Nitric Acid → 1-Nitroanthraquinone

HRID 437412Notes

Reaction equation

HRID 437412 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 98.9%

Procedure

A mixture of 2.08 kg of anthraquinone and 9.545 kg of 99% nitric acid per hour (mole ratio 15:1) is cooled to 0° and continuously reacted in a flow tube reactor with a residence time of 13 minutes and a final temperature of 55°. The solution leaving the reactor is continuously cooled to -10° to stop the reaction and introduced into a crystallising apparatus together with 19.33 kg per hour of 66.2% nitric acid (crystallisation acid 76%, γHNO3 = 0.469). The precipitated product is continuously suction-filtered, washed with a little 76% nitric acid, freed from nitric acid adhering to it and subjected to continuous vacuum rectification (10 Torr, head temperature 281°). 1.740 kg of 98.9% pure 1-nitroanthraquinone are obtained per hour (68% of the theoretical amount).

Workup

  1. temperatureis cooled to 0°
  2. customcontinuously reacted in a flow tube reactor with a residence time of 13 minutes
  3. customtemperature of 55°
  4. customThe solution leaving the reactor
  5. temperatureis continuously cooled to -10°
  6. customthe reaction
  7. filtrationThe precipitated product is continuously suction-filtered
  8. washwashed with a little 76% nitric acid
  9. customsubjected to continuous vacuum rectification (10 Torr, head temperature 281°)

Sources & evidence

ORD record
ord-4dd895d119e74854a985c14c3664319b
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

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