Nitric Acid → 1-Nitroanthraquinone

HRID 1579648Notes

Reaction equation

HRID 1579648 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-NitroanthraquinoneYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 208 g of anthraquinone and 1,210 g of 99% strength nitric acid (molar ratio 1:19) is stirred for 14 minutes at 35°C and subsequently adjusted to an acid content of 78% with 319 ml of water. The product which precipitates is filtered off, washed until neutral and dried. The product is subjected to a fractional distillation at 5 mm Hg, and a head temperature of 262°C. 99.4% pure 1-nitroanthraquinone is obtained as the distillate, in 69% yield (176 g).

Workup

  1. customThe product which precipitates
  2. filtrationis filtered off
  3. washwashed until neutral and
  4. customdried
  5. distillationThe product is subjected to a fractional distillation at 5 mm Hg
  6. customa head temperature of 262°C

Sources & evidence

ORD record
ord-ed72465ceb474e4297676c0cf1c0367f
Source dataset
uspto-grants-1976_01
Patent number
US03931252

Reaction notes

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