Abstract
A novel method for the acetylation of wood was investigated and compared with the classical method based on acetic anhydride. The transesterification reaction between vinyl acetate (VA) and hydroxyl groups of maritime pine sapwood (Pinus pinaster Soland) was performed in the presence of potassium carbonate as a catalyst and led to acetylated wood in high yield. The transesterification reaction was confirmed by FTIR and 13C CP-MAS NMR spectroscopy. The efficiency of the VA transesterification increased with increasing temperature, reaction time, and catalyst amount, but a significant weight percentage gain (WPG) was obtained after only 3 h at 90°C.
References
Boonstra, M.G., Pizzi, A., Tekely, P., Pendlebury, J. (1996) Chemical modification of Norway spruce and Scots pine. A 13C NMR CP-MAS study of the reactivity and reactions of polymeric wood components with acetic anhydride. Holzforschung50:215–220.Search in Google Scholar
Chang, S.-T., Chang, H.-T. (2001) Comparisons of the photostability of esterified wood. Polym. Degrad. Stab.71:261–266.10.1016/S0141-3910(00)00171-3Search in Google Scholar
Dicke, R. (2004) A straight way to regioselectively functionalized polysaccharide esters. Cellulose11:255–263.10.1023/B:CELL.0000025426.82260.71Search in Google Scholar
Evans, P., Wallis, F.A., Owen, N.L. (2000) Weathering of chemically modified wood surfaces. Natural weathering of Scots pine acetylated to different weight gains. Wood Sci. Technol.34:151–165.10.1007/s002260000039Search in Google Scholar
Gilardi, G., Abis, L., Cass, A.E.G. (1995) Carbon-13 CP/MAS solid-state NMR and FT-IR spectroscopy of wood cell wall biodegradation. Enzyme Microbial Technol.17:268–275.10.1016/0141-0229(94)00019-NSearch in Google Scholar
Hagemeyer, H.J., Hull, D.C. (1949) Reactions of isopropenyl acetate. Ind. Eng. Chem.41:2920–2924.10.1021/ie50480a063Search in Google Scholar
Hill, C.A.S. Wood modification: Chemical, thermal and other processes. John Wiley and Sons, Chichester, UK, 2006.10.1002/0470021748Search in Google Scholar
Hill, C.A.S., Jones, D. (1996) The dimensional stabilisation of Corsican pine sapwood by reaction with carboxylic acid anhydrides. Holzforschung50:457–462.10.1515/hfsg.1996.50.5.457Search in Google Scholar
Hill, C.A.S., Forster, S.C., Farahani M.R.M., Hale, M.D.C., Ormondroyd, G.A., Williams, G.R. (2005) An investigation of cell wall micropore blocking as a possible mechanism for the decay resistance of anhydride modified wood. Int. Biodeterior. Biodegrad.55:69–76.10.1016/j.ibiod.2004.07.003Search in Google Scholar
Hon, D.N.-S., Ed. Chemical modification of lignocellulosic materials. Marcel Dekker, New York, 1996.Search in Google Scholar
Kattenbroek, B. (2005) How to introduce acetylated wood from the first commercial production into Europe. In: Proceedings of the 2nd European Conference on Wood Modification, October 6–7, 2005, Göttingen, Germany. Institute of Wood Biology and Wood Technology, University of Göttingen. pp. 398–403.Search in Google Scholar
Larsson Brelid, P. (2002) The influence of post-treatments on acetyl content for removal of chemicals after acetylation. Holz Roh Werkst.60:92–95.10.1007/s00107-002-0283-3Search in Google Scholar
Larsson Brelid, P., Simonson, R., Bergman, O, Nilsson, T. (2000) Resistance of acetylated wood to biological degradation. Holz Roh Werkst.58:331–337.10.1007/s001070050439Search in Google Scholar
Li, J.-Z., Furuno, T., Katoh, S. (2000) Chemical modification of wood by anhydrides without solvents or catalysts. J. Wood Sci.46:215–221.10.1007/BF00776452Search in Google Scholar
Liu, B.-K., Wang, N., Wu, Q., Xie, C.-Y., Lin, X.-F. (2005) Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives. Biotechnol. Lett.27:717–720.10.1007/s10529-005-5188-xSearch in Google Scholar
Mormann, W., Al-Higari, M. (2004) Acylation of starch with vinyl acetate in water. Starch/Stärke56:118–121.10.1002/star.200300238Search in Google Scholar
Ohkoshi, M. (2002) FTIR-PAS study of light-induced changes in the surface of acetylated or polyethylene glyco-impregnated wood. J. Wood. Sci.48:394–401.10.1007/BF00770699Search in Google Scholar
Otera, J. (1993) Transesterification. Chem. Rev.93:1449–1470.10.1021/cr00020a004Search in Google Scholar
Park, O.-J., Kim, D.-Y., Dordick, S. (2000) Enzyme-catalysed synthesis of sugar-containing monomers and linear polymers. Biotechnol. Bioeng.70:208–216.10.1002/1097-0290(20001020)70:2<208::AID-BIT10>3.0.CO;2-0Search in Google Scholar
Simonson, R., Rowell, R. (2000) A new process for the continuous acetylation of lignocellulosic fiber. In: Proceedings of the 5th Pacific Rim Bio-based Composites Symposium, December 10–13, 2000, Canberra, Australia. Department of Forestry, The Australian National University. pp. 190–196.Search in Google Scholar
Yoshimoto, K., Itatani, Y., Tsuda, Y. (1980) 13C nuclear magnetic resonance (NMR) spectra of O-acylglucoses. Additivity of shift parameters and its application to structure elucidation. Chem. Pharm. Bull.58:2065–2076.Search in Google Scholar
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