Acetic Acid → Nicotinic Acid

HRID 1940889Notes

Reaction equation

HRID 1940889 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=CC=1.[C:8]([OH:11])(=[O:10])[CH3:9]>[Br-].C([N+](CCC)(CCC)CCC)CC.C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.O>[C:8]([OH:11])(=[O:10])[C:9]1[CH:1]=[CH:2][CH:3]=[N:4][CH:5]=1

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 79703-Methylpyridine

Product 1

HCID 938Nicotinic Acid

Reagents, catalysts & solvents 4

HCID 6277Cobalt diacetateCatalystHCID 12525Manganous AcetateCatalystHCID 74745Tetrapropylammonium bromideCatalystHCID 962WaterSolvent

Procedure

The same autoclave as that used in Example 1 was charged with 25 parts by weight of 3-methylpyridine, 0.38 part by weight of cobalt acetate, 0.27 part by weight of manganese acetate, 1 part by weight of tetrapropylammonium bromide and 150 parts by weight of acetic acid having a 5 wt % water content, and the mixture was allowed to react in the same manner as in Example 1 to give 21.7 parts by weight of a crude nicotinic acid crystal. The conversion of the 3-methylpyridine was 93.7 mol %, the selectivity to the nicotinic acid was 99.0 mol %, and the yield of the nicotinic acid 92.8 mol %. The conversion and the yield in Example 2 were improved over those in Example 1 since the solvent was used in a larger amount in Example 2. The crude nicotinic acid had a bromine concentration of 608 ppm and showed a dissolved b value of 5.44.

Workup

  1. customto react in the same manner as in Example 1

Sources & evidence

ORD record
ord-564dcfae0a3f459a83c031a0c2306f9a
Source dataset
uspto-grants-1997_12
Patent number
US05700944

Reaction notes

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