual olefin, aldehydes, by-products, high-boiling solvent, catalyst
  • the high-boiling solvent used was dioctyl phthalate, which was present in the reactor at 20% by weight, because when the test was started there were no high boilers from the process and little would form during the test period.
  • the rhodium concentration in the reactor was 30 ppm rhodium, tris (2.4-ditert.-butylphenyl) phosphite was added as the ligand, the P / Rh ratio was 20/1.
  • the bubble column was heated from the outside to a constant 115 ° C via a double jacket, the operating pressure was 50 bar synthesis gas.
  • the aldolization was carried out in a test apparatus which is shown schematically in FIG. 1.
  • a pump 1 is used to pump the continuous catalyst phase 2 into the circuit.
  • aldehyde and ketone are mixed together through line 3 or separately through lines 3 and 4.
  • the starting materials were mixed in exclusively via line 3.
  • the multiphase mixture is 5 pumped through the tube reactor 6 with a length of 3 m and a diameter of 17.3 mm, which was provided with static mixing elements with a hydraulic diameter of 2 mm.
  • the resulting mixture 7, consisting of the reaction product, unreacted starting material and the catalyst, can be freed of volatile constituents in the gas separator 8 by discharge in line 9.
  • this line was closed.
  • the liquid stream 10 occurring after the degassing 8 is passed into a phase separation container 11.
  • the aqueous catalyst phase 2 is separated off and returned to the circuit.
  • the organic phase which has passed over a weir and which contains the reaction product is removed from line 12.
  • the heat of reaction can be removed via heat exchangers 13, 14 and 15 located outside the reactor.
  • the first table attached to the example first describes the catalyst composition in mass percentages, then the amount of the starting material and its composition in mass percentages of the gas chromatographic analysis.
  • the product composition is also listed in mass percentages of the gas chromatographic analysis.
  • the space-time yield (RZA), the conversion (U) of the aldehydes, the selectivity (S) for the desired aldol condensation products and the loading factor (B) are given.
  • RZA space-time yield
  • U conversion of the aldehydes
  • S selectivity for the desired aldol condensation products
  • B loading factor
  • This example describes the process according to the invention for the aldol condensation of acetone (Ac) and 3-methylbutanal (3-MBA) in cyclohexane (CH) to 6-methyl-3-he ⁇ ten-2-one (6-MH).
  • the formation of the by-products 4-methyl-3-penten-2-one (4-MP), 3-methyl-2-isopropyl-2-butenal (3-MiPB), 5-methyl-2-isopropyl-2-hexenal ( 5-MiPH), 4-hydroxy-6-methylheptan-2-one (6-HMH) and the other high boilers (HS) are given in the table below in% by weight.
  • the reactor was flowed through with a catalyst load of 400 kg / h at a temperature of 80 ° C. at the autogenous pressure of the reactants.
  • 6-methyl-3-methylhepten-2-one can be prepared with high selectivity with high space-time yields using the process according to the invention.
  • the example hydrogenation of 6-methyl-3-hepten-2-one (6-MH) to 6-methylheptan-2-one (6-MHa) was carried out in a differential cycle reactor under isothermal and isobaric conditions.
  • 70 g of a Pd / Al 2 O 3 contact were used as catalyst.
  • the fixed bed had a diameter of 4 mm.
  • the catalyst used was previously reduced at 80 ° C and a hydrogen pressure of 15 bar over a period of 18 h.
  • the circulation volume flow of the reaction mixture was 45 l / h. This corresponds to a cross-sectional load of 35 m 3 / m / h.
  • Methylheptan-2-ol (6-MHO) and high boilers (HS) analyzed.

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

Abstract

L'invention concerne un procédé pour la production de 6-méthylheptan-2-one, caractérisé par les étapes suivantes : a) hydroformylation d'isobutène en 3-méthylbutanal, b) condensation aldolique catalysée par une base du 3-méthylbutanal avec de l'acétone en 6-méthylhept-3-én-2-one, le rapport molaire du 3-méthylbutanal à la base utilisée étant supérieur à 1:0,3, et c) hydrogénation de la 6-méthylhept-3-én-2-one en 6-méthylheptan-2-one. L'invention concerne également l'utilisation de la 6-méthylheptan-2-one ainsi produite pour l'obtention d'isophytol, de tétrahydrolinalool ou de dihydrogéraniol.
EP02777243A 2001-10-06 2002-09-27 Procede pour la production de 6-methylheptan-2-one et utilisation de cette derniere Withdrawn EP1440051A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10149349 2001-10-06
DE10149349A DE10149349A1 (de) 2001-10-06 2001-10-06 Verfahren zur Herstellung von 6-Methylheptan-2-on und dessen Verwendung
PCT/EP2002/010873 WO2003031383A1 (fr) 2001-10-06 2002-09-27 Procede pour la production de 6-methylheptan-2-one et utilisation de cette derniere

Publications (1)

Publication Number Publication Date
EP1440051A1 true EP1440051A1 (fr) 2004-07-28

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Country Link
US (1) US20040249218A1 (fr)
EP (1) EP1440051A1 (fr)
JP (1) JP2005504839A (fr)
CN (1) CN1564797A (fr)
AR (1) AR036733A1 (fr)
DE (1) DE10149349A1 (fr)
WO (1) WO2003031383A1 (fr)

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GB0322247D0 (en) * 2003-09-23 2003-10-22 Exxonmobil Chem Patents Inc Improvement in or relating to an isobutylene containing stream
EP1789374B1 (fr) * 2004-09-14 2010-12-29 DSM IP Assets B.V. Procede de preparation de cetones aliphatiques saturees
CN104478683B (zh) * 2014-09-24 2016-03-09 浙江新化化工股份有限公司 一种2-庚酮的合成方法
CN105037120B (zh) * 2015-05-25 2016-09-21 吉林北沙制药有限公司 一种甲基庚酮的新型合成方法
CN104926631A (zh) * 2015-05-30 2015-09-23 吉林众鑫化工集团有限公司 一种以3-甲基-3-丁烯基-1醇制备异戊醛的方法
CN116041158A (zh) * 2021-10-28 2023-05-02 中国石油化工股份有限公司 4-甲基-3-戊烯-2-酮液相加氢制备甲基异丁酮的方法

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US4599206A (en) * 1984-02-17 1986-07-08 Union Carbide Corporation Transition metal complex catalyzed reactions
JPH0660113B2 (ja) * 1986-07-31 1994-08-10 住友化学工業株式会社 イソバレルアルデヒドおよび／またはイソアミルアルコ−ルの製造方法
WO1996031454A1 (fr) * 1995-04-04 1996-10-10 Kuraray Co., Ltd. Procede de preparation de la 6-methylheptan-2-one
US5955636A (en) * 1996-07-05 1999-09-21 Kuraray Co., Ltd. Process for producing 6-methyl-3-hepten-2-one and 6-methyl-2-heptanone analogues, and process for producing phyton or isophytol

Non-Patent Citations (1)

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Title
See references of WO03031383A1 *

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AR036733A1 (es) 2004-09-29
US20040249218A1 (en) 2004-12-09
CN1564797A (zh) 2005-01-12
WO2003031383A1 (fr) 2003-04-17
JP2005504839A (ja) 2005-02-17
DE10149349A1 (de) 2003-04-17

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