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Journal articles on the topic 'Dehydration of fructose to HMF'

Author: Grafiati

Published: 9 March 2023

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1

Li, Hu, and Song Yang. "Catalytic Transformation of Fructose and Sucrose to HMF with Proline-Derived Ionic Liquids under Mild Conditions." International Journal of Chemical Engineering 2014 (2014): 1–7. http://dx.doi.org/10.1155/2014/978708.

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L-Proline derived ionic liquids (ILs) used as both solvent and catalyst were efficient for transformation of fructose and sucrose to 5-hydroxymethylfurfural (HMF) in the presence of water. Response surface methodology (RSM) was employed to optimize fructose dehydration process, and a maximum HMF yield of 73.6% could be obtained at 90°C after 50 min. The recycling of the IL exhibited an almost constant activity during five successive trials, and a possible reaction mechanism for the dehydration of fructose to HMF was proposed.

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2

Testa, Maria Luisa, Gianmarco Miroddi, Marco Russo, Valeria La Parola, and Giuseppe Marcì. "Dehydration of Fructose to 5-HMF over Acidic TiO2 Catalysts." Materials 13, no. 5 (March 6, 2020): 1178. http://dx.doi.org/10.3390/ma13051178.

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Different solid sulfonic titania-based catalysts were investigated for the hydrothermal dehydration of fructose to 5-hydroxymethylfurfural (5-HMF). The catalytic behavior of the materials was evaluated in terms of fructose conversion and selectivity to 5-HMF. The surface and structural properties of the catalysts were investigated by means of X-ray diffraction (XRD), N2 adsorption isotherms, thermo-gravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS) and acid capacity measurements. Special attention was focused on the reaction conditions, both in terms of 5-HMF selectivity and the sustainability of the process, choosing water as the solvent. Among the various process condition studied, TiO2-SO3H catalyzed a complete conversion (99%) of 1.1M fructose and 5-HMF selectivity (50%) and yield (50%) at 165 °C. An important improvement of the HMF selectivity (71%) was achieved when the reaction was carried out by using a lower fructose concentration (0.1M) and lower temperature (140 °C). The catalytic activities of the materials were related to their acid capacities as much as their textural properties. In particular, a counterbalance between the acidity and the structure of the pores in which the catalytic sites are located, results in the key issue for switch the selectivity towards the achievement of 5-HMF.

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3

Ye, Boyong, Wenyang Zhang, Ruru Zhou, Yuanyuan Jiang, Zixin Zhong, and Zhaoyin Hou. "Dehydration of fructose to 5-hydroxymethylfurfural over a mesoporous sulfonated high-crosslinked polymer in different solvents." New Journal of Chemistry 46, no. 14 (2022): 6756–64. http://dx.doi.org/10.1039/d2nj00142j.

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4

Lin, Changqu, Chaoqun Chai, Yuanzhang Li, Jiao Chen, Yanyu Lu, Hongli Wu, Lili Zhao, et al. "CaCl2 molten salt hydrate-promoted conversion of carbohydrates to 5-hydroxymethylfurfural: an experimental and theoretical study." Green Chemistry 23, no. 5 (2021): 2058–68. http://dx.doi.org/10.1039/d0gc04356g.

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33.6% fructose and 52.1% HMF were achieved from glucose isomerization and dehydration in CaCl₂ salt hydrate. Interactions existing in β-glucopyranose-CaCl₂ and β-d-fructofuranose-Ca²⁺ promoted the glucose isomerization and fructose dehydration.

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5

García-López, Elisa I., Francesca Rita Pomilla, Bartolomeo Megna, Maria Luisa Testa, Leonarda Francesca Liotta, and Giuseppe Marcì. "Catalytic Dehydration of Fructose to 5-Hydroxymethylfurfural in Aqueous Medium over Nb2O5-Based Catalysts." Nanomaterials 11, no. 7 (July 13, 2021): 1821. http://dx.doi.org/10.3390/nano11071821.

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The catalytic dehydration of fructose to 5-hydroxymethylfurfural (HMF) in water was performed in the presence of pristine Nb2O5 and composites containing Nb and Ti, Ce or Zr oxides. In all experiments, fructose was converted to HMF using water as the solvent. The catalysts were characterized by powder X-ray diffraction, scanning electron microscopy, N2 physical adsorption, infrared and Raman spectroscopy and temperature-programmed desorption of NH3. Experimental parameters such as fructose initial concentration, volume of the reacting suspension, operation temperature, reaction time and amount of catalyst were tuned in order to optimize the catalytic reaction process. The highest selectivity to HMF was ca. 80% in the presence of 0.5 g·L−1 of bare Nb2O5, Nb2O5-TiO2 or Nb2O5-CeO2 with a maximum fructose conversion of ca. 70%. However, the best compromise between high conversion and high selectivity was reached by using 1 g·L−1 of pristine Nb2O5. Indeed, the best result was obtained in the presence of Nb2O5, with a fructose conversion of 76% and a selectivity to HMF of 75%, corresponding to the highest HMF yield (57%). This result was obtained at a temperature of 165° in an autoclave after three hours of reaction by using 6 mL of 1 M fructose suspension with a catalyst amount equal to 1 g·L−1.

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6

Gimbernat, Alexandra, Marie Guehl, Nicolas Lopes Ferreira, Egon Heuson, Pascal Dhulster, Mickael Capron, Franck Dumeignil, Damien Delcroix, Jean Girardon, and Rénato Froidevaux. "From a Sequential Chemo-Enzymatic Approach to a Continuous Process for HMF Production from Glucose." Catalysts 8, no. 8 (August 17, 2018): 335. http://dx.doi.org/10.3390/catal8080335.

