US3993685A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the production of urethanes
Assignee: Atlantic Richfield Co
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Filing: 1974-10-21
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Granted: 1976-11-23
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Expires: 1994-10-21
Abstract
Abstract A method for the production of a urethane by reacting an organic hydroxyl group-containing compound, carbon monoxide and an organic nitro-compound at a suitable pressure and reaction temperature in the presence of a catalyst system consisting of a mixture of a tertiary amine and a platinum group metal or platinum group metal compound.
Inventors
- 👤 John G. Zajacek
- 👤 John J. McCoy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 00:01
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
145 words
A method for the preparation of urethanes which comprises reacting a hydroxyl group-containing organic compound selected from the group consisting of mono- or polyhydric alcohols and mono- or polyhydric phenols with carbon monoxide and an aromatic, cycloaliphatic or aliphatic mono- or poly-nitro compound at a pressure of between 400 psig and 10,000 psig and at a temperature in the range of about 100° C. to 250° C. in the presence of an effective amount of a catalyst of a mixture of between about 0.005 to 0.20 moles of a platinum group metal or platinum group metal compound and between about 5 to 10 moles of an aliphatic, aromatic or heteroaromatic tertiary amine per mole of said nitro compound, the ratio of the tertiary amine to platinum group metal or platinum group metal compound in the catalyst mixture being between about 1:1 to 25:1 by weight.
Claim 2
Independent Claim
145 words
A method for the preparation of urethanes which comprises reacting a hydroxyl group-containing organic compound selected from the group consisting of mono- or polyhydric alcohols and mono- or polyhydric phenols with carbon monoxide and an aromatic, cycloaliphatic or aliphatic mono- or poly-nitro compound at a pressure of between 400 psig and 10,000 psig and at a temperature in the range of about 100° C. to 250° C. in the presence of an effective amount of a catalyst of a mixture of between about 0.005 to 0.20 moles of a platinum group metal or platinum group metal compound and between about 5 to 10 moles of an aliphatic, aromatic or heteroaromatic tertiary amine per mole of said nitro compound, the ratio of the tertiary amine to platinum group metal or platinum group metal compound in the catalyst mixture being between about 1:1 to 25:1 by weight.
Claim 3
Dependent Claim
28 words
A method according to claim 1 wherein the hydroxyl group-containing compound is selected from the group consisting of ethyl alcohol, methyl alcohol, allyl alcohol, ethylene glycol and phenol.
Claim 4
Dependent Claim
28 words
A method according to claim 1 wherein the carbon monoxide is in amounts of at least 3 moles of carbon monoxide per nitro group in the nitro compound.
Claim 5
Dependent Claim
32 words
A method according to claim 3 wherein the carbon monoxide is employed in amounts of between about 8 moles and 12 moles of carbon monoxide per nitro group in the nitro compound.
Claim 6
Dependent Claim
24 words
A method according to claim 1 wherein the nitro compound is selected from the group consisting of 2,4-dinitrotoluene, 2,6-dinitrotoluene nitrobenzene, 2,4-dinitrochlorobenzene and 1,5- dinitronaphthalene.
Claim 7
Dependent Claim
31 words
A method according to claim 1 wherein the pressure is between about 600 psig and 2000 psig and the temperature is in the range of about 125° C. to 200° C.
Claim 8
Dependent Claim
22 words
A method according to claim 1 wherein the tertiary amine is selected from the group consisting of pyridine, isoquinoline, triethylamine, and 2-chloropyridine.
Claim 9
Dependent Claim
25 words
A method according to claim 1 wherein the platinum group metal compound is a metal halide, oxide, acetate, sulfate, carbonyl or nitrate or mixtures thereof.
Claim 10
Dependent Claim
32 words
A method according to claim 8 wherein the platinum group metal compound is selected from the group consisting of palladium chloride, palladium oxide, palladium acetate, platinum oxide, rhodium chloride and hydridocarbonyl tris(triphenylphosphine)rhodium.
Claim 11
Dependent Claim
26 words
A method according to claim 1 wherein the tertiary amine is employed in amounts sufficient to perform as a solvent and catalyst for the reaction system.
Claim 12
Independent Claim
67 words
A method for the preparation of diethyl toluene-2,4-dicarbamate which comprises reacting ethyl alcohol with carbon monoxide and 2,4-dinitrotoluene at a pressure of between 600 psig and 200 psig and at a temperature in the range of about 125° C. to 200° C. in the presencce of a catalyst consisting of a mixture of a platinum group metal or platinum group metal halide and a heteroaromatic tertiary amine.
Claim 13
Independent Claim
67 words
A method for the preparation of diethyl toluene-2,4-dicarbamate which comprises reacting ethyl alcohol with carbon monoxide and 2,4-dinitrotoluene at a pressure of between 600 psig and 200 psig and at a temperature in the range of about 125° C. to 200° C. in the presencce of a catalyst consisting of a mixture of a platinum group metal or platinum group metal halide and a heteroaromatic tertiary amine.
Claim 14
Dependent Claim
21 words
A method according to claim 11 wherein the platinum group metal halide is palladium chloride and the tertiary amine is pyridine.
Claim 15
Dependent Claim
20 words
A method according to claim 11 wherein the catalyst is a mixture of pyridine and palladium metal supported on charcoal.
Claim 16
Dependent Claim
17 words
A method according to claim 11 wherein the catalyst is a mixture of pyridine and hydridocarbonyl tris(triphenylphosphine)rhodium.
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US3467694A
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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) | 1979-11-23 | 1980-05-24 | 1980-11-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-23 | 1984-05-24 | 1984-11-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-23 | 1988-05-24 | 1988-11-23 | $7700.00 | Window Closed / Lapsed |