Skip to main content
Log in

New catalytic systems on the basis of chromium compounds for selective synthesis of 1-hexene and 1-octene

  • Published:
Petroleum Chemistry Aims and scope Submit manuscript

Abstract

Based on the analysis of scientific and patent literature published over the period from June, 2010 to February, 2016, data on catalytic metal complex systems on the basis of chromium with various degrees of oxidation in the reaction of selective tri- and/or tetramerization of ethylene have been systematized and described. Key information about catalytic systems exhibiting high selectivity for higher alpha-olefins (1-hexene and 1-octene) or their mixtures is surveyed.

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.

Similar content being viewed by others

References

  1. P.-A. Breuil, L. Magna, and H. Olivier-Bourbigou, Catal. Lett. 145, 173 (2015).

    Article  CAS  Google Scholar 

  2. J. T. Dixon, M. J. Green, F. M. Hess, and D. H. Morgan, J. Organomet. Chem. 689, 3641 (2004).

    Article  CAS  Google Scholar 

  3. T. Agapie, Coord. Chem. Rev. 255, 861 (2011).

    Article  CAS  Google Scholar 

  4. D. S. McGuinness, Chem. Rev. 111, 2321 (2011).

    Article  CAS  Google Scholar 

  5. S. Kinoshita, K. Kawamura, and T. Fujita, Chem.- Asian J. 6, 284 (2011).

    Article  CAS  Google Scholar 

  6. G. P. Belov, Pet. Chem. 52, 139 (2012).

    Article  CAS  Google Scholar 

  7. K. P. Bryliakov and E. P. Talsi, Coord. Chem. Rev. 256, 2994 (2012).

    Article  CAS  Google Scholar 

  8. A. Otero, J. Fernandez-Baeza, A. Lara-Sanchez, and L. F. Sanchez-Barba, Coord. Chem. Rev. 257, 1806 (2013).

    Article  CAS  Google Scholar 

  9. P. W. N. M. van Leeuwen, N. D. Clement, and M. J. L. Tschan, Coord. Chem. Rev. 255, 1499 (2011).

    Article  CAS  Google Scholar 

  10. F. Zhu, L. Wang, and H. Yu, Des. Monomers Polym. 14, 1 (2011).

    Article  CAS  Google Scholar 

  11. D. F. Wass, Dalton Trans. 8, 816 (2007).

    Article  Google Scholar 

  12. B. Hessen, J. Mol. Catal. A: Chem. 213, 129 (2004).

    Article  CAS  Google Scholar 

  13. A. Forestière, H. Olivier-Bourbigou, and L. Saussine, Oil Gas Sci. Technol. Rev. IFP 64, 649 (2009).

    Article  CAS  Google Scholar 

  14. V. Katla, S. Du, C. Redshaw, and W.-H. Sun, Rev. Catal. 1, 1 (2014).

    Google Scholar 

  15. D. Takeuchi and K. Osakada, Lecture Notes in Chemistry, vol. 85: Organometallic Reactions and Polymerization, Ed. by K. Osakada (Springer, Berlin, 2014).