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Notably available from the cellulose contained in lignocellulosic biomass, glucose is a highly attractive substrate for eco-efficient processes towards high-value chemicals. A recent strategy for biomass valorization consists on combining biocatalysis and chemocatalysis to realise the so-called chemo-enzymatic or hybrid catalysis. Optimisation of the glucose conversion to 5-hydroxymethylfurfural (HMF) is the object of many research efforts. HMF can be produced by chemo-catalyzed fructose dehydration, while fructose can be selectively obtained from enzymatic glucose isomerization. Despite recent advances in HMF production, a fully integrated efficient process remains to be demonstrated. Our innovative approach consists on a continuous process involving enzymatic glucose isomerization, selective arylboronic-acid mediated fructose complexation/transportation, and chemical fructose dehydration to HMF. We designed a novel reactor based on two aqueous phases dynamically connected via an organic liquid membrane, which enabled substantial enhancement of glucose conversion (70%) while avoiding intermediate separation steps. Furthermore, in the as-combined steps, the use of an immobilized glucose isomerase and an acidic resin facilitates catalyst recycling.

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7

Liu, Shuqing, Xing Fu, Jinhang Dai, Zhongbao Liu, Liangfang Zhu, and Changwei Hu. "One-Pot Synthesis of 2,5-Diformylfuran from Fructose by Bifunctional Polyaniline-Supported Heteropolyacid Hybrid Catalysts." Catalysts 9, no. 5 (May 13, 2019): 445. http://dx.doi.org/10.3390/catal9050445.

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We report the preparation of bifunctional hybrid catalysts by supporting H3PMo12O40 (PMo12) heteropolyacid (HPA) on polyaniline (PAN) or formyl-functionalized PAN (F-PAN) for the “one-pot” and “one-step” synthesis of 2,5-diformylfuran (DFF) from fructose via 5-hydroxymethylfurfural (HMF) intermediate. We show that the PMo12 HPA is the main active species for both fructose dehydration and HMF oxidation owing to its Brønsted acidic and redox characters. However, the anchoring of PMo12 on PAN reduces the Brønsted acidity by acid–base interaction between protons in HPA and quinoid diimine structure in PAN, thereby reducing the dehydration performance. We demonstrate that the catalytic dehydration performance of the hybrid catalyst could be strengthened by grafting formyl groups on PAN before HPA anchoring. The highest DFF yield of 76.7% is obtained by conducting the “one-pot” reaction over the 40-PMo12/F3-PAN catalyst at 413 K for 7 h in air, wherein the side-reactions of fructose or HMF degradation and HMF rehydration have been significantly reduced. This hybrid catalyst is reusable without significant activity loss, highlighting the designing of stable inorganic–organic hybrid catalysts for producing valuable hexose-derived platform chemicals.

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8

Ma, Yubo, Lei Wang, Hongyi Li, Tianfu Wang, and Ronghui Zhang. "Selective Dehydration of Glucose into 5-Hydroxymethylfurfural by Ionic Liquid-ZrOCl2 in Isopropanol." Catalysts 8, no. 10 (October 18, 2018): 467. http://dx.doi.org/10.3390/catal8100467.

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In this work, a heterogeneous catalytic system consisting of [HO2CMMIm]Cl and ZrOCl2 in isopropanol is demonstrated to be effective for 5-hydroxymethylfurfural (HMF) synthesis with glucose as the feedstock. Various reaction conditions for HMF synthesis by glucose dehydration were investigated systematically. Under optimized reaction conditions, as high as 43 mol% HMF yield could be achieved. Increasing the water content to a level below 3.17% led to the production of HMF with a higher yield, while a lower HMF yield was observed when the water content was increased above 3.17%. In addition, the data also showed that ZrOCl2 could not only effectively convert glucose into intermediate species (which were not fructose, in contrast to the literature) but also catalyze the intermediate species’ in situ dehydration into HMF. [HO2CMMIm]Cl was used to catalyze the intermediate species’ in situ conversion to HMF. The kinetics data showed that a temperature increase accelerated the intermediate species’ dehydration reaction rate. The reaction of glucose dehydration was a strong endothermal reaction.

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9

Rajmohan, Rajamani, Subramaniyan Gayathri, and Pothiappan Vairaprakash. "Facile synthesis of 5-hydroxymethylfurfural: a sustainable raw material for the synthesis of key intermediates toward 21,23-dioxaporphyrins." RSC Adv. 5, no. 121 (2015): 100401–7. http://dx.doi.org/10.1039/c5ra19400h.

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In a simple and conceptually designed method for the dehydration of fructose on a solid support, 5-hydroxymethylfurfural (HMF) was synthesized in more than 95% isolated yield from fructose under very mild conditions at room temperature.

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10

Whitaker, Mariah R., Aamena Parulkar, and Nicholas A. Brunelli. "Selective production of 5-hydroxymethylfurfural from fructose in the presence of an acid-functionalized SBA-15 catalyst modified with a sulfoxide polymer." Molecular Systems Design & Engineering 5, no. 1 (2020): 257–68. http://dx.doi.org/10.1039/c9me00093c.

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11

Qu, Yong Shui, Yan Lei Song, Chong Pin Huang, Jie Zhang, and Biao Hua Chen. "Dehydration of Fructose to 5-Hydroxymethylfurfural Catalyzed by Alkaline Ionic Liquid." Advanced Materials Research 287-290 (July 2011): 1585–90. http://dx.doi.org/10.4028/www.scientific.net/amr.287-290.1585.

