Molecular modeling studies on zeolite catalysts for shape-selective electrophilic substitution: I acylation of 2-methoxynaphthalene

Bharathi, Patibandla ; Waghmode, Suresh B. ; Sivasanker, Subramanian ; Vetrivel, Rajappan (1999) Molecular modeling studies on zeolite catalysts for shape-selective electrophilic substitution: I acylation of 2-methoxynaphthalene Bulletin of the Chemical Society of Japan, 72 (10). pp. 2161-2167. ISSN 0009-2673

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Official URL: http://www.jstage.jst.go.jp/article/bcsj/72/10/72_...

Related URL: http://dx.doi.org/10.1246/bcsj.72.2161

Abstract

The diffusion characteristics of acylated 2-methoxynaphthalene inside large pore zeolites were investigated. The interaction of the three isomers with fully siliceous zeolite lattices was studied by energy-minimization calculations. The favorable adsorption sites and the orientation of the acylated products of 2-methoxynaphthalene were analyzed in detail. Three large pore zeolites having 12 m channels were selected: (i) mordenite with an elliptical 1-d channel, (ii) zeolite-L with a circular channel and 2-d cages, and (iii) zeolite-β with circular 3-d channel systems. It was observed that the shape selectivity properties of the zeolites could be profitably used to produce 2-acyl-6-methoxynaphthalene. In the case of mordenite, the diffusion of all three isomers is facile, whereas in the case of zeolite-L, the diffusion of 1-acyl-7-methoxynaphthalene is more facile than 2-acyl-6-methoxynaphthalene and 1-acyl-2-methoxynaphthalene. In the case of zeolite-β, the energy barrier for the diffusion of 2-acyl-6-methoxynaphthalene is significantly smaller than those of the other two isomers. Thus zeolite-β is predicted to be a suitable catalyst for the shape-selective acylation of 2-methoxynaphthalene to 2-acyl-6-methoxynaphthalene.

Item Type:Article
Source:Copyright of this article belongs to Chemical Society of Japan.
ID Code:47741
Deposited On:12 Jul 2011 14:35
Last Modified:12 Jul 2011 14:35

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