US4020052A
Expired / Lapsed
US
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Treatment of aromatic amines with gas mixtures derived from the oxidation of ammonia to effect diazotization/coupling
Assignee: EIDP Inc
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Filing: 1975-11-25
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Granted: 1977-04-26
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Expires: 1995-11-25
Abstract
Abstract 1,3-Diaryl triazenes, e.g., 1,3-diphenyltriazene, intermediates in the synthesis of aromatic diamines, e.g., p-phenylenediamine, are prepared by catalytically oxidizing ammonia, and subsequently the resulting nitric oxide, with a gas comprising diluted molecular oxygen, e.g., air, so as to produce a gas mixture containing dilute NO x , i.e., NO 2 preferably admixed with NO, x being (1 + n), wherein n is the NO 2 fraction of the NO x ; and contacting the gas mixture, preferably at a temperature in the range of about from 25° to 350° C., with excess primary aromatic monoamine, e.g., aniline, so as to result in a monoamine temperature in the range of about from 25° to 90° C., preferably 40° to 60° C., during contact. Highest yields of triazene are obtained when the x in NO x is about from 1.3 to 1.7, and the amount of NO x gas mixture contacted with the monoamine and the time of contact are such that at least about 60% by weight of the monoamine remains unconsumed. A gas mixture temperature just prior to gas contact with the liquid monoamine in the range of about from 110° to 275° C. is more preferred under certain circumstances.
Inventors
- 👤 John Kent Detrick
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 21:45
CPC Classifications
C; C01; C01B; C01B21/00; C01B21/20; C01B21/24; C01B21/26
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
130 words
A method of preparing a 1,3-diaryl triazene comprising, in sequence, catalytically oxidizing ammonia by means of a gas comprising diluted molecular oxygen so as to form a gas mixture comprising a dilute nitrogen oxide component selected from the group consisting of nitrogen dioxide (NO 2 ) and mixtures of nitrogen dioxide and nitric oxide, said nitrogen oxide component being represented by the formula NO x wherein x is (1 + n), n being the NO 2 fraction of the nitrogen oxide component; and contacting said gas mixture with a primary carbocyclic aromatic monoamine in the liquid phase so as to result in a monoamine temperature in the range of about from 25° C. to 90° C. during contact, while maintaining at least about 5 percent by weight of unconsumed monoamine.
Claim 2
Independent Claim
130 words
A method of preparing a 1,3-diaryl triazene comprising, in sequence, catalytically oxidizing ammonia by means of a gas comprising diluted molecular oxygen so as to form a gas mixture comprising a dilute nitrogen oxide component selected from the group consisting of nitrogen dioxide (NO 2 ) and mixtures of nitrogen dioxide and nitric oxide, said nitrogen oxide component being represented by the formula NO x wherein x is (1 + n), n being the NO 2 fraction of the nitrogen oxide component; and contacting said gas mixture with a primary carbocyclic aromatic monoamine in the liquid phase so as to result in a monoamine temperature in the range of about from 25° C. to 90° C. during contact, while maintaining at least about 5 percent by weight of unconsumed monoamine.
Claim 3
Dependent Claim
25 words
A method of claim 1 wherein said primary carbocyclic aromatic monoamine is selected from the group consisting of unsubstituted, alkyl-substituted, and halo-substituted aniline and naphthylamines.
Claim 4
Dependent Claim
40 words
A method of claim 1 wherein ammonia is oxidized at a temperature in the range of 800° to 950° C. and the resulting gas is cooled to a temperature below about 500° C. so as to form said gas mixture.
Claim 5
Dependent Claim
42 words
A method of claim 3 wherein said gas comprising diluted molecular oxygen is air, the NO x content of the gas mixture is about from 10 to 12 mole percent, and x is in the range of from about 1.1 to 2.0.
Claim 6
Dependent Claim
19 words
A method of claim 4 wherein said nitrogen oxide component is a mixture of nitrogen dioxide and nitric oxide.
Claim 7
Dependent Claim
17 words
A method of claim 5 wherein x is in the range of about from 1.3 to 1.7.
Claim 8
Dependent Claim
31 words
A method of claim 6 wherein the temperature of said gas mixture just prior to its contact with the monoamine is in the range of about from 25° to 350° C.
Claim 9
Dependent Claim
34 words
A method of claim 7 wherein the temperature at which said monoamine is maintained while it is in contact with said mixture is in the range of about from 40° C. to 60° C.
Claim 10
Dependent Claim
37 words
A method of claim 7 wherein the amount of said gas mixture contacted with said monoamine and the time of said contact are such that at least about 40 percent by weight of unconsumed monoamine is maintained.
Claim 11
Dependent Claim
14 words
A method of claim 7 wherein said gas mixture is contacted with neat monoamine.
Claim 12
Dependent Claim
37 words
A method of claim 10 wherein the amount of said gas mixture contacted with said monoamine and the time of said contact are such that at least about 60 percent by weight of unconsumed monoamine is maintained.
Claim 13
Independent Claim
147 words
A method of preparing 1,3-diphenyltriazene comprising, in sequence, catalytically oxidizing ammonia by means of air so as to form a gas mixture comprising a mixture of nitrogen dioxide and nitric oxide as a nitrogen oxide component, said nitrogen oxide component being represented by the formula NO x wherein x is (1 + n), n being the NO 2 fraction of the nitrogen oxide component, and is in the range of about from 1.3 to 1.7, the NO x content of said gas mixture about from 10 to 12 percent; and contacting said gas mixture at a temperature in the range of about from 25° C to 350° C with aniline in the liquid phase so as to result in an aniline temperature in the range of about from 25° C. to 90° C. during contact, while maintaining at least about 40 percent by weight of unconsumed aniline.
Claim 14
Independent Claim
147 words
A method of preparing 1,3-diphenyltriazene comprising, in sequence, catalytically oxidizing ammonia by means of air so as to form a gas mixture comprising a mixture of nitrogen dioxide and nitric oxide as a nitrogen oxide component, said nitrogen oxide component being represented by the formula NO x wherein x is (1 + n), n being the NO 2 fraction of the nitrogen oxide component, and is in the range of about from 1.3 to 1.7, the NO x content of said gas mixture about from 10 to 12 percent; and contacting said gas mixture at a temperature in the range of about from 25° C to 350° C with aniline in the liquid phase so as to result in an aniline temperature in the range of about from 25° C. to 90° C. during contact, while maintaining at least about 40 percent by weight of unconsumed aniline.
Claim 15
Dependent Claim
46 words
A method of claim 12 wherein said gas mixture is contacted with neat aniline, and the amount of said gas mixture contacted with said aniline and the time of said contact are such that at least about 60 percent by weight of unconsumed aniline is maintained.
Claim 16
Dependent Claim
17 words
A method of claim 5 wherein said primary carbocyclic aromatic monoamine is aniline or o- or m-toluidine.
References Cited (Backward Citations)
US2133037A
Cited
US2894942A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-25 | 1980-10-25 | 1981-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-25 | 1984-10-25 | 1985-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-25 | 1988-10-25 | 1989-04-26 | $7700.00 | Window Closed / Lapsed |