Skip to main content
SpringerLink
Log in

Mechanisms of alkylation of isobutane by butenes and H/D exchange in isobutane molecules on acid zeolites

  • Published:
Theoretical and Experimental Chemistry Aims and scope

The mechanisms of alkylation of isobutane by butenes are discussed. As a result of critical analysis of the literature on the regioselectivity of protonation of isobutane a mechanism of H/D exchange in the isobutane molecule at the acid centers is proposed as possible first stage of alkylation.

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

Similar content being viewed by others

References

  1. V. N. Ipatieff and A. V. Grosse, J. Am. Chem. Soc., 57, 1616–1621 (1935).

    Article  CAS  Google Scholar 

  2. B. T. Brooks, The chemistry of petroleum hydrocarbons, B. T. Brooks, C. E. Boord, S. S. Kurtz Jr., L. Schmerling (eds.), Reinhold Publ. Co., New York (1955), pp. 363–408.

  3. P. H. Emmett, Catalysis, Vol. VI: Alkylation, Isomerization, Polymerization, Cracking, and Hydroreforming, P. H. Emmett (ed.), Reinhold Publ. Co., New York (1958), pp. 1–41.

  4. W. E. Garwood and P. B. Venuto, J. Catal., 11, 175–177 (1968).

    Article  CAS  Google Scholar 

  5. F. W. Kirsch, J. D. Potts, and D. S. Barmby, J. Catal., 27, No. 1, 142–150 (1972).

    Article  CAS  Google Scholar 

  6. E. S. Mortikov, S. M. Zen’kovskii, N. V. Mostovoi, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1551–1553 (1974).

    Google Scholar 

  7. I. M. Gerzeliev, S. N. Khadzhiev, A. V. Lyuter, et al., Sb. Nauchn. Tr. Grozn. Neft. NII, No. 30, 30–34 (1976).

  8. K. I. Patrilyak, P. N. Galich, V. I. Khranovskaya, et al., Proc. of All-Union Conf. “Transformations of hydrocarbons on acid–base heterogeneous catalysts” [in Russian], Book of Abstr., Grozn. Neft. NII, Grozny (1977), pp. 126–128.

  9. K. I. Patrilyak, Yu. N. Sidorenko, and V. A. Bortyshevskii, Alkylation at Zeolites [in Russian], Naukova Dumka, Kiev (1991).

    Google Scholar 

  10. K. I. Patrilyak, V. A. Bortyshevskii, I. N. Tsyprik, et al., Dokl. Akad. Nauk SSSR, 283, No. 2, 384–387 (1985).

    CAS  Google Scholar 

  11. J. Weitkamp, Proc. of the Intern. Symp. Zeolite Catal., Siofok, May 13-16, 1985, Szeged (1985), pp. 271–290.

  12. A. K. Nowak, C. M. A. M. Mesters, A. M. Rigby, and D. Schulze, Prepr. Am. Chem. Soc., Div. Petr. Chem., 41, No. 4, 668–673 (1996).

