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Catalytic Oxidation of Ethylene in Solutions of Palladium(II) Cationic Complexes in Binary and Ternary Aqueous Organic Solvents

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Abstract

The effect of organic solvents on the rate of ethylene oxidation with p-benzoquinone to acetaldehyde in aqueous organic solutions of palladium cationic complexes has been studied. It was found that the reaction rate increased when the acceptor number of the solvent increased and the donor number decreased. The oxidation of ethylene and cyclohexene in binary (N-methylpyrrolidone–H2O) and ternary (acetonitrile–N-methylpyrrolidone–H2O) solvents was studied in more detail. In contrast to the acetonitrile–Н2О system, in the N-methylpyrrolidone–Н2О binary solvent hydrogen peroxide oxidizes ethylene to acetaldehyde in the presence of Pd(II) cationic complexes. The use of a solvent N-methylpyrrolidone acceptable for cyclohexene (CH) oxidation technology leads to a decrease in the rate and selectivity of cyclohexanone synthesis.

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REFERENCES

  1. Moiseev, I.I., π-Kompleksy olefinov v zhidkofaznom okislenii (π-Complexes of Olephines in Liquid Phase Oxidation), Moscow: Nauka, 1970.

  2. Temkin, O.N., Kinet. Catal., 2020, vol. 61, no. 5, p. 663.

    Article  CAS  Google Scholar 

  3. Clement, W.H. and Selwitz, C.M., J. Org. Chem., 1964, vol. 29, p. 241.

    Article  CAS  Google Scholar 

  4. Fahey, D.R. and Zuech, E.A., J. Org. Chem., 1974, vol. 39, no. 22, p. 3276.

    Article  CAS  Google Scholar 

  5. Tsuji, J., Shimizu, I., and Yamamoto, K., Tetrahedron Lett., 1976, p. 2975.

  6. Tsuji, J., Synthesis, 1984, p. 369.

  7. Mitsudome, T., Umetani, T., Nosaka, N., Mori, K., Mizugaki, T., Ebitani, K., and Kaneda, K., Angew. Chem., Int. Ed., 2006, vol. 45, no. 3, p. 48.

    Article  Google Scholar 

  8. Fernandes, R.A. and Chaudhari, D.A., J. Org. Chem., 2014, vol. 79, issue 12, p. 5787.

    Article  CAS  Google Scholar 

  9. Kohno, M., Chem. Chem. Ind. (Jpn), 1988, vol. 41, no. 10, p. 936.

    Google Scholar 

  10. Wang, J.-l., He, L.-N., Miao, C.-X., and Li, Y.-N., Green Chem., 2009, vol. 11, p. 1317.

    Article  Google Scholar 

  11. Lloyd, W.G. and Luberoff, B.I., J. Org. Chem., 1969, vol. 34, p. 3949.

    Article  CAS  Google Scholar 

  12. Grigor’ev, A.A., Moiseev, I.I., Klimenko, M.Ya., and Lipina, Yu.N., Khim. Prom-st., 1972, vol. 48, p. 14.

    Google Scholar 

  13. Nishimura, T., Kakiuchi, N., Onoue, T., Ohe, K., and Uemura, S., J. Chem. Soc., Perkin Trans.1, 2000, p. 1915.

  14. Roussel, M. and Mimoun, H., J. Org. Chem., 1980, vol.45, no. 26, p. 5387.

    Article  CAS  Google Scholar 

  15. Tsuji, J. and Minato, M., Tetrahedron Lett., 1987, vol. 28, no. 32, p. 3683.

    Article  CAS  Google Scholar 

  16. Bäckvall, J.-E. and Hopkins, R.B., Tetrahedron Lett., 1988, vol. 29, no. 23, p. 2885.

    Article  Google Scholar 

  17. Wenzel, T.T., J. P. S. Chem. Commun. 1989, vol. 14, p. 932.

    Article  Google Scholar 

  18. Miller, D.G. and Wayner, D.D.M., J. Org. Chem., 1990, vol. 55, p. 2924.

    Article  CAS  Google Scholar 

  19. Scumov, M. and Balbolov, E., Catal. Lett., 2000, vol. 69, p. 103.

    Article  Google Scholar 

  20. Temkin O.N., Bruk L.G., Zakharova D.S., Odintsov K.Yu., Katsman E.A., PetrovI.V., and Istomina O.Yu., Kinet. Catal., 2010, vol. 51, no. 5, p. 691.

