JP4550064B2 - アミンの製造方法 - Google Patents
アミンの製造方法 Download PDFInfo
- Publication number
- JP4550064B2 JP4550064B2 JP2006534705A JP2006534705A JP4550064B2 JP 4550064 B2 JP4550064 B2 JP 4550064B2 JP 2006534705 A JP2006534705 A JP 2006534705A JP 2006534705 A JP2006534705 A JP 2006534705A JP 4550064 B2 JP4550064 B2 JP 4550064B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- nickel
- platinum
- hydrogenation
- weight
- 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.)
- Expired - Fee Related
Links
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
- B01J23/70—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
-
- 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
- B01J23/892—Nickel and noble metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/51—Phenylenediamines
-
- 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
-
- 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
-
- 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
- B01J37/12—Oxidising
- B01J37/14—Oxidising with gases containing free oxygen
-
- 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
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
ノリツ(Norit)(登録商標)SX+活性炭担体を皿に最初に取り込み、そして、触媒の質量に対して3質量%の白金を得るための白金(II)硝酸塩と、触媒の質量に対して1質量%のニッケルを得るためのニッケル(II)硝酸塩の六水和物(硝酸ニッケル(II)六水和物)とを、担体の量に対して100質量%の量の水に溶解し、そして担体へ添加して混練可能なペーストを得た。ペーストを十分に混合した。溶剤としての水を、60℃及び0.2〜0.4バールの圧力での穏やかな煮沸が行われるロータリエバポレータ中において蒸発させた。担体の量に対して16質量%の量の炭酸ナトリウムを担体に対して100質量%の水に溶解させた水溶液を添加することによって、金属をアルカリ条件下で担体に固定し、そして試料を洗浄して、硝酸塩を除去した。このようにして得られた触媒を80℃で乾燥し、その後、400℃の水素流下、ロータリ型の球形の炉において4時間還元した。適当な状態に調節する前に、触媒を室温条件下で希薄な空気(窒素に対して5容量%の空気)中にて不動態化した。このようにして得られた触媒を触媒Aと称する。
実施例1の処置を繰り返し行ったが、0.25質量%のニッケルを得るためのニッケル塩のみを使用した。このようにして得られた触媒を触媒Bと称する。ニッケルに対する白金の原子は、78:22であった。
実施例1で用いられた担体を水に懸濁させて、10%懸濁液を得た。このために、実施例1の金属塩を実施例1に記載の割合で添加し、そして煮沸して、ギ酸アンモニウムと共に2時間還流した。このようにして得られた触媒を洗浄して、触媒から硝酸塩を取り除いた。この処置において、白金を還元した;ニッケルは、水酸化物又は酸化物の形で担体に存在してた。このようにして得られた触媒を触媒Cと称する。
実施例3の処置を繰り返し行ったが、ニッケル塩を添加しなかった。このようにして得られた触媒を触媒Dと称する。
触媒Eとして、5質量%の活性炭に担持させた市販のPd含有参考用触媒(50%水湿潤)を使用した。
触媒Fとして、ZrO2担体に担持させた市販のニッケル触媒を使用した。
DNTのTDAへの水素化:
DNTのTDAへの水素化を300mlの連続撹拌器付きタンク中で行った;触媒を反応器中に機械的に保持させた。
Claims (8)
- 水素化触媒の存在下で芳香族ニトロ化合物を対応のアミンに水素化する方法であって、水素化触媒として、ニッケル及び白金が担体に合金の状態で施された触媒を使用し、合金中の白金に対するニッケルの原子比が30:70〜70:30の範囲であり、
芳香族ニトロ化合物としてジニトロトルエンを用いることを特徴とする方法。 - 合金中の白金に対するニッケルの原子比が40:60〜60:40の範囲である請求項1に記載の方法。
- 合金中の白金に対するニッケルの原子比が45:55〜55:45の範囲である請求項1に記載の方法。
- 触媒を、反応混合物に対して0.01〜10質量%の量で使用する請求項1に記載の方法。
- 触媒を、反応混合物に対して0.1〜5質量%の量で使用する請求項1に記載の方法。
- 触媒を、反応混合物に対して0.2〜2質量%の量で使用する請求項1に記載の方法。
- 水素化を80〜250℃の範囲の温度で行う請求項1に記載の方法。
- 使用される触媒を、その触媒の充填限界で用いる請求項1に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10349095A DE10349095A1 (de) | 2003-10-17 | 2003-10-17 | Verfahren zur Herstellung von Aminen |
PCT/EP2004/011642 WO2005037768A1 (de) | 2003-10-17 | 2004-10-15 | Verfahren zur herstellung von aminen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007508348A JP2007508348A (ja) | 2007-04-05 |
JP4550064B2 true JP4550064B2 (ja) | 2010-09-22 |
Family
ID=34442189
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006534705A Expired - Fee Related JP4550064B2 (ja) | 2003-10-17 | 2004-10-15 | アミンの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (2) | US20070149814A1 (ja) |
EP (1) | EP1678118B1 (ja) |
JP (1) | JP4550064B2 (ja) |
KR (1) | KR101125985B1 (ja) |
CN (1) | CN100364957C (ja) |
AT (1) | ATE554061T1 (ja) |
DE (1) | DE10349095A1 (ja) |
PT (1) | PT1678118E (ja) |
WO (1) | WO2005037768A1 (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005041532A1 (de) * | 2005-08-31 | 2007-03-01 | Basf Ag | Verfahren zur Herstellung von Aminen |
