Patent BE637847A successfully refreshed from Google Patents.
US3880930A
Expired / Lapsed
US
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Process for the production of 1-{8 cyclohexene-(1-YL{9 )-cyclohexanone-(2) by condensation of cyclohexanone
Assignee: Rain Carbon Germany GmbH
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Filing: 1973-05-24
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Granted: 1975-04-29
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Expires: 1993-05-24
Abstract
Abstract In a process for the preparation of 1-(cyclohexene-(1-yl)cyclohexanone-(2) by the condensation of cyclohexanone in the presence of a catalyst having high acidity and at an elevated temperature, the improvement wherein said process comprises heating cyclohexanone and at least one catalyst of the HSO3-type at about 80*- 110C., at a pressure of about 60 - 200 torr and under reflux while removing by distillation water formed during said heating step. Typical catalysts are cation exchange resins of the HSO3-type, benzenesulfonic acid and p-toluene sulfonic acid.
Inventors
- 👤 Klaus Ramm
- 👤 Wilfried Thielecke
- 👤 Maximilian Zander
- 👤 Gerd Collin
- 👤 Karl Ruhl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:37
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/74
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
82 words
IN A PROCESS FOR THE PREPARATION OF 1- CYCLOHEXENE-(1YL)!-CYCLOHEXANE-(2) BY THE CONDENSATION OF CYCLOHEXANONE IN THE PRESENCE OF A CATALYST HAVING HIGH ACIDITY AND AT AN ELEVATED TEMPERATURE UNDER REFLUX WHILE REMOVING BY DISTILLATION WATER FORMED DURING SAID HEATING STEP, THE IMPROVEMENT WHEREIN SAID PROCESS COMPRISES HEATING TO BOILING AT A PRESSURE OF ABOUT 60 - 200 TORR CYCLOHEXANONE AND AT LEAST ONE CATALYST SELECTED FROM THE GROUP CONSISTING OF SULFONIC ACID CATION EXCHANGE RESIN, BENZENE SULFONIC ACID AND TOLUENE SULFONIC ACID.
Claim 2
Dependent Claim
82 words
IN A PROCESS FOR THE PREPARATION OF 1- CYCLOHEXENE-(1YL)!-CYCLOHEXANE-(2) BY THE CONDENSATION OF CYCLOHEXANONE IN THE PRESENCE OF A CATALYST HAVING HIGH ACIDITY AND AT AN ELEVATED TEMPERATURE UNDER REFLUX WHILE REMOVING BY DISTILLATION WATER FORMED DURING SAID HEATING STEP, THE IMPROVEMENT WHEREIN SAID PROCESS COMPRISES HEATING TO BOILING AT A PRESSURE OF ABOUT 60 - 200 TORR CYCLOHEXANONE AND AT LEAST ONE CATALYST SELECTED FROM THE GROUP CONSISTING OF SULFONIC ACID CATION EXCHANGE RESIN, BENZENE SULFONIC ACID AND TOLUENE SULFONIC ACID.
Claim 3
Dependent Claim
19 words
Process according to claim 1 in which said catalyst having high acidity is a sulfonic acid cation exchange resin.
Claim 4
Dependent Claim
13 words
Process according to claim 1 in which the catalyst is p-toluene sulfonic acid.
Claim 5
Dependent Claim
13 words
Process according to claim 1 in which the catalyst is benzene sulfonic acid.
Claim 6
Dependent Claim
19 words
Process according to claim 1 in which said cyclohexanone is heated with about 4% by weight of said catalyst.
Claim 7
Dependent Claim
33 words
Process according to claim 1 in which water formed is distilled off with cyclohexanone, the water and cyclohexanone in the distillate are at least partially separated, and cyclohexanone is returned to the reaction.
Claim 8
Dependent Claim
33 words
Process according to claim 5 in which water formed is distilled off with cyclohexanone, the water and cyclohexanone in the distillate are at least partially separated, and cyclohexanone is returned to the reaction.
Claim 9
Dependent Claim
21 words
Process according to claim 1 in which the cyclohexanone and catalyst are heated for about 45 minutes to about 5 hours.
Claim 10
Dependent Claim
21 words
Process according to claim 5 in which the cyclohexanone and catalyst are heated for about 45 minutes to about 5 hours.
Claim 11
Dependent Claim
21 words
Process according to claim 6 in which the cyclohexanone and catalyst are heated for about 45 minutes to about 5 hours.
Claim 12
Dependent Claim
21 words
Process according to claim 7 in which the cyclohexanone and catalyst are heated for about 45 minutes to about 5 hours.
Claim 13
Dependent Claim
14 words
Process according to claim 6 in which the resulting product is separated by filtration.
Claim 14
Dependent Claim
14 words
Process according to claim 10 in which the resulting product is separated by filtration.
Claim 15
Dependent Claim
16 words
Process according to claim 12 in which the product is washed with water after the filtration.
Claim 16
Dependent Claim
16 words
Process according to claim 13 in which the product is washed with water after the filtration.
References Cited (Backward Citations)
DE857960C
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-04-28 | 1978-10-28 | 1979-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-04-28 | 1982-10-28 | 1983-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-04-28 | 1986-10-28 | 1987-04-29 | $7700.00 | Window Closed / Lapsed |