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Volumn 273, Issue , 2015, Pages 455-464

Synthesis of 5-hydroxymethylfurfural (HMF) by acid catalyzed dehydration of glucose-fructose mixtures

Author keywords

5 Hydroxymethylfurfural; Acetone; Fructose; Glucose; Kinetics; Reactor configuration

Indexed keywords

ACETONE; CATALYSIS; DEHYDRATION; DIMERS; ENZYME KINETICS; GLUCOSE; KINETIC PARAMETERS; KINETIC THEORY; KINETICS; MIXTURES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 84926435783     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2015.03.094     Document Type: Article
Times cited : (120)

References (47)
  • 2
    • 1842864998 scopus 로고    scopus 로고
    • Carbohydrates as green raw materials for the chemical industry
    • Lichtenthaler F.W., Peters S. Carbohydrates as green raw materials for the chemical industry. Comptes Rendus Chim. 2004, 7:65-90.
    • (2004) Comptes Rendus Chim. , vol.7 , pp. 65-90
    • Lichtenthaler, F.W.1    Peters, S.2
  • 6
    • 49649106060 scopus 로고    scopus 로고
    • Genomics of cellulosic biofuels
    • Rubin E.M. Genomics of cellulosic biofuels. Nature 2008, 454:841-845.
    • (2008) Nature , vol.454 , pp. 841-845
    • Rubin, E.M.1
  • 8
    • 13244288422 scopus 로고    scopus 로고
    • Top Value Added Chemicals from Biomass
    • Volume 1 - Results of Screening for Potential Candidates from Sugars and Synthesis Gas, U.S.D.o. Energy
    • T. Werpy, G. Petersen, Top Value Added Chemicals from Biomass. Volume 1 - Results of Screening for Potential Candidates from Sugars and Synthesis Gas, U.S.D.o. Energy, 2004.
    • (2004)
    • Werpy, T.1    Petersen, G.2
  • 9
    • 77950551360 scopus 로고    scopus 로고
    • Technology development for the production of biobased products form biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited
    • Bozell J.J., Petersen G.R. Technology development for the production of biobased products form biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited. Green Chem. 2010, 12:539.
    • (2010) Green Chem. , vol.12 , pp. 539
    • Bozell, J.J.1    Petersen, G.R.2
  • 10
    • 0142201734 scopus 로고    scopus 로고
    • Dehydration of fructose to 5-hydroxymethylfurfural in sub- and supercritical acetone
    • Bicker M., Hirth J., Vogel H. Dehydration of fructose to 5-hydroxymethylfurfural in sub- and supercritical acetone. Green Chem. 2003, 5:280-284.
    • (2003) Green Chem. , vol.5 , pp. 280-284
    • Bicker, M.1    Hirth, J.2    Vogel, H.3
  • 11
    • 0000585947 scopus 로고
    • Industrial aspects of immobilized glucose isomerase
    • Marcel dekker, INC.
    • S. Pedersen, Industrial aspects of immobilized glucose isomerase, in: Ind. Appl. Immobil. Biocatal., Marcel dekker, INC., 1993, pp. 185-208.
    • (1993) Ind. Appl. Immobil. Biocatal. , pp. 185-208
    • Pedersen, S.1
  • 12
    • 84878622602 scopus 로고    scopus 로고
    • Integrated chemo-enzymatic production of 5-hydroxymethylfurfural from glucose
    • Simeonov S.P., Coelho J.A.S., Afonso C.A.M. Integrated chemo-enzymatic production of 5-hydroxymethylfurfural from glucose. ChemSusChem 2013, 6:997-1000.
    • (2013) ChemSusChem , vol.6 , pp. 997-1000
    • Simeonov, S.P.1    Coelho, J.A.S.2    Afonso, C.A.M.3
  • 13
    • 46449139157 scopus 로고    scopus 로고
    • Catalytical conversion of fructose and glucose into 5-hydroxymethylfurfural in hot compressed water by microwave heating
    • Qi X., Watanabe M., Aida T.M., Smith R.L. Catalytical conversion of fructose and glucose into 5-hydroxymethylfurfural in hot compressed water by microwave heating. Catal. Commun. 2008, 9:2244-2249.
