US4454322A
Expired / Lapsed
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Process for the preparation of 2-benzoxazolone and derivatives from ortho-nitrophenols and carbon monoxide
Assignee: Arkema France SA
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Filing: 1983-01-24
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Granted: 1984-06-12
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Expires: 2003-01-24
Abstract
Abstract Process for the preparation of 2-benzoxazolone and derivatives by the reaction, in the liquid phase, at a temperature from 100° to 500° C. and a pressure from 20 to 500 bars, of an ortho-nitrophenol of the formula: ##STR1## in which R represents a hydrogen or halogen atom, an alkyl group containing from 1 to 10 carbon atoms or an alkoxy group OR' in which R' represents an alkyl group containing from 1 to 10 carbon atoms, and carbon monoxide under pressure, characterized in that the process is carried out in the presence of a. a supported catalyst formed by the association of a noble metal of Group VIII and a second transition metal selected from Groups, V b , VI b or VIII of the Periodic Classification, in the metallic or oxide form, and b. a nitrogenous heteroaromatic base; the process may be carried out in the presence of a solvent.
Inventors
- 👤 Jacques Kervennal
- 👤 Jean-Marie Cognion
- 👤 Pierre Durual
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 22:21
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C07D263/54; C07D263/58
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
127 words
A process for the preparation of 2-benzoxazolone and derivatives thereof which comprises reacting, in the liquid phase, at a temperature from 100° to 500° C. and a pressure of 20 to 500 bars, an ortho-nitrophenol of the formula: ##STR4## in which R represents hydrogen or halogen, alkyl containing from 1 to 10 carbon atoms, alkoxy in which the alkyl group contains from 1 to 10 carbon atoms, and carbon monoxide under pressure, the process being carried out in the presence of: a. a supported catalyst formed by the association of a noble metal of Group VIII and a second transition metal selected from Groups V b , VI b or VIII of the Periodic Classification, in the metallic or oxide form; and b. a nitrogenous heteroaromatic base.
Claim 2
Dependent Claim
127 words
A process for the preparation of 2-benzoxazolone and derivatives thereof which comprises reacting, in the liquid phase, at a temperature from 100° to 500° C. and a pressure of 20 to 500 bars, an ortho-nitrophenol of the formula: ##STR4## in which R represents hydrogen or halogen, alkyl containing from 1 to 10 carbon atoms, alkoxy in which the alkyl group contains from 1 to 10 carbon atoms, and carbon monoxide under pressure, the process being carried out in the presence of: a. a supported catalyst formed by the association of a noble metal of Group VIII and a second transition metal selected from Groups V b , VI b or VIII of the Periodic Classification, in the metallic or oxide form; and b. a nitrogenous heteroaromatic base.
Claim 3
Dependent Claim
26 words
The process according to claim 1 in which the concentration by weight of the noble metal on the support varies from 0.1 to 20% by weight.
Claim 4
Dependent Claim
24 words
The process according to claim 1 in which the concentration by weight of the noble metal on the support varies from 1 to 15%.
Claim 5
Dependent Claim
27 words
The process according to claim 1 in which the atomic ratio of the second metal to the noble metal varies from 10 -2 to 10 2 .
Claim 6
Dependent Claim
24 words
The process according to claim 1 in which the atomic ratio of the second metal to the noble metal varies from 0.1 to 10.
Claim 7
Dependent Claim
44 words
The process according to claim 1 in which the concentration of the catalyst in the reaction medium, expressed as the ratio of the number of gram-atoms of noble metal to the number of nitro groups to be converted, varies from 10 -4 to 1.
Claim 8
Dependent Claim
46 words
The process according to claim 1 in which the concentration of the catalyst in the reaction medium, expressed as the ratio of the number of gram-atoms of noble metal to the number of nitro groups to be converted, varies from 5.10 -3 to 10 -1 .
Claim 9
Dependent Claim
27 words
The process according to claim 1 in which the nitrogenous heteroaromatic base is introduced at concentrations from 10 -2 to 30 moles per mole of nitro derivative.
Claim 10
Dependent Claim
26 words
The process according to claim 1 in which the nitrogenous heteroaromatic base is introduced at concentrations from 0.1 to 10 moles per mole of nitro derivative.
Claim 11
Dependent Claim
16 words
The process according to claim 1 in which the nitrogenous heteroaromatic base is pyridine or quinoline.
Claim 12
Dependent Claim
20 words
The process according to claim 1 in which the noble metal is palladium and the second transition metal is molybdenum.
Claim 13
Dependent Claim
19 words
The process according to claim 1 in which the process is carried out in the presence of a solvent.
Claim 14
Dependent Claim
23 words
The process according to claim 12 in which solutions containing 5 to 50% by weight of nitro derivative in the solvent are used.
Claim 15
Dependent Claim
55 words
The process according to claim 12 in which the solvent is a saturated or aromatic hydrocarbon selected from hexane, heptane, n-decane, decalin, benzene, toluene and xylene; an aromatic halide selected from chlorobenzene and its dichloro derivatives; a nitrogenous heterocyclic selected from pyridine and bipyridine; a fluorinated solvent selected from perfluorinated methyl decalin and trichlorotrifluoro ethane.
Claim 16
Dependent Claim
23 words
The process according to claim 14 in which solutions containing 5 to 50% by weight of nitro derivative in the solvent are used.
Claim 17
Dependent Claim
20 words
Process according to claim 1 in which the catalyst supports are aluminas, silicas, silica-aluminas, magnesia, active charcoal or silicon carbides.
Claim 18
Dependent Claim
51 words
The process according to claim 12 in which the solvent is a saturated hydrocarbon containing from 6 to 12 carbon atoms, an aromatic hydrocarbon containing from 6 to 12 carbon atoms, an aromatic halide, a nitrogenous hetrocyclic wherein the heterocycles contain from 3 to 5 carbon atoms or a fluorinated solvent.
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) | 1987-06-12 | 1987-12-12 | 1988-06-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-06-12 | 1991-12-12 | 1992-06-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-06-12 | 1995-12-12 | 1996-06-12 | $7700.00 | Window Closed / Lapsed |