Abstract
The synthesis of phenoxymethyl ethylene carbonate (PMEC) from carbon dioxide and phenyl glycidyl ether (PGE) was investigated using styrene-vinylbenzylchloride-montmorillonite supported quaternary ammonium salt catalysts. The catalysts were prepared by grafting the copolymer of styrene (ST) and vinylbenzyl chloride (VBC) onto montmorillonite (MMT) interlayers, followed by the quaternization using trialkylamines. The influence of VBC concentration, the structure of trialkylamine, and the type of support on the catalytic activity was discussed. Quaternary ammonium salt grafted onto organophilic ST-VBC-MMT intercalates showed higher conversion of PGE than that grafted onto montmorillonite interlayers since the former exhibits greater affinity for organic solvents than the latter does.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Akelah, A. and Moet, A., “Functionalized Polymers and Their Applications,” Chapmann & Hall, London (1990).
Akelah, A., Rehab, A., Selim, A. and Agag, T., “Synthesis and Application of Organophilic Polystyrene-Montmorillonite Supported Onium Salts in Organic Reactions,”J. Mol. Catal.,94, 311 (1994).
Awate, S.V., Waghmode, S. B., Patil, K. R., Agashe, M. S. and Joshi, P. N., “Influence of Preparation Parameters on Charactristics of Zirconia-Pillared Clay Using Ultrasonic Technique and its Catalytic Performance in Phenol Hydroxylation Reaction,”Korean J. Chem. Eng.,18, 257 (2001).
Clark, J.H., Tavener, S. J. and Barlow, S. J., “Preparation and Unusual Decomposition of Silica Supported Tetraphenylphosphonium Bromide,”J. Mater. Chem.,5, 827 (1995).
Ford, W. T., “Immobilized Phase-Transfer Catalysts,”Chem. Technol.,14, 436 (1984).
Kihara, N., Hara, N. and Endo, T., “Catalytic Activity of Various Salts in the Reaction of 2,3-Epoxypropyl Phenyl Ether and Carbon Dioxide under Atmospheric Pressure,”J. Org. Chem.,58, 6198 (1993).
Kim, B. S., Lee, S.H., Park, Y. T., Ham, S.W., Chae, H. J. and Nam, I. S., “Selective Catalytic Reduction of NOx by Propene over Copper-Exchanged Pillared Clays,”Korean J. Chem. Eng.,18, 704 (2001).
Kim, J. J., Shin, D.H. and Park, D.W., “Soluble Polymer-bound Quaternary Ammonium Salts for the Addition Reaction of Glycidyl Methacrylate with Carbon Dioxide,”Polym. Adv. Tech., submitted for publication (2002).
Kuran, G.W. and Marciniak, B. P., “Cyclic Carbonates from Carbon Dioxide and Oxiranes,”Monat. Chem.,115, 205 (1984).
Monsef-Mirzai, P. and McWhinnie, W., “Clay Supported Catalysts: an Extension of Phase Transfer Catalysis,”Inorg. Chim. Acta.,52, 211 (1981).
Moon, J.Y., Yang, J. G., Jung, S. M., Park, D.W. and Lee, J. K., “Application of Quaternary Ammonium Salt as Catalyst in the Reaction of Glycidyl Methacrylate with CO2,”Korean J. Chem. Eng.,14, 507(1997).
Moon, J.Y., Jang, H. J., Kim, K.H., Na, S. E., Park, D.W. and Lee, J.K., “Chemical Fixation of Carbon Dioxide to Copolymers Bearing Cyclic Carbonate Group,”Korean J. Chem. Eng.,16, 721 (1999).
Moronta, A., Ferrer, V., Quero, J., Arteaga, G. and Choren, E., “Influence of Preparation Method on the Catalytic Properties of Acid-Activated Tetramethylammonium-exchanged Clays,”Appl. Catal. A: Gen.,230, 127 (2002).
Nishikubo, T., Kato, T., Sugimoto, S., Tomoi, M. and Ishigaki, S., “Spacer-Modified Polymeric Catalysts Containing Phosphonium Salts for a Regioselective Addition Reaction of Epoxy Compounds with Active Esters,”Macromolecules,23, 3406 (1990).
Nishikubo, T., Kameyama, A., Yamashita, I., Tomoi, M. and Fukuda, W., “Insoluble Polystyrene-bound Quaternary Onium Salt Catalysts for the Synthesis of Cyclic Carbonates by the Reaction of Oxiranes with Carbon Dioxide,”J. Polym. Sci., A: Polym. Chem.,31, 939 (1993).
Nomura, R., Ninagawa, A. and Matsuda, H., “Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides in the Presence of Organoantimony Compounds as Novel Catalysts,”J. Org. Chem.,45, 3735 (1980).
Park, D.W., Moon, J.Y., Yang, J. G., Jung, S.M., Lee, J.K. and Ha, C. S., “Catalytic Conversion of Carbon Dioxide to Polymer Blends via Cyclic Carbonates,”Stud. Surf. Sci. Catal.,114, 403 (1998).
Pinnavaia, T. J., “Intercalated Clay Catalysts,”Science,220, 365 (1983).
Sasson, Y. and Neumann, R., “Handbook of Phase Transfer Catalysis,” Blackie Academic & Professional, New York (1997).
Starks, C.M., Liotta, C. L. and Halpern, M., “Phase Transfer Catalysis,” Chapman & Hall, New York (1994).
Tomoi, M., Kori, N. and Kakiuchi, H., “Phase-Transfer Catalytic Activity of Phosphonium Salts Bound to Microporous Polystyrene Resins by Long Spacer Chains,”Makromal. Chem.,187, 2753 (1986).
Tundo, P. and Venturello, P., “Polymer-Supported Phase-Transfer Catalysts. High Catalytic Activity of Ammonium and Phosphonium Quaternary Salts Bonded to a Polystyrene Matrix,”J. Am. Chem. Soc.,101, 3920 (1979).
Tundo, P., Venturello, P. and Angeletti, E., “Quaternary Onium Salts Immobilized on Inorganic Matrices,”Isr. J. Chem.,26, 283 (1985).
Varma, R. S. and Naicker, K. P., “Surfactant Pillared Clays in Phase Transfer Catalysis: A New Route to Alkyl Azides from Alkyl Bromides and Sodium Azide,”Tetrahedron Lett.,39, 2915 (1998).
Venturello, P., Tundo, P. and Angeletti, E., “Phase-Transfer Catalysts Immobilized and Adsorbed on Alumina and Silica Gel,”J. Am. Chem. Soc.,104, 6547 (1982).
Wang, M. L. and Peng, C. Z., “Effect of Some Structural Features of the Polymer Support on Synthesizing 2,4,6-Tribromophenyl Benzyl Ether in a Triphase Catalysis,”Polym. Int.,34, 187(1994).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shin, DH., Kim, JJ., Yu, BS. et al. Synthesis of phenoxymethyl ethylene carbonate using quaternary ammonium salt catalysts grafted onto styrene-vinylbenzylchloride-montmorillonite support. Korean J. Chem. Eng. 20, 71–76 (2003). https://doi.org/10.1007/BF02697187
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02697187