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WO2003039743A1 - Catalyseur supporte d'hydrogenation de nitroaromatiques - Google Patents

Catalyseur supporte d'hydrogenation de nitroaromatiques Download PDF

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Publication number
WO2003039743A1
WO2003039743A1 PCT/EP2002/009874 EP0209874W WO03039743A1 WO 2003039743 A1 WO2003039743 A1 WO 2003039743A1 EP 0209874 W EP0209874 W EP 0209874W WO 03039743 A1 WO03039743 A1 WO 03039743A1
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WO
WIPO (PCT)
Prior art keywords
precious metal
metal component
primary
hydrogenation
catalyst
Prior art date
Application number
PCT/EP2002/009874
Other languages
English (en)
Inventor
Jürgen Krauter
Michael Gross
Uwe Packruhn
Markus Göttlinger
Original Assignee
Degussa Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE10216108A external-priority patent/DE10216108A1/de
Application filed by Degussa Ag filed Critical Degussa Ag
Priority to KR1020047007002A priority Critical patent/KR100971893B1/ko
Priority to EP02779300A priority patent/EP1441850A1/fr
Priority to HU0402102A priority patent/HUP0402102A3/hu
Priority to JP2003541628A priority patent/JP4523275B2/ja
Priority to BR0213928-6A priority patent/BR0213928A/pt
Publication of WO2003039743A1 publication Critical patent/WO2003039743A1/fr

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Classifications

    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/63—Platinum group metals with rare earths or actinides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/648—Vanadium, niobium or tantalum or polonium
    • B01J23/6482—Vanadium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/652—Chromium, molybdenum or tungsten
    • B01J23/6522—Chromium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/656—Manganese, technetium or rhenium
    • B01J23/6562—Manganese
    • 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
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8906—Iron and noble metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon

Definitions

  • the invention relates to a supported hydrogenating catalyst in powder form, a process for its production and its use in the catalytic hydrogenation of nitroaromatics.
  • TDA toluenediamines
  • a number of catalysts are known for the catalytic hydrogenation of nitroaromatics, in particular of dinitrotoluene, in the suspension phase.
  • US 2,823,235 discloses palladium, platinum and palladium- platinum catalysts on black, which are doped with iron. Very similar catalysts, which contain blacks as supports, are disclosed in US 3,127,356.
  • US 4,256,671 discloses, in addition to Pd and Pt, also Ni, Ru and Rh as a precious metal component for catalysts used in the catalytic hydrogenation of dinitrotoluenes to toluenediamines .
  • US 6,096,924 discloses, as a catalytically active component, Rh, Ru, Ir, Pt, Pd, Ni and Co. These metals are applied to powder-form supports. V is used as a doping metal.
  • the former printed publication shows that platinum may be present only in a smaller molar quantity than palladium.
  • the optimum is ca. 20 mol% Pt in relation to Pd. If a larger quantity of Pt is used, lower activity is determined.
  • the object of the present invention is to improve the selectivity and activity of the catalytic hydrogenation of nitroaromatics to aminoaromatics, i.e. to reduce the formation of by-products and to increase the yield of the desired product, through the selection and production of a hydrogenating catalyst.
  • the invention provides a supported hydrogenating catalyst in powder form, which contains, as catalytically active components, a mixture of a primary precious metal component, a secondary precious metal domponent and one or more non-precious metal components, wherein either Pt is used as the primary precious metal component with Pd, Ru, Rh as the secondary precious metal component and V, Fe, Mn, Ce and/or Cr as the non-precious metal component, or Pd is used as the primary precious metal component with Ru, Rh as the secondary precious metal component and V, Fe, Mn, Ce and/or Cr as the non-precious metal component or Pd is used as the primary precious metal component with Pt as the secondary precious metal component and Ce and/or Cr as the non-precious metal component.
  • the hydrogenating catalyst according to the ' invention can contain, per 100 g dry hydrogenating catalyst, 10 to 50 mmol of the primary precious metal component.
  • the proportion of the secondary precious metal component can be 1 to 60 mol% in relation to the primary precious metal component, preferably 8 to 12 mol% in relation to the primary precious metal component and that of the non- precious metal component 1-700 mol%, preferably 100-600 mol% in relation to the primary precious metal component.
  • doping metals for the combination Pd as primary precious metal component and Ru Rh as secondary precious metal component, V, Fe, Mn, Ce and/or Cr are particularly suitable as the non-precious metal component.
  • the secondary precious metal component is responsible for the high activity of the catalyst, the non- precious metal component is decisive for selectivity.
  • the hydrogenating catalyst according to the invention can contain, per 100 g dry hydrogenating catalyst, 15 to 20 mmol of the primary precious metal component, 8 to 12 mol%, in relation to the primary precious metal component, of the secondary precious metal component, and 1 to 600 mol%, in relation to the primary precious metal component, of cerium.
  • Supports in powder form are used as supports, and these powder supports may be physically activated carbons, chemically activated carbons, blacks, aluminium oxides or silicon oxides, preferably physically activated carbons, chemically activated carbons or blacks.
  • the invention further provides a process for the production of the hydrogenating catalyst according to the invention, which is characterised in that an aqueous solution containing the primary and secondary precious metal • components and the non-precious metal component in dissolved form is added to a suspension of a powder-form support material in water, the primary and secondary precious metal components and the non-precious metal component are deposited on the powder-form support using a base and reduction is optionally carried out using a reducing agent such as for example formaldehyde, hydrazine, hydrogen, sodium tetrahydroborate, formic acid or sodium formate.
  • a reducing agent such as for example formaldehyde, hydrazine, hydrogen, sodium tetrahydroborate, formic acid or sodium formate.
  • Reduction can be carried out at a temperature of 0 to 100°C.
  • the order in which the support material, water, metal salt solutions and reducing agents are added can also be varied.
  • reduction can take place with hydrogen on the dried catalyst.
  • the use of a reducing agent is optional, i.e. the catalyst according to the invention can be separated out from the reaction mixture by filtration, without the addition of a reducing agent, after the primary and secondary precious metal and non-precious metal components have been deposited on the support.
  • the catalyst according to the invention can be used for the hydrogenation of nitroaromatics.
  • the catalyst according to the invention can be used in particular for the hydrogenation of nitrobenzene to aniline and for the hydrogenation of dinitrot ⁇ luenes to toluenediamines .
  • the catalytic hydrogenation of the nitro-compound can be carried out in the liquid phase as a continuously or discontinuously operated process at pressures of 1 to 100 bar and temperatures of 0 to 250 °C in the presence of the catalyst according to the invention.
  • the catalytic hydrogenation of the nitro-compound in the liquid phase can be carried out as a continuously or discontinuously operated process at pressures of 1 to 100 bar and temperatures of 0°C to 200°C in the presence of the catalyst according to the invention.
  • the catalytic hydrogenation of nitrobenzene or dinitrotoluenes in the presence of the catalyst according to the invention can be carried out in a continuously or discontinuously operated agitated reactor or in a continuously operated circulating reactor in the presence of a solvent, such as for example methanol or toluene.
  • the solvent can also be a mixture of aniline and water, for the hydrogenation of nitrobenzene, or a mixture of dinitrotoluenes in water, for the hydrogenation of dinitrotoluenes .
  • the hydrogenation of dinitrotoluenes to toluenediamines can be carried out at temperatures of 70 to 200 °C, preferably 90 to 150°C, and pressures of 1 to 100 bar, preferably 10 to 40 bar. If hydrogenation is carried out continuously, the quantity of converted dinitrotoluenes must be replaced by topping up and the product-water mixture must be removed from the reactor.
  • Rh or Ru as a secondary precious metal component would have been expected to have a negative effect as it is known (see for example P. N. Rylander, Catalytic Hydrogenation in Organic Syntheses, Academic Press, 1979, New York, page 175 ff) , that Rh and Ru are highly suitable for hydrogenating aromatic rings and would thus be likely to have poor selectivity (i.e. undesirable secondary reactions) . Surprisingly, this is not observed. Examples
  • Catalysts according to the invention and reference catalysts are produced and their catalytic properties in the hydrogenation of nitroaromatics are compared.
  • Pd-Pt-Fe/SB trimetallic catalyst (1.6% Pd + 0.2% Pt + 4.0% Fe) with Pd as the primary precious metal component, Pt as the secondary precious metal component and a non-precious metal component according to the prior art.
  • the Pd-Pt-Fe/SB (1.6% Pd, 0.2% Pt, 4.0% Fe) catalyst is produced as disclosed in US 3,127,356, Example VII.
  • a solution of 2 g tetrachloropalladic (II) acid (20%), 0.2 g hexachloroplatinic (IV) acid (25%) and 6.98 g cerium (III) chloride heptahydrate in 200 ml deionised water is added to this suspension. After heating to 80°C the pH is set at 6.4 using sodium carbonate solution, and the suspension is stirred and filtered.
  • 100 g dry catalyst contains 1.6% Pd, 0.2% Pt and 10.5% Ce .
  • the catalyst is abbreviated to Pd-Pt-Ce/SB (1.6, 0.2, 10.5).
  • the catalyst Pd-Pt/SB (1.6% Pd, 0.2% Pt) is produced as described in example 1, but instead of the quantities given there, 24.69 g Shawinigan Black is used and no cerium salt. 100 g dry catalyst contains 1.6% Pd and 0.2% Pt .
  • Activated carbon is suspended in 500 ml de-ionised water and the suspension is set at a pH of 10 using sodium carbonate solution. 8 g tetrachloropalladic (II) acid (20%), a solution of the secondary precious metal component and a salt of the non-precious metal component, dissolved in 200 ml de-ionised water are added to this suspension. After heating to 80 °C the pH is set at 6.4 using sodium carbonate solution and the suspension is stirred, reduced with formaldehyde and filtered. The quantities are given in Table 1.
  • Activated carbon is suspended in 500 ml de-ionised water and the suspension is set at a pH of 10 using sodium carbonate solution. 11.6 g hexachloroplatinic (IV) acid (25%) , a solution of the secondary precious metal component and a salt of the non-precious metal component, each dissolved in 200 ml de-ionised water, are added to this suspension. After heating to 80°C, the pH is set at 6.4 with sodium carbonate solution, and the suspension is stirred, reduced with formaldehyde and filtered. The quantities are given in Table 2.
  • the catalysts according to the examples are used in the discontinuous hydrogenation of dinitrotoluene to toluene- diamine and the activity and selectivity of the catalysts are determined.
  • the reaction is carried out in a 0.5 1 Hastelloy autoclave.
  • 40 g 2, 4-Dinitrotoluene, 101 g 2, 4-toluenediamine, 59 g water and 1.2 g catalyst (in relation to the solids) are fed into the autoclave.
  • the gas space is flushed first with nitrogen and then with hydrogen and finally a hydrogen pressure of 10 bar is established.
  • the reaction After heating to 120°C, the reaction is started by switching on the stirring mechanism.
  • the end point of the reaction can be determined precisely by the rapid reduction in hydrogen absorption.
  • toluidines diaminobenzenes (called low-boilers)
  • tars tars describes all compounds which have a longer retention time than the primary product TDA.

