Oxidative ammonolysis of 3,4-dimethylpyridine on the vanadium oxide catalysts

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Pavel Vorobyev
Anna Serebryanskaya
Olga Yugay
Tatyana Mikhailovskaya

Abstract

Oxidative ammonolysis of 3,4-dimethylpyridine on an individual vanadium oxide (V2O5) catalyst and binary vanadium oxide catalysts, modified by additions of SnO2 and ZrO2, has been studied. A connection between СН-acidity of the methyl groups of the substrate in the gaseous phase and in the chemosorbed state and the sequence of their transformation into a cyano group has been established. It has been shown that nucleophilicity of vanadyl oxygen, calculated by the Density Functional Theory method, increases with V2O5 modification by SnO2 and ZrO2 additions. Herewith, an increasing yield of 3-methyl-4-cyanopyridine and imide of pyridine-3,4-dicarboxylic acid was observed. A proposed mechanism of the imide of pyridine-3,4-dicarboxylic acid formation has been discussed

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How to Cite
[1]
P. Vorobyev, A. Serebryanskaya, O. Yugay, and T. Mikhailovskaya, “Oxidative ammonolysis of 3,4-dimethylpyridine on the vanadium oxide catalysts”, J. Serb. Chem. Soc., vol. 85, no. 4, pp. 427–437, Apr. 2020.
Section
Organic Chemistry
Author Biographies

Pavel Vorobyev, A. B. Bekturov Institute of Chemical Sciences JSC, Almaty 050010

Laboratory of Oil Chemistry and petrochemical Synthesis

Doctor of Chemical Sciences

Principal Scientist

Anna Serebryanskaya, A. B. Bekturov Institute of Chemical Sciences JSC, Almaty 050010

Laboratory of Oil Chemistry and petrochemical Synthesis

Candidate of Chemical Sciences

Scientist

Olga Yugay, A. B. Bekturov Institute of Chemical Sciences JSC, Almaty 050010

Laboratory of Oil Chemistry and petrochemical Synthesis

Candidate of Chemical Sciences

Senior Scientist

Tatyana Mikhailovskaya, A. B. Bekturov Institute of Chemical Sciences JSC, Almaty 050010

Laboratory of Oil Chemistry and petrochemical Synthesis

Candidate of Chemical Sciences

Senior Scientist

References

Т. Delaine, V. Bernandes-Genisson, A. Quemard, P. Constant, B. Meunier, J. Bernadou, Eur. J. Med. Chem. 45 (2010) 4554 (https://doi.org/10.1016/j.ejmech.2010.07.016)

T. R. K. Reddy, R. Mutter, W. Heal, K. Guo, V.J. Gillet, S. Pratt, B. Chen, J. Med. Chem. 49 (2006) 607 (https://doi.org/10.1021/jm050610f)

E. E. Ergozhin, B. A. Mukhitdinova, V. V. Shaligina, B. Zh. Shekeeva, K. M. Sartbaeva, React. Funct. Polym. 65 (2005) 93 (https://doi.org/10.1016/j.reactfunctpolym.2004.12.003)

B. V. Suvorov, Oxidative Ammonolysis of Organic Compounds, Nauka, Alma-Ata, 1971, p. 210

R. Chuck, Appl. Catal., A 280 (2005) 75 (https://doi.org/10.1016/j.apcata.2004.08.029)

P. B. Vorobev, D. Kh. Sembaev, Russ. J. Gen. Chem. 75 (2005) 147 (https://doi.org/10.1007/s11176-005-0186-1)

D. Kh. Sembaev, O. K. Yugay, S. G. Klepikova, Eurasian Chem.-Tech. J. 6 (2004) 127 (https://doi.org/10.18321/ectj601)

J. Okada, S. Morita, Y. Miwa, T. Tashima, Yakugaku Zasshi 98 (1978) 1391

J. Okada, S. Morita, Y. Miwa, Chem. Pharm. Bull. 22 (1974) 2402 (https://doi.org/10.1248/cpb.22.2402)

P. Vorobyev, T. Mikhailovskaya, O. Yugay, A. Serebryanskaya, N. Chukhno, R. Kurmakizy, J. Serb.Chem.Soc. 82 (2017) 791 (http://doi.org/10.2298/JSC161220023Z)

W. Koсh, M. C. Holthausen, Chemists Guide to Density Functional Theory. 2nd ed., Wiley-VCH, Weinheim, 2001, p. 293

J. B. Foresman, A. Frish, Exploring Chemistry with Electronic Structures Methods, 2nd ed., Gaussian Inc., Pittsburgh, PA, 1996, p. 335

Gaussian09, Revision D.01., Gaussian Inc., Wallingford, CT, 2009

D. J. Cram, Fundamentals of Carbanion Chemistry, Academic Press, New York, 1965, p. 290

K. Higasi, H. Baba, A. Rembaum, Quantum organic chemistry. Interscience Publishers, Division of John Wiley & Sons, Inc., New York, 1965, p. 380

L. Ya. Margolis, V. N. Korchak, Russ. Chem. Rev. 67 (1998) 1073 (https://doi.org/10.1070/RC1998v067n12ABEH000428)

N. I. Chukhno, I. S. Kolodina, D. Kh. Sembaev, Izv. Akad. Nauk KazSSR. Ser.Chim. 4 (1989) 31.

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