Hydrogenolysis of furfuryl alcohol to 1,2-pentanediol catalyzed by first row transition metal salts

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DOI: https://doi.org/10.21924/cst.9.2.2024.1549
Keywords:
ZrOCl\(_2\).8H\(_2\)O, VOSO\(_4\).H\(_2\)O, FeCl\(_3\).6H\(_2\)O, 1,2-pentanadiol, hydrogenolysis, furfuryl alcohol

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Muhammad Rafi Pratama
Department of Chemistry, State University of Malang, Malang 65145, Indonesia
Istifhamy Irnanda
Department of Chemistry, State University of Malang, Malang 65145, Indonesia
Hendra Julius Situmorang
Department of Chemistry, State University of Malang, Malang 65145, Indonesia
Yessi Permana
Inorganic and Physical Chemistry Research Division, Institut Teknologi Bandung, Bandung 40132, Indonesia
Siti Hartinah Qurbayni
Inorganic and Physical Chemistry Research Division, Institut Teknologi Bandung, Bandung 40132, Indonesia
Husni Wahyu Wijaya
Department of Chemistry, State University of Malang, Malang 65145, Indonesia; Centre of Advanced Material for Renewable Energy, Universitas Negeri Malang, Malang 65145, Indonesia
Ubed Sonai Fahruddin Arrozi
Department of Chemistry, State University of Malang, Malang 65145, Indonesia

Abstract

The growing and relatively large market share of 1,2-pentanediol (1,2-PeD) has attracted attention of researchers to find effective and economically viable catalysts. One type of catalyst that can be used for synthesizing this compound is transition-metal-based catalysts, employed in the hydrogenolysis of furfuryl alcohol (FOL). In this study, the hydrogenolysis of furfuryl alcohol were performed with 2-propanol as the hydrogen source and transition metal salts as the catalysts. The used catalysts include first-row early and late transition metals, i.e., ZrOCl2·8H2O, VOSO4·H2O, FeSO4·7H2O, CuSO4·5H2O, NiCl2, Al(NO3)3·H2O, CoCl2, FeCl3·6H2O, and Zn(NO3)2·6H2O. It was found that ZrOCl2·8H2O, VOSO4·H2O, and FeCl3·6H2O demonstrated superior catalytic activity compared to the other catalysts. Optimal reaction conditions for these three catalysts were achieved at 150 °C for 1 hour, using 2-propanol as the hydrogen source. Under these reaction conditions, the ZrOCl?·8H?O catalyst achieved 95.5% conversion of FOL and 30.3% yield of 1,2-PeD, while the VOSO?·H?O catalyst attained 80.5% conversion of FOL and 36.9% yield of 1,2-PeD. Both results were obtained with a low catalyst concentration of 0.6 mmol%. Meanwhile, the FeCl3·6H2O catalyst converted 94.9% of FOL and yielded 30.9% of 1,2-PeD, using a lower catalyst concentration of 0.4 mmol%. Kinetic studies suggested that the reactions likely follow pseudo-first-order kinetics with experimental activation energies (Ea) of 65 kJ/mol, 55 kJ/mol, and 37 kJ/mol for ZrOCl?·8H?O, VOSO?·H?O, and FeCl?·6H?O catalysts, respectively. These findings highlight the potential of transition-metal-based catalysts in achieving high efficiency with low loading, emphasizing their suitability for industrial applications.

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Pratama, M. R., Irnanda, I., Situmorang, H. J., Permana, Y., Qurbayni, S. H., Wijaya, H. W., & Arrozi, U. S. F. (2024). Hydrogenolysis of furfuryl alcohol to 1,2-pentanediol catalyzed by first row transition metal salts. Communications in Science and Technology, 9(2), 421-429. https://doi.org/10.21924/cst.9.2.2024.1549
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Vol. 9 No. 2 (2024)
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References

1. P. Mardina, H. Wijayanti, A. Tuhuloula, E. Hijriyati, Sarifah, Corncob residue as heterogeneous acid catalyst for green synthesis of biodiesel: A short review, Commun. Sci. Technol. 6 (2021) 60–68.

