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US4286105A
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Process for the preparation of antioxidant amides
Assignee: Goodyear Tire and Rubber Co
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Filing: 1979-11-09
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Granted: 1981-08-25
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Expires: 1999-11-09
Abstract
Abstract An inexpensive and nonhazardous process for the preparation of an amide wherein an organic acid reacting with an aryl amine to form an intermediate hydroxy aryl amide and then dehydrating the hydroxy aryl amide to form a α, β unsaturated amide.
Inventors
- 👤 Dane K. Parker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 15:09
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/34; C07C233/16; C08; C08F; C08F236/00; C08F236/02; C08F236/04
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
230 words
An improved process for the synthesis of a α,β unsaturated aryl amides comprising reacting an organic acid having general formula I: ##STR5## wherein R 1 is selected from the group consisting of hydrogen, methyl or phenyl radicals; with an aryl amine selected from one of the following structural formulae: ##STR6## wherein R 2 and R 3 are the same or different alkyl radicals selected from the group consisting of isopropyl, secondary butyl, tert.-butyl, tert.-pentyl or tert.-hexyl; R 4 and R 5 are the same or different radicals selected from the group consisting of hydrogen, methyl or ethyl; and R 6 is selected from a phenyl radical or an alkyl substituted phenyl radical with one to three same or different alkyl substituents selected from either methyl or ethyl radicals; to produce a hydroxy aryl amide having one of the following structural formulae: ##STR7## wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined as above, and (B) dehydrating, through use of concentrated sulfuric acid at a temperature of 98°-110° C. in at least a 1 to 1 molar ratio, the hydroxy aryl amide to form an α, β unsaturated amide having one of the following structural formulae: ##STR8## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are defined as above.
Claim 2
Dependent Claim
230 words
An improved process for the synthesis of a α,β unsaturated aryl amides comprising reacting an organic acid having general formula I: ##STR5## wherein R 1 is selected from the group consisting of hydrogen, methyl or phenyl radicals; with an aryl amine selected from one of the following structural formulae: ##STR6## wherein R 2 and R 3 are the same or different alkyl radicals selected from the group consisting of isopropyl, secondary butyl, tert.-butyl, tert.-pentyl or tert.-hexyl; R 4 and R 5 are the same or different radicals selected from the group consisting of hydrogen, methyl or ethyl; and R 6 is selected from a phenyl radical or an alkyl substituted phenyl radical with one to three same or different alkyl substituents selected from either methyl or ethyl radicals; to produce a hydroxy aryl amide having one of the following structural formulae: ##STR7## wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined as above, and (B) dehydrating, through use of concentrated sulfuric acid at a temperature of 98°-110° C. in at least a 1 to 1 molar ratio, the hydroxy aryl amide to form an α, β unsaturated amide having one of the following structural formulae: ##STR8## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are defined as above.
Claim 3
Dependent Claim
26 words
A process as described in claim 1 above wherein the organic acid is select from the group consisting of α-hydroxy-isobutyric acid, α-hydroxy-propionic acid, and 2-phenyl-2-hydroxy-propionic acid.
Claim 4
Dependent Claim
25 words
A process as described in claim 1 wherein the aromatic amine is selected from the group consisting of 4-aminodiphenylamine, 2-methyl-4-aminodiphenylamine, 2,5-dimethyl-4-aminodiphenylamine, 2-ethyl-4-aminodiphenylamine, 2,6-di-tert.butyl-4-aminophenol, and 2,6-diisopropyl-4-aminophenol.
Claim 5
Dependent Claim
43 words
A process as described in claim 1 wherein the organic acid is selected from the group consisting of α-hydroxy-isobutyric acid, α-hydroxy-propionic acid, and 2-phenyl-2-hydroxy-propionic acid and the aromatic amine is selected from the group consisting of 4-aminodiphenylamine, 2-methyl-4-aminodiphenylamine, 2,5-dimethyl-4-aminodiphenylamine, 2-ethyl-4-aminodiphenylamine, 2,6-di-tert.butyl-4-aminophenol, and 2,6-diisopropyl-4-aminophenol.
Claim 6
Dependent Claim
32 words
A process described in claim 1 wherein the acid is α-hydroxy-isobutyric acid, the amine is 4-aminodiphenylamine and the reaction takes place in xylene solvent in the presence of an added acid catalyst.
Claim 7
Dependent Claim
25 words
A process in which 4-aminodiphenylamine and a 5% molar excess of α-hydroxy-isobutyric acid undergoes a condensation reaction at 150° to 250° C. without a solvent.
Claim 8
Dependent Claim
25 words
A process in which 4-aminodiphenylamine and a 5% molar excess of α-hydroxy-isobutyric acid undergoes a condensation reaction at 150° to 250° C. without a solvent.
Claim 9
Dependent Claim
24 words
A process as described in claim 6 wherein the final product is dehydrated using concentrated sulfuric acid as the solvent and the dehydrating agent.
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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) | 1984-08-24 | 1985-02-23 | 1985-08-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-24 | 1989-02-23 | 1989-08-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-24 | 1993-02-23 | 1993-08-25 | $7700.00 | Window Closed / Lapsed |