A study on the selective hydrogenation of nitroaromatics to N-arylhydroxylamines using a supported Pt nanoparticle catalyst

Evert H. Boymans, P. T. Witte, D. Vogt

Research output: Contribution to journalArticlepeer-review

Abstract

A supported Pt nanoparticle-based catalyst was used in the chemoselective hydrogenation of nitroarenes to N-arylhydroxylamines (N-AHA). Optimization of NB hydrogenation conditions showed that substantially higher N-PHA yields can be obtained at low temperature. Especially, the influence of an increased hydrogen pressure on selectivity is remarkable. Maximum yields increase from 55% N-PHA at 4 bar H2 to 80% at 23 bar H2 in ethanol. Further optimization led to the use of small amounts of amine additive, TMEDA, with 50 bar H2 raising the maximum yield to 97% N-PHA. The decreased N-PHA hydrogenation rate at high H2 pressure and the presence of TMEDA allow for selective transformation of a range of other nitroarenes containing electron-withdrawing and -donating (reducible) functional groups to their N-AHAs in excellent (more than 90%) yields.
Original languageEnglish
Pages (from-to)176-183
JournalCatalysis Science & Technology
Volume5
Issue number1
Early online date29 Aug 2014
DOIs
Publication statusPublished - 1 Jan 2015

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