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Preparation of nickel catalysts bearing Schiff base macrocycles and their performance in ethylene oligomerization

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Abstract

Two Schiff base macrocyclic ligands (L1 and L2) were synthesized using ethylenediamine and terephthalaldehyde (or isophthalaldehyde) as raw materials in acetonitrile solvent. Surprisingly, series of Schiff base macrocyclic ligands with different combination modes (L2-1, L2-2 and L2-3) with isophthalaldehyde as raw material were synthesized. Two Schiff base macrocyclic nickel complexes (Ni-1 and Ni-2) based on L1 and L2 for ethylene oligomerization were obtained with (DME)NiCl2. The synthesized ligands and their corresponding complexes were characterized by various analysis techniques to confirm their chemical structure and thermal stability. And the catalytic properties of the two nickel complexes were also investigated for ethylene oligomerization. When the ethylene pressure was 0.5 MPa, the Al/Ni ratio was 500:1, and the reaction time was 30 min in the presence of MAO, the catalytic activities of Ni-1 and Ni-2 were 4.53 × 104 g/(mol Ni·h) and 4.73 × 104 g/(mol Ni·h), respectively. Compared with PS-Ni complex based on 2,3-butanedione and p-phenylenediamine and three other nickel complexes with simpler ligand structures, Ni-1 and Ni-2 had lower catalytic activities and higher selectivity for C4 olefin because of the higher spatial resistance of the macrocycles.

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The authors declare that all data supporting the findings of this study are available within the article.

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Acknowledgements

This work was supported by the Heilongjiang Scientific Research Foundation for Postdoctoral Settlement of China (Grant No. 16190023) and the Heilongjiang Natural Science Foundation of China (Grant No. E2018012). For the characterization work, we are appreciative of the State Key Lab of Inorganic Synthesis and Preparative Chemistry at Jilin University and Analysis and Test Center of Northeast Petroleum University for the characterization work.

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Authors and Affiliations

  1. Provincial Key Laboratory of Polyolefin New Materials, College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing, 163318, People’s Republic of China

    Jiahui Li, Lijun Guo, Feng Li & Cuiqin Li

  2. Daqing Petrochemical Research Center, CNPC, Daqing, 163318, People’s Republic of China

    Hongliang Huo, Yuru Wang & Yuxin Gao

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  1. Jiahui Li
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JL wrote the main manuscript text and prepared all figures. CL helped to revise the text. All authors reviewed the manuscript.

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Correspondence to Cuiqin Li.

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Li, J., Guo, L., Huo, H. et al. Preparation of nickel catalysts bearing Schiff base macrocycles and their performance in ethylene oligomerization. Transit Met Chem 48, 99–111 (2023). https://doi.org/10.1007/s11243-023-00527-w

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