    CAS  Google Scholar 

  13. K. I. Patrilyak and O. M. Taranookha, Prepr. Am. Chem. Soc., Div. Petr. Chem., 41, No. 4, 678–682 (1996).

    Google Scholar 

  14. N. Kob and R. S. Drago, Prepr. Am. Chem. Soc., Div. Petr. Chem., 41, No. 4, 682–685 (1996).

    CAS  Google Scholar 

  15. F. Avendano and J. Tejada, Prepr. Am. Chem. Soc., Div. Petr. Chem., 41, No. 4, 723–728 (1996).

    CAS  Google Scholar 

  16. Y. Zhuang and F. T. T. Ng, Appl. Catal. A, 190, Nos. 1/2, 137–147 (1999).

    Google Scholar 

  17. J. Weitkamp and Y. Traa, Catal. Today, 49, Nos. 1-3, 193–199 (1999).

    Article  CAS  Google Scholar 

  18. S. Sahebdelfar, M. Kazemeini, F. Khorasheh, and A. Badakhshan, Chem. Eng. Sci., 57, No. 17, 3611–3620 (2002).

    Article  CAS  Google Scholar 

  19. K. Yoo, E. C. Burckle, and P. G. Smirniotis, J. Catal., 211, No. 1, 6–18 (2002).

    CAS  Google Scholar 

  20. A. Feller, J.-O. Barth, A. Guzman, et al., J. Catal., 220, No. 1, 192–206 (2003).

    Article  CAS  Google Scholar 

  21. K. Yoo and P. G. Smirniotis, Appl. Catal. A, 246, No. 2, 243–251 (2003).

    Article  CAS  Google Scholar 

  22. C. Sievers, I. Zuazo, A. Guzman, et al., J. Catal., 246, 315–324 (2007).

    Article  CAS  Google Scholar 

  23. S. V. Nayak, Zeolites for Cleaner Processes: Alkylation of Isobutene and n-Butene, A PhD dissertation, Washington (2009).

  24. R. R. Shiriyazdanov, “Investigation of relationships for production and application of zeolite-containing catalysts of alkylation of isobutane by olefins” [in Russian], Author’s Abstract of Dissertation in competition for academic degree of Candidate of the Technical Sciences, Ufa (2011).

  25. P. Rao and S. R. Vatcha, Prepr. Am. Chem. Soc., Div. Petr. Chem., 41, No. 4, 685–692 (1996).

    CAS  Google Scholar 

  26. G. A. Olah, P. Batamack, D. Deffieux, et al., Appl. Catal. A, 146, No. 1, 107–117 (1996).

    Article  CAS  Google Scholar 

  27. G. A. Olah, E. Martinez, B. Torok, and G. K. S. Prakash, Catal. Lett., 161, Nos. 3/4, 105–110 (1999).

    Article  Google Scholar 

  28. F. C. Whitmore, Ind. Eng. Chem., 26, 94–95 (1934).

    Article  CAS  Google Scholar 

  29. L. Schmerling, J. Am. Chem. Soc., 66, No. 8, 1422–1423 (1944).

    Article  CAS  Google Scholar 

  30. L. Schmerling, J. Am. Chem. Soc., 61, 1152–1154 (1945).

    Article  Google Scholar 

  31. L. Schmerling, J. Am. Chem. Soc., 68, No. 2, 275–281 (1946).

    Article  CAS  Google Scholar 

  32. L. Schmerling, Ind. Eng. Chem., 45, No. 7, 1447–1455 (1953).

    Article  CAS  Google Scholar 

  33. Handbook of Chemistry and Physics, CRS Press, Inc., Florida (1981), p. D–84.

  34. V. O. Ionin, “Acidity and activity of zeolite catalysts for alkylation of isobutane by butenes” [in Ukrainian], Dissertation in competition for academic degree of Candidate of the Chemical Sciences, Kiev (2005).

