Kinetics of high temperature conversion of furfuryl alcohol in water

Milan Hronec; Katarına Fulajtarova; Tomas Sotak

Journal of Industrial and Engineering Chemistry, Vol.20, No.2, 650-655, March, 2014

DOI10.1016/j.jiec.2013.05.029 Export Citation

Kinetics of high temperature conversion of furfuryl alcohol in water

Milan Hronec^†, Katarına Fulajtarova, and Tomas Sotak

Department of Organic Technology, Slovak University of Technology, Radlinske´ho 9, 812 37 Bratislava, Slovakia (Slovak Republic)

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The kinetics of furfuryl alcohol conversion to 4-hydroxycyclopent-2-enone (4-HCP), polymers and levulinic acid (LA) in water was investigated in batch reactors at temperatures 110.200 8C. These acid catalyzed reactions are at high temperatures catalyzed by hydrogen ions formed by autodissociation of water. At temperatures 180-200 ℃ and reaction times 5-10 min more than 50 mol% yields of 4-HCP were achieved. A kinetic model which describes experimental data was developed. The values of the apparent activation energies of the main reaction and the side reactions are very similar, what means that the selectivity of 4-HCP formation is independent on the temperature. It indicates, that is attractive to perform furfuryl alcohol transformation to 4-HCP at high temperatures without changing the selectivity.

Keywords:Furfuryl alcohol;Rearrangement;Hydroxy-cyclopentenone;Kinetics;Levulinic acid

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[2] Gallezot P, Chem. Soc. Rev., 41, 1538 (2012)

[3] Kijenski J, Winiarek P, Paryjczak T, Lewicki A, Mikolajska A, Appl. Catal. A: Gen., 233(1-2), 171 (2002)

[4] Li HX, Luo HS, Zhuang L, Dai WL, Qiao MH, J. Mol. Catal. A-Chem., 203(1-2), 267 (2003)

[5] Merlo AB, Vetere V, Ruggera JF, Casella ML, cata, 10, 1665 (2009)

[6] Choura M, Belgacem NM, Gandini A, Macromolecules, 29(11), 3839 (1996)

[7] Bertarione S, Bonino F, Cesano F, Jain S, Zanetti M, Scarano D, Zecchina A, J. Phys. Chem. B, 113(31), 10571 (2009)

[8] Kim T, Assary RS, Marshall CL, Gosztola DJ, Curtiss LA, Stair PC, ChemCatChem, 3, 1451 (2011)

[9] Krishnan TA, Chanda M, Angew. Makromol. Chem., 43, 145 (1975)

[10] Batista PS, de Souza MF, Polymer, 41(23), 8263 (2000)

[11] Pranger LA, Nunnery GA, Tannenbaum R, Compos. Part B, 43, 1139 (2012)

[12] Hou PX, Orikasa H, Yamazaki T, Matsuoka K, Tomita A, Setoyama N, Fukushima Y, Kyotani T, Chem. Mater., 17, 5187 (2005)

[13] Van de Graaf WD, Lange JP, US Patent 7 265 239 (4.9.2007) to Shell Oil Company. (2007)

[14] Maldonado GMG, Assary RS, Dumesic J, Curtis LA, Energy Environ. Sci., 5, 6981 (2012)

[15] Gong Y, Lin L, Shi J, Liu S, Molecules, 15, 7946 (2010)

[16] Ayoub PM, Lange JP, US Patent Appl. 20100217038 (26.8.2010) to Shell Oil Company. (2010)

[17] Deng L, Zhao Y, Li J, Fu Y, Liao B, Guo QX, ChemSusChem, 3, 1172 (2010)

[18] Horvath I, Mehdi H, Fabos V, Boda L, Mika LT, Gree, 10, 238 (2008)

[19] Lange JP, Van de Graaf WD, Haan RJ, ChemSusChem, 2, 437 (2009)

[20] Al-Shaal MG, Wright WRH, Palkovits R, Green Chem., 14, 1260 (2012)

[21] Bond JQ, Alonso DM, Wang D, West RM, Dumesic JA, Science, 327(5969), 1110 (2010)

[22] Piancatelli G, Scettri A, David G, Auria MD, Tetrahedron, 37, 2775 (1978)

[23] Saito K, Yamachika H, US Patent 4 371 711 (1.2.1983) to Sumitomo Chem. Co. (1983)

[24] Minai M, US Patent 4 970 345 (13.11.1990) to Sumitomo Chem. Co. (1990)

[25] Hronec M, Fulajtarova K, Liptaj T, Appl. Catal. A: Gen., 437-438, 104 (2012)

[26] Cai L, Xiu-yang SL, He L, Xia Wl, Ren QL, J. Inst. Anal., doi:CNKI:SUN:TEST0.2004-06-29 (2004)

[27] Bandura AV, Lvov SN, J. Phys. Chem. Ref Data, 35, 15 (2006)

[28] Zhang Z, Dong K, Zhao ZK, ChemSusChem, 4, 112 (2011)