    • (2008) Catal. Commun. , vol.9 , pp. 2244-2249
    • Qi, X.1    Watanabe, M.2    Aida, T.M.3    Smith, R.L.4
  • 14
    • 84989085761 scopus 로고
    • 5-Hydroxymethylfurfural (HMF). A review focusing on its manufacture
    • Kuster B.F.M. 5-Hydroxymethylfurfural (HMF). A review focusing on its manufacture. Starch/Staerke 1990, 42:314-321.
    • (1990) Starch/Staerke , vol.42 , pp. 314-321
    • Kuster, B.F.M.1
  • 15
    • 76249123783 scopus 로고    scopus 로고
    • Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural
    • Huang R., Qi W., Su R., He Z. Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural. Chem. Commun. 2010, 46:1115-1117.
    • (2010) Chem. Commun. , vol.46 , pp. 1115-1117
    • Huang, R.1    Qi, W.2    Su, R.3    He, Z.4
  • 16
    • 84863713762 scopus 로고    scopus 로고
    • Chemo-enzymatic conversion of glucose into 5-hydroxymethylfurfural in seawater
    • Grande P.M., Bergs C., Domínguez de María P. Chemo-enzymatic conversion of glucose into 5-hydroxymethylfurfural in seawater. ChemSusChem. 2012, 5:1203-1206.
    • (2012) ChemSusChem. , vol.5 , pp. 1203-1206
    • Grande, P.M.1    Bergs, C.2    Domínguez de María, P.3
  • 17
    • 84903795111 scopus 로고    scopus 로고
    • Tandem catalytic conversion of glucose to 5-hydroxymethylfurfural with an immobilized enzyme and a solid acid
    • Huang H., Denard C.A., Alamillo R., Crisci A.J., Miao Y., Dumesic J.A., et al. Tandem catalytic conversion of glucose to 5-hydroxymethylfurfural with an immobilized enzyme and a solid acid. ACS Catal. 2014, 4:2165-2168.
    • (2014) ACS Catal. , vol.4 , pp. 2165-2168
    • Huang, H.1    Denard, C.A.2    Alamillo, R.3    Crisci, A.J.4    Miao, Y.5    Dumesic, J.A.6
  • 18
    • 84926477841 scopus 로고
    • Dehydration of d-Fructose, Eindhoven
    • B. Kuster, Dehydration of d-Fructose, Eindhoven, 1975.
    • (1975)
    • Kuster, B.1
  • 19
    • 0023568983 scopus 로고
    • The preparation of 5-hydroxymethyi-2-furaldehyde (HMF) from d-fructose in the presence of DMSO
    • Musau R.M., Munavu, R.M. The preparation of 5-hydroxymethyi-2-furaldehyde (HMF) from d-fructose in the presence of DMSO. Biomass 1987, 13:67-74.
    • (1987) Biomass , vol.13 , pp. 67-74
    • Musau, R.M.1    Munavu, R.M.2
  • 20
    • 26944442004 scopus 로고    scopus 로고
    • Dehydration of d-fructose to hydroxymethylfurfural in sub- and supercritical fluids
    • Bicker M., Kaiser D., Ott L., Vogel H. Dehydration of d-fructose to hydroxymethylfurfural in sub- and supercritical fluids. J. Supercrit. Fluids 2005, 36:118-126.
    • (2005) J. Supercrit. Fluids , vol.36 , pp. 118-126
    • Bicker, M.1    Kaiser, D.2    Ott, L.3    Vogel, H.4
  • 21
    • 84926477840 scopus 로고    scopus 로고
    • Production of 5-hydroxymethylfurfural from fructose using a single-phase mixed aqueous-organic solvent system
    • WO2013/053816 A1
    • J.S. Jensen, T. Grotkjaer, S. Pedersen, R. Ringborg, Production of 5-hydroxymethylfurfural from fructose using a single-phase mixed aqueous-organic solvent system, WO2013/053816 A1, 2013.
