MOF-Derived Cu-Nanoparticle Embedded in Porous Carbon for the Efficient Hydrogenation of Nitroaromatic Compounds
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MOF‑Derived Cu‑Nanoparticle Embedded in Porous Carbon for the Efficient Hydrogenation of Nitroaromatic Compounds Chenxia Qiao1 · Wenlan Jia1 · Qiming Zhong1 · Bingyu Liu1 · Yifu Zhang1 · Changgong Meng1 · Fuping Tian1 Received: 14 January 2020 / Accepted: 28 April 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Novel Cu-nanoparticles (NPs) embedded in porous carbon materials (Cu@C-x) were prepared by one-pot pyrolysis of metal–organic frameworks (MOF) HKUST-1 at different temperatures. The obtained material Cu@C-x was used as a costeffective catalyst for the hydrogenation of nitrobenzene using NaBH4 as the reducing agent under mild reaction conditions. By considering the catalyst preparation and the catalytic activity, a pyrolysis temperature of 400 °C was finally chosen to synthesize the optimal catalyst. When the aromatic nitro compounds with reducible groups, such as cyano, halogen, and alkyl groups, were tested in this catalytic hydrogenation, an excellent selectivity approaching 100% was achieved. In the recycling experiment, a significant decrease in nitrobenzene conversion was observed in the third cycle, mainly due to the very small amount of catalyst employed in the reaction. Hence, the easily prepared and cost-effective Cu@C-400 catalyst fabricated in this study demonstrates potential for the applications in selective reduction of aromatic nitro compounds. Graphic Abstract The catalyst Cu@C-400 exhibited 100 % conversion and high selectivity for the hydrogenation of industrially relevant nitroarenes.
Keywords Cu@c-400 · Reduction · Aromatic nitro compounds
1 Introduction Chenxia Qiao and Wenlan Jia have contributed equally to this paper. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-020-03244-6) contains supplementary material, which is available to authorized users. * Fuping Tian [email protected] 1
State Key Laboratory of Fine Chemicals & Department of Chemistry, Dalian University of Technology, 2 Linggong Road, P. O. Box 288, Dalian 116024, China
Selective reduction of nitro compounds into amines is one of the most important chemical reactions in synthetic organic chemistry [1, 2]. Amines have been widely used for the production of bulk and fine chemicals, such as dyes, agrochemicals, pharmaceuticals, pesticides, and polymers [3–5]. The extensively employed method for the production of anilines is the direct reduction of the corresponding aromatic nitro compounds [6–10]. Generally, the catalytic reduction of nitro compounds with hydrogen or hydrogen donors has been mainly performed over noble metal
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catalysts (for example, Ru, Pt, Pd, etc.) [11, 12], but the scarcity of these noble metals and the high price heavily limit their large-scale industrial applications. Moreover, the presence of other reducible functional groups in the nitroarenes makes the selective reduction of the nitro group quite challenging. As an alternative choice, the heterogeneous catalysts based on the
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