KR970001303A - 기상 수소첨가반응에 의한 방향족 아민의 제조 방법 및 그에 유용한 촉매 - Google Patents
기상 수소첨가반응에 의한 방향족 아민의 제조 방법 및 그에 유용한 촉매 Download PDFInfo
- Publication number
- KR970001303A KR970001303A KR1019960021210A KR19960021210A KR970001303A KR 970001303 A KR970001303 A KR 970001303A KR 1019960021210 A KR1019960021210 A KR 1019960021210A KR 19960021210 A KR19960021210 A KR 19960021210A KR 970001303 A KR970001303 A KR 970001303A
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- hydrogen
- palladium
- weight
- graphite
- Prior art date
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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
-
- 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
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/628—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with lead
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- 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)
Abstract
본 발명은 니트로방향족 화합물을 기상 촉매 수소첨가반응시켜 방향족 아민을 제조하는 방법에 관한 것이다. 촉매는 그라파이트 도는 그라파이트 함유 코우크스 담체 상의 팔라듐 및 납이다. 이 방법 동안에 니트로기 1당량 당 30 내지 6000당량의 수소를 촉매와 접촉시킨다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기 일반식(Ⅱ)의 니트로방향족 화합물을 고정된 촉매 상에서, 니트로기 1당량 당 약 30 내지 6000당량의 수소가 촉매와 접촉되는 양으로 수소로 기상 수소 첨가반응시키는 것을 포함하고, 이 때 상기 고정된 촉매가 0.2 내지 10m/g의 DET 비표면적을 갖는 그라파이트 또는 그라파이트 함유 코우크스 담체 상에 상기 촉매의 총량을 기준으로 하여 0.001 내지 7중량%의 팔라듐 및 상기 팔라듐의 중량을 기준으로 하여 0.1 내지 50중량%의 납으로 구성되는 하기 일반식(Ⅰ)의 방향족 아민의 제조 방법.(Ⅱ)(상기 식 중, R2및 R3은 독립적으로 각각 수소, 메틸기 또는 에틸기를 나타내고, R3는 또한 니트로기를 나타낼 수도 있다)(I)(상기 식 중, R1및 R2는 독립적으로 각각 수소, 메틸기 또는 에틸기를 나타내고 R1은 또한 아미노기를 나타낼 수도 있다.)
- 재1항에 있어서, 상기 수소첨가반응을 약 1 내지 약 30바아의 운전 압력에서 수행하는 방법.
- 제1항에 있어서, 상기 니트로방향족 화합물 및 수소를 함유하는 출발 물질 가스 혼합물이 촉매와 접촉하기 전에 200 내지 400℃의 온도를 갖고, 최대 촉매 온도가 600℃인 방법.
- 제1항에 있어서, 촉매 부하량을 1시간 촉매 1리터 당 0.05 내지 20kg의 니트로방향족 화합물로 설정한 방법.
- 제1항에 있어서, 반응열의 제거를 위한 시스템이 없는 반응기를 사용하는 방법.
- 제1항에 있어서, 상기 니트로방향족 화합물이 니트로벤젠 또는 니트로톨루엔인 방법.
- 촉매의 총량을 기준으로 하여 0.001 내지 7중량%의 팔라듐 및 상기 팔라듐의 중량을 기준으로 하여 0.1 내지 50중량%의 납으로 합침시킨, 0.2 내지 10m2/g의 BET 비표면적을 갖는 그라파이트 또는 그라파이트 함유 코우크스 상에서 니트로방향족 화합물을 수소첨가반응시키기에 적합한 촉매.
- 제7항에 있어서, 팔라듐 함유 용액이 1 내지 50회의 함침 단계로 단계상에 침착되고, 각 침착 단계 사이에 촉매 담체를 고온 기류로 건조시킴으로써 담체가 팔라듐으로 함침되는 촉매.