    • (2013)
    • Jensen, J.S.1    Grotkjaer, T.2    Pedersen, S.3    Ringborg, R.4
  • 22
    • 37849039002 scopus 로고    scopus 로고
    • Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation
    • Alfonsi K., Colberg J., Dunn P.J., Fevig T., Jennings S., Johnson T.A., et al. Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation. Green Chem. 2008, 10:31.
    • (2008) Green Chem. , vol.10 , pp. 31
    • Alfonsi, K.1    Colberg, J.2    Dunn, P.J.3    Fevig, T.4    Jennings, S.5    Johnson, T.A.6
  • 23
    • 79953823038 scopus 로고    scopus 로고
    • Expanding GSK's solvent selection guide - embedding sustainability into solvent selection starting at medicinal chemistry
    • Henderson R.K., Jiménez-González C., Constable D.J.C., Alston S.R., Inglis G.G.A., Fisher G., et al. Expanding GSK's solvent selection guide - embedding sustainability into solvent selection starting at medicinal chemistry. Green Chem. 2011, 13:854.
    • (2011) Green Chem. , vol.13 , pp. 854
    • Henderson, R.K.1    Jiménez-González, C.2    Constable, D.J.C.3    Alston, S.R.4    Inglis, G.G.A.5    Fisher, G.6
  • 26
    • 84891765168 scopus 로고    scopus 로고
    • Kinetics of homogeneous Brønsted acid-catalyzed fructose dehydration and HMF rehydration: a combined experimental and computational Study
    • Swift T., Bagia C., Choudhary V., Peklaris G., Nikolakis V., Vlachos D.G. Kinetics of homogeneous Brønsted acid-catalyzed fructose dehydration and HMF rehydration: a combined experimental and computational Study. ACS Catal. 2013, 4:259-267.
    • (2013) ACS Catal. , vol.4 , pp. 259-267
    • Swift, T.1    Bagia, C.2    Choudhary, V.3    Peklaris, G.4    Nikolakis, V.5    Vlachos, D.G.6
  • 27
    • 36349033564 scopus 로고    scopus 로고
    • Kinetics of the decomposition of fructose catalyzed by hydrochloric acid in subcritical water: formation of 5-hydroxymethylfurfural, levulinic, and formic acids
    • Asghari F.S., Yoshida H. Kinetics of the decomposition of fructose catalyzed by hydrochloric acid in subcritical water: formation of 5-hydroxymethylfurfural, levulinic, and formic acids. Ind. Eng. Chem. Res. 2007, 46:7703-7710.
    • (2007) Ind. Eng. Chem. Res. , vol.46 , pp. 7703-7710
    • Asghari, F.S.1    Yoshida, H.2
  • 28
    • 33745297371 scopus 로고    scopus 로고
    • Green chemicals: a kinetic study on the conversion of glucose to levulinic acid
    • Girisuta B., Janssen L.P.B.M., Heeres H.J. Green chemicals: a kinetic study on the conversion of glucose to levulinic acid. Chem. Eng. Res. Des. 2006, 85:339-349.
    • (2006) Chem. Eng. Res. Des. , vol.85 , pp. 339-349
    • Girisuta, B.1    Janssen, L.P.B.M.2    Heeres, H.J.3
  • 29
    • 34047182515 scopus 로고
    • The influence of the initial and catalyst concentrations on the dehydration of d-fructose
    • Kuster B., van der Baan H. The influence of the initial and catalyst concentrations on the dehydration of d-fructose. Carbohydr. Res. 1977, 54.
