Skip to main content
Log in

Selective Hydrogenation of Nitroarenes by Single-Atom Pt Catalyst Through Hydrogen Transfer Reaction

  • Original Paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

Hydrogen transfer reaction is one of the valuable and potential solutions for selective hydrogenation. We report here that single-atom Pt supported by CeO2 could effectively catalyze the selective hydrogenation of nitroaromatics to corresponding amine through hydrogen transfer reaction.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Hao CH, Guo X, Pan YT, Chen S, Jiao Z, Yang H, Guo XY (2016) Visible-light-driven selective photocatalytic hydrogenation of cinnamaldehyde over Au/SiC catalysts. J Am Chem Soc 138(30):9361

    Article  CAS  PubMed  Google Scholar 

  2. Roeder GJ, Kelly HR, Yang G, Bauer TJ, Baráth E (2021) Selective Heterogeneous transfer hydrogenation from tertiary amines to alkynes. ACS Catal 11(9):5405–5415

    Article  CAS  Google Scholar 

  3. Zhang L, Zhou M, Wang A, Zhang T (2019) Selective hydrogenation over supported metal catalysts: from nanoparticles to single atoms. Chem Rev 120(2):683

    Article  PubMed  Google Scholar 

  4. Zhang Y, Gyngazova MS, Lolli A, Grazia L, Tabanelli T, Cavani F, Albonetti S (2019) Hydrogen transfer reaction as an alternative reductive process for the valorization of biomass-derived building blocks. Stud Surf Sci Catal 178:195–214

    Article  CAS  Google Scholar 

  5. Xu M, Yao S, Rao D, Niu Y, Liu N, Peng M, Zhai P, Man Y, Zheng L, Wang B (2018) Insights into interfacial synergistic catalysis over Ni@TiO2-x catalyst toward water-gas shift reaction. J Am Chem Soc 140(36):11241–11251

    Article  CAS  PubMed  Google Scholar 

  6. Li T, Chen F, Lang R, Wang H, Su Y, Qiao B, Wang A, Zhang T (2020) Styrene hydroformylation with in situ hydrogen: regioselectivity control by coupling with the low-temperature water–gas shift reaction. Angew Chem 132(19):7430

    Article  Google Scholar 

  7. Shang Q, Tang N, Qi H, Chen S, Cong Y (2020) A palladium single-atom catalyst toward efficient activation of molecular oxygen for cinnamyl alcohol oxidation. Chin J Catal 41(12):1812–1817

    Article  CAS  Google Scholar 

  8. Mza C, Man Y, Xy A, Xz A, Lei SD, Wd D, Awa B, Jl E, Tao Z (2020) On the mechanism of H2 activation over single-atom catalyst: an understanding of Pt1/WOx in the hydrogenolysis reaction. Chin J Catal 41(3):524–532

    Article  Google Scholar 

  9. Wang W, Lin L, Qi H, Cao W, Luo W (2021) MIL-53 (Al) derived single-atom Rh catalyst for the selective hydrogenation of m-chloronitrobenzene into m-chloroaniline. Chin J Catal 42(5):824–834

    Article  Google Scholar 

  10. Qu J, Xiao J, Chen H, Liu X, Zhang Q (2021) Orbital symmetry matching: achieving superior nitrogen reduction reaction over single-atom catalysts anchored on Mxene substrates. Chin J Catal 42(2):288–296

    Article  CAS  Google Scholar 

  11. Aitbekova A, Wrasman CJ, Riscoe AR, Kunz LY, Cargnello M (2020) Determining number of sites on ceria stabilizing single atoms via metal nanoparticle redispersion. Chin J Catal 41(6):998–1005

    Article  CAS  Google Scholar 

  12. Zhou D, Zhang L, Liu W, Xu G, Yin J (2021) Reaction kinetics and phase behavior in the chemoselective hydrogenation of 3-nitrostyrene over Co-N-C single-atom catalyst in compressed CO2. Chin J Catal 42(9):1617–1624

    Article  CAS  Google Scholar 

  13. Zhu C, Liang JX, Meng Y, Lin J, Cao Z (2021) Mn-corrolazine-based 2D-nanocatalytic material with single Mn atoms for catalytic oxidation of alkane to alcohol. Chin J Catal 42(6):1030–1039