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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)

Abstract

La présente invention concerne un catalyseur d'hydrogénation, supporté, sous forme pulvérulente contenant, en tant que composant actif d'un point de vue catalytique, un composant métallique précieux principal, un second composant métallique précieux secondaire et un ou plusieurs composants métalliques non précieux. Ledit catalyseur est utilisé pour l'hydrogénation de nitroaromatiques, notamment de nitrobenzène et de DNT.
PCT/EP2002/009874 2001-11-08 2002-09-04 Catalyseur supporte d'hydrogenation de nitroaromatiques WO2003039743A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1020047007002A KR100971893B1 (ko) 2001-11-08 2002-09-04 니트로방향족 화합물을 수소화시키기 위한 지지된 촉매
EP02779300A EP1441850A1 (fr) 2001-11-08 2002-09-04 Catalyseur supporte d'hydrogenation de nitroaromatiques
HU0402102A HUP0402102A3 (en) 2001-11-08 2002-09-04 Supported hydrogenating catalyst in powder form
JP2003541628A JP4523275B2 (ja) 2001-11-08 2002-09-04 ニトロ芳香族化合物を水素化するための担持触媒
BR0213928-6A BR0213928A (pt) 2001-11-08 2002-09-04 Catalisador suportado para hidrogenação de nitroaromáticos

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE10154811 2001-11-08
DE10154811.7 2001-11-08
US33315301P 2001-11-27 2001-11-27
US60/333,153 2001-11-27
DE10216108A DE10216108A1 (de) 2001-11-08 2002-04-12 Pulverförmiger geträgerter Hydrierkatalysator
DE10216108.9 2002-04-12

Publications (1)

Publication Number Publication Date
WO2003039743A1 true WO2003039743A1 (fr) 2003-05-15

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PCT/EP2002/009874 WO2003039743A1 (fr) 2001-11-08 2002-09-04 Catalyseur supporte d'hydrogenation de nitroaromatiques

Country Status (7)

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EP (1) EP1441850A1 (fr)
JP (1) JP4523275B2 (fr)
CN (1) CN100479916C (fr)
BR (1) BR0213928A (fr)
HU (1) HUP0402102A3 (fr)
PL (1) PL368203A1 (fr)
WO (1) WO2003039743A1 (fr)

Cited By (10)

