Heteropolyoxometalate Catalyzed Selective Oxidation of Alcohols to Carbonyl Compounds by Hydrogen Peroxide under Mild Condition
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Published:
Dec 29, 2017
Keywords:
heteropolyoxometalate oxidation alchohols hydrogen peroxide
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Abstract
Keggin-type heteropolyoxometalates has been used as catalysts for the oxidation of benzylic alcohols and secondary alcohols to the corresponding carbonyl compounds using environment-friendly H2O2 as oxidant at room temperature. The catalysts used in this study exhibit high selectivity in the oxidation of alcohols with no over-oxidation and formation of carboxylic acids. For vanadium(V)-substituted hepolyoxmetalates [Hx-2PVxW12-xO40]5- (x= 4 for POM 1 and 6 for POM 2), the catalytic activity decreases with increasing number of vanadium atoms in the catalyst.
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How to Cite
Agarwalla, U. S. (2017). Heteropolyoxometalate Catalyzed Selective Oxidation of Alcohols to Carbonyl Compounds by Hydrogen Peroxide under Mild Condition. Science, Engineering and Health Studies, 11(3), 25–31. https://doi.org/10.14456/sustj.2017.10
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Research Articles
References
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Choudary, B. M., Kantam, M. L., Rahman, R., Reddy, C. V., and Rao, K. K. (2001). The first example of activation of molecular oxygen by nickel in Ni-Al hydrotalcite: A novel protocol for the selective oxidation of alcohols. Angewandte Chemie International Edition, 40(4), 763-766.
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Highet, R. J., and Wildman, W. C. (1955). Solid manganese dioxide as an oxidizing agent. Journal of the American Chemical Society, 77(16), 4399-4401.
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Kanjina, W., and Trakarnpruk, W. (2009). Heteropolyoxometalate catalysts for oxidation of alcohols with hydrogen peroxide under green condition. Silpakorn University Science and Technology Journal, 3(1), 7-12.
Khenkin, A. M., Shimon, L. J. W., and Neumann, R. (2001). Antimony-substituted Keggin-type polyoxomolybdates: polar crystals and catalytic oxidative dehydrogenation of alcohols. European Journal of Inorganic Chemistry, 2001(3), 789-794.
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Lee, D. G., and Spitzer, U. A. (1970). Aqueous dichromate oxidation of primary alcohols. Journal of Organic Chemistry, 35(10), 3589-3590.
Ley, S. V., Norman, J., Griffith, W. P., and Marsden, S. P. (1994). A catalytic oxidant for organic synthesis. Synthesis, 639-666.
Matsushita, T., Ebitani, K. and Kaneda, K. (1999). Highly efficient oxidation of alcohols and aromatic compounds catalysed by the Ru-Co-Al hydrotalcite in the presence of molecular oxygen. Chemical Communications, 265-266.
Menger, F. M., and Lee, C. (1979). Oxidations with solid potassium permanganate. Journal of Organic Chemistry, 44(19), 3446-3448.
Mizuno, N., and Misono, M., (1998). Heterogeneous catalysis. Chemical Reviews, 98(1), 199-218.
Okuhara, T., and Misono, M. (1996). Catalytic chemistry of heteropoly compounds. Advances in Catalysis,41, 113- 252.
Pope, M. T. (1983). Isopoly and Heteropoly Anions, Springer: Berlin, Germany.
Muller, A. (2001). Polyoxometalate Chemistry, Kluwer Academic: Dordrecht, The Netherlands.
Semmelhack, M. F., Schmid, C. R., Cortes, D. A., and Chou, C. S. (1984). Oxidation of alcohols to aldehydes with oxygen and cupric ion, mediated by nitrosonium ion.Journal of the American Chemical Society, 106(11), 3374-3376.
.
Shapley, P. A., Zhang, N., Allen, J. L., Pool, D. H., and Liang, H. C. (2000). Selective alcohol oxidation with molecular oxygen catalyzed by Os-Cr and Ru-Cr complexes. Journal of the American Chemical Society, 122(6), 1079-1091.
Sheldon, R. A., and Kochi, J. K. (1981). Metal-catalysed oxidations of organic compounds: Academic Press, New York.
