Nitric Acid → 1-Nitroanthraquinone

HRID 437415Notes

Reaction equation

HRID 437415 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.O.[N+:18]([O-])([OH:20])=[O:19]>>[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

4

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 6780Anthraquinone

Product 1

HCID 67041-NitroanthraquinoneYield 99.2%

Procedure

208 g of anthraquinone in 969 g of 97.5% nitric acid (mole ratio 15:1) are heated to 35° for 2 hours with stirring. The reaction is stopped by the addition of 103 ml of water. After removal of 265 g of 99% nitric acid by distillation (crystallisation acid 81%, γHNO3 = 0.520), the precipitated product is freed from nitric acid and dried and distilled at 30 Torr with head temperatures of 250° to 300°, together with about 800 g of silicone oil. The yield of 99.2% 1-nitroanthraquinone is 153 g (60% of the theoretical amount).

Workup

  1. customAfter removal of 265 g of 99% nitric acid
  2. distillationby distillation (crystallisation acid 81%, γHNO3 = 0.520)
  3. customdried
  4. distillationdistilled at 30 Torr with head temperatures of 250° to 300°, together with about 800 g of silicone oil

Sources & evidence

ORD record
ord-1397d422cae5446891db352e0f2953d8
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

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