Catalytic conversion of fructose into furans using FeCl3 as catalyst

Xuanmu Zhou; Zehui Zhang; Bing Liu; Quan Zhou; Shuguo Wang; Kejian Deng

Journal of Industrial and Engineering Chemistry, Vol.20, No.2, 644-649, March, 2014

DOI10.1016/j.jiec.2013.05.028 Export Citation

Catalytic conversion of fructose into furans using FeCl3 as catalyst

Xuanmu Zhou, Zehui Zhang^†, Bing Liu, Quan Zhou, Shuguo Wang, and Kejian Deng^†

Key Laboratory of Catalysis and Materials Sciences of the State Ethnic Affairs Commission & Ministry of Education, College of Chemistry and Material Science, South-Central University for Nationalities, Wuhan 430074, China

E-mail:,

Conversion of fructose into furan derivates 5-hydroxymethylfurfural (HMF) and 5-ethoxymethylfurfural (EMF) was performed in ethanol-[Bmim]Cl solvent systems, catalyzed by FeCl3. HMF was obtained in a high yield of 90.8% for 4 h at 100 ℃ in 1-butyl-3-methylimidazole chloride ([Bmim]Cl). The ratio of [Bmim]Cl to ethanol showed a remarkable effect on the yields of HMF and EMF. The maximum EMF yield of 30.1% was obtained in a mixed solvent of [Bmim]Cl (0.5 g) and ethanol (4.5 g). On the meanwhile, HMF was obtained in a yield of 60.3%.

Keywords:Fructose;5-Hydroxymethylfurfural;5-Ethoxymethylfurfural;1-Butyl-3-methylimidazole chloride;Ethanol

[References]

Alonso DM, Bond JQ, Dumesic JA, Green Chem., 12, 1493 (2010)
Lee SM, Lee JH, J. Ind. Eng. Chem., 18(1), 16 (2012)
Demiral I, Eryazici A, Sensoz S, Biomass Bioenerg., 36, 43 (2012)
Eom IY, Kim JY, Lee SM, Cho TS, Choi IG, Choi JW, J. Ind. Eng. Chem., 18(6), 2069 (2012)
Daorattanachai P, Namuangruk S, Viriya-empikul N, Laosiripojana N, Faungnawakij K, J. ind, 18(6), 1893 (2012)
Mascal M, Nikitin EB, Angew, 47, 7924 (2008)
Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM, Green Chem., 13, 754 (2011)
Dutta S, De S, Saha B, ChemPlusChem, 77, 259 (2012)
Mascal M, Nikitin EB, ChemSusChem, 2, 859 (2009)
Kraus GA, Guney T, Green Chem., 14, 1593 (2012)
Lew CM, Rajabbeigi N, Tsapatsis M, Ind. Eng. Chem. Res., 51(14), 5364 (2012)
Yang Y, Abu-Omar MM, Hu CW, Appl. En, 99, 80 (2012)
Bing L, Zhang ZH, Deng KJ, Ind. Eng. Chem. Res., 51(47), 15331 (2012)
Wang SG, Zhang ZH, Liu B, Li JL, Catal. Sci. Tech., http://dx.doi.org/10.1039/C3CY00223C. (2013)
Seri K, Inoue Y, Ishida H, Bull. Chem. Soc. Jpn., 74, 1145 (2001)
Wang FF, Shi AW, Qin XX, Liu CL, Dong WS, Carbohydr. Res., 346, 982 (2011)
Ordomsky VV, van der Schaaf J, Schouten JC, Nijhuis TA, J. Cata, 287, 68 (2012)
Akbarian-Feizi L, Mehdipour-Ataei S, Yeganeh H, J. Appl. Polym. Sci., 124(3), 1981 (2012)
Freitas JCR, Couto TR, Paulino AAS, De Freitas JR, Malvestiti I, Oliveira RA, Menezes PH, Tetrahedron, 68, 8645 (2012)
Stahlberg T, Sorensen MG, Riisager A, Gre, 12, 321 (2010)
Zhang ZH, Wang Q, Xie HB, Liu WJ, Zhao ZK, ChemSusChem, 4, 131 (2011)
Zhao H, Holladay JE, Brown H, Zhang ZC, Science, 316, 1597 (2007)
Bolm C, Legros J, Le Paih J, Zani L, Chem. Rev., 104(12), 6217 (2004)
Plictker B, Synlett, 14, 2049 (2010)
Burrell AK, Del Sesto RE, Baker SN, McClesky TM, Baker GA, Gree, 9, 449 (2007)
Lecocq V, Graille A, Santini CC, Baudouin A, Chauvin Y, Basset JM, Arzel L, Bouchu D, Fenet B, New J., 29, 700 (2005)
Roman-Leshkov Y, Chheda JN, Dumesic JA, Science, 312, 1933 (2006)
Wei ZJ, Li Y, Thushara D, Liu YX, Ren QL, J. Taiwan Institute Chem. Eng., 42, 363 (2011)
Zhang ZH, Liu B, Zhao ZK, Starch, 64, 770 (2012)
Mittal N, Nisola GM, Chung WJ, Tetrahedron Lett., 53, 3419 (2012)
Hu SQ, Zhang ZF, Song JL, Zhou YX, Han BX, Gree, 11, 1746 (2009)
Benoit M, Brissonnet Y, Guelou E, Vigier KD, Barrault J, Jerome F, ChemSusChem, 3, 1304 (2010)
Degoede ATJW, Vanrantwijk, Vanbekkum H, Starch, 47, 233 (1995)
Balakrishnan M, Sacia ER, Bell AT, Gree, 14, 1626 (2012)
Che PH, Lu F, Zhang JJ, Huang YZ, Nie X, Gao J, Xu J, Bior, 119, 433 (2012)
Lai LK, Zhang YG, ChemSusChem, 3, 1257 (2010)

