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Production of 5-hydroxymethylfurfural from carbohydrates in a biphasic system

Funds:  Supported by Anhui Natural Science Foundation (1808085QB54),China Postdoctoral Science Foundation (2017M621989), Anhui Province Postdoctoral Science Foundation(2017B216).
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https://doi.org/10.3969/j.issn.0253-2778.2019.04.003
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  • Corresponding author: ZHAO Yan（corresponding author）, male, born in 1985, PhD. Research field:biomass resources.E-mail:yanz@mail.ustc.edu.cn
  • Received Date: 19 December 2017
  • Accepted Date: 06 November 2018
  • Rev Recd Date: 06 November 2018
  • Publish Date: 30 April 2019
    Abstract

  • Abstract

    Cheap catalyst aluminum silicate was combined with HCl to efficiently convert carbohydrates to 5-hydroxymethylfurfural (HMF) in a biphasic system. Glucose can yield 61.5% of 5-HMF in an H2O/n-butanol biphasic system at 453 K within 30 min. Polysaccharides (sucrose, maltose, starch and cellulose) can also be converted to HMF effectively in this biphaisc system at 453 K for 40 min. In addition, aluminum silicate can be reused over five cycles without a significant decrease in its activity. Such catalytic system has the potential to become an effecient and cost-effective approach to the conversion of carbohydrates into bio-fuels and platform chemicals.

