Anionic Amphiphilic Cyclodextrins Bearing Oleic Grafts for the Stabilization of Ruthenium Nanoparticles Efficient in Aqueous Catalytic Hydrogenation

Abstract

Oleic succinyl β‐cyclodextrin was proved to be efficient for the stabilization of ruthenium nanoparticles (NPs) in aqueous medium. These NPs were characterized by FTIR spectroscopy and transition electron microscopy (TEM). The catalytic activity of these NPs was evaluated in the aqueous hydrogenation of petrosourced and biosourced unsaturated compounds such as benzene and furfural derivatives. The catalytic system can be easily recycled and reused up to nine runs without any loss of activity and selectivity, demonstrating its robustness.

Water-Soluble Noble Metal Nanoparticle Catalysts Capped with Small Organic Molecules for Organic Transformations in Water

“…In a recent report, oleic succinyl-β-cyclodextrin-stabilized RuNPs (Ru_OS-β-CD) was applied for aqueous hydrogenation of olefins. 91 The well-dispersed particles were found to have a narrow size distribution with an average diameter of 2.6 nm. The zeta potential of Ru_OS-β-CD NPs was calculated to be −40 mV, indicating its good stability in the aqueous colloidal suspension.…”

“…Ru(NO)(NO 3 ) 3 could also be reduced by NaBH 4 in the presence of cyclodextrin (7) resulting in the formation of strongly active Ru nanoparticles for the hydrogenation of aromatics, olefins, and carbonyl compounds. 91 NaBH 4 reduction protocol was also utilized for the synthesis of other metal nanoparticles such as Ir and Pd nanoparticles. IrCl 3 was reduced by NaBH 4 with ultrasonication irradiation in the presence of hydroxyl-functionalized tetraalkyl ammonium chloride (8).…”

Energy Densification of Biomass-Derived Furfurals to Furanic Biofuels by Catalytic Hydrogenation and Hydrodeoxygenation Reactions

“…By tuning the surface microstructure, the nitrate and carbonate anion displayed high selectivity toward FAL (97%) and THFAL (99%), respectively [99]. An improvement in the catalytic activity of ruthenium NPsfor FUR hydrogenation was observed using oleic succinyl β-cyclodextrin as the stabilizer [100]. Low conversion of FUR to THFAL was observed in the presence of Pd/SiO 2 .…”

Synthetic Application of Cyclodextrins in Combination with Metal Ions, Complexes, and Metal Particles

“…Of these products, 15-βCD with a substitution degree of 1.6 was used to stabilize ruthenium nanoparticles (2.56 � 0.60 nm) by reducing Ru(NO)(NO 3 ) 3 and 15-βCD (1 : 3 ratio) with NaBH 4 and applying the resulting catalyst in hydrogenations. [42] Hydrogenation of alkenes, aromatics, carbonyl compounds, and unsaturated alcohols took place smoothly requiring a wide range of time intervals (Table 7). The exception is methyl oleate, which proved to be unreactive (entry 9).…”

“…These amphiphilic preparations are highly water‐soluble and have low surface tension and low critical‐aggregation concentration. Of these products, 15 ‐βCD with a substitution degree of 1.6 was used to stabilize ruthenium nanoparticles (2.56±0.60 nm) by reducing Ru(NO)(NO 3 ) 3 and 15 ‐βCD (1 : 3 ratio) with NaBH 4 and applying the resulting catalyst in hydrogenations [42] . Hydrogenation of alkenes, aromatics, carbonyl compounds, and unsaturated alcohols took place smoothly requiring a wide range of time intervals (Table 7).…”