Abstract
5-Hydroxymethyl furfural (HMF) is known as a noteworthy platform in a biorefinery concept. HMF was prepared via fructose dehydration in aqueous and organic media, using three methods, i.e., conventional heating, ultrasonication and microwave irradiation. Water, methyl isobutyl ketone (MIBK), methyl ethyl ketone and ethyl acetate were used as media for HCl-catalyzed synthesis of HMF. FTIR and 1H-NMR spectroscopies were used for analysis. The synthesis yield and selectivity were investigated to optimize variables such as fructose concentration, catalyst dosage, temperature, irradiation power, solvent, and the reaction atmosphere. It was found that the yield in the organic media was superior to that of the aqueous ones. In addition, nitrogen atmosphere favored higher yield than air, due to lack of HMF oxidation. As conclusion, the highest yields of the conventional, ultrasonicated and microwave-assisted reactions were 87, 53, and 38%, respectively. In the reactions ultrasonically promoted, the reaction time scale was highly reduced from hours to minutes. The yield was varied with treatment times, so that ultrasonication was recognized to be the best approach in terms of yield, while the microwave method was the fastest one. Selectivity varied from 60 to 90% depending the reaction media and promotion method.
Similar content being viewed by others
References
R. Van Putten, J. C. Van Der Waal, E. De Jong, C. B. Rasrendra, H. J. Heeres and J. G. De Vries, Chem. Rev., 113, 1499 (2013).
Y.-B. Yi, M.-G. Ha, J.-W. Lee and C.-H. Chung, Korean J. Chem. Eng., 30, 1429 (2013).
S. B. Kim, J. H. Lee, X. Yang, J. Lee and S. W. Kim, Korean J. Chem. Eng., 32, 1 (2015).
A. Mukherjee and V. Raghavan, Biomass and Bioenergy, 72, 143 (2015).
Y. H. Oh, I. Y. Eom, J. C. Joo, J. H. Yu, B. K. Song, S. H. Lee, S. H. Hong and S. J. Park, Korean J. Chem. Eng., 32, 1945 (2015).
A. Gandini, in: K. Loos (Ed.), Biocatalysis in polymer chemistry, Wiley, n.d., pp. 1-34.
G. Mulder, J. Prakt. Chem., 21, 203 (1840).
G. Dull, Chem Zeit, 19, 1003 (1895).
J. Kiermayer, Chem. Appar., 19, 1004 (1895).
D. M. B. Ribeiro, M. Ritter, A. O. Souza, R. Freitag, M. D. Farias, A. F. C. Flores, A. Souto, C. L. Lencina and C. M. P. Pereira, Ultrason. Sonochem., 20, 99 (2013).
