Patent US4048199A successfully refreshed from Google Patents.
US4048199A
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Production of aminonitrodihydroxyanthraquinones by partial reduction dinitrodihydroxyanthraquinones
Assignee: BASF SE
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Filing: 1976-08-30
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Granted: 1977-09-13
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Expires: 1996-08-30
Abstract
Abstract The production of aminonitrodihydroxyanthraquinones of the formula: ##STR1## in which one X is OH and the other X is NO 2 by partial reduction of the corresponding dinitrodihydroxyanthraquinone or mixtures thereof by heating at 80°-250° C in the presence of 1/2 to 5 times the weight thereof of an unsubstituted or substituted phenol. The reduction is accelerated by being carried out in the presence of a small amount such as 0.5-20 mol percent of an alkaline-reacting agent. Pure aminonitrohydroxyanthraquinones are obtained which are free from diaminodihydroxyanthraquinones.
Inventors
- 👤 Wolfgang Elser
- 👤 Gerhard Epple
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 10:40
CPC Classifications
C; C09; C09B; C09B1/00; C09B1/50; C09B1/503
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
132 words
A process for the production of an aminonitrodihydroxyanthraquinone of the formula: ##STR3## in which one X is hydroxyl and the other X is nitro, by partial reduction, which comprises heating a reaction mixture consisting essentially of 1,5-dinitro-4,8-dihydroxyanthraquinone, 1,8-dinitro-4,5-dihydroxyanthraquinone or a mixture thereof and a reductant selected from the group consisting of unsubstituted phenol, pyrogallol, resorcinol, hydroquinone, hydroquinone monomethyl ether, substituted phenol having on the phenyl nucleus besides the phenolic -OH one or more substituents selected from the group consisting of alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, halogen and amino and mixtures thereof, at from 80° to 250° C until one of the two nitro groups of each respective 1,5-dinitro-4,8-dihydroxyanthraquinone and 1,8-dinitro-4,5-dihydroxyanthraquinone is reduced to the amino group and the reduction product of the above formula is then separated.
Claim 2
Dependent Claim
132 words
A process for the production of an aminonitrodihydroxyanthraquinone of the formula: ##STR3## in which one X is hydroxyl and the other X is nitro, by partial reduction, which comprises heating a reaction mixture consisting essentially of 1,5-dinitro-4,8-dihydroxyanthraquinone, 1,8-dinitro-4,5-dihydroxyanthraquinone or a mixture thereof and a reductant selected from the group consisting of unsubstituted phenol, pyrogallol, resorcinol, hydroquinone, hydroquinone monomethyl ether, substituted phenol having on the phenyl nucleus besides the phenolic -OH one or more substituents selected from the group consisting of alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, halogen and amino and mixtures thereof, at from 80° to 250° C until one of the two nitro groups of each respective 1,5-dinitro-4,8-dihydroxyanthraquinone and 1,8-dinitro-4,5-dihydroxyanthraquinone is reduced to the amino group and the reduction product of the above formula is then separated.
Claim 3
Dependent Claim
22 words
A process as claimed in claim 1 wherein the reduction is carried out at a temperature of from 100° to 180° C.
Claim 4
Dependent Claim
23 words
A process as claimed in claim 1 wherein the reduction is carried out in an excess of said reductant as the reaction medium.
Claim 5
Dependent Claim
24 words
A process as claimed in claim 1 wherein the amount of said reductant is from half to five times the weight of the dinitrodihydroxyanthraquinone.
Claim 6
Dependent Claim
86 words
A process as claimed in claim 1 wherein the reduction is carried out in the presence of 0.5 to 20 mol percent of an alkaline agent selected from the group consisting of an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal carbonate, an alkali metal hydrogen carbonate, an alkali metal acetate, an alkali metal phenolate, an alkaline earth metal phenolate, pyridine, a picoline, quinaldine, quinoline, a secondary or tertiary aliphatic or cycloaliphatic amine, an N,N-dialkyl aniline, piperidine, piperazine, morpholine, hexamethylene imine and thiomorpholine.
Claim 7
Dependent Claim
38 words
A process as claimed in claim 5 wherein said alkaline agent is a member selected from the group consisting of sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium acetate, potassium hydrogen carbonate, pyridine, piperidine, quinoline, morpholine and tributylamine.
Claim 8
Dependent Claim
46 words
A process as claimed in claim 1 wherein said reduction is carried out in an inert organic solvent selected from the group consisting of ethylene glycol, diethylene glycol, diethylene glycol monomethyl ether and monoethyl ether, N-methylpyrrolidone, N,N-dimethylformamide, o-dichlorobenzene, trichlorobenzene, nitrobenzene, naphthalene, the methylnaphthalenes and mixtures thereof.
