56613-39-9

Upstream product

• 82-34-8 1-nitroanthraquinone 
• 110-86-1 pyridine 
• 7783-06-4 hydrogen sulfide 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 71-43-2 benzene 
• 56281-39-1 5-nitro-1,4,4a,9a-tetrahydro-anthraquinone 
• 54401-95-5 1-nitroso-anthraquinone 

Downstream Products

• 116-85-8 4-hydroxy-1-aminoanthraquinone 
• 82-45-1 1-amino-9,10-anthracenedione 

Relevant academic research and scientific papers

Synthesis method 1 -aminoanthraquinone

The invention belongs to the technical field of dye intermediate synthesis, and particularly relates 1 - hydroxyaminoanthraquinone synthesis method which comprises dissolving 1 -nitroanthraquinone in a mixed solution N, N - dimethyl formamide and water, and then reducing the sodium borohydride to obtain the target product 1 - hydroxyanthraquinone. The volume ratio of N, N -dimethylformamide to water in the mixed solution was 0.5: 1 - 3:1. A mixture solution of N, N - dimethyl formamide and water and a mass ratio 1 - nitroanthraquinone of 100:1 - 600:1. The molar ratio of sodium borohydride to 1 -nitroanthraquinone 0.5: 1 - 10:1. Reaction temperature is 10 - 90 °C. The reaction time is 5 - 60 min. The method is mild in reaction condition, short in reaction time and high in 1 - hydroxyl amino anthraquinone product yield, and has the characteristics of greenness, safety and high efficiency.

PHOTOCHEMICAL HYDROXYLATION OF ANTHRAQUINONE IN SULFURIC ACID

The photolysis of anthraquinone in sulfuric acid leads to hydroxylation of its ring with the preferential formation of 2-hydroxyanthraquinone in concentrated and 1-hydroxyanthraquinone in dilute sulfuric acid.The second hydroxy group only enters photochemically at position 4 of 1-hydroxyanthraquinone if the latter is activated by complex formation with boric acid.During photolysis in deaerated sulfuric acid the nitroanthraquinones are reduced photochemically to (hydroxyamino)anthraquinones; here 1-(hydroxyamino)anthraquinones with an unoccupied para position in the same condensed benzene ring undergo rearrangement under the reaction conditions to 1-amino-4-hydroxyanthraquinones.The main photochemical stage of hydroxylation in concentrated sulfuric acid is nucleophilic substitution of hydrogen in the monoprotonated anthraquinone by the HSO4(-) ion, while in dilute sulfuric acid it is electron transfer from water to anthraquinone.

Process for the preparation of 1-substituted anthraquinones

A process for the preparation of 1-substituted anthraquinones represented by the general formula I EQU1 where, in the formula, R1 and R2 represent individually a hydrogen atom or methyl group and X represents a hydroxylamino or amino group, Which comprises treating in a liquid medium a 5-nitro-1,4,4a,9a-tetrahydroanthraquinone represented by the general formula II EQU2 where, in the general formula, R1 and R2 represent individually a hydrogen atom or methyl group, In the presence of a basic compound with or without a reducing agent.