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US4551564A
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Process for the production of 2- and 4-tert-butylcyclohexanols with high proportions of cis-isomers by catalytic-hydrogenation of the corresponding tert-butylphenols
Assignee: Evonik Operations GmbH
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Filing: 1984-10-22
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Granted: 1985-11-05
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Expires: 2004-10-22
Abstract
Abstract 2- and 4-tert-butylcyclohexanols are produced having high proportions of cis-isomers, by hydrogenating the corresponding tert-butylphenols in the presence of Pd and Ru catalysts in two stages under hydrogen pressures of above 200 bar and at temperatures of 70°-280° C. In the first stage, a Pd catalyst is employed, and a Ru catalyst is used in the second stage.
Inventors
- 👤 Werner Otte
- 👤 Rudolf Nehring
- 👤 Manfred zur Hausen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 14:45
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/17; C07C29/19; C07C29/20; C07C45/00; C07C45/006; C07B; C07B2200/00; C07B2200/09; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
65 words
A process for the production of 2- or 4-tertbutylcyclohexanol having a high proportion of cis-isomers comprising hydrogenating the corresponding tert-butylphenol in two stages under hydrogen pressures of above 200 bar in each stage, and, in the first stage, on a Pd metal catalyst at a temperature of 120°-280° C. and, in the second stage, on a Ru metal catalyst at a temperature of 70°-200° C.
Claim 2
Dependent Claim
65 words
A process for the production of 2- or 4-tertbutylcyclohexanol having a high proportion of cis-isomers comprising hydrogenating the corresponding tert-butylphenol in two stages under hydrogen pressures of above 200 bar in each stage, and, in the first stage, on a Pd metal catalyst at a temperature of 120°-280° C. and, in the second stage, on a Ru metal catalyst at a temperature of 70°-200° C.
Claim 3
Dependent Claim
37 words
A process of claim 1, wherein the hydrogenation in the first stage is carried out at a temperature of 160°-220° C. and the hydrogenation in the second stage is carried out at a temperature of 100°-150° C.
Claim 4
Dependent Claim
20 words
A process of claim 2, wherein at least one hydrogenation stage is carried out under a pressure of 250-350 bar.
Claim 5
Dependent Claim
40 words
A process of claim 3, wherein in said first stage, the tert-butylphenol is introduced continuously and the first stage product is recycled to the first stage, in an amount which is 1 to 20 times the amount of feed tert-butylphenol.
Claim 6
Dependent Claim
27 words
A process of claim 4, wherein the amount of product returned to said first stage is 5-10 times the amount of tert-butylphenol introduced to said first stage.
Claim 7
Dependent Claim
14 words
A process of claim 2, wherein the catalysts are supported on an inert carrier.
Claim 8
Dependent Claim
14 words
A process of claim 3, wherein the catalysts are supported on an inert carrier.
Claim 9
Dependent Claim
14 words
A process of claim 4, wherein the catalysts are supported on an inert carrier.
Claim 10
Dependent Claim
11 words
A process of claim 6, wherein the support is aluminum oxide.
Claim 11
Dependent Claim
11 words
A process of claim 7, wherein the support is aluminum oxide.
Claim 12
Dependent Claim
11 words
A process of claim 8, wherein the support is aluminum oxide.
Claim 13
Dependent Claim
22 words
A process of claim 9, wherein the catalyst is affixed to the carrier in a concentration of 0.1% to 5% by weight.
Claim 14
Dependent Claim
22 words
A procsss of claim 10, wherein the catalyst is affixed to the carrier in a concentration of 0.1% to 5% by weight.
Claim 15
Dependent Claim
22 words
A process of claim 11, wherein the catalyst is affixed to the carrier in a concentration of 0.1% to 5% by weight.
Claim 16
Dependent Claim
20 words
A process of claim 9, wherein the catalyst is affixed to the carrier in a concentration of 0.5%-1% by weight.
Claim 17
Dependent Claim
20 words
A process of claim 10, wherein the catalyst is affixed to the carrier in a concentration of 0.5%-1% by weight.
Claim 18
Dependent Claim
20 words
A process of claim 11, wherein the catalyst is affixed to the carrier in a concentration of 0.5%-1% by weight.
Claim 19
Dependent Claim
16 words
A process of claim 1, wherein the throughput is 0.1-5 liters of feed/liter of catalyst hour.
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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) | 1988-11-04 | 1989-05-06 | 1989-11-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-11-04 | 1993-05-06 | 1993-11-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-11-04 | 1997-05-06 | 1997-11-05 | $7700.00 | Window Closed / Lapsed |