Oxidation of Picoline with Oxygen to Nicotinic Acid against Co2+, NHPI, and Phosphonium or Ammonium Bromides

Author:

Lisicki Dawid1ORCID,Talik Dorota1,Orlińska Beata1ORCID

Affiliation:

1. Department of Organic Chemical Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland

Abstract

Nicotinic acid (NA) is a heteroaromatic carboxylic acid mainly used as feed, in breakfast cereals, and as a beverage additive. Moreover, it is used as an anti-pellagra drug and as an ingredient in multivitamin supplements. It is manufactured using the Lonza process from 3-ethyl-3-methylpyridyne as a raw material using HNO3 as the oxidant agent. However, the use of such an oxidant is connected with greenhouse gases, thus making the technology non-ecological. Another industrial process is oxidative ammonolysis of 3-picoline followed by hydrolysis of a reaction intermediate to NA. This paper presents the results of research on the selective oxidation of 3-picoline with oxygen to NA. Bromide organic salts, including ionic liquids, N-hydroxyphtalimide, and cobalt(II) salts, were used as the catalysts. The reaction was carried out with acetic acid (AcOH) as a solvent. The bromide salts imidazolium bromide, quaternary ammonium bromide, and quaternary phosphonium bromide were used. They also fill the role of corrosion inhibitors caused by the acidic and highly oxidative reaction environment.

Funder

Silesian University of Technology

Publisher

MDPI AG

Subject

Physical and Theoretical Chemistry,Catalysis,General Environmental Science

Reference48 articles.

1. Lisicki, D., Nowak, K., and Orlińska, B. (2022). Methods to Produce Nicotinic Acid with Potential Industrial Applications. Materials, 15.

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3. Pfammatter, T., Schreuner, G., Stocker, A., and Mati, O. (1973). Process for the Production of Pyridine Carboxylic Acids From Lower Alykyl Pyrones. (3741976), U.S. Patent.

4. Chuck, R. (2009). Green Sustainable Chemistry in the Production of Nicotinates. Sustain. Ind. Chem., 541–550.

5. Musser, M.T. (2005). Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co., KGaA.

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