Highly efficient light-driven HNO3 nitration–oxidation of cyclohexane to co-product nitrocyclohexane and adipic acid in a biphasic system

Highly efficient light-driven HNO3 nitration–oxidation of cyclohexane to co-product... Co-production of nitrocyclohexane and adipic acid by light-driven nitric acid (HNO3) nitration–oxidation of cyclohexane in an aqueous biphasic system was designed as a potential method for safe synthesis, because the reaction can be carried out at mild conditions (1 atmosphere, 298 K, and solvent-free media). In this process, we find that ultraviolet (UV) irradiation (λ = 365 nm) of a cyclohexane/HNO3 mixture in a N2 atmosphere efficiently produces nitrocyclohexane and adipic acid with total selectivity (ca. 87 %) at a 22 % conversion rate. Nitration–oxidation of cyclohexane is initiated by an ·OH from the direct photolysis of nitric acid. A reaction scheme has been proposed to explain the process and the different concentrations of nitric acid involved with the formation of the different reaction products. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Highly efficient light-driven HNO3 nitration–oxidation of cyclohexane to co-product nitrocyclohexane and adipic acid in a biphasic system

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Publisher
Springer Netherlands
Copyright
Copyright © 2015 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-015-2030-5
Publisher site
See Article on Publisher Site

Abstract

Co-production of nitrocyclohexane and adipic acid by light-driven nitric acid (HNO3) nitration–oxidation of cyclohexane in an aqueous biphasic system was designed as a potential method for safe synthesis, because the reaction can be carried out at mild conditions (1 atmosphere, 298 K, and solvent-free media). In this process, we find that ultraviolet (UV) irradiation (λ = 365 nm) of a cyclohexane/HNO3 mixture in a N2 atmosphere efficiently produces nitrocyclohexane and adipic acid with total selectivity (ca. 87 %) at a 22 % conversion rate. Nitration–oxidation of cyclohexane is initiated by an ·OH from the direct photolysis of nitric acid. A reaction scheme has been proposed to explain the process and the different concentrations of nitric acid involved with the formation of the different reaction products.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Apr 10, 2015

References

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