Abstract
5-Hydroxymethylfurfural (HMF) is a high value-added platform compound, converted into bio-based polyesters and biofuels etc. In this paper, we used two commercially available hexamethylenimine and cetyltrimethylammonium bromide (CTAB) as the structure-directing agents to synthesize HMWW zeolite nanosheets via one step. A series of HMWW zeolite nanosheets with different disorder index (DI) were controllably prepared by adjusting the amount of CTAB, operating also as an in situ exfoliating agent, converting fructose into HMF in the tetrahydrofuran/NaCl-H2O biphasic solvent with low boiling point. Successful construction of disordered HMWW zeolite nanosheets was verified by PXRD. Further characterizations by BET, SEM and TEM etc. show that HMWW4.0 with the optimum DI of 0.67 has a disordered network-like arrangement of layers with the external surface area of 224 m2/g and the mesoporous size of 3.5 nm. Catalytic evaluations showed that HMF selectivity was closely related to DI of the catalysts. Under the optimized DI, fructose molecules are readily accessible to acidic sites on the external surface while larger external surface area is exposed. The HMWW4.0 zeolite catalyzed fructose dehydration in the biphasic solvent, producing 90% HMF selectivity with 93% fructose conversion at 140 °C for 6 h. In the reuses of the HMWW4.0 catalyst, HMF selectivity was around 90% with fructose conversion decreasing by ca. 10% after six runs, indicating that it possesses the promising stability.
Graphical Abstract
Similar content being viewed by others
References
Bozell JJ, Petersen GR (2010) Technology development for the production of biobased products from biorefinery carbohydrates—the US department of energy’s “Top 10” revisited. Green Chem 12(4):539–554
Li T, Ong SSG, Zhang J et al (2020) One-pot conversion of carbohydrates into furan derivatives in biphasic tandem catalytic process. Catal Today 339:296–304
García-Sancho C, Fúnez-Núñez I, Moreno-Tost R et al (2017) Beneficial effects of calcium chloride on glucose dehydration to 5-hydroxymethylfurfural in the presence of alumina as catalyst. Appl Catal B 206:617–625
Nahavandi M, Kasanneni T, Yuan ZS et al (2019) Efficient conversion of glucose into 5-hydroxymethylfurfural using a sulfonated carbon-based solid acid catalyst: an experimental and numerical study. ACS Sustain Chem Eng 7(14):11970–11984
Danielli da Fonseca Ferreira A, Dorneles de Mello M, da Silva MAP (2018) Catalytic oxidation of 5-hydroxymethylfurfural to 2, 5-furandicarboxylic acid over Ru/Al2O3 in a trickle-bed reactor. Ind Eng Chem Res 58(1):128–137
Liu B, Ren Y, Zhang Z (2015) Aerobic oxidation of 5-hydroxymethylfurfural into 2, 5- furandicarboxylic acid in water under mild conditions. Green Chem 17(3):1610–1617
Yuan Z, Liu B, Zhou P et al (2018) Aerobic oxidation of biomass-derived 5-hydroxymethylfurfural to 2, 5-diformylfuran with cesium-doped manganese dioxide. Catal Sci Technol 8(17):4430–4439
Megías-Sayago C, Lolli A, Ivanova S et al (2019) Au/Al2O3–efficient catalyst for 5-hydroxymethylfurfural oxidation to 2, 5-furandicarboxylic acid. Catal Today 333:169–175
Kazi FK, Patel AD, Serrano-Ruiz JC et al (2011) Techno-economic analysis of dimethylfuran (DMF) and hydroxymethylfurfural (HMF) production from pure fructose in catalytic processes. Chem Eng J 169(1–3):329–338
Román-Leshkov Y, Barrett CJ, Liu ZY et al (2007) Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 447(7147):982–985
Bohre A, Alam MI, Avasthi K et al (2020) Low temperature transformation of lignocellulose derived bioinspired molecules to aviation fuel precursor over magnesium–lanthanum mixed oxide catalyst. Appl Catal B 276:119069
Šivec R, Grilc M, Huš M et al (2019) Multiscale modeling of (hemi) cellulose hydrolysis and cascade hydrotreatment of 5-hydroxymethylfurfural, furfural, and levulinic acid. Ind Eng Chem Res 58(35):16018–16032
Chen PX, Tang Y, Zhang B et al (2014) 5-Hydroxymethyl-2-furfural and derivatives formed during acid hydrolysis of conjugated and bound phenolics in plant foods and the effects on phenolic content and antioxidant capacity. Food Chem 62(20):4754–4761
Shao X, Li Z, Qian X et al (2009) Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: replacement of nitromethylene with nitroconjugated system. J Agric Food Chem 57(3):951–957
Anastas P, Eghbali N (2010) Green chemistry: principles and practice. Chem Soc Rev 39(1):301–312
Perez GP, Mukherjee A, Dumont MJ (2019) Insights into HMF catalysis. J Ind Eng Chem 70:1–34
Robyt JF, John F (1998) Essentials of carbohydrate chemistry. Springer, New York, pp 48–75
Kuster BFM (1990) 5-Hydroxymethylfurfural (HMF). A review focussing on its manufacture. Starch-Stärke 42(8):314–321
Song X, Yue J, Zhu Y et al (2021) Efficient conversion of glucose to 5- hydroxymethylfurfural over a Sn-modified SAPO-34 zeolite catalyst. Ind Eng Chem Res 60(16):5838–5851
Liu R, Chen J, Huang X et al (2013) Conversion of fructose into 5-hydroxymethylfurfural and alkyl levulinates catalyzed by sulfonic acid-functionalized carbon materials. Green Chem 15(10):2895–2903
