Rhodium-catalyzed hydrogenation of olefins in γ-valerolactone-based ionic liquids

Abstract

γ-Valerolactone-based ionic liquids were successfully used as the catalyst phase for [Rh(cod) 2 ][BF 4 ]/RP(C 6 H 4 -m-SO 3 Na) 2 (R = Me, Pr, Bu, Cp) catalyzed hydrogenation of different olefins. Compared to broadly used ionic liquids e.g. 1-butyl-3-methylimidazolium chloride [bmim][Cl], the turnover frequencies were significantly higher and the reaction was selective for the CvC double bonds in the presence of carbonyl, cyano, and phenyl groups. The catalyst was recycled for ten consecutive runs under regular or biphasic conditions without loss of activity. The vapour pressure and viscosity of γ-valerolactone-based ionic liquids were determined as well. † Electronic supplementary information (ESI) available. See

Hydrogenation of levulinic acid to γ-valerolactone over anatase-supported Ru catalysts: Effect of catalyst synthesis protocols on activity

“…δ-Aminolevulinic acid is a well-known herbicide and β-acetylacrylic acid has been proposed as a (co-)monomer for novel acrylate polymers [1]. Arguably, most attention has been devoted to the conversion of LA to γ-valerolactone (GVL), as GVL is considered as an important platform chemical in its own right and can be used as food additive, solvent and as precursor for fuel additives and bulk polymers [9][10][11][12][13]. The conventional way to produce GVL involves the hydrogenation of LA or its esters [14][15][16], with molecular hydrogen or an alternative hydrogen donor (e.g.…”

Catalytic transfer hydrogenation in γ-valerolactone-based ionic liquids

“…11 Hydrogenation reaction as one of the most important and widely studied transition metal catalyzed homogeneous transformation 12 was also performed in ionic liquids. 13, 14 The 35 catalytic transfer hydrogenation of organic substrates is a safer and more energy-efficient alternative operation without using hydrogen gas and can generally be performed in common organic solvents. 15 Although, the ionic liquids are widely used as environmental benign solvents in high-pressure catalysis, there 40 are only a few examples for application in transfer hydrogenation reactions.…”

“…The combination of the mild conditions of transfer hydrogenation with the advantages of γ-valerolactone(GVL)based ILs could result in an environmentally friendly method for the reduction of organic substrates. In addition, due to the low 45 vapour pressure of GVL based ILs, 14 the risk of environmental emission, therefore the potential hazard to health, could be significantly lower compared to conventional organic solvents.…”

“…23 The reaction rate could be affected by varying the substituents of 70 the valerate-based anion and the tetraalkylammonium-based cation. 14 ). Since the temperature dependence of the vapour pressure of solvents is a key property, it was 85 determined for novel ILs in the temperature range of 0-85 °C.…”

The role of water in catalytic biomass-based technologies to produce chemicals and fuels

“…It can be used for the production of transportation fuels, butane isomers [109], octane booster [108], alkanes [100], 2-methyl-tetrahydrofuran [100], pentane-1,4-diol [100,110], ionic liquids [111,112], adipic acid [113], alkyl valerates [111], polymers [114], pentanoic acid [115] or utilized as a solvent [116,117] (Scheme 5).…”