    • (1977) Carbohydr. Res. , vol.54
    • Kuster, B.1    van der Baan, H.2
  • 30
    • 78149428920 scopus 로고    scopus 로고
    • Chloride ions enhance furfural formation from d-xylose in dilute aqueous acidic solutions
    • Marcotullio G., De Jong W. Chloride ions enhance furfural formation from d-xylose in dilute aqueous acidic solutions. Green Chem. 2010, 12:1739.
    • (2010) Green Chem. , vol.12 , pp. 1739
    • Marcotullio, G.1    De Jong, W.2
  • 31
    • 0018490952 scopus 로고
    • A new correlation for saturated densities of liquids and their mixtures
    • Hankinson R.W., Thomson G.H. A new correlation for saturated densities of liquids and their mixtures. AIChE J. 1979, 25:653-663.
    • (1979) AIChE J. , vol.25 , pp. 653-663
    • Hankinson, R.W.1    Thomson, G.H.2
  • 32
    • 0033082586 scopus 로고    scopus 로고
    • A comparison of techniques for the estimation of model prediction uncertainty
    • Omlin M., Reichert P. A comparison of techniques for the estimation of model prediction uncertainty. Ecol. Modell. 1999, 115:45-59.
    • (1999) Ecol. Modell. , vol.115 , pp. 45-59
    • Omlin, M.1    Reichert, P.2
  • 33
    • 0000210269 scopus 로고
    • Salting-out of acetone from water. Basis of a new solvent extraction system
    • Matkovich C.E., Christian G.D. Salting-out of acetone from water. Basis of a new solvent extraction system. Anal. Chem. 1973, 45:1915-1921.
    • (1973) Anal. Chem. , vol.45 , pp. 1915-1921
    • Matkovich, C.E.1    Christian, G.D.2
  • 34
    • 0029487747 scopus 로고
    • Liquid-liquid-solid equilibria of the quaternary system water-ethanol-acetone-sodium chloride at 25°C
    • Marcilla A., Ruiz F., García A. Liquid-liquid-solid equilibria of the quaternary system water-ethanol-acetone-sodium chloride at 25°C. Fluid Phase Equilib. 1995, 112:273-289.
    • (1995) Fluid Phase Equilib. , vol.112 , pp. 273-289
    • Marcilla, A.1    Ruiz, F.2    García, A.3
  • 35
    • 34250835050 scopus 로고    scopus 로고
    • Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates
    • Román-Leshkov Y., Barrett C.J., Liu Z.Y., Dumesic J.A. Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 2007, 447:982-985.
    • (2007) Nature , vol.447 , pp. 982-985
    • Román-Leshkov, Y.1    Barrett, C.J.2    Liu, Z.Y.3    Dumesic, J.A.4
  • 36
    • 0001564145 scopus 로고    scopus 로고
    • Different strategies for selective monoacylation of hexoaldoses in acetone
    • Arcos J.A., Bernabé M., Otero C. Different strategies for selective monoacylation of hexoaldoses in acetone. J. Surfact. Deterg. 1998, 1:345-352.
    • (1998) J. Surfact. Deterg. , vol.1 , pp. 345-352
    • Arcos, J.A.1    Bernabé, M.2    Otero, C.3
  • 37
    • 34047189780 scopus 로고    scopus 로고
    • Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides
    • 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 Chem. 2007, 9:342.
    • (2007) Green Chem. , vol.9 , pp. 342
    • Chheda, J.N.1    Román-Leshkov, Y.2    Dumesic, J.A.3
  • 38
    • 80054936712 scopus 로고    scopus 로고
    • Formation and growth of humins via aldol addition and condensation during acid-catalyzed conversion of 5-hydroxymethylfurfural
    • Patil S., Lund C. Formation and growth of humins via aldol addition and condensation during acid-catalyzed conversion of 5-hydroxymethylfurfural. Energy Fuels 2011, 4745-4755.
    • (2011) Energy Fuels , pp. 4745-4755
    • Patil, S.1    Lund, C.2
  • 39
    • 33745612718 scopus 로고    scopus 로고
    • Phase modifiers promote efficient production of hydroxymethylfurfural from fructose
    • Román-Leshkov Y., Chheda J.N., Dumesic J.A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 312:1933-1937.
