Nitric Acid → 1-Nitroanthraquinone

HRID 437413Notes

Reaction equation

HRID 437413 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 98.2%

Procedure

208 g of anthraquinone are introduced into 764 g of 99% nitric acid (mole ratio 12:1) at room temperature with stirring. The reaction is then left to proceed adiabatically until the temperature reaches 45°. The reaction is then continued isothermally at 45° until the total reaction time is 17 minutes. The reaction is stopped by distilling off 330 g of 99% nitric acid. 128.0 g of 50% nitric acid (crystallisation acid 83.4%, γHNO3 = 0.542) are slowly added to the sump product (acid concentration approximately 94.4%, γHNO3 = 0.725). The product which precipitates under these conditions is suction-filtered, washed with a little dilute nitric acid, freed from nitric acid by washing with water, dried and subjected to vacuum rectification at 8 Torr with a head temperature of 275°. 162.3 g of 98.2% pure 1-nitroanthraquinone are obtained as a distillate (63% of the theoretical amount).

Workup

  1. waitThe reaction is then left
  2. customreaches 45°
  3. customis then continued isothermally at 45° until the total reaction time
  4. distillationby distilling off 330 g of 99% nitric acid
  5. addition128.0 g of 50% nitric acid (crystallisation acid 83.4%, γHNO3 = 0.542) are slowly added to the sump product (acid concentration approximately 94.4%, γHNO3 = 0.725)
  6. customThe product which precipitates under these conditions
  7. filtrationis suction-filtered
  8. washwashed with a little dilute nitric acid
  9. washby washing with water
  10. customdried
  11. customsubjected to vacuum rectification at 8 Torr with a head temperature of 275°

Sources & evidence

ORD record
ord-b24c4bc18ad542ac865a23538af4ae57
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

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