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Issue 25, 2009
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Study of the Beckmann rearrangement of acetophenone oxime over porous solids by means of solid state NMR spectroscopy

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Abstract

The Beckmann rearrangement of acetophenone oxime using zeolite H-beta and silicalite-N as catalysts has been investigated by means of 15N and 13C solid state NMR spectroscopy in combination with theoretical calculations. The results obtained show that the oxime is N-protonated at room temperature on the acid sites of zeolite H-beta. At reaction temperatures of 423 K or above, the two isomeric amides, acetanilide and N-methyl benzamide (NMB) are formed, and interact with the Brønsted acid sites of zeolite H-beta through hydrogen bonds. The presence of residual water hydrolyzes the two amides, while larger amounts inhibit the formation of NMB and cause the total hydrolysis of the acetanilide. Over siliceous zeolite silicalite-N, containing silanol nests as active sites, the oxime is adsorbed through hydrogen bonds and only acetanilide is formed at reaction temperatures of 423 K or above. In the presence of water, the reaction starts at 473 K, still being very selective up to 573 K, and the amide is partially hydrolyzed only above this temperature .

Graphical abstract: Study of the Beckmann rearrangement of acetophenone oxime over porous solids by means of solid state NMR spectroscopy

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Article information


Submitted
17 Sep 2008
Accepted
02 Mar 2009
First published
02 Apr 2009

Phys. Chem. Chem. Phys., 2009,11, 5134-5141
Article type
Paper

Study of the Beckmann rearrangement of acetophenone oxime over porous solids by means of solid state NMR spectroscopy

A. B. Fernandez, I. Lezcano-Gonzalez, M. Boronat, T. Blasco and A. Corma, Phys. Chem. Chem. Phys., 2009, 11, 5134
DOI: 10.1039/B816276J

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