2. W. Trisunaryanti, K. Wijaya, A.M. Tazkia, Preparation of Ni/ZSM-5 and Mo/ZSM-5 catalysts for hydrotreating palm oil into biojet fuel, Commun. Sci. Technol. 9 (2024) 161–169.

3. D.A. Ramdhani, W. Trisunaryanti, Triyono, Study of green and sustainable heterogeneous catalyst produced from Javanese Moringa oleifera leaf ash for the transesterification of Calophyllum inophyllum seed oil, Commun. Sci. Technol. 8 (2023) 124–133.

4. A. Yamaguchi, Y. Murakami, T. Imura, K. Wakita, Hydrogenolysis of Furfuryl Alcohol to 1,2-Pentanediol Over Supported Ruthenium Catalysts, ChemistryOpen 10 (2021) 731–736.

5. I. Agostini, S. Cupferman, Cosmetic composition comprising an aqueous dispersion of film-forming polymer particles containing 1,2-pentanediol, US Patent No. 6296858B1 (1999).

6. O.-A. Antoce, V. Antoce, N. Mori, S. Yasui, A. Kobayashi, K. Takahashi, Calorimetric Evaluation of the Antimicrobial Properties of 1, 3-butanediol and 1, 2-pentanediol on Various Microorganisms, Netsu Sokutei 25 (1998) 2–8.

7. D.S. Pisal, G.D. Yadav, Single-Step Hydrogenolysis of Furfural to 1,2-Pentanediol Using a Bifunctional Rh/OMS-2 Catalyst, ACS Omega 4 (2019) 1201–1214.

8. C. Jian, H.X. Yifangyun, Method for synthesizing 1,2-pentanediol by one-pot method, CN Patent No. CN104926600A (2015).

9. L. Bruna, M. Cardona-Farreny, V. Colliere, K. Philippot, M.R. Axet, In Situ Ruthenium Catalyst Modification for the Conversion of Furfural to 1,2-Pentanediol, Nanomaterials 12 (2022) 328.

10. F. Gao, H. Liu, X. Hu, J. Chen, Z. Huang, C. Xia, Selective hydrogenolysis of furfuryl alcohol to 1,5- and 1,2-pentanediol over Cu-LaCoO3 catalysts with balanced Cu0-CoO sites, Chin. J. Catal. 39 (2018) 1711–1723.

11. O. Koch, A. Köckritz, M. Kant, A. Martin, A. Schöning, U. Armbruster, et al., Method for producing 1,2-pentanediol, US Patent No. US20140066666A1 (2012).

12. R. Seki, N. Hara, T. Saito, Y. Nakao, Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex, J. Am. Chem. Soc. 143 (2021) 6388–6394.

13. H. Liu, Z. Huang, F. Zhao, F. Cui, X. Li, C. Xia, J. Chen, Efficient hydrogenolysis of biomass-derived furfuryl alcohol to 1,2- and 1,5-pentanediols over a non-precious Cu–Mg3AlO4.5 bifunctional catalyst, Catal. Sci. Technol. 6 (2016) 668–671.

14. H. Liu, Z. Huang, H. Kang, C. Xia, J. Chen, Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2- and 1,5-pentanediol over highly dispersed Cu-Al2O3 catalysts, Chin. J. Catal. 37 (2016) 700–710.

15. F. Gao, H. Liu, X. Hu, J. Chen, Z. Huang, C. Xia, Selective hydrogenolysis of furfuryl alcohol to 1,5- and 1,2-pentanediol over Cu-LaCoO3 catalysts with balanced Cu0-CoO sites, Chin. J. Catal. 39 (2018) 1711–1723.

16. B. Zhang, Y. Zhu, G. Ding, H. Zheng, Y. Li, Selective conversion of furfuryl alcohol to 1,2-pentanediol over a Ru/MnOx catalyst in aqueous phase, Green Chem. 14 (2012) 3402–3409.

17. T. Tong, X. Liu, Y. Guo, M. Norouzi Banis, Y. Hu, Y. Wang, The critical role of CeO2 crystal-plane in controlling Pt chemical states on the hydrogenolysis of furfuryl alcohol to 1,2-pentanediol, J. Catal. 365 (2018) 420–428.

