SpringerLink
Log in

Selective transformation of biomass-derived 5-hydroxymethylfurfural to the building blocks 2,5-bis(hydroxymethyl)furan on α-Ni(OH)2/SiO2 catalyst without prereduction

  • Published:
Reaction Kinetics, Mechanisms and Catalysis Aims and scope Submit manuscript

Abstract

A series of low-cost α-Ni(OH)2/SiO2 catalysts were successfully fabricated by the vapor-induced internal hydrolysis method, then the hydrogenation of 5-hydroxymethylfurfural (HMF) to 2,5-bis(hydroxymethyl)furan (BHMF) was investigated by using the ethanol as the hydrogen donor over these as-prepared α-Ni(OH)2/SiO2 catalysts. Based on the reaction results, these as-prepared catalysts, which could dispense with extra pre-reduction treatment before reactions, exhibited superior catalytic performance for the HMF hydrogenation to BHMF. A remarkable intrinsic selectivity of BHMF selectivity of almost 100% with about 90% HMF conversion could be obtained under 195 °C for 5 h in an N2 atmosphere over the α-Ni(OH)2/SiO2 catalyst of 5-Ni(OH)2/SiO2 with about 5 wt% Ni on SiO2. The almost constant HMF conversion and BHMF intrinsic selectivity found from the recycling tests can indicate that the catalyst was stable without the obvious loss of its catalytic activity after recycling. Moreover, the mechanism of HMF hydrogenation using ethanol over the α-Ni(OH)2/SiO2 catalysts could be referred to as the mechanism of the Meerwein-Ponndorf-Verley reaction. This work will provide a simple synthesis method for future design and development of high-performance, low-cost, and low-energy consumption catalysts for HMF hydrogenation to BHMF.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Thailand)

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 1
Fig. 7
Fig. 8
Fig. 9
Scheme 2

Similar content being viewed by others

Data Availability

The data has been redescribed.

References

  1. Tang X, Wei J, Ding N, Sun Y, Zeng X, Hu L, Liu S, Lei T, Lin L (2017) Chemoselective hydrogenation of biomass derived 5-hydroxymethylfurfural to diols: key intermediates for sustainable chemicals, materials and fuels. Renew Sust Energ Rev 77:287–296

    Article  CAS  Google Scholar 

  2. Hameed S, Lin L, Wang A, Luo W (2020) Recent developments in metal-based catalysts for the catalytic aerobic oxidation of 5-hydroxymethyl-furfural to 2,5-furandicarboxylic acid. Catalysts 10(1):120

    Article  CAS  Google Scholar 

  3. Fang W, Riisager A (2021) Recent advances in heterogeneous catalytic transfer hydrogenation/hydrogenolysis for valorization of biomass-derived furanic compounds. Green Chem 23(2):670–688

    Article  CAS  Google Scholar 

  4. Wang L, Zuo J, Zhang Q, Peng F, Chen S, Liu Z (2022) Catalytic transfer hydrogenation of biomass-derived 5-hydroxymethylfurfural into 2,5-dihydroxymethylfuran over Co/UiO-66-NH2. Catal Lett 152(2):361–371

    Article  CAS  Google Scholar 

  5. Cao Q, Liang W, Guan J, Wang L, Qu Q, Zhang X, Wang X, Mu X (2014) Catalytic synthesis of 2,5-bis-methoxymethylfuran: a promising cetane number improver for diesel. Appl Catal A: Gen 481:49–53

    Article  CAS  Google Scholar 

  6. Alipour S, Omidvarborna H, Kim DS (2017) A review on synthesis of alkoxymethyl furfural, a biofuel candidate. Renew Sust Energ Rev 71:908–926

    Article  CAS  Google Scholar 

  7. Zhao W, Wang F, Zhao K, Liu X, Zhu X, Yan L, Yin Y, Xu Q, Yin D (2023) Recent advances in the catalytic production of bio-based diol 2,5-bis(hydroxymethyl)furan. Carbon Resources Convers 6(2):116–131

