BR9916054A - Método de preparação de 4-aminodifenilamina - Google Patents
Método de preparação de 4-aminodifenilaminaInfo
- Publication number
- BR9916054A BR9916054A BR9916054-4A BR9916054A BR9916054A BR 9916054 A BR9916054 A BR 9916054A BR 9916054 A BR9916054 A BR 9916054A BR 9916054 A BR9916054 A BR 9916054A
- Authority
- BR
- Brazil
- Prior art keywords
- reaction
- nitrodiphenylamine
- nitrosodiphenylamine
- aniline
- nitrobenzene
- 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
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/38—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 nitroso 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
<B>"MéTODO DE PREPARAçãO DE 4-AMINODIFENILAMINA"<D>. A presente invenção se refere a um método de preparação de 4-aminodifenilamina, através de uma preparação intermediária de 4-nitrodifenilamina e/ou 4-nitrosodifenilamina e/ou seus sais, através da reação de anilina com nitrobenzeno em um meio líquido, a uma temperatura entre 50 e 130°C, sob pressão normal ou pressão reduzida, em uma atmosfera inerte na presença de oxigênio do ar, com subsequente hidrogenação do intermediário de 4-nitrodifenilamina e/ou 4-nitrosodifenilamina e produtos colaterais e pelo isolamento da 4-aminodifenilamina e produtos colaterais e recirculação de matérias-primas não convertidas. A reação da anilina com o nitrobenzeno, com seletividade de pelo menos 50% de 4-nitrodifenilamina e nitrosodifenilamina, é realizada em um sistema reacional, consistindo de uma solução de sais de verdadeiros zwiteríons com hidróxidos de fórmula geral: HO^ -^/ (R^ 1^R^ 2^R^ 3^)N^ +^-CHR^ 4^-(CH~ 2~)~ x~-Y^ -^/Z^ +^ onde R^ 1^ e R^ 2^ significam metila a dodecila; R^ 3^ significa metila, etila, fenila ou benzila; R~ 4~ significa hidrogênio ou metila; X significa um inteiro de 0 a 5; Y^ -^ significa CO~ 2~^ -^, SO~ 3~^ -^; e Z^ +^ significa um cátion de um metal alcalino, Li, Na, K, Cs ou um cátion de amónio quaternário tetra-substituído, como tetrametilamónio ou suas combinações mútuas, em que surgem os compostos de 4-nitrosodifenilamina e/ou 4-nitrodifenilamina e/ou seus sais, que produzem após a hidrogenação o composto de 4-ADFA e após a reação pelo menos metade do sistema reacional é usado novamente para a reação seguinte e/ou é reciclado. O meio de reação é formado separadamente e/ou será formado in situ no sistema reacional proveniente das matérias-primas. O meio líquido para a reação da anilina com o nitrobenzeno é formado de água e/ou pelo menos um composto orgânico, escolhido dentre anilina, piridina, tolueno, xileno, ciclohexano e álcoois alifáticos, tendo o número de átomos de carbono de 1 a 4 na molécula.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK1714-98A SK283209B6 (sk) | 1998-12-11 | 1998-12-11 | Spôsob prípravy 4-aminodifenylamínu |
| PCT/SK1999/000010 WO2000035853A1 (en) | 1998-12-11 | 1999-04-29 | Method of preparation of 4-aminodiphenylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR9916054A true BR9916054A (pt) | 2001-09-04 |
| BR9916054B1 BR9916054B1 (pt) | 2009-08-11 |
Family
ID=20434774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI9916054-4A BR9916054B1 (pt) | 1998-12-11 | 1999-04-29 | método de preparação de 4-aminodifenilamina. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6388136B1 (pt) |
| EP (1) | EP1137624B1 (pt) |
| JP (1) | JP2002532455A (pt) |
| KR (1) | KR100478688B1 (pt) |
| CN (1) | CN1191229C (pt) |
| AT (1) | ATE257146T1 (pt) |
| AU (1) | AU762752B2 (pt) |
| BR (1) | BR9916054B1 (pt) |
| CA (1) | CA2354129C (pt) |
