Synthesis and evaluation of carbon-based solid catalyst from sugar bagasse biochar for selective conversion of fructose to 5-HMF

Vu Nam Trung; Vu Tue Minh; Truong Duc Duc; Le Quang Dien; Nguyen Trung Thanh; Tran Thi Thuy

doi:10.15625/2525-2518/20417

Author affiliations

Authors

Vu Nam Trung Hanoi University of Science and Technology, 1 Dai Co Viet Street, Bach Mai Ward, Ha Noi, Viet Nam
Vu Tue Minh Hanoi University of Science and Technology, 1 Dai Co Viet Street, Bach Mai Ward, Ha Noi, Viet Nam https://orcid.org/0009-0004-6177-0014
Truong Duc Duc Hanoi University of Science and Technology, 1 Dai Co Viet Street, Bach Mai Ward, Ha Noi, Viet Nam
Le Quang Dien Hanoi University of Science and Technology, 1 Dai Co Viet Street, Bach Mai Ward, Ha Noi, Viet Nam
Nguyen Trung Thanh Hanoi University of Science and Technology, 1 Dai Co Viet Street, Bach Mai Ward, Ha Noi, Viet Nam
Tran Thi Thuy Hanoi University of Science and Technology, 1 Dai Co Viet Street, Bach Mai Ward, Ha Noi, Viet Nam https://orcid.org/0000-0003-0678-2085

DOI:

https://doi.org/10.15625/2525-2518/20417

Keywords:

5-HMF, carbon-based solid acid catalyst, fructose, sugar bagasse

Abstract

A carbon-based solid acid catalyst was prepared from sugar bagasse by calcination of raw material and subsequent sulfonation step. The solid acid catalyst was characterized by XRD, TPD-NH3, FT-IR, and BET. Results showed that the catalyst has an amorphous carbon structure with surface area of above 750 m²/g, acid density of approximately 10.65 mmol/g and strong acid sites of -SO₃H. XPS analysis showed high content of functional groups on the surface of the catalyst. 5-HMF was synthesized from fructose using the catalyst. Influence of reaction time on fructose conversion and 5-HMF selectivity was investigated. At reaction time of 2.5 h, 100 % of fructose was converted to 5-HMF with selectivity of 93.22 %.

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References

1. Slak J., Pomeroy B., Kostyniuk A., Grilc M., Likozar B. – A review of bio-refining process intensification in catalytic conversion reactions, separations and purifications of hydroxymethylfurfural (HMF) and furfural. Chem. Eng. J., 429 (2022) 132325. https://doi.org/10.1016/j.cej.2021.132325.

2. Fan W., Verrier C., Queneau Y., Popowycz F. – 5-Hydroxymethylfurfural (HMF) in organic synthesis: a review of its recent applications towards fine chemicals. Curr. Org. Synth., 16 (2019) 583–614. https://doi.org/10.2174/1570179416666190412164738.

3. Kucherov F. A., Romashov L. V., Galkin K. I., Ananikov V. P. – Chemical transformations of biomass-derived C6-furanic platform chemicals for sustainable energy research, materials science, and synthetic building blocks. ACS Sustain. Chem. Eng., 6 (2018) 8064–8092. https://doi.org/10.1021/acssuschemeng.8b00971.

4. van Putten R.-J., Van Der Waal J. C., De Jong E., Rasrendra C. B., Heeres H. J., de Vries J. G. – Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem. Rev., 113 (2013) 1499–1597. https://doi.org/10.1021/cr300182k.

5. Vu Trung N., Pham Thi N., Nguyen T. H., Nguyen M. N., Tran Anh D., Nguyen Trung T., Tran Quang T., Than Van H., Tran Thi T. – Tuning the thermal and mechanical properties of poly (vinyl alcohol) with 2, 5-furandicarboxylic acid acting as a biobased crosslinking agent. Polym. J., 54 (2021) 335–343. https://doi.org/10.1038/s41428-021-00583-y.

6. Vu Trung N., Nguyen Ngoc M., Nguyen Thi Ngoc A., Pham Thi N., Tran Quang T., Tran Thi T. – Synthesis and characterizations of biobased copolymer poly (ethylene-co-butylene 2, 5-furandicarboxylate). Int. J. Polym. Sci., 2021 (2021) 1–8. https://doi.org/10.1155/2021/9104546.

7. Amarasekara A. S., Williams L. D., Ebede C. C. – Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 °C: an NMR study. Carbohydr. Res., 343 (2008) 3021–3024. https://doi.org/10.1016/j.carres.2008.09.008.

