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http://dx.doi.org/10.7464/ksct.2014.20.2.108

Direct Conversion for the Production of 5-HMF from Cellulose over Immobilized Acidic Ionic Liquid Catalyst with Metal Chloride  

Park, Yong Beom (Department of Chemical Engineering, Pukyong National University)
Choi, Jae Hyung (Department of Chemical Engineering, Pukyong National University)
Lim, Han-Kwon (Department of Chemical Systematic Engineering, Catholic University of Daegu)
Woo, Hee-Chul (Department of Chemical Engineering, Pukyong National University)
Publication Information
Clean Technology / v.20, no.2, 2014 , pp. 108-115 More about this Journal
Abstract
Various metal chlorides and acid catalysts in ionic liquid solvent were investigated to directly convert cellulose into 5-hydroxymethylfurfural (5-HMF). Metal chlorides containing Sn(II), Zn(II), Al(III), Fe(III), Cu(II), and Cr(III) were used and acidic ionic liquid immobilized on silica gel as an acid catalyst and commercial acid catalysts (sulfuric acid, chloric acid, Amberlyst-15,DOWEX50x8) were used for comparison studies. The acid strength and amount of acid catalysts were probed with Hammett indicator. The selectivity and yield of 5-HMF were determined with reaction temperature, reaction time and catalyst ratio. A catalyst containing $CrCl_3-6H_2O$ and $SiO_2-[ASBI]HSO_4$ showed the highest selectivity and it was found that this catalyst had higher activity than commercial solid acid catalysts such as Amberlyst-15 and DOWEX50x8. The selectivity of 5-HMF appeared to be mainly dependent on the acid strength and catalyst ratio, it was found that levulinic acid was produced from 5-HMF by rehydration.
Keywords
Cellulose; 5-hydroxymethylfurfural; Ionic liquid; Dehydration;
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Times Cited By KSCI : 1  (Citation Analysis)
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1 Zhang, C., Fu, Z., Liu, Y., Dai, B., Zou, Y., Gong, X., Wang, Y., Deng, W., Wu, H., Xu, Q., Steven, R. K., and Yin, D., "Ionic Liquid-Functionalized Biochar Sulfonic Acid as A Biomimetic Catalyst for Hydrolysis of Cellulose and Bamboo under Microwave Irradiation," Green Chem., 14, 1928-1934 (2012).   DOI   ScienceOn
2 Qi, X., Watanabe, M., Aida, T. M., and Smith, R. L., "Catalytic Conversion of Fructose and Glucose into 5-Hydroxymethylfurfural in Hot Compressed Water by Microwave Heating," Catal. Commun., 9, 2244-2249 (2008).   DOI   ScienceOn
3 Hubber, G. W., Ghheda, J. N., Barrett, C. J., and Dumesic, J. A., "Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates," Science, 308, 1446-1450 (2005).   DOI   ScienceOn
4 Petrus, L., and Noordermeer, M. A., "Biomass to Biofuels, A Chemical Perspective," Green Chem., 8, 861-867 (2006).   DOI   ScienceOn
5 Zakrzewska, M. E., Ewa B. E., and Bogel R., "Ionic Liquid-Mediated Formation of 5-Hydroxymethylfurfural-A Promising Biomass-Derived Building Blok," Chem. Rev., 111, 397-417 (2011).   DOI   ScienceOn
6 Zartman, W. H., and Adkins, H., "Hydrogenolysis of Sugars," J. Am. Chem. Soc., 55, 4559-4563 (1993).
7 Kitano, M., Yamaguchi, D., Suganuma, S., Nakajima, K., Kato, H., Hayashi, S., and Hara, M., "Adsorption-Enhanced Hydrolysis of ${\beta}$-1,4-Glucan on Graphene-Based Amorphous Carbon Bearing $SO_3H$, COOH, and OH Groups," Langmuir, 25, 5068-5075 (2009).   DOI   ScienceOn
8 Silvia M. R., Jose M. C., and Jose L. G., "High Glucose Yields from The Hydrolysis of Cellulose Dissolved in Ionic Liquids," Chem. Eng. J., 181-182, 538-541 (2012).   DOI   ScienceOn
9 Miao, J.-M., Wan, H., Saho, Y.-B., Guan, G.-F., and Xu, B., "Acetalization of Carbonyl Compounds Catalyzed by Acidic Ionic Liquid Immobilized on Silica Gel," J. Molecular Catal. A: Chem., 348, 77-82 (2011).   DOI
10 Miao, J.-M., Wan, H., and Guan, G.-F. "Synthesis of Immobilized Bronsted Acidic Ionic Liquid on Silica Gel as heterogeneous Catalyst for Esterification," Catal. Commun., 12, 353-356 (2012).
