Issue
Korean Journal of Chemical Engineering,
Vol.31, No.12, 2124-2129, 2014
Characterizations of furfuryl alcohol oligomer/polymerization catalyzed by homogeneous and heterogeneous acid catalysts
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 ℃, 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.
[References]
  1. Huber GW, Chheda JN, Barrett CJ, Dumesic JA, Science, 308, 1446, 2005
  2. Shi N, Liu Q, Zhang Q, Wang T, Ma L, Green Chem., 15, 1967, 2013
  3. Kim T, Assary RS, Marshall CL, Gosztola DJ, Curtiss LA, Stair PC, ChemCatChem., 3, 1451, 2011
  4. Werpy T, Petersen G, Top Value Added Chemicals from Biomass, US Department of Energy, Office of Scientific and Technical Information, Oak Ridge, TN, No. DOE/GO-102004-1992, http://www.nrel.gov/docs/fy04osti/35523.pdf., 2004
  5. Bozell JJ, Peterson GR, Green Chem., 12, 539, 2010
  6. Maldonado GMG, Assary RS, Dumesic J, Curtiss LA, Energy Environ. Sci., 5, 6981, 2012
  7. Patil SKR, Lund CRF, Energy Fuels, 25(10), 4745, 2011
  8. Patil SKR, Heltzel J, Lund CRF, Energy Fuels, 26(8), 5281, 2012
  9. Radhakrishnan L, Reboul J, Furukawa S, Srinivasu P, Kitagawa S, Yamauchi Y, Chem. Mater., 23, 1225, 2011
  10. Park IS, Choi M, Kim TW, Ryoo R, J. Mater. Chem., 16, 3409, 2006
  11. Yi B, Rajagopalan R, Foley HC, Kim UJ, Liu XM, Eklund PC, J. Am. Chem. Soc., 128(34), 11307, 2006
  12. Men XH, Zhang ZZ, Song HJ, Wang K, Jiang W, Comp. Sci. Technol., 68, 1042, 2008
  13. Yao J, Wang H, Liu J, Chan KY, Zhang L, Xu N, Carbon, 43, 1709, 2005
  14. Dong YR, Nishiyama N, Egashira Y, Ueyama K, Ind. Eng. Chem. Res., 46(12), 4040, 2007
  15. Wang HT, Yao JF, Ind. Eng. Chem. Res., 45(19), 6393, 2006
  16. He L, Li D, Zhang G, Webley AA, Zhao D, Wang H, Ind. Eng. Chem. Res., 49, 4715, 2010
  17. Horvat J, Klaic B, Metelko B, Sunjic V, Tetrahedron Lett., 26, 2111, 1985
  18. Horvat J, Klaic B, Metelko B, Sunjic V, Croat. Chem. Acta, 59, 429, 1986
  19. Bertarione S, Bonino F, Cesano F, Damin A, Scarano D, Zecchina A, J. Phys. Chem. B, 112(9), 2580, 2008
  20. Bertarione S, Bonino F, Cesano F, Jain S, Zanetti M, Scarano D, Zecchina A, J. Phys. Chem. B, 113(31), 10571, 2009
  21. Zarbin AJG, Bertholdo R, Oliveira MAFC, Carbon, 40, 2413, 2002
  22. Choura M, Belgacem NM, Gandini A, Macromolecules, 29(11), 3839, 1996
  23. Gonzalez R, Figueroa JM, Gonzalez H, European Poly. Journal, 38, 287, 2002
  24. Swasti YR, Murkovic M, Food Funct., 3, 965, 2012
  25. Kane MS, Goellner JF, Foley HC, Chem. Mater., 8, 2159, 1996
  26. Dunlop AP, Peters FN, The Furans; Reinhold Publishing Co., New York, 1953
  27. Moreau C, Belgacem MN, Gandini A, Top. Catal., 27, 11, 2004
  28. Conley RT, Metil I, J. Appl. Polym. Sci., 7, 37, 1963
  29. Chung IS, Maciel GE, Myers GE, Macromolecules, 17, 1087, 1984
  30. Principe M, Ortis P, Martinez R, Polym. Int., 48, 637, 1999
  31. Garcia TDlC, Gomez MR, Martinez R, Alonso C, Polym. Int., 52, 86, 2003
  32. Yao J, Wang H, Liu J, Chan KY, Zhang L, Xu N, Carbon, 43, 1709, 2005
  33. Wewerka EM, J. Appl. Polym. Sci., 12, 1671, 1968
  34. Thomas CL, Catalytic Processes and Proven Catalysts, Academic Press, New York, 1970
  35. Satterfield CN, Heterogeneous Catalysis in Practice, McGraw-Hill, New York, 1980
  36. Tanabe K, Misono M, Hattori H, Ono Y, New Solid Acids and Bases, Elsevier, 51, 1989
  37. Hino M, Arata K, J. Chem. Soc. Chem. Commun., 18, 1259, 1988
  38. Santiesteban JG, Vartuli JC, Han S, Bastian RD, Chang CD, J. Catal., 168(2), 431, 1997
  39. Hino M, Arata K, Chem. Lett., 6, 971, 1989
  40. Kim T, Burrows A, Kiely CJ, Wachs IE, J. Catal., 246(2), 370, 2007
  41. Wachs IE, Kim T, Ross EI, Catal. Today, 116(2), 162, 2006
  42. Kim T, Assary RS, Pauls RE, Marshall CL, Curtiss LA, Stair PC, Catal. Commun., 46, 66, 2014
  43. Wewerka EM, Loughran ED, Walters KL, J. Appl. Polym. Sci., 15, 1437, 1971
  44. Barsberg S, Berg RW, J. Phys. Chem. A, 110(30), 9500, 2006
  45. Kim T, Assary RS, Curtiss LA, Marshall CL, Stair PC, J. Raman Spectrosc., 42, 2069, 2011
  46. Zecchina A, Geobaldo F, Spoto G, Bordiga S, Ricchiardi G, Buzzoni R, Petrini G, J. Phys. Chem., 100(41), 16584, 1996
  47. Wang Z, Lu Z, Huang X, Xue R, Chen L, Carbon, 36, 51, 1998
  48. Wang Z, Lu Z, Huang Y, Xue R, Huang X, Chen L, J. Appl. Phys., 82, 5705, 1997
  49. Hoareau W, Trindade WG, Siegmund B, Castellan A, Frollini E, Polym. Degrad. Stab., 86, 567, 2004