REVIEWS

Applications of Cobalt Complexes in Olefin Polymerization

  • Lianrong Fu ,
  • Yan-Bing Wang ,
  • Hui Jiang ,
  • Xin-Qi Hao ,
  • Mao-Ping Song
Expand
  • College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received date: 2022-04-14

  Revised date: 2022-07-30

  Online published: 2022-08-18

Supported by

National Natural Science Foundation of China(21803059); National Natural Science Foundation of China(U1904212); National Natural Science Foundation of China(U2004191); Natural Science Foundation of Henan Province(202300410477); Natural Science Foundation of Henan Province(222300420294); China Postdoctoral Science Foundation(2020M-672260)

Abstract

Polyolefin materials have huge annual output and wide applications, which are closely related to human production and life closely. The core of polyolefin research lies in the catalyst, the performance of which often determines the properties of polyolefins. Therefore, the design and synthesis of high-performance catalyst have become a hot research topic, and a large number of catalysts have come out. Cobalt complexes are very important kind of olefin polymerization catalysts, which can be used to catalyze a variety of monomer polymerization. These cobalt complexes are structure diversity and have a variety of coordination atoms (such as, N, O, P, S etc.), and the synthesis is relatively simple. Therefore, the structure of the catalyst can be precisely regulated to improve the catalytic activity, adjust the microstructure of the polymer, and improve the macroscopical properties of the polymer. In this paper, the applications of cobalt complexes in homopolymerization of ethylene, conjugated dienes, norbornene, acrylates and other common monomers are reviewed, and the cobalt complexes are classified from the perspective of structure. What’s more, the effects of catalyst structure, temperature, cocatalyst on catalyst activity, polymer molecular weight and polymer microstructure are discussed in detail. It is expected to provide a reference for the design and synthesis of cobalt complexes in the future.

Cite this article

Lianrong Fu , Yan-Bing Wang , Hui Jiang , Xin-Qi Hao , Mao-Ping Song . Applications of Cobalt Complexes in Olefin Polymerization[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3530 -3548 . DOI: 10.6023/cjoc202204036

