Skip to main content
Log in

Opening of the rings of aromatic and naphthene hydrocarbons: A new way of improving the quality of fuels

  • General Review
  • Published:
Catalysis in Industry Aims and scope Submit manuscript

Abstract

In recent years, the opening of the rings of aromatic and naphthene hydrocarbons has been considered as a way way of improving the quality of motor fuels. In gasolines, the opening of monocyclic compounds like di- and trialkylcyclohexanes allows the synthesis of high-octane components (C7–C10 iso-paraffins). In diesel fuels containing considerable amounts of bi- and trinuclear polycyclic compounds such as derivatives of naphthalene (decaline), phenanthrene, and indane, this allows the synthesis of monocyclic compounds and alkanes, thus leading to a reduction in the freezing temperature of the fuel and, when obtaining predominantly linear alkanes, to an increase in the cetane number. In this work, we conduct a brief analysis of accumulated data on the opening of cyclic compounds on oxide and zeolite supported catalysts.

This is a preview of subscription content, log in via an institution to check access.

Access this article

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. Tailleur, R.G., Fuel Proc. Technol., 2006, vol. 87, no. 9, p. 759.

    Article  CAS  Google Scholar 

  2. Cusher, N.A., in Handbook of Petroleum Refining Processes, New York: McGraw-Hill, 1986.

    Google Scholar 

  3. McVicker, G.B., Daage, M., Touvelle, M.S., Hudson, C.W., et al., J. Catal., 2002, vol. 210, no. 1, p. 137.

    Article  CAS  Google Scholar 

  4. Vaarkamp, M., Dijkstra, P., Vangrondelle, J., Miller, J. T., et al., J. Catal., 1995, vol. 151, no. 2, p. 330.

    Article  CAS  Google Scholar 

  5. Martens, J.A., PhD Dissertation, Leuven: Kathol. Univ. Leuven, 1985.

    Google Scholar 

  6. Lam, Y.L. and Sinfelt, J.H., J. Catal., 1976, vol. 42, no. 2, p. 319.

    Article  CAS  Google Scholar 

  7. Anderson, J.B.F., Burch, R., and Cairns, J.A., J. Chem. Soc., Faraday Trans I., 1987, vol. 83, no. 3, p. 913.

    Article  CAS  Google Scholar 

  8. Sinfelt, J.H., J. Catal., 1973, vol. 29, no. 2, p. 308.

    Article  CAS  Google Scholar 

  9. Somorjai, G.A., Introduction to Surface Chemistry and Catalysis, New York: Wiley, 1994.

    Google Scholar 

  10. Török, B., Pálinkó, I., and Bartók, M., Catal. Lett., 1995, vol. 31, no. 4, p. 421.

    Article  Google Scholar 

  11. Schepers, F.J., van Senden, J.G., van Broekhoven, E.H., and Ponec V.J., J. Catal., 1985, vol. 94, no. 2, p. 400.

    Article  CAS  Google Scholar 

  12. Roberti, A., Ponec, V., and Sachtler, W. M. H., J. Catal., 1973, vol. 28, no. 3, p. 381.

    Article  CAS  Google Scholar 

  13. Bolivar, C., Charcosset, H., Frety, R., Primet, M., et al., J. Catal., 1976, vol. 45, no. 2, p. 163.

    Article  CAS  Google Scholar 

  14. Miki, Y., Yamadaya, S., and Oba, M., J. Catal., 1977, vol. 49, no. 3, p. 278.

    Article  CAS  Google Scholar 

  15. Du, H., Fairbridge, C., Yang, H., and Ring. Z., Appl. Catal., A: General, 2005, vol. 294, no. 1, p. 1.

    Article  CAS  Google Scholar 

  16. Sachtler, W.M.H. and Zhang, Z.C., Adv. Catal., 1993, vol. 39, p. 129.

    Article  CAS  Google Scholar 

  17. Dossi, C., Psaro R., Bartsch, A., Fusi, A., et al., J. Catal., 1994, vol. 145, no. 2, p. 377.

    Article  CAS  Google Scholar 

  18. Ostgard, D., Kustov, L.M., Poeppelmeier, K.R., and Sachtler, W.M.H., J. Catal., 1992, vol. 133, no. 2, p. 342.

    Article  CAS  Google Scholar 

  19. Paál, Z., J. Mol. Catal., 1994, vol. 94, no. 2, p. 225.

    Article  Google Scholar 

  20. Kubicka, H. and Okal, J., Catal. Lett., 1994, vol. 25, nos. 1–2, p. 157.

    Article  CAS  Google Scholar 

  21. Bragin, O.V. and Liberman, A.L., Prevrashcheniya uglevodorodov na metallsoderzhashchikh katalizatorakh (Conversion of Hydrocarbons on Metal-Containing Catalysts), Moscow: Khimiya, 1981.

