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Abstract
5-Hydroxymethylfurfural (5-HMF) is a versatile platform chemical that can be derived from renewable biomass using homogeneous or heterogeneous acid catalysts. However, efficiently separating and purifying 5-HMF from reaction mixtures remains a critical challenge for its high-value conversion from renewable biomass. To address this challenge, various separation methods have been developed, including distillation, adsorption, liquid-liquid extraction, supercritical carbon dioxide extraction, and integrated separation processes. This review summarizes and discusses recent advancements in the separation and purification of 5-HMF from reaction solutions. It evaluates key parameters such as adsorption capacity, separation selectivity, recovery efficiency, and their influencing factors. The liquid-liquid extraction using biphasic solvents has proven to be a simple, cost-effective, and efficient approach. The ionic liquid extraction, deep eutectic solvent extraction, supercritical carbon dioxide extraction, and integrated separation technologies (e.g., liquid-liquid extraction combined with vacuum distillation, distillation integrated with adsorption) are discussed. This review also provides insight into the mechanisms of different separation methods, which may contribute to the development of new processes for the purification of 5-HMF. This review aims to provide a theoretical basis for the future large-scale, efficient, and economic production of high-purity 5-HMF.
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Keywords
adsorption
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biomass
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liquid-liquid extraction
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5-hydroxymethylfurfural
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supercritical carbon dioxide
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Yanxi Qi, Bingkun Chen, Haixin Guo.
Critical advances in separation and purification of 5-hydroxymethylfurfural.
Front. Chem. Sci. Eng., 2025, 19(8): 71 DOI:10.1007/s11705-025-2582-x
| [1] |
Bozell J J , Petersen G R . Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited. Green Chemistry, 2010, 12(4): 539–554
|
| [2] |
Wang K , Wu M , Zhang Y , Jiang B , Su Y , Yang S , Lu X , Li H . Autogenetic carbon oxyanions enable interfacial OH– deconfinement for reinforced biomass electrooxidation over wide potential window. Advanced Functional Materials, 2025, 35(19): 2424435
|
| [3] |
Chen C , Lv M , Hu H , Huai L , Zhu B , Fan S , Wang Q , Zhang J . 5-Hydroxymethylfurfural and its downstream chemicals: a review of catalytic routes. Advanced Materials, 2024, 36(37): 2311464
|
| [4] |
Chen B , Yang B , Su Y , Hou Q , Smith R L , Qi X , Guo H . NiFeCo wrinkled nanosheet electrode for selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid. Green Chemistry, 2025, 27(7): 2117–2129
|
| [5] |
Qi X , Guo H , Li L , Smith R L Jr . Acid-catalyzed dehydration of fructose into 5-hydroxymethylfurfural by cellulose-derived amorphous carbon. ChemSusChem, 2012, 5(11): 2215–2220
|
| [6] |
Yu I K M , Tsang D C W , Yip A C K , Chen S S , Wang L , Ok Y S , Poon C S . Catalytic valorization of starch-rich food waste into hydroxymethylfurfural (HMF): controlling relative kinetics for high productivity. Bioresource Technology, 2017, 237: 222–230
|
| [7] |
Thanheuser N , Groteguth J T , Leitner W , Esteban J , Vorholt A J . Biphasic production of 5-hydroxymethylfurfural (HMF) in a recyclable deep eutectic solvent-based system catalyzed by H4SiW12O40. ChemSusChem, 2025, 18(3): e202401485
|
| [8] |
Niakan M , Ghamari Kargar P , Maleki B , Zabibah R S , Arab Apoorvari M , Sedigh Ashrafi S , Arghavani S , Zhou S . AgFe2O4@g-C3N4@SO3H nanocomposite: efficient and heterogeneous photocatalyst for the production of 5-hydroxymethylfurfural as a renewable biofuel under visible-light irradiation. Energy & Fuels, 2025, 39(3): 1628–1639
|
| [9] |
Reddy K H P , Lee J , Park Y K . Hydroxymethylfurfural production from cellulosic sugars over supported metal and metal oxide catalysts. Industrial Crops and Products, 2024, 222: 119754
