Abstract
Solvent-free acetylation of rubberwood (Hevea brasiliensis Müll.Arg) with acetic anhydride (Ac2O) and by means of N-bromosuccinimide (NBS) as catalyst was carried out in an oil bath at 105°C and 120°C. The effect of catalyst concentration, temperature, and reaction time was studied. The extent of acetylation was measured by determining the weight percent gain (WPG), and the acetylated wood was characterized by FTIR-ATR, CP/MAS 13C NMR, and XRD spectroscopy. The presence of NBS in concentrations between 1.0% and 3.0% elevated the acetylation rate to a great extent. WPG increased from 8.1% without catalyst to 22.1% for 2% NBS concentration after 60 min reaction at 120°C. Similarly, after 60-min reaction time at 105°C, WPG with 3% NBS concentration was 19.0% compared to 7.6% with un-catalyzed reaction under the same reaction conditions. The effect of microwave heating (MWh) on the NBS-catalyzed acetylation was also investigated. A significant level of modification was achieved within a few minutes of MWh. The hydrophobic properties and dimensional stability of the acetylated wood were elevated. NBS was found to be an effective catalyst for wood acetylation.
Acknowledgments
This research was supported by the Department of Science and Technology, New Delhi (Grant No. SR/MERC/0120/2012).
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. Holzforschung 50:215–220.10.1515/hfsg.1996.50.3.215Search in Google Scholar
Chang, S.-T., Chang, H.-T. (2001) Inhibition of the photodiscoloration of wood by butyrylation. Holzforschung 55:255–259.10.1515/HF.2001.042Search in Google Scholar
Chung, S., Suidan, M.T., Venosa, A.D. (2011) Partially acetylated sugarcane bagasse for wicking oil from contaminated wetlands. Chem. Eng. Technol. 34:1989–1996.10.1002/ceat.201100353Search in Google Scholar
Faix, O. (1992) Fourier transform infrared spectroscopy. In: Methods in Lignin Chemistry. Eds. Lin, S.Y., Dence, C.W. Springer-Verlag, New York. pp. 83–109.10.1007/978-3-642-74065-7_7Search in Google Scholar
Harrington, K.J., Higgins, H.G., Michell, A.J. (1964) Infrared spectra of Eucalypus regnans F. Muell. and Pinus radiata D. Don. Holzforschung 18:108–113.10.1515/hfsg.1964.18.4.108Search in Google Scholar
Hergert, H.L. (1971) Infrared spectra. In: Lignins: Occurrence, Formation, Structure and Reactions. Eds. Sarkanen, K.V., Ludwig, C.H. Wiley Interscience, New York. pp. 267–297.Search in Google Scholar
Hill, C.A.S. Wood Modification: Chemical, Thermal and Other Processes. John Wiley and Sons, Ltd., Chichester, 2006.10.1002/0470021748Search in Google Scholar
Hill, C.A.S., Jones, D. (1996) The dimensional stabilization of Corsican pine sapwood by reaction with carboxylic acid anhydride: the effect of chain length. Holzforschung 50:457–462.10.1515/hfsg.1996.50.5.457Search in Google Scholar
Hill, C.A.S., Jones, D., Strickland, G., Cetin, N.S. (1998) Kinetic and mechanistic aspects of the acetylation of wood with acetic anhydride. Holzforschung 52:623–629.10.1515/hfsg.1998.52.6.623Search in Google Scholar
Hill, C.A.S., Cetin, N.S., Ozmen, N. (2000) Potential catalysts for the acetylation of wood. Holzforschung 54:269–272.10.1515/HF.2000.045Search in Google Scholar
Hu, W., Chen, S., Xu, Q., Wang, H. (2011) Solvent-free acetylation of bacterial cellulose under moderate conditions. Carbohydr. Polym. 83:1575–1581.10.1016/j.carbpol.2010.10.016Search in Google Scholar
Karimi, B., Seradj, H. (2001) N-bromosuccinimide (NBS), a novel and highly effective catalyst for acetylation of alcohols under mild reaction conditions. Synlett. 4:519–520.10.1055/s-2001-12321Search in Google Scholar
Li, J., Furuno, T., Zhou, W., Ren, Q., Han, X., Zhao, J. (2009a) Properties of acetylated wood. prepared at low temperature in the presence of catalysts. J. Wood Chem. Technol. 29:241–250.10.1080/02773810903009499Search in Google Scholar
Li, J., Zhang, L.P., Peng, F., Bian, J., Yuan, T.-Q., Xu, F., Sun, R. (2009b) Microwave-assisted solvent-free acetylation of cellulose with acetic anhydride in the presence of iodine as a catalyst. Molecules 14:3551–3566.10.3390/molecules14093551Search in Google Scholar PubMed PubMed Central
Matsuda, H. (1996) Chemical modification of solid wood. In: Chemical Modification of Lignocellulosic Materials. Ed. Hon, D.N.S. Marcel Dekker, New York. pp. 159–183.10.1201/9781315139142-6Search in Google Scholar
Obataya, E., Minato, K. (2008) Potassium acetate-catalyzed acetylation of wood: extraordinarily rapid acetylation at 120°C. Wood Sci. Technol. 42:567–577.10.1007/s00226-008-0179-4Search in Google Scholar
Obataya, E., Minato, K. (2009a) Potassium acetate-catalyzed acetylation of wood: reaction rates at low temperatures. Wood Sci. Technol. 43:405–413.10.1007/s00226-008-0212-7Search in Google Scholar
Obataya, E., Minato, K. (2009b) Potassium acetate-catalyzed acetylation of wood at low temperatures II: vapor phase acetylation at room temperature. J. Wood Sci. 55:23–26.10.1007/s10086-008-0996-ySearch in Google Scholar