    Google Scholar 

  22. Samoila, P., Boutzeloit, M., Especel, C., Epron, F., et al., J. Catal., 2010, vol. 276, no. 2, p. 237.

    Article  CAS  Google Scholar 

  23. Teschner, D., Matusek, K., and Paál, Z., J. Catal., 2000, vol. 192, no. 2, p. 335.

    Article  CAS  Google Scholar 

  24. Zhuang, Y. and Frennet, A., Appl. Catal. A: General, 1999, vol. 177, no. 2, p. 205.

    Article  CAS  Google Scholar 

  25. Teschner, D., Paál, Z., and Duprez, D., Catal. Today, 2001, vol. 65, nos. 2–4, p. 185.

    Article  CAS  Google Scholar 

  26. Brandenberger, S.G., Callender, W.L., and Meerbott, W.K., J. Catal., 1976, vol. 42, no. 2, p. 282.

    Article  CAS  Google Scholar 

  27. Samoila, P., Boutzeloit, M., Especel, C., Epron, F., et al., Appl. Catal. A: General, 2009, vol. 369, nos. 1–2, p. 104.

    Article  CAS  Google Scholar 

  28. Galperin, L.B., Bricker, J.C., and Holmgren, J.R., Appl. Catal. A: General, 2003, vol. 239, nos. 1–2, p. 297.

    Article  CAS  Google Scholar 

  29. Brower, D.M. and Hogeveen, H., Recl. Trav. Chim. Pays-Bas, 1970, vol. 89, p. 211.

    Article  Google Scholar 

  30. Onyestyák, G., Pál-Borbély, G., and Beyer, H.K., Appl. Catal., A: General, 2002, vol. 229, nos. 1–2, p. 65.

    Article  Google Scholar 

  31. Kubicka, H., J. Catal., 1968, vol. 12, no. 3, p. 223.

    Article  CAS  Google Scholar 

  32. FRG Patent 2127624, Chem. Abstr., 1972, vol. 76, no. 50630.

    Google Scholar 

  33. Kustov, L.M., Vasina, T.V., Masloboishchikova, O.V., Khelkovskaya-Sergeeva, E.G., et al., Stud. Surf. Sci. Catal., 2000, vol. 130, p. 227.

    Article  Google Scholar 

  34. Masloboishchikova, O.V., Vasina, T.V., Khelkovskaya-Sergeeva, E.G., Kustov, L.M., et al., Russ. Chem. Bull., 2002, vol. 51, no. 2, p. 249.

    Article  CAS  Google Scholar 

  35. Okuhara, J., Kyomasu, A., and Misono, M., J. Chem. Soc., Faraday Trans., 1991, vol. 87, no. 11, p. 1801.

    Article  CAS  Google Scholar 

  36. Bond, G.C. and Hooper, A.D., Appl. Catal. A: General, 2000, vol. 191, nos. 1–2, p. 69.

    Article  CAS  Google Scholar 

  37. Guczi, L., Stud. Surf. Sci. Catal., 1988, vol. 38, p. 85.

    Article  Google Scholar 

  38. Hamada, H., Appl. Catal., 1986, vol. 27, no. 2, p. 265.

    Article  CAS  Google Scholar 

  39. Chakrabarty, D.K., Rao, K.M., Sundararaman, N., and Chandavar, K., Appl. Catal., 1986, vol. 28, p. 69.

    Article  CAS  Google Scholar 

  40. Díaz, G., Garin, F., Maire, G., Alerasool, S., et al., Appl. Catal. A: General., 1995, vol. 124, no. 1, p. 33.

    Article  Google Scholar 

  41. DÍaz, G., Esteban, P., Guczi, L., Garin, F., et al., Stud. Surf. Sci. Catal., 1989, vol. 48, p. 363.

    Article  Google Scholar 

  42. Garin, F., Hilaire, L., and Maire, G., Stud. Surf. Sci. Catal., 1986, vol. 27, p. 145.

    Article  CAS  Google Scholar 

  43. Alerasooln, S. and Gonzalez, R.D., J. Catal., 1990, vol. 124, no. 1, p. 204.

    Article  Google Scholar 

  44. EEC Patent 875286, 1998.

  45. Vasina, T.V., Masloboishchikova, O.V., Khelkovskaya-Sergeeva, E.G., Kustov, L.M., et al., Stud. Surf. Sci. Catal., 2001, vol. 135, p. 159.