| CZ (1) | CZ298635B6 (pt) |
| DE (1) | DE69913989T2 (pt) |
| ES (1) | ES2214031T3 (pt) |
| ID (1) | ID29355A (pt) |
| IL (1) | IL143518A (pt) |
| MX (1) | MXPA01005881A (pt) |
| MY (1) | MY125604A (pt) |
| PL (1) | PL194052B1 (pt) |
| RU (1) | RU2224741C2 (pt) |
| SK (1) | SK283209B6 (pt) |
| UA (1) | UA56354C2 (pt) |
| WO (1) | WO2000035853A1 (pt) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5117063A (en) † | 1991-06-21 | 1992-05-26 | Monsanto Company | Method of preparing 4-aminodiphenylamine |
| SK283209B6 (sk) * | 1998-12-11 | 2003-03-04 | Duslo, A. S. | Spôsob prípravy 4-aminodifenylamínu |
| IL159994A0 (en) * | 2001-07-23 | 2004-06-20 | Flexsys America Lp | Process for preparing 4-aminodiphenylamine |
| US6395933B1 (en) * | 2001-07-23 | 2002-05-28 | Flexsys America, L.P. | Process for preparing 4-aminodiphenylamine intermediates |
| KR100899661B1 (ko) * | 2002-10-22 | 2009-05-27 | 엘지디스플레이 주식회사 | 반투과형 액정표시장치 |
| US7183439B2 (en) * | 2002-12-10 | 2007-02-27 | Flexsys America L.P. | Process for preparing 4-aminodiphenylamine intermediates |
| KR100612922B1 (ko) | 2003-07-04 | 2006-08-14 | 농유 왕 | 4-아미노 디페닐아민의 제조방법 |
| US8686188B2 (en) | 2003-07-04 | 2014-04-01 | Jiangsu Sinorgchem Technology Co., Ltd. | Process for preparing 4-aminodiphenylamine |
| US8486223B2 (en) * | 2003-07-04 | 2013-07-16 | Jiangsu Sinorgchem Technology Co., Ltd. | Falling film evaporator |
| JP4546958B2 (ja) * | 2003-07-04 | 2010-09-22 | チアンス・シノケム・テクノロジー・カンパニー・リミテッド | ４−アミノジフェニルアミンの製造方法 |
| KR100621310B1 (ko) | 2005-05-16 | 2006-09-06 | 금호석유화학 주식회사 | 4-아미노디페닐아민의 제조방법 |
| CN100363330C (zh) * | 2005-05-20 | 2008-01-23 | 中国石油天然气集团公司 | 一种提高4-氨基二苯胺产率的方法 |
| US7683017B2 (en) * | 2007-06-20 | 2010-03-23 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine |
| CN102259029B (zh) | 2010-05-24 | 2014-12-10 | 江苏圣奥化学科技有限公司 | 固体碱催化剂 |
| CN102372640A (zh) * | 2010-08-20 | 2012-03-14 | 中国石油化工集团公司 | 一种制备4-硝基二苯胺和4-亚硝基二苯胺的方法 |
| RU2553984C2 (ru) * | 2013-02-28 | 2015-06-20 | Олег Александрович ГОДЗОЕВ | Способ получения 4-аминодифениламина и его алкилированных производных |
| CN109734606B (zh) * | 2019-02-27 | 2021-09-03 | 青岛科技大学 | 一种延长芳胺类抗氧剂制备用加氢催化剂寿命的方法 |
| CN113527111B (zh) * | 2020-04-10 | 2023-09-15 | 中国石油化工股份有限公司 | 一种常压缩合制备rt培司的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB713622A (en) * | 1951-12-05 | 1954-08-11 | Du Pont | Process for the preparation of aromatic parahydroxyamines |
| US5117063A (en) * | 1991-06-21 | 1992-05-26 | Monsanto Company | Method of preparing 4-aminodiphenylamine |
| US5252737A (en) * | 1992-05-22 | 1993-10-12 | Monsanto Company | Process for preparing N-aliphatic substituted p-phenylenediamines |
| US5451702A (en) * | 1993-04-26 | 1995-09-19 | Monsanto Company | Process for preparing substituted aromatic amines |
| DE19600722A1 (de) | 1996-01-11 | 1997-07-17 | Bayer Ag | Verfahren zur Herstellung von gegebenenfalls substituierten 4-Aminodiphenylaminen |
| SK283209B6 (sk) * | 1998-12-11 | 2003-03-04 | Duslo, A. S. | Spôsob prípravy 4-aminodifenylamínu |
-
1998
- 1998-12-11 SK SK1714-98A patent/SK283209B6/sk not_active IP Right Cessation
-
1999
- 1999-04-29 DE DE69913989T patent/DE69913989T2/de not_active Expired - Lifetime
- 1999-04-29 AU AU41796/99A patent/AU762752B2/en not_active Ceased
- 1999-04-29 ES ES99925539T patent/ES2214031T3/es not_active Expired - Lifetime
- 1999-04-29 IL IL14351899A patent/IL143518A/en not_active IP Right Cessation
- 1999-04-29 PL PL99348867A patent/PL194052B1/pl unknown
- 1999-04-29 BR BRPI9916054-4A patent/BR9916054B1/pt not_active IP Right Cessation