References

[1]
Sturzel, M.; Mihan, S.; Mulhaupt, R. Chem. Rev. 2016, 116, 1398.
[2]
Bahuleyan, B. K.; Ahn, I. Y.; Appukuttan, V.; Lee, S. H.; Ha, C.-S.; Kim, I.; Suh, H. Macromol. Res. 2010, 18, 701.
[3]
Horne, S. E.; Kiehl, J. P.; Shipman, J. J.; Folt, V. L.; Gibbs, C. F.; Willson, E. A.; Newton, E. B.; Reinhart, M. A. Ind. Eng. Chem. 1956, 48, 784.
[4]
Ricci, G.; Sommazzi, A.; Masi, F.; Ricci, M.; Boglia, A.; Leone, G. Coord. Chem. Rev. 2010, 254, 661.
[5]
Wang, B.; Cui, D.; Lv, K. Macromolecules 2008, 41, 1983.
[6]
Natta, G.; Pino, P.; Corradini, P.; Danusso, F.; Mantica, E.; Mazzanti, G.; Moraglio, G. J. Am. Chem. Soc. 1955, 77, 1708.
[7]
Coates, G. W. Dalton Trans. 2002, 467.
[8]
Redshaw, C.; Tang, Y. Chem. Soc. Rev. 2012, 41, 4484.
[9]
Tan, C.; Chen, C. Angew. Chem., Int. Ed. 2019, 58, 7192.
[10]
Wang, F.; Chen, C. Polym. Chem. 2019, 10, 2354.
[11]
Tan, C.; Chen, C. Sci. Bull. 2020, 65, 1137.
[12]
Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283.
[13]
Britovsek, G. J. P.; Bruce, M.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J.; Redshaw, C.; Solan, G. A.; Str?mberg, S.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 8728.
[14]
Wang, Z.; Solan, G. A.; Zhang, W. J.; Sun, W.-H. Coord. Chem. Rev. 2018, 363, 92.
[15]
Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443.
[16]
Daugulis, O.; Brookhart, M.; White, P. S. Organometallics 2003, 22, 4699.
[17]
Hyatt, M. G.; Guironnet, D. Organometallics 2019, 38, 788.
[18]
Zhao, Y.; Jung, J.; Nozaki, K. J. Am. Chem. Soc. 2021, 143, 18832.
[19]
Laine, T. V.; Klinga, M.; Maaninen, A.; Aitola, E.; Leskela, M. Acta Chem. Scand. 1999, 53, 968.
[20]
Rosa, V.; Carabineiro, S. A.; Avilés, T.; Gomes, P. T.; Welter, R.; Campos, J. M.; Ribeiro, M. R. J. Organomet. Chem. 2008, 693, 769.
[21]
Bianchini, C.; Mantovani, G.; Meli, A.; Migliacci, F.; Laschi, F. Organometallics 2003, 22, 2545.
[22]
Sun, W.-H.; Tang, X. B.; Gao, T. L.; Wu, B.; Zhang, W. J.; Ma, H. W. Organometallics 2004, 23, 5037.
[23]
Xiao, T. P. F.; Lai, J. J.; Zhang, S.; Hao, X.; Sun, W.-H. Catal. Sci. Technol. 2011, 1, 462.
[24]
Song, S. J.; Zhao, W. Z.; Wang, L.; Redshaw, C.; Wang, F. S.; Sun, W.-H. J. Organomet. Chem. 2011, 696, 3029.
[25]
Xiao, T. P. F.; Hao, P.; Kehr, G.; Hao, X.; Erker, G.; Sun, W.-H. Organometallics 2011, 30, 4847.
[26]
Song, S. J.; Xiao, T. P. F.; Redshaw, C.; Hao, X.; Wang, F. S.; Sun, W.-H. J. Organomet. Chem. 2011, 696, 2594.
[27]
Wang, M.; Yu, X. M.; Shi, Z.; Qian, M. X.; Jin, K.; Chen, J. H.; He, R. J. Organomet. Chem. 2002, 645, 127.
[28]
Wang, L.; Zhang, C.; Wang, Z.-X. Eur. J. Inorg. Chem. 2007, 2477.
[29]
Sun, W.-H.; Hao, P.; Zhang, S.; Shi, Q.; Zuo, W.; Tang, X.; Lu, X. Organometallics 2007, 26, 2720.
[30]
Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
[31]
Takeuchi, D. In Organometallic Reactions and Polymerization, Eds.: Osakada, K., Springer Berlin Heidelberg, Berlin, 2014, pp. 119-167.
[32]
Flisak, Z.; Sun, W.-H. ACS Catal. 2015, 5, 4713.
[33]
Sun, W.-H.; Hao, P.; Li, G.; Zhang, S.; Wang, W. Q.; Yi, J. J.; Asma, M.; Tang, N. J. Organomet. Chem. 2007, 692, 4506.
[34]
Gao, R.; Wang, K. F.; Li, Y.; Wang, F. S.; Sun, W.-H.; Redshaw, C.; Bochmann, M. J. Mol. Catal. A: Chem. 2009, 309, 166.
[35]
Yu, J.; Huang, W.; Wang, L.; Redshaw, C.; Sun, W.-H. Dalton Trans. 2011, 40, 10209.
[36]
He, F.; Zhao, W.; Cao, X.-P.; Liang, T.; Redshaw, C.; Sun, W.-H. J. Organomet. Chem. 2012, 713, 209.
[37]
Mahmood, Q.; Ma, Y.; Hao, X.; Sun, W.-H. Appl. Organomet. Chem. 2019, 33, 4857.
[38]
Yan, Y.; Yuan, S.-F.; Liu, M.; Solan, G. A.; Ma, Y.-P.; Liang, T.-L.; Sun, W.-H. Chin. J. Polym. Sci. 2022, 40, 266.
[39]
Wang, S. L.; Zhao, W. Z.; Hao, X.; Li, B. X.; Redshaw, C.; Li, Y. S.; Sun, W. -H. J. Organomet. Chem. 2013, 731, 78.
[40]
Han, M.; Oleynik, I. I.; Liu, M.; Ma, Y.; Oleynik, I. V.; Solan, G. A.; Liang, T.; Sun, W. -H. Appl. Organomet. Chem. 2021, 36, 6529.
[41]
Liu, J.-Y.; Zheng, Y.; Hu, N.-H.; Li, Y.-S. Chin. J. Chem. 2006, 24, 1447.
[42]
Antonov, A. A.; Semikolenova, N. V.; Talsi, E. P.; Bryliakov, K. P. J. Organomet. Chem. 2019, 884, 55.
[43]
Wang, L.; Sun, W.-H.; Han, L.; Yang, H.; Hu, Y.; Jin, X. J. Organomet. Chem. 2002, 658, 62.
[44]
Jie, S. Y..; Zhang, S.; Wedeking, K.; Zhang, W.; Ma, H. W.; Lu, X. M.; Deng, Y.; Sun, W.-H. C. R. Chim. 2006, 9, 1500.
[45]
Pelletier, J. D. A.; Champouret, Y. D. M.; Cadarso, J.; Clowes, L.; Ga?ete, M.; Singh, K.; Thanarajasingham, V.; Solan, G. A. J. Organomet. Chem. 2006, 691, 4114.
[46]
Jie, S.; Zhang, S.; Sun, W. -H. Eur. J. Inorg. Chem. 2007, 5584.
[47]
Zhang, M.; Hao, P.; Zuo, W. W.; Jie, S. Y.; Sun, W.-H. J. Organomet. Chem. 2008, 693, 483.
[48]
Zhang, M.; Gao, R.; Hao, X.; Sun, W.-H. J. Organomet. Chem. 2008, 693, 3867.
[49]
Wang, K.; Wedeking, K.; Zuo, W.; Zhang, D.; Sun, W.-H. J. Organomet. Chem. 2008, 693, 1073.
[50]
Zhang, S.; Sun, W.-H.; Xiao, T. P.; Hao, X. Organometallics 2010, 29, 1168.
[51]
Appukuttan, V. K.; Liu, Y.; Son, B. C.; Ha, C. S.; Suh, H.; Kim, I. Organometallics 2011, 30, 2285.
[52]
Sun, W.-H.; Kong, S. L.; Chai, W. B.; Shiono, T.; Redshaw, C.; Hu, X. Q.; Guo, C. Y.; Hao, X. Appl. Catal. A Gen 2012, 447, 67.
[53]
Ba, J. J.; Du, S. Z.; Yue, E. L.; Hu, X. Q.; Flisak, Z.; Sun, W.-H. RSC Adv. 2015, 5, 32720.
[54]
Huang, F.; Zhang, W.; Yue, E.; Liang, T.; Hu, X.; Sun, W.-H. Dalton Trans. 2016, 45, 657.
[55]
Zhang, R.; Huang, Y.; Solan, G. A.; Zhang, W.; Hu, X.; Hao, X.; Sun, W.-H. Dalton Trans. 2019, 48, 8175.
[56]
Han, M.; Zuo, Z.; Ma, Y.; Solan, G. A.; Hu, X.; Liang, T.; Sun, W.-H. RSC Adv. 2021, 11, 39869.
[57]
Han, M.; Zhang, Q.; Oleynik, II; Suo, H.; Solan, G. A.; Oleynik, I. V.; Ma, Y.; Liang, T.; Sun, W.-H. Dalton Trans. 2020, 49, 4774.
[58]
Suo, H.; Oleynik, I. V.; Oleynik, I. I.; Solan, G. A.; Ma, Y.; Liang, T.; Sun, W.-H. Polymer 2021, 213, 123294.
[59]
Zhang, R.; Oleynik, I. V.; Li, J.; Solan, G. A.; Ma, Y.; Jin, L.; Oleynik, I. I.; Hu, X.; Sun, W.-H. Eur. J. Inorg. Chem. 2021, 3956.
[60]
