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Friedel–Crafts acylation of toluene using superacid catalysts in a solvent-free medium

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Abstract

Sulfated tin oxide and sulfated zirconia containing different amounts of sulfate and Al2O3-sulfated zirconia catalysts were prepared. The materials were characterized by DTA/TGA/DTG, XRD, FT-IR, and BET surface-area techniques. Surface acidity was determined using TGA of pyridine-pretreated samples, and acid strength was determined by potentiometric titration of the solid catalysts with n-butylamine in non-aqueous media. The catalytic activity of prepared samples was tested by Friedel–Crafts acylation of toluene with acetic acid anhydride. Incorporation of sulfate into SnO2 impedes sintering and is associated with a decrease of surface area. Sulfated tin oxide has greater acidity and higher acid strength than Al3+-impregnated sulfated zirconia, giving, therefore, a higher yield of acylation products. Sulfated tin oxide was found to pass through maxima of higher acidity and higher efficiency for the acylation reaction when sulfate loading is 10 wt%. A good relationship between structural characteristics, acidity, and catalytic activity is observed.

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Acknowledgments

Financial support (project number 8058) by the deanship of scientific research at King Faisal University is gratefully acknowledged.

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Authors and Affiliations

  1. Chemistry Department, College of Science, King Faisal University, P. O. Box 400, Hofuf, 31982, Saudi Arabia

    E. A. El-Sharkawy & Shar S. Al-Shihry

  2. Chemistry Department, College of Education at Al-Ariesh, Suez Canal University, Ismailia, Egypt

    E. A. El-Sharkawy

Authors
  1. E. A. El-Sharkawy
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  2. Shar S. Al-Shihry
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Correspondence to E. A. El-Sharkawy.

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El-Sharkawy, E.A., Al-Shihry, S.S. Friedel–Crafts acylation of toluene using superacid catalysts in a solvent-free medium. Monatsh Chem 141, 259–267 (2010). https://doi.org/10.1007/s00706-010-0250-3

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  • DOI: https://doi.org/10.1007/s00706-010-0250-3

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