Abstract
A series of Al exchanged heteropoly tungstate (AlTPA) supported on SnO2 catalysts were prepared and characterized by FT-Infrared, X-ray diffraction and temperature programmed desorption of ammonia. The catalysts were evaluated for dehydration of fructose to 5-hydroxymethylfurfural (5-HMF). The catalysts showed high activity for dehydration of fructose and the catalyst with 20 % AlTPA on SnO2 exhibited highest activity. The high activity of AlTPA catalysts related to the presence of Lewis acidic sites apart from Bronsted acidic sites generated due to presence of Al. The active catalyst was further treated at different temperature to understand the surface-structural variations and thereby their influence on fructose dehydration activity. High temperature calcinations of catalysts leads to destabilization of Keggin unit and resulted a decrease in acidity. The dehydration of fructose activity and selectivity towards 5-HMF product also depends on the reaction temperature, time and catalyst weight.
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Yuriy, R.L., Christopher, J.B., Zhen, Y.L., Dumesic, J.A.: Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 447, 982–985 (2007)
Chheda, J.N., Huber, G.W., Dumesic, J.A.: Liquid-phase catalytic processing of biomass derived oxygenated hydrocarbons to fuels and chemicals. Angew. Chem. Int. Ed. 46, 7164–7183 (2007)
Ragauskas, A.J., Williams, C.K., Davison, B.H., Britovsek, G., Cairney, J., Charles, A.E., Frederick, W.J., Hallett, J.P., Leak, D.J., Liotta, C.L., Mielenz, J.R., Murphy, R., Templer, R., Tschaplinski, T.: The path forward for biofuels and biomaterials. Sci. Rev. 311, 484–489 (2006)
Andreia, A.R., Svilen, P.S., Raquel, F.M.F., Carlos, A.M.A.: 5- Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem. 13, 754–793 (2011)
Małgorzata, E.Z., Ewa, B.Ł., Rafał, B.Ł.: Ionic liquid-mediated formation of 5-hydroxymethylfurfural: a promising biomass-derived building block. Chem. Rev. 111, 397–417 (2011)
Jorgensen, H., Kristensen, J.B., Felby, C.J.: Enzymatic conversion of lignocellulose into fermentable sugars: challenges and opportunities. Biofuels Bioprod. Biorefin. 1, 119–134 (2007)
Luque, R.: Algal biofuels: the eternal promise. Energy Environ. Sci. 3, 254–257 (2010)
Yong, G., Zhang, Y., Ying, J.Y.: Efficient catalytic system for the selective production of 5-hydroxymethylfurfural from glucose and fructose. Angew. Chem. 120, 9485–9488 (2008)
Huber, G.W., Chheda, J.N., Barrett, C.J., Dumesic, J.A.: Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science 308, 1446–1450 (2005)
Qian, X., Nimlos, M.R., Davis, M., Johnson, D.K., Himmel, M.E.: Enzymatic procedures in the preparation of regioprotected d-fructose derivatives. Carbohydr. Res. 340, 319–326 (2005)
van Robert-Jan, P., van der Waal, J.C., de Ed, J., Rasrendra, C.B., Heeres, H.J., de Vries, G.J.: Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem. Rev. 113, 1499–1597 (2013)
Yang, Y., Chang-wei, H., Mahdi, M.A.O.: Conversion of carbohydrates and lignocellulosic biomass into5-hydroxymethylfurfural using AlCl3·6H2O catalyst in a biphasic solvent system. Green Chem. 14, 509–513 (2012)
Hu, S., Zhang, Z., Zhou, Y., Han, B., Fan, H., Li, W., Song, J., Xie, Y.: Aerobic oxidation of benzyl alcohol in supercritical CO2 catalyzed by perruthenate immobilized on polymer supported ionic liquid. Green Chem. 10, 278–283 (2008)
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 Chem. 12, 539–554 (2010)
Leshkov, Y.R., Chheda, J.N., Dumesic, J.A.: Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312, 1933–1937 (2006)
Bicker, M., Kaiser, D., Ott, L., Vogel, H.: Dehydration of d-fructose to hydroxymethylfurfural in sub- and super-critical fluids. J. Supercrit. Fluids 36, 118–126 (2005)