|
| [10] |
Hu L , Qiuyun Z , Pinaki S B , Song Y . Furan-type compounds from carbohydrates via heterogeneous catalysis. Current Organic Chemistry, 2014, 18(5): 547–597
|
| [11] |
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. Chemical Engineering Journal, 2022, 429: 132325
|
| [12] |
Zheng J , He X , Cai C , Xiao J , Liu Y , Chen Z , Pan B , Lin X . Adsorption isotherm, kinetics simulation, and breakthrough analysis of 5-hydroxymethylfurfural adsorption/desorption behavior of a novel polar-modified post-cross-linked poly(divinylbenzene-co-ethyleneglycoldimethacrylate) resin. Chemosphere, 2020, 239: 124732
|
| [13] |
Zheng J , Pan B , Xiao J , He X , Chen Z , Huang Q , Lin X . Experimental and mathematical simulation of noncompetitive and competitive adsorption dynamic of formic acid-levulinic acid-5-hydroxymethylfurfural from single, binary, and ternary systems in a fixed-bed column of SY-01 resin. Industrial & Engineering Chemistry Research, 2018, 57(25): 8518–8528
|
| [14] |
Zuo M , Zheng X , Che W , Wang K , Chen Y , Zeng X . Insight into 5-hydroxymethylfurfural synthesis and separation from the aqueous solvent with ion exchange resin catalysts, mechanisms, and theoretical calculations. Separation and Purification Technology, 2025, 362: 131904
|
| [15] |
Zhao Y , Lu K , Xu H , Zhu L , Wang S . A critical review of recent advances in the production of furfural and 5-hydroxymethylfurfural from lignocellulosic biomass through homogeneous catalytic hydrothermal conversion. Renewable & Sustainable Energy Reviews, 2021, 139: 110706
|
| [16] |
Liang J , Jiang J , Cai T , Liu C , Ye J , Zeng X , Wang K . Advances in selective conversion of carbohydrates into 5-hydroxymethylfurfural. Green Energy & Environment, 2024, 9(9): 1384–1406
|
| [17] |
Sjölin M , Sayed M , Espinoza D , Tallvod S , Al-Rudainy B . Regeneration of dimethyl carbonate and purification of 5-hydroxymethylfurfural used in a biphasic dehydration process through activated carbon adsorption and evaporation. Journal of Environmental Chemical Engineering, 2025, 13(2): 115724
|
| [18] |
Zhao Y , Xu J , Wang J , Wu J , Gao M , Zheng B , Xu H , Shi Q , Dong J . Adsorptive separation of furfural/5-hydroxymethylfurfural in MAF-5 with ellipsoidal pores. Industrial & Engineering Chemistry Research, 2020, 59(25): 11734–11742
|
| [19] |
Soukup-Carne D , Fan X , Esteban J . An overview and analysis of the thermodynamic and kinetic models used in the production of 5-hydroxymethylfurfural and furfural. Chemical Engineering Journal, 2022, 442: 136313
|
| [20] |
Karimi S , Gharouni Fattah S , Li Z , Zuo M , Nasrollahzadeh M , Zeng X . A comparative study of 5-(chloromethyl)furfural and 5-(hydroxymethyl)furfural. Green Chemistry, 2024, 27(2): 379–402
|
| [21] |
Shen T , Hou L , Gosset J , Wang H , Leng S , Boumghar Y , Barghi S , Xu C . Recent advances in processes and technologies for production of 5-hydroxymethylfurfural and 2,5-furandicarboylic acid from carbohydrates. Chemical Engineering Journal, 2024, 500: 156470
|
| [22] |
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. Chemical Reviews, 2013, 113(3): 1499–1597
|
| [23] |
Blumenthal L C , Jens C M , Ulbrich J , Schwering F , Langrehr V , Turek T , Kunz U , Leonhard K , Palkovits R . Systematic identification of solvents optimal for the extraction of 5-hydroxymethylfurfural from aqueous reactive solutions. ACS Sustainable Chemistry & Engineering, 2016, 4(1): 228–235
|
| [24] |
Luo X , Li Y , Gupta N K , Sels B , Ralph J , Shuai L . Protection strategies enable selective conversion of biomass. Angewandte Chemie International Edition, 2020, 59(29): 11704–11716
|
| [25] |
Hu L , Jiang Y , Wu Z , Wang X , He A , Xu J , Xu J . State-of-the-art advances and perspectives in the separation of biomass-derived 5-hydroxymethylfurfural. Journal of Cleaner Production, 2020, 276: 124219
|
| [26] |
Brown D W , Floyd A J , Kinsman R G , Roshanhyphen Y . Dehydration reactions of fructose in non-aqueous media. Journal of Chemical Technology and Biotechnology, 1982, 32(7–12): 920–924
|
| [27] |
Chheda J N , Román-Leshkov Y , Dumesic J A . Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides. Green Chemistry, 2007, 9(4): 342–350
