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US4952549A
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Ruthenium catalyst, process for its preparation and process for the preparation of a mixture of cyclohexylamine and dicyclohexylamine using the ruthenium catalyst
Assignee: Bayer AG
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Filing: 1989-01-10
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Granted: 1990-08-28
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Expires: 2009-01-10
Abstract
Abstract Substituted or unsubstituted cyclohexylamine and substituted or substituted dicyclohexylamine can be produced by catalytic hydrogenation of substituted or unsubstituted aniline, for which a catalyst is used containing ruthenium and palladium which are attached to a support and which catalyst furthermore contains a basic alkali metal compound. The catalyst contains the noble metals in a total amount of 0.05 to 5% by weight and in a weight ratio of ruthenium to palladium such as 1:9-9:1. The basic alkali metal compound is present in an amount of 0.1-10% by weight. All percentages are based on the total weight of the catalyst.
Inventors
- 👤 Otto Immel
- 👤 Hans-Helmut Schwarz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 09:24
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/68; C07C209/70; C07C209/72; B; B01; B01J; B01J23/00; B01J23/38; B01J23/40; B01J23/46; B01J23/462; B01J23/54; B01J23/56; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
106 words
A process for the preparation of a mixture of a substituted or unsubstituted cyclohexylamine and a substituted or unsubstituted dicyclohexylamine by hydrogenation of a substituted or unsubstituted aniline in the presence of a ruthenium catalyst, wherein the catalyst comprises ruthenium and palladium on a support containing the noble metals in a total amount of 0.05-5% by weight and a weight ratio of ruthenium to palladium such as 1:9-9:1 and furthermore containing 0.1-10% by weight of an alkaline alkali metal compound, all percentages being based on the total weight of the catalyst, said hydrogenation being carried out at 150°-220° C. and at a pressure of 0.5-10 bar.
Claim 2
Dependent Claim
106 words
A process for the preparation of a mixture of a substituted or unsubstituted cyclohexylamine and a substituted or unsubstituted dicyclohexylamine by hydrogenation of a substituted or unsubstituted aniline in the presence of a ruthenium catalyst, wherein the catalyst comprises ruthenium and palladium on a support containing the noble metals in a total amount of 0.05-5% by weight and a weight ratio of ruthenium to palladium such as 1:9-9:1 and furthermore containing 0.1-10% by weight of an alkaline alkali metal compound, all percentages being based on the total weight of the catalyst, said hydrogenation being carried out at 150°-220° C. and at a pressure of 0.5-10 bar.
Claim 3
Dependent Claim
27 words
The process of claim 1, wherein to increase the percentage of dicyclohexylamine the hydrogenation is carried out at a lower temperature within the range of 150°-220° C.
Claim 4
Dependent Claim
26 words
The process of claim 1, wherein the space velocity of the catalyst is set to 0.5-2 kg of aniline per liter of catalyst and per hour.
Claim 5
Dependent Claim
37 words
The process of claim 1, wherein the aniline is of the formula ##STR2## in which R 1 and R 2 independently of one another denote hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
Claim 6
Dependent Claim
21 words
The process of claim 1 wherein 1-100 liters of hydrogen under standard conditions are used per 1 g of the aniline.
Claim 7
Dependent Claim
15 words
The process of claim 1, wherein the hydrogenation is carried out in the gas phase.
Claim 8
Dependent Claim
20 words
A process according to claim 1, wherein the noble metals are present in a total amount of 0.1-4% by weight.
Claim 9
Dependent Claim
20 words
A process according to claim 1, wherein the noble metals are present in a total amount of 0.1-3% by weight.
Claim 10
Dependent Claim
21 words
A process according to claim 1, wherein the noble metals are present in a weight ratio of ruthenium to palladium 2:8-8:2.
Claim 11
Dependent Claim
23 words
A process according to claim 1, wherein the noble metals are present in a weight ratio of ruthenium to palladium such as 3:7-7:3.
Claim 12
Dependent Claim
19 words
A process according to claim 1, wherein the catalyst contains 0.2-5% by weight of a basic alkali metal compound.
Claim 13
Dependent Claim
18 words
A process according to claim 1, wherein the support is Al 2 O 3 or an aluminum spinel.
Claim 14
Dependent Claim
20 words
A process according to claim 1, wherein, prior to its use, the catalyst is treated with hydrogen at 120°-400° C.
Claim 15
Dependent Claim
20 words
A process according to claim 13, wherein, prior to its use, the catalyst is treated with hydrogen at 150°-380° C.
Claim 16
Dependent Claim
29 words
A process according to claim 1 wherein the alkaline alkali metal compounds are the oxides, hydroxides, alcoholates or salts of weak acids of lithium, sodium, potassium, rubidium or caesium.
Claim 17
Dependent Claim
26 words
A process according to claim 15, wherein the alkaline alkali metal compounds are the oxides, hydroxides, alcoholates or salts of weak acids of sodium or potassium.
Claim 18
Dependent Claim
36 words
A process according to claim 1, wherein the catalyst support is aluminum oxide, aluminum spinel, activated carbon, kieselgur, bentonite, pumice, silica gel, ZrO 2 , TiO 2 , ZnO, MgO or an oxide of rare earths.
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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) | 1993-08-27 | 1994-02-26 | 1994-08-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-08-27 | 1998-02-26 | 1998-08-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-08-27 | 2002-02-26 | 2002-08-28 | $7700.00 | Window Closed / Lapsed |