Ammonia → 3-Cyanopyridine

HRID 746263Notes

Reaction equation

HRID 746263 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1.N.C[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C[C:24]1C=CC=C[N:25]=1>>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH3:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=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 80% PV3MO12Ox.20% SiO2 catalyst of Example 1 was placed in the microreactor and equilibrated at 405° C., then a gaseous mixture of 0.82 3-methylpyridine:0.18 3-methylpiperidine:7.5 NH3 :19.9 air 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 93 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-7289a97e319c4625b3a0466d2c88ecf1
Source dataset
uspto-grants-1986_07
Patent number
US04603207

Reaction notes

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