Ammonia → 3-Cyanopyridine

HRID 2352343Notes

Reaction equation

HRID 2352343 reaction equation
N.[CH3:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:9][CH:10]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]1.C[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C[C:24]1C=CC=C[N:25]=1>>[CH3:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[CH3:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[C:24]([C:21]1[CH:22]=[N:17][CH:18]=[CH:19][CH:20]=1)#[N:25]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 79703-MethylpyridineHCID 79752-MethylpyridineHCID 12291N-MethylpiperidineHCID 790813-Methylpiperidine

Product 3

HCID 793-CyanopyridineHCID 79703-MethylpyridineHCID 790813-Methylpiperidine

Procedure

2.0 cc of the 80% PV3MO12Ox.20% SiO2 catalyst of Example 2 was placed in the microreactor and equilibrated at 405° C., then a gaseous mixture containing 7.5 moles of NH3 and 19.9 moles of air for each mole of the mixed heterocyclic containing 0.82 mole of 3-methylpyridine and 0.18 mole of 3-methylpiperidine was fed through the reactor using a contact time of 6.4 seconds. Conversion of the methylpiperidine was 100 percent and conversion of the methylpyridine was 92 percent. For each mole of combined 3-methylpiperidine plus 3-methylpyridine fed was obtained 0.853 mole of 3-cyanopyridine. If it be assumed that all of the converted 3-methylpyridine formed 3-cyanopyridine, the minimum selectivity of 3-methylpiperidine to 3-cyanopyridine was 50 percent.

Workup

  1. customequilibrated at 405° C.
  2. customa contact time of 6.4 seconds

Sources & evidence

ORD record
ord-405fd59081894f29a7ea7a169b00c34a
Source dataset
uspto-grants-1989_10
Patent number
US04876348

Reaction notes

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