|
| [28] |
Köchermann J , Klemm M . Hydrothermal reactive distillation of biomass and biomass hydrolysates for the recovery and separation of furfural and its byproducts. Industrial & Engineering Chemistry Research, 2023, 62(18): 6886–6896
|
| [29] |
Kawamoto H , Saito S , Hatanaka W , Saka S . Catalytic pyrolysis of cellulose in sulfolane with some acidic catalysts. Journal of Wood Science, 2007, 53(2): 127–133
|
| [30] |
Gomes R F A , Mitrev Y N , Simeonov S P , Afonso C A M . Going beyond the limits of the biorenewable platform: sodium dithionite-promoted stabilization of 5-hydroxymethylfurfural. ChemSusChem, 2018, 11(10): 1612–1616
|
| [31] |
Wei Z , Liu Y , Thushara D , Ren Q . Entrainer-intensified vacuum reactive distillation process for the separation of 5-hydroxylmethylfurfural from the dehydration of carbohydrates catalyzed by a metal salt-ionic liquid. Green Chemistry, 2012, 14(4): 1220–1226
|
| [32] |
Enomoto K , Hosoya T , Miyafuji H . High-yield production of 5-hydroxymethylfurfural from d-fructose, d-glucose, and cellulose by its in situ removal from the reaction system. Cellulose, 2018, 25(4): 2249–2257
|
| [33] |
Hu S , Zhang Z , Zhou Y , Han B , Fan H , Li W , Song J , Xie Y . Conversion of fructose to 5-hydroxymethylfurfural using ionic liquids prepared from renewable materials. Green Chemistry, 2008, 10(12): 1280–1283
|
| [34] |
Motagamwala A H , Huang K , Maravelias C T , Dumesic J A . Solvent system for effective near-term production of hydroxymethylfurfural (HMF) with potential for long-term process improvement. Energy & Environmental Science, 2019, 12(7): 2212–2222
|
| [35] |
Zhao J , Li C , Fan X , Liu H , Liu Z , Zhang J , Sun Z , Chu W . Design and synthesis of Brønsted-Lewis acidic tetraimidazolyl ionic liquids for efficient catalytic conversion of glucose to 5-hydroxymethylfurfural in water/1-octanol. Applied Catalysis A: General, 2023, 649: 118981
|
| [36] |
Liu L , Yang X , Hou Q , Zhang S , Ju M . Corn stalk conversion into 5-hydroxymethylfurfural by modified biochar catalysis in a multi-functional solvent. Journal of Cleaner Production, 2018, 187: 380–389
|
| [37] |
Zhou J , Xia Z , Huang T , Yan P , Xu W , Xu Z , Wang J , Zhang Z C . An ionic liquid-organics-water ternary biphasic system enhances the 5-hydroxymethylfurfural yield in catalytic conversion of glucose at high concentrations. Green Chemistry, 2015, 17(8): 4206–4216
|
| [38] |
Pierrat L , García-Triñanes P . Optimising furfural production from lignocellulosic biomass: feedstock selection, process enhancement, and techno-economic and environmental viability. Chemical Engineering Research & Design, 2024, 212: 261–280
|
| [39] |
Stark A , Ondruschka B , Zaitsau D H , Verevkin S P . Biomass-derived platform chemicals: thermodynamic studies on the extraction of 5-hydroxymethylfurfural from ionic liquids. Journal of Chemical & Engineering Data, 2012, 57(11): 2985–2991
|
| [40] |
Mai Y , Xie K , Liang S , Li G , Song J , Shi C , Song Z , Lin X . Efficient extraction of 5-hydroxymethylfurfural from multicomponents aqueous solution by hydrophobic deep eutectic solvents. Separation and Purification Technology, 2025, 359: 130572
|
| [41] |
Xiong D , Wang Y , Ma H , Lu L , Zhang Q , Shi Y , Zhao Y , Wang J . Temperature-responsive deep eutectic dolvents for highly selective separation of 5-hydroxymethylfurfural from reaction mixture. ACS Sustainable Chemistry & Engineering, 2023, 11(1): 399–406
|
| [42] |
Qin Y Z , Li Y M , Zong M Z , Wu H , Li N . Enzyme-catalyzed selective oxidation of 5-hydroxymethylfurfural (HMF) and separation of HMF and 2,5-diformylfuran using deep eutectic solvents. Green Chemistry, 2015, 17(7): 3718–3722
|
| [43] |
Matsagar B M , Van Nguyen C , Hossain M S A , Islam M T , Yamauchi Y , Dhepe P L , Wu K C W . Glucose isomerization catalyzed by bone char and the selective production of 5-hydroxymethylfurfural in aqueous media. Sustainable Energy & Fuels, 2018, 2(10): 2148–2153
|
| [44] |
Ganji P , Roy S . Trade-off between acidic sites and crystallinity of the WO3-TiO2 catalyst toward dehydration of glucose to 5-hydroxymethylfurfural. Energy & Fuels, 2019, 33(6): 5293–5303