    Google Scholar 

  16. S. Dagorne and C. Fliedel, Top. Organomet. Chem. 41, 125 (2013).

    CAS  Google Scholar 

  17. D. S. McGuinness, in Catalysis by Metal Complexes (Springer, Dordrecht, 2011), vol. 35, p. 1.

    Google Scholar 

  18. W. K. Reagen, EP Patent No. 0 417 477 (1995).

    Google Scholar 

  19. J. T. Dixon, M. J. Green, F. M. Hess, and D. H. Morgan, J. Organomet. Chem. 689, 3641 (2004).

    Article  CAS  Google Scholar 

  20. I. I. Khasbiullin, G. P. Belov, and A. I. Vilms, Russ. Chem. Bull. 60, 1158 (2011).

    Article  CAS  Google Scholar 

  21. Y. Wang, L. Wang, J. Chen, et al., React. Kinet. Mech. Catal 106, 177 (2012).

    Article  CAS  Google Scholar 

  22. A. I. Vilms, I. A. Babenko, and G. P. Belov, Pet. Chem. 54, 128 (2014).

    Article  CAS  Google Scholar 

  23. I. I. Khasbiullin, K. E. Kharlampidi, G. P. Belov, and A. I. Vil’ms, Pet. Chem. 51, 442 (2011).

    Article  CAS  Google Scholar 

  24. S. Tang, Z. Liu, X. Yan, N. Li, R. Cheng, X. He, B. Liu, Appl. Catal., A 481, 39 (2014).

    Article  CAS  Google Scholar 

  25. T. Jiang, R. Ji, H. Chen, C. Cao, G. Mao, Y. Ning, Chin. J. Chem. 29, 1149 (2011).

    Article  CAS  Google Scholar 

  26. T. M. Zilbershtein, A. A. Nosikov, A. I. Kochnev, et al., Pet. Chem. 52, 253 (2012).

    Article  CAS  Google Scholar 

  27. T. M. Zilbershtein, M. V. Lipskikh, V. A. Kardash, and V. V. Suvorova, US Patent No. 0 121 435 (2014).

    Google Scholar 

  28. T. M. Zilbershtein, M. V. Lipskikh, A. A. Nosikov, and G. V. Nesyn, EP Patent No. 2 529 832 (2012).

    Google Scholar 

  29. T. M. Zilbershtein, V. A. Kardash, M. V. Lipskikh, et al., Pet. Chem. 52, 335 (2012).

    Article  CAS  Google Scholar 

  30. T. M. Zilbershtein, V. A. Kardash, V. V. Suvorova, and A. K. Golovko, Appl. Catal., A 475, 371 (2014).

    Article  CAS  Google Scholar 

  31. J. R. Briggs, US Patent No. 4 668 838 (1987).

    Google Scholar 

  32. R. B. Steele and A. Katzakin, US Patent No. 3 968 135 (1976).

    Google Scholar 

  33. R. D. Knudsen, R. G. Abbott, B. E. Kreischer, et al., WO Patent No. 2007/024 504 (2007).

    Google Scholar 

  34. O. L. Sydora, R. D. Knudsen, and E. J. Baralt, US Patent No. 0 150 642 (2013).

    Google Scholar 

  35. B. E. Kreischer, R. D. Knudsen, and O. L. Sydora, EP Patent No. 2 349 561 (2014).

    Google Scholar 

  36. V. D. Makhaev, L. A. Petrova, K. A. Alferov, and G. P. Belov, Russ. J. Appl. Chem. 86, 1819 (2013).

    Article  CAS  Google Scholar 

  37. V. D. Makhaev, L. A. Petrova, G. P. Belov, and K. A. Alferov, RU Patent No. 2 553 995 (2015).

    Google Scholar 

  38. J. Y. Jeon, D. S. Park, D. H. Lee, et al., Dalton Trans. 44, 11004 (2015).

    Article  CAS  Google Scholar 

  39. O. L. Sydora, WO Patent No. 2011/137 027 (2011).

    Google Scholar 

  40. S. V. Kulangara, D. Haveman, B. Vidjayacoumar, et al., Organometallics 34, 1203 (2015).

    Article  CAS  Google Scholar 

  41. R. Duchateau, S. Licciulli, and S. Gambarotta, WO Patent No. 2014/069 989 (2014).

    Google Scholar 

  42. I. Vidyaratne, G. B. Nikiforov, S. I. Gorelsky, et al., Angew. Chem., Int. Ed. 48, 6552 (2009).

    Article  CAS  Google Scholar 

  43. A. Jabri, C. Mason, Y. Sim, et al., Angew. Chem., Int. Ed. 47, 9717 (2008).

    Article  CAS  Google Scholar 

  44. S. Licciulli, K. Albahily, V. Fomitcheva, et al., Angew. Chem., Int. Ed. 50, 2346 (2011).

    Article  CAS  Google Scholar 

  45. I. Y. Skobelev, V. N. Panchenko, O. Y. Lyakin, et al., Organometallics 29, 2943 (2010).

    Article  CAS  Google Scholar 

  46. M. Kreye, C. G. Daniliuc, M. Freytag, et al., Dalton Trans. 43, 9052 (2014).

    Article  CAS  Google Scholar 

  47. H. Toulhoat, T. D. Bruin, and P. Raybaud, US Patent No. 0 137 100 (2011).

    Google Scholar 

