Abstract
Aluminum containing mesoporous molecular sieves, AlSBA-1 (nSi/nAl = 2, 5, 10 and 15) was synthesized hydrothermally using the template, cetyltriethylammonium bromide. They were characterized by XRD, BET, SEM and FT-IR. All the XRD patterns showed characteristic reflections of the three dimensional space group Pm3n. The catalytic activity was tested for the synthesis of 7-methoxy-4-methyl coumarin via Pechmann condensation of 3-methoxyphenol and ethyl acetoacetate. The reaction parameters, temperature, time, feed ratio, catalyst were optimized in order to obtain high conversion and product selectivity. Among the AlSBA-1 molecular sieves, AlSBA-1(2) exhibited higher activity than others.
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References
Cravotto, G., Nano, G.M., Palmisanob, G., Tagliapietra, S.: An Asymmetric Approach to Coumarin Anticoagulants via Hetero-Diels-Alder cycloaddition. Tetrahedron Asymm. 12, 707–709 (2001)
Kennedy, O., Thornes, R.D.: Coumarins: Biology. Applications and Mode of Action. Wiley and Sons, Chichester (1997)
Zahradnik, M.: The Production and Application of Fluorescent Brightening Agents. Wiley and Sons (1990)
Murray, R.D.H., Mendez, J., Brown, S.A.: The Natural Coumarins: Occurrence, Chemistry and Biochemistry. Wiley and Sons, New York (1982)
Von Pechmann, H., Duisberg, C.: Chem Ber. 17, 929 (1884)
Johnson, J.R.: The Perkin Reaction and Related Reactions. Org. React. 1, 210 (1942)
Jones, G.: The Knoevenagel Condensation. Org. React. 15, 204 (1967)
Shriner, R.L.: The Reformatsky Reaction. Org. React. 1, 1 (1942)
Narasimahan, N.S., Mali, R.S., Barve, M.V.: Synthesis, 906 (1979)
Schönberg, A., Latif, N.: The Action of Oxalyl Chloride on Indoles: A New Approach to Tryptamines. J. Am. Chem. Soc. 76, 6208–6210 (1954)
Li, T.S., Zhang, Z.H., Yang, F., Fu, C.G.: Montmorillonite Clay Catalysis. Part 7.1 An Environmentally Friendly Procedure for the Synthesis of Coumarins via Pechmann Condensation of Phenols with Ethyl Acetoacetate. J. Chem. Res (S), 38–39 (1998)
Gunnewegh, E.A., Hoefnagel, A.J., van Bekkum, H.: Zeolite Catalysed Synthesis of Coumarin Derivatives. J. Mol. Catal. A: Chem. 100, 87–92 (1995)
Horning, E.C.: Organic Synthesis, vol. III, p. 281. Wiley, New York (1955)
Khaligh, N.G.: Synthesis of Coumarins via Pechmann Reaction Catalyzed by 3-Methyl-1-Sulfonic Acid Imidazolium Hydrogen Sulfate as an Efficient, Halogen-Free and Reusable Acidic Ionic Liquid. Catal. Sci. Technol. 2, 1633–1636 (2012)
Hoefnagel, A.J., Gunnewegh, E.A., Downing, R.S., Bekkum, H.V.: Synthesis of 7-Hydroxycoumarins Catalysed by Solid Acid Catalysts. J. Chem. Soc., Chem. Commun. 225 (1995)
Sudha, S., Venkatachalam, K., Priya, S.V., Mabel, J.H., Palanichamy, M., Murugesan, V.: Single Step Synthesis of Coumarin Derivatives over Al-MCM-41 and its Supported Catalysts under Solvent-Free Condition. J. Mol. Catal. A: Chem. 291, 22–29 (2008)
Sinhamahapatra, A., Sutradhar, N., Pahari, S., Bajaj, H.C., Panda, A.B.: Mesoporous Zirconium Phosphate: An Efficient Catalyst for the Synthesis of Coumarin Derivatives through Pechmann Condensation Reaction. Appl. Catal. A: Gen. 394, 93–100 (2011)
Kalita, P., Kumar, R.: Solvent-Free Coumarin Synthesis via Pechmann Reaction Using Solid Catalysts. Micropor. Mesopor. Mater. 149, 1–9 (2012)
Balasubramanian, V.V., Anand, C., Pal, R.R., Mori, T., Bohlmann, W., Ariga, K., Tyagi, A.K., Vinu, A.: Characterization and the Catalytic Applications of Mesoporous AlSBA-1. Micropor. Mesopor. Mater. 121, 18–25 (2009)
Venkatachalam, K., Palanichamy, M., Murugesan, V.: Acetalization of Heptanal over Al-SBA-1 Molecular Sieve. Catal. Commun. 12, 299–303 (2010)
Kao, H.-M., Cheng, C.-C.: Tetramethoxysilane as a Convenient Silicon Source for Phase Control of Cubic SBA-1 Mesostructures. Mater. Lett. 60, 2594–2599 (2006)
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Peng, M.M., Shin, D.S., Hemalatha, P., Ganesh, M., Palanichamy, M., Jang, H.T. (2012). AlSBA-1 Molecular Sieves: Synthesis, Characterization and Catalytic Application. In: Cho, Hs., Kim, Th., Mohammed, S., Adeli, H., Oh, Mk., Lee, KW. (eds) Green and Smart Technology with Sensor Applications. ICTSM SIA GST 2011 2012 2012. Communications in Computer and Information Science, vol 338. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-35251-5_16
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DOI: https://doi.org/10.1007/978-3-642-35251-5_16
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