    Article  CAS  Google Scholar 

  21. Zakharova, D.S., Semenyako, A.N., Chertkova, O.A., Frolkova, A.V., Katsman, E.A., Bruk, L.G., and Temkin, O.N., Tonkie Khim. Tekhnol., 2015, vol. 10, no. 3, p. 77.

    CAS  Google Scholar 

  22. Zakharova, D.S., Martynov, I.V., Nosova, V.M., and Temkin, O.N., Tonkie Khim. Tekhnol., 2016, vol. 11, no. 2, p. 57.

    CAS  Google Scholar 

  23. Martynov, I.V., Efremov, G.E., Bovyrina, E.A., Katsman, E.A., and Temkin, O.N., Kinet. Catal., 2018, vol. 59, no. 4, p. 436.

    Article  CAS  Google Scholar 

  24. Efremov, G.E., Bovyrina, E.A., Podtyagina, A.V., Oshanina, I.V., and Temkin, O.N., Kinet. Catal., 2019, vol. 60, no. 1, p. 52.

    Article  CAS  Google Scholar 

  25. Efremov, G.E., Bovyrina, E.A., Katsman, E.A., Shamsiev, R.S., and Temkin, O.N., Izv. Akad. Nauk, Ser. Khim., 2019, no. 7, p. 1366.

  26. Zakharova, D.S., Chertkova, O.A., Chelkin, A.A., Bruk, L.G., and Temkin, O.N., Russ. Chem. Bull., 2013, vol. 62, p. 844.

    Article  CAS  Google Scholar 

  27. Martynov, I.V., Efremov, G.E., and Temkin, O.N., Russ. Chem. Bull., 2017, vol. 66, p. 922.

    Article  CAS  Google Scholar 

  28. Hayashi, T., Yamasaki, K., Mimura, H., and Uozumi, Y., J. Am. Chem. Soc., 2004, vol. 126, p. 3036.

    Article  CAS  Google Scholar 

  29. Michel, B.W., Camelio, A.M., Cornell, C.N., and Sigman, M.S., J. Am. Chem. Soc., 2009, vol. 131, p. 6076.

    Article  CAS  Google Scholar 

  30. Anderson, B.J., Keith, J. A., and Sigman, M.S., J. Am. Chem. Soc., 2010, vol. 132, p. 11872.

    Article  CAS  Google Scholar 

  31. Sigman, M.S. and Werner, E.W., Acc. Chem. Res., 2012, vol. 45, p. 874.

    Article  CAS  Google Scholar 

  32. Morandi, B., Wickens, Z. K., and Grubbs, R.H., Angew. Chem., Int. Ed., 2013, vol. 52, p. 2944.

    Article  CAS  Google Scholar 

  33. DeLuca, R.J., Edwards, J.L., Steffens, L.D., Michel, B.W., Oiao, X., Zhu, C., Coek, S.P., and Sigman, M.S., J. Org. Chem., 2013, vol. 78, p. 1682.

    Article  CAS  Google Scholar 

  34. Bigi, M.A. and White, M.C., J. Am. Chem. Soc., 2013, vol. 135, p. 7831.

  35. Walker, K.L., Dornan, L.M., Zare, R.N., Waymouth, R.M., and Muldoon, M.J., J. Am. Chem. Soc., 2017, vol. 139, p. 12495.