|
| [45] |
Zhang X , Zhang D , Sun Z , Xue L , Wang X , Jiang Z . Highly efficient preparation of HMF from cellulose using temperature-responsive heteropolyacid catalysts in cascade reaction. Applied Catalysis B: Environmental, 2016, 196: 50–56
|
| [46] |
Wang Z , Bhattacharyya S , Vlachos D G . Extraction of furfural and furfural/5-hydroxymethylfurfural from mixed lignocellulosic biomass-derived feedstocks. ACS Sustainable Chemistry & Engineering, 2021, 9(22): 7489–7498
|
| [47] |
Fele Žilnik L , Crnomarkovic M , Novak U , Grilc M , Likozar B . Modelling, optimal solvent screening, and separation of 5-hydroxymethylfurfural or furfural from catalytic conversion reactor stream in downstream purification process. Chemical Engineering Research & Design, 2023, 194: 376–387
|
| [48] |
Baker-Fales M , Chen T Y , Bhalode P , Wang Z , Vlachos D G . Microwave enhancement of extractions and reactions in liquid-liquid biphasic systems. Chemical Engineering Journal, 2023, 476: 146552
|
| [49] |
Wang Z , Bhattacharyya S , Vlachos D G . Solvent selection for biphasic extraction of 5-hydroxymethylfurfural via multiscale modeling and experiments. Green Chemistry, 2020, 22(24): 8699–8712
|
| [50] |
Soukup-Carne D , López-Porfiri P , Bragagnolo F S , Funari C S , Fan X , González-Miquel M , Esteban J . Extraction of 5-hydroxymethylfurfural and furfural in aqueous biphasic systems: a COSMO-RS guided approach to greener solvent selection. ACS Sustainable Chemistry & Engineering, 2024, 12(9): 3766–3779
|
| [51] |
Wang Z , Xia S , Wang X , Fan Y , Zhao K , Wang S , Zhao Z , Zheng A . Catalytic production of 5-hydroxymethylfurfural from lignocellulosic biomass: recent advances, challenges, and opportunities. Renewable & Sustainable Energy Reviews, 2024, 196: 114332
|
| [52] |
Hu Z , Liu B , Zhang Z , Chen L . Conversion of carbohydrates into 5-hydroxymethylfurfural catalyzed by acidic ionic liquids in dimethyl sulfoxide. Industrial Crops and Products, 2013, 50: 264–269
|
| [53] |
Wang J , Ren J , Liu X , Lu G , Wang Y . High yield production and purification of 5-hydroxymethylfurfural. AIChE Journal, 2013, 59(7): 2558–2566
|
| [54] |
Guo H , Ogawa S , Isoda Y , Shen F , Smith R L . Weak-acid biochar catalyst prepared from mechanochemically-activated biomass and humic acid for production of 5-hydroxymethylfurfural. Biochar, 2022, 4(1): 42
|
| [55] |
Zakrzewska M Z , Bogel-Łukasik E , Bogel-Łukasik R . Ionic liquid-mediated formation of 5-hydroxymethylfurfural—a promising biomass-derived building block. Chemical Reviews, 2011, 111(2): 397–417
|
| [56] |
Saha B , Abu-Omar M M . Advances in 5-hydroxymethylfurfural production from biomass in biphasic solvents. Green Chemistry, 2014, 16(1): 24–38
|
| [57] |
Lima S , Neves P , Antunes M M , Pillinger M , Ignatyev N , Valente A A . Conversion of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic liquids. Applied Catalysis A: General, 2009, 363(1): 93–99
|
| [58] |
Yuan B , Guan J , Peng J , Zhu G Z , Jiang J H . Green hydrolysis of corncob cellulose into 5-hydroxymethylfurfural using hydrophobic imidazole ionic liquids with a recyclable, magnetic metalloporphyrin catalyst. Chemical Engineering Journal, 2017, 330: 109–119
|
| [59] |
Lecona-Vargas C S , Orsat V , Dumont M J . Carbohydrate-based biorefineries for the production of 5-hydroxymethylfurfural and 2,5-furandicarboxylic acid and their separation and purification methods. Biomass Conversion and Biorefinery, 2024, 14(21): 26575–26595
|
| [60] |
Chiappe C , Rodriguez Douton M J , Mezzetta A , Pomelli C S , Assanelli G , de Angelis A R . Recycle and extraction: cornerstones for an efficient conversion of cellulose into 5-hydroxymethylfurfural in ionic liquids. ACS Sustainable Chemistry & Engineering, 2017, 5(6): 5529–5536
|
| [61] |
Knierbein M , Voges M , Held C . 5-Hydroxymethylfurfural synthesis in nonaqueous two-phase systems (NTPS)-PC-SAFT predictions and validation. Organic Process Research & Development, 2020, 24(6): 1052–1062
|
| [62] |
Jha S , Sappidi P . Molecular simulations of understanding the structure and separation thermodynamics of 5-hydroxymethylfurfural from 1-butyl-3-methyl imidazolium tetrafluoroborate. Journal of Molecular Liquids, 2023, 391: 123354
