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US4183868A
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Process for the preparation of 2,6-dialkyl-N-alkylanilines
Assignee: Novartis Corp
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Filing: 1978-04-26
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Granted: 1980-01-15
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Expires: 1998-04-26
Abstract
Abstract A process for the preparation of 2,6-dialkyl-N-alkylanilines is disclosed, which process comprises the reaction of a 2,6-dialkylaniline with an alkanol at 200 DEG to 350 DEG C. in the presence of a copper-containing catalyst which contains 0.05 to 10% by weight of palladium or platinum.
Inventors
- 👤 Paul Radimerski
- 👤 Milos Rusek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:19
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/04; C07C209/14; C07C209/18; B; B01; B01J; B01J23/00; B01J23/70; B01J23/89; B01J23/8933; B01J23/8993
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
130 words
A process for the preparation of a 2,6-dialkyl-N-alkylaniline of the formula I ##STR4## in which R 1 and R 2 independently of one another are each methyl or ethyl, R 3 is hydrogen, methyl or ethyl and R 4 is an alkyl group having 1 to 11 carbon atoms or an alkoxymethyl group having 1 to 8 carbon atoms in the alkyl group, which comprises reacting a 2,6-dialkylaniline of the formula II ##STR5## in which R 1 and R 2 are as defined under formula I, in the presence of a copper-containing catalyst which contains 0.05 to 10% by weight of palladium or platinum, at 200° to 350° C., with an alcohol of the formula III ##STR6## in which R 3 and R 4 are as defined under formula I.
Claim 2
Dependent Claim
130 words
A process for the preparation of a 2,6-dialkyl-N-alkylaniline of the formula I ##STR4## in which R 1 and R 2 independently of one another are each methyl or ethyl, R 3 is hydrogen, methyl or ethyl and R 4 is an alkyl group having 1 to 11 carbon atoms or an alkoxymethyl group having 1 to 8 carbon atoms in the alkyl group, which comprises reacting a 2,6-dialkylaniline of the formula II ##STR5## in which R 1 and R 2 are as defined under formula I, in the presence of a copper-containing catalyst which contains 0.05 to 10% by weight of palladium or platinum, at 200° to 350° C., with an alcohol of the formula III ##STR6## in which R 3 and R 4 are as defined under formula I.
Claim 3
Dependent Claim
31 words
A process according to claim 1, which comprises carrying out the reaction of a 2,6-dialkylaniline of the formula II with an alcohol of the formula III in the presence of hydrogen.
Claim 4
Dependent Claim
35 words
A process according to claim 1, which comprises carrying out the reaction of a 2,6-dialkylaniline of the formula II with an alcohol of the formula III at a temperature of between 220° and 300° C.
Claim 5
Dependent Claim
34 words
A process according to claim 1, which comprises carrying out the reaction of a 2,6-dialkylaniline of the formula II with an alcohol of the formula III under a pressure of 2 to 5 bars.
Claim 6
Dependent Claim
47 words
A process according to claim 1, which comprises carrying out the reaction of a 2,6-dialkylaniline of the formula II with an alcohol of the formula III under normal pressure in the presence of 1 to 3 mols of hydrogen per mol of 2,6-dialkylaniline of the formula II.
Claim 7
Dependent Claim
52 words
A process according to claim 1, which comprises carrying out the reaction of a 2,6-dialkylaniline of the formula II with an alcohol of the formula III under a pressure of 2 to 5 bars in the presence of 2 to 10 mols of hydrogen per mol of 2,6-dialkylaniline of the formula II.
Claim 8
Dependent Claim
65 words
A process according to claim 1, which comprises carrying out the reaction of a 2,6-dialkylaniline of the formula II with an alcohol of the formula III in the presence of a copper oxide/chromium oxide catalyst which has a molar ratio of copper oxide:chromium oxide of 1:1 to 15:1 and contains 0.05 to 10% by weight, preferably 0.2 to 3% by weight, of palladium or platinum.
Claim 9
Dependent Claim
39 words
A catalyst mixture consisting essentially of copper oxide and chromium oxide, wherein the molar ratio of copper oxide to chromium oxide is 1:1 to 15:1, which catalyst mixture additionally contains 0.05 to 10% by weight of palladium or platinum.
Claim 10
Dependent Claim
39 words
A catalyst mixture consisting essentially of copper oxide and chromium oxide, wherein the molar ratio of copper oxide to chromium oxide is 1:1 to 15:1, which catalyst mixture additionally contains 0.05 to 10% by weight of palladium or platinum.
Claim 11
Dependent Claim
17 words
The catalyst mixture of claim 8 which contains 0.2 to 3% by weight of palladium or platinum.
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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) | 1983-01-14 | 1983-07-16 | 1984-01-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-14 | 1987-07-16 | 1988-01-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-14 | 1991-07-16 | 1992-01-15 | $7700.00 | Window Closed / Lapsed |