TWI265919B - Process for preparing 4-aminodiphenylamine intermediates - Google Patents
Process for preparing 4-aminodiphenylamine intermediatesInfo
- Publication number
- TWI265919B TWI265919B TW091116246A TW91116246A TWI265919B TW I265919 B TWI265919 B TW I265919B TW 091116246 A TW091116246 A TW 091116246A TW 91116246 A TW91116246 A TW 91116246A TW I265919 B TWI265919 B TW I265919B
- Authority
- TW
- Taiwan
- Prior art keywords
- aminodiphenylamine
- mixture
- nitrobenzene
- aniline
- base
- Prior art date
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
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- 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
Abstract
The invention is directed to a method of producing 4-aminodiphenylamine or substituted derivatives thereof comprising the steps of bringing an aniline or aniline derivative and nitrobenzene or nitrobenzene derivative into reactive contact; and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong base and a suitable phase transfer catalyst and an oxidant to produce a 4-aminodiphenylamine intermediate product. Alternatively, the mixture may comprise an inorganic salt or metal organic salt having a cation that would be a suitable cation of a strong inorganic base, and an oxidant and organic base, the mixture not including a reaction product of betaine and a strong inorganic base. The aminodiphenylamine intermediate product is reduced to produce 4-aminodiphenylamine or substituted derivatives thereof.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/911,058 US6395933B1 (en) | 2001-07-23 | 2001-07-23 | Process for preparing 4-aminodiphenylamine intermediates |
US10/143,478 US6583320B2 (en) | 2001-07-23 | 2002-05-10 | Process for preparing 4-aminodiphenylamine intermediates |
Publications (1)
Publication Number | Publication Date |
---|---|
TWI265919B true TWI265919B (en) | 2006-11-11 |
Family
ID=26841060
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW091116246A TWI265919B (en) | 2001-07-23 | 2002-07-22 | Process for preparing 4-aminodiphenylamine intermediates |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP1414782A1 (en) |
JP (1) | JP4603260B2 (en) |
CN (1) | CN100546972C (en) |
AU (1) | AU2002315530B2 (en) |
BR (1) | BR0211391B1 (en) |
CA (1) | CA2454603A1 (en) |
HU (1) | HUP0501066A2 (en) |
IL (1) | IL159994A0 (en) |
MX (1) | MXPA04000665A (en) |
NO (1) | NO20040292L (en) |
PL (1) | PL206080B1 (en) |
RS (1) | RS3904A (en) |
RU (1) | RU2280640C2 (en) |
TW (1) | TWI265919B (en) |
WO (1) | WO2003010126A1 (en) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6395933B1 (en) * | 2001-07-23 | 2002-05-28 | Flexsys America, L.P. | Process for preparing 4-aminodiphenylamine intermediates |
US7183439B2 (en) * | 2002-12-10 | 2007-02-27 | Flexsys America L.P. | Process for preparing 4-aminodiphenylamine intermediates |
US8486223B2 (en) | 2003-07-04 | 2013-07-16 | Jiangsu Sinorgchem Technology Co., Ltd. | Falling film evaporator |
BRPI0412101A (en) | 2003-07-04 | 2006-08-15 | Nongyue Wang | process for the preparation of 4-aminodiphenylamine |
US8686188B2 (en) | 2003-07-04 | 2014-04-01 | Jiangsu Sinorgchem Technology Co., Ltd. | Process for preparing 4-aminodiphenylamine |
CA2531074C (en) * | 2003-07-04 | 2011-10-11 | Shi, Guangqiang | Process for preparing 4-aminodiphenylamine |
KR100621310B1 (en) * | 2005-05-16 | 2006-09-06 | 금호석유화학 주식회사 | Method for preparing 4-aminodiphenylamine |
JP4876707B2 (en) * | 2006-05-10 | 2012-02-15 | 住友化学株式会社 | Method for producing 4-nitrosodiphenylamine and 4-nitrodiphenylamine |
KR100932208B1 (en) * | 2009-05-21 | 2009-12-16 | 엘아이지넥스원 주식회사 | Sdr apparatus based on sca and method for executing waveform in the apparatus |
CN101717339A (en) * | 2009-12-08 | 2010-06-02 | 江苏扬农化工集团有限公司 | Double quaternary ammonium base compound and preparation method as well as application thereof |
CN101830811B (en) * | 2010-02-23 | 2013-04-03 | 江苏扬农化工集团有限公司 | Preparation method of 4-aminodiphenylamine |
WO2011148976A1 (en) * | 2010-05-26 | 2011-12-01 | 住友化学株式会社 | Method for producing 4-nitrodiphenylamine |
CN102372640A (en) * | 2010-08-20 | 2012-03-14 | 中国石油化工集团公司 | Method for preparing 4-nitrodiphenylamine and 4-nitrosodiphenylamine |
