Skip to main content
SpringerLink
Log in

Ethylene and Cyclohexene Oxidation by p-Benzoquinone, Hydrogen Peroxide, and Oxygen in the Solutions of Cationic Pd(II) Complexes in Acetonitrile–Water and Ionic Liquid–Water Binary Solvents

  • Published:
Kinetics and Catalysis Aims and scope Submit manuscript

Abstract

Optimal conditions are selected for ethylene and cyclohexene oxidation reactions in the acetonitrile (AN)–water system in the presence of \({\text{Pd}}{{({\text{AN}})}_{x}}({{{\text{H}}}_{2}}{\text{O}})_{{4 - x}}^{{2 + }}\) complexes. It is shown that hydrogen peroxide oxidizes hydroquinone (QН2) in acetonitrile solutions and in ionic liquids (\({\text{BMI}}{{{\text{M}}}^{ + }}{\text{BF}}_{4}^{ - },\)\({\text{BMI}}{{{\text{M}}}^{ + }}{\text{PF}}_{6}^{ - }\)), and the rates of ethylene oxidation in the \({\text{BMI}}{{{\text{M}}}^{ + }}{\text{PF}}_{6}^{ - }\) ionic liquid in the presence of p-benzoquinone (Q) and hydroquinone are the same. It is shown that solid and soluble phthalocyanine iron complexes catalyze oxidation of olefins by oxygen in acidic acetonitrile media by converting p-benzoquinone to the third catalyst of the process. The apparent first-order rate constants of hydroquinone oxidation by oxygen are determined. The use of the IL–Н2О–Н2SO4 system is found to be inappropriate for cyclohexanone synthesis because of the formation of byproducts of cyclohexene conversion.

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

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.

Similar content being viewed by others

REFERENCES

  1. Sen, A. and Lai, T.-W., J. Amer. Chem. Soc., 1981, vol. 103, p. 4627.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. Lai, T.-W. and Sen, A., Organometallics, 1984, vol. 3, p. 866.

    Article  CAS  Google Scholar 

  4. Hegedus, L.S., Mulbern, T.A., and Asada, H., J. Amer. Chem. Soc., 1986, vol. 108, p. 6224.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  9. Hahn, C., Morvillo, P., and Vitagliano, A., Eur. J. Inorg. Chem., 2001, p. 419.

  10. Cucciolito, M., Amora, A., and Vitagliano, A., Organometallics, 2005, vol. 24, p. 3359.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. Temkin, O.N., Kinet. Catal., 2014, vol. 55, no. 2, p. 172.

    Article  CAS  Google Scholar 

  13. Soriano, E. and Marco-Contelles, J., Top. Curr. Chem., 2011, vol. 302, p. 1.

    Article  CAS  PubMed  Google Scholar 

  14. Modern Gold Catalyzed Synthesis, Hashmi, A.S. and Toste, F.D., Eds., Weinheim: Wiley-VCH, 2012.

    Google Scholar 

  15. Temkin, O.N., Zakharova, D.S., Chertkova, O.A., Chelkin, A.S., and Bruk, L.G., Russ. Chem. Bull., 2013, vol. 62, no. 3, p. 844.

    Article  CAS  Google Scholar 

  16. Martynov, I.V., Efremov, G.E., and Temkin, O.N., Russ. Chem. Bull., 2017, vol. 66, no. 5, p. 922.

    Article  CAS  Google Scholar 

  17. Jira, R., Angew. Chem., 2009, vol. 48, p. 9034.

    Article  CAS  Google Scholar 

  18. Moiseev, I.I., π-Kompleksy v zhidkofaznom okislenii (π‑Complexes in Liquid Phase Oxidation), Moscow: Nauka, 1970.

  19. Ogata, H., Fujinami, H., and Taya, K., J. Chem. Soc. Chem. Commun., 1981, p. 1274.

  20. 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 

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

    CAS  Google Scholar 

  22. Kolb, M., Bratz, E., and Daler, K., J. Mol. Catal., 1977, p. 399.

  23. Takehira, K., Oh, H.J., Martinez, V.C., Chavira, R.S., Hyakawa, T., Orita, H., Shimitzu, M., and Ishikawa, T., J. Mol. Catal., 1987, vol. 42, p. 237.