Chheda, J.N., Leshkov, Y.R., Dumesic, J.A.: Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides. Green Chem. 9, 342–350 (2007)
Corma, A., Iborra, S., Velty, A.: Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 107, 2411–2502 (2007)
Zhao, H., Holladay, J.E., Brown, H., Zhang, C.: Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 316, 1597–1600 (2007)
Qi, X., Watanabe, M., Aida, T.M., Smith, R.L.: Sulfated zirconia as a solid acid catalyst for the dehydration of fructose to 5-hydroxymethylfurfural. Catal. Commun. 10, 1771–1775 (2009)
Rana, S., Sujata, M., Dharithrirath, Parida, K.M.: Characterization of novel Cs and K substituted phosphotungstic acid modified MCM-41 catalyst and its catalytic activity towards acetylation of aromatic alcohols. J. Chem. Sci. 124, 1117–1125 (2012)
Rana, S., Sujata, M., Mohapatra, L., Varadwaj, G.B.B., Parida, K.M.: A facile method for synthesis of Keggin-type cesium salt of iron substituted lacunary phosphotungstate supported on MCM-41 and study of its extraordinary catalytic activity. Catal. Today 98, 52–58 (2012)
Rana, S., Parida, K.M.: A simple and efficient protocol using palladium based lacunary phosphotungstate supported mesoporous silica towards hydrogenation of p-nitrophenol to p-aminophenol at room temperature. Catal. Sci. Technol. 2, 979–986 (2012)
Shimizu, K., Uozumi, R., Satsuma, A.: Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods. Catal. Commun. 10, 1849–1853 (2009)
Musau, R.M., Munavu, R.M.: The preparation of 5-hydroxymethyl-2-furaldehyde (HMF) from d-fructose in the presence of DMSO. Biomass 13, 67–74 (1987)
Ramesh Kumar, Ch., Sai Prasad, P.S., Lingaiah, N.: Aluminium exchanged heteropoly tungstate supported on titania catalysts: The generation of Lewis acidity and its role for benzylation reaction. J. Mol. Catal. A 350, 83–90 (2011)
Ahmed, A.I., El-Hakam, A., Abd Elghany, M.A., Abo El-Yazeed, W.S.: Synthesis and characterization of new solid acid catalysts, H3PW12O40 supported on nanoparticle tin oxide: an efficient catalyst for the preparation of 7-hydroxy-4-methylcoumarin. Appl. Catal. A 407, 40–48 (2011)
Ray, S., Gupta, P.S., Singh, G.: Electrical and optical properties of sol-gel prepared pd-doped SnO2 thin films: effect of multiple layers and its use as room temperature methane gas sensor. J. Ovonic Res. 6, 23–34 (2010)
Devassy, M., Lefebvre, F., Halligudi, S.B.: Zirconia-supported 12- tungstophosphoric acid as a solid catalyst for the synthesis of linear alkyl benzenes. J. Catal. 231, 1–10 (2005)
Ramesh Kumar, Ch., Venkateswara Rao, K.T., Sai Prasad, P.S., Lingaiah, N.: Tin exchanged heteropoly tungstate: An efficient catalyst for benzylation of arenes with benzyl alcohol. J. Mol. Catal. A 337, 17–24 (2011)
Cheng, L., Xingtang, Z.X., Bin, L.B., Hongzhe, W.H., Yuncai Li, Y., Yabin, H.Y., Du, Z.: Template synthesis and characterization of WO3/TiO2 composite nanotubes. J. Nanotechnology 16, 1341–1345 (2005)
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The authors GR and MS thank Council of Scientific & Industrial Research (CSIR), New Delhi, India for the award of Senior Research Fellowship. We are thankful to the CSIR for financial support under 12 five year Programme project-CSC-0125.
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Raveendra, G., Srinivas, M., Sai Prasad, P.S. et al. Efficient and selective conversion of fructose to 5-hydroxymethylfurfural over metal exchanged heteropoly tungstate supported on tin oxide catalysts. Int J Adv Eng Sci Appl Math 5, 232–238 (2013). https://doi.org/10.1007/s12572-013-0101-7
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DOI: https://doi.org/10.1007/s12572-013-0101-7