|
| [63] |
Wang H , Cui J , Zhao Y , Li Z , Wang J . Highly efficient separation of 5-hydroxymethylfurfural from imidazolium-based ionic liquids. Green Chemistry, 2021, 23(1): 405–411
|
| [64] |
Zhou J , Huang T , Zhao Y , Xia Z , Xu Z , Jia S , Wang J , Zhang Z C . Solvent mediation for enhanced separation of 5-hydroxymethylfurfural from 1-butyl-3-methylimidazolium chloride. Industrial & Engineering Chemistry Research, 2015, 54(32): 7977–7983
|
| [65] |
Wang H , Liu S , Zhao Y , Zhang H , Wang J . Molecular origin for the difficulty in separation of 5-hydroxymethylfurfural from imidazolium based ionic liquids. ACS Sustainable Chemistry & Engineering, 2016, 4(12): 6712–6721
|
| [66] |
Guo H , Duereh A , Hiraga Y , Aida T M , Qi X , Smith R L Jr . Perfect recycle and mechanistic role of hydrogen sulfate ionic liquids as additive in ethanol for efficient conversion of carbohydrates into 5-ethoxymethylfurfural. Chemical Engineering Journal, 2017, 323: 287–294
|
| [67] |
Guo H , Duereh A , Hiraga Y , Qi X , Smith R L Jr . Mechanism of glucose conversion into 5-ethoxymethylfurfural in ethanol with hydrogen sulfate ionic liquid additives and a lewis acid catalyst. Energy & Fuels, 2018, 32(8): 8411–8419
|
| [68] |
Lansalot-Matras C , Moreau C . Dehydration of fructose into 5-hydroxymethylfurfural in the presence of ionic liquids. Catalysis Communications, 2003, 4(10): 517–520
|
| [69] |
Hu S , Zhang Z , Song J , Zhou Y , Han B . Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid. Green Chemistry, 2009, 11(11): 1746–1749
|
| [70] |
Moreau C , Finiels A , Vanoye L . Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst. Journal of Molecular Catalysis A Chemical, 2006, 253(1): 165–169
|
| [71] |
Su Y , Brown H M , Huang X , Zhou X , Amonette J E , Zhang Z C . Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical. Applied Catalysis A: General, 2009, 361(1): 117–122
|
| [72] |
Yong G , Zhang Y , Ying J Y . Efficient catalytic system for the selective production of 5-hydroxymethylfurfural from glucose and fructose. Angewandte Chemie International Edition, 2008, 47(48): 9345–9348
|
| [73] |
Kim J H , Na J G , Yang J W , Chang Y K . Separation of galactose, 5-hydroxymethylfurfural, and levulinic acid in acid hydrolysate of agarose by nanofiltration and electrodialysis. Bioresource Technology, 2013, 140: 64–72
|
| [74] |
Kumalaputri A J , Bottari G , Erne P M , Heeres H J , Barta K . Tunable and selective conversion of 5-HMF to 2,5-furandimethanol and 2,5-dimethylfuran over copper-doped porous metal oxides. ChemSusChem, 2014, 7(8): 2266–2275
|
| [75] |
Xue Z , Ma M G , Li Z , Mu T . Advances in the conversion of glucose and cellulose to 5-hydroxymethylfurfural over heterogeneous catalysts. RSC Advances, 2016, 6(101): 98874–98892
|
| [76] |
Jha S , Sappidi P . Molecular insights of 5-hydroxymethylfurfural in a mixture of ionic liquids and alkylated phenolic solvents. ChemPhysChem, 2024, 25(19): e202400437
|
| [77] |
Jha S , Sappidi P . Structure, dynamic, and free energy analyses of 5-hydroxymethylfurfural in aprotic solvents and imidazolium ionic liquids using all-atom molecular dynamics simulations. Physical Chemistry Chemical Physics, 2024, 26(45): 28417–28430
|
| [78] |
Cui T , Jia S , Zheng Q , Ma Y , Li X . Extractive promotion on the synthesis of 5-hydroxymethylfurfural from highly concentrated saccharides in ionic liquid. ChemistrySelect, 2024, 9(6): e202304019
|
| [79] |
Desir P , Vlachos D G . Intensified reactive extraction for the acid-catalyzed conversion of fructose to 5-hydroxymethylfurfural. Chemical Engineering Journal, 2022, 428: 132556
|
| [80] |
Barroso T L C T , Sganzerla W G , Castro L E N , Freiria N L M , Barbero G F , Lovillo M P , Rostagno M A , Forster-Carneiro T . Removal of 5-hydroxymethylfurfural from brewer’s spent grains hydrolysates obtained by subcritical water hydrolysis: an approach using liquid-liquid extraction. Journal of Supercritical Fluids, 2023, 201: 106004
|
| [81] |