  35. G. A. Olah, Y. Halpern, J. Shen, and Y. K. Mo, J. Am. Chem. Soc., 93, No. 5, 1256–1259 (1971).

    Article  CAS  Google Scholar 

  36. G. A. Olah, Usp. Khim., 44, No. 5, 793–867 (1975).

    Google Scholar 

  37. K. I. Patrilyak, V. A. Bortyshevskii, V. S. Gutyrya, et al., Dokl. Akad. Nauk SSSR, 282, No. 6, 1398–1401 (1985).

    CAS  Google Scholar 

  38. K. Tanabe, Solid Acids and Bases [Russian translation], Mir, Moscow (1973).

    Google Scholar 

  39. B. S. Umansky and W. K. Hall, J. Catal., 124, 97–108 (1990).

    Article  CAS  Google Scholar 

  40. L. M. Kustov, Ros. Khim. Zh., 42, Nos. 1/2, 163–175 (1998).

    CAS  Google Scholar 

  41. A. Feller, I. Zuazo, A. Guzman, et al., J. Catal., 216, 313–323 (2003).

    Article  CAS  Google Scholar 

  42. J. Sommer, M. Hachoumy, F. Garin, and J. Barthomeuf, J. Am. Chem. Soc., 116, 5491–5492 (1994).

    Article  CAS  Google Scholar 

  43. J. Sommer, D. Habermacher, M. Hachomy, et al., Appl. Catal., 46, 193–205 (1996).

    Google Scholar 

  44. J. Sommer, R. Jost, and M. Hachoumy, Catal. Today, 38, 309–319 (1997).

    Article  CAS  Google Scholar 

  45. J. Sommer, A. Sassi, M. Hachoumy, et al., J. Catal., 171, 391–397 (1997).

    Article  CAS  Google Scholar 

  46. J. Sommer and I. Bukala, Accounts Chem. Res., 26, 370–376 (1993).

    Article  CAS  Google Scholar 

  47. J. Sommer, I. Bukala, and M. Hachoumy, Res. Chem. Intermed., 8, 753–766 (1996).

    Article  Google Scholar 

  48. J. Sommer, I. Bukala, M. Hachoumy, and R. Jost, J. Am. Chem. Soc., 119, 3274–3279 (1997).

    Article  CAS  Google Scholar 

  49. J. Sommer, M. Hachoumy, F. Garin, et al., J. Am. Chem. Soc., 117, 1135–1136 (1995).

    Article  CAS  Google Scholar 

  50. L. K. Patrilyak and P. I. Bartosh, Teor. Éksp. Khim., 39, No. 3, 172–178 (2003). [Theor. Exp. Chem., 39, No. 3, 177–183 (2003) (English translation).]

    Google Scholar 

  51. K. I. Patrilyak, F. M. Bobonych, Yu. G. Voloshyna, et al., Catal. Today, 65, Nos. 2-4, 129–135 (2001).

    Article  Google Scholar 

  52. K. I. Patrilyak, L. K. Patrilyak, Yu. G. Voloshina, et al., Teor. Éksp. Khim., 47, No. 4, 199–207 (2011). [Theor. Exp. Chem., 47, No. 4, 205–214 (2011) (English translation).]

    Google Scholar 

  53. L. K. Patrilyak, “Heterogeneous-catalytic carbonium-ion transformation of hydrocarbons” [in Ukrainian], Dissertation in competition for academic degree of Doctor of Chemical Sciences, Kiev (2006).

  54. Yu. G. Voloshina, L. K. Patrilyak, V. V. Ivanenko, and K. I. Patrilyak, Teor. Éksp. Khim., 45, No. 4, 249–252 (2009). [Theor. Exp. Chem. 45, No. 4, 263–266 (2009) (English translation).]

