Patent US4629804A successfully refreshed from Google Patents.
US4629804A
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Process for preparation of urethanes
Assignee: Topsoe AS
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Filing: 1985-03-04
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Granted: 1986-12-16
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Expires: 2005-03-04
Abstract
Abstract This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst. The selectivity of this process is increased by the use of methanol instead of various other alkanols, e.g. ethanol. Preferably the catalyst is a halide-free ruthenium catalyst, e.g. a ruthenium carbonyl complex.
Inventors
- 👤 John H. Grate
- 👤 David R. Hamm
- 👤 Donald H. Valentine, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 08:31
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/16
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
68 words
A process for converting a nitrogen-containing organic compound, selected from the group consisting of nitro, nitroso, azo, and azoxy compounds, into the corresponding urethane, by reacting a solution comprising said nitrogen-containing organic compound and methanol with carbon monoxide, which comprises contacting said solution with carbon monoxide, in the presence of a catalyst comprising ruthenium at conditions sufficient to convert said nitrogen-containing organic compound into the said corresponding urethane.
Claim 2
Dependent Claim
68 words
A process for converting a nitrogen-containing organic compound, selected from the group consisting of nitro, nitroso, azo, and azoxy compounds, into the corresponding urethane, by reacting a solution comprising said nitrogen-containing organic compound and methanol with carbon monoxide, which comprises contacting said solution with carbon monoxide, in the presence of a catalyst comprising ruthenium at conditions sufficient to convert said nitrogen-containing organic compound into the said corresponding urethane.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein said nitrogen containing organic compound is a nitro compound.
Claim 4
Dependent Claim
14 words
The process of claim 2 wherein said nitro compound is an aromatic nitro compound.
Claim 5
Dependent Claim
13 words
The process of claim 3 wherein said catalyst comprises a halide-free ruthenium compound.
Claim 6
Dependent Claim
16 words
The process of claim 4 wherein said catalyst comprises a ruthenium compound including a phosphine ligand.
Claim 7
Dependent Claim
26 words
The process of claim 3 wherein said aromatic nitro-compound is selected from the group consisting of nitrobenzene, nitroanisole, dinitrotoluene, dinitrobenzene, nitromesitylene, bis(4-nitrophenyl) methane, nitroaminotoluene and nitrocarboalkoxyaminotoluene.
Claim 8
Dependent Claim
59 words
A process for converting a nitro-containing organic compound into the corresponding urethane, by reacting a solution comprising said nitro-containing organic compound and methanol with carbon monoxide, which comprises contacting said solution with carbon monoxide, in the presence of a catalyst comprising a halide-free ruthenium compound at conditions sufficient to convert said nitro-containing organic compound into the said corresponding urethane.
Claim 9
Dependent Claim
59 words
A process for converting a nitro-containing organic compound into the corresponding urethane, by reacting a solution comprising said nitro-containing organic compound and methanol with carbon monoxide, which comprises contacting said solution with carbon monoxide, in the presence of a catalyst comprising a halide-free ruthenium compound at conditions sufficient to convert said nitro-containing organic compound into the said corresponding urethane.
Claim 10
Dependent Claim
14 words
The process of claim 7 wherein said nitro compound is an aromatic nitro compound.
Claim 11
Dependent Claim
25 words
The process of claim 8 wherein said aromatic nitro-compound is selected from the group consisting of nitrobenzene, nitroanisole, dinitrotoluene, nitromesitylene, bis(4-nitro-phenyl) methane, nitroaminotoluene and nitrocarboalkoxyaminotoluene.
Claim 12
Dependent Claim
14 words
The process of claim 8 wherein said halide-free ruthenium compound comprises a phosphine ligand.
Claim 13
Dependent Claim
12 words
The process of claim 10 wherein said phosphine ligand is bisphosphine ligand.
Claim 14
Dependent Claim
71 words
A process for converting a nitro-containing organic compound into the corresponding urethane, by reacting a solution comprising said nitro-containing organic compound and methanol with carbon monoxide, which comprises the steps of: (a) providing a primary amine in said solution, (b) contacting the solution of step (a) with carbon monoxide, in the presence of a catalyst comprising ruthenium at conditions sufficient to convert said nitrogen-containing organic compound into the said corresponding urethane.