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The preparation of 5-hydroxymethylfurfural (5-HMF) through the dehydration of fructose with room temperature ionic liquids (ILs) has received much attention as a way of producing liquid fuels from renewable resources, but the cost of the process is considerably increased with IL as a solvent rather than as a catalyst. In this work, we have shown that the alkaline Ionic Liquid, 1-Butyl-3-methylimidazolium Hydroxide ([BMIM]OH), can be used as a catalyst in the conversion of fructose to 5-HMF. The maximum yield of 5-HMF was 91.6% at 160 °C after 8 h using dimethylsulfoxide (DMSO) as solvent, and the ketose is more easily dehydrated than aldose in this catalyst system.

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12

Xu, Daozhu, Qi Li, Jiacheng Ni, Yucai He, and Cuiluan Ma. "Significant Enhancement of 5-Hydroxymethylfural Productivity from D-Fructose with SG(SiO2) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine." Molecules 27, no. 18 (September 6, 2022): 5748. http://dx.doi.org/10.3390/molecules27185748.

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5-Hydroxymethyl-2-furfurylamine (5-HMFA) as an important 5-HMF derivative has been widely utilized in the manufacture of diuretics, antihypertensive drugs, preservatives and curing agents. In this work, an efficient chemoenzymatic route was constructed for producing 5-(hydroxymethyl)furfurylamine (5-HMFA) from biobased D-fructose in deep eutectic solvent Betaine:Glycerol–water. The introduction of Betaine:Glycerol could greatly promote the dehydration of D-fructose to 5-HMF and inhibit the secondary decomposition reactions of 5-HMF, compared with a single aqueous phase. D-Fructose (200 mM) could be catalyzed to 5-HMF (183.4 mM) at 91.7% yield by SG(SiO2) (3 wt%) after 90 min in Betaine:Glycerol (20 wt%), and at 150 °C. E. coli AT exhibited excellent bio-transamination activity to aminate 5-HMF into 5-HMFA at 35 °C and pH 7.5. After 24 h, D-fructose-derived 5-HMF (165.4 mM) was converted to 5-HMFA (155.7 mM) in 94.1% yield with D-Ala (D-Ala-to-5-HMF molar ratio 15:1) in Betaine:Glycerol (20 wt%) without removal of SG(SiO2), achieving a productivity of 0.61 g 5-HMFA/(g substrate D-fructose). Chemoenzymatic valorization of D-fructose with SG(SiO2) and E. coli AT was established for sustainable production of 5-HMFA, which has potential application.

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13

Ma, Yubo, Shaojun Qing, Lei Wang, Nurali Islam, Shuzhe Guan, Zhixian Gao, Xamxikamar Mamat, Hongyi Li, Wumanjiang Eli, and Tianfu Wang. "Production of 5-hydroxymethylfurfural from fructose by a thermo-regulated and recyclable Brønsted acidic ionic liquid catalyst." RSC Advances 5, no. 59 (2015): 47377–83. http://dx.doi.org/10.1039/c5ra08107f.

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14

Tschirner, Sarah, Eric Weingart, Linda Teevs, and Ulf Prüße. "Catalytic Dehydration of Fructose to 5-Hydroxymethylfurfural (HMF) in Low-Boiling Solvent Hexafluoroisopropanol (HFIP)." Molecules 23, no. 8 (July 26, 2018): 1866. http://dx.doi.org/10.3390/molecules23081866.

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A mixture of hexafluoroisopropanol (HFIP) and water was used as a new and unknown monophasic reaction solvent for fructose dehydration in order to produce HMF. HFIP is a low-boiling fluorous alcohol (b.p. 58 °C). Hence, HFIP can be recovered cost efficiently by distillation. Different ion-exchange resins were screened for the HFIP/water system in batch experiments. The best results were obtained for acidic macroporous ion-exchange resins, and high HMF yields up to 70% were achieved. The effects of various reaction conditions like initial fructose concentration, catalyst concentration, water content in HFIP, temperature and influence of the catalyst particle size were evaluated. Up to 76% HMF yield was attained at optimized reaction conditions for high initial fructose concentration of 0.5 M (90 g/L). The ion-exchange resin can simply be recovered by filtration and reused several times. This reaction system with HFIP/water as solvent and the ion-exchange resin Lewatit K2420 as catalyst shows excellent performance for HMF synthesis.

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15

Han, Miaomiao, Xiao Liu, Guangcheng Huang, Yadong Liu, and Shengxiang Ji. "Phosphoric acid doped polybenzimidazole as an heterogeneous catalyst for selective and efficient dehydration of saccharides to 5-hydroxymethylfurfural." RSC Advances 6, no. 53 (2016): 47890–96. http://dx.doi.org/10.1039/c6ra00473c.

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16

Liu, Yi, and Francesca M. Kerton. "Mechanistic studies on the formation of 5-hydroxymethylfurfural from the sugars fructose and glucose." Pure and Applied Chemistry 93, no. 4 (March 31, 2021): 463–78. http://dx.doi.org/10.1515/pac-2020-1108.

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Abstract In recent years the transformations of fructose and glucose to the platform chemical 5-hydroxymethylfurfural (5-HMF) have been studied extensively, and a variety of mechanisms have been proposed. This review summarizes the varied mechanisms proposed and methods used to study the dehydration of biomass, such as fructose and glucose, to give 5-hydroxymethylfurfural. For fructose dehydration, two main mechanisms have been suggested including a cyclic and an acyclic pathway, of which the cyclic pathway dominates. The conversion of glucose to 5-HMF can proceed either through initial isomerization to fructose or a direct dehydration. For glucose to fructose isomerization, two main reaction pathways have been proposed (1,2-hydride shift and enolization). This review discusses the mechanisms that have been determined based on the evidence from experiments and/or calculations, and briefly introduces the techniques frequently used in such mechanistic studies. Mechanisms in this field are strongly dependent on the nature of the solvent and the catalyst used, so it is important that researchers have a general idea about the existing mechanisms, and the methods and techniques used for investigation, before pursuing their own mechanistic studies.