Pandey, K.K. (1999) A study of chemical structure of softwood and hardwood and wood polymers by FTIR spectroscopy. J. Appl. Polym. Sci. 71:969–1975.10.1002/(SICI)1097-4628(19990321)71:12<1969::AID-APP6>3.0.CO;2-DSearch in Google Scholar
Park, S., Baker, J.O., Himmel, M.E., Parilla, P.A., Johnson, D.K. (2010) Cellulose crystallinity index: measurement techniques and their impact on interpreting cellulose performance. Biotechnol. Biofuels 3:1–10.10.1186/1754-6834-3-10Search in Google Scholar PubMed PubMed Central
Prasad, B.E., Pandey, K.K. (2012) Solvent-free chemical modification of wood by acetic and butyric anhydride with iodine as catalyst. Holzforschung 66:967–971.10.1515/hf-2011-0223Search in Google Scholar
Rodrigues, J., Faix, O., Pereira, H. (1998) Determination of lignin content of Eucalyptus globulus wood using FTIR spectroscopy. Holzforschung 52:46–50.10.1515/hfsg.1998.52.1.46Search in Google Scholar
Rowell, R.M. (1983) Chemical modification of wood. For. Prod. Abstr. 6:363–382.Search in Google Scholar
Rowell, R.M. (2006) Chemical modification of wood: a short review. Wood Mater. Sci. Eng. 1:29–33.10.1080/17480270600670923Search in Google Scholar
Rowell, R.M. (2013) Chemical modification of wood. In: Handbook of Wood Chemistry and Wood Composites. Ed. Rowell, R.M. Taylor and Francis, CRC Press, Florida. pp. 537–598.10.1201/b12487Search in Google Scholar
Rowell, R.M., Ellis, W.D. (1978) Determination of dimensional stabilization of wood using the water-soaked method. Wood Fiber Sci. 10:104–111.Search in Google Scholar
Sivonen, H., Nuopponen, M., Maunu, S.L., Sundholm, F., Vuorinen, T. (2003) Carbon-thirteen cross-polarization magic angle spinning nuclear magnetic resonance and Fourier transform infrared studies of thermally modified wood exposed to brown and soft rot fungi. Appl. Spectrosc. 57:266–273.10.1366/000370203321558164Search in Google Scholar PubMed
Sun, X.F., Sun, R.C., Sun, J.X. (2004) Acetylation of sugarcane bagasse using NBS as a catalyst under mild reaction conditions for the production of oil sorption-active materials. Biores. Technol. 95:343–350.10.1016/j.biortech.2004.02.025Search in Google Scholar PubMed
©2016 by De Gruyter
Articles in the same Issue
- Frontmatter
- Original Articles
- Synthesis and enzymatic hydrolysis of a diaryl benzyl ester model of a lignin-carbohydrate complex (LCC)
- Influence of chip presteaming conditions on kraft pulp composition and properties
- Isolating nanocellulose fibrills from bamboo parenchymal cells with high intensity ultrasonication
- Chemical improvement of surfaces. Part 4: Significantly enhanced hydrophobicity of wood by covalent modification with p-silyl-functionalized benzoates
- N-Bromosuccinimide (NBS) – an efficient catalyst for acetylation of wood
- Silane nanofilm formation by sol-gel processes for promoting adhesion of waterborne and solvent-borne coatings to wood surface
- Mechanical properties of wood flour/poly (lactic acid) composites coupled with waterborne silane-polyacrylate copolymer emulsion
- Analysis of the open-hole compressive strength of spruce
- Characterisation of cubic oak specimens from the Vasa ship and recent wood by means of quasi-static loading and resonance ultrasound spectroscopy (RUS)
- Strength properties and dimensional stability of particleboards with different proportions of thermally treated recycled pine particles
- Chemical characterization of cork and phloem from Douglas fir outer bark
- Wood microfibril angle variation after drying
Articles in the same Issue
- Frontmatter
- Original Articles
- Synthesis and enzymatic hydrolysis of a diaryl benzyl ester model of a lignin-carbohydrate complex (LCC)
- Influence of chip presteaming conditions on kraft pulp composition and properties
- Isolating nanocellulose fibrills from bamboo parenchymal cells with high intensity ultrasonication
- Chemical improvement of surfaces. Part 4: Significantly enhanced hydrophobicity of wood by covalent modification with p-silyl-functionalized benzoates
- N-Bromosuccinimide (NBS) – an efficient catalyst for acetylation of wood
- Silane nanofilm formation by sol-gel processes for promoting adhesion of waterborne and solvent-borne coatings to wood surface
- Mechanical properties of wood flour/poly (lactic acid) composites coupled with waterborne silane-polyacrylate copolymer emulsion
- Analysis of the open-hole compressive strength of spruce
- Characterisation of cubic oak specimens from the Vasa ship and recent wood by means of quasi-static loading and resonance ultrasound spectroscopy (RUS)
- Strength properties and dimensional stability of particleboards with different proportions of thermally treated recycled pine particles
- Chemical characterization of cork and phloem from Douglas fir outer bark
- Wood microfibril angle variation after drying