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Catalysis Letters

, Volume 147, Issue 9, pp 2269–2278 | Cite as

Catalytic Oxidation of Cyclopentene by O2 over Pd(II)-SBA-15 Complexes

  • Lumin Yue
  • Zhenwei Wang
  • Lele Bao
  • Wei Fu
  • Li Xu
  • Jun LiEmail author
  • Guanzhong Lu
Article
  • 245 Downloads

Abstract

Novel catalysts with Pd(II)-picolinamide complexes anchored into the channels of mesoporous material SBA-15 were prepared for chemical transformation of cyclopentene, and characterized in details. Spectra of 29Si NMR, 13C NMR and XPS revealed the organic ligands were grafted into the SBA-15 and Pd(II) complexes formed. Spacial diversity of the complexes, especially distances from –C=O to N on pyridyl cycles, may influence electronic distribution of conjugated system and further the catalytic activity. With the help of the newly synthesized catalytic materials, a new heterogeneous oxidation system was developed for selective catalytic transformation of cyclopentene to cyclopentanone with molecular oxygen as the sole oxidant. Analytic results of the reaction mixtures indicated that all catalysts exhibited high activity, while the cat.1 and cat.2 with 2-pyridinecarbonyl or 3-pyridinecarbonyl on the ligands gave better yields of cyclopentanone. 96.2% conversion of cyclopentene and 76.3% yied of cyclopentanone were achieved over the catalyst cat.2 under the conditions of 0.7 MPa O2, 323 K and 6 h reaction. In addition, the catalysts were also appealing for easy separation and recyclable property.

Graphical Abstract

A new heterogeneous reaction system was developed for the catalytic oxidation of cyclopentene to cyclopentanone by molecular oxygen over novel catalysts. The synthesized catalysts are comprised of Pd(II)-picolinamide complexes anchored into the channels of SBA-15. The new system was efficient for the mentioned reaction, and the catalysts were reusable.

Keywords

Cyclopentene oxidation Pd(II)-complexes Heterogeneous catalysis Cyclopentanone 

Notes

Acknowledgements

The authors gratefully acknowledge the financial support of Consortium Plan Project of Shanghai (LM201411), the support of Shanghai Institute of Technology, and the constant support and advice from the Applied Catalysis Group.

Supplementary material

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Supplementary material 1 (TIF 64 KB)
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Supplementary material 6 (TIF 878 KB)

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Lumin Yue
    • 1
  • Zhenwei Wang
    • 1
  • Lele Bao
    • 1
  • Wei Fu
    • 1
  • Li Xu
    • 1
  • Jun Li
    • 1
    Email author
  • Guanzhong Lu
    • 1
  1. 1.School of Chemical and Environmental EngineeringShanghai Institute of TechnologyShanghaiPeople’s Republic of China

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