Nitric Acid → 1-Nitroanthraquinone

HRID 437414Notes

Reaction equation

HRID 437414 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 98.9%

Procedure

208 g of anthraquinone are introduced into 1145 g of 99% nitric acid (mole ratio 18:1) at 25° with cooling and the reaction mixture is stirred for 25 minutes. The reaction is then stopped by rapidly distilling off 693 g of 99% nitric acid and the product is precipitated by slowly cooling the reaction mixture to 0°. After washing with dilute nitric acid, the product is freed from nitric acid and distilled together with 800 g of paraffin oil at 30 Torr with a head temperature of between 250° and 300°. 1-Nitroanthraquinone which precipitates from the condensate is filtered off and freed from paraffin oil by washing with petroleum ether. 163 g of 98.9% pure 1-nitroanthraquinone are obtained (63.5% of the theoretical amount).

Workup

  1. temperaturewith cooling
  2. distillationby rapidly distilling off 693 g of 99% nitric acid
  3. customthe product is precipitated
  4. temperatureby slowly cooling the reaction mixture to 0°
  5. washAfter washing with dilute nitric acid
  6. distillationdistilled together with 800 g of paraffin oil at 30 Torr with a head temperature of between 250° and 300°
  7. custom1-Nitroanthraquinone which precipitates from the condensate
  8. filtrationis filtered off
  9. washby washing with petroleum ether

Sources & evidence

ORD record
ord-a470d809745c4be5a646465e261affc1
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

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