US4227008A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing aromatic urethanes
Assignee: Mitsui Toatsu Chemicals Inc
•
Filing: 1978-07-25
•
Granted: 1980-10-07
•
Expires: 1998-07-25
Abstract
Abstract Aromatic urethanes can be produced by interacting an aromatic primary amino compound having a nitro group, a nitroso group or a carbamate group, an organic compound having at least one hydroxyl group, and carbon monoxide in the presence of a catalytic system composed of a platinum group metal and/or a compound thereof serving as catalyst and a Lewis acid and/or a compound thereof as promoter under high temperature and high pressure conditions. For instance, the interaction of 2-amino-4-nitrotoluene, ethanol and carbon monoxide in the presence of palladium chloride and a ferrous chloride-pyridine complex under high temperature and high pressure conditions can yield 2,4-diethylcarbamatetoluene.
Inventors
- 👤 Katsuharu Miyata
- 👤 Makoto Aiga
- 👤 Seiji Hasegawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 14:35
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
74 words
A process for producing an aromatic urethane comprising interacting an aromatic primary amino compound having a nitro group, a nitroso group or a carbamate group, an organic compound having at least one hydroxyl group, and carbon monoxide in the presence of a catalytic system comprising a palladium catalyst and a complex of a Lewis acid with a nitrogen-containing aromatic heterocyclic compound or with an organic phosphorus compound under high temperature and high pressure conditions.
Claim 2
Dependent Claim
74 words
A process for producing an aromatic urethane comprising interacting an aromatic primary amino compound having a nitro group, a nitroso group or a carbamate group, an organic compound having at least one hydroxyl group, and carbon monoxide in the presence of a catalytic system comprising a palladium catalyst and a complex of a Lewis acid with a nitrogen-containing aromatic heterocyclic compound or with an organic phosphorus compound under high temperature and high pressure conditions.
Claim 3
Dependent Claim
15 words
A process according to claim 1, wherein said aromatic primary amino compound is a nitroaminotoluene.
Claim 4
Dependent Claim
15 words
A process according to claim 1, wherein said aromatic primary amino compound is an aminocarbamatetoluene.
Claim 5
Dependent Claim
12 words
A process according to claim 1, wherein said catalyst is palladium chloride.
Claim 6
Dependent Claim
13 words
A process according to claim 1, wherein said Lewis acid is ferrous chloride.
Claim 7
Dependent Claim
13 words
A process according to claim 1, wherein said Lewis acid is ferric chloride.
Claim 8
Dependent Claim
30 words
A process according to claim 1, wherein water is added to the reaction system in an amount of 1-70 mole % per mole of the starting aromatic primary amino compound.
Claim 9
Dependent Claim
21 words
A process according to claim 7, wherein said complex is a complex of ferrous chloride with a nitrogen-containing aromatic heterocyclic compound.
Claim 10
Dependent Claim
31 words
A process according to claim 1 wherein said catalyst system is composed of metallic palladium and/or a compound thereof and a complex of ferrous chloride with a nitrogen-containing aromatic heterocyclic compound.
Claim 11
Dependent Claim
35 words
A process according to claim 1 wherein the reaction temperature is in the range of 80° C. to 230° C. and the reaction pressure is in the range of 10 to 1000 kg/cm 2 G.
Claim 12
Dependent Claim
42 words
A process according to claim 1 wherein said catalyst is metallic palladium or a palladium compound selected from the group consisting of palladium halide, cyanide, thiocyanide, isocyanide, oxide, sulfate, nitrate, palladium carbonyl compounds, complexes of palladium with triethylamine, pyridine, isoquinoline, and triphenylphosphine.
Claim 13
Dependent Claim
23 words
A process according to claim 9 wherein said nitrogen-containing aromatic heterocyclic compound is selected from the group consisting of pyridine, quinoline, and isoquinoline.
Claim 14
Dependent Claim
22 words
A process according to claim 1, wherein said organic phosphorous compound is selected from the group consisting of triphenylphosphine, dimethylphenylphosphine and bisdiphenylphosphinoethane.
Claim 15
Dependent Claim
14 words
A process according to claim 1, wherein said complex is a ferrous chloride-pyridine complex.
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) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |