Skip to main content
Log in

Kinetics of Selective Trimerization of Ethylene to 1-Hexene over Chromium-Based Catalysts

  • Published:
Petroleum Chemistry Aims and scope Submit manuscript

Abstract

This review provides an analysis of prior research on the kinetics of the trimerization of ethylene to 1-hexene over existing chromium-based catalytic systems. It discusses the known mechanisms and reaction steps for the formation of 1-hexene as well as olefin by-products. The effects of catalytic system composition, temperature, pressure, reaction time, and the presence of hydrogen on the kinetics of 1-hexene formation are also touched upon. The kinetic models of ethylene trimerization to 1-hexene known from published literature are presented.

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.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.
Fig. 10.
Fig. 11.
Fig. 12.
Fig. 13.

Notes

  1. IHS Chemical. Light linear alpha olefin market study. Special report prospectus. https://cdn.ihs.com/www/pdf/IHS-Chemical-Linear-Alpha-Olefin-SRProspectus.pdf.

REFERENCES

  1. Ziegler von, K., Gellert, H.-G., and von Ziegler, K., Justus Liebigs Annalen der Chemie, 1950, vol. 567, no. 1, pp. 195–203. https://doi.org/10.1002/jlac.19505670112

    Article  Google Scholar 

  2. Ziegler, K., Gellert, H.-G., Martin, H., Nagel, K., and Schneider, J., Justus Liebigs Annalen der Chemie, 1954, vol. 589, no. 2, pp. 91–121. https://doi.org/10.1002/jlac.19545890202

    Article  CAS  Google Scholar 

  3. Wilke, G., Ang. Chem. Int. Ed., 2003, vol. 42, no. 41, pp. 5000–5008. https://doi.org/10.1002/anie.200330056

    Article  CAS  Google Scholar 

  4. Bianchini, C., Giambastiani, G., Rios, I.G., Mantovani, G., Meli, A., and Segarra, A.M., Coord. Chem. Rev., 2006, vol. 250, nos. 11–12, pp. 1391–1418. https://doi.org/10.1016/j.ccr.2005.12.018

    Article  CAS  Google Scholar 

  5. Matkovskii, P., Irzhak, V., and Mel’nikov, V., Vysokomol. Soed., Ser. A, 1993, vol. 35, no. 2, pp. 207–211.

    CAS  Google Scholar 

  6. Dixon, J.T., Green, M.J., Hess, F.M., and Morgan, D.H., J. Organomet. Chem., 2004, vol. 689, no. 23, pp. 3641–3668. https://doi.org/10.1016/j.jorganchem.2004.06.008

    Article  CAS  Google Scholar 

  7. Wass, D.F., Dalton. Trans., 2007, no. 8, pp. 816–819. https://doi.org/10.1039/b616291f

    Article  CAS  Google Scholar 

  8. McGuinness, D.S., Chem. Rev., 2011, vol. 111, no. 3, pp. 2321–2341. https://doi.org/10.1021/cr100217q

    Article  CAS  PubMed  Google Scholar 

  9. Agapie, T., Coord. Chem. Rev., 2011, vol. 255, nos. 7–8, pp. 861–880. https://doi.org/10.1016/j.ccr.2010.11.035

    Article  CAS  Google Scholar 

  10. Alferov, K.A., Belov, G.P., and Meng, Y., Appl. Catal. A: Gen., 2017, vol. 542, pp. 71–124. https://doi.org/10.1016/j.apcata.2017.05.014

    Article  CAS  Google Scholar 

  11. Bariashir, C., Huang, C., Solan, G.A., and Sun, W.-H., Coord. Chem. Rev., 2019, vol. 385, pp. 208–229. https://doi.org/10.1016/j.ccr.2019.01.019

    Article  CAS  Google Scholar 

  12. Salian, S.M., Bagui, M., and Jasra, R.V., Appl. Petrochem. Res., 2021, vol. 11, pp. 267–279. https://doi.org/10.1007/s13203-021-00279-7