Zhou C , Shen C , Ji K , Yin J , Du L . Efficient production of 5-hydroxymethylfurfural enhanced by liquid-liquid extraction in a membrane dispersion microreactor. ACS Sustainable Chemistry & Engineering, 2018, 6(3): 3992–3999
|
| [82] |
Román-Leshkov Y , Chheda J N , Dumesic J A . Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science, 2006, 312(5782): 1933–1937
|
| [83] |
Yan P , Xia M , Chen S , Han W , Wang H , Zhu W . Unlocking biomass energy: continuous high-yield production of 5-hydroxymethylfurfural in water. Green Chemistry, 2020, 22(16): 5274–5284
|
| [84] |
Sayed M , Warlin N , Hulteberg C , Munslow I , Lundmark S , Pajalic O , Tunå P , Zhang B , Pyo S H , Hatti-Kaul R . 5-Hydroxymethylfurfural from fructose: an efficient continuous process in a water-dimethyl carbonate biphasic system with high yield product recovery. Green Chemistry, 2020, 22(16): 5402–5413
|
| [85] |
Karimi S , Shekaari H . Application of acidic deep eutectic solvents in green extraction of 5-hydroxymethylfurfural. Scientific Reports, 2022, 12(1): 13113
|
| [86] |
Yu X , Li M , Yagoub A E A , Chen L , Zhou C , Yan D . Switchable (pH driven) aqueous two-phase systems formed by deep eutectic solvents as integrated platforms for production-separation 5-HMF. Journal of Molecular Liquids, 2021, 325: 115158
|
| [87] |
Guo H , Qi X . Deep eutectic solvents for synthesis of 5-hydroxymethylfurfural. Current Opinion in Green and Sustainable Chemistry, 2024, 47: 100924
|
| [88] |
Dietz C H J T , Gallucci F , van Sint Annaland M , Held C , Kroon M C . 110th anniversary: distribution coefficients of furfural and 5-hydroxymethylfurfural in hydrophobic deep eutectic solvent + water systems: experiments and perturbed-chain statistical associating fluid theory predictions. Industrial & Engineering Chemistry Research, 2019, 58(10): 4240–4247
|
| [89] |
Zhou J , Sui H , Jia Z , Yang Z , He L , Li X . Recovery and purification of ionic liquids from solutions: a review. RSC Advances, 2018, 8(57): 32832–32864
|
| [90] |
Yu L , Li Z , Huang W , Ali A , Chen Y , Zhao G , Yao S . Recovery and post-treatment processes for ionic liquids and deep eutectic solvents. Journal of Molecular Liquids, 2024, 402: 124767
|
| [91] |
Lee R , Harris J , Champagne P , Jessop P G . CO2-catalysed conversion of carbohydrates to 5-hydroxymethyl furfural. Green Chemistry, 2016, 18(23): 6305–6310
|
| [92] |
Hiraga Y , Ebina K , Su Y , Watanabe M , Oriez V , Camy S . Synthesis/separation of 5-hydroxymethylfurfural converted from fructose promoted by H2O-CO2 biphasic system with solid catalysts: experimental and kinetic modeling approaches. Chemical Engineering Journal, 2024, 485: 149606
|
| [93] |
Lin H , Xiong Q , Zhao Y , Chen J , Wang S . Conversion of carbohydrates into 5-hydroxymethylfurfural in a green reaction system of CO2-water-isopropanol. AIChE Journal, 2017, 63(1): 257–265
|
| [94] |
Wu S , Fan H , Xie Y , Cheng Y , Wang Q , Zhang Z , Han B . Effect of CO2 on conversion of inulin to 5-hydroxymethylfurfural and propylene oxide to 1,2-propanediol in water. Green Chemistry, 2010, 12(7): 1215–1219
|
| [95] |
Liu F , Audemar M , De Oliveira Vigier K , Clacens J M , De Campo F , Jérôme F . Palladium/carbon dioxide cooperative catalysis for the production of diketone derivatives from carbohydrates. ChemSusChem, 2014, 7(8): 2089–2093
|
| [96] |
Shi C , Xin J , Liu X , Lu X , Zhang S . Using sub/supercritical CO2 as “phase separation switch” for the efficient production of 5-hydroxymethylfurfural from fructose in an ionic liquid/organic biphasic system. ACS Sustainable Chemistry & Engineering, 2016, 4(2): 557–563
|
| [97] |
González Prieto M , Fortunatti Montoya M , Hegel P E , Pereda S . Supercritical reactors for the production of advanced bio-fuels: a review. Journal of Supercritical Fluids, 2018, 134: 106–113
|
| [98] |
Jing Y , Hou Y , Wu W , Liu W , Zhang B . Solubility of 5-hydroxymethylfurfural in supercritical carbon dioxide with and without ethanol as cosolvent at 314.1 to 343.2 K. Journal of Chemical & Engineering Data, 2011, 56(2): 298–302
|
| [99] |
González Prieto M , Sánchez F A , Pereda S . Thermodynamic model for biomass processing in pressure intensified technologies. Journal of Supercritical Fluids, 2015, 96: 53–67
|
| [100] |
