Ethylene oligomerization promoted by nickel-based catalysts with silicon-bridged diphosphine amine ligands

Abstract

A series of nickel complexes [Ni(L1)Br2] (C1), [Ni(L2)Br2] (C2) and [Ni(L3)Br2] (C3) (L1 = N-isopropyl-N-(((diphenylphosphanyl)methyl)dimethylsilyl)-1,1-diphenylphosphanamine, L2 = N-cyclopentyl-N-(((diphenylphosphanyl)methyl)dimethylsilyl)-1,1-diphenylphosphanamine, L3 = N-(2,6-diisopropylphenyl)-N-(((diphenylphosphanyl)methyl)dimethylsilyl)-1,1-diphenylphosphanamine) were synthesized and characterized by elemental analysis, mass spectrometry, spectroscopy and single-crystal X-ray diffraction. L1, L2 and L3 each act as bidentate ligands. Upon activation with ethylaluminum dichloride, these complexes produce efficient catalytic systems for selective dimerization of ethylene to 1-butene, with catalytic activities of 3.45 × 107 g/(molNi·h) and 95.6% butene selectivity containing 87.6% 1-butene fraction.

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Scheme 3

References

  1. 1.

    Wang J, Zhang N, Li CQ, Shi WG, Lin ZY (2016) Nickel complexes based on hyperbranched salicylaldimine ligands: synthesis, characterization, and catalytic properties for ethylene oligomerization. J Organomet Chem 822:104–111

    Article  CAS  Google Scholar 

  2. 2.

    Boulens P, Pellier E, Jeanneau E, Reek JNH, Olivier-Bourbigou H, Breuil P-AR (2015) Self-assembled organometallic nickel complexes as catalysts for selective dimerization of ethylene into 1-butene. Organomet 34(7):1139–1142

    Article  CAS  Google Scholar 

  3. 3.

    Chen H-P, Liu Y-H, Peng S-M, Liu S-T (2003) New bulky phosphino–pyridine ligands. Palladium and nickel complexes for the catalytic polymerization and oligomerization of ethylene. Organomet 22(24):4893–4899

    Article  CAS  Google Scholar 

  4. 4.

    Ngcobo M, Ojwach SO (2017) Nickel(II) complexes chelated by N,N (benzimidazolylmethyl)amine ligands: synthesis and catalytic behavior in tandem ethylene oligomerization and Friedel–Crafts alkylation reactions. Inorg Chim Acta 467:400–404

    Article  CAS  Google Scholar 

  5. 5.

    Popeney CS, Rheingold AL, Guan Z (2009) Nickel(II) and palladium(II) polymerization catalysts bearing a fluorinated cyclophane ligand: stabilization of the reactive intermediate. Organomet 28(15):4452–4463

    Article  CAS  Google Scholar 

  6. 6.

    Speiser F, Braunstein P, Saussine L (2004) New nickel ethylene oligomerization catalysts bearing bidentate P,N-phosphinopyridine ligands with different substituents α to phosphorus. Organomet 23(11):2625–2632

    Article  CAS  Google Scholar 

  7. 7.

    Lecocq V, Olivier-Bourbigou H (2007) Biphasic Ni-catalyzed ethylene oligomerization in ionic liquids. Oil Gas Sci Technol 62(6):761–773

    Article  CAS  Google Scholar 

  8. 8.

    Ortiz de la Tabla L, Matas I, Palma P, Álvarez E, Cámpora J (2012) Nickel and palladium complexes with new phosphinito-imine ligands and their application as ethylene oligomerization catalysts. Organomet 31(3):1006–1016

    Article  CAS  Google Scholar 

  9. 9.

    Huang Y, Zhang L, Wei W, Alam F, Jiang T (2018) Nickel-based ethylene oligomerization catalysts supported by PNSiP ligands. Phosphorus, Sulfur Silicon Relat Elem 193(6):363–368

    Article  CAS  Google Scholar 

  10. 10.

    Peterson JD (1967) Phosphinomethyllithium compounds IV: an improved method of preparation and some synthetic applications. J Organomet Chem 8(2):199–208

    Article  CAS  Google Scholar 

  11. 11.

    Zhang L, Meng X, Chen Y, Cao C, Jiang T (2017) Chromium-based ethylene tetramerization catalysts supported by silicon-bridged diphosphine ligands: further combination of high activity and selectivity. ChemCatChem 9(1):76–79

    Article  CAS  Google Scholar 

  12. 12.

