Synthesis of 5-hydroxymethylfurfural from glucose in a biphasic medium with AlCl₃ and boric acid as the catalyst

References

Amarasekara, A. S., Williams, L. D., & Ebede, C. C. (2008). Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 °C: An NMR study. Carbohydrate Research, 343, 3021–3024. DOI 10.1016/j.carres.2008.09.008.Search in Google Scholar PubMed PubMed Central

Antal, M. J., Mok, W. S. L., & Richards, G. N. (1990). Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose and sucrose. Carbohydrate Research, 199, 91—109. 10.1016/0008-6215(90)84096-d.Search in Google Scholar PubMed

Binder, J. B., & Raines, R. T. (2009). Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. Journal of the American Chemical Society, 131, 1979—1985. 10.1021/ja808537j.Search in Google Scholar PubMed

Boisen, A., Christensen, T. B., Fu, W., Gorbanev, Y. Y., Hansen, T. S., Jensen, J. S., Klitgaard, S. K., Pedersen, S., Riisager, A., Ståhlberg, T., & Woodley, J. M. (2009). Process integration for the conversion of glucose to 2,5-furandicarboxylic acid. Chemical Engineering Research and Design, 87, 1318—1327. 10.1016/j.cherd.2009.06.010.Search in Google Scholar

Cai, C. M., Nagane, N., Kumar, R., & Wyman, C. E. (2014). Coupling metal halides with a co-solvent to produce furfural and 5-HMF at high yields directly from lignocellulosic biomass as an integrated biofuels strategy. Green Chemistry, 16, 3819—3829. 10.1039/c4gc00747f.Search in Google Scholar

Cao, X. Q., Teong, S.P., Wu, D., Yi, G. S., Su, H.B., & Zhang, Y. G. (2015). An enzyme mimic ammonium polymer as a single catalyst for glucose dehydration to 5-hydroxymethylfurfural. Green Chemistry, 17, 2348—2352. 10.1039/c4gc02488e.Search in Google Scholar

Chheda, J. N., Huber, G. W., & Dumesic, J. A. (2007). Liquidphase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angewandte Chemie International Edition, 46, 7164—7183. 10.1002/anie.2006 04274.Search in Google Scholar

Corma, A., Iborra, S., & Velty, A. (2007). Chemical routes for the transformation of biomass into chemicals. Chemical Reviews, 107, 2411—2502. 10.1021/cr050989d.Search in Google Scholar PubMed

Danon, B., Marcotullio, G., & de Jong, W. (2014). Mechanistic and kinetic aspects of pentose dehydration towards furfural in aqueous media employing homogeneous catalysis. Green Chemistry, 16, 39—54. 10.1039/c3gc41351a.Search in Google Scholar

De, S., Dutta, S., & Saha, B. (2011). Microwave assisted conversion of carbohydrates and biopolymers to 5-hydroxymethyl-furfural with aluminium chloride catalyst in water. Green Chemistry, 13, 2859—2868. 10.1039/c1gc15550d.Search in Google Scholar

Deng, T. S., Cui, X. J., Qi, Y. Q., Wang, Y. X., Hou, X. L., & Zhu, Y. L. (2012). Conversion of carbohydrates into 5-hydroxymethylfurfural catalyzed by ZnCl₂ in water. Chemical Communications, 48, 5494—5496. 10.1039/c2cc00122e.Search in Google Scholar PubMed

Fringuelli, F., Pizzo, F., & Vaccaro, L. (2001). Lewis-acid catalyzed organic reactions in water. The case of AlCl₃, TiCl4 and SnCl4 believed to be unusable in aqueous medium. The Journal of Organic Chemistry, 66, 4719–4722. DOI 10.1021/jo010373y.Search in Google Scholar PubMed

Gandini, A., Coelho, D., Gomes, M., Reis, B., & Silvestre, A. (2009). Materials from renewable resources based on furan monomers and furan chemistry: Work in progress. Journal of Materials Chemistry, 19, 8656–8664. DOI 10.1039/b909377j.Search in Google Scholar

