Patent US4713269A successfully refreshed from Google Patents.
Patent US4317931A successfully refreshed from Google Patents.
US4317931A
Expired / Lapsed
US
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Process for rearrangement of alkyl groups on aromatic amines
Assignee: Ethyl Corp
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Filing: 1981-03-05
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Granted: 1982-03-02
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Expires: 2001-03-05
Abstract
Abstract Methyl groups on o-methyl aromatic amine are redistributed to ortho positions by heating in contact with an aluminum anilide catalyst and a nickel, cobalt, molybdenum or titanium-containing cocatalyst. For example, o-toluidine forms a mixture containing an aniline, o-toluidine, 2,6-dimethylaniline, and 2,4-dimethylaniline.
Inventors
- 👤 John C. Wollensak
- 👤 Kryn G. Ihrman
- 👤 Chester P. Jarema
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 18:31
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/68
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
84 words
A process for redistributing methyl groups on nuclear methyl-substituted aromatic amines, said process comprising heating an aromatic amine or mixture of aromatic amines, said aromatic amine or mixture of aromatic amines containing (a) aromatic amine having at least one o-methyl substituent and (b) aromatic amine having at least one ortho position unsubstituted except for hydrogen, at a temperature of about 100°-500° C. in the presence of an aluminum anilide catalyst and a metal-containing cocatalyst, said metal being selected from nickel, cobalt, molybdenum and titanium.
Claim 2
Dependent Claim
84 words
A process for redistributing methyl groups on nuclear methyl-substituted aromatic amines, said process comprising heating an aromatic amine or mixture of aromatic amines, said aromatic amine or mixture of aromatic amines containing (a) aromatic amine having at least one o-methyl substituent and (b) aromatic amine having at least one ortho position unsubstituted except for hydrogen, at a temperature of about 100°-500° C. in the presence of an aluminum anilide catalyst and a metal-containing cocatalyst, said metal being selected from nickel, cobalt, molybdenum and titanium.
Claim 3
Dependent Claim
18 words
A process of claim 1 wherein said aromatic amine or mixture of aromatic amines consists mainly of o-toluidine.
Claim 4
Dependent Claim
21 words
A process of claim 2 wherein said aluminum anilide catalyst is aluminum tri-(o-methyl anilide) and said cocatalyst is a nickel compound.
Claim 5
Dependent Claim
12 words
A process of claim 3 wherein said nickel compound is nickel carbonate.
Claim 6
Dependent Claim
21 words
A process of claim 2 wherein said aluminum anilide catalyst is aluminum tri-(o-methyl anilide) and said cocatalyst is a cobalt compound.
Claim 7
Dependent Claim
12 words
A process of claim 5 wherein said cobalt compound is cobalt naphthenate.
Claim 8
Dependent Claim
21 words
A process of claim 2 wherein said aluminum anilide catalyst is aluminum tri-(o-methyl anilide) and said cocatalyst is a molybdenum compound.
Claim 9
Dependent Claim
12 words
A process of claim 7 wherein said molybdenum compound is molybdenum naphthenate.
Claim 10
Dependent Claim
21 words
A process of claim 2 wherein said aluminum anilide catalyst is aluminum tri-(o-methyl anilide) and said cocatalyst is a titanium compound.
Claim 11
Dependent Claim
13 words
A process of claim 9 wherein said titanium compound is a titanium tetraalkoxide.
Claim 12
Dependent Claim
12 words
A process of claim 10 wherein said titanium tetraalkoxide is titanium tetrabutoxide.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-03-01 | 1985-08-31 | 1986-03-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-01 | 1989-08-31 | 1990-03-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-01 | 1993-08-31 | 1994-03-02 | $7700.00 | Window Closed / Lapsed |