Skip to main content
SpringerLink
Log in

Microporous and Micro-meso-macroporous Y Zeolites in the Synthesis of 2-Methyl-5-ethylpyridine

  • Published:
Petroleum Chemistry Aims and scope Submit manuscript

Abstract

The study investigates the catalytic properties of microporous (H–Y) and micro-meso-macroporous (H–Y-mmm) FAU-type zeolites in the synthesis of 2-methyl-5-ethylpyridine (MEP) by the reaction of acetaldehyde with ammonia. At 150°C, an acetaldehyde to ammonia molar ratio of 1 : 3, and a catalyst content of 10 wt %, a MEP yield of 58% (0.95H–Y) and 63% (0.95H–Y-mmm) was achieved with a MEP selectivity of 91 and 93%, respectively. The examination of the catalyst stability revealed that hierarchical H–Y-mmm zeolites ensure a 100% MEP selectivity during 4–5 cycles with a slight decline in the catalytic activity, while H–Y zeolites are active during the first cycle only.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1.
Fig. 1.
Fig. 2.

Similar content being viewed by others

REFERENCES

  1. Scriven, E.F.V, Toomey, Jr.J.E., and Murugan, R., Pyridine and Pyridine Derivatives. Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley & Sons, 2005, vol. 20, p. 53. https://doi.org/10.1002/0471238961.1625180919031809.a01

  2. Henry, G.D., Tetrahedron, 2004, no. 60, p. 6043. https://doi.org/10.1016/j.tet.2004.04.043

    Article  CAS  Google Scholar 

  3. Wang, H., Wang, J., Guo, H., Chen, X., Yu, X., Ma, Y., Ji, P., Naito, K., Zhang, Z., and Zhang, Q., Polym. Chem., 2018, no. 9, p. 976. https://doi.org/10.1039/C7PY01990D

    Article  CAS  Google Scholar 

  4. Yuan, N., Liang, Y., Erichsen, E.S., and Anwander, R., RSC Adv., 2015, no. 5, p. 67077. https://doi.org/10.1039/C5RA11612K

    Article  CAS  Google Scholar 

  5. Burkhardt, E.R. and Coleridge, B.M., Tetrahedron Lett., 2008, no. 49, p. 5152. https://doi.org/10.1016/j.tetlet.2008.06.095

    Article  CAS  Google Scholar 

  6. Schimizu, S., Watanabe, N., Kataoka, T., Shoji, T., Abe, N., Morishita, S., and Ichimura I., Pyridine and Pyridine Derivatives. Ullmann’s Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2012, p. 557. https://doi.org/10.1002/14356007.a22_399

  7. Farberov, M.I., Antonova, V.V., Ustavshchikov, B.F., and Titova, N.A., Chem. Heterocycl. Compd., 1975, vol. 11, p. 1349. https://doi.org/10.1007/BF00764521

    Article  Google Scholar 

  8. Mahan, J.E., USA Patent 2615022, 1952.

  9. Stoops, C.E., USA Patent 2745833, 1956.

  10. Becker C.E., USA Patent 2745835, 1956.

  11. Mahan, J.E. and Stoops, C.E., USA Patent 2749348, 1956.

  12. Chichibabin, A.E., Bull. Soc. Chim., 1937, no. 4, p. 1831. https://doi.org/10.1002/prac.19371480902

    Article  Google Scholar 

  13. Graf, R., J. Prakt. Chemie, 1938, no. 150, p. 153. https://doi.org/10.1002/prac.19381500602

    Article  CAS  Google Scholar 

  14. Frank, R.L., Blegen, J.R., Dearborn, R.J., Myers, R.L., and Woodward, F.E., J. Am. Chem. Soc., 1946, no. 68, p. 1368. https://doi.org/10.1021/ja01211a082

    Article  CAS  PubMed  Google Scholar 

  15. Schnizer, A.W. and Stautzenberger, A.L., USA Patent 2844583, 1958.

  16. Funabiki, A., Japan Patent 4810794, 1989.

  17. Rosac, C. and Wantuck, J., USA Patent 3846435, 1974.

  18. Rosas, С.J. and Kaufman, W.A., USA Patent 3846435, 1972.

  19. Moioli, E., Schmid, L., Wasserscheid, P., and Freund, H., React. Chem. Eng., 2017, no. 2, p. 754. https://doi.org/10.1039/C7RE00100B

    Article  CAS  Google Scholar 

  20. Grayson, J.I., Dinkel, R., and Lonzo, A.G., Helv. Chim. Acta, 1984, vol. 67, no. 5, p. 2100. https://doi.org/10.1002/hlca.19840670811

    Article  CAS  Google Scholar 

  21. Shaw, N.M., Robins, K.T., and Kiener, A., Adv. Synth. Catal., 2003, no. 345, p. 4. https://doi.org/10.1002/adsc.200390049

    Article  Google Scholar 

  22. Sagitullin, R.S., Shkil’, G.P., Nosonova, I.I., and Ferber, A.A., Chem. Heterocycl. Comp., 1996, vol. 32, no. 2, p. 2. https://doi.org/10.1007/BF01165434

    Article  Google Scholar 

  23. Shimizu, S., Abe, N., Dohba, M., Sato, H., and Hirose, K., Micropor. Mesopor. Mater., 1998, vol. 21, nos. 4–6, p. 447. https://doi.org/10.1016/S1387-1811(98)00052-3

    Article  CAS  Google Scholar 

  24. Krishna Mohan, K.V.V., Reddy, K.S.K., Narender, N., and Kulkarni, S.J., J. Molec. Catal., 2009, no. 298, p. 99. https://doi.org/10.1016/j.molcata.2008.10.010

    Article  CAS  Google Scholar 

  25. Pavlov, M.L., Levinbuk, M.I., Baklanov, V.B., Smirnov, V.K., Bodryja, A.B., Videneev, G.A., and Surkova, L.V., RU Patent 2151739, 2000.

  26. Travkina, O.S., Agliullin, M.R., Filippova, N.A., Khazipova, A.N., Danilova, I.G., Grigor’eva, N.G., Narender, N., Pavlov, M.L., and Kutepov, B.I., RSC Adv., 2017, no. 7, p. 32581. https://doi.org/10.1039/C7RA04742H

    Article  CAS  Google Scholar 

  27. Auroux, A., Calorimetry and Thermal Methods in Catalysis, New York: Springer, 2013, vol. 154. https://doi.org/10.1007/978-3-642-11954-5

Download references

Funding

The study described here was performed with financial support from the Russian Science Foundation (grant no. 20-63-46011).

Author information

Authors and Affiliations

  1. Institute of Petroleum Chemistry and Catalysis, Russian Academy of Sciences, 450075, Ufa, Russia

    N. G. Grigor’eva, N. A. Filippova, S. V. Bubennov, A. N. Khazipova, B. I. Kutepov & V. A. Dyakonov

Authors
  1. N. G. Grigor’eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. A. Filippova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Bubennov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. N. Khazipova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. B. I. Kutepov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. A. Dyakonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. G. Grigor’eva.

Ethics declarations

The authors declare no conflict of interest requiring disclosure in this article.

Additional information

Translated from Sovremennye Molekulyarnye Sita. Advanced Molecular Sieves, 2021, Vol. 3, No. 1, pp. 119–124.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Grigor’eva, N.G., Filippova, N.A., Bubennov, S.V. et al. Microporous and Micro-meso-macroporous Y Zeolites in the Synthesis of 2-Methyl-5-ethylpyridine. Pet. Chem. 61, 364–369 (2021). https://doi.org/10.1134/S0965544121030075

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0965544121030075

Keywords:

Search

Navigation