Abstract
The liquid phase acylation of 2-methoxynaphthalene with acetic anhydride was carried out in a batch reactor at 120°C over a series of HBEA zeolites resulting from dealumination of a commercial sample by treatment with chlorhydric acid or with ammonium hexafluorosilicate. Lewis acid sites which correspond to extraframework aluminium species and to transient-state species (aluminium atoms which are leaving the framework) were preferentially removed. With all the HBEA samples, acetylation of 2-methoxynaphthalene leads preferentially to 1-acetyl-2-methoxynaphtalene, this compound undergoing isomerization into 2-acetyl-6-methoxynaphthalene and 1-acetyl-7-methoxynaphthalene as well as deacylation. A maximum in acetylation and isomerization activities is found for a Si/Al ratio between 20 and 35. The low activity of the commercial sample can be related to limitations in the desorption of acetylated products from the zeolite micropores caused by the large amount of extraframework aluminium species present on this sample. Lewis acid sites were shown to be completely inactive for acetylation and isomerization reactions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
H.G. Franck and J.W. Stadelhofer, Industrial Aromatic Chemistry (Springer, Berlin, 1988).
H.W. Kouwenhoven and H. van Bekkum, in: Handbook of Heterogeneous Catalysis, 5th Ed., eds. G. Ertl, H. Knözinger and J. Weitkamp (Wiley, New York, 1997) p. 2358.
E. Fromentin, J.-M. Coustard and M. Guisnet, J. Catal. 190 (2000) 433.
D. Martin, unpublished results.
E. Fromentin, J.-M. Coustard and M. Guisnet, J. Mol. Catal., to be published.
G. Harvey, G. Binder and R. Prins, Stud. Surf. Sci. Catal. 94 (1995) 397.
H.K. Heinichen and W.F. Hölderich, J. Catal. 185 (1999) 408.
M.A. Camblor and J. Perez-Pariente, Zeolites 11 (1991) 202.
C. Coutanceau, J.M. Da Silva, M.F. Alvarez, F.R. Ribeiro and M. Guisnet, J. Chem. Phys. 94 (1997) 765.
J.C. Jansen, E.J. Creyghton, S.L. Njo, H. van Koningsveld and H. van Bekkum, Catal. Today 38 (1997) 205.
C. Jice, P. Massiani and D. Barthomeuf, J. Chem. Soc. Faraday Trans. 89 (1993) 3659.
I. Kiricsi, C. Flego, G. Pazzuceni, W.O. Parker, Jv. Millini, R. Perego and G. Bellussi, J. Phys. Chem. 98 (1994) 4627.
E.J. Graythton, S.D. Ganeshie, R.S. Downing and H. van Bekkum, J. Chem. Soc. Chem. Commun. (1995) 1859.
E.J. Graythton, S.D. Ganeshie, R.S. Downing and H. van Bekkum, J. Mol. Catal. A 115 (1997) 457.
D.W. Breck, H. Blass and G.W. Skeels, US Patent 4 503 023 (1985)
G.W. Skeels and D.W. Breck, in: Proc. 6th Int. Zeolite Conf., Reno, Nevada, 1983, eds. D. Olson and A. Bisio (Butterworths, Gulford, 1984) p. 87.
A. Corma, V. Fornes, J.B. Monton and V. Orchilles, J. Catal. 107 (1987) 288.
M. Guisnet, P. Ayrault, C. Coutanceau, M.F. Alvarez and J. Datka, J. Chem. Soc. Faraday Trans. 93 (1997) 1661.
C. Garralon, V. Fornes and A. Corma, Zeolites 8 (1988) 268.
Q.L. Wang, M. Torrealba, G. Giannetto, M. Guisnet, G. Perot, M. Cahoreau and J. Caisso, Zeolites 10 (1990) 703.
D. Barthomeuf, Mater. Chem. Phys. 17 (1987) 49.
D. Barthomeuf, J. Phys. Chem. 97 (1993) 1092.
C. Mirodatos and D. Barthomeuf, J. Chem. Soc. Chem. Commun. (1981) 39.
F. Jayat, Ph.D. thesis, University of Poitiers, France (1996).
A. Berreghis, unpublished results.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Berreghis, A., Ayrault, P., Fromentin, E. et al. Acetylation of 2-methoxynaphthalene with acetic anhydride over a series of dealuminated HBEA zeolites. Catalysis Letters 68, 121–127 (2000). https://doi.org/10.1023/A:1019083420175
Issue Date:
DOI: https://doi.org/10.1023/A:1019083420175