Nitric Acid → 1-Nitroanthraquinone

HRID 437410Notes

Reaction equation

HRID 437410 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 AcidHCID 6780Anthraquinone

Product 1

HCID 67041-NitroanthraquinoneYield 98.5%

Conditions

Temperature
75 °C

Procedure

A mixture of 208 g of anthraquinone and 382 g of 99% nitric acid (mole ratio 6:1) is heated to 75° C for 10 hours with stirring and then slowly cooled to -10° (γHNO3 = 0.695). The precipitated product is filtered off, washed with a little 75% nitric acid, freed from nitric acid adhering to it by evaporation under vacuum, and fractionally distilled at 6 Torr and 267° head temperature. 151.5 g of 98.5% pure 1-nitroanthraquinone are obtained (59% of the theoretical amount).

Workup

  1. temperatureslowly cooled to -10° (γHNO3 = 0.695)
  2. filtrationThe precipitated product is filtered off
  3. washwashed with a little 75% nitric acid
  4. customfreed from nitric acid adhering to it by evaporation under vacuum
  5. distillationfractionally distilled at 6 Torr and 267° head temperature

Sources & evidence

ORD record
ord-e91841ec957c498db539f8532535761b
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

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