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2. When carried out in liquid acetone, the reaction is very slow and conversion is only up to 70%. See, A. M. Rouhi, Chem. Eng. News 2003, 81 (28), 37.
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For instance, ionic liquids are not biodegradable and members of the imidazolium series are more toxic than conventional organic solvents, as shown in: M. T. Garcia, N. Gathergood, P. J. Scammels, Green Chem. 2005, 7, 9.
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A series of acute toxicity tests on Danio rerio zebrafish exposing the fish to low concentrations of 10 milligrams per litre of some commonly used ionic solvents, both anionic and cationic, showed serious health damages: C. Pretti, C. Chiappe, D. Pieraccini, M. Gregori, F. Abramo, G. Monni, L. Intorre, Green Chem. 2006, 8, 238.
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note
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With the exception of the Pt/C catalyst used in the continuous, aerobic oxidation of sucrose, the low selectivity of supported noble metal catalysts requires, for industrial use, to be "promoted" by other metal species such as Bi. The resulting bi-metal catalysts are commercially employed for the aerobic oxidation of simple alcohols in the liquid phase, such as in the case of benzyl alcohols. For a recent work by industrial researchers on these systems,
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0242522411
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see: R. Anderson, K. Griffin, P. Johnston, P. L. Alsters, Adv. Synth. Catal. 2003, 345, 517.
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2/FAU zeolite: B. Z. Zhan, M. A. White, T. K. Sham, J. A. Pincock, R. J. Doucet, K. V. R. Rao, K. N. Robertson, T. S. Cameron, J. Am. Chem. Soc. 2003, 125, 2195;
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d) Ru/Al/Mg-hydrotalcite: K. Kaneda, T. Yamashita, T. Matsushita, K. Ebitani, J. Org. Chem. 1998, 63, 1750;
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f) Ru-hydroxyapatite: K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2000, 122, 7144.
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M. Pagliaro, S. Campestrini, R. Ciriminna, Chem. Soc. Rev. 2005, 34, 837.
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3I of the ordered hybrid material obtained from TEOS and 1-[3-(triethoxysilyl)propyl]imidazole with cetylpiridinium chloride as a template. Compound VII was synthesized by alkaline co-polycondensation of an ionic organotriethoxysilane (obtained by coupling 1-methylimidazole with 3-chloropropyltriethoxysilane) and TEOS with cetylpyridinium chloride as template.
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Even if extraordinary selectivity for the oxidation of primary alcohols to carboxylic acids in water was recently reported: M. Comotti, C. Della Pina, R. Matarrese, M. Rossi, Angew. Chem. 2004, 116, 5936;
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39
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M. D. Jones, R. Raja, J. M. Thomas, B. F. G. Johnson, D. W. Lewis, J. Rouzaud, K. D. M. Harris, Angew. Chem. 2003, 115, 4462;
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Interestingly, an analogous ionic entrapment of perruthenate within the hexagonal mesopores of silicate MCM-41 resulted in prolonged recyclablility of the solid catalyst in the oxidation of a variety of benzyl alcohols in toluene, see: A. Bleloch, B. F. G. Johnson, S. V. Ley, A. J. Price, D. S. Shepard, A. W. Thomas, Chem. Commun. 1999, 1907.
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Bleloch, A.1
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42
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note
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The chemical stability of the organic spacer group connecting imidazolium to the material's surface was shown by the absence of spurious signals in the GC-MS analysis of reaction samples.
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The catalyst does not degrade as shown by: i) the absence of leached Ru in the sc-phase during reaction; and ii) by the absence of any breakdown of the propyl spacer connecting the imidazole to the ceramic matrix (by GC-MS).
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High catalytic loads are practically important as they ensure high substrate-to-catalyst S/C ratio (small volume of material required), and functionalized silica gels prepared by the sol-gel route can be obtained with high catalytic load. These materials offer several technical advantages over well-known organic resin bound catalysts: A doped silica gel reacts much faster than conventional polymer bound reagents; works in all type of solvents without dissolving; it is easy to weigh and handle, mechanically stable, and works in any format being easily scaled-up. See also at the URL: http://www.silicycle. com.
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