    Google Scholar 

  55. M. J. Truitt, S. S. Toporek, R. Rovira-Hernandez, et al., J. Am. Chem. Soc., 126, No. 36, 11144–11145 (2004).

    Article  CAS  Google Scholar 

  56. M. J. Truitt, S. S. Toporek, R. Rovira-Truitt, and J. L. White, J. Am. Chem. Soc., 128, No. 6, 1847–1852 (2006).

    Article  CAS  Google Scholar 

  57. L. S. Sremaniak, J. L. Whitten, M. J. Truitt, et al., J. Phys. Chem. B, 110, 20762–20764 (2006).

    Article  CAS  Google Scholar 

  58. T. Buèko, L. Benco, J. Hafner, and J. G. Ángyán, J. Catal., 250, 171–183 (2007).

    Article  Google Scholar 

  59. G. J. Kramer, R. A. van Santen, C. A. Emels, and A. K. Nowak, Nature, 363, 529–531 (1993).

    Article  CAS  Google Scholar 

  60. J. Engelhardt, J. Valyon, React. Kinet. Catal. Lett., 74, 217–224 (2001).

    Article  CAS  Google Scholar 

  61. J. Valyon, J. Engelhardt, D. Kalló, and M. Hegedis, Catal. Lett., 82, 29–35 (2002).

    Article  CAS  Google Scholar 

  62. Y. D. Xia, W. M. Hua, Y. Tong, and Z. Gao, Chem. Commun., No. 18, 1899–1901 (1999).

  63. T. Buèko, L. Benco, O. Dubay, et al., J. Chem. Phys., 131, No. 21, 214508 (2009) (11 pp).

    Google Scholar 

  64. T. Buèko and J. Hafner, J. Phys.: Condens. Matter, 22, No. 38, 384201 (2010) (10 pp).

    Google Scholar 

  65. L. Benco, T. Buèko, and J. Hafner, J. Catal., 277, No. 1, 104–116 (2011).

    Article  CAS  Google Scholar 

  66. T. Buèko, L. Benco, J. Hafner, and J. G. Ángyán, J. Catal., 279, No. 1, 220–228 (2011).

    Article  Google Scholar 

  67. I. Milas, A. M. Silva, and M. A. Ch. Nascimento, Appl. Catal. A, 336, Nos. 1/2, 17–22 (2008).

    CAS  Google Scholar 

  68. J. F. Haw, M. B. Hall, A. E. Alvarado-Swaisgood, et al., J. Am. Chem. Soc., 116, 7308–7318 (1994).

    Article  CAS  Google Scholar 

  69. M. J. Truitt and J. L. White, Solid State Nucl. Magn. Reson. 35, No. 2, 100–103 (2009).

    Article  CAS  Google Scholar 

  70. J. Sommer and R. Jost, Pure Appl. Chem., 72, No. 12, 2309–2318 (2000).

    Article  CAS  Google Scholar 

  71. B. Louis, M. M. Pereira, F. M. Santos, et al., Chemistry, A Europ. J., 16, No. 2, 573–576 (2010).

    Article  CAS  Google Scholar 

  72. A. S. S. Sido, S. Walspurger, J. Barbiche, and J. Sommer, Chemistry, A Europ. J., No. 10, 3215–3221 (2010).

    Article  Google Scholar 

  73. A. S. S. Sido, J. Barbiche, and J. Sommer, Chem. Commun., 46, No. 17, 2913–2914 (2010).

    Article  Google Scholar 

  74. K. I. Patrilyak and L. K. Patrilyak, Katal. Neftekhim., No. 20, 6–21 (2012).

  75. A. Corma and A. V. Orchilles, Micropor. Mesopor. Mater., 35/36, 21–30 (2000).

    Article  Google Scholar 

  76. C. Thomas, Industrial Catalytic Processes and Effective Catalysts [Russian translation], Mir, Moscow (1973).

    Google Scholar 

  77. B. V. Nekrasov, Course of General Chemistry [in Russian], Goskhimizdat, Moscow (1962).

    Google Scholar 

  78. Yu. G. Voloshina, I. A. Repetskii, L. K. Patrilyak, and K. I. Patrilyak, Khim, Fiz. Tekhnol. Poverkhn., 14, 429–436 (2008).

    Google Scholar 

  79. M. V. Okhrimenko, V. V. Ivanenko, Yu. G. Voloshina, et al., Visn. Nats. Aviats. Univ., No. 1 (38), 150–156 (2009).

  80. V. V. Brei, Teor. Éksp. Khim., 41, No. 3, 156-166 (2005). [Theor. Exp. Chem., 41, No. 3, 165–175 (2005) (English translation).]

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Vul. Murmans’ka, 1, Kyiv, 02660, Ukraine

    K. I. Patrylak, L. K. Patrylak & I. A. Repetskyi

Authors
  1. K. I. Patrylak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. K. Patrylak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. A. Repetskyi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. I. Patrylak.

Additional information

Translated from Teoreticheskaya i Éksperimental’naya Khimiya, Vol. 49, No. 3, pp. 133-146, May-June, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Patrylak, K.I., Patrylak, L.K. & Repetskyi, I.A. Mechanisms of alkylation of isobutane by butenes and H/D exchange in isobutane molecules on acid zeolites. Theor Exp Chem 49, 143–157 (2013). https://doi.org/10.1007/s11237-013-9308-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11237-013-9308-8

Key words

Search

Navigation