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Synthesis, Characterization and Reduction of p-Nitrobenzoyl Hydroxypropyl Cellulose
Corresponding Author(s) : Chitchamai Ovatlarnporn
Asian Journal of Chemistry,
Vol. 27 No. 5 (2015): Vol 27 Issue 5
Abstract
Synthesis and structural characterizations of p-nitrobenzoyl and p-aminobenzoyl hydroxypropyl cellulose were reported in this work. Nitrobenzoyl-hydroxypropyl cellulose was synthesized in good yield via esterification reaction between p-nitrobenzoyl chloride and hydroxyl groups of hydroxypropyl cellulose (Mw 80,000 and 100,000) in dried dichloromethane using pyridine as a catalyst. p-Nitrobenzoylhydroxypropyl cellulose was then attempted many times for its reduction to p-aminobenzoylhydroxypropyl cellulose by using three different reducing agents like sodium dithionite, tin(II) chloride dihydrate and palladium on activated charcoal. The resulting p-nitrobenzoyl and p-aminobenzoyl hydroxypropyl cellulose were characterized by FT-IR and 1H NMR.
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- R.R. Mclaughlin and D.B. Mutton, Can. J. Chem., 33, 646 (1955); doi:10.1139/v55-076.
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References
R. Kaplanek and V. Krchnak, Tetrahedron Lett., 54, 2600 (2013); doi:10.1016/j.tetlet.2013.03.010.
P. Berlin, D. Klemm, A. Jung, H. Liebegott, R. Rieseler and J. Tiller, Cellulose, 10, 343 (2003); doi:10.1023/A:1027342027945.
S. Chang, B. Condon and J.V. Edwards, Fibers and Polymers, 11, 1101 (2010); doi:10.1007/s12221-010-1101-x.
R.R. Mclaughlin and D.B. Mutton, Can. J. Chem., 33, 646 (1955); doi:10.1139/v55-076.
R.A. Scheuerman and D. Tumelty, Tetrahedron Lett., 41, 6531 (2000);
doi:10.1016/S0040-4039(00)00959-X.
P.S. Kumar and K.M. Lokanatha Rai, Chem. Papers, 66, 772 (2012); doi:10.2478/s11696-012-0195-6.
J. Zhang, J. Wu, Y. Cao, S. Sang, J. Zhang and J. He, Cellulose, 16, 299 (2009); doi:10.1007/s10570-008-9260-2.
T.F. Conceicao, J.R. Bertolino, G.M.O. Barra, S.L. Mireski, A.C. Joussef and A.T.N. Pires, J. Braz. Chem. Soc., 19, 111 (2008); doi:10.1590/S0103-50532008000100016.
D.H. Campbell, E. Luescher and L.S. Lerman, Proc. Natl. Acad. Sci. USA, 37, 575 (1951); doi:10.1073/pnas.37.9.575.
J.G. De Vries and R.M. Kellogg, J. Org. Chem., 45, 4126 (1980); doi:10.1021/jo01309a011.