Sodium Hydroxide → 1-Aminoanthraquinone

Participants

Reaction Steps

25.7 Grams (0.1 mol) of crude 5-nitrotetrahydroanthraquinone obtained by condensing in ethanol 1,3-butadiene and 5-nitro-1,4-naphthoquinone containing therein 10% of 6-nitro-1,4-naphthoquinone was placed in a reactor having an inner volume of 2 liters together with 514 grams (0.13 mol) of a 1% aqueous sodium hydroxide solution and 0.52 gram of a 5% palladium on carbon catalyst and was hydrogenated with hydrogen at room temperature and under normal pressure with agitation. The hydrogenation reaction was stopped when 0.2 mol of hydrogen was abosrbed. Into the resultant reaction solution was fed air for oxidizing the over-reduced compound formed. The resultant reaction product was separated by filtration together with the catalyst. The thus separated product was mixed with N,N-dimethylformamide for dissolving the product alone, followed by separation of the catalyst by filtration. The resultant filtrate was diluted with water for precipitation to obtain 21 grams of 1-aminoanthraquinone containing therein 2% of 2-aminoanthraquinone (at a yield of 94.2%).

Provenance & Evidence