  48. H. Toulhoat, M. L. Fomena, and T. de Bruin, J. Am. Chem. Soc. 133, 2481 (2011).

    Article  CAS  Google Scholar 

  49. D. Cicmil, I. K. van Ravenhorst, J. Meeuwissen, et al., Catal. Sci. Technol. 6, 731 (2016).

    Article  CAS  Google Scholar 

  50. D. S. McGuinness, P. Wasserscheid, W. Keim, et al., J. Am. Chem. Soc. 125, 5272 (2003).

    Article  CAS  Google Scholar 

  51. Z. Mohamadnia, E. Ahmadi, M. N. Haghighi, and H. Salehi-Mobarakeh, Catal. Lett. 141, 474 (2011).

    Article  CAS  Google Scholar 

  52. E. Ahmadi, Z. Mohamadnia, and M. N. Haghighi, Catal. Lett. 141, 1191 (2011).

    Article  CAS  Google Scholar 

  53. N. B. Bespalova, D. N. Cheredilin, G. A. Kozlova, et al., RU Patent No. 2 470 707 (2012).

    Google Scholar 

  54. K. Albahily, S. Gambarotta, and R. Duchateau, Organometallics 30, 4655 (2011).

    Article  CAS  Google Scholar 

  55. C. N. Temple, S. Gambarotta, I. Korobkov, and R. Duchateau, Organometallics 26, 4598 (2007).

    Article  CAS  Google Scholar 

  56. K. Albahily, Y. Shaikh, Z. Ahmed, I. Korobkov, S. Gambarotta, R. Duchateau, Organometallics 30, 4159 (2011).

    Article  CAS  Google Scholar 

  57. M. J. Carney, B. L. Small, and O. L. Sydora, WO Patent No. 2015/094 207 (2015).

    Google Scholar 

  58. O. L. Sydora, B. L. Small, and M. J. Carney, US Patent No. 8 865 610 (2014).

    Google Scholar 

  59. O. L. Sydora, M. J. Carney, B. L. Small, et al., WO Patent No. 2011/082 192 (2011).

    Google Scholar 

  60. O. L. Sydora, T. C. Jones, B. L. Small, et al., ACS Catal. 2, 2452 (2012).

    Article  CAS  Google Scholar 

  61. O. L. Sydora, M. Carney, B. L. Small, J. C. Gee, S. Hutchison, US Patent No. 0 221 645 (2014).

    Google Scholar 

  62. M. J. Hanton, D. M. Smith, W. F. Gabrielli, and S. J. Evans, WO Patent No. 2013/168 103 (2013).

    Google Scholar 

  63. S. W. Ewart, B. W. Kolthammer, D. M. Smith, et al., WO Patent No. 2010/092 554 (2010).

    Google Scholar 

  64. T. Jiang, H. Chen, C. Cao, G. Mao, Y. Ning, Chin. Sci. Bull. 55, 3750 (2010).

    Article  CAS  Google Scholar 

  65. J. A. Suttil, P. Wasserscheid, D. S. McGuinness, et al., Catal. Sci. Technol. 4, 2574 (2014).

    Article  CAS  Google Scholar 

  66. S. Sa, S. M. Lee, and S. Y. Kim, J. Mol. Catal. A: Chem. 378, 17 (2013).

    Article  CAS  Google Scholar 

  67. M. M. Mogorosi, M. C. Maumela, and M. J. Overett, WO Patent No. 2014/181 248 (2014).

    Google Scholar 

  68. Y. Zhou, H. Wu, S. Xu, et al., Dalton Trans. 44, 9545 (2015).

    Article  CAS  Google Scholar 

  69. X. Gao and P. Zoricak, WO Patent No. 2013/110 170 (2013).

    Google Scholar 

  70. A. Woehl, A. Meiswinkle, H. Boelt, et al., WO Patent No. WO 2015/015 402 (2015).

    Google Scholar 

  71. M. C. Maumela, M. M. Mogorosi, M. S. Mokhadinyana, et al., WO Patent No. 2014/181 247 (2014).

    Google Scholar 

  72. E. J. M. de Boer, H. van der Heljden, Q. A. On, et al., WO Patent No. 2008/077 908 (2008).

    Google Scholar 

  73. T. E. Stennett, T. W. Hey, L. T. Ball, et al., Chem-CatChem. 5, 2946 (2013).

    CAS  Google Scholar 

  74. M. J. Overett, M. C. Maumela, M. M. Mogorosi, et al., Patent WO, 2013.

    Google Scholar 

  75. M. J. Overett, E. Grobler, S. J. Evans, and K. Blann, WO Patent No. 2013/168 102 (2013).

    Google Scholar 

  76. X. Gao and C. A. G. Carter, WO Patent No. 2012/045 147 (2012).

    Google Scholar 

  77. Y. Sun, Y. Chen, G. Mao, et al., Chin. Sci. Bull. 59, 2613 (2014).

    Article  CAS  Google Scholar 

  78. C. A. G. Carter and P. S. Chisholm, WO Patent No. 2011/140 629 (2011).

    Google Scholar 

  79. I. Jaber, C. A. G. Carter, E. Clavelle, et al., WO Patent No. 2011/130 822 (2011).

    Google Scholar 

  80. S. J. Brown, C. A. G. Carter, P. S. Chisholm, et al., WO Patent No. 2013/067 620 (2013).

    Google Scholar 