EP2177267B1 (en) * | 2007-08-13 | 2013-07-31 | Asahi Kasei Chemicals Corporation | Catalyst for carboxylic acid ester production, method for producing the same, and method for producing carboxylic acid ester |
JP5665743B2 (ja) * | 2008-08-26 | 2015-02-04 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 触媒の連続的な製造方法 |
US9079822B2 (en) | 2009-02-26 | 2015-07-14 | Basf Se | Process for the preparation of nitrated aromatics and mixtures thereof |
JP2010241691A (ja) * | 2009-03-31 | 2010-10-28 | National Institute Of Advanced Industrial Science & Technology | 金属ナノ粒子担持mcm−41触媒を用いるニトロ化合物の水素還元方法 |
ES2502537T3 (es) | 2009-10-27 | 2014-10-03 | Basf Se | Procedimiento para la producción acoplada de di- y/o poliisocianatos y glicoles |
US20110189589A1 (en) * | 2010-01-29 | 2011-08-04 | The Johns Hopkins University | Composite porous catalysts |
SG185374A1 (en) | 2010-05-17 | 2012-12-28 | Basf Se | Process for preparing tolylenediamine by hydrogenation of dinitrotoluene |
CN103313962B (zh) * | 2010-12-06 | 2014-12-24 | 巴斯夫欧洲公司 | 制备芳胺的方法 |
US8981155B2 (en) | 2010-12-06 | 2015-03-17 | Basf Se | Process for preparing aromatic amines |
US9302237B2 (en) | 2013-01-11 | 2016-04-05 | Basf Se | Apparatus and process for the continuous reaction of liquids with gases |
US9295971B2 (en) | 2013-01-11 | 2016-03-29 | Basf Se | Apparatus and process for the continuous reaction of liquids with gases |
WO2014108351A1 (de) | 2013-01-11 | 2014-07-17 | Basf Se | Vorrichtung und verfahren zur kontinuierlichen umsetzung von flüssigkeiten mit gasen |
WO2018069278A1 (de) | 2016-10-10 | 2018-04-19 | Basf Se | Katalysatormodifikation mit alkalimetall-, erdalkalimetall- oder seltenerdmetallionen in der kontinuierlichen flüssigphasen-hydrierung von nitroverbindungen |
WO2019076658A1 (de) | 2017-10-16 | 2019-04-25 | Basf Se | Erhöhung der katalysatorselektivität bei der kontinuierlichen hydrierung von nitroverbindungen durch zugabe von ammoniak |
KR20240005006A (ko) * | 2021-05-06 | 2024-01-11 | 바스프 에스이 | Ni, 하나 이상의 추가 금속 M, 및 특정 산화물 지지체 물질을 포함하는 수소화 반응에 적합한 촉매 물질 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3127356A (en) * | 1964-03-31 | Process for the preparation of hydro- | ||
GB1201050A (en) * | 1967-11-24 | 1970-08-05 | Ici Ltd | Reduction process |
US4185036A (en) * | 1973-12-28 | 1980-01-22 | E. I. Du Pont De Nemours And Company | Hydrogenation of mixed aromatic nitrobodies |
CA1111451A (en) * | 1977-11-24 | 1981-10-27 | John D. Hildreth | Process for the preparation of diaminotoluenes |
US4237070A (en) * | 1978-09-20 | 1980-12-02 | Texaco Inc. | Novel process for preparing aniline by catalytic reaction of vinyl cyclohexene and nitrobenzene |
DE3315191A1 (de) | 1983-04-27 | 1984-10-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen herstellung von aromatischen diaminen unter gleichzeitiger erzeugung von dampf |
DE3928329A1 (de) | 1989-08-26 | 1991-02-28 | Bayer Ag | Verfahren zur herstellung von chlorsubstituierten aromatischen aminen |
JP2801358B2 (ja) * | 1990-05-15 | 1998-09-21 | 三井化学株式会社 | 高純度アニリンの製造方法 |
US5214212A (en) * | 1992-02-27 | 1993-05-25 | Olin Corporation | Promoters for hydrogenation of aromatic amines |
DE4236203A1 (de) * | 1992-10-27 | 1994-04-28 | Bayer Ag | Verfahren zur Herstellung von chlorsubstituierten aromatischen Aminen und von Katalysatoren |
US5759944A (en) * | 1993-04-20 | 1998-06-02 | Johnson Matthey Public Limited Company | Catalyst material |
US5689000A (en) | 1994-07-01 | 1997-11-18 | Monsanto Company | Process for preparing carboxylic acid salts and catalysts useful in such process |
FI107382B (fi) * | 1996-02-23 | 2001-07-31 | Valtion Teknillinen | Menetelmä aromaattisten nitroyhdisteiden pelkistämiseksi |
