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Chromium(VI) Catalyzed Oxidation of Primary Alcohol by Polymer Supported Reagent: A Kinetic and Mechanistic Approach
Corresponding Author(s) : Vilas Y. Sonawane
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
The kinetic of chromium(VI) catalyzed oxidation of 1-phenyl ethanol has been studied by the rate of disappearance of [Cr(VI)]. The reaction is zero order with respect to [Cr(VI)]. The reagent supported on anion exchange resin was found to be more efficient in the oxidation reaction. The reagent is very easily separated from the reaction mixture and can be manually removed from the reaction mixture, which remains clear during and after the reaction. The kinetic of oxidation of 1-phenylethanol with chromic acid supported on anion exchange resin like Amberjet-4400 [Cl–] in 1,4-dioxane has been studied. The reaction is found to be of zero order each in concentration of alcohol and oxidant. The reaction constants involved in the mechanism and the activation parameters have been calculated. There is a good agreement between observed and calculated rate constants under different experimental conditions. Acetophenone was detected as end product.
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- W.Y. Song, W.K. Li and C.P. Jia, Chem. J. Univ., 20, 1767 (1999).
- W.Y. Song and H.M. Liu, Chin. J. Inorg. Chem., 16, 607 (2000).
- J.H. Shan, J. Qian and T.Y. Zhai, Chin. J. Inorg. Chem., 19, 843 (2003).
- S. Lakshmi and R. Renganathan, Int. J. Chem. Kinet., 28, 713 (1996).
- E.J. Corey and G. Schmidt, Tetrahedron Lett., 20, 399 (1979).
- M.N. Bhattacharjee, M.K. Choudhari, H.S. Dasgupta, N. Roy and D.T. Khating, Synthesis, 58 (1982).
- E.J. Corey, E.P.M. Barette and P.A. Margrious, Tetrahedron Lett., 24, 5855 (1985).
- F. Climinale, M. Camporeale, R. Mello, L. Troisi and R. Curci, J. Chem. Soc., Perkin Trans. II, 417 (1989).
- G.G. Sharma and M.K. Mahanti, Bull. Soc. Chem. Fr., 128, 449 (1991).
- K. Balasubramanian and V. Pratibha, Indian J. Chem., 25B, 326 (1986).
- B. Narayana and T. Cherian, J. Braz. Chem. Soc., 16, 197 (2005).
- A.J. Buglas and J.S. Waterhouse, J. Chem. Educ., 64, 3712 (1987).
- G. Cainelli, G. Cardillio, M. Orena and S. Sardri, J. Am. Chem. Soc., 98, 6767 (1976).
- T. Brunlet, C. Jouitteau and G. Gelhard, J. Org. Chem., 51, 4016 (1986).
- W.A. Mosher, H. Clement and R.L. Hillard, J. Am. Chem. Soc., 29, 565 (1993).
- W. Watanabe and F.H. Westheimer, J. Chem. Phys., 61, 17 (1979).
- M.M. Salunke, D.G. Salunke, A.S. Kanade, R.B. Mane and P.P. Wadgaonkar, Synth. Commun., 20, 1143 (1990).
- J. Matsuo, A. Kawana, K. Pudhon and T. Mukaiyama, Chem. Lett., 250 (2002).
- R.O. Hutchins, N.R. Natale, W.J. Cook and J. Ohr, Tetrahedron Lett., 18, 4167 (1977).
- J.H. Espenson, J. Am. Chem. Soc., 86, 5101 (1964)
References
W.Y. Song, W.K. Li and C.P. Jia, Chem. J. Univ., 20, 1767 (1999).
W.Y. Song and H.M. Liu, Chin. J. Inorg. Chem., 16, 607 (2000).
J.H. Shan, J. Qian and T.Y. Zhai, Chin. J. Inorg. Chem., 19, 843 (2003).
S. Lakshmi and R. Renganathan, Int. J. Chem. Kinet., 28, 713 (1996).
E.J. Corey and G. Schmidt, Tetrahedron Lett., 20, 399 (1979).
M.N. Bhattacharjee, M.K. Choudhari, H.S. Dasgupta, N. Roy and D.T. Khating, Synthesis, 58 (1982).
E.J. Corey, E.P.M. Barette and P.A. Margrious, Tetrahedron Lett., 24, 5855 (1985).
F. Climinale, M. Camporeale, R. Mello, L. Troisi and R. Curci, J. Chem. Soc., Perkin Trans. II, 417 (1989).
G.G. Sharma and M.K. Mahanti, Bull. Soc. Chem. Fr., 128, 449 (1991).
K. Balasubramanian and V. Pratibha, Indian J. Chem., 25B, 326 (1986).
B. Narayana and T. Cherian, J. Braz. Chem. Soc., 16, 197 (2005).
A.J. Buglas and J.S. Waterhouse, J. Chem. Educ., 64, 3712 (1987).
G. Cainelli, G. Cardillio, M. Orena and S. Sardri, J. Am. Chem. Soc., 98, 6767 (1976).
T. Brunlet, C. Jouitteau and G. Gelhard, J. Org. Chem., 51, 4016 (1986).
W.A. Mosher, H. Clement and R.L. Hillard, J. Am. Chem. Soc., 29, 565 (1993).
W. Watanabe and F.H. Westheimer, J. Chem. Phys., 61, 17 (1979).
M.M. Salunke, D.G. Salunke, A.S. Kanade, R.B. Mane and P.P. Wadgaonkar, Synth. Commun., 20, 1143 (1990).
J. Matsuo, A. Kawana, K. Pudhon and T. Mukaiyama, Chem. Lett., 250 (2002).
R.O. Hutchins, N.R. Natale, W.J. Cook and J. Ohr, Tetrahedron Lett., 18, 4167 (1977).
J.H. Espenson, J. Am. Chem. Soc., 86, 5101 (1964)