Abstract
A novel star iminopyridyl ligand was synthesized in modest yield with 1.0 G star macromolecule and pyridine-2-carboxaldehyde as the raw materials. Reactions of the star iminopyridyl ligand with Fe(II), Co(II) and Ni(II) salts afforded metal complexes (Cat-Fe, Cat-Co and Cat-Ni) in good yields. The compounds were characterized by FT-IR, 1H NMR, 13C NMR, UV–Vis, ESI–MS and ICP-MS. In the presence of methylalumoxane (MAO), the iron, cobalt and nickel complexes have demonstrated higher ethylene oligomerization activity (up to 4.28 × 105 g/(mol Co h)), affording C4 as the major product as well as C6, C8 and C10-18 oligomers. The catalytic activity was quite sensitive to the kind of species. The nature of solvent and co-catalyst significantly affected both the catalytic activity and product distribution. Moreover, the effect of oligomerization parameters (reaction temperature, [Al]/[Co] molar ratio, ethylene pressure) on the catalytic activity and the product distribution was investigated.
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References
Alferov KA, Belov GP, Meng Y (2017) Chromium catalysts for selective ethylene oligomerization to 1-hexene and 1-octene: recent results. Appl Catal A Gen 542:71–124
Agapie T (2011) Selective ethylene oligomerization: recent advances in chromium catalysis and mechanistic investigations. Coordin Chem Rev 255:861–880
Lee H, Joe Y, Park H (2019) Chromium catalysts for ethylene trimerization/tetramerization functionalized with ortho-fluorinated arylphosphine ligand. Catal Commun 121:15–18
Jayamani A, Nyamato GS, Ojwach SO (2019) Ethylene oligomerization reactions catalyzed by homogeneous and silica immobilized N^O Fe(II) and Co(II) complexes. J Organomet Chem 903:1–8
Vogt D, Cornils B, Herrmann WA (1996) Applied homogeneous with organometallic compounds. VCH New York 1:245–258
Leeuwen PWNMV, Clément ND, Tschan MJL (2011) New processes for the selective production of 1-octene. Coord Chem Rev 255:1499–1517
Haghverdi M, Tadjarodi A, Bahri-Laleh N et al (2018) Preparation, characterization, DFT calculations and ethylene oligomerization studies of iron(II) complexes bearing 2-(1H-benzimidazol-2-yl)-phenol derivatives. J coord Chem 71:1180–1192
Rodríguez B, Cortés-Arriagada D, Sánchez-Rodríguez EP et al (2018) B(C6F5)3 promotes the catalytic activation of [N, S]-ferrocenyl nickel complexes in ethylene oligomerization. Appl Catal A Gen 550:228–235
Nyamato GS, Alam MG, Ojwach SO (2016) Nickel(II) complexes bearing pyrazolylpyridines: synthesis, structures and ethylene oligomerization reactions. Appl Organometal Chem 30:89–94
Zhang J, Liu SF, Li A et al (2016) Nickel (II) complexes chelated by 2,6-pyridinedicarboxamide: syntheses, characterization, and ethylene oligomerization. New J Chem 40:7027–7033
Wang Z, Solan GA, Zhang WJ et al (2018) Carbocyclic-fused N, N, N-pincer ligands as ring-strain adjustable supports for iron and cobalt catalysts in ethylene oligo-/polymerization. Coordin Chem Rev 363:92–108
Arrozi USF, Bon V, Kutzscher C et al (2019) Towards highly active and stable nickel-based metal–organic frameworks as ethylene oligomerization catalysts. Dalton Trans 8:3415–3421
Suo HY, Solan GA, Ma YP et al (2017) Developments in compartmentalized bimetallic transition metal ethylene polymerization catalysts. Coordin Chem Rev 68:903–909
Wang SL, Sun WH, Redshaw C (2014) Recent progress on nickel-based systems for ethylene oligo-/polymerization catalysis. J Organomet Chem 751:717–741
Ma J, Feng C, Wang SL et al (2014) Bi- and tri-dentate imino-based iron and cobalt pre-catalysts for ethylene oligo-/polymerization. Inorg Chem Front 1:14–34
Adewuyi S, Li G, Zhang S et al (2007) Nickel(II) complexes chelated by 2-quinoxalinyl-6-iminopyridines: synthesis, crystal structures and ethylene oligomerization. J Organomet Chem 692:3532–3541
Sun WH, Hao P, Li G et al (2007) Synthesis and characterization of iron and cobalt dichloride bearing 2-quinoxalinyl-6-iminopyridines and their catalytic behavior toward ethylene reactivity. J Organomet Chem 692:4506–4518
Chen YJ, Du SZ, Huang CB et al (2017) Balancing high thermal stability with high activity in diaryliminoacenaphthene-nickel(II) catalysts for ethylene polymerization. J Polym Sci Part A Polym Chem 55:1971–1983
Wei W, Yu BW, Alam F et al (2019) Ethylene oligomerization promoted by nickel-based catalysts with silicon-bridged diphosphine amine ligands. Transit Metal Chem 44:125–133
Tuskaev VA, Zubkevich SV, Saracheno D et al (2019) Nickel(II) complexes with tripodal NNN ligands as homogenous and supported catalysts for ethylene oligomerization. Mol Catal 464:29–38
Soficheva OS, Bekmukhamedov GE, Dobrynin AB et al (2019) α-Diphenylphosphino-N-(pyrazin-2-yl) glycine as a ligand in Ni-catalyzed ethylene oligomerization. Mendeleev Commun 29:575–577
Ahamad T, Alshehri LSM (2014) Synthesis and characterization of first- and second-generation polyamide pyridylimine nickel dihalide metallodendrimers and their uses as catalysts for ethylene polymerization. Polym Int 63:1965–1973
Martinez-olid F, Jesus ED, Flores JC (2014) Monometallic nickel(II) complexes containing N, N′-iminopyridine chelating ligands with dendritic substituents: the influence of dendrimer topology on the catalytic oligomerization and polymerization of ethylene. Inorg Chim Acta 409:156–162
Malgas R, Mapolie SF, Ojwach SO et al (2008) The application of novel dendritic nickel catalysts in the oligomerization of ethylene. Afr J Biotechnol 9:1612–1617
Wang J, Yang G, Li CQ et al (2014) Novel dendrimer-based nickel catalyst: synthesis, characterization and performance in ethylene oligomerization. Chem Pap 68:1532–1538
Wang J, Zhang N, Li CQ et al (2016) Nickel complexes based on hyperbranched salicylaldimine ligands:synthesis, characterization, and catalytic properties for ethylene oligomerization. J Organomet Chem 822:104–111
Wang J, Li HY, Song L et al (2016) Cobalt complexes based on dendritic PAMAM bridged salicylaldimine ligands: Synthesis, characterization and performance in ethylene oligomerization. J Macromol Sci A 53:709–715
Wang J, Zhang N, Shi WG et al (2017) Hyperbranched bisphosphinoamine ligands: synthesis, characterization and application in ethylene oligomerization. J Coord Chem 70:2708–2721
Zhang N, Wang JM, Huo HL et al (2018) Iron, cobalt and nickel complexes bearing hyperbranched iminopyridyl ligands: Synthesis, characterization and evaluation as ethylene oligomerization catalysts. Inorg Chim Acta 469:209–216
Wang J, Liu JY, Lan TY et al (2019) Selective ethylene oligomerization bearing hyperbranched bispyridylamine chromium catalyst. J Coord Chem 72:814–825
Wang J, Li CQ, Zhang SY et al (2008) Synthesis and characterization of lower generation broom molecules. Chin Chem Lett 19:43–46
Antonov AA, Semikolenova NV, Talsi EP et al (2019) Catalytic ethylene oligomerization on cobalt(II) bis(imino)pyridine complexes bearing electron-withdrawing groups. J Organomet Chem 884:55–58
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We acknowledge the funding from the Heilongjiang Provincial Postdoctoral Science Foundation (16190016) and Youth Science Foundation of Northeast Petroleum University (2018QNL-13).
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Zhang, N., Wu, Y., Li, Y. et al. Star iminopyridyl iron, cobalt and nickel complexes: synthesis, molecular structures, and evaluation as ethylene oligomerization catalysts. Polym. Bull. 79, 4219–4231 (2022). https://doi.org/10.1007/s00289-021-03697-8
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DOI: https://doi.org/10.1007/s00289-021-03697-8