    • (2006) Science , vol.312 , pp. 1933-1937
    • Román-Leshkov, Y.1    Chheda, J.N.2    Dumesic, J.A.3
  • 40
    • 84893821822 scopus 로고    scopus 로고
    • Origin of 5-hydroxymethylfurfural stability in water/dimethyl sulfoxide mixtures
    • Tsilomelekis G., Josephson T.R., Nikolakis V., Caratzoulas S. Origin of 5-hydroxymethylfurfural stability in water/dimethyl sulfoxide mixtures. ChemSusChem 2014, 7:117-126.
    • (2014) ChemSusChem , vol.7 , pp. 117-126
    • Tsilomelekis, G.1    Josephson, T.R.2    Nikolakis, V.3    Caratzoulas, S.4
  • 41
    • 0025707819 scopus 로고
    • Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose
    • Antal M., Mok W., Richards G. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose. Carbohydr. Res. 1990, 199:91-109.
    • (1990) Carbohydr. Res. , vol.199 , pp. 91-109
    • Antal, M.1    Mok, W.2    Richards, G.3
  • 42
    • 82555165492 scopus 로고    scopus 로고
    • In situ kinetic study on hydrothermal transformation of d-glucose into 5-hydroxymethylfurfural through d-fructose with 13C NMR
    • Kimura H., Nakahara M., Matubayasi N. In situ kinetic study on hydrothermal transformation of d-glucose into 5-hydroxymethylfurfural through d-fructose with 13C NMR. J. Phys. Chem. A 2011, 115:14013-14021.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 14013-14021
    • Kimura, H.1    Nakahara, M.2    Matubayasi, N.3
  • 43
    • 50449108177 scopus 로고    scopus 로고
    • Isotope labeling studies on the formation of 5-(hydroxymethyl)-2-furaldehyde (HMF) from sucrose by pyrolysis-GC/MS
    • Locas C.P., Yaylayan V. Isotope labeling studies on the formation of 5-(hydroxymethyl)-2-furaldehyde (HMF) from sucrose by pyrolysis-GC/MS. J. Agric. Food Chem. 2008, 56:6717-6723.
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 6717-6723
    • Locas, C.P.1    Yaylayan, V.2
  • 44
    • 84861828799 scopus 로고    scopus 로고
    • 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
    • Pagán-Torres Y.J., Wang T., Gallo J.M.R., Shanks B.H., Dumesic J.A. 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. 2012, 2:930-934.
    • (2012) ACS Catal. , vol.2 , pp. 930-934
    • Pagán-Torres, Y.J.1    Wang, T.2    Gallo, J.M.R.3    Shanks, B.H.4    Dumesic, J.A.5
  • 45
    • 33745230163 scopus 로고    scopus 로고
    • Incremental identification of kinetic models for homogeneous reaction systems
    • Brendel M., Bonvin D., Marquardt W. Incremental identification of kinetic models for homogeneous reaction systems. Chem. Eng. Sci. 2006, 61:5404-5420.
    • (2006) Chem. Eng. Sci. , vol.61 , pp. 5404-5420
    • Brendel, M.1    Bonvin, D.2    Marquardt, W.3
  • 46
    • 22744441977 scopus 로고    scopus 로고
    • Glucose reactions with acid and base catalysts in hot compressed water at 473K
    • Watanabe M., Aizawa Y., Iida T., Aida T.M., Levy C., Sue K., et al. Glucose reactions with acid and base catalysts in hot compressed water at 473K. Carbohydr. Res. 2005, 340:1925-1930.
    • (2005) Carbohydr. Res. , vol.340 , pp. 1925-1930
    • Watanabe, M.1    Aizawa, Y.2    Iida, T.3    Aida, T.M.4    Levy, C.5    Sue, K.6


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