[Referenced By]

[1] Alonso DM, Bond JQ, Dumesic JA, Green Chem., 12, 1493 (2010)

[2] Lee SM, Lee JH, J. Ind. Eng. Chem., 18(1), 16 (2012)

[3] Demiral I, Eryazici A, Sensoz S, Biomass Bioenerg., 36, 43 (2012)

[4] Eom IY, Kim JY, Lee SM, Cho TS, Choi IG, Choi JW, J. Ind. Eng. Chem., 18(6), 2069 (2012)

[5] Daorattanachai P, Namuangruk S, Viriya-empikul N, Laosiripojana N, Faungnawakij K, J. ind, 18(6), 1893 (2012)

[6] Mascal M, Nikitin EB, Angew, 47, 7924 (2008)

[7] Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM, Green Chem., 13, 754 (2011)

[8] Dutta S, De S, Saha B, ChemPlusChem, 77, 259 (2012)

[9] Mascal M, Nikitin EB, ChemSusChem, 2, 859 (2009)

[10] Kraus GA, Guney T, Green Chem., 14, 1593 (2012)

[11] Lew CM, Rajabbeigi N, Tsapatsis M, Ind. Eng. Chem. Res., 51(14), 5364 (2012)

[12] Yang Y, Abu-Omar MM, Hu CW, Appl. En, 99, 80 (2012)

[13] Bing L, Zhang ZH, Deng KJ, Ind. Eng. Chem. Res., 51(47), 15331 (2012)

[14] Wang SG, Zhang ZH, Liu B, Li JL, Catal. Sci. Tech., http://dx.doi.org/10.1039/C3CY00223C. (2013)

[15] Seri K, Inoue Y, Ishida H, Bull. Chem. Soc. Jpn., 74, 1145 (2001)

[16] Wang FF, Shi AW, Qin XX, Liu CL, Dong WS, Carbohydr. Res., 346, 982 (2011)

[17] Ordomsky VV, van der Schaaf J, Schouten JC, Nijhuis TA, J. Cata, 287, 68 (2012)

[18] Akbarian-Feizi L, Mehdipour-Ataei S, Yeganeh H, J. Appl. Polym. Sci., 124(3), 1981 (2012)

[19] Freitas JCR, Couto TR, Paulino AAS, De Freitas JR, Malvestiti I, Oliveira RA, Menezes PH, Tetrahedron, 68, 8645 (2012)

[20] Stahlberg T, Sorensen MG, Riisager A, Gre, 12, 321 (2010)

[21] Zhang ZH, Wang Q, Xie HB, Liu WJ, Zhao ZK, ChemSusChem, 4, 131 (2011)

[22] Zhao H, Holladay JE, Brown H, Zhang ZC, Science, 316, 1597 (2007)

[23] Bolm C, Legros J, Le Paih J, Zani L, Chem. Rev., 104(12), 6217 (2004)

[24] Plictker B, Synlett, 14, 2049 (2010)

[25] Burrell AK, Del Sesto RE, Baker SN, McClesky TM, Baker GA, Gree, 9, 449 (2007)

[26] Lecocq V, Graille A, Santini CC, Baudouin A, Chauvin Y, Basset JM, Arzel L, Bouchu D, Fenet B, New J., 29, 700 (2005)

[27] Roman-Leshkov Y, Chheda JN, Dumesic JA, Science, 312, 1933 (2006)

[28] Wei ZJ, Li Y, Thushara D, Liu YX, Ren QL, J. Taiwan Institute Chem. Eng., 42, 363 (2011)

[29] Zhang ZH, Liu B, Zhao ZK, Starch, 64, 770 (2012)

[30] Mittal N, Nisola GM, Chung WJ, Tetrahedron Lett., 53, 3419 (2012)

[31] Hu SQ, Zhang ZF, Song JL, Zhou YX, Han BX, Gree, 11, 1746 (2009)

[32] Benoit M, Brissonnet Y, Guelou E, Vigier KD, Barrault J, Jerome F, ChemSusChem, 3, 1304 (2010)

[33] Degoede ATJW, Vanrantwijk, Vanbekkum H, Starch, 47, 233 (1995)

[34] Balakrishnan M, Sacia ER, Bell AT, Gree, 14, 1626 (2012)

[35] Che PH, Lu F, Zhang JJ, Huang YZ, Nie X, Gao J, Xu J, Bior, 119, 433 (2012)

[36] Lai LK, Zhang YG, ChemSusChem, 3, 1257 (2010)