Picric Acid → 2,4,6-Trinitroaniline

HRID 1828392Notes

Reaction equation

HRID 1828392 reaction equation
[C:1]1([C:15](O)=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=[C:6]([N+:7]([O-:9])=[O:8])[CH:5]=1)[N+:2]([O-:4])=[O:3].P([O-])([O-])(O)=O.[NH4+:22].[NH4+].S1(CCCC1)(=O)=O>O>[CH:5]1[C:1]([N+:2]([O-:4])=[O:3])=[C:15]([NH2:22])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]=1[N+:7]([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 6954Picric AcidHCID 24540Diammonium hydrogen phosphateHCID 31347Sulfolane

Product 1

HCID 102712,4,6-TrinitroanilineYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Picric acid (10.0 g, 43.8 mmol), diammonium hydrogen phosphate (11.6 g, 87.6 mmol) and dry sulfolane (40 ml) are placed in a glass-lined, stainless steel reactor to form a 1.1M concentration reaction slurry. The reactor is sealed and the reaction slurry is stirred with heating for 2 hr as the temperature increases from 25 to 175° C. (20 psi pressure). The temperature is maintained at 175° C. and stirring is continued for an additional 20 hr. The cooled reaction mixture is mixed with water (400 ml) and the insoluble material is collected, washed with water and dried to produce picramide in 93% yield (Table 2, entry 5).

Workup

  1. customto form
  2. concentrationa 1.1M concentration reaction slurry
  3. customThe reactor is sealed
  4. temperaturewith heating for 2 hr as the temperature
  5. temperatureThe temperature is maintained at 175° C.
  6. stirringstirring
  7. customThe cooled reaction mixture
  8. customthe insoluble material is collected
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-effe549dd00b4d0e9d78513e05fad0c6
Source dataset
uspto-grants-2006_06
Patent number
US07057072B2

Reaction notes

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