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Metal-Free Reduction of Nitrobenzene to Aniline in Subcritical Water

Authors :: Rafael Luque
Denis Luart
Christophe Len
Sarra Tadrent
Olivier Bals
Anissa Khelfa
Transformation Intégrée de la Matière Renouvelable (TIMR)
Université de Technologie de Compiègne (UTC)
ESCOM
Departamento de Quimica Organica [Universidad de Cordoba]
Universidad de Córdoba [Cordoba]
Institut de Recherche de Chimie Paris (IRCP)
Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP)
Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ministère de la Culture (MC)
Source :: Journal of Organic Chemistry, Journal of Organic Chemistry, American Chemical Society, 2018, 83 (14), pp.7431--7437. ⟨10.1021/acs.joc.8b00406⟩
Publication Year :: 2018
Publisher :: American Chemical Society (ACS), 2018.
Abstract: An environmentally friendly approach for the reduction of nitrobenzene to aniline promoted by carbonaceous bio-based materials was successfully achieved under subcritical water conditions. The proposed methodology features a metal-free process, no-hydrogen input as reductor, the use of commercial bio-based carbon materials having low cost and availability, and water as green solvent under subcritical conditions. Using optimized conditions, reduction of nitrobenzene in the presence of commercial NORIT GAC 12-40 or DACARB PC1000 was accomplished at 310 °C for 6 h and quantitatively furnished the target aniline. Treatment of NORIT GAC 12-40 with KOH allowed to decrease charcoal loading (6 g vs 40 g) and increase aniline yields (80% vs 66%).