    Article  Google Scholar 

  46. Lecarpentier, S., van Gestel, J., Thomas, K., Gilson, J.-P., et al., J. Catal., 2008, vol. 254, no. 1, p. 49.

    Article  CAS  Google Scholar 

  47. Do, P.T., Alvarez, W.E., and Resasco, D.E., J. Catal., 2006, vol. 238, no. 2, p. 477.

    Article  CAS  Google Scholar 

  48. Santikunaporn, M., Alvarez, W.E., and Resasco, D.E., Appl. Catal. A: General, 2007, vol. 325, no. 1, p. 175.

    Article  CAS  Google Scholar 

  49. González-Cortés, S.L., Dorkjampa, S., Do, P.T., Lu, Z., et al., Chem. Eng. J., 2008, vol. 139, no. 1, p. 147.

    Article  CAS  Google Scholar 

  50. Dorkjampa, S., Rirksomboon, T., Phuong, D.T.M., and Resasco, D.E., J. Mol. Catal. A: Chem., 2007, vol. 274, nos. 1–2, p. 231.

    Article  CAS  Google Scholar 

  51. Mao, W., Ma, H., and Wang, B., J. Hazard. Mater., 2010, vol. 176, nos. 1–3, p. 361.

    Article  CAS  Google Scholar 

  52. US Patent 5382730 (USA), 1995.

  53. US Patent 5382731 (USA), 1995.

  54. Ivanov, A.V., Solid Superacids Based on the Compounds of Group IV-VI Elements and Their Catalytic Properties in the Isomerization of Aliphatic Hydrocarbons, Extended Abstract of Cand. Sci. (Chem.) Dissertation, Moscow: Zelinskii Inst. Org. Chem. Russ. Acad. Sci., 1997.

