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Chemical conversion in 1-butelene hydroformylation catalyzed by the (Ar)3P/[Rh] system

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Abstract

In order to improve the selectivity of 2-methybutanal in the 1-butelene hydroformylation reaction, triarylphosphine ligands [(CnH2n+1–C6H4)3P (n = 4, L3; n = 6, L4; n = 8, L5; n = 10, L6)] are prepared by Friedel–Crafts alkylation reactions and characterized by 1H NMR, 13C NMR, 31P NMR and HRMS. When combined with Rh(acac)(CO)2, the L/[Rh] systems show high catalytic activity for the hydroformylation of 1-butelene. The influences of different substituents on the catalytic behavior are studied, and the effects of the molar ratio of [P]/[Rh], reaction temperature, reaction time and pressure of CO/H2 on the yield of 2-methylbutanal are also investigated. When the ratio of [P]/[Rh] = 3, the content of 2-methylbutanal in carbonyl products reaches 48.1%. It is surprising to find the intermediate conversion in 1-butelene hydroformylation reaction and the mechanism is proposed and discussed.

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Acknowledgements

The author is grateful to the National Natural Science Foundation of China for financial support for this Projects (U1162111 and U1362111), and GanSu Nature Science Foundation (1606RJZA114).

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Author notes

  1. Jing Wang and He Li have contributed equally to this work.

Authors and Affiliations

  1. Lanzhou Petrochemical College of Vocational Technology, Lanzhou, 730060, People’s Republic of China

    Jing Wang

  2. School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, People’s Republic of China

    Jing Wang, He Li, Yuling Zhu, Yan Zhao & Sheng Xu

Authors
  1. Jing Wang
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  2. He Li
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  3. Yuling Zhu
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  4. Yan Zhao
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  5. Sheng Xu
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Corresponding author

Correspondence to Sheng Xu.

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Wang, J., Li, H., Zhu, Y. et al. Chemical conversion in 1-butelene hydroformylation catalyzed by the (Ar)3P/[Rh] system. Reac Kinet Mech Cat 122, 1049–1062 (2017). https://doi.org/10.1007/s11144-017-1255-2

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  • DOI: https://doi.org/10.1007/s11144-017-1255-2

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