    Article  CAS  Google Scholar 

  24. 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 

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

    Article  CAS  Google Scholar 

  26. Martynov, I.V., Efremov, G.E., Bovyrina, E.A., Katsman, E.A., and Temkin, O.N., Kinet. Katal., 2018.

  27. Moiseev, I.I., Vargaftik, M.N., and Syrkin, Ya.K., Dokl. Akad. Nauk SSSR, 1960, vol. 130, p. 820.

    CAS  Google Scholar 

  28. Matveev, K.I., Shitova, N.B., and Zhizhina, E.G., Kinet. Katal., 1976, vol. 17, no. 4, p. 893.

    CAS  Google Scholar 

  29. Zhizhina, E.G., Shitova, N.B., and Matveev, K.I., Kinet. Katal., 1981, vol. 22, no. 6, p. 1451.

    CAS  Google Scholar 

  30. Grennberg, H., Gogoll, A., and Backvall, J.-E., Organometallics, 1993, vol. 12, p. 1790.

    Article  CAS  Google Scholar 

  31. Roussel, M. and Mimoun, H., J. Org. Chem., 1980, vol. 45, p. 5387.

    Article  CAS  Google Scholar 

  32. Mimoun, H., Pure Appl. Chem., 1981, vol. 53, p. 2389.

    Article  CAS  Google Scholar 

  33. Mimoun, H., Angew. Chem., 1982, vol. 21, p. 734.

    Article  Google Scholar 

  34. Stahl, S.S., Angew. Chem., 2004, vol. 43, p. 3400.

    Article  CAS  Google Scholar 

  35. Popp, B.V. and Stahl, S.S., Top. Organomet. Chem., 2007, vol. 22, p. 149.

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives, Stahl, S.S. and Alsters, P.L., Eds., Weinheim: Wiley-VCH, 2016, p. 428.

    Google Scholar 

  38. Grennberg, H. and Backvall, J.E., J. Chem. Soc., Chem. Commun., 1993, p. 1331.

  39. Backvall, J.E., Awasthi, A.K., and Renko, Z.D., J. Am. Chem. Soc., 1987, vol. 109, no. 15, p. 4750.

    Article  Google Scholar 

  40. Grennberg, H., Faizon, S., and Backvall, J.E., Angew. Chem., 1993, vol. 32, no. 2, p. 263.

    Article  Google Scholar 

  41. Backvall, J.-E., Hopkins, R.B., Grennberg, H., Mader, M.M., and Awasthi, A.K., J. Am. Chem. Soc., 1990, vol. 112, p. 5160.

    Article  Google Scholar 

  42. Bystrom, S.E., Larsson, M.E., and Akermark, B., J. Org. Chem., 1990, vol. 55, p. 5674.

    Article  Google Scholar 

  43. Radel, R.J., Sullivan, J.M., and Hatfield, J.D., Ind. Eng. Chem. Prod. Res. Dev., 1982, vol. 21, no. 4, p. 566.

    Article  CAS  Google Scholar 

  44. Tevatia, P., Anuj, S., and Singh, R., J. Appl. Chem., 2014, vol. 7, p. 51.

    CAS  Google Scholar 

  45. Meng, X.-G., Guo, Y., Hu, C.-W., and Zeng, X.-C., J. Inorg. Biochem., 2004, vol. 98, p. 2107.

    Article  CAS  PubMed  Google Scholar 

  46. Wassercheid, P. and Keim, W., Angew. Chem., 2000, vol. 39, p. 3772.

    Article  Google Scholar 

  47. Namboodiri, V.V., Varma, R.S., Sahle-Demessie, E., and Pillai, U.R., Green Chem., 2002, vol. 4, p. 170.

    Article  CAS  Google Scholar 

  48. Seddon, K.R. and Stark, A., Green Chem., 2002, vol. 4, p. 119.

    Article  CAS  Google Scholar 

  49. Kustov, L.M., Vasina, T.V., and Ksenofontov, V.A., Ross. Khim. Zh., 2004, vol. 48, no. 6, p. 13.

    CAS  Google Scholar 

  50. Ionic Liquids in Synthesis, Wassercheid, P. and Welton, T., Eds., 2-nd ed., Weinheim: Wiley, 2008.

    Google Scholar 

  51. MacFarlane, D.R., Kar, M., and Pringle, J.M., Fundamentals of Ionic Liquids from Chemistry to Application, Weinheim: Wiley-VCH, 2017.

