US4210602A
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US
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Process for the preparation of asymmetrical N-phenyl-N'-substituted para-phenylene diamines
Assignee: Akzona Inc
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Filing: 1979-02-23
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Granted: 1980-07-01
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Expires: 1999-02-23
Abstract
Abstract An improved process for the preparation of asymmetrical N-phenyl-N'-substituted para-phenylene diamines by the reductive alkylation of para-nitroso-diphenylhydroxylamine with an aldehyde or a ketone in the presence of hydrogen and a hydrogenation catalyst is disclosed. The improvement comprises utilizing as the hydrogenation catalyst (1) one member selected the group consisting of palladium and platinum sulfide, in an amount less than 1%, by weight, based on the weight of para-nitroso-diphenylhydroxylamine, and (2) activated carbon with a specific surface area of at least 700 square meters per gram and an ash content of less than 7.5%, by weight.
Inventors
- 👤 Manfred Bergfeld
- 👤 Hans G. Zengel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:44
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/24; C07C209/26; C07C209/30; C07C209/32; C07C209/36; C07C211/00; C07C211/43; C07C211/44; C07C211/49; C07C211/50; C07C213/00; C07C213/02
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
112 words
In an improved process for the preparation of asymmetrical N-phenyl-N'-substituted para-phenylene diamines by the reductive alkylation of para-nitroso-diphenylhydroxylamine with an aldehyde or a ketone in the presence of hydrogen and a hydrogenation catalyst, the improvement comprising utilizing as the hydrogenation catalyst (1) one member selected from the group consisting of palladium and platinum sulfide, in an amount less than 1%, by weight based on the weight of para-nitroso-diphenylhydroxylamine, and (2) activated carbon with a specific surface area of at least 700 square meters per gram and an ash content of less than 7.5%, by weight, in an amount from about 10 to about 200%, by weight based on the weight of para-nitroso-diphenylhydroxylamine.
Claim 2
Dependent Claim
112 words
In an improved process for the preparation of asymmetrical N-phenyl-N'-substituted para-phenylene diamines by the reductive alkylation of para-nitroso-diphenylhydroxylamine with an aldehyde or a ketone in the presence of hydrogen and a hydrogenation catalyst, the improvement comprising utilizing as the hydrogenation catalyst (1) one member selected from the group consisting of palladium and platinum sulfide, in an amount less than 1%, by weight based on the weight of para-nitroso-diphenylhydroxylamine, and (2) activated carbon with a specific surface area of at least 700 square meters per gram and an ash content of less than 7.5%, by weight, in an amount from about 10 to about 200%, by weight based on the weight of para-nitroso-diphenylhydroxylamine.
Claim 3
Dependent Claim
30 words
The process of claim 1 wherein the palladium or platinum sulfide is present in an amount from about 0.05 to about 0.2%, by weight based on the weight of para-nitroso-diphenylhydroxylamine.
Claim 4
Dependent Claim
28 words
The process of claim 1 or 2 wherein the aldehyde or ketone is utilized in an amount from about 2 to about 10 equivalents, per equivalent of para-nitroso-diphenylhydroxylamine.
Claim 5
Dependent Claim
18 words
The process of claim 1 wherein the reductive alkylation is performed in the presence of an inert solvent.
Claim 6
Dependent Claim
18 words
The process of claim 3 wherein the reductive alkylation is performed in the presence of an inert solvent.
Claim 7
Dependent Claim
23 words
The process of claim 4 wherein the inert solvent is selected from the group consisting of methanol, ethanol, isopropanol, propanol, butanol, and pentanols.
Claim 8
Dependent Claim
23 words
The process of claim 5 wherein the inert solvent is selected from the group consisting of methanol, ethanol, isopropanol, propanol, butanol, and pentanols.
Claim 9
Dependent Claim
33 words
The process of claim 1 wherein the reductive alkylation is performed at a temperature from about 25° to about 125° C., and at a hydrogen pressure from about 1 to about 150 bar.
Claim 10
Dependent Claim
33 words
The process of claim 7 wherein the reductive alkylation is performed at a temperature from about 25° to about 125° C., and at a hydrogen pressure from about 1 to about 150 bar.
Claim 11
Dependent Claim
33 words
The process of claim 1 wherein the reductive alkylation is performed at a temperature from about 40° to about 100° C. and at a hydrogen pressure from about 7 to about 12 bar.
Claim 12
Dependent Claim
33 words
The process of claim 7 wherein the reductive alkylation is performed at a temperature from about 40° to about 100° C. and at a hydrogen pressure from about 7 to about 12 bar.
References Cited (Backward Citations)
GB1295672A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-07-01 | 1983-12-31 | 1984-07-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-07-01 | 1987-12-31 | 1988-07-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-07-01 | 1991-12-31 | 1992-07-01 | $7700.00 | Window Closed / Lapsed |