    Article  CAS  Google Scholar 

  13. Tembe, G., Catal. Rev., 2022, vol. 65, no. 4, pp. 1412–1467. https://doi.org/10.1080/01614940.2021.2014638

    Article  CAS  Google Scholar 

  14. Briggs, J.R. and Briggs, J.R., J. Chem. Soc., Chem. Commun., 1989, no. 11, pp. 674. https://doi.org/10.1039/C39890000674

    Article  Google Scholar 

  15. Freeman, J.W., Buster, J.L., and Knudsen, R.D., Patent US 5856257 A, 1999.

  16. Freeman, J.W., Ewert, W.M., Kreischer, B.E., Knudsen, R.D., and Cowan, G.D., Patent US 6455648 B1, 2002.

  17. Keim, W., Ang. Chem. Int. Ed., 1990, vol. 29, no. 3, pp. 235–244. https://doi.org/10.1002/anie.199002351

    Article  Google Scholar 

  18. Jabri, A., Mason, C.B., Sim, Y., Gambarotta, S., and Burchell, T.J., Ang. Ion, 2008, vol. 48. 7, no. 50, pp. 9717–9721. https://doi.org/10.1002/anie.200803434

    Article  CAS  Google Scholar 

  19. Venderbosch, B., Oudsen, J.-P.H., Wolzak, L.A., Martin, D.J., Korstanje, T.J., Tromp, M., ACS Catal., 2018, vol. 9, no. 2, pp. 1197–1210. https://doi.org/10.1021/acscatal.8b03414

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Vadake Kulangara, S., Haveman, D., Vidjayacoumar, B., Korobkov, I., Gambarotta, S., and Duchateau, R., Organometallics, 2015, vol. 34, no. 7, pp. 1203–1210. https://doi.org/10.1021/om501013m

    Article  CAS  Google Scholar 

  21. Sydora, O.L., Patent US 8471085 B2, 2013.

  22. Tang, S., Liu, Z., Yan, X., Korobkov, I., Gambarotta, S., and Duchateau, R., Appl. Catal. A: Gen., 2014, vol. 481, pp. 39–48. https://doi.org/10.1016/j.apcata.2014.04.006

    Article  CAS  Google Scholar 

  23. Zilbershtein, T., Kardash, V., Lipskikh, M., Suvorova, V.V., and Golovko, A.K., Petrol. Chem., 2012, vol. 52, no. 5, pp. 335–340. https://doi.org/10.1134/S096554411205013

    Article  CAS  Google Scholar 

  24. Zilbershtein, T.M., Kardash, V.A., Suvorova, V.V., and Golovko, A.K., Appl. Catal. A: Gen., 2014, vol. 475, pp. 371–378. https://doi.org/10.1016/j.apcata.2014.01.051

    Article  CAS  Google Scholar 

  25. Bahri-Laleh, N., Karimi, M., Kalantari, Z., Fallah, M., Hanifpour, A., Nekoomanesh-and Haghighi, M., Polymer Bull., 2018, vol. 75, no. 8, pp. 3555–3565. https://doi.org/10.1007/s00289-017-2228-3

    Article  CAS  Google Scholar 

  26. Jiang, T., Zhang, L., Gao, J., and Cao, C., Appl. Petrochem. Res., 2016, vol. 6, no. 4, pp. 413–417. https://doi.org/10.1007/s13203-016-0151-4

    Article  CAS  Google Scholar 

  27. Woodard, W.M., Ewert, W.M., Hensley, H.D., Lashier, M.E., Kreischer, B.E., Cowan, G.D., Freeman, J.W., Franklin, R.V., Knudsen, R.D., Anderson, R.L., and Kallenbach, L.R., Patent WO 1999019280 A1, 1999.