- 제7항에 있어서, 촉매를 250 내지 450℃의 온도 및 1 내지 10바아의 수소 스트림 중에서 활성화시킨 촉매.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19521587.7 | 1995-06-14 | ||
DE19521587A DE19521587A1 (de) | 1995-06-14 | 1995-06-14 | Verfahren und Katalysator zur Herstellung von aromatischen Aminen durch Gasphasenhydrierung |
Publications (2)
Publication Number | Publication Date |
---|---|
KR970001303A true KR970001303A (ko) | 1997-01-24 |
KR100413574B1 KR100413574B1 (ko) | 2004-04-01 |
Family
ID=7764331
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960021210A KR100413574B1 (ko) | 1995-06-14 | 1996-06-13 | 기상수소첨가반응에의한방향족아민의제조방법및그에유용한촉매 |
Country Status (13)
Country | Link |
---|---|
US (2) | US5679858A (ko) |
EP (1) | EP0748790B1 (ko) |
JP (1) | JPH093012A (ko) |
KR (1) | KR100413574B1 (ko) |
CN (1) | CN1119318C (ko) |
BR (1) | BR9602789A (ko) |
CA (1) | CA2178701A1 (ko) |
CZ (1) | CZ287873B6 (ko) |
DE (2) | DE19521587A1 (ko) |
ES (1) | ES2139277T3 (ko) |
PL (1) | PL183111B1 (ko) |
SI (1) | SI0748790T1 (ko) |
TW (1) | TW418182B (ko) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19715746A1 (de) * | 1997-04-16 | 1998-10-22 | Bayer Ag | Herstellung von aromatischen Aminen mittels neuer Hydrierkatalysatoren |
US6005143A (en) * | 1998-08-07 | 1999-12-21 | Air Products And Chemicals, Inc. | Use of a monolith catalyst for the hydrogenation of dinitrotoluene to toluenediamine |
DE10255240A1 (de) * | 2002-11-26 | 2004-06-09 | Basf Ag | Verfahren zur Entfernung von Quecksilber aus mit Quecksilber verunreinigten Lösungen |
US7288500B2 (en) * | 2005-08-31 | 2007-10-30 | Headwaters Technology Innovation, Llc | Selective hydrogenation of nitro groups of halonitro aromatic compounds |
US7396795B2 (en) | 2005-08-31 | 2008-07-08 | Headwaters Technology Innovation, Llc | Low temperature preparation of supported nanoparticle catalysts having increased dispersion |
US7892299B2 (en) * | 2005-09-15 | 2011-02-22 | Headwaters Technology Innovation, Llc | Methods of manufacturing fuel cell electrodes incorporating highly dispersed nanoparticle catalysts |
US7935652B2 (en) * | 2005-09-15 | 2011-05-03 | Headwaters Technology Innovation, Llc. | Supported nanoparticle catalysts manufactured using caged catalyst atoms |
US7718710B2 (en) | 2006-03-17 | 2010-05-18 | Headwaters Technology Innovation, Llc | Stable concentrated metal colloids and methods of making same |
DE102006035203A1 (de) * | 2006-07-29 | 2008-01-31 | Bayer Materialscience Ag | Verfahren zur Herstellung von aromatischen Aminen |
US7563742B2 (en) | 2006-09-22 | 2009-07-21 | Headwaters Technology Innovation, Llc | Supported nickel catalysts having high nickel loading and high metal dispersion and methods of making same |
DE102009019436A1 (de) * | 2009-04-29 | 2010-11-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von aromatischen Aminen |
US9115049B2 (en) | 2012-10-11 | 2015-08-25 | Basf Se | Process for obtaining pure aniline |
EP2906528B1 (de) | 2012-10-11 | 2016-09-21 | Basf Se | Verfahren zur gewinnung von rein-anilin |
US9518006B2 (en) | 2013-10-08 | 2016-12-13 | Covestro Deutschland Ag | Method for producing diaminotoluene |
JP6327607B2 (ja) * | 2014-03-11 | 2018-05-23 | 公立大学法人首都大学東京 | パラジウム粒子を有機高分子化合物に担持した複合体 |
US20240317673A1 (en) | 2021-06-30 | 2024-09-26 | Basf Se | Process for producing aniline |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2285277A (en) * | 1939-11-08 | 1942-06-02 | Du Pont | Noble metal catalyst and process of preparing same |
US2681938A (en) * | 1949-08-15 | 1954-06-22 | Hoffmann La Roche | Hydrogenation of acetylenic bond utilizing a palladium-lead catalyst |
