Nitric Acid → 1-Nitroanthraquinone

HRID 1580194Notes

Reaction equation

HRID 1580194 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.F.[N+:18]([O-])([OH:20])=[O:19]>O>[N+:18]([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-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 6780AnthraquinoneHCID 14917Hydrofluoric Acid3×

Product 1

HCID 67041-Nitroanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

500 g of anthraquinone and 500 ml of 85 percent strength hydrogen fluoride are initially introduced into a 4 liter Venuleth vessel and stirred for 15 minutes. A mixture of 500 ml of hydrogen fluoride (85 percent strength) and 140 ml of nitric acid (98 percent strength) is added at room temperature over the course of 5 minutes. The bath temperature of the Venuleth vessel is then raised to 50°C and the mixture is stirred at this temperature for 8 hours. The hydrogen fluoride is largely stripped off in vacuo (approx. 50 mm Hg) at the same temperature. The residue is treated with water, filtered off, washed and dried. 610 g of nitro-anthraquinone of the following composition are obtained:

Workup

  1. additionis added at room temperature over the course of 5 minutes
  2. stirringthe mixture is stirred at this temperature for 8 hours
  3. filtrationfiltered off
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-63a2d0ced1c6471fb99df5284e30355d
Source dataset
uspto-grants-1976_01
Patent number
US03932473

Reaction notes

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