Zuo, Z.; Han, M.; Ma, Y.; Solan, G. A.; Hu, X.; Liang, T.; Sun, W. H. Appl. Organomet. Chem. 2021, 36, 6500.
[61]
Zada, M.; Guo, L.; Zhang, W.; Ma, Y.; Liang, T.; Sun, W.-H. Eur. J. Inorg. Chem. 2021, 720.
[62]
Han, M.; Oleynik, I. I.; Ma, Y.; Oleynik, I. V.; Solan, G. A.; Liang, T.; Sun, W.-H. Appl. Organomet. Chem. 2021, 35, 6429
[63]
Karam, A.; Tenia, R.; Martinez, M.; Lopez-Linares, F.; Albano, C.; Diaz-Barrios, A.; Sanchez, Y.; Catari, E.; Casas, E.; Pekerar, S.; Albornoz, A. J. Mol. Catal. A: Chem. 2007, 265, 127.
[64]
Abbo, H. S.; Titinchi, S. J. J. Catal. Lett. 2010, 139, 90.
[65]
Ngcobo, M.; Nyamato, G. S.; Ojwach, S. O. Mol. Catal. 2019, 478, 110590.
[66]
Champouret, Y.; Hashmi, O. H.; Visseaux, M. Coord. Chem. Rev. 2019, 390, 127.
[67]
Takeuchi, M.; Shiono, T.; Soga, K. Polym. Int. 1992, 29, 209.
[68]
Ricci, G.; Forni, A.; Boglia, A.; Motta, T.; Zannoni, G.; Canetti, M.; Bertini, F. Macromolecules 2005, 38, 1064.
[69]
Ricci, G.; Leone, G.; Boglia, A.; Boccia, A. C.; Zetta, L. Macromolecules 2009, 42, 9263.
[70]
Ricci, G.; Leone, G.; Pierro, I.; Zanchin, G.; Forni, A. Molecules 2019, 24, 2308.
[71]
Ricci, G.; Leone, G.; Zanchin, G.; Palucci, B.; Forni, A.; Sommazzi, A.; Masi, F.; Zacchini, S.; Guelfi, M.; Pampaloni, G. Molecules 2021, 26, 4067.
[72]
Liu, H.; Wang, F.; Jia, X. Y.; Liu, L.; Bi, J. F.; Zhang, C. Y.; Zhao, L. P.; Bai, C. X.; Hu, Y. M.; Zhang, X. Q. J. Mol. Catal. A: Chem. 2014, 391, 25.
[73]
Dai, Q.; Jia, X.; Yang, F.; Bai, C.; Hu, Y.; Zhang, X. Polymers 2016, 8, 12.
[74]
Guo, L.; Jing, X.; Xiong, S.; Liu, W.; Liu, Y.; Liu, Z.; Chen, C. Polymers 2016, 8, 389.
[75]
Zhu, G.; Zhang, X.; Zhao, M.; Wang, L.; Jing, C.; Wang, P.; Wang, X.; Wang, Q. Polymers 2018, 10, 934.
[76]
Wang, X.; Fan, L.; Huang, C.; Liang, T.; Guo, C.-Y.; Sun, W.-H. J. Polym. Sci. Part A: Polym. Chem. 2016, 54, 3609.
[77]
Alnajrani, M. N.; Mair, F. S. Dalton Trans. 2016, 45, 10435.
[78]
Fang, L.; Zhao, W. P.; Han, C.; Liu, H.; Hu, Y. M.; Zhang, X. Q. Eur. J. Inorg. Chem. 2019, 609.
[79]
Zhang, X. H.; Zhu, G. Q.; Mahmood, Q.; Zhao, M. M.; Wang, L.; Jing, C. Y.; Wang, X. W.; Wang, Q. G. J. Polym. Sci. Part A: Polym. Chem. 2019, 57, 767.
[80]
Lin, W. H.; Zhang, L. P.; Suo, H. Y.; Vignesh, A.; Yousuf, N.; Hao, X.; Sun, W.-H. New J. Chem. 2020, 44, 8076.
[81]
Liu, L.; Wang, F.; Zhang, C.; Liu, H.; Wu, G.; Zhang, X. Mol. Catal. 2022, 517, 112044.
[82]
Kim, J. S.; Ha, C.-S.; Kim, I. e-Polymers 2006.
[83]
Appukuttan, V.; Zhang, L.; Ha, C. S.; Kim, I. Polymer 2009, 50, 1150.
[84]
Appukuttan, V.; Zhang, L.; Ha, J. Y.; Chandran, D.; Bahuleyan, B. K.; Ha, C. S.; Kim, I. J. Mol. Catal. A: Chem. 2010, 325, 84.
[85]
Cariou, R.; Chirinos, J. J.; Gibson, V. C.; Jacobsen, G.; Tomov, A. K.; Britovsek, G. J.; White, A. J. Dalton Trans. 2010, 39, 9039.
[86]
Gong, D.; Jia, X. Y.; Wang, B. L.; Zhang, X. Q.; Jiang, L. S. J. Organomet. Chem. 2012, 702, 10.
[87]
Nobbs, J. D.; Tomov, A. K.; Cariou, R.; Gibson, V. C.; White, A. J.; Britovsek, G. J. Dalton Trans. 2012, 41, 5949.
