Selective Catalysis for Room-Temperature Hydrogenation of Biomass-Derived Compounds over Supported NiPd Catalysts in Water

Abstract

Utilizing biomass-derived furan-based platform chemicals for the production of a wide range of value-added components for application as fuels/fuel blenders and other fine chemicals is gaining much attention. Here, we demonstrated an efficient room-temperature selective hydrogenation of furan-based long chain aldol compounds over supported NiPd/SiO2, NiPd/RHA (RHA is rice-husk ash), and NiPd/Z4A (Z4A is zeolite 4A) catalysts in water. A wide range of furan-based compounds, such as 1,5-bis­(furan-2-yl)­penta-1,4-dien-3-one (1), 4-(furan-2-yl)­but-3-en-2-one (3), 1,3-bis­(furan-2-yl)­prop-2-en-1-one (4), 1-(furan-2-yl)-3-(5-methylfuran-2-yl)­prop-2-en-1-one (5), and 3-(furan-2-ylmethylene)­pentane-2,4-dione (6), were conveniently hydrogenated to the corresponding saturated ketone products using the present protocol. Our findings inferred that the studied supported NiPd catalysts selectively promoted the hydrogenation of the CC bond over the CO bond to yield the corresponding saturated ketone products. The observed tuned catalytic properties can be attributed to the crucial role of the support in controlling the substrate-to-surface interactions, presumably, by disfavoring the interaction of polar carbonyl functional groups with the catalyst surface and, hence, facilitating the hydrogenation of CC over CO bonds. Moreover, the support RHA facilitated the high dispersion of NiPd nanoparticles (∼4 nm) for the NiPd/RHA catalyst. Hence, the NiPd/RHA catalyst displayed high stability under the catalytic reaction conditions and was reused for six consecutive catalytic runs without any significant loss in the catalytic activity.

Selectivity control in hydrogenation through adaptive catalysis using ruthenium nanoparticles on a CO2-responsive support

“…Catalytic study. The hydrogenation of furfural acetone (1) has been the subject of various studies towards the production of fuel components or chemicals from biomass 3,39,40 . The reaction process starts with C=C bond hydrogenation to form 4-(2-furyl) butan-2-one (2).…”

Ruthenium on Alkali‐Exfoliated Ti3(Al0.8Sn0.2)C2 MAX Phase Catalyses Reduction of 4‐Nitroaniline with Ammonia Borane

“…Hydrogenation of 4‐nitroaniline using boranes generally follow either a tandem reduction pathway, [65–70] or a transfer hydrogenation pathway [62,71–73] . A tandem hydrogenation first produces hydrogen, which is then used as reductant in an ensuing reaction [38,66,74] . Transfer hydrogenation starts with B−H bond cleavage, to give an [M]−H active species.…”

Production of jet fuel cycloalkanes from 5‐(hydroxymethyl)furfural via cascade catalysis on Mg(Al)(Zr)O supported CuCo

“…But with the presence of strong acidic sites, undesirable C–C bond breakage also occurred. The catalyst systems consisting of only metal components as active centers, such as Cu/MgAl 2 O 4 23 and NiPd/RHA (RHA is rice husk ash), 38 have also been developed for the defunctionalization of furanic aldol adducts. These catalysts, without solid acid supports, prove effective in the removal of exocyclic oxygen and the hydrogenation of C=C bonds, but deficient in the removal of cyclic‐oxygen in furan‐ring or tetrahydrofuran‐ring.…”