    Article  CAS  Google Scholar 

  14. Jiang JS, Wei HL, Tan AD, Si R, Yu YX (2021) Fabricating high-loading Fe-N4 single-atom catalysts for oxygen reduction reaction by carbon-assisted pyrolysis of metal complexes. Chin J Catal 42(5):753–761

    Article  CAS  Google Scholar 

  15. Zhou X (2021) TiO2-supported single-atom catalysts for photocatalytic reactions. Acta Physico-Chim Sin 37(6):2008064

    Google Scholar 

  16. Han B (2021) Single NiN3 atoms for efficient electrochemical reduction of CO2. Acta Physico-Chim Sin 37(7):2010068

    Google Scholar 

  17. Dong F (2021) High-performance single-atom implanted metal-organic framework/MNO2 for NOx oxidation in plasma. Acta Phys-Chim Sin 37(8):2010074

    Google Scholar 

  18. Zhou J, Ao Z, An T (2021) DFT study of the decomposition mechanism of H2S on V-decorated Ti2CO2 single-atom catalyst. Acta Physico-Chim Sin 37(8):2007086

    Google Scholar 

  19. Huang X, Ma Y, Zhi L (2022) Ultrathin nitrogenated carbon nanosheets with single-atom nickel as an efficient catalyst for electrochemical CO2 reduction. Acta Physico-Chim Sin 38(2):211050

    Google Scholar 

  20. Zhang X, Zhang M, Deng Y, Xu M, Ma D (2021) A stable low-temperature H2-production catalyst by crowding Pt on α-MoC. Nature 589(7842):396–401

    Article  CAS  PubMed  Google Scholar 

  21. Peng M, Dong C, Gao R, Xiao D, Liu H, Ma D (2021) Fully exposed cluster catalyst (FECC): toward rich surface sites and full atom utilization efficiency. ACS Cent Sci 7(2):262–273

    Article  CAS  PubMed  Google Scholar 

  22. Han B, Guo Y, Huang Y, Xi W, Xu J, Luo J, Qi H, Ren Y, Liu X, Qiao B (2020) Strong metal–support interactions between Pt single atoms and TiO2. Angew Chem Int Ed 59(29):11824

    Article  CAS  Google Scholar 

  23. Pei GX, Liu XY, Yang X, Zhang L, Wang A, Li L, Wang H, Wang X, Zhang T (2017) Performance of Cu-alloyed Pd single-atom catalyst for semihydrogenation of acetylene under simulated front-end conditions. ACS Catal 7(2):1491–1500

    Article  CAS  Google Scholar 

  24. Zhang Z, Zhu Y, Asakura H, Zhang B, Zhang J, Zhou M, Han Y, Tanaka T, Wang A, Zhang T (2017) Thermally stable single atom Pt/m-Al2O3 for selective hydrogenation and CO oxidation. Nat Commun 8:16100

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Huang F, Deng Y, Chen Y, Cai X, Peng M, Jia Z, Ren P, Xiao D, Wen X, Wang N (2018) Atomically dispersed Pd on nanodiamond/graphene hybrid for selective hydrogenation of acetylene. J Am Chem Soc 140(41):13142–13146

    Article  CAS  PubMed  Google Scholar 

  26. Liu Z, Huang F, Peng M, Chen Y, Cai X, Wang L, Hu Z, Wen X, Wang N, Xiao D, Jiang H, Sun H, Liu H, Ma D (2021) Tuning the selectivity of catalytic nitriles hydrogenation by structure regulation in atomically dispersed Pd catalysts. Nat Commun 12:6194

    Article  PubMed  PubMed Central  Google Scholar 

  27. Liu L, Corma A (2018) Metal catalysts for heterogeneous catalysis: from single atoms to nanoclusters and nanoparticles. Chem Rev 2018:4981–5079

    Article  Google Scholar 

  28. Li T, Liu F, Tang Y, Li L, Miao S, Su Y, Zhang J, Huang J, Sun H, Haruta M (2018) Maximizing the number of interfacial sites in single-atom catalysts for the highly selective, solvent-free oxidation of primary alcohols. Angew Chem Int Ed 57(26):7795–7799