Hansen, T. S., Mielby, J., & Riisager, A. (2011). Synergy of boric acid and added salts in the catalytic dehydration of hexoses to 5-hydroxymethylfurfural in water. Green Chemistry, 13, 109–114. DOI 10.1039/c0gc00355g.Search in Google Scholar

Hu, S. Q., Zhang, Z. F., Song, J. L., Zhou, Y. X., & Han, B. X. (2009). Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid. Green Chemistry, 11, 1746–1749. DOI 10.1039/b914601f.Search in Google Scholar

Hu, L., Sun, Y., Lin, L., & Liu, S. J. (2012). 12-Tungstophosphoric acid/boric acid as synergetic catalysts for the conversion of glucose into 5-hydroxymethylfurfural in ionic liquid. Biomass and Bioenergy, 47, 289–294. DOI 10.1016/j.biombioe.2012.09.032.Search in Google Scholar

Huber, G. W., Chheda, J. N., Barrett, C. J., & Dumesic, J. A. (2005). Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science, 308, 1446–1450. DOI 10.1126/science.1111166.Search in Google Scholar PubMed

Jiménez-Morales, I., Teckchandani-Ortiz, A., Santamaría-González, J., Maireles-Torres, P., & Jiménez-López, A. (2014). Selective dehydration of glucose to 5-hydroxymethylfurfural on acidic mesoporous tantalum phosphate. Applied Catalysis B, 144, 22–28. DOI 10.1016/j.apcatb.2013.07.002.Search in Google Scholar

Khokhlova, E. A., Kachala, V. V., & Ananikov V. P. (2012). The first molecular level monitoring of carbohydrate conversion to 5-hydroxymethylfurfural in ionic liquids. B₂O₃-An efficient dual-function metal-free promoter for environmentally benign applications. ChemSusChem, 5, 783–789. DOI 10.1002/cssc.201100670.Search in Google Scholar PubMed

Kuster, B. F. M., & van der Baan, H. S. (1977). The influence of the initial and catalyst concentrations on the dehydration of D-fructose. Carbohydrate Research, 54, 165–176. DOI 10.1016/s0008-6215(00)84806-5.Search in Google Scholar

Kuster, B. M. F. (1990). 5-Hydroxymethylfurfural (HMF). A review focussing on its manufacture. Starch, 42, 314–321. DOI 10.1002/star.19900420808.Search in Google Scholar

Matsumiya, H., & Hara, T. (2015). Conversion of glucose into 5-hydroxymethylfurfural with boric acid in molten mixtures of choline salts and carboxylic acids. Biomass and Bioenergy, 72, 227–232. DOI 10.1016/j.biombioe.2014.11.001.Search in Google Scholar

Moreau, C., Belgacem, M. N., & Gandini, A. (2004). Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers. Topics in Catalysis, 27, 11–30. DOI 10.1023/b:toca.0000013537.13540.0e.Search in Google Scholar

Moreau, C., Finiels, A., & Vanoye, L. (2006). 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, 253, 165–169. DOI 10.1016/j.molcata.2006.03.046.Search in Google Scholar

Olivier-Bourbigou, H., Magna, L., & Morvan, D. (2010). Ionic liquids and catalysis: Recent progress from knowledge to applications. Applied Catalysis A, 373, 1–56. DOI 10.1016/j.apcata.2009.10.008.Search in Google Scholar

Peleteiro, S., da Costa Lopes, A. M., Garrote, G., Parajó, J. C., & Bogel-Łukasik, R. (2015). Simple and efficient furfural production from xylose in media containing 1-butyl-3-methylimidazolium hydrogen sulfate. Industrial & Engineering Chemistry Research, 54, 8368–8373. DOI 10.1021/acs.iecr.5b01771.Search in Google Scholar

Román-Leshkov, Y., Chheda, J. N., & Dumesic, J. A. (2006). Phase modifiers promote efficient production of hydrox ymethylfurfural from fructose. Science, 312, 1933–1937. DOI 10.1126/science.1126337.Search in Google Scholar PubMed

