Reaction #464312

ord-34fda49260ef4dc8b699a3a8d6e29489

Reaction equation

O=[N+]([O-])O
nitric acid
Nc1ccc(N)cc1
1,4-phenylenediamine
NC(N)=S
thiourea
O=[N+]([O-])O
nitric acid
O=[N+]([O-])O
Nitric acid
O=[N+]([O-])O
nitric acid
NC(N)=S
thiourea
→
O=[N+]([O-])[O-].[NH3+]O
hydroxylammonium nitrate
O=[N+]([O-])O
nitric acid
O=[N+]([O-])[O-].[NH4+]
ammonium nitrate

Reactants

O=[N+]([O-])O
nitric acid
Nc1ccc(N)cc1
1,4-phenylenediamine
NC(N)=S
thiourea
O=[N+]([O-])O
nitric acid
O=[N+]([O-])O
Nitric acid
O=[N+]([O-])O
nitric acid
NC(N)=S
thiourea

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONis also added into the catholyte compartment
  2. 2
    TemperatureWhile maintaining the temperature between 5° C. and 10° C.

Procedure

The general procedure of Example 8 is repeated except that thiourea is also added into the catholyte compartment. A solution of 1 M nitric acid, 50 mM 1,4-phenylenediamine and 250 mM of thiourea is charged to the catholyte compartment. A solution of 4 M nitric acid is charged to the anolyte compartment. Nitric acid is added to the catholyte compartment to maintain the nitric acid concentration between 0.5 M and 1 M under application of an electrical current. While maintaining the temperature between 5° C. and 10° C., a current of 45 amps (3 ASI) and a cell voltage of about 6.5 volts is applied. The catholyte is stirred under application of the current. A solution of 1.77 M hydroxylammonium nitrate and 0.5 M nitric acid with no detectable ammonium nitrate is obtained from the catholyte compartment. An overall current efficiency of 90% for formation of hydroxylammonium nitrate is achieved.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06024855uspto-grants-2000_02