    Zhang L, Wei W, Alam F, Chen Y, Jiang T (2017) Efficient chromium-based catalysts for ethylene tri-/tetramerization switched by silicon-bridged/N,P-based ancillary ligands: a structural, catalytic and DFT study. Catal Sci Technol 7(21):5011–5018

    Article  CAS  Google Scholar 

  13. 13.

    Sheldrick GM (1996) SADABS: program for empirical absorption correction of area detector data. University of Göttingen, Göttingen

    Google Scholar 

  14. 14.

    Sheldrick G (2008) A short history of SHELX. Acta Crystallogr Sect A 64(1):112–122

    Article  CAS  Google Scholar 

  15. 15.

    Dyer PW, Fawcett J, Hanton MJ (2008) Rigid N-phosphino guanidine P,N ligands and their use in nickel-catalyzed ethylene oligomerization. Organomet 27(19):5082–5087

    Article  CAS  Google Scholar 

  16. 16.

    Meng X, Zhang L, Chen Y, Jiang T (2016) Silane-bridged diphosphine ligands for nickel-catalyzed ethylene oligomerization. React Kinet Mech Catal 119(2):481–490

    Article  CAS  Google Scholar 

  17. 17.

    Sun Y, Chen Y, Mao G, Ning Y, Jiang T (2014) Boron- and silicon-bridged bis(diphenylphosphino)-type ligands for chromium-catalyzed ethylene oligomerization. Chin Sci Bull 59(21):2613–2617

    Article  CAS  Google Scholar 

  18. 18.

    Yang Q-Z, Kermagoret A, Agostinho M, Siri O, Braunstein P (2006) Nickel complexes with functional zwitterionic N,O-benzoquinonemonoimine-type ligands: syntheses, structures, and catalytic oligomerization of ethylene. Organomet 25(23):5518–5527

    Article  CAS  Google Scholar 

  19. 19.

    de Oliveira LL, Campedelli RR, Kuhn MCA, Carpentier J-F, Casagrande OL (2008) Highly selective nickel catalysts for ethylene oligomerization based on tridentate pyrazolyl ligands. J Mol Catal A: Chem 288(1):58–62

    Article  CAS  Google Scholar 

  20. 20.

    Zhang N, Wang J, Huo H, Chen L, Shi W, Li C, Wang J (2018) Iron, cobalt and nickel complexes bearing hyperbranched iminopyridyl ligands: synthesis, characterization and evaluation as ethylene oligomerization catalysts. Inorg Chim Acta 469:209–216

    Article  CAS  Google Scholar 

  21. 21.

    Aid A, Andrei RD, Amokrane S, Cammarano C, Nibou D, Hulea V (2017) Ni-exchanged cationic clays as novel heterogeneous catalysts for selective ethylene oligomerization. Appl Clay Sci 146:432–438

    Article  CAS  Google Scholar 

  22. 22.

    de Oliveira LL, da Silva SM, Casagrande ACA, Stieler R, Casagrande OL Jr (2018) Synthesis and characterization of Ni(II) complexes supported by phenoxy/naphthoxy-imine ligands with pendant N- and O-donor groups and their use in ethylene oligomerization. Appl Organomet Chem 32(7):e4414

    Article  CAS  Google Scholar 

  23. 23.

    Suo H, Zhang Y, Ma Z, Yang W, Flisak Z, Hao X, Hu X, Sun W-H (2017) 2-Chloro/phenyl-7-arylimino-6,6-dimethylcyclopenta[b]pyridylnickel chlorides: synthesis, characterization and ethylene oligomerization. Catal Commun 102:26–30

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was supported by the National Key Research and Development Program of China (2017YFB0306700). The Natural Science Foundation of Tianjin City (14JCYBJC23100, 15JCYBJC48100 and 16JCZDJC31600).

Author information

Affiliations

Authors

Corresponding author

Correspondence to Tao Jiang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

C2

CCDC numbers 1859463 and 1859467 contain the supplementary crystallographic data for and C3. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/. (DOC 3155 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Wei, W., Yu, B., Alam, F. et al. Ethylene oligomerization promoted by nickel-based catalysts with silicon-bridged diphosphine amine ligands. Transit Met Chem 44, 125–133 (2019). https://doi.org/10.1007/s11243-018-0276-7

Download citation