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Model of selectivity to methyl pelargonate in hydrocarbomethoxylation of 1-octene in the presence of the Pd(PPh3)2Cl2—PPh3—p-toluenesulfonic acid catalytic system

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Abstract

The model of selectivity to methyl pelargonate was developed for the hydrocarbomethoxylation of 1-octene catalyzed by the Pd(PPh3)2Cl2—PPh3—p-toluenesulfonic acid system (378 K). The ratio of the rate of methyl pelargonate formation to the sum of the rates of formation of three isomeric esters (reaction products) was accepted as the differential selectivity of the reaction. The model represents a system of equations relating the differential selectivity of the reaction to the CO pressure and concentrations of methanol, PPh3, and p-toluenesulfonic acid. The model adequately depicts the experimental data in a wide range of 1-octene conversions up to 95.5%. The regularities of a change in the reaction selectivity were substantiated using the hydride multiroute mechanism of hydrocarbomethoxylation of 1-octene.

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References

  1. A. L. Lapidus, S. D. Pirozhkov, Russ. Chem. Rev., 1989, 58, 117.

    Article  Google Scholar 

  2. C. J. Rodriguez, D. F. Foster, G. R. Eastham, D. J. Cole-Hamilton, Chem. Commun., 2004, 1720.

  3. M. Amézquita-Valencia, G. Achonduh, H. Alper, J. Org. Chem., 2015, 80, 6419.

    Article  Google Scholar 

  4. Kh. A. Suerbaev, N. Zh. Kudaibergenov, A. Vavasori, Russ. J. Gen. Chem., 2017, 87, 707.

    Article  CAS  Google Scholar 

  5. Kh. A. Suerbaev, N. Zh. Khudaibergenov, A. K. Kurmansitova Russ. J. Gen. Chem., 2016, 86, 2124.

    Article  CAS  Google Scholar 

  6. V. A. Aver’yanov, S. A. Batashev, N. T. Sevostianova, V. M. Zarytovsky, Catal. in Ind., 2005, 25.

  7. G. Kiss, Chem. Rev., 2001, 101, 3435.

    Article  CAS  Google Scholar 

  8. Yu. G. Noskov, E. S. Petrov, Kinet. Katal., 1994, 35, 728 [Kinet. Catal. (Engl. Transl.), 1994, 35].

    CAS  Google Scholar 

  9. E. S. Petrov, Zh. Fiz. Khim., 1988, 62, 2858 [J. Phyz. Chem. USSR (Engl. Transl.), 1988, 62].

    CAS  Google Scholar 

  10. I. E. Nifant’ev, S. A. Batashev, S. A. Toloraya, A. N. Tavtorkin, N. T. Sevostyanova, A. A. Vorobiev, V. V. Bagrov, V. A. Averyanov, J. Mol. Catal. A: Chem., 2011, 350, 64.

    Article  Google Scholar 

  11. A. Vavasori, L. Toniolo, G. Cavinato, J. Mol. Catal. A: Chem., 2003, 191, 9.

    Article  CAS  Google Scholar 

  12. A. Vavasori, G. Cavinato, L. Toniolo, J. Mol. Catal. A: Chem., 2001, 176, 11.

    Article  CAS  Google Scholar 

  13. M. Rosales, I. Pacheco, J. Medira, J. Fernandez, A. Gonzalez, R. Izquierdo, L. G. Melean, P. J. Baricelli, Catal. Lett., 2014, 144, 1717.

    Article  CAS  Google Scholar 

  14. S. A. Batashev, Cand. Sci. (Chem.) Dissertation, Tula State University, Tula, 2005, 134 pp. (in Russian).

  15. U. M. Dzhemilev, N. R. Popod’ko, E. V. Kozlova, Metallokompleksnyi kataliz v organicheskom sinteze. Alitsiklicheskie soedineniya [Metallocomplex Catalysis in Organic Synthesis. Alicyclic Compounds], Khimiya, Moscow, 1999, 648 pp. (in Russian).