  81. P. Zoricak, S. J. Brown, and P. S. Chisholm, WO Patent No. 2014/094 114 (2014).

    Google Scholar 

  82. C. A. G. Carter, P. S. Chisholm, S. J. Brown, and I. Jaber, WO Patent No. 2012/051 698 (2012)

    Google Scholar 

  83. S. J. Brown, C. A. G. Carter, I. Jaber, et al., WO Patent No. 2012/142 693 (2012).

    Google Scholar 

  84. S. J. Brown, C. A. G. Carter, P. S. Chisholm, et al., WO Patent No. 2013/013 300 (2013).

    Google Scholar 

  85. T. Wang, X. Gao, P. Shi, et al., Appl. Petrochem. Res. 5, 143 (2015).

    Article  CAS  Google Scholar 

  86. A. J. Rucklidge, D. S. McGuinness, R. P. Tooze, et al., Organometallics 26, 2782 (2007).

    Article  CAS  Google Scholar 

  87. D. S. McGuinness, A. J. Rucklidge, R. P. Tooze, and A. M. Z. Slawin, Organometallics 26, 2561 (2007).

    Article  CAS  Google Scholar 

  88. T. E. Stennet, M. F. Haddow, and D. F. Wass, Organometallics 31, 6960 (2012).

    Article  CAS  Google Scholar 

  89. O. L. Sydora, WO Patent No. 2012/092 415 (2012).

    Google Scholar 

  90. G. Wang, S. Wang, Z. Yang, et al., US Patent No. 0 310 025 (2012).

    Google Scholar 

  91. T. Jiang, Y. Tao, X. Gao, et al., Chin. Sci. Bull. 57, 1510 (2012).

    Article  CAS  Google Scholar 

  92. M. L. Shozi and H. B. Friedrich, South African J. Chem. 65, 214 (2012).

    CAS  Google Scholar 

  93. H. Shao, H. Zhou, X. Guo, et al., Catal. Commun. 60, 14 (2015).

    Article  CAS  Google Scholar 

  94. H. Shao, Y. Li, X. Gao, et al., J. Mol. Catal. A: Chem. 390, 152 (2014).

    Article  CAS  Google Scholar 

  95. H. Shao, Y. Li, X. Gao, et al., Chin. Pet. Process. Petrochem. Technol. 16, 45 (2014).

    CAS  Google Scholar 

  96. M. J. Overett, K. Blann, A. Bollmann, et al., J. Mol. Catal. A: Chem. 283, 114 (2008).

    Article  CAS  Google Scholar 

  97. T.-K. Han, S.-O. Kang, and S.-K. Kim, US Patent No. 8 829 218 (2014).

    Google Scholar 

  98. S.-K. Kim, T.-J. Kim, J.-H. Chung, et al., Organometallics 29, 5805 (2010).

    Article  CAS  Google Scholar 

  99. V. V. Afanas’ev, N. B. Bespalova, G. A. Kozlova, et al., RU Patent No. 2 525 118 (2014).

    Google Scholar 

  100. T. K. Han, M. S. Jung, D. C. Shin, et al., WO Patent No. 2013/137 676 (2013).

    Google Scholar 

  101. J. Zhang, X. Wang, X. Zhang, et al., ACS Catal. 3, 2311 (2013).

    Article  CAS  Google Scholar 

  102. D. N. Cheredilin, A. M. Sheloumov, G. A. Kozlova, et al., RU Patent No. 2 549 897 (2015).

    Google Scholar 

  103. D. N. Cheredilin, A. M. Sheloumov, G. A. Kozlova, et al., RU Patent No. 2 5498 33 (2015).

    Google Scholar 

  104. Y. Shaikh, K. Albahily, M. Sutcliffe, et al., Angew. Chem., Int. Ed. 51, 1366 (2012).

    Article  CAS  Google Scholar 

  105. Y. Shaikh, J. Gurnham, K. Albahily, et al., Organometallics 31, 7427 (2012).

    Article  CAS  Google Scholar 

  106. Y. Yang, J. Gurnham, B. Liu, et al., Organometallics 33, 5749 (2014).

    Article  CAS  Google Scholar 

  107. A. Alzamly, S. Gambarotta, I. Korobkov, et al., Inorg. Chem. 53, 6073 (2014).

    Article  CAS  Google Scholar 

  108. J. E. Radcliffe, A. S. Batsanov, D. M. Smith, et al., ACS Catal. 5, 7095 (2015).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. A. Babenko.

Additional information

Dedicated to the 60th anniversary of Institute of Problems of Chemical Physics, Russian Academy of Sciences

Original Russian Text © K.A. Alferov, I.A. Babenko, G.P. Belov, 2017, published in Neftekhimiya, 2017, Vol. 57, No. 1, pp. 3–32.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alferov, K.A., Babenko, I.A. & Belov, G.P. New catalytic systems on the basis of chromium compounds for selective synthesis of 1-hexene and 1-octene. Pet. Chem. 57, 1–30 (2017). https://doi.org/10.1134/S0965544117010029

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0965544117010029

Keywords

Navigation