Han H, Zhao H, Liu Y et al (2017) Efficient conversion of fructose into 5-hydroxymethylfurfural over WO3/reduced graphene oxide catalysts. RSC Adv 7(7):3790–3795
Xie Y, Yuan W, Huang Y et al (2019) Zirconyl schiff base complex-functionalized MCM-41 catalyzes dehydration of fructose into 5-hydroxymethylfurfural in organic solvents. Chinese Chem Lett 30(2):359–362
Prasad D, Patil KN, Manoorkar VK et al (2021) Sustainable catalytic process for fructose dehydration using dicationic ionic liquid assisted zsm-5 zeolite. Mater Manuf Process 36(13):1571–1578
Slak J, Pomeroy B, Kostyniuk A et al (2022) A review of bio-refining process intensification in catalytic conversion reactions, separations and purifications of hydroxymethylfurfural (HMF) and furfural. Chem Eng J 429:132325
Zakrzewska ME, Bogel-Łukasik E, Bogel-Łukasik R (2011) Ionic liquid-mediated formation of 5-hydroxymethylfurfural—a promising biomass-derived building block. Chem Rev 111(2):397–417
Román-Leshkov Y, Chheda JN, Dumesic JA (2006) Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312(5782):1933–1937
Bicker M, Hirth J, Vogel H (2003) Dehydration of fructose to 5-hydroxymethylfurfural in sub-and supercritical acetone. Green Chem 5(2):280–284
Wang K, Liu S, Hao R et al (2021) Catalytic coupling boosting efficient production of 5- hydroxymethylfurfural from glucose. AIChE J 67(10):e17345
Roth WJ, Nachtigall P, Morris RE et al (2014) Two-dimensional zeolites: current status and perspectives. Chem Rev 114(9):4807–4837
Xu L, Wu P (2016) Diversity of layered zeolites: from synthesis to structural modifications. New J Chem 40(5):3968–3981
Xu L, Sun J (2016) Recent advances in the synthesis and application of two-dimensional zeolites. Adv Energy Mater 6(17):1600441
Lu K, Huang J, Ren L et al (2020) High ethylene selectivity in methanol-to-olefin (MTO) reaction over mor-zeolite nanosheets. Angew Chem Int Ed 132(15):6317–6321
Rodrigues MV, Vignatti C, Garetto T et al (2015) Glycerol dehydration catalyzed by MWW zeolites and the changes in the catalyst deactivation caused by porosity modification. Appl Catal A 495:84–91
Carriço CS, Cruz FT, dos Santos MB et al (2016) MWW-type catalysts for gas phase glycerol dehydration to acrolein. J Catal 334:34–41
Xu W, Miller SJ, Agrawal PK et al (2013) Zeolite topology effects in the alkylation of phenol with propylene. Appl Catal A 459:114–120
Arias KS, Climent MJ, Corma A et al (2015) Synthesis of high quality alkyl naphthenic kerosene by reacting an oil refinery with a biomass refinery stream. Energy Environ Sci 8(1):317–331
Maheshwari S, Jordan E, Kumar S et al (2008) Layer structure preservation during swelling, pillaring, and exfoliation of a zeolite precursor. J Am Chem Soc 130(4):1507–1516
Liu S, Wang K, Hao R, et al (2023) Highly selective 5-hydroxymethylfurfural from fructose by pillared HMFI zeolite nanosheets in biphasic solvents, AIChE J. submitting
Na K, Choi M, Park W et al (2010) Pillared MFI zeolite nanosheets of a single-unit-cell thickness. J Am Chem Soc 132(12):4169–4177
Zhou Y, Mu Y, Hsieh MF et al (2020) Enhanced surface activity of MWW zeolite nanosheets prepared via a one-step synthesis. J Am Chem Soc 142(18):8211–8222
Corma A, Corell C, Pérez-Pariente J (1995) Synthesis and characterization of the MCM-22 zeolite. Zeolites 15(1):2–8
Zhao Y, Lu K, Xu H et al (2019) Comparative study on the dehydration of biomass-derived disaccharides and polysaccharides to 5-hydroxymethylfurfural. Energy Fuels 33(10):9985–9995
Hu Q, Tan R, Yao W et al (2020) Preparation and X-ray photoelectron spectroscopic characterization of Sn-doped C12A7: e− electride nanoparticles. Appl Surf Sci 508:145244
Liu F, Wang T, Zheng Y et al (2017) Synergistic effect of Brønsted and Lewis acid sites for the synthesis of polyoxymethylene dimethyl ethers over highly efficient SO42−/TiO2 catalysts. J Catal 355:17–25
Pagan-Torres YJ, Wang T, Gallo JMR et al (2012) Production of 5-hydroxymethylfurfural from glucose using a combination of Lewis and Brønsted acid catalysts in water in a biphasic reactor with an alkylphenol solvent. ACS Catal 2(6):930–934
Netrabukkana R, Lourvanij K, Rorrer GL (1996) Diffusion of glucose and glucitol in microporous and mesoporous silicate/aluminosilicate catalysts. Ind Eng Chem Res 35(2):458–464
Leonowicz ME, Lawton JA, Lawton SL et al (1994) MCM-22: a molecular sieve with two independent multidimensional channel systems. Science 264(5167):1910–1913
Acknowledgements
We are grateful to the Advanced Analysis & Testing Center of Nanjing Forestry University for the relative measurements.
Funding
This work was supported by the Introduction Project of School-Level Highly Educated Talents (163030061) and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
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.
About this article
Cite this article
Hao, R., Du, A., Zhu, Q. et al. Disordered HMWW Zeolite Nanosheets Catalyzing Fructose to 5-Hydroxymethylfurfural. Catal Lett 154, 181–190 (2024). https://doi.org/10.1007/s10562-023-04287-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-023-04287-1