    Abstract

    Cheap catalyst aluminum silicate was combined with HCl to efficiently convert carbohydrates to 5-hydroxymethylfurfural (HMF) in a biphasic system. Glucose can yield 61.5% of 5-HMF in an H2O/n-butanol biphasic system at 453 K within 30 min. Polysaccharides (sucrose, maltose, starch and cellulose) can also be converted to HMF effectively in this biphaisc system at 453 K for 40 min. In addition, aluminum silicate can be reused over five cycles without a significant decrease in its activity. Such catalytic system has the potential to become an effecient and cost-effective approach to the conversion of carbohydrates into bio-fuels and platform chemicals.
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    • References(27)
  • [1]
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    [3]
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    [4]
    XU L, ZHANG Y, FU Y. Advances in upgrading lignin pyrolysis vapors by ex situ catalytic fast pyrolysis[J]. Energy Technology, 2017, 5(1): 30-51.
    [5]
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    YANG Y, HU C, ABU-OMARM M. Conversion of glucose into furans in the presence of AlCl3 in an ethanol-water solvent system[J]. Bioresource Technology, 2012, 116: 190-194.
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    QI X, WATANABE M, AIDAT M, et al. Synergistic conversion of glucose into 5-hydroxymethylfurfural in ionic liquid-water mixtures[J]. Bioresource Technology, 2012, 109: 224-228.
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    BERMEJO-DEVAL R, ORAZOV M, GOUNDER R, et al. Active sites in Sn-Beta for glucose isomerization to fructose and epimerization to mannose[J]. ACS Catalysis, 2014, 4(7): 2288-2297.
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    CHOUDHARY V, MUSHRIF S H, HO C, et al. Insights into the interplay of Lewis and Brnsted acid catalysts in glucose and fructose conversion to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media[J]. Journal of the American Chemical Society, 2013, 135(10): 3997-4006.
    [17]
    FENG Y, LI M, GAO Z, et al. Development of betaine-based sustainable catalysts for green conversion of carbohydrates and biomass into 5-hydroxymethylfurfural[J]. ChemSusChem, 2019, 12(2): 495-502.
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    ZHAO H, HOLLADAY J E, BROWNH, et al. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural[J]. Science, 2007, 316(5831): 1597-1600.
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    HU S, ZHANG Z, SONG J, et al. Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid[J]. Green Chemistry, 2009, 11(11): 1746-1749.
    [20]
    SHEN Y, SUN J, YI Y, et al. InCl3-catalyzed conversion of carbohydrates into 5-hydroxymethylfurfural in biphasic system[J]. Bioresource Technology, 2014, 172: 457-460.
    [21]
    NIKOLLA E, ROMN-LESHKOV Y, MOLINERM, et al. “One-pot” synthesis of 5-(hydroxymethyl) furfural from carbohydrates using tin-beta zeolite[J]. Acs Catalysis, 2011, 1(4): 408-410.
    [22]
    TAKAGAKI A, OHARA M, NISHIMURA S, et al. A one-pot reaction for biorefinery: Combination of solid acid and base catalysts for direct production of 5-hydroxymethylfurfural from saccharides[J]. Chemical Communications, 2009 (41): 6276-6278.
    [23]
    DESPAX S, ESTRINE B, HOFFMANNN, et al. Isomerization of D-glucose into D-fructose with a heterogeneous catalyst in organic solvents[J]. Catalysis Communications, 2013, 39: 35-38.
    [24]
    SOUZA R O L, FABIANO D P, FECHE C, et al. Glucose-fructose isomerisation promoted by basic hybrid catalysts[J]. Catalysis Today, 2012, 195(1): 114-119.
    [25]
    ROMN-LESHKOV Y, DUMESIC J A. Solvent effects on fructose dehydration to 5-hydroxymethylfurfural in biphasic systems saturated with inorganic salts[J]. Topics in Catalysis, 2009, 52(3): 297-303.
    [26]
    TSILOMELEKIS G, ORELLA M J, LIN Z, et al. Molecular structure, morphology and growth mechanisms and rates of 5-hydroxymethyl furfural (HMF) derived humins[J]. Green Chemistry, 2016, 18(7): 1983-1993.
    [27]
    TAO F, SONG H, CHOUL. Hydrolysis of cellulose in SO3H-functionalized ionic liquids[J]. Bioresource Technology, 2011, 102(19): 9000-9006.)
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    [1]
    YANG F, LIU Q, YUE M, et al. Tantalum compounds as heterogeneous catalysts for saccharide dehydration to 5-hydroxymethylfurfural[J]. Chemical Communications, 2011, 47(15): 4469-4471.
    [2]
    MA H, LONG J X, WANG F R, et al. Conversion of cellulose to butyl levulinate in bio-butanol medium catalyzed by acidic ionic liquids[J]. Acta Physico-Chimica Sinica, 2015, 31(5): 973-979.
    [3]
    ZHANG Z, ZHAO Z K. Production of 5-hydroxymethylfurfural from glucose catalyzed by hydroxyapatite supported chromium chloride[J]. Bioresource Technology, 2011, 102(4): 3970-3972.
