Reaction #464313

ord-e0673ea4cd8f4e5b9a00dafe4d6d7caa

Reaction equation

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

Reactants

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

Reagents

CCCC[N+](CCCC)(CCCC)CCCC.[Cl-]
tetrabutylammonium chloride
CCCC[N+](CCCC)(CCCC)CCCC.[Cl-]
tetrabutylammonium chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONis 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 tetrabutylammonium chloride is added into the catholyte compartment. A solution of 1 M nitric acid, 50 mM 1,4-phenylenediamine and 0.1 M tetrabutylammonium chloride 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 1.65 M hydroxylammonium nitrate and 0.7 M nitric acid with no detectable ammonium nitrate is obtained from the catholyte compartment. An overall current efficiency of 85% for formation of hydroxylammonium nitrate is achieved.

Source

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