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17

Tang, Hao, Ning Li, Fang Chen, Guangyi Li, Aiqin Wang, Yu Cong, Xiaodong Wang, and Tao Zhang. "Highly efficient synthesis of 5-hydroxymethylfurfural with carbohydrates over renewable cyclopentanone-based acidic resin." Green Chemistry 19, no. 8 (2017): 1855–60. http://dx.doi.org/10.1039/c7gc00673j.

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18

Raveendra, G., M. Surendar, and P. S. Sai Prasad. "Selective conversion of fructose to 5-hydroxymethylfurfural over WO3/SnO2 catalysts." New Journal of Chemistry 41, no. 16 (2017): 8520–29. http://dx.doi.org/10.1039/c7nj00725f.

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19

Pawar, Hitesh, and Arvind Lali. "Microwave assisted organocatalytic synthesis of 5-hydroxymethyl furfural in a monophasic green solvent system." RSC Adv. 4, no. 51 (2014): 26714–20. http://dx.doi.org/10.1039/c4ra03137g.

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20

Ruby, Marc-Philipp, and Ferdi Schüth. "Synthesis of N-alkyl-4-vinylpyridinium-based cross-linked polymers and their catalytic performance for the conversion of fructose into 5-hydroxymethylfurfural." Green Chemistry 18, no. 11 (2016): 3422–29. http://dx.doi.org/10.1039/c5gc02949j.

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21

Lu, Ye-Min, Hu Li, Jian He, Yan-Xiu Liu, Zhi-Bing Wu, De-Yu Hu, and Song Yang. "Efficient conversion of glucose to 5-hydroxymethylfurfural using bifunctional partially hydroxylated AlF3." RSC Advances 6, no. 16 (2016): 12782–87. http://dx.doi.org/10.1039/c5ra24013a.

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Mesoporous AlF₃ material bearing both Lewis and Brønsted acid sites exhibits high catalytic performance in glucose-to-fructose isomerization and subsequent dehydration to HMF (57.3% yield).

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22

Zheng, Baohui, Zhijie Fang, Jie Cheng, and Yuhua Jiang. "Microwave-assisted Conversion of Carbohydrates into 5-Hydroxymethylfurfural Catalyzed by ZnCl2." Zeitschrift für Naturforschung B 65, no. 2 (February 1, 2010): 168–72. http://dx.doi.org/10.1515/znb-2010-0212.

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A convenient system for producing 5-hydroxymethylfurfural (HMF) through dehydration of carbohydrates by microwave heating in the presence of ZnCl2 was studied. The use of ZnCl2 gave higher selectivity than other metal salts in the conversion of glucose. With ZnCl2 as catalyst, sucrose could be utilized effectively. Under the conditions of microwave irradiation (300 W, 8 min), HMF yields were 54.6, 55.1, and 80.6% from glucose, fructose and sucrose, whereas upon conventional oil bath heating (0.11 gmL−1 sugar solution, weight ratio of ZnCl2 to substrate = 1 : 4, 189 °C, 60 min) HMF yields from glucose, fructose and sucrose were only up to 37.7, 42.7, and 57.7%, respectively.

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23

Ma, Hao, Zhenzhen Li, Lili Chen, and Junjiang Teng. "LiCl-promoted-dehydration of fructose-based carbohydrates into 5-hydroxymethylfurfural in isopropanol." RSC Advances 11, no. 3 (2021): 1404–10. http://dx.doi.org/10.1039/d0ra08737h.

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24

Körner, Paul, Dennis Jung, and Andrea Kruse. "The effect of different Brønsted acids on the hydrothermal conversion of fructose to HMF." Green Chemistry 20, no. 10 (2018): 2231–41. http://dx.doi.org/10.1039/c8gc00435h.

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The effect of Brønsted acids on the hydrothermal dehydration of fructose to 5-hydroxymethylfurfural (HMF), a promising platform chemical from renewable resources, exceeds the sole donation of catalytically active protons.

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25

Catrinck, Mariana N., Sebastiano Campisi, Paolo Carniti, Reinaldo F. Teófilo, Filippo Bossola, and Antonella Gervasini. "Phosphate Enrichment of Niobium-Based Catalytic Surfaces in Relation to Reactions of Carbohydrate Biomass Conversion: The Case Studies of Inulin Hydrolysis and Fructose Dehydration." Catalysts 11, no. 9 (September 7, 2021): 1077. http://dx.doi.org/10.3390/catal11091077.

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In this work, some physical mixtures of Nb2O5·nH2O and NbOPO4 were prepared to study the role of phosphate groups in the total acidity of samples and in two reactions involving carbohydrate biomass: hydrolysis of polyfructane and dehydration of fructose/glucose to 5-hydroxymethylfurfural (HMF). The acid and catalytic properties of the mixtures were dominated by the phosphate group enrichment. Lewis and Brønsted acid sites were detected by FT-IR experiments with pyridine adsorption/desorption under dry and wet conditions. Lewis acidity decreased with NbP in the composition, while total acidity of the samples, measured by titrations with phenylethylamine in cyclohexane (~3.5 μeq m−2) and water (~2.7 μeq m−2), maintained almost the same values. Inulin conversion took advantage of the presence of surfaces rich in Brønsted sites, and NbOPO4 showed the best hydrolysis activity with glucose/fructose formation. The catalyst with a more phosphated surface showed less deactivation during the dehydration of fructose/glucose into HMF.

