US3868420A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Nuclear alkylation of anilins
Assignee: Sandoz AG
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Filing: 1972-08-14
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Granted: 1975-02-25
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Expires: 1992-08-14
Abstract
Abstract The present invention provides a process for the production of phenylamines alkylated in the ortho and/or para positions by alkyl groups of 1 to 4 carbon atoms and unsubstituted on the amino group, which comprises reacting a phenylamine having an ortho and/or para position available for alkylation with an alkanol of 1 to 4 carbon atoms in the vapour phase and with heating to a temperature of from 350* to 450*C, using a catalyst selected from aluminium oxide and aluminium oxide/molybdenum oxide mixed catalyst in which the amount of molybdenum oxide is approximately from 0.01 to 20 percent by weight, which catalyst has a minimum surface area 50 m2/g.
Inventors
- 👤 Frank Evans
- 👤 Walter Frey
- 👤 Joerg Staeheli
- 👤 Istvan Toth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 14:13
CPC Classifications
B; B01; B01J; B01J23/00; B01J23/16; B01J23/24; B01J23/28; C; C07; C07C; C07C209/00; C07C209/68
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
104 words
A PROCESS FOR THE PRODUCTION OF PHENYLAMINE ALKYLATED IN THE ORTHO AND/OR PARA POSITIONS BY ALKYL GROUPS OF 1 TO 4 CARBON ATOMS AND UNSUBSTITUTED ON THE AMINO GROUP, WHICH COMPRISES THE STEP OF REACTING A PHENYLAMINE HAVING AN ORTHO AND/OR PARA POSITION AVAILABLE FOR ALKYLATION WITH AN ALKANOL OF 1 TO 4 CARBON ATOMS IN THE VAPOR PHASE AND WITH HEATING TO A TEMPERATURE OF FROM 350* TO 450*C, IN THE PRESENCE OF ALUMINUM OXIDE/MOLYBDENUM OXIDE MIXED CATALYST IN WHICH THE AMOUNT OF MOLYBDENUM OXIDE IS APPROXIMATELY FROM 0.01 TO 20 PERCENT BY WEIGT, WHICH CATALYST HAS A MINIMUM SURFACE AREA OF 50M2/G.
Claim 2
Dependent Claim
104 words
A PROCESS FOR THE PRODUCTION OF PHENYLAMINE ALKYLATED IN THE ORTHO AND/OR PARA POSITIONS BY ALKYL GROUPS OF 1 TO 4 CARBON ATOMS AND UNSUBSTITUTED ON THE AMINO GROUP, WHICH COMPRISES THE STEP OF REACTING A PHENYLAMINE HAVING AN ORTHO AND/OR PARA POSITION AVAILABLE FOR ALKYLATION WITH AN ALKANOL OF 1 TO 4 CARBON ATOMS IN THE VAPOR PHASE AND WITH HEATING TO A TEMPERATURE OF FROM 350* TO 450*C, IN THE PRESENCE OF ALUMINUM OXIDE/MOLYBDENUM OXIDE MIXED CATALYST IN WHICH THE AMOUNT OF MOLYBDENUM OXIDE IS APPROXIMATELY FROM 0.01 TO 20 PERCENT BY WEIGT, WHICH CATALYST HAS A MINIMUM SURFACE AREA OF 50M2/G.
Claim 3
Dependent Claim
20 words
A process according to claim 1, in which the catalyst has a surface area of from 150 to 300 m2/g.
Claim 4
Dependent Claim
23 words
A process according to claim 2, in which a catalyst is used containing from 1 to 2.5 percent by weight of molybdenum oxide.
Claim 5
Dependent Claim
21 words
A process according to claim 1 wherein the alkanol: phenylamine mol ratio is at least stoichiometric but not greater than 10:1.
Claim 6
Dependent Claim
90 words
A process according to claim 1 for the production of phenylamine methylated in the ortho and/or para positions and unsubstituted on the amino group, which comprises the step of reacting a phenylamine having an available ortho and/or para position with methanol in the vapor phase and with heating to a temperature of from 350* to 450*C. in the presence of an aluminum oxide/molybdenum oxide mixed catalyst which the amount of molybdenum oxide is approximately from 0.01 to 20 percent by weight, which catalyst has a minimum surface area of 50m2/g.
Claim 7
Dependent Claim
30 words
A process according to claim 5, in which a phenylamine selected from aniline, toluidines, xylidines and mixtures of any two or more thereof is reacted with methanol to produce mesidine.
Claim 8
Dependent Claim
16 words
A process according to claim 6, in which p-toluidine is reacted with methanol to produce mesidine.
Claim 9
Dependent Claim
23 words
A process according to claim 7, in which the molecular ratio of methanol to p-toluidine is in the range from 2:1 to 10:1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-02-24 | 1978-08-26 | 1979-02-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-02-24 | 1982-08-26 | 1983-02-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-02-24 | 1986-08-26 | 1987-02-25 | $7700.00 | Window Closed / Lapsed |