CN102344376B (en) * | 2011-08-17 | 2014-04-02 | 中国石油化工股份有限公司 | Method for preparing p-aminodiphenylamine |
RU2553984C2 (en) * | 2013-02-28 | 2015-06-20 | Олег Александрович ГОДЗОЕВ | Method of obtaining 4-aminodiphenylamine and its alkylated derivatives |
CN103819346B (en) * | 2014-03-17 | 2015-11-04 | 山东尚舜化工有限公司 | A kind of production unit of precursor of 4-ADPA and production technique |
CN108558675A (en) * | 2018-04-25 | 2018-09-21 | 南通理工学院 | A kind of synthetic method of 4-ADPA |
CN111689866A (en) * | 2019-03-15 | 2020-09-22 | 中石化南京化工研究院有限公司 | Preparation method of tower reaction RT base |
RU2706682C1 (en) * | 2019-07-24 | 2019-11-20 | Вахтанг Нодарович Лемонджава | Apparatus for monitoring and regulating the process of defrosting plasma and blood cells |
CN113527111B (en) * | 2020-04-10 | 2023-09-15 | 中国石油化工股份有限公司 | Method for preparing RT (reverse transcription) sauce by normal pressure condensation |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4463191A (en) * | 1983-09-26 | 1984-07-31 | The Goodyear Tire & Rubber Company | Process for the reductive alkylation of aromatic nitro-containing compounds with ketones or aldehydes |
DE3620639A1 (en) * | 1986-06-20 | 1987-12-23 | Bayer Ag | Process for the preparation of 4-nitrodiphenylamines |
US5117063A (en) * | 1991-06-21 | 1992-05-26 | Monsanto Company | Method of preparing 4-aminodiphenylamine |
EP0566783A1 (en) * | 1992-04-21 | 1993-10-27 | Akzo N.V. | Process for the production of nitrodiarylamines |
JPH07149695A (en) * | 1993-09-30 | 1995-06-13 | Seiko Kagaku Kk | Production of 4-aminodiphenylamine |
DE4427249A1 (en) * | 1994-08-02 | 1996-02-08 | Bayer Ag | Process for the preparation of nitro-substituted arylamines |
DE19600722A1 (en) * | 1996-01-11 | 1997-07-17 | Bayer Ag | Process for the preparation of optionally substituted 4-aminodiphenylamines |
US5977411A (en) * | 1997-06-10 | 1999-11-02 | Flexsys America L.P. | Catalytic hydrogeneration of nitrobenzene to 4-aminodiphenylamine in the presence of a hydroxyl compound and a solvent |
SK283209B6 (en) * | 1998-12-11 | 2003-03-04 | Duslo, A. S. | Preparation method for 4-aminodiphenylamine |
KR100298572B1 (en) * | 1999-08-19 | 2001-09-22 | 박찬구 | The method for preparing 4-nitrodiphenylamine and 4-nitrosodiphenylamine from carbanilide |
-
2002
- 2002-07-09 MX MXPA04000665A patent/MXPA04000665A/en active IP Right Grant
- 2002-07-09 EP EP02742396A patent/EP1414782A1/en not_active Withdrawn
- 2002-07-09 AU AU2002315530A patent/AU2002315530B2/en not_active Ceased
- 2002-07-09 RU RU2004105163/04A patent/RU2280640C2/en not_active IP Right Cessation
- 2002-07-09 WO PCT/US2002/021508 patent/WO2003010126A1/en active Application Filing
- 2002-07-09 BR BRPI0211391-0A patent/BR0211391B1/en active IP Right Grant
- 2002-07-09 RS YU3904A patent/RS3904A/en unknown
- 2002-07-09 CN CNB028164474A patent/CN100546972C/en not_active Expired - Lifetime
- 2002-07-09 IL IL15999402A patent/IL159994A0/en unknown
- 2002-07-09 CA CA002454603A patent/CA2454603A1/en not_active Abandoned
- 2002-07-09 PL PL374267A patent/PL206080B1/en unknown
- 2002-07-09 JP JP2003515487A patent/JP4603260B2/en not_active Expired - Lifetime
- 2002-07-09 HU HU0501066A patent/HUP0501066A2/en unknown
- 2002-07-22 TW TW091116246A patent/TWI265919B/en not_active IP Right Cessation
-
2004
- 2004-01-22 NO NO20040292A patent/NO20040292L/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CA2454603A1 (en) | 2003-02-06 |
IL159994A0 (en) | 2004-06-20 |
JP4603260B2 (en) | 2010-12-22 |
RU2280640C2 (en) | 2006-07-27 |
RS3904A (en) | 2006-12-15 |
BR0211391B1 (en) | 2013-05-14 |
NO20040292L (en) | 2004-03-19 |
CN1545497A (en) | 2004-11-10 |
RU2004105163A (en) | 2005-08-10 |
EP1414782A1 (en) | 2004-05-06 |
HUP0501066A2 (en) | 2006-09-28 |
PL374267A1 (en) | 2005-10-03 |
BR0211391A (en) | 2006-05-23 |
CN100546972C (en) | 2009-10-07 |
JP2005515163A (en) | 2005-05-26 |
WO2003010126A1 (en) | 2003-02-06 |
MXPA04000665A (en) | 2004-04-05 |
PL206080B1 (en) | 2010-06-30 |
AU2002315530B2 (en) | 2008-05-22 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Annulment or lapse of patent due to non-payment of fees |