Nitric Acid → 1-Nitroanthraquinone

HRID 437411Notes

Reaction equation

HRID 437411 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:17]([O-])([OH:19])=[O:18]>O>[N+:17]([C:8]1[C:7]2[C:6](=[O:16])[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[C:13](=[O:15])[C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 6780Anthraquinone

Product 1

HCID 67041-NitroanthraquinoneYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

208 g of anthraquinone are introduced with stirring into 99% nitric acid which is at a temperature of 45° (955 g, mole ratio 15:1). The isothermal reaction is then stopped after 9 minutes by rapid addition of 100 ml of water. Crystallisation is then brought about by slowly adding a further 105 ml of water (crystallisation acid 79%, γHNO3 = 0.500). The crystallisate is separated, washed with a little 75% nitric acid, freed from nitric acid adhering to it under a vacuum and fractionally distilled under a vacuum (5 Torr, head temperature 265°). 160.4 g of 99.4% pure 1-nitroanthraquinone are obtained (63% of the theoretical amount).

Workup

  1. customis at a temperature of 45° (955 g, mole ratio 15:1)
  2. customThe isothermal reaction
  3. customCrystallisation
  4. additionby slowly adding a further 105 ml of water (crystallisation acid 79%, γHNO3 = 0.500)
  5. customThe crystallisate is separated
  6. washwashed with a little 75% nitric acid
  7. distillationfractionally distilled under a vacuum (5 Torr, head temperature 265°)

Sources & evidence

ORD record
ord-6d41e491b06a48678542ca2c8b871919
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

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