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Dehydration of aldoximes on rare earth exchanged (La3+, Ce3+, RE3+, Sm3+) Na–Y zeolites: A facile route for the synthesis of nitriles

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Abstract

Rare earth exchanged Na–Y zeolites, H-mordenite, K-10 montmorillonite clay and amorphous silica-alumina were effectively employed for the continuous synthesis of nitriles. Dehydration of benzaldoxime and 4-methoxybenzaldoxime were carried out on these catalysts at 473 K. Benzonitrile (dehydration product) was obtained in near quantitative yield with benzaldoxime whereas; 4-methoxybenzaldoxime produces both Beckmann rearrangement (4-methoxyphenylformamide) as well as dehydration products (4-methoxy benzonitrile) in quantitative yields. The production of benzonitrile was near quantitative under heterogeneous reaction conditions. The optimal protocol allows nitriles to be synthesized in good yields through the dehydration of aldoximes. Time on stream (TOS) studies show decline in the activity of the catalysts due to neutralization of acid sites by the basic reactant and product molecules and water formed during the dehydration of aldoximes.

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Acknowledgments

The aldoximes and authentic samples of nitriles employed in this study were prepared by undergraduate students of this department as part of their Organic Chemistry Laboratory course. The authors are grateful to Dr. C. V. Asokan, School of Chemical Sciences, Mahatma Gandhi University, Kottayam for providing the GC-MS results. B. Thomas is grateful to Council of Scientific and Industrial Research for Senior Research Fellowship.

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  1. Bejoy Thomas

    Present address: NMR Research Center, Indian Institute of Science, Bangalore, 560 012, India

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  1. Department of Applied Chemistry, Cochin University of Science and Technology, Kochi, 682 022, India

    Bejoy Thomas & S. Sugunan

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  1. Bejoy Thomas
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  2. S. Sugunan
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Correspondence to S. Sugunan.

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Thomas, B., Sugunan, S. Dehydration of aldoximes on rare earth exchanged (La3+, Ce3+, RE3+, Sm3+) Na–Y zeolites: A facile route for the synthesis of nitriles. J Porous Mater 14, 471–480 (2007). https://doi.org/10.1007/s10934-006-9042-x

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  • DOI: https://doi.org/10.1007/s10934-006-9042-x

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