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Selective hydrogenation of unsaturated aldehydes over Pd catalyst supported on N-doped porous carbon

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Abstract

Selective hydrogenation of unsaturated aldehydes is one of the most important reactions in organic chemical industry. Herein, a N-doped Pd catalyst supported on porous carbon (Pd/NC) was prepared and examined on selective hydrogenation of 2-ethyl-2-hexenal (EHEA) to 2-ethylhexanal (EHA). The N-doped Pd/NC catalyst shows a superior catalytic conversion (i.e., about 1.4 times higher than that on the counterpart Pd/C catalyst at 353 K) and a remarkable selectivity (98%) to hydrogenating C=C bond on EHEA to the saturated product (2-ethylhexanal). The catalyst characterization results suggest that N do** can promote the electron density on the surface of Pd, which enhances the adsorption and further activation of hydrogen molecules so that it significantly improves the hydrogenation rate of 2-ethyl-2-hexenal. It is also clarified that the by-product, 2-ethylhexanol is formed via the hydrogenation of C=C bond in 2-ethyl-2-hexenol rather than the C=O group in 2-ethylhexanal. These interesting findings provide a promising strategy for future catalyst design and a meaningful understanding of selective hydrogenation of unsaturated aldehydes on Pd catalyst.

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References

  1. J.M. Grosselin, C. Mercier, G. Allmang, F. Grass, Organometallics 10, 7 (1991)

    Article  Google Scholar 

  2. P. Mäki-Arvela, J. Hájek, T. Salmi, D.Y. Murzin. Appl. Catal. A Gen. 292, (2005)

  3. X. Lan, T. Wang, X. Li, N. Huang, J. Wang, Catal. Sci. Technol. 6, 21 (2016)

    Google Scholar 

  4. F. Delbecq, P. Sautet, J. Catal. 152, 2 (1995)

    Article  Google Scholar 

  5. X. Lan, T. Wang, ACS Catal. 10, 4 (2020)

    Google Scholar 

  6. X. Wang, X. Liang, P. Geng, Q. Li, ACS Catal. 10, 4 (2020)

    Google Scholar 

  7. F. Delbecq, P. Sautet, J. Catal. 211, 2 (2002)

    Article  Google Scholar 

  8. J. Ma, L. Xu, L. Xu, H. Wang, S. Xu, H. Li, S. **e, H. Li, ACS Catal. 3, 5 (2013)

    Google Scholar 

  9. D. Wang, Y. Zhu, C. Tian, L. Wang, W. Zhou, Y. Dong, H. Yan, H. Fu, ChemCatChem 8, 9 (2016)

    Article  CAS  Google Scholar 

  10. Y. Zhang, X. Yang, Y. Zhou, G. Li, Z. Li, C. Liu, M. Bao, W. Shen, Nanoscale 8, 44 (2016)

    Article  CAS  Google Scholar 

  11. S. Chen, L. Meng, B. Chen, W. Chen, X. Duan, X. Huang, B. Zhang, H. Fu, Y. Wan, ACS Catal. 7, 3 (2017)

    Google Scholar 

  12. F. Jiang, J. Cai, B. Liu, Y. Xu, X. Liu, RSC Adv. 6, 79 (2016)

    Article  CAS  Google Scholar 

  13. S. Han, Y. Liu, J. Li, R. Li, F. Yuan, Y. Zhu, Catalysts 8, 5 (2018)

    Google Scholar 

  14. Z. Wei, Y. Gong, T. **ong, P. Zhang, H. Li, Y. Wang, Catal. Sci. Technol. 5, 1 (2015)

    Google Scholar 

  15. R. Nie, M. Miao, W. Du, J. Shi, Y. Liu, Z. Hou. Appl. Catal. B Environ. 180, (2016)

  16. R.K. Abasabadi, A.A. Khodadadi, Y. Mortazavi, Res. Chem. Intermed. 47, 4 (2021)

    Article  CAS  Google Scholar 

  17. L. Wu, Y. Long, J. Ma, G. Lu, Res. Chem. Intermed. 45, 7 (2019)

    Google Scholar 

  18. N. Guo, M. Li, Y. Wang, X. Sun, F. Wang, R. Yang, RSC Adv. 6, 103 (2016)

    Google Scholar 

  19. I. Ziccarelli, H. Neumann, C. Kreyenschulte, B. Gabriele, M. Beller, Chem. Commun. 52, 86 (2016)

    Article  CAS  Google Scholar 

  20. Y. Cao, B. Zhao, X. Bao, Y. Wang, ACS Catal. 8, 8 (2018)

    Article  CAS  Google Scholar 

  21. X. Xu, M. Tang, M. Li, H. Li, Y. Wang, ACS Catal. 4, 9 (2014)

    Article  CAS  Google Scholar 

  22. S. Ott, A. Orfanidi, H. Schmies, B. Anke, H.N. Nong, J. Hübner, U. Gernert, M. Gliech, M. Lerch, P. Strasser, Nat. Mater. 19, 1 (2020)

