1-Nitroanthraquinone → 1-Nitroanthraquinone
Reaktionsgleichung
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+](C1C=CC=C2C=1C(=O)C=CC2=O)([O-])=O.[N+](C1C(=O)C2C(C(=O)C=1)=CC=CC=2)([O-])=O.[N+](C1C=C2C(=CC=1)C(=O)C1CCCCC=1C2=O)([O-])=O>>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1.[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]Komponenten
Versuchsvorschrift
In the process of the French Pat. No. 1,486,803, 5-nitrotetrahydroanthraquinone produced is directly subjected to oxidation, without isolation from reaction system, into 1-nitroanthraquinone. Accordingly, when crude 5-nitronaphthoquinone is used as a starting material, 6-nitroanaphthoquinone is converted into 2-nitronaphthoquinone through 6-nitrotetrahydroanthraquinone, thus contaminating 1-nitroanthraquinone and lowering the purity thereof. Further, it is difficult to obtain highly pure 1-aminoanthraquinone from the thus contaminated 1-nitroanthraquinone. This process also requires an additional step of purifying the starting material or the product so as to obtain highly pure 1-nitroanthraquinone or 1-aminoanthraquinone. In this connection, we have found as a result of an experiment that when crude 5-nitronaphthoquinone is condensed with 1,3-butadiene in nitrobenzene and the resulting product is separated or isolated from the reaction system by filtration, most of 6-nitrotetrahydroanthraquinone produced from 6-nitronaphthoquinone is removed in a state of being dissolved in the solvent, so that there can be obtained highly pure 5-nitrotetrahydroanthraquinone, from which 1-nitroanthraquinone or 1-aminoanthraquinone with high purity can be prepared. However, this process is also industrially disadvantageous in that the dissolution loss of 5-nitrotetrahydroanthraquinone in solvent is large, it's yield being considerably reduced.
Quellen und Nachweise
- ORD-Eintrag
- ord-048dbb69d318422284654623a19e1139
- Quelldatensatz
- uspto-grants-1976_05
- Patentnummer
- US03959318
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