    Book  Google Scholar 

  52. Zagorodnikov, V.P., Ryabov, A.D., and Yatsimirskii, A.K., Kinet. Katal., 1981, vol. 22, no. 1, p. 131.

    Google Scholar 

  53. Stolyarov, I.P., Demina, L.I., and Cherkashina, N.V., Zh. Neorg. Khim., 2011, vol. 56, no. 10, p. 1611.

    Google Scholar 

  54. Mulagaleev, R.F., Kirik, S.D., and Golovnev, N.N., Zhurn. Sibirskogo Federal’nogo universiteta, Ser. Khimiya, 2008, vol. 1, no. 3, p. 249.

    Google Scholar 

  55. Bakhmutov, V.I., Berry, J.F., Cotton, F.A., Ibragimov, S., and Murillo, C.A., Dalton Trans., 2005, p. 1989.

  56. Nosova, V.M., Ustynyuk, Y.A., Bruk, L.G., Temkin, O.N., Kisin, A.V., and Storozhenko, P.A., Inorg. Chem., 2011, vol. 50, no. 19, p. 9300.

    Article  CAS  PubMed  Google Scholar 

  57. Masaoka, S., Akiyama, G., Horike, S., Kiagawa, S., Ida, T., and Endo, K., J. Am. Chem. Soc., 2003, vol. 123, p. 1152.

    Article  CAS  Google Scholar 

  58. Manahan, S. and Iwamoto, R.T., Electroanal. Chem. Interfacial Elektrochem., 1967, vol. 98, p. 2107.

    Google Scholar 

  59. Temkin, O.N., Homogeneous Catalysis with Metal Complexes. Kinetic Aspects and Mechanisms, ch. 8, Chichester: Wiley, 2014.

    Google Scholar 

  60. Frolkova, A.V., Balbenov, A.K., Frolkova, A.K., and Akishina, A.A., Russ. Chem. Bull., 2015, no. 10, p. 2330.

  61. Temkin, O.N., O Razlichnykh vzaimosvyazyakh kinetiki i termodinamiki (On the Various Interconnections of Kinetics and Thermodynamics), Saarbrucken: LAMBERT Academic Publishing, 2016.

Download references

ACKNOWLEDGMENTS

This work was supported by the Russian Science Foundation (project 16-19-10632, I.V. Oshanina and G.E. Efremov).

The authors thank Professors O.L. Kaliya and E.A. Luk’yanets for providing us with the samples of phthalocyanine complexes.

Author information

Authors and Affiliations

  1. MIREA–RussianTechnological University (M.V. Lomonosov Institute of Fine Chemical Technologies), 119571, Moscow, Russia

    G. E. Efremov, E. A. Bovyrina, A. V. Podtyagina, I. V. Oshanina & O. N. Temkin

Authors
  1. G. E. Efremov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. A. Bovyrina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Podtyagina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. V. Oshanina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. N. Temkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. N. Temkin.

Additional information

Translated by Andrey Zeigarnik

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Efremov, G.E., Bovyrina, E.A., Podtyagina, A.V. et al. Ethylene and Cyclohexene Oxidation by p-Benzoquinone, Hydrogen Peroxide, and Oxygen in the Solutions of Cationic Pd(II) Complexes in Acetonitrile–Water and Ionic Liquid–Water Binary Solvents. Kinet Catal 60, 52–61 (2019). https://doi.org/10.1134/S0023158419010051

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0023158419010051

Keywords:

Search

Navigation