GB414574A - A catalytic process for the manufacture of nuclear substituted aromatic amines - Google Patents

A catalytic process for the manufacture of nuclear substituted aromatic amines

Info

Publication number
GB414574A
GB414574A GB35993/33A GB3599333A GB414574A GB 414574 A GB414574 A GB 414574A GB 35993/33 A GB35993/33 A GB 35993/33A GB 3599333 A GB3599333 A GB 3599333A GB 414574 A GB414574 A GB 414574A
Authority
GB
United Kingdom
Prior art keywords
aniline
cyclohexene
cyclohexyl
substituted
toluidine
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
GB35993/33A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB414574A publication Critical patent/GB414574A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Nuclear-substituted aromatic amines are obtained by heating a primary amine with an aliphatic or cycloaliphatic alcohol or olefine in the presence of a non-metallic catalyst having no basic character. A mixture of C-substituted and N-substituted amines is formed from which the former is separated. The formation of the nuclear - substituted product is favoured by heating with exclusion of water and removal of any water formed. The preferred catalyst is a hydrosilicate of large surface area and the reaction temperature may be 200--270 DEG C. Examples describe the production of (1) o-cyclohexyl aniline from aniline and cyclohexene; (2) p-methyl-o-cyclohexyl aniline from p-toluidine and cyclohexene; (3) cyclohexyl aniline from cyclohexanol and aniline; (4) butyl aniline from butyl alcohol and aniline; (5) a mixture of primary and secondary bases from m-toluidine and methyl-cyclohexene; (6) vic.-1-cyclohexyl-2-amino-3-methylbenzene from o-toluidine and cyclohexene.
GB35993/33A 1932-12-22 1933-12-21 A catalytic process for the manufacture of nuclear substituted aromatic amines Expired GB414574A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE414574X 1932-12-22

Publications (1)

Publication Number Publication Date
GB414574A true GB414574A (en) 1934-08-09

Family

ID=6448361

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35993/33A Expired GB414574A (en) 1932-12-22 1933-12-21 A catalytic process for the manufacture of nuclear substituted aromatic amines

Country Status (1)

Country Link
GB (1) GB414574A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2984687A (en) * 1956-04-27 1961-05-16 Standard Oil Co Catalytic process for n-alkylation of amines
US4760184A (en) * 1986-05-12 1988-07-26 Air Products And Chemicals, Inc. Alkylation of aromatic amines in the presence of non-zeolitic molecular sieves
US4851579A (en) * 1987-04-07 1989-07-25 Air Products And Chemicals, Inc. Alkylation of aromatic amines over Al exchanged zeolites
US4876377A (en) * 1985-11-08 1989-10-24 Air Products And Chemicals, Inc. Alkylation of aromatic amines with olefins on partially dealuminated zeolites
US4914237A (en) * 1988-11-29 1990-04-03 Air Products And Chemicals, Inc. Alkylation of toluenediamine and para-phenylenediamine with isobutylene in the presence of acidic, crystalline molecular sieves
US4967001A (en) * 1988-06-30 1990-10-30 Air Products And Chemicals, Inc. Alkylation of toluenediamine and para-phenylenediamine with isobutylene in the presence of acidic, crystalline molecular sieves
US5068435A (en) * 1985-11-08 1991-11-26 Air Products And Chemicals, Inc. Ortho-alkylated aromatic amines via gamma alumina catalyst
EP0807620A1 (en) * 1996-05-17 1997-11-19 The Lubrizol Corporation Alkylation of aromatic amines using a heteropoly acid catalyst

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2984687A (en) * 1956-04-27 1961-05-16 Standard Oil Co Catalytic process for n-alkylation of amines
US4876377A (en) * 1985-11-08 1989-10-24 Air Products And Chemicals, Inc. Alkylation of aromatic amines with olefins on partially dealuminated zeolites
US5068435A (en) * 1985-11-08 1991-11-26 Air Products And Chemicals, Inc. Ortho-alkylated aromatic amines via gamma alumina catalyst
US4760184A (en) * 1986-05-12 1988-07-26 Air Products And Chemicals, Inc. Alkylation of aromatic amines in the presence of non-zeolitic molecular sieves
US4851579A (en) * 1987-04-07 1989-07-25 Air Products And Chemicals, Inc. Alkylation of aromatic amines over Al exchanged zeolites
US4967001A (en) * 1988-06-30 1990-10-30 Air Products And Chemicals, Inc. Alkylation of toluenediamine and para-phenylenediamine with isobutylene in the presence of acidic, crystalline molecular sieves
US4914237A (en) * 1988-11-29 1990-04-03 Air Products And Chemicals, Inc. Alkylation of toluenediamine and para-phenylenediamine with isobutylene in the presence of acidic, crystalline molecular sieves
EP0807620A1 (en) * 1996-05-17 1997-11-19 The Lubrizol Corporation Alkylation of aromatic amines using a heteropoly acid catalyst
US5817831A (en) * 1996-05-17 1998-10-06 The Lubrizol Corporation Alkylation of aromatic amines using a heterpoly catalyst

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