    Google Scholar 

  55. Shimizu, K., Sunagawa, T., Vera, C.R., and Ukegawa, K., Appl. Catal. A: General, 2001, vol. 206, no. 1, p. 79.

    Article  CAS  Google Scholar 

  56. Cunha, D. S., and Cruz, G. M., Appl. Catal. A: General, 2002, vol. 236, nos. 1–2, p. 55.

    Article  CAS  Google Scholar 

  57. Lin, S.D. and Vannice, M.A., J. Catal., 1993, vol. 143, no. 2, p. 539.

    Article  CAS  Google Scholar 

  58. Lietz, G. and Völter, J., J. Catal., 1976, vol. 45, no. 2, p. 121.

    Article  CAS  Google Scholar 

  59. Grenoble, D.C., J. Catal., 1979, vol. 56, no. 1, p. 32.

    Article  CAS  Google Scholar 

  60. Duprez, D., Miloudi, A., Delahay, G., and Maurel, R., J. Catal., 1984, vol. 90, no. 2, p. 292.

    Article  CAS  Google Scholar 

  61. Mozhaiko, V.N., Rabinovich, G.L., Maslyanskii, G.N., and Edryakova, L.P., Neftekhimiya, 1975, vol. 15, no. 1, p. 95.

    CAS  Google Scholar 

  62. Boitiaux, J.P., Cosyns, J., and Joesoef, A.K., Appl. Catal., 1982, vol. 3, no. 1, p. 89.

    Article  CAS  Google Scholar 

  63. Fu, J., Chem. J. Chin. Univ., 1995, vol. 16, no. 3, p. 461.

    Google Scholar 

  64. Li, W., Wang, Z., Zhang, M., and Tao, K., Catal. Commun., 2005, vol. 6, no. 10, p. 656.

    Article  CAS  Google Scholar 

  65. Kubicka, D., Kumar, N., Mäki-Arvela, P., Tiitta, M., et al., J. Catal., 2004, vol. 222, no. 1, p. 65.

    Article  CAS  Google Scholar 

  66. Kubicka, D., Salmi, T., Tiitta, M., and Murzin, D.Yu., Fuel, 2009, vol. 88, no 2, p. 366.

    Article  CAS  Google Scholar 

  67. Kubicka, D., Kumar, N., Mäki-Arvela, P. Tiitta, M., et al., J. Catal., 2004, vol. 227, no. 2, p. 313.

    CAS  Google Scholar 

  68. Kustov, L.M. and Stakheev, A.Yu., Abstracts of Papers, Proc. North Amer. Catal. Soc. Meeting, Toronto, 2001, p. 185.

  69. Kustov, L.M., Abstracts of Papers, Proc. 14 th Zeolite Conf., Capetown, 2004, p. 399.

  70. Stakheev, A.Yu. and Kustov, L.M., Appl. Catal. A: General, 1999, vol. 188. nos. 1–2, p. 3.

    Article  Google Scholar 

  71. Kustov, L.M., Stakheev, A.Yu., Vasina, T.V., Masloboishchikova, O.V., et al., Stud. Surf. Sci. Catal., 2001, vol. 138, p. 307.

    Article  CAS  Google Scholar 

  72. Santikunaporn, M., Herrera, J.E., Jongpatiwut, S., Resasco, D.E., et al., J. Catal., 2004, vol. 228, no. 1, p. 100.

    Article  CAS  Google Scholar 

  73. Arribas, M.A., Concepción, P., and Martínez, A., Appl. Catal. A: General, 2004, vol. 267, nos. 1–2, p. 111.

    Article  CAS  Google Scholar 

  74. Arribas, M.A., Corma, A., Díaz-Cabañas, M.J., and Martínez, A., Appl. Catal. A: General, 2004, vol. 273, nos. 1–2, p. 277.

    Article  CAS  Google Scholar 

  75. Eliche-Quesada, D., Mérida-Robles, J., Maireles-Torres, P., Rodríguez-Castellón, E., et al., J. Catal., 2003, vol. 220, no. 2, p. 457.

    Article  CAS  Google Scholar 

  76. Rodríguez-Castellón, E., Mérida-Robles, J., Díaz, L., Maireles-Torres, P., et al., Appl. Catal. A: General, 2004, vol. 260, no. 1, p. 9.

    Article  CAS  Google Scholar 

  77. Albertazzi, S., Rodríguez-Castellón, E., Livi, M., Jiménez-López, A., et al., J. Catal., 2004, vol. 228, no. 1, p. 218.

    Article  CAS  Google Scholar 

  78. Daage, M., Mc Vicker, G.B., Touvelle, M.S., Hudson, C.W., et al., Stud. Surf. Sci. Catal., 2001, vol. 135, p. 159.

    Article  Google Scholar 

  79. Chandra Mouli, K., Sundaramurthy, V., Dalai, A.K., and Ring, Z., Appl. Catal. A: General, 2007, vol. 321, no. 1, p. 17.

    Article  CAS  Google Scholar 

  80. Chandra Mouli, K., Sundaramurthy, V., and Dalai, A.K., J. Mol. Catal. A: Chem., 2009, vol. 304, nos. 1–2, p. 77.

    Article  CAS  Google Scholar 

  81. Ardakani, S.J., Liu, X., and Smith, K.J., Appl. Catal. A: General, 2007, vol. 324, p. 9.

    Article  CAS  Google Scholar 

  82. Liu, X. and Smith, K.J., Appl. Catal. A: General, 2008, vol. 335, no. 2, p. 230.

    Article  CAS  Google Scholar 

  83. Arribas, M.A. and Martínez, A., Appl. Catal. A: General, 2002, vol. 230, nos. 1–2, p. 203.

    Article  CAS  Google Scholar 

  84. Nylén, U., Sassu, L., Melis, S., Järås, S., et àl., Appl. Catal. A: General, 2006, vol. 299, p. 1.

    Article  CAS  Google Scholar 

  85. Nylén, U., Frontela Delgado, J., Järås, S., and Boutonnet, M., Appl. Catal. A: General, 2004, vol. 262, no. 2, p. 189.

    Article  CAS  Google Scholar 

  86. Castaño, P., Gutiérrez, A., Villanueva, I., Pawelec, B., et al., Catal. Today, 2009, vol. 143, nos. 1–2, p. 115.

    Article  CAS  Google Scholar 

  87. Chandra Mouli, K. and Dalai, A.K., Appl. Catal. A: General, 2009, vol. 364, nos. 1–2, p. 80.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Original Russian Text © L.M. Kustov, 2011, published in Kataliz v Promyshlennosti.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kustov, L.M. Opening of the rings of aromatic and naphthene hydrocarbons: A new way of improving the quality of fuels. Catal. Ind. 3, 358–369 (2011). https://doi.org/10.1134/S2070050411040040

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2070050411040040

Keywords

Navigation