    Article  CAS  Google Scholar 

  36. Fukuoka, Y. and Nagahara, H., Sci. Technol. Catal., 1995, vol. 92, p. 375.

    Google Scholar 

  37. Nagahara, H., Ono, M., Konishi, M., and Fukuoka, Y., Appl. Surf. Sci., 1997, vol. 121/122, p. 448.

    Article  CAS  Google Scholar 

  38. Vargaftik, M.N., Moiseev, I.I., and Syrkin, Ya.K., Dokl. Akad. Nauk SSSR, 1961, vol. 139, p. 1396.

    CAS  Google Scholar 

  39. Kolb, M., Bratz, E., and Dialer, K., J. Mol. Catal., 1977, vol. 2, p. 399.

    Article  CAS  Google Scholar 

  40. Melgo, M.S., Lidner, A., and Schuchardt, U., Appl. Catal., A, 2004, vol. 273, p. 217.

  41. Frolkova, A., Zakharova, D., Frolkova, A., and Balbenov, S., Fluid Phase Equilib., 2016, vol. 408, p. 10.

    Article  CAS  Google Scholar 

  42. Jaworski, J.N., Mc Cann, S.D., Guzei, I.A., and Stahl, S.S., Angew. Chem., Int. Ed., 2017, vol. 56, p. 3605.

    Article  CAS  Google Scholar 

  43. Temkin, O.N., Gomogennyi metallokompleksnyi kataliz. Kineticheskie aspekty (Homogeneous Metal Complex Catalysis. Kinetic Aspects), Moscow: Akademkniga, 2008.

  44. Shmid, R. and Sapunov, V.N., Neformal’naya kinetika (Non-Formal Kinetics), Moscow: Mir, 1985.

  45. Fialkov, Yu.A., Rastvoritel’ kak sredstvo upravleniya khimicheskim protsessom (Solvent as a Tool of Controlling the Process), Leningrad: Khimiya, 1990.

  46. Lamb, J.D., Nazarenko, A.Y., and Hansen, R.J., Separation Sci. Technol., 1999, vol. 34, no. 13, p. 2583.

    Article  CAS  Google Scholar 

  47. Frolkova, A.V., Mayevskiy, M.A., and Smirnov, A.Y., J. Chem. Eng. Data, 2019, vol. 64, no. 5, p. 2888.

    Article  CAS  Google Scholar 

  48. Sen, A. and Lai T.W., Organometallics, 1982, vol. 1, p. 415.

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Authors and Affiliations

  1. Russian Technological University (Lomonosov Institute of Fine Chemical Technologies, MIREA), 119571, Moscow, Russia

    I. V. Oshanina, U. V. Pestunova, I. N. Rusnak & O. N. Temkin

  2. DNA-Technology, 117587, Moscow, Russia

    A. V. Podtyagina

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  1. I. V. Oshanina
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  2. A. V. Podtyagina
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  3. U. V. Pestunova
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  4. I. N. Rusnak
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  5. O. N. Temkin
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Correspondence to I. V. Oshanina.

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Translated by L. Smolina

Abbreviations and notation: CH, cyclohexene; DMF, dimethylformamide; AN, acetonitrile; NMP, N-methylpyrrolidone; DMSO, dimethyl sulfoxide; DMA, dimethyl acetamide; ADN, adipodinitrile; PhCH2CN, benzyl cyanide; AAc, acetic acid; t‑BuOH, tert-butanol; BQ, p-benzoquinone; CH-one, cyclohexanone; TSA, toluene sulfoacid: НХ, HClO4 or TSA; GLC, gas liquid chromatography; GAC, gas adsorption chromatography.

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Oshanina, I.V., Podtyagina, A.V., Pestunova, U.V. et al. Catalytic Oxidation of Ethylene in Solutions of Palladium(II) Cationic Complexes in Binary and Ternary Aqueous Organic Solvents. Kinet Catal 62, 734–743 (2021). https://doi.org/10.1134/S0023158421060148

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