Nitric Acid → Ammonia

HRID 1707106Notes

Reaction equation

HRID 1707106 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[NH:7][CH:8]=[CH:9][N:10]=1>S(=O)(=O)(O)O>[CH3:5][C:6]1[NH:7][C:8]([N+:1]([O-:4])=[O:2])=[CH:9][N:10]=1.[NH3:1]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 127492-Methylimidazole

Product 2

HCID 222AmmoniaHCID 127602-Methyl-5-nitroimidazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In a boiler of acid-resistant stainless steel of 800 liters capacity, provided with a stirring device, a cooling jacket and an efficient reflux condenser, 150 liters of nitric acid of 1.50 density preheated to about 85° was placed and stirred in order to maintain a constant temperature and a nitrated solution obtained as in example I was poured in dropwise and then 80 kg of 2-methylimidazole in 80 liters of concentrated sulphuric acid was added. The reacting solution was stirred until a clear diminishing of the exothermic effect was noted and the temperature was raised gradually, after 1 hour, to 110° and this temperature was maintained for 25 minutes. The reflux condenser was thereafter removed and the temperature increased to about 140° and was maintained at this level for 30-minutes, the volatile components being distilled off during that time and removed from the reacting medium. The reacted solution was cooled and divided, and 1/3 was left in the nitrator, and from the remaining 2/3 of this solution 2-methyl-5-nitroimidazole was isolated in known manner (by diluting with water and neutralizing with ammonia to pH about 6). 88 kg of product were obtained corresponding to about 77% of theoretical.

Workup

  1. customdensity preheated to about 85°
  2. temperatureto maintain a constant temperature
  3. customa nitrated solution obtained as in example I
  4. additionwas added
  5. stirringThe reacting solution was stirred until
  6. temperaturethe temperature was raised gradually, after 1 hour, to 110°
  7. temperaturethis temperature was maintained for 25 minutes
  8. customThe reflux condenser was thereafter removed
  9. temperaturethe temperature increased to about 140°
  10. temperaturewas maintained at this level for 30-minutes
  11. distillationthe volatile components being distilled off during that time
  12. customremoved from the reacting medium
  13. temperatureThe reacted solution was cooled
  14. wait1/3 was left in the nitrator

Sources & evidence

ORD record
ord-586b4dd9158d48dcb28dd4da05cde748
Source dataset
uspto-grants-1980_06
Patent number
US04209631

Reaction notes

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