    Article  CAS  Google Scholar 

  8. Alamillo R, Tucker M, Chia M, Pagán-Torres Y, Dumesic J (2012) The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts. Green Chem 14(5):1413–1419

    Article  CAS  Google Scholar 

  9. Mishra DK, Lee HJ, Truong CC, Kim J, Suh Y-W, Baek J, Kim YJ (2020) Ru/MnCo2O4 as a catalyst for tunable synthesis of 2,5-bis(hydroxymethyl)furan or 2,5-bis(hydroxymethyl)tetrahydrofuran from hydrogenation of 5-hydroxymethylfurfural. Mol Catal 484:110722

    Article  CAS  Google Scholar 

  10. Zhang K, Meng Q, Wu H, He M, Han B (2022) Selective hydrogenolysis of 5-hydroxymethylfurfural into 2,5-dimethylfuran under mild conditions using Pd/MOF-808. ACS Sustain Chem Eng 10(31):10286–10293

    Article  CAS  Google Scholar 

  11. Padilla R, Koranchalil S, Nielsen M (2020) Efficient and selective catalytic hydrogenation of furanic aldehydes using well defined Ru and Ir pincer complexes. Green Chem 22(20):6767–6772

    Article  CAS  Google Scholar 

  12. Hao W, Li W, Tang X, Zeng X, Sun Y, Liu S, Lin L (2016) Catalytic transfer hydrogenation of biomass-derived 5-hydroxymethyl furfural to the building block 2,5-bishydroxymethyl furan. Green Chem 18(4):1080–1088

    Article  CAS  Google Scholar 

  13. Valentini F, Kozell V, Petrucci C, Marrocchi A, Gu Y, Gelman D, Vaccaro L (2019) Formic acid, a biomass-derived source of energy and hydrogen for biomass upgrading. Energ Environ Sci 12(9):2646–2664

    Article  CAS  Google Scholar 

  14. Johnson TC, Morris DJ, Wills M (2010) Hydrogen generation from formic acid and alcohols using homogeneous catalysts. Chem Soc Rev 39(1):81–88

    Article  CAS  PubMed  Google Scholar 

  15. Krishnan CK, Hayashi T, Ogura M (2008) A new method for post-synthesis coating of zirconia on the mesopore walls of SBA-15 without pore blocking. Adv Mater 20(11):2131–2136

    Article  Google Scholar 

  16. Wallbridge SP, Lawson K, Catling AE, Kirk CA, Dann SE (2022) Synthesis and spectroscopic identification of nickel and cobalt layered hydroxides and hydroxynitrates. Dalton T 51(47):18010–18023

    Article  CAS  Google Scholar 

  17. Xu L, Ding Y-S, Chen C-H, Zhao L, Rimkus C, Joesten R, Suib SL (2008) 3D flowerlike α-nickel hydroxide with enhanced electrochemical activity aynthesized by microwave-assisted hydrothermal method. Chem Mater 20(1):308–316

    Article  CAS  Google Scholar 

  18. Rajamathi M, Vishnu Kamath P (1998) On the relationship between α-nickel hydroxide and the basic salts of nickel. J Power Sources 70(1):118–121

    Article  CAS  Google Scholar 

  19. Ma Y, Yang M, ** X (2020) Formation mechanisms for hierarchical nickel hydroxide microstructures hydrothermally prepared with different nickel salt precursors. Coll Surface A 588:124374

    Article  CAS  Google Scholar 

  20. Park S, Khan Z, Shin TJ, Kim Y, Ko H (2019) Rechargeable Na/Ni batteries based on the Ni(OH)2/NiOOH redox couple with high energy density and good cycling performance. J Mater Chem A 7(4):1564–1573

    Article  CAS  Google Scholar 

  21. Hall DS, Lockwood DJ, Poirier S, Bock C, MacDougall BR (2012) Raman and infrared spectroscopy of α and β phases of thin nickel hydroxide films electrochemically formed on nickel. J Phys Chem A 116(25):6771–6784

