Nitric Acid → 1-Nitroanthraquinone

HRID 437409Notes

Reaction equation

HRID 437409 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]>>[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

3

Reactant 2

HCID 944Nitric Acid2×HCID 6780Anthraquinone

Product 1

HCID 67041-NitroanthraquinoneYield 99%

Procedure

208 g of anthraquinone are introduced into 1208 g of 99% nitric acid at 0° with stirring (mole ratio 19:1). After a reaction time of 110 minutes at 0°, the temperature is rapidly reduced to -20° to stop the reaction. 1797 g of 63.8% nitric acid (crystallisation acid 77%, γHNO3 = 0.483) are then slowly added for crystallisation. When the crystallised product has been filtered, it is washed with a little 70% nitric acid, freed from nitric acid and subjected to vacuum rectification at 5 Torr and a head temperature of 262°. 176.3 g of 99% 1-nitroanthraquinone are obtained (69% of the theoretical amount).

Workup

  1. customAfter a reaction time of 110 minutes
  2. customat 0°
  3. customis rapidly reduced to -20°
  4. customthe reaction
  5. filtrationWhen the crystallised product has been filtered
  6. washit is washed with a little 70% nitric acid
  7. customa head temperature of 262°

Sources & evidence

ORD record
ord-3938f2ed02c94e0a8053c6f5669cad6c
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

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