Nitric Acid → 4-Nitrotoluene

HRID 1486464Notes

Reaction equation

HRID 1486464 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[N+]([C:13]1[C:14]([N+]([O-])=O)=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=1)([O-])=O>C1(C)C=CC=CC=1>[N+:1]([C:18]1[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][CH:13]=1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 1118Sulfuric AcidHCID 117612,3-Dinitrotoluene

Product 1

HCID 74734-Nitrotoluene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

Aromatic nitro compounds like dinitrotoluene (DNT) or mononitrobenzene (MNB) are commercially produced through nitration of an aromatic with a mixture of nitric acid and sulfuric acid. The reaction is a biphasic reaction, typically the reaction rate is determined by the mass transfer between the two phases. In case of toluene nitration the reaction is typically carried out isothermally, toluene is present in molar substochiometry which means the molar ration of nitric acid to toluene is >1, typically 1.01-1.2. In a first step the toluene is nitrated to form mononitrotoluene (MNT). The biphasic reaction mixture undergoes phase separation into an aqueous phase containing the main part of sulfuric acid and an organic phase containing the main part of MNT. The organic phase then undergoes nitration to DNT in a further biphasic reaction. Again the reaction mixture undergoes phase separation into an aqueous phase and an organic phase containing DNT.

Workup

  1. customa biphasic reaction

Sources & evidence

ORD record
ord-a9ea3c3d9bb84f07961fd69a08f1bb24
Source dataset
uspto-grants-2016_08
Patent number
US09428441B2

Reaction notes

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