Acetic Acid → 2-Acetylpyridine

HRID 1831849Notes

Reaction equation

HRID 1831849 reaction equation
[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O.[C:15](O)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:15]([C:3]1[CH:2]=[CH:7][CH:6]=[CH:5][N:4]=1)(=[O:17])[CH3:16].[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 813533-Pyridinecarboxylic acid, butyl ester

Product 2

HCID 142862-AcetylpyridineHCID 813533-Pyridinecarboxylic acid, butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An electrically heated tubular reactor with an i. d. of 12 mm was filled with 15 ml (≈15 g) of catalyst prepared according to EP-A-0 352 674, example 1. Over a period of 63 h, a mixture of butyl nicotinate (104 g), water (162 g) and acetic acid (606 g) was metered using a precision pump to the reactor operating at 405° C. From the reaction mixture, 30 g of acetyl pyridine, 3 g of pyridine and 26 g of butyl nicotinate were obtained. This corresponded to a yield of 43% 3-acetylpyridine at a butyl nicotinate conversion of 75% (selectivity 58%). The selectivity of pyridine formation was 5%.

Workup

  1. customprepared
  2. customoperating at 405° C

Sources & evidence

ORD record
ord-59986baf05124609b6e28875a8530e32
Source dataset
uspto-grants-2006_06
Patent number
US07067673B2

Reaction notes

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