I. Agirrezabal-Telleria, I. Gandarias and P. L. Arias, Catal. Today, 234, 42 (2014).
S. P. Teong, G. Yi and Y. Zhang, Green Chem., 16, 2015 (2014).
M. Dashtban, A. Gilbert and P. Fatehi, RSC Adv., 4, 2037 (2014).
L. Atanda, S. Mukundan, A. Shrotri, Q. Ma and J. Beltramini, ChemCatChem, 7, 781 (2015).
A. Jain, A. M. Shore, S. C. Jonnalagadda, K. V. Ramanujachary and A. Mugweru, Appl. Catal. A Gen., 489, 72 (2015).
T. Wang, M. W. Nolte and B. H. Shanks, Green Chem., 16, 548 (2014).
F. A. Rodrigues and R. Guirardello, Chem. Eng. J., 37, 475 (2014).
F. Koopman, N. Wierckx, J. H. de Winde and H. J. Ruijssenaars, Bioresour. Technol., 101, 6291 (2010).
B. Liu, Y. Ren and Z. Zhang, Green Chem., 17, 1610 (2015).
H. Ma, F. Wang, Y. Yu, L. Wang and X. Li, Ind. Eng. Chem. Res., 54, 2657 (2015).
M. Zhang, X. Tong, R. Ma and Y. Li, Catal. Today, 6 (2015).
R. Noma, K. Nakajima, K. Kamata, M. Kitano, S. Hayashi and M. Hara, J. Phys. Chem. C, 119, 17117 (2015).
B. F. M. Kuster, 42, 314 (1990).
T. S. Hansen, J. M. Woodley and A. Riisager, Carbohydr. Res., 344, 2568 (2009).
T. J. Christian, M. Manley-Harris, R. J. Field and B. A. Parker, J. Agric. Food Chem., 48, 1823 (2000).
D. A. Kotadia and S. S. Soni, Catal. Sci. Technol., 3, 469 (2013).
L. Hu, G. Zhao, X. Tang, Z. Wu, J. Xu, L. Lin and S. Liu, Bioresour. Technol., 148, 501 (2013).
L. Zhou, Y. He, Z. Ma, R. Liang, T. Wu and Y. Wu, Carbohydr. Polym., 117, 694 (2015).
J.-A. Chun, J.-W. Lee, Y.-B. Yi, S.-S. Hong and C.-H. Chung, Korean J. Chem. Eng., 27, 930 (2010).
S. Wang, Y. Du, P. Zhang, X. Cheng and Y. Qu, Korean J. Chem. Eng., 31, 2286 (2014).
S. Wang, Y. Du, W. Zhang, X. Cheng and J. Wang, Korean J. Chem. Eng., 31, 1786 (2014).
N. A. S. Ramli and N. A. S. Amin, J. Mol. Catal. A Chem., 407, 113 (2015).
D. W. Brown, A. J. Floyd, R. G. Kinsman and Y. Ali, J. Chem. Technol. Biotechnol., 32, 920 (1982).
X. Qi, H. Guo, L. Li and R. L. Smith, ChemSusChem, 5, 2215 (2012).
J. Zhang and E. Weitz, ACS Catal., 2, 1211 (2012).
V. da Silva Lacerda, J. B. López-Sotelo, A. Correa-Guimarães, S. Hernández-Navarro, M. Sánchez-Bascones, L. M. Navas-Gracia, P. Martín-Ramos, E. Pérez-Lebeña and J. Martín-Gil, Bioresour. Technol., 180, 88 (2015).
X. Qi, M. Watanabe, T. Aida and R. L. Smith, Green Chem., 11, 1327 (2009).
F. Guo, Z. Fang and T. J. Zhou, Bioresour. Technol., 112, 313 (2012).
X. Zhou, Z. Zhang, B. Liu, Z. Xu and K. Deng, Carbohydr. Res., 375, 68 (2013).
B. Saha and M. M. Abu-omar, Green Chem., 16, 24 (2014).
Y. Román-Leshkov and J. A. Dumesic, Top. Catal., 52, 297 (2009).
L. J. Lorenz, Modern Methods of Pharmaceutical Analysis, Second Ed., CRC Press, Florida (2000).
X. Tong and Y. Li, ChemSusChem, 3, 350 (2010).
N. Jiang, W. Qi, R. Huang, M. Wang and Z. He, J. Chem. Technol. Biotechnol., 89, 56 (2013).
B. Klinpratoom, A. Ontanee and C. Ruangviriyachai, Korean J. Chem. Eng., 32, 413 (2015).
H. E. Van Dam, Starch, 38, 95 (1986).
F. Wang, H.-Z. Wu, C.-L. Liu, R.-Z. Yang and W.-S. Dong, Carbohydr. Res., 368, 78 (2013).
K. Gollnick and A. Griesbeck, Tetrahedron, 41, 2057 (1985).
G. C. M. Lee, E. T. Syage, D. Harcourt, J. M. Holmes and M. E. Garst, J. Org. Chem., 56, 7007 (1991).
T. Montagnon, M. Tofi and G. Vassilikogiannakis, Acc. Chem. Res., 41, 1001 (2008).
M. J. Antal, W. S. L. Mok and G. N. Richards, Carbohydr. Res., 199, 91 (1990).
Y. Li, H. Liu, C. Song, X. Gu, H. Li, W. Zhu, S. Yin and C. Han, Bioresour. Technol., 133, 347 (2013).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Esmaeili, N., Zohuriaan-Mehr, M.J., Bouhendi, H. et al. HMF synthesis in aqueous and organic media under ultrasonication, microwave irradiation and conventional heating. Korean J. Chem. Eng. 33, 1964–1970 (2016). https://doi.org/10.1007/s11814-016-0031-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-016-0031-8