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Issue 5, 2016
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Chemoselective hydrogenation of 3-nitrostyrene over a Pt/FeOx pseudo-single-atom-catalyst in CO2-expanded liquids

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Abstract

Chemoselective hydrogenation of substituted nitroarenes containing two reducible groups in one molecule is a highly desired approach to the synthesis of functionalized anilines. To make this process environmentally benign, we used a pseudo-single-atom-catalyst Pt/FeOx and investigated the reaction in supercritical CO2 and CO2-expanded toluene. The results showed that supercritical CO2 afforded excellent selectivity but low reactivity due to the limited substrate solubility in the reaction medium. By contrast, when the reaction proceeded in CO2 expanded toluene, both the conversion of 3-nitrostyrene and the selectivity of 3-vinylaniline reached above 95% under optimum conditions while the organic toluene amount could be reduced by 90% compared to that without CO2. The thermodynamic calculations revealed that the solubility of H2 increased while the viscosity of the reaction system decreased with the CO2 pressure, which facilitated the mass transfer and therefore increased the reaction rate meanwhile keeping the selectivity at a high level.

Graphical abstract: Chemoselective hydrogenation of 3-nitrostyrene over a Pt/FeOx pseudo-single-atom-catalyst in CO2-expanded liquids

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Supplementary files

Article information


Submitted
15 Aug 2015
Accepted
08 Oct 2015
First published
09 Oct 2015

Green Chem., 2016,18, 1332-1338
Article type
Paper
Author version available

Chemoselective hydrogenation of 3-nitrostyrene over a Pt/FeOx pseudo-single-atom-catalyst in CO2-expanded liquids

G. Xu, H. Wei, Y. Ren, J. Yin, A. Wang and T. Zhang, Green Chem., 2016, 18, 1332
DOI: 10.1039/C5GC01914A

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