US3923892A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Aromatic amine alkylation
Assignee: Ethyl Corp
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Filing: 1974-03-25
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Granted: 1975-12-02
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Expires: 1994-03-25
Abstract
Abstract Aromatic amines having a hydrogen atom on at least one nuclear carbon atom ortho to an amine group (e.g., aniline) are selectively orthoalkylated by adding a catalytic amount of an alkyl aluminum halide such as diethyl aluminum chloride to the aromatic amine and then heating the resultant mixture to about 100*-500*C in the presence of an olefin. The process may also be carried out in the added presence of an aluminum anilide.
Inventors
- 👤 Osakar E H Klopfer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:30
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/68
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
112 words
IN A PROCESS FOR ALKYLATING AN AROMATIC AMINE SELECTIVELY IN A NUCLEAR POSITION ORTHO TO THE AMINE GROUP, SAID AROMATIC AMINE HAVING AT LEAST ONE HYDROGEN ATOM BONDED TO SAID AMINE GROUP AND HAVING AT LEAST ONE NUCLEAR POSITION ORTHO TO SAID AMINE GROUP UNSUBSTITUTED EXCEPT FOR HYDROGEN, SAID PROCESS COMPRISING REACTING SAID AROMATIC AMINE WITH AN OLEFIN HYDROCARBON AT A TEMPERATURE OF ABOUT 200*-400*C IN THE PRESENCE OF AN ALUMINUM ANILIDE CATALYST, THE IMPROVEMENT FORMING SAID ALUMINUM ANILIDE CATALYST BY ADDING AN ALKYL ALUMINUM HALIDE TO SAID AROMATIC AMINE, SAID IMPROVEMENT RESULTING IN AN ALKYLATION RATE IN EXCESS OF THAT OBTAINED UNDER THE SAME CONDITIONS USING A NON-HALOGEN ALUMINUM ANILIDE CATALYST.
Claim 2
Dependent Claim
112 words
IN A PROCESS FOR ALKYLATING AN AROMATIC AMINE SELECTIVELY IN A NUCLEAR POSITION ORTHO TO THE AMINE GROUP, SAID AROMATIC AMINE HAVING AT LEAST ONE HYDROGEN ATOM BONDED TO SAID AMINE GROUP AND HAVING AT LEAST ONE NUCLEAR POSITION ORTHO TO SAID AMINE GROUP UNSUBSTITUTED EXCEPT FOR HYDROGEN, SAID PROCESS COMPRISING REACTING SAID AROMATIC AMINE WITH AN OLEFIN HYDROCARBON AT A TEMPERATURE OF ABOUT 200*-400*C IN THE PRESENCE OF AN ALUMINUM ANILIDE CATALYST, THE IMPROVEMENT FORMING SAID ALUMINUM ANILIDE CATALYST BY ADDING AN ALKYL ALUMINUM HALIDE TO SAID AROMATIC AMINE, SAID IMPROVEMENT RESULTING IN AN ALKYLATION RATE IN EXCESS OF THAT OBTAINED UNDER THE SAME CONDITIONS USING A NON-HALOGEN ALUMINUM ANILIDE CATALYST.
Claim 3
Dependent Claim
12 words
The improved process of claim 1 wherein said aromatic amine is aniline.
Claim 4
Dependent Claim
11 words
The improved process of claim 2 wherein said olefin is ethylene.
Claim 5
Dependent Claim
15 words
The improved process of claim 3 wherein said alkyl aluminum halide is diethyl aluminum chloride.
Claim 6
Dependent Claim
11 words
The improved process of claim 2 wherein said olefin is propylene.
Claim 7
Dependent Claim
15 words
The improved process of claim 5 wherein said alkyl aluminum halide is ethyl aluminum sesquichloride.
Claim 8
Dependent Claim
12 words
The improved process of claim 1 wherein said aromatic amine is o-toluidine.
Claim 9
Dependent Claim
11 words
The improved process of claim 7 wherein said olefin is ethylene.
Claim 10
Dependent Claim
15 words
The improved process of claim 8 wherein said alkyl aluminum halide is diethyl aluminum chloride.
Claim 11
Dependent Claim
11 words
The improved process of claim 7 wherein said olefin is propylene.
Claim 12
Dependent Claim
15 words
The improved process of claim 10 wherein said alkyl aluminum halide is ethyl aluminum sesquichloride.
Claim 13
Dependent Claim
20 words
The improved process of claim 1 wherein said olefin is ethylene and said alkyl aluminum halide is diethyl aluminum chloride.
Claim 14
Dependent Claim
20 words
The improved process of claim 1 wherein said olefin is propylene and said alkyl aluminum halide is ethyl aluminum sesquichloride.
References Cited (Backward Citations)
US3275690A
Cited
US3649693A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-01 | 1979-06-02 | 1979-12-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-01 | 1983-06-02 | 1983-12-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-01 | 1987-06-02 | 1987-12-02 | $7700.00 | Window Closed / Lapsed |