Nitric Acid → 5-Nitronaphthalene-1,4-dione

HRID 267252Notes

Reaction equation

HRID 267252 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19].S(=O)(=O)=O>O>[N+:18]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[C:4](=[O:11])[CH:3]=[CH:2][C:1]2=[O:12])([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 85301,4-NaphthoquinoneHCID 24682Sulfur trioxide

Product 1

HCID 123364025-Nitronaphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

In the same apparatus as in Example 1, 20 g of 1,4-naphthoquinone was stirred into 70 g of a mixed acid consisting of 70 percent by weight of sulfuric acid, 20 percent by weight of nitric acid and 10 percent by weight of sulfur trioxide, with cooling at 0° to 5°C. The reaction mixture was heated to 15°C over 30 minutes and then maintained at the temperature for 3 hours. The liquid reaction mixture was then stirred in 2 minutes into 400 ml of water at 20°C to precipitate crystals. During the precipitation, the liquid temperature reached the highest value of 68°C. The crystals were well dispersed during stirring. After completion of addition of the reaction mixture, the liquid temperature was quickly lowered by cooling to 35°C. The so precipitated crystals were separated, washed with water and dried in the same manner as in Example 5 to obtain 22.5 g of crude 5-nitro-1,4-naphthoquinone of a melting point of 153°C. The amount of acidic matter remaining in the crystals was 0.3 percent by weight in terms of sulfuric acid.

Workup

  1. temperaturewith cooling at 0° to 5°C
  2. temperaturemaintained at the temperature for 3 hours
  3. customThe liquid reaction mixture
  4. customto precipitate crystals
  5. customDuring the precipitation
  6. customthe highest value of 68°C
  7. additionThe crystals were well dispersed
  8. additionAfter completion of addition of the reaction mixture
  9. temperatureby cooling to 35°C
  10. customThe so precipitated crystals
  11. customwere separated
  12. washwashed with water
  13. customdried in the same manner as in Example 5

Sources & evidence

ORD record
ord-13dc44067afe4aae89134fe0bf0d82ea
Source dataset
uspto-grants-1976_03
Patent number
US03941815

Reaction notes

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