[88]
Gong, D.; Jia, W. G.; Chen, T.; Huang, K. W. Appl. Catal. A Gen. 2013, 464, 35.
[89]
Gong, D.; Liu, W.; Pan, W.; Chen, T.; Jia, X.; Huang, K.-W.; Zhang, X. J. Mol. Catal. A: Chem. 2015, 406, 78.
[90]
He, A.; Wang, G.; Zhao, W.; Jiang, X.; Yao, W.; Sun, W.-H. Polym. Int. 2013, 62, 1758.
[91]
Alnajrani, M. N.; Mair, F. S. RSC Adv. 2015, 5, 46372.
[92]
Liu, W.; Pan, W. J.; Wang, P.; Li, W.; Mu, J. S.; Weng, G. S.; Jia, X. Y.; Gong, D.; Huang, K. W. Inorg. Chim. Acta 2015, 436, 132.
[93]
Chen, H.; Pan, W.; Huang, K.-W.; Zhang, X.; Gong, D. Polym. Chem. 2017, 8, 1805.
[94]
Zhao, J.; Chen, H.; Li, W.; Jia, X.; Zhang, X.; Gong, D. Inorg. Chem. 2018, 57, 4088.
[95]
Gong, D.; Ying, W. L.; Zhao, J. Y.; Li, W. X.; Xu, Y. C.; Luo, Y. J.; Zhang, X. Q.; Capacchione, C.; Grassi, A. J. Catal. 2019, 377, 367.
[96]
Endo, K.; Kitagawa, T.; Nakatani, K. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 4088.
[97]
Gong, D.; Wang, B. L.; Jia, X. Y.; Zhang, X. Q. Dalton Trans. 2014, 43, 4169.
[98]
Chen, L.; Ai, P. F.; Gu, J. M.; Jie, S. Y.; Li, B. G. J. Organomet. Chem. 2012, 716, 55.
[99]
Ai, P. F.; Chen, L.; Guo, Y. T.; Jie, S. Y.; Li, B. G. J. Organomet. Chem. 2012, 705, 51.
[100]
Yang, D.; Gan, Q.; Chen, H.; Ying, W.; Zhao, J.; Jia, X.; Gong, D. Inorg. Chim. Acta 2019, 496, 119046.
[101]
Alt, F. P.; Heitz, W. Macromol. Chem. Phys. 1998, 199, 1951.
[102]
Pelascini, F.; Peruch, F.; Lutz, P. J.; Wesolek, M.; Kress, J. Macromol. Rapid Commun. 2003, 24, 768.
[103]
Pelascini, F.; Peruch, F.; Lutz, P. J.; Wesolek, M.; Kress, J. Y. Macromol. Symp. 2004, 213, 265.
[104]
Sato, Y.; Nakayama, Y.; Yasuda, H. J. Organomet. Chem. 2004, 689, 744.
[105]
Bao, F.; Lü, X.; Qiao, Y.; Gui, G.; Gao, H.; Wu, Q. Appl. Organomet. Chem. 2005, 19, 957.
[106]
Zhang, D.; Yue, Q.; Wang, J. Y.; Shigeng, G. W.; Weng, L. H. Inorg. Chem. Commun. 2009, 12, 1193.
[107]
Benade, L. L.; Ojwach, S. O.; Obuah, C.; Guzei, I. A.; Darkwa, J. Polyhedron 2011, 30, 2878.
[108]
Bahuleyan, B. K.; Chandran, D.; Kwak, C. H.; Ha, C.-S.; Kim, I. Macromol. Res. 2008, 16, 745.
[109]
Abu-Surrah, A. S.; Ibrahim, K. A.; Abdel-Halim, H. M. Transition Met. Chem. 2009, 34, 803.
[110]
Abu-Surrah, A. S.; Al-Degs, Y. S. J. Appl. Polym. Sci. 2010, 117, 2316.
[111]
Jia, X. Y.; Li, W. X.; Zhao, J. Y.; Yi, F. Y.; Luo, Y. J.; Gong, D. Organometallics 2019, 38, 278.
[112]
Park, S.; Lee, J.; Lee, H.; Jeong, A. R.; Min, K. S.; Nayab, S. Appl. Organomet. Chem. 2019, 33. 4766.
[113]
Lee, J.; Kim, K.; Lee, H.; Nayab, S. Polyhedron 2021, 196, 115003.
[114]
Kim, I.; Hwang, J.-M.; Lee, J. K.; Ha, C. S.; Woo, S. I. Macromol. Rapid Commun. 2003, 24, 508.
[115]
Yliheikkila, K.; Lappalainen, K.; Castro, P. M.; Ibrahim, K.; Abu-Surrah, A.; Leskela, M.; Repo, T. Eur. Polym. J. 2006, 42, 92.
[116]
Yang, M.; Park, W. J.; Yoon, K. B.; Jeong, J. H.; Lee, H. Inorg. Chem. Commun. 2011, 14, 189.
[117]
Ahn, S. H.; Choi, S. I.; Jung, M. J.; Nayab, S.; Lee, H. J. Mol. Struct. 2016, 1113, 24.
Outlines

/