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N-Bromosuccinimide (NBS) – an efficient catalyst for acetylation of wood

  • Giridhar B. Nagarajappa , Krishna K. Pandey EMAIL logo , Aniket S. Shinde and Hosadu M. Vagdevi
Published/Copyright: July 22, 2015
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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.


Corresponding author: Krishna K. Pandey, Institute of Wood Science and Technology, 18th Cross Malleswaram, Bengaluru 560003, India, e-mail: ;

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

Received: 2015-4-8
Accepted: 2015-7-1
Published Online: 2015-7-22
Published in Print: 2016-5-1

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