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.
Notes
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
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
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
Wilke, G., Ang. Chem. Int. Ed., 2003, vol. 42, no. 41, pp. 5000–5008. https://doi.org/10.1002/anie.200330056
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
Matkovskii, P., Irzhak, V., and Mel’nikov, V., Vysokomol. Soed., Ser. A, 1993, vol. 35, no. 2, pp. 207–211.
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
Wass, D.F., Dalton. Trans., 2007, no. 8, pp. 816–819. https://doi.org/10.1039/b616291f
McGuinness, D.S., Chem. Rev., 2011, vol. 111, no. 3, pp. 2321–2341. https://doi.org/10.1021/cr100217q
Agapie, T., Coord. Chem. Rev., 2011, vol. 255, nos. 7–8, pp. 861–880. https://doi.org/10.1016/j.ccr.2010.11.035
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
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
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
Tembe, G., Catal. Rev., 2022, vol. 65, no. 4, pp. 1412–1467. https://doi.org/10.1080/01614940.2021.2014638
Briggs, J.R. and Briggs, J.R., J. Chem. Soc., Chem. Commun., 1989, no. 11, pp. 674. https://doi.org/10.1039/C39890000674
Freeman, J.W., Buster, J.L., and Knudsen, R.D., Patent US 5856257 A, 1999.
Freeman, J.W., Ewert, W.M., Kreischer, B.E., Knudsen, R.D., and Cowan, G.D., Patent US 6455648 B1, 2002.
Keim, W., Ang. Chem. Int. Ed., 1990, vol. 29, no. 3, pp. 235–244. https://doi.org/10.1002/anie.199002351
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
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
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
Sydora, O.L., Patent US 8471085 B2, 2013.
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
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
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
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
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
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.
Araki, Y., Nakamura, H., Nanba, Y., Okano, T., Patent US 5856612 A, 1999.
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
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
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
Wass, D.F., Patent WO 0204119 A1, 2002.
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
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
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
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
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
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
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
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
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
Sydora, O.L., Brooke, M.K., Small, L., and Hutchison, S., Patent US 10144752 B2, 2018.
Bischof, S.M., Kilgore, U.J., Sydora, O.L., Ess, D.H., Fuller, J.T., and Kwon, D.-H., Patent US 10493442 B2, 2019.
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
Kilgore, U.J., Bischof, S.M., and Sydora, O.L., Patent US 11117845 B2, 2021.
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
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
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
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
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
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
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
IHS Chemical. Light linear alpha olefin market study. Special report prospectus. https://cdn.ihs.com/www/pdf/IHS-Chemical-Linear-Alpha-Olefin-SRProspectus.pdf
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This work was supported by the Ministry of Science and Higher Education of the Russian Federation within governmental order (project AAAA-A19-119041090087-4).
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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.
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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
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DOI: https://doi.org/10.1134/S0965544123110026