8. Assary R. S., Kim T., Low J. J., Greeley J., Curtiss L. A. – Glucose and fructose to platform chemicals: understanding the thermodynamic landscapes of acid-catalysed reactions using high-level ab initio methods. Phys. Chem. Chem. Phys., 14 (2012) 16603–16611. https://doi.org/10.1039/c2cp41842h.

9. Kimura H., Nakahara M., Matubayasi N. – Solvent effect on pathways and mechanisms for D-fructose conversion to 5-hydroxymethyl-2-furaldehyde: in situ 13C NMR study. J. Phys. Chem. A, 117 (2013) 2102–2113. https://doi.org/10.1021/jp312002h.

10. Fu X., Li S., Wen J., Kang F., Huang C., Zheng X. – Visible light-induced photo-Fenton dehydration of fructose into 5-hydroxymethylfurfural over ZnFe₂O₄-coated Ag nanowires. Colloids Surf. A Physicochem. Eng. Asp., 609 (2021) 125685. https://doi.org/10.1016/j.colsurfa.2020.125685.

11. Le G. T., Arunaditya K., Panichpol J., Rodruangnon T., Thongratkaew S., Chaipojjana K., Faungnawakij K., Charinpanitkul T. – Sulfonated magnetic carbon nanoparticles from eucalyptus oil as a green and sustainable catalyst for converting fructose to 5-HMF. Catal. Commun., 149 (2021) 106229. https://doi.org/10.1016/j.catcom.2020.106229.

12. Li M., Zhang Q., Luo B., Chen C., Wang S., Min D. – Lignin-based carbon solid acid catalyst prepared for selectively converting fructose to 5-hydroxymethylfurfural. Ind. Crops Prod., 145 (2020) 111920. https://doi.org/10.1016/j.indcrop.2019.111920.

13. Rathod P. V., Mujmule R. B., Chung W.-J., Jadhav A. R., Kim H. – Efficient dehydration of glucose, sucrose, and fructose to 5-hydroxymethylfurfural using tri-cationic ionic liquids. Catal. Lett., 149 (2019) 672–687. https://doi.org/10.1007/s10562-019-02667-0.

14. Delidovich I. – Recent progress in base-catalyzed isomerization of D-glucose into D-fructose. Curr. Opin. Green Sustain. Chem., 27 (2021) 100414. https://doi.org/10.1016/j.cogsc.2020.100414.

15. Yabushita M., Shibayama N., Nakajima K., Fukuoka A. – Selective glucose-to-fructose isomerization in ethanol catalyzed by hydrotalcites. ACS Catal., 9 (2019) 2101–2109. https://doi.org/10.1021/acscatal.8b05145.

16. Lin F., Wang K., Gao L., Guo X. – Efficient conversion of fructose to 5-hydroxymethylfurfural by functionalized γ-Al₂O₃ beads. Appl. Organomet. Chem., 33 (2019) e4821. https://doi.org/10.1002/aoc.4821.

17. He Q., Lu Y., Peng Q., Chen W., Fan G., Chai B., Song G. – Synthesis of 5-hydroxymethylfurfural from fructose catalyzed by sulfonated carbon-based solid acid. Biomass Convers. Biorefin., 13 (2021) 9195–9203. https://doi.org/10.1007/s13399-021-01847-6.

18. Kang S., Ye J., Chang J. – Recent advances in carbon-based sulfonated catalyst: preparation and application. Int. Rev. Chem. Eng., 5 (2013) 133–144.

19. Karimi B., Mirzaei H. M., Behzadnia H., Vali H. – Novel ordered mesoporous carbon based sulfonic acid as an efficient catalyst in the selective dehydration of fructose into 5-HMF: the role of solvent and surface chemistry. ACS Appl. Mater. Interfaces, 7 (2015) 19050–19059. https://doi.org/10.1021/acsami.5b03985.

20. Wang Q., Hao J., Zhao Z. – Microwave-assisted conversion of fructose to 5-hydroxymethylfurfural using sulfonated porous carbon derived from biomass. Aust. J. Chem., 71 (2017) 24–31. https://doi.org/10.1071/CH17154.

21. Huang J., Wang J., Huang Z., Liu T., Li H. – Photothermal technique-enabled ambient production of microalgae biodiesel: mechanism and life cycle assessment. Bioresour. Technol., 369 (2023) 128390. https://doi.org/10.1016/j.biortech.2022.128390.