Román-Leshkov, Y., Barrett, C. J., Liu, Z. Y., & Dumesic, J. A. (2007). Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature, 447, 982—985. 10.1038/nature05923.Search in Google Scholar PubMed

Román-Leshkov, Y., & Dumesic, J. A. (2009). Solvent effects on fructose dehydration to 5-hydroxymethylfurfural in biphasic systems saturated with inorganic salts. Topics in Catalysis, 52, 297—303. 10.1007/s11244-008-9166-0.Search in Google Scholar

Rose, I. C., Epstein, N., & Watkinson, A. P. (2000). Acid-catalyzed 2-furaldehyde (furfural). Decomposition kinetics. Industrial & Engineering Chemistry Research, 39, 843—845. 10.1021/ie990550+.Search in Google Scholar

Saha, B., & Abu-Omar, M. M. (2014). Advances in 5-hydroxy-methylfurfural production from biomass in biphasic solvents. Green Chemistry, 16, 24—38. 10.1039/c3gc41324a.Search in Google Scholar

Ståhlberg, T., Sørensen, M. G., & Riisager, A. (2010). Direct conversion of glucose to 5-(hydroxymethyl)furfural in ionic liquids with lanthanide catalysts. Green Chemistry, 12, 321—325. 10.1039/b916354a.Search in Google Scholar

Ståhlberg, T., Rodriguez-Rodriguez, S., Fristrup, P., & Ri-isager, A. (2011). Metal-free dehydration of glucose to 5-(hydroxymethyl)furfural in ionic liquids with boric acid as a promoter. Chemistry - A European Journal, 17, 1456—1464. 10.1002/chem.201002171.Search in Google Scholar PubMed

Tong, X. L., Ma, Y., & Li, Y. D. (2010). Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes. Applied Catalysis A, 385, 1—13. 10.1016/j.apcata.2010.06.049.Search in Google Scholar

Weingarten, R., Tompsett, G. A., Conner, W. C., & Huber, G. W. (2011). Design of solid acid catalysts for aqueous-phase dehydration of carbohydrates: The role of Lewis and Brønsted acid sites. Journal of Catalysis, 279, 174—182. 10.1016/j.jcat.2011.01.013.Search in Google Scholar

Wu, L. Q., Song, J. L., Zhang, B. B., Zhou, B. W., Zhou, H. C., Fan, H. L., Yang, Y. Y., & Han, B. X. (2014). Very efficient conversion of glucose to 5-hydroxymethylfurfural in DBU-based ionic liquids with benzenesulfonate anion. Green Chemistry, 16, 3935—3941. 10.1039/c4gc00311j.Search in Google Scholar

Yang, Y., Hu, C. W., & Abu-Omar, M. M. (2012). Conversion of carbohydrates and lignocellulosic biomass into 5-hydroxymethylfurfural using AlCl₃ ·6H₂O catalyst in a biphasic solvent system. Green Chemistry, 14, 509—513. 10.1039/c1gc15972k.Search in Google Scholar

Yang, Y., Hu, C. W., & Abu-Omar, M. M. (2013). The effect of hydrochloric acid on the conversion of glucose to 5-hydroxymethylfurfural in AlCl₃—H₂O/THF biphasic medium. Journal of Molecular Catalysis A, 376, 98—102. 10.1016/j.molcata.2013.04.016.Search in Google Scholar

Zhang, Z. H., Wang, Q., Xie, H. B., Liu, W. J., & Zhao, Z. B. K. (2011). Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by germanium(IV) chloride in ionic liquids. ChemSusChem, 4, 131—138. 10.1002/cssc.2010 00279.Search in Google Scholar

Zhang, J., Cao, Y., Li, H. Q., & Ma, X. B. (2014). Kinetic studies on chromium-catalyzed conversion of glucose into 5-hydroxymethylfurfural in alkylimidazolium chloride ionic liquid. Chemical Engineering Journal, 237, 55—61. 10.1016/j.cej.2013.10.007.Search in Google Scholar

Zhao, H. B., Holladay, J. E., Brown, H., & Zhang, Z.C. (2007). Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science, 316, 1597—1600. 10.1126/science.1141199.Search in Google Scholar PubMed