Abstract
A kinetic study of phenyl acetate transformation was carried out in a batch reactor over a HBEA zeolite (framework Si/Al ratio of 11) at 160°C, sulfolane orn-dodecane being used as solvents. Whatever the solvent, phenyl acetate undergoes a monomolecular rearrangement intoo-hydroxyacetophenone, an autoacylation intop-acetoxyacetophenone plus phenol and a hydrolysis into phenol.p-hydroxyacetophenone which appears as a secondary product results from the acylation of phenol with phenyl acetate. The initial reaction rates and the product distribution depend very much on the solvent. This can be explained by the large difference in the strength of adsorption between the polar sulfolane and the non-polar dodecane solvents on the active acid sites.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
P.B. Venuto and P.S. Landis, Adv. Catal. 18 (1968) 259.
Y. Pouilloux, N.S. Gnep, P. Magnoux and G. Pérot, J. Mol. Catal. 40 (1987) 231.
C.S. Cundy, R. Higgins, S.H.M. Kibby, B.M. Lowe and R.M. Paton, Tetrahedron Lett. 30 (1989) 2281.
Y. Pouilloux, J.P. Bodibo, I. Neves, M. Gubelmann, G. Pérot and M. Guisnet, Stud. Surf. Sci. Catal. 59 (1991) 513.
A.H.G. Vogt and H.W. Kouwenhoven, Coll. Czech. Chem. Commun. 57 (1992) 853.
G. Harvey, A.H.G. Vogt, H.W. Kouwenhoven and R. Prins, in:Proc. 9th Int. Zeolite Conf., Vol. II, Montreal 1992, eds. R. Von Ballmoos et al. (1993) p. 363.
H. van Bekkum, A.J. Hoefnagel, M.A. van Koten, E.A. Gunnewegh, A.H.G. Vogt and H.W. Kouwenhoven, Stud. Surf. Sci. Catal. 83 (1994) 379.
A.H.G. Vogt, H.W. Kouwenhoven and R. Prins, Appl. Catal. A 123 (1995) 37.
I. Neves, F.R. Ribeiro, J.P. Bodibo, Y. Pouilloux, M. Gubelmann, P. Magnoux, M. Guisnet and G. Pérot, in:Proc. 9th Int. Zeolite Conf., Vol. II, Montreal 1992, eds. R. Von Ballmoos et al. (1993) p. 543.
I. Neves, F. Jayat, P. Magnoux, G. Pérot, F.R. Ribeiro, M. Gubelmann and M. Guisnet, J. Mol. Catal. 93 (1994) 169.
I. Neves, F. Jayat, P. Magnoux, G. Pérot, F.R. Ribeiro, M. Gubelmann and M. Guisnet, J. Chem. Soc. Chem. Commun. (1994) 717.
M. Guisnet, D.B. Lukyanov, F. Jayat, P. Magnoux and I. Neves, Ind. Eng. Chem. Res. 34 (1995) 1624.
I. Neves, F. Jayat, D.B. Lukyanov, P. Magnoux, G. Pérot, F.R. Ribeiro, M. Gubelmann and M. Guisnet, in:Catalysis of Organic Reactions, eds. M.G. Scaros and M.L. Prunier (Dekker, New York, 1995) p. 515.
I. Neves, P. Magnoux and M. Guisnet, Bull. Soc. Chim. Fr. 132 (1995) 156.
L. Gilbert and C. Mercier, Stud. Surf. Sci. Catal. 78 (1993) 51.
P.H.J. Espeel, K.A. Vercruysse, M. Debaerdemaker and P.A. Jacobs, Stud. Surf. Sci. Catal. 84 (1994) 1457.
K.R. Lassila and M.E. Ford, in:Catalysis of Organic Reactions, ed. W.E. Pascoe (Dekker, New York, 1992) p. 169.
A.I. Vogel,Textbook of Practical Organic Chemistry, 4th Ed. (Longmans, London, 1978) p. 138.
F. Jayat and M. Guisnet, unpublished.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Jayat, F., Picot, M.J.S. & Guisnet, M. Solvent effects in liquid phase Fries rearrangement of phenyl acetate over a HBEA zeolite. Catal Lett 41, 181–187 (1996). https://doi.org/10.1007/BF00811488
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00811488