GB1091376A - Substituted diphenylamines - Google Patents
Substituted diphenylaminesInfo
- Publication number
- GB1091376A GB1091376A GB1395866A GB1395866A GB1091376A GB 1091376 A GB1091376 A GB 1091376A GB 1395866 A GB1395866 A GB 1395866A GB 1395866 A GB1395866 A GB 1395866A GB 1091376 A GB1091376 A GB 1091376A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- alkyl
- nitrodiphenylamine
- sec
- carbon atoms
- 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
Links
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical class C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 238000005932 reductive alkylation reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to compounds of the general formula <FORM:1091376/C2/1> in which R is an alkyl group having 1 to 8 carbon atoms or a cyclo alkyl group having 5 to 8 carbon atoms. Compounds claimed per se are 4 - amino - 41 - methylaminodiphenylamine, 4 - amino - 41 - isopropylaminodiphenylamine, 4 - amino - 41 - sec - octylaminodiphenylamine, 4 - amino - 41 - cyclohexylaminodiphenylamine. The compounds may be prepared by formylating the selected N-alkyl or N-cycloalkyl p-phenylene diamine to produce N,N1-diformyl-N alkyl - p - phenylenediamine or N,N1-diformyl - N - cycloalkyl - p - phenylenediamine which is condensed with p-chloronitrobenzene in the presence of alkali-metal carbonate using a polar aprotic solvent such as dimethylformamide. The crude N-alkyl-N-formamido-N1-nitrodiphenylamine or N - cycloalkyl - N-formamido - N1 - nitrodiphenylamine thus produced is subject to ethanolic sodium hydroxide to remove the formyl group, and the resulting N - alkylamino - N1 - nitrodiphenylamine or N - cycloalkylamino - N1 - nitrodiphenylamine is hydrogenated using a suitable hydrogenation catalyst such as palladium-on-carbon to obtain the desired 4-amino-4-alkyl-aminodiphenylamine or the 4-amino-41-cycloalkylaminodiphenylamine. In the case of 4-amino - 41 - sec - alkylaminodiphenyl - amines (in which the alkyl radical has 3 to 8 carbon atoms) and 4 - amino - 41 - cycloalkylaminodiphenylamines (in which the cycloalkyl radical has 5 to 8 carbon atoms), the 4-amino-41-mono-substituted aminodiphenylamines may be prepared by the reductive alkylation of 4,41-diaminodiphenylamine with one equivalent of the appropriate dialkyl ketone or cycloalkanone in an alcohol solvent, in the presence of a hydrogenation catalyst, such as palladium-on-carbon to produce a mixture of the 4-amino-41-sec-alkylaminodiphenylamine and the 4,41-di-sec - alkylaminodiphenylamine, or the 4-amino - 41 - cycloalkylaminodiphenylamine and the 4,41 - dicycloalkylaminodiphenylamine from which the 4-amino-41-mono-substituted aminodiphenylamine may be recovered by distillation or chromatography.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44751565A | 1965-04-12 | 1965-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1091376A true GB1091376A (en) | 1967-11-15 |
Family
ID=23776685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1395866A Expired GB1091376A (en) | 1965-04-12 | 1966-03-29 | Substituted diphenylamines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1091376A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2015997A (en) * | 1978-03-13 | 1979-09-19 | Monsanto Co | Production of nitrodiarylamines |
| RU2502725C1 (en) * | 2012-10-22 | 2013-12-27 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Method of producing n-alkyl-n'-phenyl-para-phenylenediamines |
| US8759587B2 (en) | 2010-12-21 | 2014-06-24 | Korea Kumho Petrochemical Co., Ltd. | Method for preparation of 4,4′-dinitrodiphenylamine and 4,4′-bis(alkylamino)diphenylamine by using 4-nitroaniline |
| US8835687B2 (en) | 2010-12-21 | 2014-09-16 | Korea Kumho Petrochemical Co., Ltd. | Method for preparation of 4,4′-dinitrodiphenylamine and 4,4′-bis(alkylamino)diphenylamine with the base catalyst complex |
| CN119661376A (en) * | 2024-12-06 | 2025-03-21 | 山东阳谷华泰化工股份有限公司 | Migration-resistant anti-aging agent, and preparation method and application thereof |
-
1966
- 1966-03-29 GB GB1395866A patent/GB1091376A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2015997A (en) * | 1978-03-13 | 1979-09-19 | Monsanto Co | Production of nitrodiarylamines |
| US8759587B2 (en) | 2010-12-21 | 2014-06-24 | Korea Kumho Petrochemical Co., Ltd. | Method for preparation of 4,4′-dinitrodiphenylamine and 4,4′-bis(alkylamino)diphenylamine by using 4-nitroaniline |
| US8835687B2 (en) | 2010-12-21 | 2014-09-16 | Korea Kumho Petrochemical Co., Ltd. | Method for preparation of 4,4′-dinitrodiphenylamine and 4,4′-bis(alkylamino)diphenylamine with the base catalyst complex |
| RU2502725C1 (en) * | 2012-10-22 | 2013-12-27 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Method of producing n-alkyl-n'-phenyl-para-phenylenediamines |
| CN119661376A (en) * | 2024-12-06 | 2025-03-21 | 山东阳谷华泰化工股份有限公司 | Migration-resistant anti-aging agent, and preparation method and application thereof |
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