Park C , Lee J . Recent achievements in CO2-assisted and CO2-catalyzed biomass conversion reactions. Green Chemistry, 2020, 22(9): 2628–2642
|
| [101] |
Motokucho S , Morikawa H , Nakatani H , Noordover B A J . Efficient and environmental-friendly dehydration of fructose to 5-hydroxymethyl-2-furfural in water under high pressure of CO2. Tetrahedron Letters, 2016, 57(42): 4742–4745
|
| [102] |
Oriez V , Labauze H , Benjelloun-Mlayah B , Deleau T , Hiraga Y , Watanabe M , Condoret J S , Camy S . Catalyst-free synthesis of 5-hydroxymethylfurfural from fructose by extractive reaction in supercritical CO2-subcritical H2O two-phase system. Journal of Supercritical Fluids, 2023, 198: 105904
|
| [103] |
Labauze H , Camy S , Floquet P , Benjelloun-Mlayah B , Condoret J S . Kinetic study of 5-hydroxymethylfurfural synthesis from fructose in high pressure CO2-water two-phase system. Industrial & Engineering Chemistry Research, 2019, 58(1): 92–100
|
| [104] |
Sun X , Liu Z , Xue Z , Zhang Y , Mu T . Extraction of 5-HMF from the conversion of glucose in ionic liquid [Bmim]Cl by compressed carbon dioxide. Green Chemistry, 2015, 17(5): 2719–2722
|
| [105] |
Morais A R C , da Costa Lopes A M , Bogel-Łukasik R . Carbon dioxide in biomass processing: contributions to the green biorefinery concept. Chemical Reviews, 2015, 115(1): 3–27
|
| [106] |
Fujii T , Kawasaki S I . Effects of process parameters on vanillin partition coefficient in water-supercritical CO2 extraction. Fluid Phase Equilibria, 2019, 485: 153–157
|
| [107] |
Payne S M , Kerton F M . Solubility of bio-sourced feedstocks in ‘green’ solvents. Green Chemistry, 2010, 12(9): 1648–1653
|
| [108] |
Stagel K , Bica-Schröder K . Flowing forward: continuous synthesis of and with ionic liquids. European Journal of Organic Chemistry, 2024, 27(47): e202400917
|
| [109] |
Li Z , Wang Z , Yang Q , Zhang Z , Yang Y , Ren Q , Xing H . CO2-assisted back-extraction method for ionic liquid biphasic systems. ACS Sustainable Chemistry & Engineering, 2016, 4(8): 4403–4410
|
| [110] |
Vinke P , van Bekkum H . The dehydration of fructose towards 5-hydroxymethylfurfural using activated carbon as adsorbent. Stärke, 1992, 44(3): 90–96
|
| [111] |
Hsiao Y W , Anastasopoulou A , Ierapetritou M , Vlachos D G . Cost and energy efficient cyclic separation of 5-hydroxymethyl furfural from an aqueous solution. Green Chemistry, 2021, 23(11): 4008–4023
|
| [112] |
Guo H , Isoda Y , Honma T , Shen F , Smith R L . Design of functional biocarbons for selective adsorption of 5-hydroxymethylfurfural from aqueous solutions. Colloids and Surface A: Physicochemical and Engineering Aspects, 2022, 637: 128187
|
| [113] |
Jin H , Li Y , Liu X , Ban Y , Peng Y , Jiao W , Yang W . Recovery of HMF from aqueous solution by zeolitic imidazolate frameworks. Chemical Engineering Science, 2015, 124: 170–178
|
| [114] |
Zheng J , Hu L , He X , Liu Y , Zheng X , Tao S , Lin X . Evaluation of pore structure of polarity-controllable post-cross-linked adsorption resins on the adsorption performance of 5-hydroxymethylfurfural in both single- and ternary-component systems. Industrial & Engineering Chemistry Research, 2020, 59(39): 17575–17586
|
| [115] |
Pawar H S . Purification of 5-hydroxymethyl furfural from side products of fructose dehydration reaction in a green solvent. ChemistrySelect, 2020, 5(23): 6851–6855
|
| [116] |
Rajabbeigi N , Ranjan R , Tsapatsis M . Selective adsorption of HMF on porous carbons from fructose/DMSO mixtures. Microporous and Mesoporous Materials, 2012, 158: 253–256
|
| [117] |
Yoo W C , Rajabbeigi N , Mallon E E , Tsapatsis M , Snyder M A . Elucidating structure-properties relations for the design of highly selective carbon-based HMF sorbents. Microporous and Mesoporous Materials, 2014, 184: 72–82
|
| [118] |
Zhang Y B , Luo Q X , Lu M H , Luo D , Liu Z W , Liu Z T . Controllable and scalable synthesis of hollow-structured porous aromatic polymer for selective adsorption and separation of HMF from reaction mixture of fructose dehydration. Chemical Engineering Journal, 2019, 358: 467–479
|
| [119] |
Hu L , Zheng J , Li Q , Tao S , Zheng X , Zhang X , Liu Y , Lin X . Adsorption of 5-hydroxymethylfurfural, levulinic acid, formic acid, and glucose using polymeric resins modified with different functional groups. ACS Omega, 2021, 6(26): 16955–16968
|
| [120] |
Chen X F , Li H L , Ji X R , Shen Z J , Guo H J , Yao S M , Wang M K , Xiong L , Chen X D . Preparation, separation, and purification of 5-hydroxymethylfurfural from sugarcane molasses by a self-synthesized hyper-cross-linked resin. Separation and Purification Technology, 2023, 315: 123661
|
| [121] |
Hu L , Wu Y , Li M , Zhang X , Xian X , Mai Y , Lin X . Highly selective adsorption of 5-hydroxymethylfurfural from multicomponent mixture by simple pH controlled in batch and fixed-bed column studies: competitive isotherms, kinetic, and breakthrough curves simulation. Separation and Purification Technology, 2022, 299: 121756
|
| [122] |
Hu L , Tao S , Xian J , Zhang X , Liu Y , Zheng X , Lin X . Fabricating amide functional group modified hyper-cross-linked adsorption resin with enhanced adsorption and recognition performance for 5-hydroxymethylfurfural adsorption via simple one-step. Chinese Journal of Chemical Engineering, 2022, 43: 230–239
|
| [123] |
León M , Swift T D , Nikolakis V , Vlachos D G . Adsorption of the compounds encountered in monosaccharide dehydration in zeolite beta. Langmuir, 2013, 29(22): 6597–6605
|
| [124] |
Xiong R , León M , Nikolakis V , Sandler S I , Vlachos D G . Adsorption of HMF from water/DMSO solutions onto hydrophobic zeolites: experiment and simulation. ChemSusChem, 2014, 7(1): 236–244
|
| [125] |
Swift T D , Bagia C , Nikolakis V , Vlachos D G , Peklaris G , Dornath P , Fan W . Reactive adsorption for the selective dehydration of sugars to furans: modeling and experiments. AIChE Journal, 2013, 59(9): 3378–3390
|
| [126] |
Hernández B , Vlachos D G , Ierapetritou M G . Coupling process intensification and systems flowsheeting for economic and environmental analysis of 5-hydroxymethyl furfural modular microreactor plants. ACS Sustainable Chemistry & Engineering, 2022, 10(45): 14955–14971
|
| [127] |
Asadi S , Fakhroleslam M , Fatemi S . Cyclic chromatography processes as hybrid systems: dynamic simulation and optimal design for 5-HMF/water separation. Journal of Water Process Engineering, 2025, 69: 106847
|
| [128] |
Tongtummachat T , Thongkan K , Chuphueak W , Jaree A , Akkarawatkhoosith N . Efficient continuous-flow separation and purification processes of 5-hydroxymethylfurfural. Chemical Engineering Journal Advances, 2024, 20: 100641
|
| [129] |
Guo L , Xu X , Wang Q , Park J , Lei H , Zhou L , Wang X . Machine learning-based prediction of heavy metal immobilization rate in the solidification/stabilization of municipal solid waste incineration fly ash (MSWIFA) by geopolymers. Journal of Hazardous Materials, 2024, 467: 133682
|
| [130] |
Zhu L , Fan L , Wang Y , Xiao L , Shen D , Long Y . Machine learning-assisted optimization of 5-hydroxymethylfurfural yield from straw by microwave hydrothermal conversion. Journal of Cleaner Production, 2024, 482: 144234
|
| [131] |
Blank A K B, Bassler P, Piepenbrink M, Lang O, Feldner C. EP Patent, 062121, 2014-12-18
|
| [132] |
Blank J D H B, Son S, Kindler A, Piepenbrink M, Backes R, Feldner C. EP Patent, 064693, 2016-12-29
|
| [133] |
Blank J D H B, Werhan H, Frank J, Kindler A, Piepenbrink M, Backes R, Staal B B P. EP Patent, 061971, 2016-12-29
|
| [134] |
Bastioli L C C, Carotenuto G, Di Martino A, Ferrari A. US Patent, 10030001 B2, 2018-07-24
|
| [135] |
Capuzzi F D L, Carotenuto G. EP Patent, 059538, 2014-11-13
|
| [136] |
Kunz A H B M, Kröner C, Wach W, Grad A-M, Kraus W. EP Patent, 081236, 2018-06-07
|
| [137] |
Kazi F K , Patel A D , Serrano-Ruiz J C , Dumesic J A , Anex R P . Techno-economic analysis of dimethylfuran (DMF) and hydroxymethylfurfural (HMF) production from pure fructose in catalytic processes. Chemical Engineering Journal, 2011, 169(1–3): 329–338
|
| [138] |
Rosenfeld C , Konnerth J , Sailer-Kronlachner W , Solt P , Rosenau T , van Herwijnen H W G . Current situation of the challenging scale-up development of hydroxymethylfurfural production. ChemSusChem, 2020, 13(14): 3544–3564
|
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