Nitric Acid → 2,3-Dinitrotoluene

HRID 259089

Reaction equation

HRID 259089 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](C)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:11]([O-:14])(O)=[O:12].S(=O)(=O)(O)O.[CH2:20](Cl)Cl>>[N+:11]([C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH3:20])[CH:6]=[CH:7][CH:8]=1)([O-:14])=[O:12]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 74734-Nitrotoluene

Product 1

HCID 117612,3-DinitrotolueneYield 99%

Procedure

68.6 g (0.5 mol) of 4-nitrotoluene were dissolved in 80 ml of methylene chloride and 38.6 g (0.6 mol) of 98% by weight nitric acid, followed by the addition with stirring over a period of 1 hour at reflux temperature of 40 g of 100% by weight sulphuric acid. After stirring under reflux for another 2 hours, the methylene chloride phase was separated off without cooling and washed three times while still hot with 3 × 200 ml of water. After the washing water had been carefully separated off, the methylene chloride was distilled off, leaving 90.2 g of dinitrotoluene containing 99% of 2,4-dinitrotoluene (98% of the theoretical yield).

Workup

  1. stirringAfter stirring
  2. temperatureunder reflux for another 2 hours
  3. customthe methylene chloride phase was separated off
  4. temperaturewithout cooling
  5. washwashed three times while still hot with 3 × 200 ml of water
  6. customAfter the washing water had been carefully separated off
  7. distillationthe methylene chloride was distilled off

Sources & evidence

ORD record
ord-e8d7992ac05249c99e6fad8e1e9065b7
Source dataset
uspto-grants-1977_07
Patent number
US04036838

Linked notes

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