Aniline → N-Phenyl-p-phenylenediamine

HRID 2163277Notes

Reaction equation

HRID 2163277 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(#[N:16])C>F[B-](F)(F)F.C([N+](CCC)(CCC)CCC)CC>[CH:5]1[CH:6]=[CH:7][C:2]([NH:1][C:10]2[CH:9]=[CH:8][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6115Aniline2×HCID 6342AcetonitrileHCID 8058Hexane

Product 1

HCID 7564N-Phenyl-p-phenylenediamine

Reagents, catalysts & solvents 1

HCID 9558Ammonium, tetrapropyl-, tetrafluoroborate(1-)Catalyst

Procedure

The apparatus described in EXAMPLE 1 above was employed. Two liters of solution containing 20.0 grams (0.215 mole) of aniline, 54.4 grams (0.2 mole) of tetra-n-propylammonium tetra-fluoroborate in acetonitrile was charged to the reservoir. A similar solution (50 milliliters) but without the aniline was charged to each of first and second secondary electrode compartments (3b and 4b). The flow rate of the solution from the reservoir, as determined by the flow meter, was 30 milliliters per minute; the first face (2a) of working electrode 2 current was 180 milliamperes at +1.2 volts versus the saturated calomel electrode (with occasional cathodic pulses to restore electrode activity); and the second and opposite face (2b) of working electrode 2 current was 20 milliamperes at -0.5 volt versus the saturated calomel electrode. The electrolysis was conducted over a period of 1.11 hours. The resulting sequentially electrolyzed electrolysis medium was collected and the solvent evaporated in vacuo to yield a residue which was agitated with hexane to remove unreacted aniline. The small quantity of oil remaining after the extraction by hexane was shown to be 4-aminodiphenylamine via gas chromatographic analysis and comparison with an authentic sample.

Workup

  1. additionwas charged to the reservoir
  2. customThe resulting sequentially electrolyzed electrolysis medium was collected
  3. customthe solvent evaporated in vacuo
  4. customto yield a residue which
  5. customto remove unreacted aniline
  6. extractionafter the extraction by hexane

Sources & evidence

ORD record
ord-18c698b4d7944e5aa17def8bbc3649ad
Source dataset
uspto-grants-1979_01
Patent number
US04133726

Reaction notes

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