Abstract
The liquid-phase oligomer/polymerization of furfuryl alcohol (FA) catalyzed by homogeneous and heterogeneous acid catalysts was investigated by Infrared (IR) spectroscopy. At room temperature and 100 °C, FA was not decomposed with metal oxide catalysts except for tungsten oxide, whereas amberlyst and sulfuric acid converted a furfuryl alcohol monomer into oligomer/polymer even at a room temperature. During FA oligomer/polymerization reaction, a strong C=O band observed in the IR spectra provided a diketone structure, which was not observed in the Raman spectroscopy. Based on the FA monomer color changings and IR spectra, tungsten oxide can be possibly applied as a heterogeneous catalyst for controlling the product distribution and avoiding a product separation issue from catalyst.
Article PDF
Avoid common mistakes on your manuscript.
References
G.W. Huber, J. N. Chheda, C. J. Barrett and J. A. Dumesic, Science, 308, 1446 (2005).
N. Shi, Q. Liu, Q. Zhang, T. Wang and L. Ma, Green Chem., 15, 1967 (2013).
T. Kim, R. S. Assary, C. L. Marshall, D. J. Gosztola, L. A. Curtiss and P. C. Stair, ChemCatChem., 3, 1451 (2011).
T. Werpy and G. Petersen, Top Value Added Chemicals from Biomass, US Department of Energy, Office of Scientific and Technical Information, Oak Ridge, TN, 2004, No. DOE/GO-102004-1992, http://www.nrel.gov/docs/fy04osti/35523.pdf.
J. J. Bozell and G. R. Peterson, Green Chem., 12, 539 (2010).
G. M.G. Maldonado, R. S. Assary, J. Dumesic and L. A. Curtiss, Energy Environ. Sci., 5, 6981 (2012).
S. K. R. Patil and C. R. F. Lund, Energy Fuels, 25, 4745 (2011).
S. K. R. Patil, J. Heltzel and C. R. F. Lund, Energy Fuels, 26, 5281 (2012).
L. Radhakrishnan, J. Reboul, S. Furukawa, P. Srinivasu, S. Kitagawa and Y. Yamauchi, Chem. Mater., 23, 1225 (2011).
I. S. Park, M. Choi, T.W. Kim and R. Ryoo, J. Mater. Chem., 16, 3409 (2006).
B. Yi, R. Rajagopalan, H. C. Foley, U. J. Kim, X. Liu and P. C. Eklund, J. Am. Chem. Soc., 128, 11307 (2006).
X. H. Men, Z. Z. Zhang, H. J. Song, K. Wang and W. Jiang, Comp. Sci. Technol., 68, 1042 (2008).
J. Yao, H. Wang, J. Liu, K.Y. Chan, L. Zhang and N. Xu, Carbon, 43, 1709 (2005).
Y. R. Dong, N. Nishiyama, Y. Egashira and K. Ueyama, Ind. Eng. Chem. Res., 46, 4040 (2007).
H. T. Wang and J. F. Yao, Ind. Eng. Chem. Res., 45, 6393 (2006).
L. He, D. Li, G. Zhang, A. A. Webley, D. Zhao and H. Wang, Ind. Eng. Chem. Res., 49, 4715 (2010).
J. Horvat, B. Klaic, B. Metelko and V. Sunjic, Tetrahedron Lett., 26, 2111 (1985).
J. Horvat, B. Klaic, B. Metelko and V. Sunjic, Croat. Chem. Acta, 59, 429 (1986).
S. Bertarione, F. Bonino, F. Cesano, A. Damin, D. Scarano and A. Zecchina, J. Phys. Chem. B, 112, 2580 (2008).
S. Bertarione, F. Bonino, F. Cesano, S. Jain, M. Zanetti, D. Scarano and A. Zecchina, J. Phys. Chem. B, 113, 10571 (2009).
A. J.G. Zarbin, R. Bertholdo and M. A. F. C. Oliveira, Carbon, 40, 2413 (2002).
M. Choura, N.M. Belgacem and A. Gandini, Macromolecules, 29, 3839 (1996).
R. Gonzalez, J.M. Figueroa and H. Gonzalez, European Poly. Journal, 38, 287 (2002).
Y. R. Swasti and M. Murkovic, Food Funct., 3, 965 (2012).
M. S. Kane, J. F. Goellner and H. C. Foley, Chem. Mater., 8, 2159 (1996).
A. P. Dunlop and F. N. Peters, The Furans; Reinhold Publishing Co., New York (1953).
C. Moreau, M. N. Belgacem and A. Gandini, Top. Catal., 27, 11 (2004).
R. T. Conley and I. Metil, J. Appl. Polym. Sci., 7, 37 (1963).
I. S. Chung, G. E. Maciel and G. E. Myers, Macromolecules, 17, 1087 (1984).
M. Principe, P. Ortis and R. Martinez, Polym. Int., 48, 637 (1999).
T. De la Garcia, M.R. Gomez, R. Martinez and C. Alonso, Polym. Int., 52, 86 (2003).
J. Yao, H. Wang, J. Liu, K.Y. Chan, L. Zhang and N. Xu, Carbon, 43, 1709 (2005).
E.M. Wewerka, J. Appl. Polym. Sci., 12, 1671 (1968).
C. L. Thomas, Catalytic Processes and Proven Catalysts, Academic Press, New York (1970).
C. N. Satterfield, Heterogeneous Catalysis in Practice, McGraw-Hill, New York (1980).
K. Tanabe, M. Misono, H. Hattori and Y. Ono, New Solid Acids and Bases, Elsevier, 51 (1989).
M. Hino and K. Arata, J. Chem. Soc. Chem. Commun., 18, 1259 (1988).
J. G. Santiesteban, J. C. Vartuli, S. Han, R. D. Bastian and C. D. Chang, J. Catal., 168, 431 (1997).
M. Hino and K. Arata, Chem. Lett., 6, 971 (1989).
T. Kim, A. Burrows, C. Kiely and I. E. Wachs, J. Catal., 246, 370 (2007).
I. E. Wachs, T. Kim and E. I. Ross, Catal. Today, 116, 162 (2006).
T. Kim, R. S. Assary, R. E. Pauls, C. L. Marshall, L. A. Curtiss and P. C. Stair, Catal. Commun., 46, 66 (2014).
E.M. Wewerka, E. D. Loughran and K. L. Walters, J. Appl. Polym. Sci., 15, 1437 (1971).
S. Barsberg and R.W. Berg, J. Phys. Chem. A, 110, 9500 (2006).
T. Kim, R. S. Assary, L. A. Curtiss, C. L. Marshall and P. C. Stair, J. Raman Spectrosc., 42, 2069 (2011).
A. Zecchina, F. Geobaldo, G. Spoto, S. Bordiga, G. Ricchiardi, R. Buzzoni and G. Petrini, J. Phys. Chem., 100, 16584 (1996).
Z. Wang, Z. Lu, X. Huang, R. Xue and L. Chen, Carbon, 36, 51 (1998).
Z. Wang, Z. Lu, Y. Huang, R. Xue, X. Huang and L. Chen, J. Appl. Phys., 82, 5705 (1997).
W. Hoareau, W.G. Trindade, B. Siegmund, A. Castellan and E. Frollini, Polym. Degrad. Stabil., 86, 567 (2004).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, T., Jeong, J., Rahman, M. et al. Characterizations of furfuryl alcohol oligomer/polymerization catalyzed by homogeneous and heterogeneous acid catalysts. Korean J. Chem. Eng. 31, 2124–2129 (2014). https://doi.org/10.1007/s11814-014-0322-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-014-0322-x