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US4222935A
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Process for the manufacture of aromatic nitriles
Assignee: Imperial Chemical Industries Ltd
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Filing: 1979-07-27
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Granted: 1980-09-16
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Expires: 1999-07-27
Abstract
Abstract A process for the manufacture of aromatic nitriles by reacting an aromatic halogen compound with formamide and the anhydride of a monocarboxylic acid in the presence of a copper catalyst and an acid-binding agent. Particularly applicable to replacement of halogen ortho to the azo linkage of an azo dyestuff by cyano.
Inventors
- 👤 Antony Greenall
- 👤 Raymond Price
- 👤 Peter M. Quan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 23:09
CPC Classifications
C; C09; C09B; C09B43/00; C09B43/40; C09B43/42
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
42 words
A process for the manufacture of aromatic nitriles which comprises reacting an aromatic halide which is a chlorine, bromine or iodine compound with formamide and the anhydride of a monocarboxylic acid in the presence of a copper catalyst and an acid-binding agent.
Claim 2
Dependent Claim
42 words
A process for the manufacture of aromatic nitriles which comprises reacting an aromatic halide which is a chlorine, bromine or iodine compound with formamide and the anhydride of a monocarboxylic acid in the presence of a copper catalyst and an acid-binding agent.
Claim 3
Dependent Claim
29 words
A process as claimed in claim 1 wherein from 2 to 20 mols of formamide and of the carboxylic acid anhydride are used per mol of the aromatic halide.
Claim 4
Dependent Claim
24 words
A process as claimed in claim 1 wherein from 2 to 10 mols of acid-binding agent are used per mol of the aromatic halide.
Claim 5
Dependent Claim
24 words
A process as claimed in claim 1 wherein from 0.01 to 1.0 mols of copper catalyst are used per mol of the aromatic halide.
Claim 6
Dependent Claim
15 words
A process as claimed in claim 1 wherein the copper catalyst is copper (I) iodide.
Claim 7
Dependent Claim
20 words
A process as claimed in claim 1 wherein the reaction is carried out in the presence of a non-hydroxylic solvent.
Claim 8
Dependent Claim
15 words
A process as claimed in claim 1 wherein the reaction temperature is at least 75°C.
Claim 9
Dependent Claim
16 words
A process as claimed in claim 1 wherein the aromatic halogen compound is an azo dyestuff.
Claim 10
Dependent Claim
186 words
A process as claimed in claim 8 wherein the azo dyestuff has the formula: ##STR3## wherein X and Y each individually represent a hydrogen atom, a halogen atom, or a lower alkyl, lower alkoxy, cyano, nitro, sulphone, optionally substituted sulphamoyl optionally substituted carbamoyl or alkoxycarbonyl group; Z represents a hydrogen atom or a lower alkyl, lower alkoxy, lower alkylamino or --NR 2 CO.T group in which R 2 represents a hydrogen atom or a lower alkyl group and T represents a hydrocarbon radical, an amino group or a group --NHQ or --OQ in which Q represents a hydrocarbon radical; U represents a hydrogen atom, a halogen atom or a lower alkyl, lower alkoxy, sulphone or nitro group, provided that U is not a sulphone or nitro group when either of X and Y is a nitro, sulphone or optionally substituted sulphamoyl group; V represents a hydrogen atom, a halogen atom or a lower alkyl or lower alkoxy group; R represents a hydrogen atom or an optionally substituted hydrocarbon radical; R 1 represents an optionally substituted hydrocarbon radical; and W represents a chlorine, bromine or iodine atom.
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) | 1983-09-16 | 1984-03-17 | 1984-09-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-16 | 1988-03-17 | 1988-09-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-16 | 1992-03-17 | 1992-09-16 | $7700.00 | Window Closed / Lapsed |