    Article  CAS  Google Scholar 

  29. Tang Y, Asokan C, Xu MJ, Graham GW, Pan XQ, Christopher P, Li J, Sautet P (2019) Rh single atoms on TiO2 dynamically respond to reaction conditions by adapting their site. Nat Commun 10:4488

    Article  PubMed  PubMed Central  Google Scholar 

  30. Beswick O, Parastaev A, Yuranov I, LaGrange T, Dyson PJ, Kiwi-Minsker L (2017) Highly dispersed cobalt oxides nanoparticles on activated carbon fibres as efficient structured catalysts for the transfer hydrogenation of m-nitrostyrene. Catal Today 279:29–35

    Article  CAS  Google Scholar 

  31. Wang J, Yuan Z, Nie R, Hou Z, Zheng X (2010) Hydrogenation of nitrobenzene to aniline over silica gel supported nickel catalysts. Ind Eng Chem Res 49(10):4664–4669

    Article  CAS  Google Scholar 

  32. Fujita S-I, Watanabe H, Katagiri A, Yoshida H, Arai M (2014) Nitrogen and oxygen-doped metal-free carbon catalysts for chemoselective transfer hydrogenation of nitrobenzene, styrene, and 3-nitrostyrene with hydrazine. J Mol Catal A Chem 393:257–262

    Article  CAS  Google Scholar 

  33. Wei H, Liu X, Wang A, Zhang L, Qiao B, Yang X, Huang Y, Miao S, Liu J, Zhang T (2014) FeOx-supported platinum single-atom and pseudo-single-atom catalysts for chemoselective hydrogenation of functionalized nitroarenes. Nat Commun 5:5634

    Article  CAS  PubMed  Google Scholar 

  34. Serna P, Boronat M, Corma A (2011) Tuning the behavior of Au and Pt catalysts for the chemoselective hydrogenation of nitroaromatic compounds. Top Catal 54(5):439–446

    Article  CAS  Google Scholar 

  35. Ding GD, Hao LD, Xu HP, Wang LG, Chen J, Li T, Tu XM, Zhang Q (2020) Atomically dispersed palladium catalyses Suzuki-Miyaura reactions under phosphine-free conditions. Commun Chem 3(1):8

    Article  Google Scholar 

  36. Fujiwara K, Pratsinis SE (2018) Single Pd atoms on TiO2 dominate photocatalytic NOx removal. Appl Catal B-Environ 226:127–134

    Article  CAS  Google Scholar 

  37. Lu ZS, Lv P, Xue J, Wang HH, Wang YZ, Huang Y, He CZ, Mac DW, Yang ZX (2015) Pd-1/BN as a promising single atom catalyst of CO oxidation: a dispersion-corrected density functional theory study. RSC Adv 5(103):84381–84388

    Article  CAS  Google Scholar 

  38. Qiao BT, Liang JX, Wang AQ, Xu CQ, Li J, Zhang T, Liu JY (2015) Ultrastable single-atom gold catalysts with strong covalent metal-support interaction (CMSI). Nano Res 8(9):2913–2924

    Article  CAS  Google Scholar 

  39. Wang BL, Yue YX, Jin CX, Lu JY, Wang SS, Yu L, Guo LL, Li RR, Hu ZT, Pan ZY, Zhao J, Li XN (2020) Hydrochlorination of acetylene on single-atom Pd/N-doped carbon catalysts: Importance of pyridinic-N synergism. Appl Catal B-Environ 272:11

    Article  Google Scholar 

  40. Lang R, Xi W, Liu JC, Cui YT, Li T, Lee AF, Chen F, Chen Y, Li L, Li L (2019) Non defect-stabilized thermally stable single-atom catalyst. Nat Commun 10:234

    Article  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (22102210).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Tianbo Li or Botao Qiao.

Ethics declarations

Conflict of interest

The authors declare no competing financial interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 137 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, T., Jian, X., Jiang, Q. et al. Selective Hydrogenation of Nitroarenes by Single-Atom Pt Catalyst Through Hydrogen Transfer Reaction. Top Catal 65, 1604–1608 (2022). https://doi.org/10.1007/s11244-022-01566-w

Download citation

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-022-01566-w

Keywords

Navigation