Abstract
Selective hydrogenations of (hetero)arenes represent essential processes in the chemical industry, especially for the production of polymer intermediates and a multitude of fine chemicals. Herein, we describe a new type of well-dispersed Ru nanoparticles supported on a nitrogen-doped carbon material obtained from ruthenium chloride and dicyanamide in a facile and scalable method. These novel catalysts are stable and display both excellent activity and selectivity in the hydrogenation of aromatic ethers, phenols as well as other functionalized substrates to the corresponding alicyclic reaction products. Furthermore, reduction of the aromatic core is preferred over hydrogenolysis of the C–O bond in the case of ether substrates. The selective hydrogenation of biomass-derived arenes, such as lignin building blocks, plays a pivotal role in the exploitation of novel sustainable feedstocks for chemical production and represents a notoriously difficult transformation up to now.
Highlights
Selective hydrogenations ofarenes represent essential processes in the chemical industry, especially for the production of polymer intermediates and a multitude of fine chemicals
At the start of our work, we synthesized different ruthenium nanoparticles (Ru-NPs) immobilized on Vulcan powder (Ru@NDCs-X; X labels the pyrolysis temperature)
Further evidence of N-doping is provided by X-ray photoelectron spectroscopy (XPS)
Summary
Selective hydrogenations of (hetero)arenes represent essential processes in the chemical industry, especially for the production of polymer intermediates and a multitude of fine chemicals. We describe a new type of well-dispersed Ru nanoparticles supported on a nitrogen-doped carbon material obtained from ruthenium chloride and dicyanamide in a facile and scalable method These novel catalysts are stable and display both excellent activity and selectivity in the hydrogenation of aromatic ethers, phenols as well as other functionalized substrates to the corresponding alicyclic reaction products. For the consecutive utilization of such lignin-derived compounds, both heterogeneous materials and homogeneous catalysts based on Pd7–9, Pt10–12, Ru13–15, Rh16 and Ni17–29 have been developed which allow for reductive C–O cleavage reactions that produce alcohols or alkene bio-building blocks (Fig. 1) Apart from this general approach, we believe it is highly desirable to develop alternative strategies based on selective arene hydrogenation to effectively utilize lignin-derived compounds and other oxygenated (hetero)arenes as feedstock for both bulk and fine chemical production. The resulting optimal catalyst allows for unique hydrogenation of all kinds of substituted arenes including lignin-derived aromatic compounds to give the aliphatic congeners in both high activity and selectivity
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