Process for preparing highly pure 5-nitro-1,4,4a,9a-tetrahydroan

Details Process for preparing highly pure 5-nitro-1,4,4a,9a-tetrahydroan Process for preparing highly pure 5-nitro-1,4,4a,9a-tetrahydroan

1975-09-05

1976-05-25

Shaver, Paul F.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C 4968

Patent

active

039593185

ABSTRACT:
Highly pure 5-nitro-1,4,4a,9a-tetrahydroanthraquinone can be obtained by subjecting 6-nitronaphthoquinone-containing crude 5-nitro-1,4-naphthoquinone to Diels-Alder condensation reaction with 1,3-butadiene in a solvent including benzene, an alkylated aromatic hydrocarbon such as toluene, xylene or the like, a halogenated aromatic hydrocarbon such as chlorobenzene, dichlorobenzene, or the like, or a halogenated aliphathic hydrocarbon such as trichloroethylene, perchloroethylene or the like, cooling the resulting reaction solution to crystallize the reaction product, and separating the thus crystallized product by filtration. 5-nitro-1,4,4a,9a-tetrahydroanthraquinone has a relatively small solubility in the above-mentioned solvents, while the solubility of 6-nitro-1,4,4a,9a-tetrahydroanthraquinone in the solvents is rather great, thus the above-mentioned solvents being effective for the separation of these compounds from each other. The oxidation and the subsequent reduction of the thus obtained 5-nitro-1,4,4a,9a-tetrahydroanthraquinone yields 1-aminoanthraquinone with a purity above 98 wt% and a 2-aminoanthraquinone content below 1 wt%. The above-mentioned solvents are also effective for purification of 6-nitro-1,4,4a,9a-tetrahydroanthraquinone-containing 5-nitro-1,4,4a,9a-tetrahydroanthraquinone by recrystallization.

REFERENCES:
patent: 2495222 (1950-01-01), Dawsey et al.
patent: 3838178 (1974-09-01), Vaughan
patent: 3888890 (1975-06-01), Kirchner et al.

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