  28. Araki, Y., Nakamura, H., Nanba, Y., Okano, T., Patent US 5856612 A, 1999.

  29. Luo, H.-K., Li, D.-G., Li, S., and Luo, H.-K., J. Mol. Catal. A: Chem., 2004, vol. 221, no. 1–2, pp. 9–17. https://doi.org/10.1016/j.molcata.2004.05.037

    Article  CAS  Google Scholar 

  30. Walsh, R., Morgan, D.H., Bollmann, A., and Dixon, J.T., Appl. Catal. A: Gen., 2006, vol. 306, pp. 184–191. https://doi.org/10.1016/j.apcata.2006.03.055

    Article  CAS  Google Scholar 

  31. Carter, A., Cohen, S.A., Cooley, N.A., Murphy, A., Scutta, J., and Wass, D.F., Chem. Commun., 2002, no. 8, pp. 858–859. https://doi.org/10.1039/B201335E

    Article  Google Scholar 

  32. Wass, D.F., Patent WO 0204119 A1, 2002.

  33. Dossett, S.J., Gillon, A., Orpen, A.G., Fleming, J.S., Pringle, P.G., Wass, D.F., and Jones, M.D., Chem. Commun., 2001, no. 8, pp. 699–700. https://doi.org/10.1039/B010063N

    Article  Google Scholar 

  34. Do, L.H., Labinger, J.A., and Bercaw, J.E., Organometallics, 2012, vol. 31, no. 14, pp. 5143–5149. https://doi.org/10.1021/om300492r

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Gong, M., Liu, Z., Li, Y., Ma, Y., Sun, Q., Zhang, J., and Liu, B., Organometallics, 2016, vol. 35, no. 7, pp. 972–981. https://doi.org/10.1021/acs.organomet.5b01029

    Article  CAS  Google Scholar 

  36. Blann, K., Bollmann, A., Dixon, J.T., Hess, F.M., Killian, E., Maumela, H., Morgan, D.H., Neveling, A., Otto, S., and Overett, M.J., Chem. Commun., 2005, no. 5, pp. 620–621. https://doi.org/10.1039/B412431F

    Article  Google Scholar 

  37. Nifant’ev, I.E., Vinogradov, A.A., Vinogradov, A.A., Roznyatovsky, V.A., Grishin, Y.K., Ivanyuk, A.V., Sedov, I.V., Churakov, A.V., and Ivchenko, P.V., Organometallics, 2018, vol. 37, no. 16, pp. 2660–2664. https://doi.org/10.1021/acs.organomet.8b00427

    Article  CAS  Google Scholar 

  38. Zhang, J., Braunstein, P., Hor, T.A., and Zhang, J., Organometallics, 2008, vol. 27, no. 17, pp. 4277–4279. https://doi.org/10.1021/om8005239

    Article  CAS  Google Scholar 

  39. Peitz, S., Peulecke, N., Aluri, B.R., Hansen, S., Müller, B.H., Spannenberg, A., Rosenthal, U., Al-Hazmi, M.H., Mosa, F.M., and Wöhl, A., Eur. J. Inorg. Chem., 2010, vol. 2010, pp. 1167–1171. https://doi.org/10.1002/ejic.201000044

    Article  CAS  Google Scholar 

  40. Suttil, J.A., Wasserscheid, P., McGuinness, D.S., Gardinera, M.G., and Evansc, S.J., Catal. Sci. Technol., 2014, vol. 4, no. 8, pp. 2574–2588. https://doi.org/10.1039/C4CY00457D

    Article  CAS  Google Scholar 

  41. Sydora, O.L., Jones, T.C., Small, B.L., Nett, A.J., Fischer, A.A., and Carney, M.J., ACS Catal., 2012, vol. 2, no. 12, pp. 2452–2455. https://doi.org/10.1021/cs300488t

