Nitric Acid → 1-Nitroanthraquinone

HRID 1579649Notes

Reaction equation

HRID 1579649 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
45 °C

Procedure

A mixture of 208 g of anthraquinone and 763 g of 99% strength nitric acid (molar ratio 1:12) is stirred at 45°C for 18 minutes and then diluted to an acid content of approx. 90% with 51 ml of water. 193 G of 98% strength nitric acid are then distilled off in vacuo, resulting in an acid content of approx. 87%, and a molar ratio of approx. 8:1, in the sump. The product which precipitates is filtered off, washed until neutral and dried. Fractional distillation of the product at 6 mm Hg and a head temperature of 267°C gives 165 g of a 99.4% pure 1-nitroanthraquinone (65% of theory).

Workup

  1. distillation193 G of 98% strength nitric acid are then distilled off in vacuo
  2. customresulting in an acid content of approx. 87%
  3. customThe product which precipitates
  4. filtrationis filtered off
  5. washwashed until neutral and
  6. customdried
  7. distillationFractional distillation of the product at 6 mm Hg

Sources & evidence

ORD record
ord-86321b8b474840dbafbd91ce87159f70
Source dataset
uspto-grants-1976_01
Patent number
US03931252

Reaction notes

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