Zeolite-assisted regioselective mononitration of naphthalene with nitrogen dioxide/molecular oxygen

Zeolite-assisted regioselective mononitration of naphthalene with nitrogen dioxide/molecular oxygen The nitration process using nitrogen dioxide and oxygen instead of the classical nitric acid–sulfuric acid system appears to be attractive and promising in the selective preparation of nitro compounds. The ratio of 1-nitronaphthalene isomer to 2-nitronaphthalene can reach 11 in a moderate yield of 60 % when the reaction is carried out in acetonitrile with 5.0 mmol naphthalene, 10 mmol nitrogen dioxide, and 0.13 g HZSM-5 under molecular oxygen atmosphere at −15 °C. The isomeric distribution of the product nitro-naphthalene was found to be superior to traditional methods. The zeolite could be easily regenerated and recycled and reused by simple work-up to give results similar to those obtained with the fresh catalyst. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Zeolite-assisted regioselective mononitration of naphthalene with nitrogen dioxide/molecular oxygen

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Publisher
Springer Netherlands
Copyright
Copyright © 2012 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-012-0827-z
Publisher site
See Article on Publisher Site

Abstract

The nitration process using nitrogen dioxide and oxygen instead of the classical nitric acid–sulfuric acid system appears to be attractive and promising in the selective preparation of nitro compounds. The ratio of 1-nitronaphthalene isomer to 2-nitronaphthalene can reach 11 in a moderate yield of 60 % when the reaction is carried out in acetonitrile with 5.0 mmol naphthalene, 10 mmol nitrogen dioxide, and 0.13 g HZSM-5 under molecular oxygen atmosphere at −15 °C. The isomeric distribution of the product nitro-naphthalene was found to be superior to traditional methods. The zeolite could be easily regenerated and recycled and reused by simple work-up to give results similar to those obtained with the fresh catalyst.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 5, 2012

References

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