GB1462254A - Alkylation of aromatic amines - Google Patents

Alkylation of aromatic amines

Info

Publication number
GB1462254A
GB1462254A GB2336174A GB2336174A GB1462254A GB 1462254 A GB1462254 A GB 1462254A GB 2336174 A GB2336174 A GB 2336174A GB 2336174 A GB2336174 A GB 2336174A GB 1462254 A GB1462254 A GB 1462254A
Authority
GB
United Kingdom
Prior art keywords
reaction
ring
prepared
amines
aluminium
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
GB2336174A
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.)
Ethyl Corp
Original Assignee
Ethyl Corp
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 claimed from US05/449,837 external-priority patent/US4128582A/en
Application filed by Ethyl Corp filed Critical Ethyl Corp
Publication of GB1462254A publication Critical patent/GB1462254A/en
Expired legal-status Critical Current

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
    • C07C209/68—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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/24—Nitrogen compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0252—Nitrogen containing compounds with a metal-nitrogen link, e.g. metal amides, metal guanidides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/22—Halogenating

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Aromatic amines which are substituted on the ring by one or more optionally substituted aliphatic or cycloaliphatic hydrocarbon radicals are prepared by reacting an aromatic amine having at least one unsubstituted ortho-position on the ring and at least one hydrogen atom bonded to the amine nitrogen atom with one or more aliphatic or cycloaliphatic hydrocarbons which contain at least one olefinic double bond and which may contain substituents which do not affect the reaction. This reaction is carried out at a temperature from 200 to 500 DEG C in the presence of a catalyst formed by reaction of aluminium or an alkylaluminium compound with an aromatic amine. The essential feature of the process is that hydrogen halide is added to the reaction mixture in such amounts that up to two halogen atoms are obtained per aluminium atom in the mixture. The amines prepared are valuable intermediates for the preparation of dyes, and are used for the synthesis of various selective herbicides.
GB2336174A 1973-06-04 1974-05-24 Alkylation of aromatic amines Expired GB1462254A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36599673A 1973-06-04 1973-06-04
US05/449,837 US4128582A (en) 1973-06-04 1974-03-11 Chemical process

Publications (1)

Publication Number Publication Date
GB1462254A true GB1462254A (en) 1977-01-19

Family

ID=27003190

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2336174A Expired GB1462254A (en) 1973-06-04 1974-05-24 Alkylation of aromatic amines

Country Status (9)

Country Link
JP (1) JPS5516414B2 (en)
CA (1) CA1013769A (en)
CH (1) CH609032A5 (en)
DE (1) DE2426395C3 (en)
ES (1) ES427156A1 (en)
FR (1) FR2231664B1 (en)
GB (1) GB1462254A (en)
IT (1) IT1013330B (en)
NL (1) NL179814C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006130498A1 (en) * 2005-06-02 2006-12-07 Albemarle Corporation Improved process for synthesizing alkylated arylamines
WO2009029383A1 (en) 2007-08-30 2009-03-05 Albermarle Corporation Preparation of 2-(1,3-dimethylbutyl)aniline and other branched alkyl-substituted-anilines

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5355729A (en) * 1976-11-01 1978-05-20 Shinko Electric Co Ltd Torque direction switching circuit
JPS58163842U (en) * 1982-04-28 1983-10-31 東洋紡績株式会社 clothing pressure measurement device
JPS5984442U (en) * 1982-06-21 1984-06-07 山根　和枝 contact thermometer
JPS6025427A (en) * 1983-07-22 1985-02-08 Keisuke Honda Electronic device for measuring body temperature
JPS6029248U (en) * 1983-08-03 1985-02-27 川崎製鉄株式会社 Furnace shell temperature measuring device
JPS63133028A (en) * 1986-11-26 1988-06-04 Terumo Corp Electronic thermometer
US5124483A (en) * 1989-10-10 1992-06-23 The Dow Chemical Company Ortho-alkylation of aromatic amines
US5103059A (en) * 1990-10-23 1992-04-07 Ethyl Corporation Process for alkylation of aromatic diamines

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2814646A (en) * 1954-04-29 1957-11-26 Ethyl Corp Amine alkylation using aluminum anilide catalyst
DE1044097B (en) * 1955-01-22 1958-11-20 Bayer Ag Process for the preparation of ring-alkylated aromatic amines
DE1051271B (en) * 1955-01-22 1959-02-26 Bayer Ag Process for the preparation of ring-alkylated aromatic amines
DE1056138B (en) * 1955-01-22 1959-04-30 Bayer Ag Process for the preparation of ring-alkylated aromatic amines
DE1048277B (en) * 1955-01-22 1959-01-08 Bayer Ag Process for the preparation of ring-alkylated aromatic amines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006130498A1 (en) * 2005-06-02 2006-12-07 Albemarle Corporation Improved process for synthesizing alkylated arylamines
WO2009029383A1 (en) 2007-08-30 2009-03-05 Albermarle Corporation Preparation of 2-(1,3-dimethylbutyl)aniline and other branched alkyl-substituted-anilines
US8236988B2 (en) 2007-08-30 2012-08-07 Albemarle Corporation Preparation of 2-(1,3-dimethylbutyl)aniline and other branched alkyl-substituted-anilines

Also Published As

Publication number Publication date
IT1013330B (en) 1977-03-30
NL179814B (en) 1986-06-16
JPS5516414B2 (en) 1980-05-01
CH609032A5 (en) 1979-02-15
DE2426395C3 (en) 1984-05-30
ES427156A1 (en) 1976-12-01
NL7407527A (en) 1974-12-06
NL179814C (en) 1986-11-17
DE2426395A1 (en) 1974-12-12
CA1013769A (en) 1977-07-12
AU6967174A (en) 1975-12-04
JPS5019726A (en) 1975-03-01
FR2231664B1 (en) 1978-01-20
FR2231664A1 (en) 1974-12-27
DE2426395B2 (en) 1978-10-05

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19920524