Nitric Acid → 1-Nitroanthraquinone

HRID 1657489Notes

Reaction equation

HRID 1657489 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]>S1(CCCC1)(=O)=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-Nitroanthraquinone

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

21 g of anthraquinone are introduced into 100 ml of 98 % HNO3 at 20° and the mixture is stirred at this temperature for 8 minutes. 50 ml of sulpholan are then added, the temperature rising to 53°. 40 ml of 98 % HNO3 are distilled off at 35°/10 mm, a further 50 ml of sulpholan are added, the reaction mixture is filtered at 40° and the precipitate is washed with a small quantity of sulpholan and then with water. After drying, 13.9 g of 1-nitro-anthraquinone are obtained, having the following composition:

Workup

  1. customrising to 53°
  2. distillation40 ml of 98 % HNO3 are distilled off at 35°/10 mm
  3. additiona further 50 ml of sulpholan are added
  4. filtrationthe reaction mixture is filtered at 40°
  5. washthe precipitate is washed with a small quantity of sulpholan
  6. customAfter drying

Sources & evidence

ORD record
ord-3af2c433e10c4541904efb1ad0c89c6a
Source dataset
uspto-grants-1976_06
Patent number
US03960903

Reaction notes

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