GB1091376A - Substituted diphenylamines - Google Patents

Substituted diphenylamines

Info

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
cycloalkyl
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
Application number
GB1395866A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Uniroyal Inc
Original Assignee
Uniroyal Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to US44751565A priority Critical
Application filed by Uniroyal Inc filed Critical Uniroyal Inc
Publication of GB1091376A publication Critical patent/GB1091376A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02Amines; Quaternary ammonium compounds
    • A01N33/06Nitrogen directly attached to an aromatic ring system

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.
GB1395866A 1965-04-12 1966-03-29 Substituted diphenylamines Expired GB1091376A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US44751565A true 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 (4)

* Cited by examiner, † Cited by third party
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

Cited By (4)

* Cited by examiner, † Cited by third party
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

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