Abstract
O-alkylation reaction of hydroquinone with excess methanol was performed by using alkali metal ion-exchanged zeolite catalysts in a slurry type reactor to substitute the solid zeolite catalysts for the homogeneous liquid phase catalysts. This was also done to produce selectively mono-alkylated 4-methoxyphenol, a valuable intermediate for the perfume, flavor, food and photo industries. The effects of the basicity of various zeolites and reaction conditions such as temperature, reaction time and the amount of catalyst on the catalytic activity and selectivity were tested to maximize the yield of 4-methoxyphenol. Thus far, 84% selectivity at 95% conversion of hydroquinone was obtained at the optimum reaction conditions (240 ‡C, reaction with 0.6 g catalyst for 16 h), which was thought to result from the strong basic property and shape selectivity of the Cs ion-exchanged NaX zeolite.
Similar content being viewed by others
References
Bautista, F. M., Campelo, J. M., Luna, A. G. D., Marinas, J. M., Romero, A., Navio, J. A. and Macias, M., “Anion Treatment (F- or SO 24 ) of A1PO4-A12O3 (25 wt.-% A12O3) Catalysts. IV. Catalytic Performance in the Alkylation of Phenol with Methanol”,Appl. Catal.,99, 161 (1993).
Breck, D. W., “Zeolite Molecular Sieves”, John Wiley & Sons, New York (1974).
Fu, Z. H. and Ono, Y., “Selective O-Methylation of Phenol with Dimethyl Carbonate over X-Zeolites”,Catal. Lett.,21, 43 (1993).
Hattori, H., “Heterogeneous Basic Catalysis”,Chem. Rev.,95, 537 (1995).
Iglesia, E., Barton, D. G., Biscardi, J. A., Gines, M. J. L. and Soled, S. L., “Bifunctional Pathways in Catalysis by Solid Acids and Bases”,Catal. Today,38, 339 (1997).
Imelik, B., Naccache, C., Coudurier, G., Taarit, Y. B. and Vedrine, J. C., “Catalysis by Acids and Bases”, Elsevier Science Publishers B. V., Amsterdam (1985).
Kim, J. C., Li, H. X., Chen, C. Y. and Davis, M. E., “Base Catalysis by Intrazeolitic Cesium Oxides”,Micro. Mat.,2, 413 (1994).
Kim, M. W., Kim, J. H., Sugi, Y. and Seo, G., “Shape-Selective Alkylation of Isopropylnaphthalene on MCM-22 Zeolite”,Korean J. Chem. Eng.,17, 480 (2000).
Lee, S. C., Lee, S. W., Kim, K. S., Lee, T. J., Kim, D. H. and Kim, J. C., “O-Alkylation of Phenol Derivatives over Basic Zeolites”,Catal. Today,44, 253 (1998).
Lee, S. W., Kim, D. H., Kim, K. S., Lee T. J. and Kim, J. C., “Synthesis of Anisole from Phenol by Using a Solid Base Catalyst”,HWAHAK KONGHAK,35, 621 (1997).
Ono, Y. and Baba, T., “Selective Reactions over Solid Base Catalysts”,Catal. Today,38, 321 (1997).
Samolada, M. C., Grioriadou, E., Kiparissides, Z. and Vasalos, I. A., “Selective O-alkylation of Phenol with Methanol over Sulphates Supported on γ-Al2O3”,J. Catal.,152, 52 (1995).
Tleimat-Manzalji, R., Bianchi, D. and Pajonk, G. M., “Catalytic Alkylation of Phenol with Methanol on a Microporous Xerogel and a Macroporous Aerogel of High Surface Area Aluminas”,Appl. Catal., A,101, 339 (1993).
Yoshihiro, S., “Shape-Selective Alkylation of Biphenyl Catalyzed by H-Mordenites”,Korean J. Chem. Eng.,17, 1 (2000).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, S.S., Lee, S.C. & Kim, J.C. Selective O-Alkylation Reaction of Hydroquinone with Methanol over Cs Ion-Exchanged Zeolites. Korean J. Chem. Eng. 19, 406–410 (2002). https://doi.org/10.1007/BF02697147
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02697147