  16. G. Cavinato, L. Toniolo, A. Vavasori, J. Mol. Catal. A: Chem., 2004, 219, 233.

    Article  CAS  Google Scholar 

  17. V. A. Aver’yanov, S. A. Batashev, N. T. Sevost’yanova, N. M. Nosova, Kinet. Catal., 2006, 47, 375.

    Article  Google Scholar 

  18. T. E. Kron, M. I. Terekhova, E. S. Petrov, Kinet. Catal., 2004, 45, 519.

    Article  CAS  Google Scholar 

  19. M. Sperrle, G. Consiglio, Chem. Ber./Recl., 1997, 130, 1557.

    Article  CAS  Google Scholar 

  20. A. Vavasori, L. Toniolo, J. Mol. Catal. A: Chem., 1996, 110, 13.

    Article  CAS  Google Scholar 

  21. R. V. Chaudhari, Industrial Catalytic Processes for Fine and Specially Chemicals, Elsevier Inc., Amsterdam, 2016.

    Google Scholar 

  22. G. Cavinato, L. Toniolo, J. Mol. Catal.: Chem., 1999, 143, 325.

    Article  CAS  Google Scholar 

  23. R. Naigre, T. Chenal, I. Ciples, P. Kalck, J. Organomet. Chem., 1994, 480, 91.

    Article  CAS  Google Scholar 

  24. M. N. Terekhova, A. B. Sigalov, N. E. Petrova, E. S. Petrov, Zh. Obshch. Khim., 1985, 55, 944 [J. Gen. Chem. USSR (Engl. Transl.), 1985, 55].

    CAS  Google Scholar 

  25. V. A. Averyanov, N. T. Sevostyanova, S. A. Batashev, A. A. Vorobiev, A. S. Rodionova, Russ. J. Phys. Chem. B, 2014, 8, 140.

    Article  CAS  Google Scholar 

  26. I. E. Nifant’ev, N. T. Sevostyanova, V. A. Averyanov, S. A. Batashev, A. A. Vorobiev, S. A. Toloraya, V. V. Bagrov, A. N. Tavtorkin, Appl. Catal. A: Gen., 2012, 449, 145.

    Article  Google Scholar 

  27. V. A. Aver’yanov, N. T. Sevost’yanova, S. A. Batashev, S. V. Nesol’enaya, Petrol. Chem., 2006, 46, 405.

    Article  Google Scholar 

  28. Yu. G. Noskov, A. I. Simonov, E. S. Petrov, Kinet. Catal., 2000, 41, 511.

    Article  CAS  Google Scholar 

  29. Yu. G. Noskov, E. S. Petrov, Kinet. Catal., 1997, 38, 520.

    CAS  Google Scholar 

  30. Yu. G. Noskov, E. S. Petrov, Kinet. Katal., 1993, 34, 1005 [Kinet. Catal. (Engl. Transl.), 1993, 34].

    CAS  Google Scholar 

  31. Yu. G. Noskov, E. S. Petrov, Russ. Chem. Bull., 2001, 50, 1839.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Tula State Lev Tolstoy Pedagogical University, 125 prosp. Lenina, 300026, Tula, Russian Federation

    S. A. Batashev & N. T. Sevostyanova

Authors
  1. S. A. Batashev
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  2. N. T. Sevostyanova
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Correspondence to S. A. Batashev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1561–1568, August, 2020.

This work was financially supported by the Government of the Tula Region (Agreement No. DS/130 of October 29, 2018).

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Batashev, S.A., Sevostyanova, N.T. Model of selectivity to methyl pelargonate in hydrocarbomethoxylation of 1-octene in the presence of the Pd(PPh3)2Cl2—PPh3—p-toluenesulfonic acid catalytic system. Russ Chem Bull 69, 1561–1568 (2020). https://doi.org/10.1007/s11172-020-2935-z

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  • DOI: https://doi.org/10.1007/s11172-020-2935-z

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