Claim 15
Dependent Claim
71 words
A process for converting a nitro-containing organic compound into the corresponding urethane, by reacting a solution comprising said nitro-containing organic compound and methanol with carbon monoxide, which comprises the steps of: (a) providing a primary amine in said solution, (b) contacting the solution of step (a) with carbon monoxide, in the presence of a catalyst comprising ruthenium at conditions sufficient to convert said nitrogen-containing organic compound into the said corresponding urethane.
Claim 16
Dependent Claim
24 words
The process of claim 12 wherein said nitro-containing organic compound is an aromatic nitro compound and said primary amine is the corresponding aromatic amine.
Claim 17
Dependent Claim
22 words
The process of claim 13 wherein said primary amine is provided by reduction of said nitro-containing compound with hydrogen in said solution.
Claim 18
Dependent Claim
27 words
The process of claim 13 wherein said primary amine is provided by reduction of said nitro-containing compound with hydrogen equivalents derived from the ruthenium-catalyzed water-gas shift reaction.
Claim 19
Dependent Claim
17 words
The process of claim 13 wherein said amine is provided by decomposing a urea or biuret in-situ.
Claim 20
Dependent Claim
13 words
The process of claim 13 wherein said catalyst comprises a halide-free ruthenium compound.
Claim 21
Dependent Claim
14 words
The process of claim 17 wherein said halide-free ruthenium compound comprises a phosphine ligand.
Claim 22
Dependent Claim
26 words
The process of claim 17 wherein said aromatic nitro-compound is selected from the group consisting of nitrobenzene, nitroanisole, dinitrotoluene, dinitrobenzene, nitromesitylene, bis(4-nitrophenyl) methane, nitroaminotoluene and nitrocarboalkoxyaminotoluene.
Claim 23
Dependent Claim
95 words
A process for converting a nitro-containing organic compound into the corresponding urethane, by reacting a solution comprising said nitro-containing organic compound and methanol with carbon monoxide, which comprises the steps of: (a) providing a primary amine in said solution, (b) contacting the solution of step (a) with carbon monoxide, in the presence of a catalyst comprising a halide-free ruthenium compound, at a temperature of at least about 130° C. and a carbon monoxide pressure of at least about 200 psig to convert said nitro-containing organic compound to said corresponding urethane, and (c) recovering said urethane.
Claim 24
Dependent Claim
95 words
A process for converting a nitro-containing organic compound into the corresponding urethane, by reacting a solution comprising said nitro-containing organic compound and methanol with carbon monoxide, which comprises the steps of: (a) providing a primary amine in said solution, (b) contacting the solution of step (a) with carbon monoxide, in the presence of a catalyst comprising a halide-free ruthenium compound, at a temperature of at least about 130° C. and a carbon monoxide pressure of at least about 200 psig to convert said nitro-containing organic compound to said corresponding urethane, and (c) recovering said urethane.
Claim 25
Dependent Claim
23 words
The process of claim 20 wherein said nitro-containing organic compound is an aromatic nitrocompound and said primary amine is the corresponding aromatic amine.
Claim 26
Dependent Claim
26 words
The process of claim 21 wherein said aromatic nitro compound is selected from the group consisting of nitrobenzene, nitroanisole, dinitrotoluene, dinitrobenzene, nitromesitylene, bis(4-nitrophenyl)methane, nitroaminotoluene and nitrocarboalkoxyaminotoluene.
Claim 27
Dependent Claim
18 words
The process of claim 22 wherein said nitro-containing organic compound is nitrobenzene and said primary amine is aniline.
Claim 28
Dependent Claim
14 words
The process of claim 21 wherein said halide-free ruthenium compound comprises a phosphine ligand.
Claim 29
Dependent Claim
13 words
The process of claim 24 wherein said phosphine ligand is a bisphosphine ligand.
Claim 30
Dependent Claim
11 words
The process of claim 25 wherein said phosphine ligand is bis(1,2-diphenylphosphino)benzene.
References Cited (Backward Citations)
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