Silicotungstic Acid Modified Bentonite: An Efficient Catalyst for Synthesis of Acetal Derivatives of Aldehydes and Ketones


Acetals and ketals are among the important materials of organic synthesis and as protecting agent of carbonyl functionality. A milder, efficient and green synthesis of acetals and ketals has been developed using Silicotungstic acid modified Bentonite (STA-Ben) as a catalyst. STA-Ben has been synthesized and characterized by various analytical techniques. It has been found to be an efficient and reusable catalyst for the synthesis of acetyl derivatives in excellent yields. In order to elucidate the efficiency of the STA-Ben as catalyst, reaction has also been performed using various catalysts. The reaction conditions (time and amount of catalyst) have been optimized using various catalysts. The products of the various reactions have been characterized by FT-IR, NMR.

Share and Cite:

R. Chaudhary and M. Datta, "Silicotungstic Acid Modified Bentonite: An Efficient Catalyst for Synthesis of Acetal Derivatives of Aldehydes and Ketones," Journal of Analytical Sciences, Methods and Instrumentation, Vol. 3 No. 4, 2013, pp. 193-201. doi: 10.4236/jasmi.2013.34025.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] J. Cossy, H. Rakotoarisoa, P. Kahnand and J. R. Desmurs, “A One-Pot Synthesis Of Functionalized 2,2-Disubstituted 2H-1-Benzopyrans,” Tetrahedron Letters, Vol. 39, No. 52, 1998, pp. 9671-9674.
[2] A. T. Khan, E. Mondal, P. R. Sahu and S. Islam, “Nickel(II) Chloride as an Efficient and Useful Catalyst for Chemoselective Thioacetalization of Aldehydes,” Tetrahedron Letters, Vol. 44, No. 5, 2003, pp. 919-922.
[3] P. Datta, H. B. Borate, A. Sudalai, T. Ravlndranathan and V. H. Deshpande, “Natural Kaolinitic Clay: A Remarkable Reusable Solid Catalyst for the Selective Functional Protection of Aldehydes and Ketones,” Tetrahedron Letters, Vol. 37, No. 26, 1996, pp. 4605-4608.
[4] B. K. Banik, M. Chapa, J. Marquez and Magda Cardona, “A Remarkable Iodine-Catalyzed Protection of Carbonyl Compounds,” Tetrahedron Letters, Vol. 46, No. 13, 2005, pp. 2341-2343.
[5] B. Perio, M. J. Dozias, P. Jacquault and J. Hamelin, “Solvent Free Protection of Carbonyl Group under Microwave Irradiation,” Tetrahedron Letters, Vol. 38, No. 45, 1997, pp. 7867-7870.
[6] S. K. De, “Cobalt(II)Chloride Catalyzed Chemoselective Thioacetalization of Aldehydes,” Tetrahedron Letters, Vol. 45, No. 5, 2004, pp. 1035-1036.
[7] J. W. Ralls, R. M. Dodson and B. Riegel, “Addition of Mercaptans to Unsaturated Steroid Ketones,” Journal of the American Chemical Society, Vol. 71, No. 10, 1949, pp. 3320-3325.
[8] E. Mondal, P. R. Sahu and A. T. Khan, “A Useful and Catalytic Method for Protection of Carbonyl Compounds into the Corresponding 1,3-Oxathiolanes and Deprotection to the Parent Carbonyl Compounds,” Synlett, Vol. 3, No. 3, 2002, pp. 463-467.
[9] P. K. Mandal and S. C. Roy,” Ceric Ammonium Nitrate as a Convenient Catalyst for Chemoselective Thioacetalisation,” Tetrahedron, Vol. 51, No. 28, 1995, pp. 7823-7828.
[10] S. Gogoi, J. C. Borah and N. C. Barua, “Montmorillonite K-10 Clay as an Efficient Solid Catalyst for Chemoselective Protection of Carbonyl Compounds as Oxathiolanes with 2-Mercaptoethanol,” Synlett, Vol. 9, No. 9, 2004, pp. 1592-1594.
[11] J. S. Yadav, B. V. S. Reddy and G. Kondaji, “Eco-Friendly and Highly Chemoselective 1,3-Oxathio-and 1,3-Dithioacetalization of Aldehydes Using Ionic Liquids,” Chemistry Letters, Vol. 32, No. 8, 2003, pp. 672-673.
[12] L. Jankovic and P. Komadel , “Metal Cation-Exchanged Montmorillonite Catalyzed Protection of Aromatic Aldehydes with Ac2O,” Journal of Catalysis, Vol. 218, No. 1, 2003, pp. 227-233.
[13] U. V. Desai, T. S. Thopate, D. M. Pore and P.P. Wadgaonkar, “An Efficient, Solvent-Free Method for the Chemoselective Synthesis of Acylals from Aldehydes and Their Deprotection Catalyzed by Silica Sulfuric Acid as a Reusable Solid Acid Catalyst,” Catalysis Communications, Vol. 7, No. 7, 2006, pp. 508-511.
[14] S. Chandrasekhar, M. Takhi, Y. R. Reddy, S. Mohapatra, C. R. Rao and K. V. Reddy, “Tacl5-Silicagel and Tacl5 as New Lewis Acid Systems for Selective Tetrahydropyranylation of Alcohols and Thioacetalisation, Trimerisation and Aldolisation of Aldehydes,” Tetrahedron, Vol. 53, No. 44, 1997, pp. 14997-15004.
[15] M. khenkin, L. Weiner and R. Neumann, “Selective Ortho Hydroxylation Of Nitrobenzene with Molecular Oxygen Catalyzed by the H5pv2mo10o40 Polyoxometalate,” Journal of the American Chemical Society, Vol. 127, No. 128, 2005, pp. 9988-9989.
[16] A. M. Khenkin and R. Neumann, “Oxygen Transfer from Sulfoxides: Selective Oxidation of Alcohols Catalyzed by Polyoxomolybdates,” The Journal of Organic Chemistry, Vol. 67, No. 20, 2002, pp. 7075-7079.
[17] T. Okuhara, N. Mizuno and M. Misono, “Catalytic Chemistry of Heteropoly Compounds,” Advances in Catalysis, Vol. 41, 1996, pp. 113-252.
[18] I. V. Kozhevnikov, “Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions,” Chemical Reviews, Vol. 98, No. 1, 1998, pp. 171-198.
[19] I. V. Kozhevnikov, “Fine Organic Synthesis with the Aid of Heteropolycompounds,” Russian Chemical Reviews, Vol. 62, No. 5, 1993, p. 473.
[20] I. V. Kozhevnikov, “Catalysts for Fine Chemicals, Catalysis by Polyoxometalates,” Wiley, Chichester, 2002.
[21] M. N. Timofeeva, “Acid Catalysis by Heteropoly Acids,” Applied Catalysis A: General, Vol. 256, No. 1-2, 2003, pp. 19-35.
[22] J. M. Adams, “Synthetic Organic Chemistry Using Pillared, Cation-Exchanged and Acid-Treated Montmorillonite Catalysts—A Review,” Applied Clay Science, Vol. 2, No. 4, 1987, pp. 309-342.
[23] G. Brain, A. Loupy and D. Villemin, “Microwave Activation of Reactions on Inorganic Solid Supports,” In: K. Smith, Ed., Solids Supports and Catalysis in Organic Synthesis, Ellis Horwood, Chichester, 1992, pp. 100-122.
[24] L. Fowden, R. M. Barrer and P. B. Tinker, “Clay Minerals: Their Structure, Behaviour and Use,” The Royal Society, London, 1984.
[25] E. González and A. Moronta, “The Dehydrogenation of Ethylbenzene to Styrene Catalyzed by a Natural and an Al-Pillared Clays Impregnated with Cobalt Compounds: A Comparative Study,” Applied Catalysis A: General, Vol. 258, No. 1, 2004, pp. 99-105.
[26] M. Kurian and S. Sugunan, “Characterisation of the Acid-Base Properties of Pillared Montmorillonites,” Microporous and Mesoporous Materials, Vol. 83, No. 1-3, 2005, pp. 25-34.
[27] H. J. Chae, I.-S. Nam, S. W. Ham and S. B. Hong, “Physicochemical Characteristics of Pillared Interlayered Clays,” Catalysis Today, Vol. 68, No. 1-3, 2001, pp. 31-40.
[28] B. Tyagi, C. D. Chudasama and R. V. Jasra, “Characterization of Surface Acidity of an Acid Montmorillonite Activated with Hydrothermal, Ultrasonic and Microwave Techniques,” Applied Clay Science, Vol. 31, No. 1-2, 2006, pp. 16-28.
[29] P. Salerno, M. B. Asenjo and S. Mendioroz, “Influence of Preparation Method on Thermal Stability and Acidity of Al–PILCs,” Thermochimica Acta, Vol. 379, No. 1-2, 2001, pp. 101-109.
[30] W. O. Parker and I. Kiricsi Jr., “Aluminum Complexes in Partially Hydrolyzed Aqueous A1C13 Solutions Used to Prepare Pillared Clay Catalysts,” Applied Catalysis A, Vol. 121, No. 1, 1995, pp. L7-L11.
[31] E. M. Araujo, T. J. A. Melo, L. N. L. Santana, G. A. Neves, H. C. Ferreira, H. L. Lira, L. H. Carvalho, M. M. Avila Jr., M. K. G. Ponte and I. S. Araujo, “The Influence of Organo-Bentonite Clay on The Processing and Mechanical Properties of Nylon 6 and Polystyrene Composites,” Materials Science and Engineering: B, Vol. 112, No. 2-3, 2004, pp. 175-178.
[32] J. L. Valverde, P. Canizares, M. R. Sun Kou and C. B. Molina, “Enhanced Thermal Stability of Al-Pillared Smectites Modified with Ce and La,” Clays and Clay Minerals, Vol. 48, No. 4, 2000, pp. 424-432.
[33] M. M. M. Abd El-Wahab and A. A. Said, “Phosphomolybdic Acid Supported on Silica Gel and Promoted with Alkali Metal Ions as Catalysts for the Esterification of Acetic Acid By Ethanol,” Journal of Molecular Catalysis A: Chemical, Vol. 240, No. 1-2, 2005, pp. 109-118.
[34] N. Yildiz, Z. Aktas and A. Calimli, “Sulphuric Acid Activation of a Calcium Bentonite,” Particulate Science and Technology, Vol. 22, No. 1, 2004, pp. 21-33.
[35] J. Temuujin, Ts. Jadambaa, G. Burmaa, Sh. Erdenechimeg and J. Amarsanaa, “Characterisation of Acid Activated Montmorillonite Clay from Tuulant (Mongolia),” Ceramics International, Vol. 30, No. 2, 2004, pp. 251-255.

Copyright © 2023 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.