GB1462254A - Alkylation of aromatic amines - Google Patents
Alkylation of aromatic aminesInfo
- 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
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.
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)
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)
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)
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 |
-
1974
- 1974-05-24 GB GB2336174A patent/GB1462254A/en not_active Expired
- 1974-05-28 CA CA201,067A patent/CA1013769A/en not_active Expired
- 1974-05-28 FR FR7418428A patent/FR2231664B1/fr not_active Expired
- 1974-05-31 ES ES427156A patent/ES427156A1/en not_active Expired
- 1974-05-31 IT IT5133574A patent/IT1013330B/en active
- 1974-05-31 DE DE19742426395 patent/DE2426395C3/en not_active Expired
- 1974-06-04 NL NL7407527A patent/NL179814C/en not_active IP Right Cessation
- 1974-06-04 CH CH759474A patent/CH609032A5/en not_active IP Right Cessation
- 1974-06-04 JP JP6330174A patent/JPS5516414B2/ja not_active Expired
Cited By (3)
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 |