IN2014KN01593A - - Google Patents
Info
- Publication number
- IN2014KN01593A IN2014KN01593A IN1593KON2014A IN2014KN01593A IN 2014KN01593 A IN2014KN01593 A IN 2014KN01593A IN 1593KON2014 A IN1593KON2014 A IN 1593KON2014A IN 2014KN01593 A IN2014KN01593 A IN 2014KN01593A
- Authority
- IN
- India
- Prior art keywords
- adpa
- coupling
- recovery
- azobenzene
- hydrogenation
- Prior art date
Links
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005191 phase separation Methods 0.000 abstract 1
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
- C07C209/02—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of hydrogen atoms by amino 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing 4 aminodiphenylamine (4 ADPA) comprising steps of coupling of aniline with nitrobenzene in presence of a suitable base e.g. tetramethylammonium hydroxide (TMAH) hydrogenation of the coupling mass phase separation hydrogenation of azobenzene in the separated organic mass and fractional distillation for 4 ADPA recovery. An improvement in 4 ADPA recovery and a lowering of tar formation are obtained due to azobenzene reduction prior to 4 ADPA isolation. Also a gain in volume productivity of 4 ADPA is obtained by suitably altering the batch cycle time of the coupling reaction.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IB2012/051059 WO2013132290A2 (en) | 2012-03-07 | 2012-03-07 | Improved process for preparing 4-aminodiphenylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IN2014KN01593A true IN2014KN01593A (en) | 2015-10-23 |
Family
ID=49117447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IN1593KON2014 IN2014KN01593A (en) | 2012-03-07 | 2012-03-07 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US9708243B2 (en) |
| IN (1) | IN2014KN01593A (en) |
| WO (1) | WO2013132290A2 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105585507B (en) * | 2014-11-13 | 2019-04-30 | 江苏圣奥化学科技有限公司 | The preparation method of 4-aminodiphenylamine |
| CN106554286B (en) * | 2015-09-29 | 2018-09-25 | 中国石油化工集团公司 | A kind of method that noble metal catalyst continuously prepares p phenylenediamine type antioxidant |
| CN106242978B (en) * | 2016-07-28 | 2018-08-31 | 南京工业大学 | Method for preparing antioxidant 6PPD by using micro-reaction device |
| CN106867556B (en) * | 2017-03-01 | 2019-10-22 | 西北大学 | A coal tar fraction separation process and device |
| CN108558675A (en) * | 2018-04-25 | 2018-09-21 | 南通理工学院 | Synthesis method of 4-aminodiphenylamine |
| CN109232275B (en) * | 2018-10-26 | 2021-06-11 | 科迈化工股份有限公司 | Preparation method of 4-nitrodiphenylamine and 4-nitrosodiphenylamine |
| DE102020212508A1 (en) | 2020-10-02 | 2022-04-07 | Continental Reifen Deutschland Gmbh | Compound, rubber mixture containing the compound, vehicle tire which has the rubber mixture in at least one component, method for producing the compound and use of the compound as an aging inhibitor and/or antioxidant and/or antiozonant and/or colorant |
| CN114539074B (en) * | 2022-03-02 | 2024-06-11 | 山东阳谷华泰化工股份有限公司 | Refining method of N-alkyl-p-phenylenediamine |
| CN117263811B (en) * | 2022-06-15 | 2025-12-16 | 中国石油化工股份有限公司 | A method for recovering aniline tar |
| US20240117149A1 (en) * | 2022-09-28 | 2024-04-11 | The Goodyear Tire & Rubber Company | Rubber - forming additives from end of life tires through syngas production |
| US20240124683A1 (en) | 2022-09-28 | 2024-04-18 | The Goodyear Tire & Rubber Company | Rubber - forming additives from biomass through syngas production |
| CN116554038B (en) * | 2022-11-10 | 2024-04-12 | 圣奥化学科技有限公司 | Polyalkyl p-phenylenediamine antioxidant, intermediates thereof and preparation method |
