Nitric Acid → 1-Nitroanthraquinone

HRID 1579647Notes

Reaction equation

HRID 1579647 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]>O>[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

4

Reactant 2

HCID 944Nitric AcidHCID 6780Anthraquinone

Product 1

HCID 67041-Nitroanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 208 g of anthraquinone and 2,550 g of 99% strength nitric acid (molar ratio 1:40) is stirred for 10 minutes at 20°C and then diluted with 302 ml of water to an acid content of approx. 88% by weight. 1,350 g of 98% strength nitric acid are then distilled off in vacuo, resulting, in the sump, in a molar ratio of approx. 18:1 and an acid content of 78%. The precipitate which has separated out is filtered off, washed until neutral and dried. The product is subjected to a fractional vacuum distillation at 10 mm Hg, and a head temperature of 281°C. 181 g of 99.2% pure 1-nitroanthraquinone (71% of theory) are obtained as the distillate.

Workup

  1. distillation1,350 g of 98% strength nitric acid are then distilled off in vacuo
  2. customresulting, in the sump, in a molar ratio of approx. 18:1
  3. customThe precipitate which has separated out
  4. filtrationis filtered off
  5. washwashed until neutral and
  6. customdried
  7. distillationThe product is subjected to a fractional vacuum distillation at 10 mm Hg
  8. customa head temperature of 281°C

Sources & evidence

ORD record
ord-35c3af5a41424bff90b4b4cb49147422
Source dataset
uspto-grants-1976_01
Patent number
US03931252

Reaction notes

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