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US4463191A
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Process for the reductive alkylation of aromatic nitro-containing compounds with ketones or aldehydes
Assignee: Goodyear Tire and Rubber Co
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Filing: 1983-09-26
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Granted: 1984-07-31
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Expires: 2003-09-26
Abstract
Abstract There is disclosed a process for the reductive alkylation of aromatic nitro-containing compounds with ketones or aldehydes wherein the improvement is characterized in that a specific polymer bound co-catalyst system is utilized. More specifically, a polymer bound anthranilic acid palladium complex is used in conjunction with a bound sulfonic acid resin as a catalyst system in a reaction to produce compounds such as N-phenyl-N'-alkyl-p-phenylenediamine.
Inventors
- 👤 Richard M. D'Sidocky
- 👤 Dane K. Parker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 23:03
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/24; C07C209/26; B; B01; B01J; B01J31/00; B01J31/02; B01J31/06; B01J31/08; B01J31/10; B01J31/16; B01J31/165; B01J31/1658; B01J31/18; B01J31/1805; B01J2231/00; B01J2231/30; B01J2231/34; B01J2231/341; B01J2231/60; B01J2231/64; B01J2231/641; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/824
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
60 words
A process for the reductive alkylation of aromatic nitro-containing compounds with ketones or aldehydes wherein the improvement is characterized in that the reaction is conducted in one-step using a catalyst system that consists of (1) a polymer bound anthranilic acid-Pd complex and (2) a sulfonic acid resin at a temperature from 20°-200° C. and pressure from atmospheric to 35,000 kPa.
Claim 2
Dependent Claim
60 words
A process for the reductive alkylation of aromatic nitro-containing compounds with ketones or aldehydes wherein the improvement is characterized in that the reaction is conducted in one-step using a catalyst system that consists of (1) a polymer bound anthranilic acid-Pd complex and (2) a sulfonic acid resin at a temperature from 20°-200° C. and pressure from atmospheric to 35,000 kPa.
Claim 3
Dependent Claim
53 words
A process according to claim 1 wherein the aromatic nitro-containing compound is p-nitrodiphenylamine, the ketone is methylisobutyl ketone, the polymer bound anthranilic acid palladium complex is a macroreticular styrene/vinylbenzyl chloride/divinylbenzene resin that contains at least 4% crosslinking and from 0.001 to 10% palladium. by weight and the sulfonic acid resin is Amberlyst 15.
Claim 4
Dependent Claim
21 words
A process according to claim 1 wherein the reaction is conducted from 60°-150° C. and at a pressure of 350-7000 kPa.
Claim 5
Dependent Claim
141 words
A process wherein (1) a nitrodiphenylamine conforming to the following structural formula: ##STR16## wherein R and R 1 are selected from the group consisting of hydrogen radicals and alkyl radicals of 1 to 9 carbon atoms, R 2 and R 3 are selected from the group consisting of hydrogen radicals, alkyl radicals of 1 to 9 carbon atoms and alkoxy radicals of 1 to 9 carbon atoms and cycloalkyl radicals of 5 to 6 carbon atoms; is reacted with (2) methylisobutyl ketone to yield in a compound of the general structural formula II; ##STR17## wherein R, R 1 , R 2 , and R 3 are defined as above, the improvement characterized in that the reaction is conducted in one step using a catalyst system that consists of (1) polymer bound anthranilic acid-Pd complex and (2) a bound sulfonic acid resin.
Claim 6
Dependent Claim
141 words
A process wherein (1) a nitrodiphenylamine conforming to the following structural formula: ##STR16## wherein R and R 1 are selected from the group consisting of hydrogen radicals and alkyl radicals of 1 to 9 carbon atoms, R 2 and R 3 are selected from the group consisting of hydrogen radicals, alkyl radicals of 1 to 9 carbon atoms and alkoxy radicals of 1 to 9 carbon atoms and cycloalkyl radicals of 5 to 6 carbon atoms; is reacted with (2) methylisobutyl ketone to yield in a compound of the general structural formula II; ##STR17## wherein R, R 1 , R 2 , and R 3 are defined as above, the improvement characterized in that the reaction is conducted in one step using a catalyst system that consists of (1) polymer bound anthranilic acid-Pd complex and (2) a bound sulfonic acid resin.
Claim 7
Dependent Claim
45 words
A process according to claim 4 wherein the aromatic nitro-containing compound is p-nitrodiphenylamine, the ketone is methylisobutyl ketone, the polymer bound anthranilic acid-Pd complex is a 60/10/30 styrene/vinylbenzyl chloride/divinylbenzene resin that contains from 0.001-10% palladium by weight and the sulfonic acid resin is Amberlyst 15.
Claim 8
Dependent Claim
21 words
A process according to claim 4 wherein the reaction is conducted from 60°-150° C. and at a pressure of 350-7000 kPa.
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) | 1987-07-31 | 1988-01-30 | 1988-07-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-31 | 1992-01-30 | 1992-07-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-31 | 1996-01-30 | 1996-07-31 | $7700.00 | Window Closed / Lapsed |