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Coupled process of aldol condensation/hydrogenation of methyl ethyl ketone in the presence of a bifunctional heterogeneous catalyst

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Abstract

The processes of catalytic homocondensation of methyl ethyl ketone (MEK) in the presence of basic and acid heterogeneous catalysts were studied. A Pd/activated carbon catalytic system was proposed for coupling the processes of MEK condensation and hydrogenation of its products. It was found that high selectivity (more than 90%) for the sum of two condensation/hydrogenation products (5-methylheptan-3-one and 3-methylheptane) can be achieved in a hydrogen atmosphere, with the MEK conversion reaching up to 43%.

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References

  1. M. S. Kobzev, A. A. Titov, A. V. Varlamov, Russ. Chem. Bull., 2021, 70, 1213–1259; DOI: https://doi.org/10.1007/s11172-021-3208-1.

    Article  CAS  Google Scholar 

  2. V. V. Loza, Z. R. Valiullina, M. S. Miftakhov, Russ. Chem. Bull., 2021, 70, 1–31; DOI: https://doi.org/10.1007/s11172-021-3052-3.

    Article  CAS  Google Scholar 

  3. V. O. Samoilov, R. S. Borisov, T. I. Stolonogova, D. P. Zarezin, A. L. Maximov, M. V. Bermeshev, E. A. Chernysheva, V. M. Kapustin, Fuel, 2020, 280, 1–12; DOI: https://doi.org/10.1016/j.fuel.2020.118585.

    Article  Google Scholar 

  4. E. M. Martsinkevich, L. G. Bruk, L. V. Dashko, A. A. Afaunov, V. R. Flid, I. V. Sedov, Petrol. Chem., 2018, 58, 686–689; DOI: https://doi.org/10.1134/S0965544118120083.

    Article  Google Scholar 

  5. S. I. Filimonov, N. G. Savinsky, E. M. Evstigneeva, Mendeleev Commun., 2003, 13, 194–197; DOI: https://doi.org/10.1070/MC2003v013n04ABEH001687.

    Article  Google Scholar 

  6. W. Xue, B. Gu, H. Wu, M. Liu, S. He, J. Li, X. Rong, C. Sun, Appl. Catal. A: General, 2021, 616, 118107; DOI: https://doi.org/10.1016/j.apcata.2021.118107.

    Article  CAS  Google Scholar 

  7. L. V. Dashko, D. V. Dmitriev, S. M. Pestov, V. R. Flid, Russ. J. Organ. Chem., 2014, 50, 1732–1737; DOI: https://doi.org/10.1134/S1070428014120021.

    Article  CAS  Google Scholar 

  8. Z. Al-Auda, H. Al-Atabi, K. L. Hohn, Catalysts, 2018, 8, 622; DOI: https://doi.org/10.3390/catal8120622.

    Article  Google Scholar 

  9. P. A. Kots, A. V. Zabilska, E. V. Khramov, Y. V. Grigoriev, Y. V. Zubavichus, I. I. Ivanova, Inorg. Chem., 2018, 57, 11978–11985; DOI: https://doi.org/10.1021/acs.inorgchem.8b01548.

    Article  CAS  Google Scholar 

  10. E. M. Martsinkevich, A. A. Afaunov, V. R. Flid, L. G. Bruk, Russ. Chem. Bull., 2021, 70, 2031–2033; DOI: https://doi.org/10.1007/s11172-021-3313-1.

    Article  CAS  Google Scholar 

  11. E. Vrbková, T. Kovářová, E. Vyskočilová, L. Červený, Progress in Reaction Kinetics and Mechanism, 2019, 45, 1–10; DOI: https://doi.org/10.1177/1468678319825713.

    Google Scholar 

  12. M. A. Nasseri, A. Allahresani, H. Raissi, Iran. J. Catal., 2014, 4, 33–40.

    CAS  Google Scholar 

  13. Pat. RF No. 2739257, 2020. Byul. Izobret. [Invention Bull.], 2020, No. 36 (in Russian).

  14. O. N. Temkin, L. G. Bruk, D. Bonchev, Theor. Experimental Chem. (Engl. Transí), 1988, 24, 275–284; DOI: https://doi.org/10.1007/BF00534552.

    Article  Google Scholar 

  15. L. G. Bruk, O. N. Temkin, Kinet. Catal., 2016, 57, 277–296; DOI: https://doi.org/10.1134/S0023158416030022.

    Article  CAS  Google Scholar 

  16. A. I. Musin, Y. G. Borisova, G. Z. Raskil’dina, R. U. Rabaev, R. R. Daminev, S. S. Zlotskii, Fine Chem. Technol. (Engl. Transl.), 2020, 15, No. 5, 16–25; DOI: https://doi.org/10.32362/2410-6593-2020-15-5-16-25.

    Article  CAS  Google Scholar 

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Correspondence to A. A. Afaunov.

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Dedicated to Academician of the Russian Academy of Sciences V. A. Tartakovsky on the occasion of his 90th birthday.

The authors are grateful to Ph. D. (Phys.-Math.) D. A. Cheshkov for his help in recording and interpreting the NMR spectra.

The work was performed using the equipment of the Center for Collective Use of the Russian Technological University MIREA (CCU RTU MIREA) which received financial support from the Ministry of Science and Higher Education of the Russian Federation within the Agreement No. 075-15-2021-689 dated 01.09.2021.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1940–1948, September, 2022.

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Afaunov, A.A., Martsinkevich, E.M., Turischeva, E.E. et al. Coupled process of aldol condensation/hydrogenation of methyl ethyl ketone in the presence of a bifunctional heterogeneous catalyst. Russ Chem Bull 71, 1940–1948 (2022). https://doi.org/10.1007/s11172-022-3612-1

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  • DOI: https://doi.org/10.1007/s11172-022-3612-1

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