Aniline → Phenazine

HRID 2299583Notes

Reaction equation

HRID 2299583 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>O>[CH:6]1[C:7]2[C:2](=[N:1][C:12]3[C:11]([N:8]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 7416Nitrobenzene

Product 1

HCID 4757Phenazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the dried material, 350 ml of deionized water was added, mixed vigorously and filtered through a Buchner funnel. The top layer was a shiny white layer of solid material. The bottom portion, primarily ZSM-5 appeared to be dull white in color. The top layer—about 8 gms, was treated further with addition of about 30.5 gms of 25% aqueous TMA(OH) and 300 ml of deionized water. The loading was done for four hours at about 45° C. The resulting slurry was filtered and then dried in a vacuum desiccator for twenty four hours at 42° C. The dried material showed two layers of solid. The material, although it was not hard and therefore easier to grind failed the coupling reaction test which consisted of reacting aniline and nitrobenzene in that it produced significant amounts of phenazine. It is estimated that the material used in the coupling reaction test had a TMA(OH) content of about 33 wt. %. It is apparent that TMA(OH) loading at such a high level causes the ZSM-5 crystal structure to collapse.

Workup

  1. additionmixed vigorously
  2. filtrationfiltered through a Buchner funnel
  3. additionThe top layer—about 8 gms, was treated further with addition of about 30.5 gms of 25% aqueous TMA(OH) and 300 ml of deionized water
  4. filtrationThe resulting slurry was filtered
  5. customdried in a vacuum desiccator for twenty four hours at 42° C
  6. customeasier to grind
  7. customthe coupling reaction test which

Sources & evidence

ORD record
ord-b55acb0dc6b242e7978d63254016e914
Source dataset
uspto-grants-2002_12
Patent number
US06495723B1

Reaction notes

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