| US20250163236A1 (en) | 2023-11-21 | 2025-05-22 | The Goodyear Tire & Rubber Company | Production of rubber compositions from end of life tires |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2633811C2 (en) | 1976-07-28 | 1983-11-10 | Bayer Ag, 5090 Leverkusen | Process for the preparation of nitrodiphenylamines |
| US4187248A (en) | 1977-11-23 | 1980-02-05 | Monsanto Company | Making a nitrodiarylamine by reacting an alkali metal salt of a formamide with a nitrohaloarene |
| US4187249A (en) | 1977-12-27 | 1980-02-05 | Monsanto Company | Promoting the reaction of sodium salts of formyl derivatives of aromatic amines to form nitrodiarylamines |
| US4209463A (en) | 1977-12-27 | 1980-06-24 | Monsanto Company | Promoting the formation of nitrodiarylamines from nitrohaloarenes, activated aryl amines and sodium carbonates |
| US4140716A (en) | 1978-01-05 | 1979-02-20 | Monsanto Company | Process for making an amide of formic acid and forming nitrodiarylamine therefrom |
| US4155936A (en) | 1978-03-08 | 1979-05-22 | The Goodyear Tire & Rubber Company | Para-nitrodiphenylamines synthesis using Polyethers and macrocyclic esters as solubilizing agents |
| US4196146A (en) | 1978-03-13 | 1980-04-01 | Monsanto Company | Making nitrodiarylamines from formyl derivatives of aromatic amines and nitrohaloarenes by admixing with certain aqueous salt solutions |
| US4518803A (en) | 1982-09-30 | 1985-05-21 | Uniroyal, Inc. | Process for the preparation of p-nitrosodiphenylamine |
| US4479008A (en) | 1982-09-30 | 1984-10-23 | Uniroyal, Inc. | Preparation of p-nitrosodiphenylamine |
| US4614817A (en) | 1983-12-19 | 1986-09-30 | Monsanto Company | Making nitrodiarylamines |
| DE3504479A1 (en) | 1985-02-09 | 1986-08-14 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING 4-NITRODIPHENYLAMINE |
| US4683332A (en) | 1985-05-20 | 1987-07-28 | The Goodyear Tire & Rubber Company | Para-nitrodiphenylamine synthesis |
| US5117063A (en) | 1991-06-21 | 1992-05-26 | Monsanto Company | Method of preparing 4-aminodiphenylamine |
| DE19600722A1 (en) | 1996-01-11 | 1997-07-17 | Bayer Ag | Process for the preparation of optionally substituted 4-aminodiphenylamines |
| TW451284B (en) | 1996-10-15 | 2001-08-21 | Semiconductor Energy Lab | Semiconductor device and method of manufacturing the same |
| 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 |
| US6140538A (en) | 1998-05-18 | 2000-10-31 | Flexsys America L.P. | Process for preparing 4-aminodiphenylamines |
| US6495723B1 (en) | 2000-06-21 | 2002-12-17 | Flexsys America | Zeolite support loaded with a base material for use in the coupling of aniline and nitrobenzene |
| US6770189B2 (en) | 2000-10-27 | 2004-08-03 | Flexsys B.V. | Process for improving the purity of quaternary ammonium hydroxides by electrolysis |
| DE10055221A1 (en) | 2000-11-08 | 2002-05-29 | Bayer Ag | Preparation of 4-aminodiphenylamine involves hydrogenating nitrosobenzene with hydrogen in the presence of proton catalyst and hydrogenation catalyst |
| 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 |
| WO2005003078A1 (en) | 2003-07-04 | 2005-01-13 | Shi, Guangqiang | A process for preparing 4-aminodiphenylamine |
| CA2531074C (en) | 2003-07-04 | 2011-10-11 | Shi, Guangqiang | Process for preparing 4-aminodiphenylamine |
-
2012
- 2012-03-07 IN IN1593KON2014 patent/IN2014KN01593A/en unknown
- 2012-03-07 US US14/383,182 patent/US9708243B2/en active Active
- 2012-03-07 WO PCT/IB2012/051059 patent/WO2013132290A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20150045584A1 (en) | 2015-02-12 |
| WO2013132290A2 (en) | 2013-09-12 |
| WO2013132290A3 (en) | 2015-08-06 |
| US9708243B2 (en) | 2017-07-18 |
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