US2823235A (en) * | 1955-05-10 | 1958-02-11 | Du Pont | Hydrogenation of nitro compounds to amines and catalyst therefor |
US3136818A (en) * | 1960-01-15 | 1964-06-09 | Basf Ag | Production of aniline |
US3132180A (en) * | 1961-03-29 | 1964-05-05 | Gen Aniline & Film Corp | Catalytic reduction of aromatic mononitro compounds |
US3265636A (en) * | 1963-03-26 | 1966-08-09 | Du Pont | Catalyst for the hydrogenation of nitro compounds |
US3657265A (en) * | 1968-06-21 | 1972-04-18 | Olin Corp | Process for preparing benzoxazolones from aromatic nitro compounds |
US3666813A (en) * | 1969-08-27 | 1972-05-30 | Engelhard Min & Chem | Process for preparing aromatic haloamines from aromatic nitroamines |
BE793860A (fr) * | 1972-03-23 | 1973-07-10 | Bayer Ag | Catalyseur utilisable notamment pour la reduction de nitrobenzene |
US3804779A (en) * | 1972-10-02 | 1974-04-16 | Dart Ind Inc | Carbon supported palladium catalyst |
DE2849002A1 (de) * | 1978-11-11 | 1980-05-22 | Bayer Ag | Verfahren zur katalytischen hydrierung von nitrobenzol |
DE2943805A1 (de) * | 1979-10-30 | 1981-05-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-phenoxy-benzaldehyden |
JP2801381B2 (ja) * | 1990-09-18 | 1998-09-21 | 三井化学株式会社 | 高純度アニリンの製造法 |
DE4039026A1 (de) * | 1990-12-07 | 1992-06-11 | Bayer Ag | Verfahren zur herstellung von anilin |
FR2671347B1 (fr) * | 1991-01-07 | 1994-09-09 | Inst Francais Du Petrole | Reduction catalytique de composes nitroaromatiques substitues ou non en composes aminoaromatiques correspondants. |
DE4428017A1 (de) * | 1994-08-08 | 1996-02-15 | Bayer Ag | Verfahren zur Herstellung von aromatischen Aminen |
-
1995
- 1995-06-14 DE DE19521587A patent/DE19521587A1/de not_active Withdrawn
-
1996
- 1996-06-03 SI SI9630099T patent/SI0748790T1/xx not_active IP Right Cessation
- 1996-06-03 DE DE59603397T patent/DE59603397D1/de not_active Expired - Fee Related
- 1996-06-03 EP EP96108856A patent/EP0748790B1/de not_active Expired - Lifetime
- 1996-06-03 ES ES96108856T patent/ES2139277T3/es not_active Expired - Lifetime
- 1996-06-06 US US08/660,622 patent/US5679858A/en not_active Expired - Fee Related
- 1996-06-10 CA CA002178701A patent/CA2178701A1/en not_active Abandoned
- 1996-06-10 TW TW085106931A patent/TW418182B/zh not_active IP Right Cessation
- 1996-06-11 JP JP8170700A patent/JPH093012A/ja not_active Abandoned
- 1996-06-12 PL PL96314749A patent/PL183111B1/pl unknown
- 1996-06-13 KR KR1019960021210A patent/KR100413574B1/ko not_active IP Right Cessation
- 1996-06-13 CZ CZ19961740A patent/CZ287873B6/cs not_active IP Right Cessation
- 1996-06-13 BR BR9602789A patent/BR9602789A/pt not_active Application Discontinuation
- 1996-06-14 CN CN96106186A patent/CN1119318C/zh not_active Expired - Fee Related
-
1997
- 1997-06-19 US US08/878,592 patent/US5962365A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CZ287873B6 (en) | 2001-02-14 |
JPH093012A (ja) | 1997-01-07 |
US5962365A (en) | 1999-10-05 |
BR9602789A (pt) | 1998-09-08 |
ES2139277T3 (es) | 2000-02-01 |
CN1143073A (zh) | 1997-02-19 |
PL314749A1 (en) | 1996-12-23 |
EP0748790B1 (de) | 1999-10-20 |
US5679858A (en) | 1997-10-21 |
KR100413574B1 (ko) | 2004-04-01 |
EP0748790A2 (de) | 1996-12-18 |
CZ174096A3 (en) | 1997-01-15 |
EP0748790A3 (de) | 1998-04-08 |
DE19521587A1 (de) | 1996-12-19 |
CN1119318C (zh) | 2003-08-27 |
CA2178701A1 (en) | 1996-12-15 |
SI0748790T1 (en) | 1999-12-31 |
TW418182B (en) | 2001-01-11 |
PL183111B1 (pl) | 2002-05-31 |
DE59603397D1 (de) | 1999-11-25 |
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