    Article  CAS  Google Scholar 

  23. Z. Li, J. Liu, C. **a, F. Li, ACS Catal. 3, 11 (2013)

    Google Scholar 

  24. X. Wu, H. Zhou, New J. Chem. 41, 18 (2017)

    Google Scholar 

  25. F. Wang, K. Han, L. Xu, H. Yu, W. Shi, Ind. Eng. Chem. Res. 60, 8 (2021)

    Google Scholar 

  26. L. Zhang, G. Wen, H. Liu, N. Wang, D.S. Su, ChemCatChem 6, 9 (2014)

    Google Scholar 

  27. L.-L. Wang, L.-P. Zhu, N.-C. Bing and L.-J. Wang. J. Phys. Chem. Solids 107, (2017)

  28. W.A. Wang, H. Huang, B. Wang, C. Qian, P. Li, J. Zhou, Z. Liang, C. Yang, S. Guo, Sci. Bull. 64, 21 (2019)

    Google Scholar 

  29. Y. Yang, D. Zeng, S. Shao, S. Hao, G. Zhu, B. Liu. J. Colloid Interf. Sci. 538, (2019)

  30. J. Zawadzki, M. Wiśniewski, K. Skowrońska, Appl. Catal. B Environ. 35, 4 (2002)

    Article  Google Scholar 

  31. M. Trchová, E.N. Konyushenko, J. Stejskal, J. Kovářová, G. Ćirić-Marjanović, Polym. Degrad. Stabil. 94, 6 (2009)

    Article  CAS  Google Scholar 

  32. Y. Zhu, G. Yu, J. Yang, M. Yuan, D. Xu and Z. Dong. J. Colloid Interf. Sci. 533, (2019)

  33. Z. Chunhui, Z. Yifeng, L. Huazhang, J. Rare Earths 28, 4 (2010)

    Google Scholar 

  34. L. Ma, P. Chen, G. Zhang, L. Wang, F. Tang, X. Zhao, J. Wang, J. Huang, Y.N. Liu, ChemCatChem 13, 14 (2021)

    Google Scholar 

  35. Y. Chen, J. Wang, H. Liu, M.N. Banis, R. Li, X. Sun, T.-K. Sham, S. Ye, S. Knights, J. Phys. Chem. C 115, 9 (2011)

    Google Scholar 

  36. M. Jeon, K.-S. Lee, S.H. Choi, J. Han, S.W. Nam, S.C. Jang, H.S. Park, C.W. Yoon, Int. J. Hydrog. Energy 41, 34 (2016)

    Google Scholar 

  37. Y.-H. Qin, Z.-Y. **ong, J. Ma, L. Yang, Z. Wu, W. Feng, T.-L. Wang, W.-G. Wang, C.-W. Wang, Int. J. Hydrog. Energy 42, 2 (2017)

    Google Scholar 

  38. G. Wu, C. Dai, D. Wang, D. Li, N. Li, J. Mater. Chem. A 20, 15 (2010)

    Article  Google Scholar 

  39. Z. He, B. Dong, W. Wang, G. Yang, Y. Cao, H. Wang, Y. Yang, Q. Wang, F. Peng, H. Yu, ACS Catal. 9, 4 (2019)

    Google Scholar 

  40. G. Wang, S. Yuan, Z. Wu, W. Liu, H. Zhan, Y. Liang, X. Chen, B. Ma, S. Bi, Appl. Organomet. Chem. 33, 11 (2019)

    Google Scholar 

  41. J. Yang, X. Qi, F. Shen, M. Qiu, R.L. Smith Jr. Sci. Total Environ. 719, (2020)

  42. Y. Cao, W. Fu, Z. Ren, Z. Sui, J. Zhou, J. Luo, X. Duan, X. Zhou, AICHE J. 66, 4 (2020)

    Google Scholar 

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Acknowledgements

We are grateful for the financial support from the National Natural Science Foundation of China (21878227).

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National Natural Science Foundation of China, 21878227, Yujun Zhao.

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Correspondence to Yan Xu or Yujun Zhao.

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Sun, S., Pan, D., Huang, H. et al. Selective hydrogenation of unsaturated aldehydes over Pd catalyst supported on N-doped porous carbon. Res Chem Intermed 48, 3129–3142 (2022). https://doi.org/10.1007/s11164-022-04744-3

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