Nitric Acid → 1-Nitroanthraquinone

HRID 1657490Notes

Reaction equation

HRID 1657490 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>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

5

Reactant 3

HCID 944Nitric AcidHCID 6780AnthraquinoneHCID 31347Sulfolane

Product 1

HCID 67041-Nitroanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 g of anthraquinone are introduced into 100 ml of 98 % HNO3 at 0°, the temperature rising to 10° in two minutes as a result of this addition. The reaction mixture is then nitrated at 10° for 20 minutes, with cooling by iced water. 100 ml of sulpholan are added, the temperature rising to 50° as a result. The reaction mixture is suction-filtered at 20° and the precipitate is washed with 50 ml of sulpholan and then with water, and dried. 12.7 g of 1-nitro-anthraquinone, formed by analysis to have the following composition, are obtained:

Workup

  1. customas a result of this addition
  2. waitThe reaction mixture is then nitrated at 10° for 20 minutes
  3. customrising to 50° as a result
  4. filtrationThe reaction mixture is suction-filtered at 20°
  5. washthe precipitate is washed with 50 ml of sulpholan
  6. dry with materialwith water, and dried

Sources & evidence

ORD record
ord-7a3e16e0dd284fbe84fe78b0ace7ca41
Source dataset
uspto-grants-1976_06
Patent number
US03960903

Reaction notes

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