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US5322965A
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Process for the preparation of a mixture of cyclohexylamine and dicyclohexylamine using a supported noble metal catalyst
Assignee: Bayer AG
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Filing: 1993-08-27
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Granted: 1994-06-21
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Expires: 2013-08-27
Abstract
Abstract Optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine can be obtained by catalytic hydrogenation of optionally substituted aniline, a catalyst being employed which contains ruthenium, palladium or a mixture of both metals, which are applied to a support of niobic acid or tantalic acid or a mixture of both. The catalyst contains the noble metal(s) in a total amount from 0.05 to 5% by weight, relative to the total weight of the catalyst. In the case of the use of both noble metals, their weight ratio to one another is 1:9-9:1.
Inventors
- 👤 Otto Immel
- 👤 Gerhard Darsow
- 👤 Helmut Waldmann
- 👤 Gerd-Michael Petruck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 13:02
CPC Classifications
B; B01; B01J; B01J23/00; B01J23/38; B01J23/40; B01J23/46; B01J23/462; B01J23/54; B01J23/56; B01J23/64; B01J23/648; C; C07; C07C; C07C209/00; C07C209/24; C07C209/26; C07C209/68; C07C209/70; C07C209/72; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
138 words
A process for the preparation of a mixture of optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine by catalytic hydrogenation of optionally substituted aniline on a supported noble metal catalyst, wherein a catalyst containing ruthenium, palladium or a mixture of both on a support containing niobic acid Nb 2 O 5 .nH 2 O, tantalic acid Ta 2 O 5 .nH 2 O or a mixture of both, which contains the noble metal(s) in a total amount from 0.05 to 5% by weight and in the case of an Ru/Pd mixture, contains both metals in a weight ratio of 1:9-9:1, all percentages being based on the total weight of the catalyst is employed and the reaction is carried out at a temperature in the range from 100° to 340° C. and at a pressure of 100 to 500 bar.
Claim 2
Dependent Claim
138 words
A process for the preparation of a mixture of optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine by catalytic hydrogenation of optionally substituted aniline on a supported noble metal catalyst, wherein a catalyst containing ruthenium, palladium or a mixture of both on a support containing niobic acid Nb 2 O 5 .nH 2 O, tantalic acid Ta 2 O 5 .nH 2 O or a mixture of both, which contains the noble metal(s) in a total amount from 0.05 to 5% by weight and in the case of an Ru/Pd mixture, contains both metals in a weight ratio of 1:9-9:1, all percentages being based on the total weight of the catalyst is employed and the reaction is carried out at a temperature in the range from 100° to 340° C. and at a pressure of 100 to 500 bar.
Claim 3
Dependent Claim
19 words
The process of claim 1, wherein the reaction is carried out in the range of 130° to 240° C.
Claim 4
Dependent Claim
19 words
The process of claim 1, wherein the reaction is carried out at a pressure of 100 to 400 bar.
Claim 5
Dependent Claim
41 words
The process of claim 1, wherein the reaction is carried out continuously in the liquid phase on a fixed catalyst packing and a catalyst loading of 0.05-3 kg of optionally substituted aniline per liter of catalyst and per hour is set.
Claim 6
Dependent Claim
25 words
The process of claim 4, wherein a catalyst loading of 0.1-2 kg of optionally substituted aniline per liter of catalyst and per hour is set.
Claim 7
Dependent Claim
38 words
The process of claim 1, wherein an aniline of the formula ##STR3## is employed 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 8
Dependent Claim
42 words
The process of claim 1, wherein, as the substituted aniline, the cyclohexylideneaniline of the formula ##STR4## is employed, 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 9
Dependent Claim
28 words
The process of claim 7, wherein the cyclohexylideneaniline is employed in the form of a mixture of the underlying, optionally substituted cyclohexanone with the underlying, optionally substituted aniline.
Claim 10
Dependent Claim
96 words
The process of claim 3, wherein the reaction is carried out in the range of 130° to 240° C., the catalyst consists essentially of palladium on said support, the reaction is carried out continuously in the liquid phase on a fixed catalyst packing and a catalyst loading of 0.1-2 kg of optionally substituted aniline per liter of catalyst and per hour, and the aniline subjected to hydrogenation is of the formula ##STR5## in which R 1 and R 2 independently of one another denote hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
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) | 1997-06-20 | 1997-12-20 | 1998-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-06-20 | 2001-12-20 | 2002-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-06-20 | 2005-12-20 | 2006-06-21 | $7700.00 | Window Closed / Lapsed |