18. M.J. Gilkey, B. Xu, Heterogeneous Catalytic Transfer Hydrogenation as an Effective Pathway in Biomass Upgrading, ACS Catal. 6 (2016) 1420–1436.

19. M. Trincado, J. Bösken, H. Grützmacher, Homogeneously catalysed acceptorless dehydrogenation of alcohols: A progress report, Coord. Chem. Rev. 443 (2021) 213967.

20. A.H. Valekar, M. Lee, J.W. Yoon, J. Kwak, D.Y. Hong, K.R. Oh, G.Y. Cha, Y.U. Kwon, J. Jung, J.S. Chang, Y.K. Hwang, Catalytic Transfer Hydrogenation of Furfural to Furfuryl Alcohol under Mild Conditions over Zr-MOFs: Exploring the Role of Metal Node Coordination and Modification, ACS Catal. 10 (2020) 3720–3732.

21. F. Li, S. Jiang, J. Huang, Y. Wang, S. Lu, C. Li, Catalytic transfer hydrogenation of furfural to furfuryl alcohol over a magnetic Fe3O4@C catalyst, New J. Chem. 44 (2019) 478–486.

22. Z. Gao, L. Yang, G. Fan, F. Li, Promotional Role of Surface Defects on Carbon-Supported Ruthenium-Based Catalysts in the Transfer Hydrogenation of Furfural, ChemCatChem 8 (2016) 3769–3779.

23. J. Zhang, J. Chen, Selective Transfer Hydrogenation of Biomass-Based Furfural and 5-Hydroxymethylfurfural over Hydrotalcite-Derived Copper Catalysts Using Methanol as a Hydrogen Donor, ACS Sustain. Chem. Eng. 5 (2017) 5982–5993.

24. S.H. Qurbayni, H.W. Wijaya, U.S. Fahruddin Arrozi, Y. Permana, Single-Step Hydrogenolysis of Furfuryl Alcohol to 1,2-Pentanediol by CoWO4 Catalyst, Chem. Inorg. Mat. 2 (2024) 100036.

25. H.W. Wijaya, T. Kojima, T. Hara, N. Ichikuni, S. Shimazu, Synthesis of 1,5-Pentanediol by Hydrogenolysis of Furfuryl Alcohol over Ni–Y2O3 Composite Catalyst, ChemCatChem 9 (2017) 2869–2874.

26. D. Götz, M. Lucas, P. Claus, Aqueous Phase Hydrogenolysis of Bio-Derivable Furfuryl Alcohol to Pentanediols Using Copper Catalysts, Catalysts 7 (2017) 50.

27. Z. An, J. Li, Recent advances in the catalytic transfer hydrogenation of furfural to furfuryl alcohol over heterogeneous catalysts, Green Chem. 24 (2022) 1780–1808.

28. J.G. West, D. Huang, E.J. Sorensen, Acceptorless dehydrogenation of small molecules through cooperative base metal catalysis, Nat. Commun. 6 (2015) 1–7.

29. M. Nielsen, A. Kammer, D. Cozzula, H. Junge, S. Gladiali, M. Beller, Efficient Hydrogen Production from Alcohols under Mild Reaction Conditions, Angew. Chem., Int. Ed. Engl. 50 (2011) 9593–9597.

30. M. Trincado, J. Bösken, H. Grützmacher, Homogeneously catalyzed acceptorless dehydrogenation of alcohols: A progress report, Coord. Chem. Rev. 443 (2021) 213967.

31. R. Ma, X.P. Wu, T. Tong, Z.J. Shao, Y. Wang, X. Liu, Q. Xia, X.Q. Gong, The Critical Role of Water in the Ring Opening of Furfural Alcohol to 1,2-Pentanediol, ACS Catal. 7 (2017) 333–337.

32. H. Shafaghat, I.G. Lee, J. Jae, S.C. Jung, Y.K. Park, Pd/C catalyzed transfer hydrogenation of pyrolysis oil using 2-propanol as hydrogen source, Chem. Eng. J. 377 (2019) 119986.