JPH09225317A (ja) * | 1996-02-26 | 1997-09-02 | Kemipuro Kasei Kk | ニッケル/貴金属二元金属クラスター、それよりなる触媒およびその製法 |
DE19608443C1 (de) * | 1996-03-05 | 1997-07-24 | Bayer Ag | Verfahren zur Aufarbeitung von Amingemischen bei der Diaminotoluol-Herstellung unter Abtrennung der Schwersieder |
DE19636214A1 (de) | 1996-07-23 | 1998-01-29 | Degussa | Multimetallischer Katalysator und Verfahren zur Herstellung substituierter aromatischer Amine |
US6242649B1 (en) * | 1997-10-15 | 2001-06-05 | Bayer Aktiengesellschaft | Continuous method for producing aromatic amines |
DE19911865A1 (de) * | 1999-03-17 | 2000-09-28 | Degussa | Verfahren zur katalytischen Hydrierung von Dinitrotoluol sowie Katalysator |
IT1318602B1 (it) * | 2000-06-29 | 2003-08-27 | Enichem Spa | Procedimento per la produzione di ammine aromatiche. |
US6818720B2 (en) * | 2001-11-08 | 2004-11-16 | Degussa Ag | Supported hydrogenating catalyst in powder form |
HUP0402102A3 (en) | 2001-11-08 | 2010-07-28 | Evonik Degussa Gmbh | Supported hydrogenating catalyst in powder form |
US20050070740A1 (en) * | 2003-09-29 | 2005-03-31 | Rode Chandrashekhar Vasant | Nickel catalyst, process for the preparation thereof, process for hydrogenation of m-dinitro benzene to m-phenylene diamine |
-
2003
- 2003-10-17 DE DE10349095A patent/DE10349095A1/de not_active Withdrawn
-
2004
- 2004-10-15 US US10/575,924 patent/US20070149814A1/en not_active Abandoned
- 2004-10-15 CN CNB2004800305165A patent/CN100364957C/zh active Active
- 2004-10-15 WO PCT/EP2004/011642 patent/WO2005037768A1/de active Application Filing
- 2004-10-15 JP JP2006534705A patent/JP4550064B2/ja not_active Expired - Fee Related
- 2004-10-15 AT AT04790484T patent/ATE554061T1/de active
- 2004-10-15 EP EP04790484A patent/EP1678118B1/de active Active
- 2004-10-15 KR KR1020067008988A patent/KR101125985B1/ko active IP Right Grant
- 2004-10-15 PT PT04790484T patent/PT1678118E/pt unknown
-
2008
- 2008-03-28 US US12/057,617 patent/US7468461B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
US20080177111A1 (en) | 2008-07-24 |
PT1678118E (pt) | 2012-05-07 |
DE10349095A1 (de) | 2005-05-19 |
JP2007508348A (ja) | 2007-04-05 |
CN1867538A (zh) | 2006-11-22 |
EP1678118B1 (de) | 2012-04-18 |
EP1678118A1 (de) | 2006-07-12 |
WO2005037768A1 (de) | 2005-04-28 |
US20070149814A1 (en) | 2007-06-28 |
KR101125985B1 (ko) | 2012-04-18 |
ATE554061T1 (de) | 2012-05-15 |
CN100364957C (zh) | 2008-01-30 |
KR20070007762A (ko) | 2007-01-16 |
US7468461B2 (en) | 2008-12-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5473901B2 (ja) | アミンの製造方法 | |
US7468461B2 (en) | Method for the production of amines | |
JP5389441B2 (ja) | アミンの製造 | |
US10538478B2 (en) | Catalyst modification with alkali metal, alkaline earth metal or rare earth metal ions in the continuous liquid-phase hydrogenation of nitro compounds | |
JP4523275B2 (ja) | ニトロ芳香族化合物を水素化するための担持触媒 | |
US6818720B2 (en) | Supported hydrogenating catalyst in powder form | |
KR100971893B1 (ko) | 니트로방향족 화합물을 수소화시키기 위한 지지된 촉매 | |
US11339115B2 (en) | Increasing the catalyst selectivity in the continuous hydrogenation of nitro compounds by adding ammonia |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20091019 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091110 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100204 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100212 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100510 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100608 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100707 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130716 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |