US3679746A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Isomer enrichment of bicyclohexyl-4,4{40 -diamine
Assignee: EIDP Inc
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Filing: 1969-10-27
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Granted: 1972-07-25
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Expires: 1989-10-27
Abstract
Abstract A mixture of the stereoisomers of bicyclohexyl-4,4''-diamine not at equilibrium is converted to a mixture of stereoisomers approaching the equilibrium ratio by heating the mixture of stereoisomers to a temperature of from 150* to 300* C. in the presence of hydrogen at a pressure of from 50 to 5,500 pounds per square inch gage and a total pressure of from 500 to 15,000 pounds per square inch gage, in the presence of from 0 to 200 percent by weight of added ammonia and from 0.001 to 10 percent by weight, calculated as metallic ruthenium, of a ruthenium catalyst supported on an inert carrier, both percentages being based on the weight of a starting material, said catalyst being alkali moderated with from 0.05 to 15 percent of a basic alkali metal compound calculated as the alkali metal. Either essentially pure trans,trans-bicyclohexyl-4,4''-diamine or an enriched mixture of cis,trans- and cis,cis-bicyclohexyl-4,4''-diamine can be recovered.
Inventors
- 👤 Loren D Brake
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 08:17
CPC Classifications
B; B01; B01J; B01J23/00; B01J23/38; B01J23/54; B01J23/56; B01J23/63; B01J23/58
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
25 words
The process of claim 1 wherein the starting material is a mixture of stereoisomers of bicyclohexyl-4,4''-diamine containing less than the equilibrium concentration of the trans,trans-stereoisomer.
Claim 2
Dependent Claim
27 words
dissolving the diamine product of step (1) in a solvent and cooling the solution to a temperature of from 10* to 75* C. to precipitate trans,trans-bicyclohexyl-4,4''-diamine; and
Claim 3
Dependent Claim
27 words
dissolving the diamine product of step (1) in a solvent and cooling the solution to a temperatuRe of from 10* to 75* C. to precipitate trans,trans-bicyclohexyl-4,4''-diamine; and
Claim 4
Dependent Claim
10 words
recovering the precipitate of step (2) as essentially pure trans,trans-bicyclohexyl-4,4''-diamine.
Claim 5
Dependent Claim
20 words
separating the precipitate of step (2) to obtain a solution of the stereoisomeric mixture enriched in cis,trans- and cis, cis-bicyclohexyl--4,4''-diamine.
Claim 6
Dependent Claim
14 words
The process of claim 1 wherein the amount of added ammonia is 0 percent.
Claim 7
Dependent Claim
14 words
The process of claim 2 wherein the amount of added ammonia is 0 percent.
Claim 8
Dependent Claim
20 words
The process of claim 1 wherein the liquid separated from the precipitate of step (3) is recycled to step (1).
Claim 9
Dependent Claim
34 words
The process of claim 1 wherein the catalyst carrier is selected from the group consisting of alumina, barium sulfate, kieselguhr, carbon, calcium carbonate, rare earth oxides, rare earth carbonates, and mixed rare earth oxide-carbonates.
Claim 10
Dependent Claim
21 words
The process of claim 1 wherein the catalyst carrier is selected from the group consisting of alumina, barium sulfate and kieselguhr.
Claim 11
Dependent Claim
29 words
The process of claim 1 wherein the catalyst is moderated with from 0.1 to 10 percent by weight of a basic alkali metal compound calculated as the alkali metal.
Claim 12
Dependent Claim
34 words
The process of claim 8 wherein basic alkali metal compound is selected from the group consisting of (i) the hydroxides, carbonates, bicarbonates, and alkoxides of sodium, lithium, cesium, rubidium, and potassium, and (ii) sodamide.
Claim 13
Dependent Claim
17 words
The process of claim 1 wherein the temperature in step (1) varies from 180* to 225* C.
Claim 14
Dependent Claim
17 words
The process of claim 1 wherein the essentially pure trans, trans-bicyclohexyl-4,4''-diamine contains at least 85 percent trans,trans-bicyclohexyl-4,4''-diamine.
Claim 15
Dependent Claim
16 words
The process of claim 1 wherein the essentially pure trans-trans-bicyclohexyl-4,4''-diamine contains at least 99.9 percent trans,trans-bicyclohexyl-4,4''-diamine.
Claim 16
Dependent Claim
22 words
A process for the preparation of a stereoisomeric mixture of bicyclohexyl-4,4''-diamine rich in the cis, trans- and cis,cis-stereoisomers comprising the steps of
Claim 17
Dependent Claim
27 words
The process of claim 11 wherein the starting material is a mixture of stereoisomers of bicyclohexyl-4,4''-diamine containing less than the equilibrium concentration of the cis,trans- and cis,cis-stereoisomers.
Claim 18
Dependent Claim
14 words
The process of claim 11 wherein the amount of added ammOnia is 0 percent.
Claim 19
Dependent Claim
14 words
The process of claim 12 wherein the amount of added ammonia is 0 percent.
Claim 20
Dependent Claim
17 words
The process of claim 13 wherein the precipitate separated in step (3) is recycled to step (1).
Claim 21
Dependent Claim
34 words
The process of claim 13 wherein the catalyst carrier is selected from the group consisting of alumina, barium sulfate, kieselguhr, carbon, calcium carbonate, rare earth oxides, rare earth carbonates, and mixed rare earth oxide-carbonates.
Claim 22
Dependent Claim
21 words
The process of claim 13 wherein the catalyst carrier is selected from the group consisting of alumina, barium sulfate and kieselguhr.
Claim 23
Dependent Claim
29 words
The process of claim 13 wherein the catalyst is moderated with from 0.1 to 10 percent by weight of a basic alkali metal compound calculated as the alkali metal.
Claim 24
Dependent Claim
34 words
The process of claim 20 wherein basic alkali metal compound is selected from the group consisting of (i) the hydroxides, carbonates, bicarbonates, and alkoxides of sodium, lithium, cesium, rubidium, and potassium, and (ii) sodamide.
Claim 25
Dependent Claim
17 words
The process of claim 13 wherein the temperature in step (1) varies from 180* to 225* C.
Claim 26
Dependent Claim
18 words
The process of claim 13 wherein the bicyclohexyl-4,4''-diamine product contains at least 70 percent cis,cis- and cis, trans-bicyclohexyl-4,4''-diamine.
Claim 27
Dependent Claim
18 words
The process of claim 13 wherein the bicyclohexyl-4,4''-diamine product contains at least 85 percent cis,cis- and cis, trans-bicyclohexyl-4,4''-diamine.
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) | 1975-07-25 | 1976-01-24 | 1976-07-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-07-25 | 1980-01-24 | 1980-07-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-07-25 | 1984-01-24 | 1984-07-25 | $7700.00 | Window Closed / Lapsed |