22. Huang J., Jian Y., Li H., Fang Z. – Lignin-derived layered 3D biochar with controllable acidity for enhanced catalytic upgrading of Jatropha oil to biodiesel. Catal. Today, 404 (2022) 35–48. https://doi.org/10.1016/j.cattod.2022.04.016.

23. Kobayashi H., Fukuoka A. – Synthesis and utilisation of sugar compounds derived from lignocellulosic biomass. Green Chem., 15 (2013) 1740–1763. https://doi.org/10.1039/c3gc00060e.

24. Li X., Wang G., Hu Y., Iradukunda Y., Luo F., Yi K., Shi G. – Sulfonated carbon-titanium dioxide composite nanofiber tube catalysts for dehydration of sugars in biphasic solvents to obtain 5-hydroxymethylfurfural. J. Taiwan Inst. Chem. Eng., 129 (2021) 26–39. https://doi.org/10.1016/j.jtice.2021.09.025.

25. Thanh N. T., Long N. H., Dien L. Q., Phuong Ly G. T., Hoang P. H., Minh Phuong N. T., Hue N. T. – Preparation of carbonaceous solid acid catalyst from Acacia mangium wood sawdust for conversion of same source into 5-hydroxymethylfurfural. Energy Sources, Part A, 42 (2019) 730–739. https://doi.org/10.1080/15567036.2019.1602195.

26. Su F., Guo Y. – Advancements in solid acid catalysts for biodiesel production. Green Chem., 16 (2014) 2934–2957. https://doi.org/10.1039/C3GC42333F.

27. Das B., Mohanty K. – Sulfonic acid-functionalized carbon coated red mud as an efficient catalyst for the direct production of 5-HMF from D-glucose under microwave irradiation. Appl. Catal. A Gen., 622 (2021) 118237. https://doi.org/10.1016/j.apcata.2021.118237.

28. Gan L., Lyu L., Shen T., Wang S. – Sulfonated lignin-derived ordered mesoporous carbon with highly selective and recyclable catalysis for the conversion of fructose into 5-hydroxymethylfurfural. Appl. Catal. A Gen., 574 (2019) 132–143. https://doi.org/10.1016/j.apcata.2019.02.008.

29. Wang J., Zhang Z., Jin S., Shen X. – Efficient conversion of carbohydrates into 5-hydroxylmethylfurfan and 5-ethoxymethylfurfural over sufonic acid-functionalized mesoporous carbon catalyst. Fuel, 192 (2017) 102–107. https://doi.org/10.1016/j.fuel.2016.12.027.

30. Wang J. -g., Zhang Y. -y., Wang Y., Zhu L. -w., Cui H. -y., Yi W. -m. – Catalytic fructose dehydration to 5-hydroxymethylfurfural over sulfonated carbons with hierarchically ordered pores. J. Fuel Chem. Technol., 44 (2016) 1341–1348. https://doi.org/10.1016/S1872-5813(16)30058-5.

31. Fu Z., Wan H., Hu X., Cui Q., Guan G. – Preparation and catalytic performance of a carbon-based solid acid catalyst with high specific surface area. React. Kinet. Mech. Catal., 107 (2012) 203–213. https://doi.org/10.1007/s11144-012-0466-9.

32. Guan Q., Li Y., Chen Y., Shi Y., Gu J., Li B., Miao R., Chen Q., Ning P. – Sulfonated multi-walled carbon nanotubes for biodiesel production through triglycerides transesterification. RSC Adv., 7 (2017) 7250–7258. https://doi.org/10.1039/C6RA28067F.

33. Mardhiah H. H., Ong H. C., Masjuki H., Lim S., Pang Y. L. – Investigation of carbon-based solid acid catalyst from Jatropha curcas biomass in biodiesel production. Energy Convers. Manage., 144 (2017) 10–17. https://doi.org/10.1016/j.enconman.2017.04.038.

34. Wu Z.-Y., Yin P., Ju H.-X., Chen Z.-Q., Li C., Li S.-C., Liang H.-W., Zhu J.-F., Yu S.-H. – Natural nanofibrous cellulose-derived solid acid catalysts. Research (2019). https://doi.org/10.34133/2019/6262719.

35. Zhang T., Li W., Jin Y., Ou W. – Synthesis of sulfonated chitosan-derived carbon-based catalysts and their applications in the production of 5-hydroxymethylfurfural. Int. J. Biol. Macromol., 157 (2020) 368–376. https://doi.org/10.1016/j.ijbiomac.2020.04.148.