- 1999-04-29 CN CNB998143383A patent/CN1191229C/zh not_active Expired - Fee Related
- 1999-04-29 WO PCT/SK1999/000010 patent/WO2000035853A1/en active IP Right Grant
- 1999-04-29 EP EP99925539A patent/EP1137624B1/en not_active Expired - Lifetime
- 1999-04-29 CA CA002354129A patent/CA2354129C/en not_active Expired - Fee Related
- 1999-04-29 CZ CZ20011989A patent/CZ298635B6/cs not_active IP Right Cessation
- 1999-04-29 KR KR10-2001-7007196A patent/KR100478688B1/ko not_active IP Right Cessation
- 1999-04-29 JP JP2000588115A patent/JP2002532455A/ja active Pending
- 1999-04-29 ID IDW00200101227A patent/ID29355A/id unknown
- 1999-04-29 UA UA2001074858A patent/UA56354C2/uk unknown
- 1999-04-29 AT AT99925539T patent/ATE257146T1/de not_active IP Right Cessation
- 1999-04-29 MX MXPA01005881A patent/MXPA01005881A/es not_active IP Right Cessation
- 1999-04-29 RU RU2001119068/04A patent/RU2224741C2/ru not_active IP Right Cessation
-
2001
- 2001-06-06 MY MYPI20012642A patent/MY125604A/en unknown
- 2001-06-08 US US09/875,881 patent/US6388136B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL348867A1 (en) | 2002-06-17 |
| MY125604A (en) | 2006-08-30 |
| CZ298635B6 (cs) | 2007-12-05 |
| ID29355A (id) | 2001-08-23 |
| DE69913989T2 (de) | 2004-12-09 |
| EP1137624B1 (en) | 2004-01-02 |
| ES2214031T3 (es) | 2004-09-01 |
| SK283209B6 (sk) | 2003-03-04 |
| AU762752B2 (en) | 2003-07-03 |
| MXPA01005881A (es) | 2003-07-21 |
| KR100478688B1 (ko) | 2005-03-24 |
| DE69913989D1 (de) | 2004-02-05 |
| US6388136B1 (en) | 2002-05-14 |
| RU2224741C2 (ru) | 2004-02-27 |
| ATE257146T1 (de) | 2004-01-15 |
| CA2354129C (en) | 2009-01-06 |
| IL143518A (en) | 2004-12-15 |
| CA2354129A1 (en) | 2000-06-22 |
| US20020045779A1 (en) | 2002-04-18 |
| KR20010082330A (ko) | 2001-08-29 |
| JP2002532455A (ja) | 2002-10-02 |
| BR9916054B1 (pt) | 2009-08-11 |
| EP1137624A1 (en) | 2001-10-04 |
| WO2000035853A1 (en) | 2000-06-22 |
| UA56354C2 (uk) | 2003-05-15 |
| AU4179699A (en) | 2000-07-03 |
| CZ20011989A3 (cs) | 2001-11-14 |
| PL194052B1 (pl) | 2007-04-30 |
| CN1191229C (zh) | 2005-03-02 |
| CN1330627A (zh) | 2002-01-09 |
| SK171498A3 (en) | 2000-07-11 |
| IL143518A0 (en) | 2002-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B25A | Requested transfer of rights approved |
Owner name: AVION INVEST, A.S. (SK) Free format text: TRANSFERIDO POR FUSAO DE: DUSLO, A.S. |
|
| B25D | Requested change of name of applicant approved |
Owner name: DUSLO, A.S. (SK) Free format text: ALTERADO DE: AVION INVEST, A.S. |
|
| B25G | Requested change of headquarter approved |
Owner name: DUSLO, A.S. (SK) Free format text: SEDE ALTERADA CONFORME SOLICIADO NA PETICAO NO 020070147781/RJ DE 19/10/2007. |
|
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 10 (DEZ) ANOS CONTADOS A PARTIR DE 22/09/2009, OBSERVADAS AS CONDICOES LEGAIS. |
|
| B24C | Patent annual fee: request for for restoration |
Free format text: REFERENTE A 13A ANUIDADE(S), CONFORME ART.87 DA LPI 9.279. |
|
| B24H | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi) | ||
| B24F | Patent annual fee: publication cancelled |
Free format text: ANULADA A PUBLICACAO CODIGO 24.8 NA RPI NO 2259 DE 22/04/2014 POR TER SIDO INDEVIDA. |
|
| B21F | Lapse acc. art. 78, item iv - on non-payment of the annual fees in time |
Free format text: REFERENTE A 13A ANUIDADE. |
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| B24J | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12) |
Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2607 DE 22-12-2020 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |