SpringerLink
Log in

Novel dendrimer-based nickel catalyst: synthesis, characterization and performance in ethylene oligomerization

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

A novel nickel metallodendrimer was synthesized with poly(amidoamine), 3,5-di-tert-butyl-2-hydroxy-benzaldehyde and nickel chloride via the Schiff’s base and the complexation reactions. Structures of the dendritic ligand and its nickel complex were characterized by IR, NMR, UV, ESI-MS and elemental analyses. This new nickel metallodendrimer as a catalyst precursor, together with methylaluminoxane as an activator, was evaluated in the ethylene oligomerization. Under the conditions of 0.5 h, 0.5 MPa, 25°C and Al/Ni mole ratio 500: 1 employed for the nickel complex, the catalytic activity showed a maximum value of 4.93 × 105 grams per mole of Ni catalyst per hour. Substituents on the benzene ring seem to have a negative influence on the catalytic activity of the complex.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Benito, J. M., de Jesús, E., de la Mata, F. J., Flores, J. C., & Gómez, R. (2005). Generation effects on the microstructure and product distribution in ethylene polymerization promoted by dendritic nickel catalysts. Chemical Communication, 41, 5217–5219. DOI: 10.1039/b511379m.

    Article  Google Scholar 

  • Benito, J. M., de Jesús, E., de la Mata, F. J., Flores, J. C., Gómez, R., & Gómez-Sal, P. (2006). Mononuclear and dendritic nickel(II) complexes containing N,N′-iminopyridine chelating ligands: Generation effects on the catalytic oligomerization and polymerization of ethylene. Organometallics, 25, 3876–3887. DOI: 10.1021/om0509084.

    Article  CAS  Google Scholar 

  • Chen, J. X., Huang, Y. B., Li, Z. G., Zhang, Z. C., Wei, C. X., Lan, T. G., & Zhang, W. J. (2006). Syntheses of iron, cobalt, chromium, copper and zinc complexes with bulky bis(imino)pyridyl ligands and their catalytic behaviors in ethylene polymerization and vinyl polymerization of norbornene. Journal of Molecular Catalysis A: Chemical, 259, 133–141. DOI: 10.1016/j.molcata.2006.06.016.

    Article  CAS  Google Scholar 

  • de Souza, C. G., de Souza, R. F., & Bernardo-Gusmão, K. (2007). Effect of alkylaluminum cocatalyst on ethylene polymerization with nickel-α-diimine complex. Applied Catalysis A: General, 325, 87–90. DOI: 10.1016/j.apcata.2007.03.007.

    Article  Google Scholar 

  • Doherty, M. D., Trudeau, S., White, P. S., Morken, J. P., & Brookhart, M. (2007). Ethylene oligomerization catalyzed by a unique phosphine-oxazoline palladium(II) complex. Propagation and chain transfer mechanisms. Organometallics, 26, 1261–1269. DOI: 10.1021/om061025v.

    CAS  Google Scholar 

  • Issberner, J., Moors, R., & Vögtle, F. (1995). Dendrimers: From generations and functional groups to functions. Angewandte Chemie International Edition, 33, 2413–2420. DOI: 10.1002/anie.199424131.

    Article  Google Scholar 

  • Malgas, R., Mapolie, S. F., Ojwach, S. O., Smith, G. S., & Darkwa, J. (2008). The application of novel dendritic nickel catalysts in the oligomerization of ethylene. Catalysis Communications, 9, 1612–1617. DOI: 10.1016/j.catcom.2008.01.009.

    Article  CAS  Google Scholar 

  • Malgas-Enus, R., Mapolie, S. F., & Smith, G. S. (2008). Norbornene polymerization using multinuclear nickel catalysts based on a polypropyleneimine dendrimer scaffold. Journal of Organometallic Chemistry, 693, 2279–2286. DOI: 10.1016/j.jorganchem.2008.03.029.

    Article  CAS  Google Scholar 

  • Malgas-Enus, R., & Mapolie, S. F. (2012). A novel nickel(II) complex based on a cyclam-cored generation-one dendrimeric salicylaldimine ligand and its application as a catalyst precursor in norbornene polymerization: Comparative study with some other first generation DAB-polypropyleneimine metallodendrimers. Polyhedron, 47, 87–93. DOI: 10.1016/j.poly.2012.08.015.

    Article  CAS  Google Scholar 

  • Malgas-Enus, R., & Mapolie, S. F. (2014). Nickel metallodendrimers as catalyst precursors in the tandem oligomerization of ethylene and Friedel-Crafts alkylation of its olefinic products. Inorganica Chimica Acta, 409, 96–105. DOI: 10.1016/j.ica.2013.06.016.

    Article  CAS  Google Scholar 

  • McGuinness, D. S., Rucklidge, A. J., Tooze, R. P., & Slawin, A. M. Z. (2007). Cocatalyst influence in selective oligomerization: Effect on activity, catalyst stability, and 1-hexene/1-octene selectivity in the ethylene trimerization and tetramerization reaction. Organometallics, 26, 2561–2569. DOI: 10.1021/om070029c.

    Article  CAS  Google Scholar 

  • Mezzenga, R., Boogh, L., & Månson, J. A. E. (2001). A review of dendritic hyperbranched polymer as modifiers in epoxy composites. Composites Science and Technology, 61, 787–795. DOI: 10.1016/s0266-3538(01)00022-7.

    Article  CAS  Google Scholar 

  • Mogorosi, M. M., Mahamo, T., Moss, J. R., Mapolie, S. F., Slootweg, J. C., Lammertsma, K., & Smith, G. S. (2011). Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and catalytic oligomerisation of ethylene. Journal of Organometallic Chemistry, 696, 3585–3592. DOI: 10.1016/j.jorganchem.2011.07.042.

    Article  CAS  Google Scholar 

  • Müller, C., Ackerman, L. J., Reek, J. N. H., Kamer, P. C. J., & van Leeuwen, P. W. N. M. (2004). Site-isolation effects in a dendritic nickel catalyst for the oligomerization of ethylene. Journal of the American Chemical Society, 126, 14960–14963. DOI: 10.1021/ja046901f.

    Article  Google Scholar 

  • Newkome, G. R., Yao, Z. Q., Baker, G. R., Gupta, V. K., Russo, P. S., & Saunders, M. J. (1986). Chemistry of micelles series. Part 2. Cascade molecules. Synthesis and characterization of a benzene[9]3-arborol. Journal of the American Chemical Society, 108, 849–850. DOI: 10.1021/ja00264a054.

    Article  CAS  Google Scholar 

  • Ning, Y. C. (2005). Structural identification of organic compounds and organic spectroscopy. Weinheim, Germany: Wiley-VCH.

    Google Scholar 

  • Ojwach, S. O., Guzei, I. A., Benade, L. L., Mapolie, S. F., & Darkwa, J. (2009). (Pyrazol-1-ylmethyl)pyridine nickel complexes: Ethylene oligomerization and unusual Friedel-Crafts alkylation catalysts. Organometallics, 28, 2127–2133. DOI: 10.1021/om8006322.

    Article  CAS  Google Scholar 

  • Peitz, S., Aluri, B. R., Peulecke, N., Müller, B. H., Wöhl, A., Müller, W., Al-Hamzi, M. H., Mosa, F. M., & Rosenthal, U. (2010). An alternative mechanistic concept for homogeneous selective ethylene oligomerization of chromium-based catalysts: binuclear metallacycles as a reason for 1-octene selectivity? Chemistry — A European Journal, 16, 7670–7676. DOI: 10.1002/chem.201000750.

    Article  CAS  Google Scholar 

  • Smith, G., Chen, R., & Mapolie, S. (2003). The synthesis and catalytic activity of a first-generation poly(propylene imine) pyridylimine palladium metallodendrimer. Journal of Organometallic Chemistry, 673, 111–115. DOI: 10.1016/s0022-328x(03)00173-6.

    Article  CAS  Google Scholar 

  • Svenson, S., & Tomalia, D. A. (2005). Dendrimers in biomedical applications-reflections on the field. Advanced Drug Delivery Reviews, 57, 2106–2129. DOI: 10.1016/j.addr.2005.09.018.

    Article  CAS  Google Scholar 

  • van Koten, G., & Jastrzebski, J. T. B. H. (1999). Peripheryfunctionalized organometallic dendrimers for homogeneous catalysis. Journal of Molecular Catalysis A: Chemical, 146, 317–323. DOI: 10.1016/s1381-1169(99)00091-6.

    Article  Google Scholar 

  • Wang, J., Zhang, P., Chen, S., Li, C. Q., Li, H. Y., & Yang, G. (2013). The preparation of dendritic nickel complex and performance evaluation in the oligomerization of ethylene. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 50, 163–167. DOI: 10.1080/10601325.2013.741486.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Oil Gas & Chemical Technology, College of Chemistry & Chemical Engineering, Northeast Petroleum University, Daqing, China

    Jun Wang, Guang Yang, Cui-Qin Li & Wei-Guang Shi

  2. Daqing Petrochemical Research Center Daqing, 163318, Heilongjiang Province, China

    Si-Han Wang

Authors
  1. Jun Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Guang Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Cui-Qin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wei-Guang Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Si-Han Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jun Wang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, J., Yang, G., Li, CQ. et al. Novel dendrimer-based nickel catalyst: synthesis, characterization and performance in ethylene oligomerization. Chem. Pap. 68, 1532–1538 (2014). https://doi.org/10.2478/s11696-014-0603-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-014-0603-1

Keywords

Search

Navigation