Claim 9
Dependent Claim
34 words
A process as claimed in claim 7 wherein the heated reaction mixture consists of said dinitrodihydroxyanthraquinone, said reductant in an amount of 1/2 to 5 times the weight of said dinitrodihydroxyanthraquinone, and said solvent.
Claim 10
Dependent Claim
29 words
A process as claimed in claim 1 wherein said substituted phenol is selected from the group consisting of o-cresol, m-cresol, p-cresol, xylenol, o-aminophenol, m-aminophenol, p-aminophenol, p-tert.-butylphenol and mixtures thereof.
Claim 11
Dependent Claim
94 words
A process for the production of 1-amino-5-nitro-4,8-dihydroxyanthraquinone by partial reduction which comprises heating 1,5-dinitro-4,8-dihydroxyanthraquinone in the presence of a reductant selected from the group consisting of unsubstituted phenol, pyrogallol, resorcinol, hydroquinone, hydroquinone monomethyl ether, substituted phenol having on the phenyl nucleus besides the phenolic -OH one or more substituents selected from the group consisting of alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, halogen and amino, and mixtures thereof at from 80° to 250° C until only one nitro group is reduced to the amino group, and the 1-amino-5-nitro-4,8-dihydroxyanthraquinone is then separated.
Claim 12
Dependent Claim
94 words
A process for the production of 1-amino-5-nitro-4,8-dihydroxyanthraquinone by partial reduction which comprises heating 1,5-dinitro-4,8-dihydroxyanthraquinone in the presence of a reductant selected from the group consisting of unsubstituted phenol, pyrogallol, resorcinol, hydroquinone, hydroquinone monomethyl ether, substituted phenol having on the phenyl nucleus besides the phenolic -OH one or more substituents selected from the group consisting of alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, halogen and amino, and mixtures thereof at from 80° to 250° C until only one nitro group is reduced to the amino group, and the 1-amino-5-nitro-4,8-dihydroxyanthraquinone is then separated.
Claim 13
Dependent Claim
22 words
A process as claimed in claim 10 wherein the reduction is carried out at a temperature of from 100° to 180° C.
Claim 14
Dependent Claim
23 words
A process as claimed in claim 10 wherein the reduction is carried out in an excess of said reductant as the reaction medium.
Claim 15
Dependent Claim
24 words
A process as claimed in claim 10 wherein the amount of said reductant is from half to five times the weight of the dinitrodihydroxyanthraquinone.
Claim 16
Dependent Claim
86 words
A process as claimed in claim 10 wherein the reduction is carried out in the presence of 0.5 to 20 mol percent of an alkaline agent selected from the group consisting of an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal carbonate, an alkali metal hydrogen carbonate, an alkali metal acetate, an alkali metal phenolate, an alkaline earth metal phenolate, pyridine, a picoline, quinaldine, quinoline, a secondary or tertiary aliphatic or cycloaliphatic amine, an N,N-dialkyl aniline, piperidine, piperazine, morpholine, hexamethylene imine and thiomorpholine.
Claim 17
Dependent Claim
38 words
A process as claimed in claim 14 wherein said alkaline agent is a member selected from the group consisting of sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium acetate, potassium hydrogen carbonate, pyridine, piperidine, quinoline, morpholine and tributylamine.
Claim 18
Dependent Claim
46 words
A process as claimed in claim 10 wherein said reduction is carried out in an inert organic solvent selected from the group consisting of ethylene glycol, diethylene glycol, diethylene glycol monomethyl ether and monoethyl ether, N-methylpyrrolidone, N,N-dimethylformamide, o-dichlorobenzene, trichlorobenzene, nitrobenzene, naphthalene, the methylnaphthalenes and mixtures thereof.
Claim 19
Dependent Claim
29 words
A process as claimed in claim 10 wherein said substituted phenol is selected from the group consisting of o-cresol, m-cresol, p-cresol, xylenol, o-aminophenol, m-aminophenol, p-aminophenol, p-tert.-butylphenol and mixtures thereof.
References Cited (Backward Citations)
GB322576A
Cited
US2185709A
Cited
US2273966A
Cited
US2485197A
Cited
US2480269A
Cited
GB700044A
Cited
US2819275A
Cited
GB757752A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-12 | 1981-03-14 | 1981-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-12 | 1985-03-14 | 1985-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-12 | 1989-03-14 | 1989-09-13 | $7700.00 | Window Closed / Lapsed |