Oxygen → 2,4-Dinitrotoluene

HRID 1596852Notes

Reaction equation

HRID 1596852 reaction equation
[N+]([O-])=O.O=O.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])([O-:8])=[O:7].[N+:16](C1C=CC(C)=CC=1)([O-:18])=[O:17]>C1(C)C=CC=CC=1>[N+:6]([C:9]1[CH:14]=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:11][C:10]=1[CH3:15])([O-:8])=[O:7].[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[C:10]=1[CH3:15])([O-:8])=[O:7]

Participants

7

Reactant 4

HCID 977OxygenHCID 69442-NitrotolueneHCID 74734-NitrotolueneHCID 178526396Nitrogen Dioxide

Product 2

HCID 84612,4-DinitrotolueneHCID 118132,6-Dinitrotoluene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

After supplying 0.2 mol of toluene and 0.002 mol of ferric chloride to an autoclave, 0.9 mol of liquid nitrogen dioxide was added to the autoclave. Next, oxygen was injected at a pressure of 120 psi. At first the reactants were reacted at room temperature. After 30 minutes, the autoclave was heated to 60° C. and then the reactants were reacted for 3 hours. After the initial 30 minutes, all of toluene was converted into o-nitrotoluene and p-nitrotoluene at a ratio of 55:45, respectively. After 3 hours, 2,4-dinitro-toluene and 2,6-dinitrotoluene (83:17) were formed at a yield of more than 98% analyzed by gas chromatography.

Workup

  1. additionwas added to the autoclave
  2. customAt first the reactants were reacted at room temperature
  3. customthe reactants were reacted for 3 hours
  4. custom30 minutes
  5. waitAfter 3 hours

Sources & evidence

ORD record
ord-ac58a858b5d24f018d9084ea4e4102e5
Source dataset
uspto-grants-2001_09
Patent number
US06291726B1

Reaction notes

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