US4089867A
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Preparation of diacylfurazan oxides
Assignee: Texaco Inc
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Filing: 1976-11-11
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Granted: 1978-05-16
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Expires: 1996-11-11
Abstract
Abstract Diacylfurazan oxides are prepared by catalytic dimerization of alpha-nitroketones.
Inventors
- 👤 Roger G. Duranleau
- 👤 John M. Larkin
- 👤 Stanley R. Newman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 11:31
CPC Classifications
C; C07; C07D; C07D271/00; C07D271/02; C07D271/08; Y; Y10; Y10S; Y10S423/00; Y10S423/09; Y10S423/14
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
104 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR3## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR4## where R is as defined above with catalytic amounts of an organic acid having 2 to 18 carbon atoms and a pk a of about 4.0 to about 0.5 in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 2
Independent Claim
104 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR3## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR4## where R is as defined above with catalytic amounts of an organic acid having 2 to 18 carbon atoms and a pk a of about 4.0 to about 0.5 in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 3
Dependent Claim
21 words
A method according to claim 1 wherein said contacting is conducted at a temperature of from about 80° to 110° C.
Claim 4
Dependent Claim
11 words
A method according to claim 1 wherein said nitroketone is 1-nitro-2-hexadecanone.
Claim 5
Dependent Claim
11 words
A method according to claim 1 wherein said nitroketone is 1-nitro-2-tetradecanone.
Claim 6
Dependent Claim
11 words
A method according to claim 1 wherein said nitroketone is 1-nitro-2-decanone.
Claim 7
Dependent Claim
11 words
A method according to claim 1 wherein said nitroketone is omega-nitroacetophenone.
Claim 8
Independent Claim
112 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR5## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR6## where R is as defined above with catalytic amounts of an organic acid having a pk a of about 4.0 to about 0.5 wherein said acid is an alpha-halogenated alkanoic acid of 2 to 5 carbon atoms in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 9
Independent Claim
112 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR5## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR6## where R is as defined above with catalytic amounts of an organic acid having a pk a of about 4.0 to about 0.5 wherein said acid is an alpha-halogenated alkanoic acid of 2 to 5 carbon atoms in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 10
Independent Claim
112 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR7## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR8## where R is as defined above with catalytic amounts of an organic acid having a pk a of about 4.0 to about 0.5 wherein said acid is an aromatic nitro acid of 7 to 11 carbon atoms in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 11
Independent Claim
112 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR7## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR8## where R is as defined above with catalytic amounts of an organic acid having a pk a of about 4.0 to about 0.5 wherein said acid is an aromatic nitro acid of 7 to 11 carbon atoms in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 12
Independent Claim
112 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR9## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR10## where R is as defined above with catalytic amounts of an organic acid having a pk a of about 4.0 to about 0.5 wherein said acid is an organic sulfonic acid of 6 to 18 carbon atoms in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 13
Independent Claim
112 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR9## where R is an alkyl group having 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR10## where R is as defined above with catalytic amounts of an organic acid having a pk a of about 4.0 to about 0.5 wherein said acid is an organic sulfonic acid of 6 to 18 carbon atoms in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 14
Dependent Claim
12 words
A method according to claim 1 wherein said acid is p-toluenesulfonic acid.
Claim 15
Dependent Claim
11 words
A method according to claim 1 wherein said solvent is toluene.
Claim 16
Dependent Claim
11 words
A method according to claim 1 wherein said solvent is benzene.
Claim 17
Dependent Claim
15 words
A method according to claim 1 wherein byproduct water is continuously separated from the reaction.
Claim 18
Dependent Claim
13 words
A method according to claim 1 wherein said furazan oxide is 3,4-dioctanoylfurazan oxide.
Claim 19
Independent Claim
94 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR11## where R is an alkyl group having 1 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR12## where R is as defined above with catalytic amounts of an organic acid having 2 to 18 carbon atoms and a pk a of about 4.0 to about 0.5 in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 20
Independent Claim
94 words
A method for the preparation of diacylfurazan oxides corresponding to the formula: ##STR11## where R is an alkyl group having 1 to 20 carbon atoms which comprises contacting an alpha-nitroketone or a mixture of alpha-nitroketones of the formula: ##STR12## where R is as defined above with catalytic amounts of an organic acid having 2 to 18 carbon atoms and a pk a of about 4.0 to about 0.5 in the substantial absence of added water and in the presence of a non-reactive, non-polar solvent at a temperature of from about 50° to 150° C.
Claim 21
Dependent Claim
13 words
A method according to claim 15 wherein said furazan oxide is 3,4-dipentadecanoylfurazan oxide.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-15 | 1981-11-14 | 1982-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-15 | 1985-11-14 | 1986-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-15 | 1989-11-14 | 1990-05-16 | $7700.00 | Window Closed / Lapsed |