Nitric Acid → 1-Nitroanthraquinone

HRID 1077057Notes

Reaction equation

HRID 1077057 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-Nitroanthraquinone

Procedure

208 g of anthraquinone are stirred with 1,210 g of 99% strength nitric acid (molar ratio of nitric acid/anthraquinone = 19:1) for 26 minutes at 25°, resulting in a molar fraction of 0.87. To terminate the reaction, 566 g of 99% strength nitric acid are distilled off rapidly so that subsequently the molar fraction in the sump is 0.79. On adding 112 g of water, the temperature of the sump rises and on slow cooling the desired product separates out. (Molar fraction γHNO3 = 0.52). After centrifuging off at room temperature, rinsing with 75% strength nitric acid, washing until neutral and drying, 204 g of 89.4% strength 1-nitroanthraquinone are obtained (72% of theory).

Workup

  1. customresulting in a molar fraction of 0.87
  2. customTo terminate
  3. customthe reaction, 566 g of 99% strength nitric acid
  4. distillationare distilled off rapidly so that subsequently the molar fraction in the sump
  5. additionOn adding 112 g of water
  6. temperaturethe temperature of the sump rises and on slow cooling the desired product
  7. customAfter centrifuging off at room temperature
  8. washrinsing with 75% strength nitric acid
  9. washwashing until neutral and
  10. customdrying

Sources & evidence

ORD record
ord-8f409386b1cb4dd6b0484df9cd7da03b
Source dataset
uspto-grants-1976_05
Patent number
US03959317

Reaction notes

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