    Article  CAS  PubMed  Google Scholar 

  22. Xa C, Chen X, Zhang F, Yang Z, Huang S (2013) One-pot hydrothermal synthesis of reduced graphene oxide/carbon nanotube/α-Ni(OH)2 composites for high performance electrochemical supercapacitor. J Power Source 243:555–561

    Article  Google Scholar 

  23. Grosseau-Poussard JL, Dinhut JF, Silvain JF, Sabot R (1999) Role of a chromium ion implantation on the corrosion behaviour of nickel in artificial sea water. Appl Surface Sci 151(1):49–62

    Article  CAS  Google Scholar 

  24. Ghesquiere C, Lemaitre J, Herbillon AJ (1982) An investigation of the nature and reducibility of Ni-hydroxy-montmorillonites using various methods including temperature-programmed reduction (TPR). Clay Miner 17(2):217–230

    Article  CAS  Google Scholar 

  25. Wang CB, Gau GY, Gau SJ, Tang CW, Bi JL (2005) Preparation and characterization of nanosized nickel oxide. Catal Lett 101(3):241–247

    Article  CAS  Google Scholar 

  26. Aghazadeh M, Golikand AN, Ghaemi M (2011) Synthesis, characterization, and electrochemical properties of ultrafine β-Ni(OH)2 nanoparticles. Int J Hydrogen Energ 36(14):8674–8679

    Article  CAS  Google Scholar 

  27. Baraldi P, Davolio G, Fabbri G, Manfredini T (1989) A spectral and thermal study on nickel(II) hydroxydes. Mater Chem Phys 21(5):479–493

    Article  CAS  Google Scholar 

  28. Clause O, Bonneviot L, Che M (1992) Effect of the preparation method on the thermal stability of silica-supported nickel oxide as studied by EXAFS and TPR techniques. J Catal 138(1):195–205

    Article  CAS  Google Scholar 

  29. Zhang C, Zhu W, Li S, Wu G, Ma X, Wang X, Gong J (2013) Sintering-resistant Ni-based reforming catalysts obtained via the nanoconfinement effect. Chem Commun 49(82):9383–9385

    Article  CAS  Google Scholar 

  30. Zhang X, Tang W, Zhang Q, Wang T, Ma L (2017) Hydrocarbons production from lignin-derived phenolic compounds over Ni/SiO2 catalyst. Energy Procedia 105:518–523

    Article  CAS  Google Scholar 

  31. **a WS, Hou YH, Chang G, Weng WZ, Han GB, Wan HL (2012) Partial oxidation of methane into syngas (H2+CO) over effective high-dispersed Ni/SiO2 catalysts synthesized by a sol-gel method. Int J Hydrogen Energ 37(10):8343–8353

    Article  CAS  Google Scholar 

  32. Hu D, Hu H, ** H, Zhang P, Hu Y, Ying S, Li X, Yang Y, Zhang J, Wang L (2020) Building hierarchical zeolite structure by post-synthesis treatment to promote the conversion of furanic molecules into biofuels. Appl Catal A: Gen 590:117338

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the Natural Science Foundation of Fujian Province of China (2021J01154), Natural Science Foundation of Academy of Carbon Neutrality of Fujian Normal University (TZH2022-04) for our funding.

Author information

Authors and Affiliations

  1. Fujian Provincial University Engineering Research Center of Industrial Biocatalysis, College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, 350007, People’s Republic of China

    Weixing Pan, Hui Chen & Aicheng Chen

Authors
  1. Weixing Pan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hui Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aicheng Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aicheng Chen.

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 327 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pan, W., Chen, H. & Chen, A. Selective transformation of biomass-derived 5-hydroxymethylfurfural to the building blocks 2,5-bis(hydroxymethyl)furan on α-Ni(OH)2/SiO2 catalyst without prereduction. Reac Kinet Mech Cat 137, 1635–1649 (2024). https://doi.org/10.1007/s11144-024-02587-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-024-02587-0

Keywords

Search

Navigation