Nitric Acid → 1-Nitroanthraquinone

HRID 437407Notes

Reaction equation

HRID 437407 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]>>[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

3

Reactant 2

HCID 944Nitric Acid2×HCID 6780Anthraquinone

Product 1

HCID 67041-NitroanthraquinoneYield 98.5%

Conditions

Temperature
0 °C

Procedure

208 g of anthraquinone and 509 g of 99% nitric acid (more ratio 8:1) are heated to 60° C for 1 hour with stirring. The reaction mixture is then rapidly cooled to 0° C, and 1584 g of 73% nitric acid are added (crystallisation acid 78%, γHNO3 = 0.493). The crystallised product is filtered off, washed with a little 76% nitric acid, freed from nitric acid under vacuum and fractionally distilled at 15 Torr and a head temperature of 292°. 157 g of 98.5% 1-nitroanthraquinone are obtained (61.2% of theoretical amount).

Workup

  1. custom(crystallisation acid 78%, γHNO3 = 0.493)
  2. filtrationThe crystallised product is filtered off
  3. washwashed with a little 76% nitric acid
  4. distillationfractionally distilled at 15 Torr
  5. customa head temperature of 292°

Sources & evidence

ORD record
ord-b7bf63725a1849518f42592372fdad85
Source dataset
uspto-grants-1977_06
Patent number
US04031116

Reaction notes

Loading…