    [4]
    XU L, ZHANG Y, FU Y. Advances in upgrading lignin pyrolysis vapors by ex situ catalytic fast pyrolysis[J]. Energy Technology, 2017, 5(1): 30-51.
    [5]
    GONG Y Y, LIU M, JIA S Y, et al. Production of 5-hydroxymethylfurfural from inulin catalyzed by sulfonated amorphous carbon in an ionic liquid[J]. Acta Physico-Chimica Sinica, 2012, 28(3): 686-692.
    [6]
    CHE P, LU F, ZHANG J, et al. Catalytic selective etherification of hydroxyl groups in 5-hydroxymethylfurfural over H4SiW12O40/MCM-41 nanospheres for liquid fuel production[J]. Bioresource Technology, 2012, 119: 433-436.
    [7]
    PAWAR H S, LALI A M. Polyvinyl alcohol functionalized solid acid catalyst DICAT-1 for microwave-assisted synthesis of 5-hydroxymethylfurfural in green solvent[J]. Energy Technology, 2016, 4(7): 823-834.
    [8]
    SHEN Y, ZHANG Y, CHENY, et al. Combination of Brnsted and Lewis polymeric catalysts for efficient conversion of cellulose into 5-hydroxymethylfurfural (HMF) in ionic liquids[J]. Energy Technology, 2016, 4(5): 600-609.
    [9]
    ROMN-LESHKOV Y, CHHEDA J N, DUMESIC J A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose[J]. Science, 2006, 312(5782): 1933-1937.
    [10]
    YANG Y, HU C, ABU-OMARM M. Conversion of glucose into furans in the presence of AlCl3 in an ethanol-water solvent system[J]. Bioresource Technology, 2012, 116: 190-194.
    [11]
    QI X, WATANABE M, AIDAT M, et al. Synergistic conversion of glucose into 5-hydroxymethylfurfural in ionic liquid-water mixtures[J]. Bioresource Technology, 2012, 109: 224-228.
    [12]
    ZAKRZEWSKA M E, BOGEL-UKASIK E, BOGEL-UKASIKR. Ionic liquid-mediated formation of 5-hydroxymethylfurfural: A promising biomass-derived building block[J]. Chemical Reviews, 2010, 111(2): 397-417.
    [13]
    YANG Y, HU C, ABU-OMARM M. Conversion of carbohydrates and lignocellulosic biomass into 5-hydroxymethylfurfural using AlCl3·6H2O catalyst in a biphasic solvent system[J]. Green Chemistry, 2012, 14(2): 509-513.
    [14]
    VAN PUTTEN R J, VAN DER WAAL J C, DE JONG E D, et al. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources[J]. Chemical Reviews, 2013, 113(3): 1499-1597.
    [15]
    BERMEJO-DEVAL R, ORAZOV M, GOUNDER R, et al. Active sites in Sn-Beta for glucose isomerization to fructose and epimerization to mannose[J]. ACS Catalysis, 2014, 4(7): 2288-2297.
    [16]
    CHOUDHARY V, MUSHRIF S H, HO C, et al. Insights into the interplay of Lewis and Brnsted acid catalysts in glucose and fructose conversion to 5-(hydroxymethyl) furfural and levulinic acid in aqueous media[J]. Journal of the American Chemical Society, 2013, 135(10): 3997-4006.
    [17]
    FENG Y, LI M, GAO Z, et al. Development of betaine-based sustainable catalysts for green conversion of carbohydrates and biomass into 5-hydroxymethylfurfural[J]. ChemSusChem, 2019, 12(2): 495-502.
    [18]
    ZHAO H, HOLLADAY J E, BROWNH, et al. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural[J]. Science, 2007, 316(5831): 1597-1600.
    [19]
    HU S, ZHANG Z, SONG J, et al. Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid[J]. Green Chemistry, 2009, 11(11): 1746-1749.
    [20]
    SHEN Y, SUN J, YI Y, et al. InCl3-catalyzed conversion of carbohydrates into 5-hydroxymethylfurfural in biphasic system[J]. Bioresource Technology, 2014, 172: 457-460.
    [21]
    NIKOLLA E, ROMN-LESHKOV Y, MOLINERM, et al. “One-pot” synthesis of 5-(hydroxymethyl) furfural from carbohydrates using tin-beta zeolite[J]. Acs Catalysis, 2011, 1(4): 408-410.
    [22]
    TAKAGAKI A, OHARA M, NISHIMURA S, et al. A one-pot reaction for biorefinery: Combination of solid acid and base catalysts for direct production of 5-hydroxymethylfurfural from saccharides[J]. Chemical Communications, 2009 (41): 6276-6278.
    [23]
    DESPAX S, ESTRINE B, HOFFMANNN, et al. Isomerization of D-glucose into D-fructose with a heterogeneous catalyst in organic solvents[J]. Catalysis Communications, 2013, 39: 35-38.
    [24]
    SOUZA R O L, FABIANO D P, FECHE C, et al. Glucose-fructose isomerisation promoted by basic hybrid catalysts[J]. Catalysis Today, 2012, 195(1): 114-119.
    [25]
    ROMN-LESHKOV Y, DUMESIC J A. Solvent effects on fructose dehydration to 5-hydroxymethylfurfural in biphasic systems saturated with inorganic salts[J]. Topics in Catalysis, 2009, 52(3): 297-303.
    [26]
    TSILOMELEKIS G, ORELLA M J, LIN Z, et al. Molecular structure, morphology and growth mechanisms and rates of 5-hydroxymethyl furfural (HMF) derived humins[J]. Green Chemistry, 2016, 18(7): 1983-1993.
    [27]
    TAO F, SONG H, CHOUL. Hydrolysis of cellulose in SO3H-functionalized ionic liquids[J]. Bioresource Technology, 2011, 102(19): 9000-9006.)
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