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Publication number Priority date Publication date Assignee Title
EP1317959B1 (fr) * 2001-12-07 2007-11-14 Basf Aktiengesellschaft Procédé de préparation de catalyseurs de ruthénium/fer sur un support de carbone
JPWO2005061479A1 (ja) * 2003-12-19 2007-12-13 宇部興産株式会社 テトラヒドロピラン−４−オン及びピラン−４−オンの製法
US7468461B2 (en) 2003-10-17 2008-12-23 Basf Aktiengesellschaft Method for the production of amines
CN101429453B (zh) * 2008-03-19 2010-05-12 中国石油天然气股份有限公司 裂解汽油馏分一段选择性加氢方法
CN102000568A (zh) * 2010-11-11 2011-04-06 厦门大学 一种硝基芳香烃的还原方法
US9505705B2 (en) 2005-08-31 2016-11-29 Basf Akteingesellschaft Method for producing amines with a catalyst containing platinum, nickel and an additional metal
CN111013561A (zh) * 2019-12-31 2020-04-17 贵研工业催化剂（云南）有限公司 一种用于硝基苯液相加氢制苯胺的催化剂的制备方法
CN114289034A (zh) * 2021-12-27 2022-04-08 万华化学集团股份有限公司 一种贵金属催化剂和制备方法及其在催化二硝基甲苯加氢制备甲苯二胺应用
CN114534733A (zh) * 2020-11-24 2022-05-27 万华化学集团股份有限公司 一种硝基化合物加氢制芳胺催化剂的制备方法
CN115920972A (zh) * 2022-12-30 2023-04-07 南京师范大学 一种高效催化还原硝基芳烃催化材料合成方法及应用

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CN102952022B (zh) * 2012-09-13 2014-04-09 赛鼎工程有限公司 二硝基甲苯连续制备二胺基甲苯的方法及使用的催化剂和催化剂的制备方法
CN105080567B (zh) * 2014-04-22 2017-09-29 中国科学院长春应用化学研究所 催化剂以及芳香氨基化合物的制备方法
CN105435808A (zh) * 2014-08-20 2016-03-30 中国石油化工股份有限公司 一种炭黑贵金属催化剂的制备方法
CN104971738B (zh) * 2015-07-07 2017-06-27 淮阴工学院 磁性纳米钯催化剂的制备方法
JPWO2017163680A1 (ja) * 2016-03-23 2019-01-31 エヌ・イーケムキャット株式会社 反応組成物及びこれを用いた反応システム
US10322992B2 (en) 2016-12-13 2019-06-18 King Abdulaziz University Methods of making cerium oxide polyaniline composite nanospheres and methods of use
CN109225258A (zh) * 2018-10-19 2019-01-18 郴州高鑫铂业有限公司 一种Pt-Fe/C催化剂及其制备方法和应用
CN113145112B (zh) * 2021-04-30 2023-03-24 福州大学 一种用于二硝基甲苯选择性加氢的Pd-Pt/C催化剂的制备方法
CN114471544A (zh) * 2022-02-25 2022-05-13 天脊煤化工集团股份有限公司 一种催化剂及其在苯胺制备中的应用
CN115445626A (zh) * 2022-09-26 2022-12-09 长春工业大学 一种硝基苯乙炔加氢制备氨基苯乙炔的催化剂

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1317959B1 (fr) * 2001-12-07 2007-11-14 Basf Aktiengesellschaft Procédé de préparation de catalyseurs de ruthénium/fer sur un support de carbone
US7468461B2 (en) 2003-10-17 2008-12-23 Basf Aktiengesellschaft Method for the production of amines
JP4687464B2 (ja) * 2003-12-19 2011-05-25 宇部興産株式会社 テトラヒドロピラン−４−オン及びピラン−４−オンの製法
JPWO2005061479A1 (ja) * 2003-12-19 2007-12-13 宇部興産株式会社 テトラヒドロピラン−４−オン及びピラン−４−オンの製法
US9505705B2 (en) 2005-08-31 2016-11-29 Basf Akteingesellschaft Method for producing amines with a catalyst containing platinum, nickel and an additional metal
CN101429453B (zh) * 2008-03-19 2010-05-12 中国石油天然气股份有限公司 裂解汽油馏分一段选择性加氢方法
CN102000568A (zh) * 2010-11-11 2011-04-06 厦门大学 一种硝基芳香烃的还原方法
CN111013561A (zh) * 2019-12-31 2020-04-17 贵研工业催化剂（云南）有限公司 一种用于硝基苯液相加氢制苯胺的催化剂的制备方法
CN114534733A (zh) * 2020-11-24 2022-05-27 万华化学集团股份有限公司 一种硝基化合物加氢制芳胺催化剂的制备方法
CN114534733B (zh) * 2020-11-24 2024-04-12 万华化学集团股份有限公司 一种硝基化合物加氢制芳胺催化剂的制备方法
CN114289034A (zh) * 2021-12-27 2022-04-08 万华化学集团股份有限公司 一种贵金属催化剂和制备方法及其在催化二硝基甲苯加氢制备甲苯二胺应用
CN114289034B (zh) * 2021-12-27 2024-02-02 万华化学集团股份有限公司 一种贵金属催化剂和制备方法及其在催化二硝基甲苯加氢制备甲苯二胺应用
CN115920972A (zh) * 2022-12-30 2023-04-07 南京师范大学 一种高效催化还原硝基芳烃催化材料合成方法及应用

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BR0213928A (pt) 2004-08-31
HUP0402102A2 (hu) 2005-01-28
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JP2005526589A (ja) 2005-09-08
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