Abstract
The effect of β-cyclodextrin on the catalytic stability and reactivity of methylrhenium trioxide (MTO), CH3ReO3, which has been used for activation of hydrogen peroxide toward oxidation and epoxidation reactions, was studied using UV–Vis spectrophotometery. The stability and reactivity of the new catalytic system (MTO/β-CD) to activate H2O2 toward oxidation of indigo blue dye were investigated in basic media. Furthermore, effects of inclusion stoichiometry, temperature and concentrations of hydrogen peroxide on the stability and reactivity of the MTO/β-CD system were investigated. The formation of the inclusion complex between MTO and β-CD was confirmed experimentally using the changes in the UV–Vis absorption spectra. The results of this study demonstrate that the complexation process was better guaranteed when the amount of β-CD is higher than that of MTO, using a 1:2 molar ratio of MTO:β-CD enhances both the activity and stability of the catalyst. The results showed that the stability of the catalytic system was enhanced in presence of β-CD with maintaining good reactivity of the MTO even in the presence of high concentration of NaOH. The changes of thermodynamic activation parameters (ΔH≠ and ΔS≠) for the oxidation reaction of indigo with H2O2 catalyzed by MTO/β-CD system were determined on the basis of the experimental data.
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References
Laszlo, P., Levart, M., Bouhlel, E., Montaufier, M., Singh, G.P., Oyama, S.T., Hightower, J.W. (eds.): Catalytic Selective Oxidation, Chapter 4. American Chemical Society, Washington, DC (1993)
Al-Ajlouni, A.M., Espenson, J.H.: Kinetics and mechanism of the epoxidation of alkyl-substituted alkenes by hydrogen peorxide, catalyzed by methylrhenium trioxid. J. Org. Chem. 61, 3969–3976 (1996)
Herrmann, W.A.: Olefins from Aldehydes in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd edn, vol. 3, pp. 1078–1086. Wiley VCH, Weinheim, Germany (2002)
Crestini, C., Caponi, M.C., Argyropoulos, D.S., Saladino, R.: Immoblized methyltrioxorhenium (MTO)/H2O2 systems for the oxidation of lignin and lignin model compounds. Bioorg. Med. Chem. 14, 5292–5302 (2006)
Saladino, R., Neri, V., Pelliccia, A.R., Mincione, E.: Selective epoxidation of monoterpenes with H2O2 and polymer-supported methylrheniumtrioxide systems. Tetrahedron 59, 7403–7408 (2003)
Zhu, Z., Espenson, J.H.: Oxidation of alkynes by hydrogen peroxide catalyzed by methylrhenium trioxide. J. Org. Chem. 60, 7728–7732 (1995)
Adam, W., Herrmann, W.A., Saha-Moller, C.R., Shimizu, M.: Oxidation of methoxybenzenes to p-benzoquinones catalyzed by methyltrioxorhenium(VII). J. Mol. Catal. A Chem. 97, 15–20 (1995)
Bernini, R., Mincione, E., Cortese, M., Aliotta, G., Saladino, R.: A new and efficient Baeyer-Villiger rearrangement of flavanone derivatives by the methyltrioxorhenium/H2O2 catalytic system. Tetrahedron Lett. 42, 5401–5404 (2001)
Schuchardt, U., Mandelli, D., Shul’pin, G.B.: Methyltrioxorhenium catalyzed oxidation of saturated and aromatic hydrocarbons by H2O2 in air. Tetrahedron Lett. 37, 6487–6490 (1996)
Adam, W., Herrmann, W.A., Lin, J., Saha-Moller, C.R.: Catalytic oxidation of phenols to p-quinones with the hydrogen peroxide and methyltrioxorhenium(VII) system. J. Org. Chem. 59, 8281–8283 (1994)
Soldaini, G., Cardona, F., Goti, A.: Methyltrioxorhenium catalyzed domino epoxidation-nucleophilic ring opening of glycals. Tetrahedron Lett. 44, 5589–5592 (2003)
Ballistreri, F., Chillemi, R., Sciuto, S., Tomaselli, G.A., Toscano, R.M.: Regio and stereoselective oxidations of unsaturated steroidal compounds with H2O2 mediated by CH3ReO3. Steroids 71, 565–577 (2006)
Zhang, Z., Wang, J.: Recent studies on the reactions of α-diazocarbonyl compounds. Tetrahedron 64, 6577–6605 (2008)
Gonzales, J.M., Distasio Jr, R., Periana, R.A., Goddard III, W.A., Oxgaard, J.: Methylrhenium trioxide revisited: mechanisms for nonredox oxygen insertion in an M-CH3 bond. J. Am. Chem. Soc. 129, 15794–15804 (2007)
Herrmann, W.A., Fischer, R.W., Marz, D.W.: Methyltrioxorhenium as catalyst for olefin oxidation. Angew. Chem. Int. Ed. Engl. 30, 1638–1641 (1991)
Petrovski, Z., Braga, S.S., Santos, A.M., Rodrigues, S.S., Goncalves, I.S., Pillinger, M., Kuhn, F.E., Romao, C.C.: Synthesis and characterization of the inclusion compound of a ferrocenyldiimine dioxomolybdenum complex with heptakis-2,3,6-tri-O-methyl-β-cyclodextrin. Inorg. Chim. Acta 358, 981–988 (2005)
Braga, S.S., Gago, S., Seixas, J.D., Valente, A.A., Pillinger, M., Santos, T.M., Goncalves, I.S., Romao, C.C.: β-Cyclodextrin and permethylated β-cyclodextrin inclusion compounds of a cylopentadienyl molybdenum tricarbonyl complex and their use as cyclooctene epoxidation catalyst precursors. Inorg. Chim. Acta 359, 4757–4764 (2006)
Caron, L., Bricout, H., Tilloy, S., Ponchel, A., Landy, D., Fourmentin, S., Monflier, E.: Molecular recognition between a water-soluble organometallic complex and a β-cyclodextrin: first example of second-sphere coordination adducts possessing a catalytic activity. Adv. Synth. Catal. 346, 1449–1456 (2004)
Fenyvesi, E., Szente, L., Russel, N.R., McNamara, M.: In: Szejtli, J., Osa, T. (eds.) Comprehensive Supramolecular Chemistry, vol. 3, p. 305. Pergamon Press, Oxford, UK (1996)
Soldaini, G., Cardona, F., Goti, A.: Catalytic oxidation of imines based on methyltrioxorhenium/urea hyrogen peroxide: a mild and easy chemo- and regioselective entry to nitrones. Org. Lett. 9, 473–476 (2007)
Yin, G., Busch, D.H.: Mechanistic details of facilitate applications of an exceptional catalyst, methyltrioxorhenium: encouraging results from oxygen-18 isotopic probes. Catal. Lett. 130, 52–55 (2009)
Abu-Omar, M.M., Hansen, P.J., Espenson, J.H.: Deactivation of methylrhenium trioxide-peroxide catalysts by diverse and competing pathways. J. Am. Chem. Soc. 118, 4966–4974 (1996)
Matusi, Y., Sunouchi, A., Yamamato, T.: Inhibitory effect of cyclodextrins on the discoloration reaction of an anthocyanide, pelargonidin chloride in acidic media. J. Incl. Phenom. Mol. Recognit. Chem. 32, 57–67 (1998)
Hapiot, F., Tilloy, S., Monflier, E.: Cyclodextrins as supramolecular hosts for organometallic complexes. Chem. Rev. 106, 767–781 (2006)
Harada, A.: Preparation, properties and stereochemical aspects of inclusion compounds of organometallic complexes with cyclodextrins. In: Zanello, P. (ed.) Chain, Clusters, Inclusion Compounds, Paramagnetic Labels and Organic Rings; Stereochemisty of Organometallic and Inorganic Compounds, vol. 5, pp. 411–455. Elsevier, Amsterdam (1994)
Ramusino, M.C., Bartolomei, M., Rufini, L.: H-NMR and UV-spectroscopic study of the inclusion complex formation between pyridoxine and β- and γ-cyclodextrin. J. Incl. Phenom. Mol. Recognit. Chem. 25, 113–116 (1996)
Kanagaraj, K., Pitchumani, K.: Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host. Tetrahedron Lett. 51, 3312–3316 (2010)
Narayana Murthy, S., Madhav, B., Prakash Reddy, V., Nageswar, Y.V.D.: One-pot synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives using β-cyclodextrin as reusable catalyst in water. Tetrahedron Lett. 51, 3649–3653 (2010)
Cassez, A., Ponchel, A., Bricout, H., Fourmentin, S., Landy, D., Monflier, E.: Eco-efficient catalytic hydrodechlorination of carbon tetrachloride in aqueous cyclodextrin solutions. Catal. Lett. 108, 209–214 (2006)
Szejtli, J.: Introuction and general over view of cyclodextrin chemistry. Chem. Rev. 98, 1743–1753 (1998)
Al-Ajlouni, A.M., Espenson, J.H.: Epoxidation of styrenes by hydrogen peroxide as catalyzed by methylrhenium trioxide. J. Am. Chem. Soc. 117, 9243–9250 (1995)
Eyring, H.: The activated complex in chemical reactions. J. Chem. Phys. 3, 107–115 (1935)
Al-Ajlouni, A.M., Espenson, J.H., Bakac, A.: Reaction of hydrogen peroxide with the oxochromium(IV) ion by hydride transfer. Inorg. Chem. 32, 3162–3165 (1993)
Gemeay, A.H., Mansour, I.A., El-Sharkawy, R.G., Zaki, A.B.: Kinetics and mechanism of the heterogeneous catalyzed oxidative degradation of indigo carmine. J. Mol. Catal. A Chem. 193, 109–120 (2003)
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Financial support by Deanship of Research at Jordan University of Science and Technology (grant number 126/2001) is deeply appreciated.
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Al-Rawashdeh, N.A.F., Al-Ajlouni, A.M., Bukallah, S.B. et al. Activation of H2O2 by methyltrioxorhenium(VII) inside β-cyclodextrin. J Incl Phenom Macrocycl Chem 70, 471–480 (2011). https://doi.org/10.1007/s10847-010-9876-3
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DOI: https://doi.org/10.1007/s10847-010-9876-3