    Article  CAS  Google Scholar 

  42. Sydora, O.L., Brooke, M.K., Small, L., and Hutchison, S., Patent US 10144752 B2, 2018.

  43. Bischof, S.M., Kilgore, U.J., Sydora, O.L., Ess, D.H., Fuller, J.T., and Kwon, D.-H., Patent US 10493442 B2, 2019.

  44. Kwon, D.-H., Maley, S.M., Stanley, J.C., Sydora, O.L., Bischof, S.M., and Ess, D.H., ACS Catal., 2020, vol. 10, no. 17, pp. 9674–9683. https://doi.org/10.1021/acscatal.0c02595

    Article  CAS  Google Scholar 

  45. Kilgore, U.J., Bischof, S.M., and Sydora, O.L., Patent US 11117845 B2, 2021.

  46. Wöhl, A., Müller, W., Peitz, S., Peulecke, N., Aluri, B.R., Müller, B.H., Heller, D., Rosenthal, U., Al-Hazmi, M.H., and Mosa, F.M., Chemistry – A Eur. J., 2010, vol. 16, no. 26, pp. 7833–7842. https://doi.org/10.1002/chem.201000533

    Article  CAS  Google Scholar 

  47. Müller, W., Wöhl, A., Peitz, S., Peulecke, N., Aluri, B.R., Müller, B.H., Heller, D., Rosenthal, U., Al-Hazmi, M.H., and Mosa, F.M., ChemCatChem., 2010, vol. 2, no. 9, pp. 1130–1142. https://doi.org/10.1002/cctc.201000052

    Article  CAS  Google Scholar 

  48. Gunasekara, T., Kim, J., Preston, A., Medvedev, G.A., Delgass, W.N., Sydora, O.L., Caruthers, J.M., and Abu-Omar, M.M., ACS Catal., 2018, vol. 8, no. 8, pp. 6810–6819. https://doi.org/10.1021/acscatal.8b00468

    Article  CAS  Google Scholar 

  49. Wang, X., Shao, H., and Jiang, T., Acta Petrolei Sinica (Petrol. Proc. Sect.), 2022, vol. 38, no. 5, pp. 1102–1111. https://doi.org/10.3969/j.issn.1001-8719.2022.05.011

    Article  CAS  Google Scholar 

  50. Manyik, R.M., Walker, W.E., and Wilson, T., J. Catal., 1977, vol. 47, no. 2, pp. 197–209. https://doi.org/10.1016/0021-9517(77)90167-1

    Article  CAS  Google Scholar 

  51. Yang, Y., Kim, H., Lee, J., Paik, H., and Jang, H.G., Appl. Catal. A: Gen., 2000, vol. 193, nos. 1–2, pp. 29–38. https://doi.org/10.1016/S0926-860X(99)00416-0

    Article  CAS  Google Scholar 

  52. Kuhlmann, S., Dixon, J.T., Haumann, M., Morgan, D.H., Ofili, J., Spuhl, O., Taccardi, N., and Wasserscheid, P., Adv. Synth. Catal., 2006, vol. 348, nos. 10–11, pp. 1200–1206. https://doi.org/10.1002/adsc.200606062

    Article  CAS  Google Scholar 

  53. IHS Chemical. Light linear alpha olefin market study. Special report prospectus. https://cdn.ihs.com/www/pdf/IHS-Chemical-Linear-Alpha-Olefin-SRProspectus.pdf

Download references

Funding

This work was supported by the Ministry of Science and Higher Education of the Russian Federation within governmental order (project AAAA-A19-119041090087-4).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. E. Faingol’d.

Ethics declarations

I.V. Sedov, a co-author, is a deputy editor-in-chief at the Neftekhimiya (Petroleum Chemistry) Journal. The other co-authors declare no conflict of interest requiring disclosure in this article.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Faingol’d, E.E., Lashmanov, N.N., Saratovskikh, S.L. et al. Kinetics of Selective Trimerization of Ethylene to 1-Hexene over Chromium-Based Catalysts. Pet. Chem. 63, 1335–1352 (2023). https://doi.org/10.1134/S0965544123110026

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0965544123110026

Keywords:

Navigation