Sheldon, R. A., Arends, I. C. W. E., and Dijksman, A. (2000). New developments in catalytic alcohol oxidations for fine chemicals synthesis. Catalysis Today, 57(1-2), 157-166.
Smith, D. P., and Pope, M. T. (1973). Heteropoly 12-metallophosphates containing tungsten and vanadium: Preparation, voltammetry and properties of mono-, di-, tetra-, and hexavanado complexes. Inorganic Chemistry, 12(2), 331-336.
Stevens, R. V., Chapman, K. T., and Weller, H. N. (1980). Convenient and inexpensive procedure for oxidation of secondary alcohols to ketones. Journal of Organic Chemistry, 45(10), 2030-2032.
Venturello, C., and Gambaro, M. (1991). Selective oxidation of alcohols and aldehydes with hydrogen peroxide catalyzed by methyltrioctylammoniumtetrakis(oxodiperoxotungsto)phosphate(3-) under two-phase conditions. Journal of Organic Chemistry, 56(20), 5924-5931.
Wang, J., Yan, L., Li, G., Wang, X., Ding, Y., and Suo, J. (2005). Mono-substituted Keggin-polyoxometalate complexes as effective and recyclable catalyst for the oxidation of alcohols with hydrogen peroxide in biphasic system. Tetrahedron Letters, 46(41), 7023-7027.
Yamaguchi, K., and Mizuno, N. (2002). Heterogeneously catalyzed liquid-phase oxidation of alkanes and alcohols with molecular oxygen. New Journal of Chemistry, 26, 972-974.
Yamawaki, K., Nishihara, H., Yoshida, T., Ura, T., Yamada, H., Ishii, Y., and Ogawa, M. (1988). Ketonization of secondary hydroxyl groups of alcohols and diols with hydrogen peroxide under the influence of tricetylpyridinium-12-tungstophosphate. Synthetic Communications, 18(8), 869-875.
Yamawaki, K., Yoshida, T., Nishihara, H., Ishii, Y., and Ogawa, M. (1986). Chemoselective oxidation of secondary hydroxyl functions catalyzed by [PMo12O40]3-[C5H5N+(CH2)15CH3]3. Synthetic Communications, 16(5), 537-541.
Zhang, S. J., Gao, S., Xi, Z. W., and Xu, J. (2007). Solvent-free oxidation of alcohols catalyzed by an efficient and reusable heteropolyphosphatotungstate. Catalysis Communicatins, 8(3), 531-534.
Zhang, S., Zhao, G., and Gao, S. (2008). Secondary alcohol oxidation with hydrogen peroxide catalyzed by [n-C16H33N(CH3)3]3PW12O40: transform-and-retransform process between catalytic precursor and catalytic active species.Journal of Molecular Catalysis A: Chemical, 289(1-2), 22-27.
Bäckvall, J. -E. (2004). Modern Oxidation Methods, Wiley-VCH, Weinheim.
Ben-Daniel, R., Alsters, P., and R. Neumann. (2001). Selective aerovic oxidation of alcohols with a combination of a polyoxometalate and nitroxyl radical as catalysts. Journal of Organic Chemistry, 66(25), 8650-8653.
Brink, G. J., Arends, I. W. C. E., and Sheldon, R. A. (2000). Green, catalytic oxidation of alcohols in water. Science, 287 (5458), 1636-1639.
Carraro, M., Sandei, L., Sartorel, A., Scorrano, G., and Bonchio, M. (2006). Hybrid polyoxotungstates as second generation POM-based catalysts for microwave-assisted hydrogen peroxide activation. Organic Letters, 8(17), 3671-3674.
Chhikara, B. S., Chandra. R., and Tandon, V. (2005). Oxidation of alcohols with hydrogen peroxide catalyzed by a new imidazolium ion based phosphotungstate complex in ionic liquid. Journal of Catalysis, 230(2), 436-439.
Choudary, B. M., Kantam, M. L., Rahman, R., Reddy, C. V., and Rao, K. K. (2001). The first example of activation of molecular oxygen by nickel in Ni-Al hydrotalcite: A novel protocol for the selective oxidation of alcohols. Angewandte Chemie International Edition, 40(4), 763-766.
Collins, J. C., Hess, W. W., and Frank, F. J. (1968). Dipyridine-chromium (VI) oxide oxidation of alcohols in dichloromethane. Tetrahedron Letters, 9, 3363-3366.
Corey, E. J., and Suggs, J. W. (1975). Pyridiniumchlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Letters, 16(31), 2647-2650.
Haimov, A., and Neumann, R. (2002). Polyethylene glycol as a non-ionic liquid solvent for polyoxometalate catalyzed aerobic oxidation. Chemical Communications, 876-877.
Highet, R. J., and Wildman, W. C. (1955). Solid manganese dioxide as an oxidizing agent. Journal of the American Chemical Society, 77(16), 4399-4401.
Hill, C. L., and Prosser-McCartha, C. M. (1995). Homogeneous catalysis by transition metal oxygen anion clusters. Coordination Chemistry Review, 143, 407-455.
Holum, J. R. (1961). Study of the chromium (VI) oxide-pyridine complex. Journal of Organic Chemistry, 26, 4814-4816.
Hudlicky, M. (1990). Oxidations in Organic Chemistry, ACS, Washington DC.
Ishii, Y., Yamawaki, K., Ura, T., Yamada, H., Yoshida, T., and Ogawa, M. (1988). Hydrogen peroxide oxidation catalyzed by heteropoly acids combined with cetylpyridinium chloride. Journal of Organic Chemistry, 53(15), 3587-3593.
Ishii, Y., Yamawaki, K., Yoshida, T., Ura, T., and Ogawa, M. (1987). Oxidation of olefins and alcohols by peroxo-molybdenum complex derived from tris (cetylpyridinium) 12- molybdophosphate and hydrogen peroxide. Journal of Organic Chemistry, 52(9), 1868-1870.
Iwahama, T., Sakaguchi, S., Nishiyama, Y., and Ishii, Y. (1995). Aerobic oxidation of alcohols to carbonyl compounds catalyzed by n-hydroxyphthalimide (NHPI) combined with Co(acac)3. Tetrahedron Letters, 36(38), 6923-6926.
Jia, C. G., Jing, F. Y., Hu, W. D., Huang, M. Y., and Jiang, Y. Y. (1994). Liquid phase oxidation of alcohols by dioxygen using oxide-supported platinum catalysts. Journal of Molecular Catalysis A: Chemical, 91(1), 139-147.
Kanjina, W., and Trakarnpruk, W. (2009). Heteropolyoxometalate catalysts for oxidation of alcohols with hydrogen peroxide under green condition. Silpakorn University Science and Technology Journal, 3(1), 7-12.
Khenkin, A. M., Shimon, L. J. W., and Neumann, R. (2001). Antimony-substituted Keggin-type polyoxomolybdates: polar crystals and catalytic oxidative dehydrogenation of alcohols. European Journal of Inorganic Chemistry, 2001(3), 789-794.
Khenkin, A. M., and Neumann, R. (2002). Oxygen transfer from sulfoxides: Selective oxidation of alcohols catalyzed by polyoxomolybdates. Journal of Organic Chemistry, 67(20), 7075-7079.
Kozhevnikov, I. V. (2002). Catalysis by Polyoxometalates, Wiley: Chichester. U.K.
Köckritz, A., Sebek, M., Dittmar, A., Radnik, J., Brückner, A., Bentrup, U., Pohl, M.-M., Hugl, H., and Mägerlein, W. (2006). Ru-catalyzed oxidation of primary alcohols. Journal of Molecular Catalysis A: Chemical, 246(1-2), 85-99.
Larock, R. C. (1999). Comprehensive organictrans formations, Wiley-VCH, New York.
Lee, D. G., and Spitzer, U. A. (1970). Aqueous dichromate oxidation of primary alcohols. Journal of Organic Chemistry, 35(10), 3589-3590.
Ley, S. V., Norman, J., Griffith, W. P., and Marsden, S. P. (1994). A catalytic oxidant for organic synthesis. Synthesis, 639-666.
Matsushita, T., Ebitani, K. and Kaneda, K. (1999). Highly efficient oxidation of alcohols and aromatic compounds catalysed by the Ru-Co-Al hydrotalcite in the presence of molecular oxygen. Chemical Communications, 265-266.
Menger, F. M., and Lee, C. (1979). Oxidations with solid potassium permanganate. Journal of Organic Chemistry, 44(19), 3446-3448.
Mizuno, N., and Misono, M., (1998). Heterogeneous catalysis. Chemical Reviews, 98(1), 199-218.
Okuhara, T., and Misono, M. (1996). Catalytic chemistry of heteropoly compounds. Advances in Catalysis,41, 113- 252.
Pope, M. T. (1983). Isopoly and Heteropoly Anions, Springer: Berlin, Germany.
Muller, A. (2001). Polyoxometalate Chemistry, Kluwer Academic: Dordrecht, The Netherlands.
Semmelhack, M. F., Schmid, C. R., Cortes, D. A., and Chou, C. S. (1984). Oxidation of alcohols to aldehydes with oxygen and cupric ion, mediated by nitrosonium ion.Journal of the American Chemical Society, 106(11), 3374-3376.
.
Shapley, P. A., Zhang, N., Allen, J. L., Pool, D. H., and Liang, H. C. (2000). Selective alcohol oxidation with molecular oxygen catalyzed by Os-Cr and Ru-Cr complexes. Journal of the American Chemical Society, 122(6), 1079-1091.
Sheldon, R. A., and Kochi, J. K. (1981). Metal-catalysed oxidations of organic compounds: Academic Press, New York.
Sheldon, R. A., Arends, I. C. W. E., and Dijksman, A. (2000). New developments in catalytic alcohol oxidations for fine chemicals synthesis. Catalysis Today, 57(1-2), 157-166.
Smith, D. P., and Pope, M. T. (1973). Heteropoly 12-metallophosphates containing tungsten and vanadium: Preparation, voltammetry and properties of mono-, di-, tetra-, and hexavanado complexes. Inorganic Chemistry, 12(2), 331-336.
Stevens, R. V., Chapman, K. T., and Weller, H. N. (1980). Convenient and inexpensive procedure for oxidation of secondary alcohols to ketones. Journal of Organic Chemistry, 45(10), 2030-2032.
Venturello, C., and Gambaro, M. (1991). Selective oxidation of alcohols and aldehydes with hydrogen peroxide catalyzed by methyltrioctylammoniumtetrakis(oxodiperoxotungsto)phosphate(3-) under two-phase conditions. Journal of Organic Chemistry, 56(20), 5924-5931.
Wang, J., Yan, L., Li, G., Wang, X., Ding, Y., and Suo, J. (2005). Mono-substituted Keggin-polyoxometalate complexes as effective and recyclable catalyst for the oxidation of alcohols with hydrogen peroxide in biphasic system. Tetrahedron Letters, 46(41), 7023-7027.
Yamaguchi, K., and Mizuno, N. (2002). Heterogeneously catalyzed liquid-phase oxidation of alkanes and alcohols with molecular oxygen. New Journal of Chemistry, 26, 972-974.
Yamawaki, K., Nishihara, H., Yoshida, T., Ura, T., Yamada, H., Ishii, Y., and Ogawa, M. (1988). Ketonization of secondary hydroxyl groups of alcohols and diols with hydrogen peroxide under the influence of tricetylpyridinium-12-tungstophosphate. Synthetic Communications, 18(8), 869-875.
Yamawaki, K., Yoshida, T., Nishihara, H., Ishii, Y., and Ogawa, M. (1986). Chemoselective oxidation of secondary hydroxyl functions catalyzed by [PMo12O40]3-[C5H5N+(CH2)15CH3]3. Synthetic Communications, 16(5), 537-541.
Zhang, S. J., Gao, S., Xi, Z. W., and Xu, J. (2007). Solvent-free oxidation of alcohols catalyzed by an efficient and reusable heteropolyphosphatotungstate. Catalysis Communicatins, 8(3), 531-534.
Zhang, S., Zhao, G., and Gao, S. (2008). Secondary alcohol oxidation with hydrogen peroxide catalyzed by [n-C16H33N(CH3)3]3PW12O40: transform-and-retransform process between catalytic precursor and catalytic active species.Journal of Molecular Catalysis A: Chemical, 289(1-2), 22-27.