11 Feher, C., Krivan, E., Hancsok, J., and Skoda, R.-F., "Oligomerisation of Isobutene with Silica Supported Ionic Liquid Catalysts," Green Chem., 14, 403-409 (2012).   DOI   ScienceOn
12 Ding, Z.-D., Shi, J.-C., Xiao, J.-J., Gu, W.-X., Zheng, C.-G., and Wang, H.-J., "Catalytic Conversion of Cellulose 5-hydroxymethyl Furfural Using Acidic Ionic Liquids and Co-catalyst," Carbohydrate Polym., 90, 792-798 (2012).   DOI   ScienceOn
13 Guan, J., Cao, Q., Guo, X., and Mu, X., "The Mechanism of Glucose Conversion of 5-Hydroxymethylfurfural Catalyzed by Metal Chlorides in Ionic Liquid: A Theoretical Study," Computat. Theoretical Chem., 963, 453-462 (2010).
14 Vasile, I. P., and Christopher, H., "Catalysis in Ionic Liquids," Chem. Rev., 107, 2615-2665 (2007).   DOI   ScienceOn
15 Muruvet Y., Mehmet A., Yalcin, T., and Kadir, Y., "Acidity of Silica-Alumina Catalysts by Amine Titration Using Hammett Indicators and FT-IR Study of Pyridine Adsorption," Turkish J. Chem., 23, 319-327 (1999).
16 Vanoye, L., Fanselow, M., Holbrey, J. D., Atkins, M. P., and Seddon, K. R., "Kinetic Model for The Hydrolysis of Lignocellulosic Biomass in the Ionic Liquid, 1-Ethyl-3-Methyl-Imidazolium Chloride," Green Chem., 11, 390-396 (2009).   DOI   ScienceOn
17 Swatloski, R. P., Spear, S. K., Holbrey, J. D., and Rogers, R. D., "Dissolution of Cellulose with Ionic Liquids," J. Am. Chem. Soc., 12, 4974-4975 (2002).
18 Feng, L., and Chen, Z.-L., "Research Progress on Dissolution and Functional Modification of Cellulose in Ionic Liquids," J. Molecular Liquids, 142, 1-5 (2008).   DOI   ScienceOn
19 Kosan, B., Michels, C., and Meister, F., "Dissolution and Forming of Cellulose with Ionic Liquids," Cellulose, 15, 59-66 (2008).   DOI   ScienceOn
20 Zhao, H., Holladay, J. E., Brown, H., and Zhang, Z. C., "Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural," Science, 316, 1597-1600 (2007).   DOI   ScienceOn
21 Rinaldi, R., and Schijth, F., "Design of Solid Catalysts for the Conversion of Biomass," Energy Environ. Sci., 2, 192-196 (2009).
22 Olusola O. J., Sudip, M., Lamidi, A. U., Kolawole, O. A., Olayinka, O. A., Tolu, O. S., Satanand, S., and Rashmi, C., "Towards the Conversion of Carbohydrate Biomass Feedstocks to Biofuels via Hydroxymethylfurfural," Energy Environ. Sci., 3, 1833-1850 (2010).   DOI   ScienceOn
23 Akien, G. R., Qi, L., and Horvath, I. T., "Molecular Mapping of the Acid Catalysed Dehydration of Fructose," Chem. Commun., 48, 5850-5852 (2012).   DOI   ScienceOn
24 Li, C., Zhang, Z., and Zhao, Z. K., "Direct Conversion of Glucose and Cellulose to 5-Hydroxymethylfurfural in Ionic Liquid under Microwave Irradiation," Tetrahedron Lett., 50, 5403-5405 (2009).   DOI   ScienceOn
25 Su, Y., Brown, H. M., Huang, X., Zhou, X., Amonette, J. E., and Zhang, Z. C., "Single-step Conversion of Cellulose to 5-Hydroxymethylfurfural (HMF), A versatile Platform Chemical," Appl. Catal.. A: General, 361, 117-122 (2009).   DOI   ScienceOn
26 Kim, B. R., Jeong, J. W., Lee, D. H., Kim, S. Y., Yoon, H. J., Lee, Y. S., and Cho, J. K., "Direct Transformation of Cellulose into 5-Hydroxymethyl-2-furfural Using Combination of Metal Chlorides in Imidazolium Ionic Liquid," Green Chem., 13, 1503-1506 (2011).   DOI   ScienceOn
27 Binder, J. B., and Raines, R. T., "Simple Chemical Transformation of Lignocellulosic Biomas into Furans for Fuels and Chemicals," J. Am. Chem. Soc., 131, 1979-1985 (2009).   DOI   ScienceOn
28 Tao, F., Song, H., and Chou, L., "Catalytic Conversion of Cellulose to Chemicals in Ionic Liquid," Carbohydrate Res., 346, 58-63 (2011).   DOI   ScienceOn
29 Choi, J. H., Park, Y. B., Lee, S. H., Cheon, J. K., and Woo, H. C., "The Esterification of Oleic Acid Using Acidic Ionic Liquid Catalysts Immobilized on Silica Gel," Korean Chem. Eng. Res., 48, 583-588 (2010).