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26

Fu, Guangxia, Francisco G. Cirujano, Andraž Krajnc, Gregor Mali, Mickaël Henrion, Simon Smolders, and Dirk E. De Vos. "Unexpected linker-dependent Brønsted acidity in the (Zr)UiO-66 metal organic framework and application to biomass valorization." Catalysis Science & Technology 10, no. 12 (2020): 4002–9. http://dx.doi.org/10.1039/d0cy00638f.

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The functionality of the UiO-66(Zr) linkers affects the number of defects on the Zr6 clusters, leading to differences in the MOFs' Brønsted acidity, which promotes the dehydration of fructose into HMF.

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27

Dai, Jinhang, Liangfang Zhu, Dianyong Tang, Xing Fu, Jinqiang Tang, Xiawei Guo, and Changwei Hu. "Sulfonated polyaniline as a solid organocatalyst for dehydration of fructose into 5-hydroxymethylfurfural." Green Chemistry 19, no. 8 (2017): 1932–39. http://dx.doi.org/10.1039/c6gc03604j.

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Sulfonated polyaniline with mutually reactive sulfonic acid groups and amine/imine represents an organocatalyst for effective production of 5-hydroxymethylfurfural (HMF) from carbohydrates in low-boiling solvents with complete restriction of HMF rehydration.

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Jiao, Lutong, Siyu Sun, Xianling Meng, and Peijun Ji. "Sn-Based Porous Coordination Polymer Synthesized with Two Ligands for Tandem Catalysis Producing 5-Hydroxymethylfurfural." Catalysts 9, no. 9 (August 31, 2019): 739. http://dx.doi.org/10.3390/catal9090739.

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5-Hydroxymethylfurfural (HMF) is a biomass-derived important platform compound. Developing an efficient catalyst for producing HMF from a biomass source is important. Herein, using the ligands 5-sulfoisophthalic acid (SPA) and imidazole (Imd), a tin-based porous coordination polymer was synthesized, namely SPA-Imd-TinPCP. This novel material possesses a multifunctional catalysis capability. The coordinated tin (IV) can catalyze the isomerization of glucose to fructose. The ligand imidazole, as an additional base site, can catalyze glucose isomerization. The sulfonic group of the ligand SPA can catalyze the dehydration of fructose to HMF. SPA-Imd-TinPCP was used as a catalyst for the conversion of glucose to HMF. HMF yields of 59.5% in dimethyl sulfoxide (DMSO) and 49.8% in the biphasic solvent of water/tetrahydrofuran were obtained. Consecutive use of SPA-Imd-TinPCP demonstrated that, after reusing it five times, there was no significant activity loss in terms of the glucose conversion and HMF yield.

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29

Gao, Da-Ming, Bohan Zhao, Haichao Liu, Kei Morisato, Kazuyoshi Kanamori, Zhiyong He, Maomao Zeng, Huaping Wu, Jie Chen, and Kazuki Nakanishi. "Synthesis of a hierarchically porous niobium phosphate monolith by a sol–gel method for fructose dehydration to 5-hydroxymethylfurfural." Catalysis Science & Technology 8, no. 14 (2018): 3675–85. http://dx.doi.org/10.1039/c8cy00803e.

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A new type of niobium phosphate (NbP) with a hierarchically porous structure was synthesised via a sol–gel method accompanied by phase separation and effectively acted as a solid acid for fructose dehydration to HMF.

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30

Cheng, Ziwei, Konstantinos A. Goulas, Natalia Quiroz Rodriguez, Basudeb Saha, and Dionisios G. Vlachos. "Growth kinetics of humins studied via X-ray scattering." Green Chemistry 22, no. 7 (2020): 2301–9. http://dx.doi.org/10.1039/c9gc03961a.

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We use ultra-small-angle X-ray scattering to investigate the evolution of size, morphology, volume fraction and number concentration of humins formed during the Brønsted acid catalyzed dehydration of fructose to 5-hydroxymethylfurfural (HMF).

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31

Songo, Morongwa, Richard Moutloali, and Suprakas Ray. "Development of TiO2-Carbon Composite Acid Catalyst for Dehydration of Fructose to 5-Hydroxymethylfurfural." Catalysts 9, no. 2 (January 31, 2019): 126. http://dx.doi.org/10.3390/catal9020126.

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A TiO2-Carbon (TiO2C) composite was prepared using the microwave-assisted method and sulfonated using fuming sulfuric acid to produce a TiO2C solid acid catalyst. The prepared solid acid catalyst was characterised using scanning electron microscopy, Brunauer-Emmett-Teller analysis, Fourier transform infrared spectroscopy, and X-ray diffraction. Crystallinity analysis confirmed that TiO2C has an anatase structure, while analysis of its morphology showed a combination of spheres and particles with a diameter of 50 nm. The TiO2C solid acid catalyst was tested for use in the catalytic dehydration of fructose to 5-hydroxymethylfurfural (5-HMF). The effect of reaction time, reaction temperature, catalyst dosage, and solvent were investigated against the 5-HMF yield. The 5-HMF yield was found to be 90% under optimum conditions. The solid acid catalyst is very stable and can be reused for four catalytic cycles. Hence, the material has great potential for use in industrial applications and can be used for the direct conversion of fructose to 5-HMF because of its high activity and high reusability.

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Najafi Chermahini, Alireza, Fereshte Shahangi, Hossein A. Dabbagh, and Mohammad Saraji. "Production of 5-hydroxymethylfurfural from fructose using a spherically fibrous KCC-1 silica catalyst." RSC Advances 6, no. 40 (2016): 33804–10. http://dx.doi.org/10.1039/c6ra03382b.

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Fibrous KCC-1 silica nanospheres were synthesized and functionalized with propylsulfonic acid groups and applied as an effectual and reusable catalyst for the production of 5-HMF from the dehydration of fructose using DMSO as a solvent.

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33

Zheng, Rui Yuan, Ning Liu, Wan Yi Liu, Jing Xin Ma, and Bing Li. "Conversion of Fructose to 5-hydroxymethylfurfural Catalyzed by Coaled Carbon-Based Solid Acid." Advanced Materials Research 724-725 (August 2013): 226–30. http://dx.doi.org/10.4028/www.scientific.net/amr.724-725.226.

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Coaled carbon-based solid acid (Coal-SO3H) was prepared by sulfonating ultra-low ash Taixi coal and characterized by XPS, IR and PXRD. It was used as a new, efficient and recyclable catalyst for fructose dehydration to form 5-hydroxymethylfurfural (5-HMF) in dimethyl sulfoxide (DMSO). Reaction time, temperature and catalyst amounts were investigated respectively. The results showed that 81.6 % yield of 5-HMF achieved in dimethyl sulfoxide (DMSO) at 140 °C after 140min using the Coal-SO3H as catalyst. The ash, carbonization temperature and sulfonated way which could influence the catalyst performance for preparing 5-HMF had been investgated.

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34

Tomer, Richa, and Prakash Biswas. "Dehydration of glucose/fructose to 5-hydroxymethylfurfural (5-HMF) over an easily recyclable sulfated titania (SO42−/TiO2) catalyst." New Journal of Chemistry 44, no. 47 (2020): 20734–50. http://dx.doi.org/10.1039/d0nj04151c.

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An efficient SO₄²⁻/TiO₂ catalyst was developed which demonstrated a maximum of ∼75% and ∼37% yield of 5-HMF in the presence of fructose and glucose, respectively. Brønsted/Lewis acidic ratio of catalyst played a crucial role in the yield of 5-HMF.

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35

Saenluang, Kachaporn, Anawat Thivasasith, Pannida Dugkhuntod, Peerapol Pornsetmetakul, Saros Salakhum, Supawadee Namuangruk, and Chularat Wattanakit. "In Situ Synthesis of Sn-Beta Zeolite Nanocrystals for Glucose to Hydroxymethylfurfural (HMF)." Catalysts 10, no. 11 (October 28, 2020): 1249. http://dx.doi.org/10.3390/catal10111249.

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The Sn substituted Beta nanocrystals have been successfully synthesized by in-situ hydrothermal process with the aid of cyclic diquaternary ammonium (CDM) as the structure-directing agent (SDA). This catalyst exhibits a bifunctional catalytic capability for the conversion of glucose to hydroxymethylfurfural (HMF). The incorporated Sn acting as Lewis acid sites can catalyze the isomerization of glucose to fructose. Subsequently, the Brønsted acid function can convert fructose to HMF via dehydration. The effects of Sn amount, zeolite type, reaction time, reaction temperature, and solvent on the catalytic performances of glucose to HMF, were also investigated in the detail. Interestingly, the conversion of glucose and the HMF yield over 0.4 wt% Sn-Beta zeolite nanocrystals using dioxane/water as a solvent at 120 °C for 24 h are 98.4% and 42.0%, respectively. This example illustrates the benefit of the in-situ synthesized Sn-Beta zeolite nanocrystals in the potential application in the field of biomass conversion.

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36

Sebati, Wilhemina, Suprakas Sinha Ray, and Richard Moutloali. "Synthesis of Porous Organic Polymer-Based Solid-Acid Catalysts for 5-Hydroxymethylfurfural Production from Fructose." Catalysts 9, no. 8 (July 31, 2019): 656. http://dx.doi.org/10.3390/catal9080656.

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Herein, we report the synthesis of nanoporous polytriphenylamine polymers (PPTPA) by a simple one-step oxidative polymerization pathway and the materials were sulfonated with chlorosulfonic acid to introduce acidic sulfonic groups to the polymers to form solid acid catalysts (SPPTPA). Magnetic properties were added to SPPTPA catalysts by depositing Fe3O4 nanoparticles to develop (FeSPPTPA) solid acid catalysts, for performing dehydration of fructose to 5-hydroxymethylfurfural (HMF), which is regarded as a sustainable source for liquid fuels and commodity chemicals. XRD, FTIR spectroscopy, SEM, TGA, and N2 sorption techniques were used to characterize synthesized materials. The FeSPPTPA80 nanocatalyst showed superior catalytic activities in comparison to other catalysts due to the nanorods that formed after sulfonation of the PPTPA polymeric material which gave the catalyst enough catalytic centers for dehydration reaction of fructose. The recyclability tests revealed that the magnetic solid acid catalysts could be reused for four consecutive catalytic runs, which made FeSPPTPA a potential nanocatalyst for production of HMF.

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37

Rocha, Sebastián, Teresita Marzialetti, Matías Kopp, and Mara Cea. "Reaction Mechanism of the Microwave-Assisted Synthesis of 5-Hydroxymethylfurfural from Sucrose in Sugar Beet Molasses." Catalysts 11, no. 12 (November 29, 2021): 1458. http://dx.doi.org/10.3390/catal11121458.

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5-hydroxymethylfurfural (HMF) stands out among the chemical products derived from biomass as a building block in the chemical industry. The conventional production of HMF is usually carried out from fructose, glucose, or other monosaccharides as feedstock, but sugar beet molasses, a by-product of the sugar industry containing sucrose (45–55%), is promising. This exploratory study used three aqueous stock solutions and one biphasic system as the sources of sucrose. The dehydration of sucrose to 5-hydroxymethylfurfural was assisted by microwave heating and subcritical water conditions. The maximum yield of HMF was 27.8 mol % for the aqueous solution of synthetic sucrose at 80 min of treatment. Although HMF yield was 7.1 mol % in the aqueous sugar beet molasses solution, it increased 2-fold after clarification (15.1 mol %) and 1.6-fold in the biphasic system (11.4 mol %). These are favorable outcomes since this is an exploratory investigation. The pseudo-first-order model fitted experimental data from the conversion of the sucrose from the stock solutions, and kinetic parameters were estimated and compared. The estimated reaction rate constant showed that inversion of sucrose is faster than fructose dehydration to HMF, but the latter reaction was the rate-determining step only for the biphasic system. The maximum partition coefficient value was four between 40 min and 60 min of reaction, calculated at room temperature. These predictions help investigators to estimate conversions and selectivity when pilot plants need to be simulated.

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38

Hou, Qidong, Weizun Li, Meiting Ju, Le Liu, Yu Chen, and Qian Yang. "One-pot synthesis of sulfonated graphene oxide for efficient conversion of fructose into HMF." RSC Advances 6, no. 106 (2016): 104016–24. http://dx.doi.org/10.1039/c6ra23420h.

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39

Zhang, Qiuyun, Xiaofang Liu, Tingting Yang, Quanlin Pu, Caiyan Yue, Shuya Zhang, and Yutao Zhang. "Catalytic Transfer of Fructose to 5-Hydroxymethylfurfural over Bimetal Oxide Catalysts." International Journal of Chemical Engineering 2019 (April 1, 2019): 1–6. http://dx.doi.org/10.1155/2019/3890298.

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Direct conversion of fructose into 5-hydroxymethylfurfural (HMF) is achieved by using modified aluminum-molybdenum mixed oxide (S-AlMo) as solid acid catalysts. The synthesized catalyst was characterized by powder XRD, nitrogen adsorption-desorption isotherm, NH3-TPD, and SEM. As a result, the presence of strong acidity, mesostructures, and high surface area in the S-AlMo catalyst was confirmed by nitrogen adsorption-desorption isotherm and NH3-TPD studies. A study by optimizing the reaction conditions such as catalyst dosage, reaction temperature, and time has been performed. Under the optimal reaction conditions, HMF was obtained in a high yield of 49.8% by the dehydration of fructose. Moreover, the generality of the catalyst is also demonstrated by glucose and sucrose with moderate yields to HMF (24.9% from glucose; 27.6% from sucrose) again under mild conditions. After the reaction, the S-AlMo catalyst can be easily recovered and reused four times without significant loss of its catalytic activity.

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40

Gavrila, Adina Ionuta, Ioana Asofiei, and Petre Chipurici. "Factorial Design for Optimization of Microwave Assisted Synthesis of 5-Hydroxymethylfurfural." Revista de Chimie 68, no. 4 (May 15, 2017): 639–41. http://dx.doi.org/10.37358/rc.17.4.5521.

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Synthesis of 5-hydroxymethylfurfural (5-HMF) by microwave assisted dehydration of fructose was performed under various operating conditions. A statistical analysis based on a 23 factorial plan was used to optimize the synthesis process. Operating temperature (110, 130 �C), specific mass of HCl catalyst (0.4, 0.6 mg/mgs), and reaction time (8, 12 min) were selected as process factors. A regression equation linking the process performance expressed as 5-HMF yield (7.40-30.60%) to process factors was established. The statistical model emphasized a better performance for higher levels of all process factors.

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Mayer, Sergio Federico, Horacio Falcón, María Teresa Fernández-Díaz, José Miguel Campos-Martín, and José Antonio Alonso. "Structure–properties relationship in the hydronium-containing pyrochlores (H3O)1+pSb1+pTe1−pO6 with catalytic activity in the fructose dehydration reaction." Dalton Transactions 49, no. 33 (2020): 11657–67. http://dx.doi.org/10.1039/d0dt01770a.

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42

Wang, Qiufeng, Jiaqi Hao, and Zhenbo Zhao. "Microwave-Assisted Conversion of Fructose to 5-Hydroxymethylfurfural Using Sulfonated Porous Carbon Derived from Biomass." Australian Journal of Chemistry 71, no. 1 (2018): 24. http://dx.doi.org/10.1071/ch17154.

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In this study, a series of sulfonated carbon solid acid catalysts was prepared by a template method using fructose as the carbon source and zinc chloride as the catalyst and template. The reaction involving fructose dehydration to 5-hydroxymethylfurfural (5-HMF) was investigated using these catalysts with microwave assistance in dimethyl sulfoxide. The influence of different catalysts, catalyst amount, microwave power, fructose content, and reaction temperature, as well as the reusability of the catalyst, were investigated. The prepared catalysts were characterised by X-ray diffraction, FT-IR spectroscopy, scanning electron microscopy, nitrogen adsorption–desorption measurement, and temperature-programmed desorption of ammonia gas, and the total numbers of surface acid sites of these carbon-based solid acid catalysts were analysed by chemical adsorption–desorption of ammonia along with the standard curve for ammonia. The results revealed that the C2-SO3H catalyst exhibited the best activity. A 5-HMF yield of 87 % and fructose conversion of 99 % were achieved at 170°C in DMSO after 3 min. The microwave-assisted synthetic strategy was advantageous compared with the traditional method because this approach could shorten the total reaction time.

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43

Lee, Kyung Won, Jin Ku Cho, Chulhwan Park, and Baek-Jin Kim. "Step-by-Step Hybrid Conversion of Glucose to 5-acetoxymethyl-2-furfural Using Immobilized Enzymes and Cation Exchange Resin." Processes 10, no. 10 (October 14, 2022): 2086. http://dx.doi.org/10.3390/pr10102086.

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An alternative to 5-hydroxymethyl-2-furfural (HMF), which is a promising furan derivative that can be used as a starting material for the preparation of non-petroleum-derived polymeric materials from sugars, is 5-acetoxymethyl-2-furfural (AMF). The less-hydrophilic acetyl group of AMF has advantages over the hydroxy group of HMF in terms of thermal stability and isolation. In previous studies, fructose has been used as a starting material along with lipases for the enzymatic synthesis of AMF. In this study, we designed a hybrid synthesis system that includes the isomerization and esterification of glucose into AMF. For the step-by-step conversion of glucose to 1,6-diacetylfructose (DAF), glucose-isomerase and immobilized lipase (Novozym 435) were used as enzymes. Furthermore, for the synthesis of AMF, the direct dehydration of DAF was performed using a cation exchange resin (Amberlyst 15), combined with several industrial solvents, such as dimethylsulfoxide (DMSO), acetonitrile (AN) and dimethylformamide (DMF) for the synthesis of AMF. In order to improve the final yield of AMF, we determined the best solvent conditions. While the AMF yield after the direct dehydration of DAF in a single solvent was maximum 24%, an AMF and HMF yield in the mixed solvent such as dioxane and DMS (9:1) was achieved each 65% and 15%. According to these results, we found that the addition of dioxane in aprotic polar solvents could affect the dehydration reaction and dramatically improve the formation of AMF and HMF.

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44

Qiu, Guo, Xincheng Wang, Chongpin Huang, Yingxia Li, and Biaohua Chen. "Niobium phosphotungstates: excellent solid acid catalysts for the dehydration of fructose to 5-hydroxymethylfurfural under mild conditions." RSC Advances 8, no. 57 (2018): 32423–33. http://dx.doi.org/10.1039/c8ra05940c.

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45

Villa, A., M. Schiavoni, P. F. Fulvio, S. M. Mahurin, S. Dai, R. T. Mayes, G. M. Veith, and L. Prati. "Phosphorylated mesoporous carbon as effective catalyst for the selective fructose dehydration to HMF." Journal of Energy Chemistry 22, no. 2 (March 2013): 305–11. http://dx.doi.org/10.1016/s2095-4956(13)60037-6.

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46

Toftgaard Pedersen, Asbjørn, Rolf Ringborg, Thomas Grotkjær, Sven Pedersen, and John M. Woodley. "Synthesis of 5-hydroxymethylfurfural (HMF) by acid catalyzed dehydration of glucose–fructose mixtures." Chemical Engineering Journal 273 (August 2015): 455–64. http://dx.doi.org/10.1016/j.cej.2015.03.094.

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47

Yi, Xiaohu, Irina Delidovich, Zhong Sun, Shengtian Wang, Xiaohong Wang, and Regina Palkovits. "A heteropoly acid ionic crystal containing Cr as an active catalyst for dehydration of monosaccharides to produce 5-HMF in water." Catalysis Science & Technology 5, no. 4 (2015): 2496–502. http://dx.doi.org/10.1039/c4cy01555j.

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Cs₂[Cr₃O(OOCC₂H₅)₆(H₂O)₃]₂[α-SiW₁₂O₄₀], a chromium-based heteropoly acid (HPA) ionic crystal, was demonstrated to be an active heterogeneous catalyst for production of 5-hydroxymethylfurfural (HMF) from fructose or glucose.

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48

Gomes, F. N. D. C., L. R. Pereira, N. F. P. Ribeiro, and M. M. V. M. Souza. "PRODUCTION OF 5-HYDROXYMETHYLFURFURAL (HMF) VIA FRUCTOSE DEHYDRATION: EFFECT OF SOLVENT AND SALTING-OUT." Brazilian Journal of Chemical Engineering 32, no. 1 (March 2015): 119–26. http://dx.doi.org/10.1590/0104-6632.20150321s00002914.

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49

Wang, Jiangang, Liwei Zhu, Yong Wang, Hongyou Cui, Yunyun Zhang, and Yuan Zhang. "Fructose dehydration to 5-HMF over three sulfonated carbons: effect of different pore structures." Journal of Chemical Technology & Biotechnology 92, no. 6 (December 20, 2016): 1454–63. http://dx.doi.org/10.1002/jctb.5144.

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50

Zhang, Shuang, Xiaohui Han, Yanjie Liu, Ling Liu, Jiajun Yang, and Long Zhang. "Preparation of acicular mesoporous char sulfonic acid and its application for conversion of fructose to 5-hydroxymethylfurfural." BioResources 16, no. 1 (November 18, 2020): 324–38. http://dx.doi.org/10.15376/biores.16.1.324-338.

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Acicular mesoporous char sulfonic acid was prepared through a one-step method of removing the template at the same time of sulfonation using ethylene tar (ET) as the carbon source and acicular nanometer magnesium hydroxide as the hard template. This method was judged as better than the two-step method of removing the template before sulfonation because it protected the mesoporous structure from damage to a certain extent. When the mass ratio of ET to Mg(OH)2 was 1:3 and carbonization temperature was 550 °C, the catalyst prepared using the one-step method had the highest activity. The obtained catalyst had an amorphous structure with a specific surface area of 446.5 m2/g, an acid density of 4.68 mmol/g, and an average pore diameter of 3.5 nm. When the catalyst was applied in the dehydration of fructose to synthesize 5-hydroxymethylfurfural (5-HMF), 97.5% fructose conversion and 80.1% 5-HMF yield can be obtained. The activity of the catalyst did not decrease after 5 cycles, which indicated that the catalyst had good stability. This research provides a promising strategy for preparation of mesoporous char sulfonic acid and comprehensive utilization of ET.

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