Efficient Synthesis of Water-Soluble Alkyl-bis(<i>m</i>-sulfonated-phenyl)- and Dialkyl-(<i>m</i>-sulfonated-phenyl)-phosphines and Their Evaluation in Rhodium-Catalyzed Hydrogenation of Maleic Acid in Water

Mika, László T.; Orha, László; Farkas, Norbert; Horváth, István T.

doi:10.1021/om800570r

Cited by 20 publications

(16 citation statements)

References 26 publications

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“…In order to approach the activity of the trialkylphosphine modified system, the influence of the electron-donating watersoluble alkyl-bis(m-sulfonated-phenyl)-(L1, L2), dialkyl-(msulfonatedphenyl)phosphines (L5, L6), 36 and TPPTS on the hydrogenation of LA was investigated under 100 bar H 2 (Table 2, entries 1-5). It was clearly demonstrated that the catalytic activity could be considerably enhanced by the incorporation of one or two alkyl functional group(s) into the phosphorus ligands.…”

Section: Hydrogenation Of Levulinic Acid To γ-Valerolactonementioning

confidence: 99%

“…To better understand the influence of the electronic and steric properties of the ligands on the hydrogenation, a series of sulfonated phosphines were tested for GVL production under 10 bar of H 2 and 140 °C (Table 2, entries 6-15). According to published methods 36 the novel sulfonated L3, L4, L7, L8, L9, and L10 have been prepared and characterized (Table 1). Although, the alkyl substituent increases the electron density of the phosphorus ligands, the comparison of the activity of mono-and dialkyl phosphine modified systems revealed higher activity of monoalkyl species for each pair.…”

Section: Hydrogenation Of Levulinic Acid To γ-Valerolactonementioning

confidence: 99%

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Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion

et al. 2012

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γ-Valerolactone (GVL) has been proposed as a sustainable liquid, and could be used for the production of hydrocarbons by using both homogeneous and heterogeneous catalytic systems. The selective reduction of levulinic acid (LA) to GVL is a key transformation for biorefinery concepts based on platform molecules. We report a detailed investigation of the conversion of LA to GVL using molecular hydrogen in the presence of a catalyst in situ generated from Ru(acac) 3 , and electronically and sterically characterized alkyl-bis(m-sulfonated-phenyl)-and dialkyl-(m-sulfonated-phenyl)phosphine (R n P(C 6 H 4 -m-SO 3 Na) 3−n (n = 1 or 2; R = Me, Pr, iPr, Bu, Cp) ligands. The hydrogenation experiments were performed in the range of 5-100 bar H 2 at 140 °C using 0.016 mol% catalyst and 5-20 eqv. of ligand. The effects of hydrogen pressure and Ru/ligand ratio on the LA conversion were determined. The nBuP(C 6 H 4 -m-SO 3 Na) 2 (χ = 12.5, θ Tol = 153°) showed the highest activity achieving turnover numbers up to 6200 with a yield and selectivity higher than 99% in a solvent, chlorine and promoter free reaction mixture. The catalyst was successfully recycled for six consecutive runs without loss of activity. The characterization of sulfonated and non-sulfonated phosphines indicated that the sulfonation had no significant effect on the steric and electronic properties of the ligands.Scheme 1 † Electronic supplementary information (ESI) available. See

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Section: Hydrogenation Of Levulinic Acid To γ-Valerolactonementioning

confidence: 99%

Section: Hydrogenation Of Levulinic Acid To γ-Valerolactonementioning

confidence: 99%

Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion

et al. 2012

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“…TPPTS ((3,3 0 ,3 00 -phosphanetriyltris(benzenesulfonic acid) trisodium salt), P(C 6 H 4 -m-SO 3 Na) 3 ) 35 and BuP(C 6 H 4 -m-SO 3 Na) 2 (Bu-DPPDS) 36 ligands were prepared by published methods.…”

Section: Methodsmentioning

confidence: 99%

Ruthenium-catalyzed solvent-free conversion of furfural to furfuryl alcohol

et al. 2017

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Bidentate phosphine-modified Ru-based homogeneous catalyst systems were developed for solvent-free conversion of furfural to furfuryl alcohol as a versatile biomass-based C 5 -platform molecule. The effect of the ligand structure and ligand concentration, the operating pressure and the reaction temperature on the catalyst's activity were studied in details. Under optimized conditions complete conversion of furfural to furfuryl alcohol was achieved in the absence of any added solvent and without any by-product formation. The maximum turnover frequency (6273 h À1 ) and 100% atom economy were obtained by using homogeneous Ru/Ph 2 P(CH 2 ) 4 PPh 2 catalyst, which was recyclable for twelve consecutive runs without affecting the catalytic performance of the catalyst.

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“…2) with different stereoelectronic properties have been used to evaluate their catalytic properties in the aqueous biphasic hydrogenation of aromatic hydrocarbons. Ligands 1-3 were synthesized according to the literature procedures [39][40][41][42]. In order to rationalize their catalytic behavior we characterized their stereoelectronic nature.…”

Section: Characterization Of the Phosphine Ligandsmentioning

confidence: 99%

“…Solvents were purified, dried and deoxygenated by standard methods . Sulfonated phosphines 1a-b, 2a-b, 2d and 3a-c were synthesized according to the literature procedures [39][40][41][42]. All other starting materials were purchased from Aldrich.…”

Section: General Experimental Detailsmentioning

confidence: 99%

Sulfonated Phosphine Ligands in the Ruthenium Catalyzed Biphasic Hydrogenation of Unsaturated Hydrocarbons

2020

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The hydrogenation of monocyclic aromatic hydrocarbons by ruthenium catalysts has been investigated in the presence of sulfonated monophosphine ligands with different stereoelectronic properties under biphasic conditions. The effects of (i) the number of sulfonate groups, (ii) the steric demand of the ligand and (iii) the σ-donor ability of the phosphorus atom have been investigated in the catalytic reactions. The TEM analysis of the catalytically active systems revealed that in situ formed soluble ruthenium nanoparticles (RuNPs) are responsible for the catalytic turnover. The Ru/sulfonated phosphine system with the properly tuned ligand exhibited high activity (8800 h −1) and selectivity in the hydrogenation of benzene to cyclohexane. Furthermore, the aqueous phase containing RuNPs could be recycled four times without a considerable loss of activity.

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Efficient Synthesis of Water-Soluble Alkyl-bis(m-sulfonated-phenyl)- and Dialkyl-(m-sulfonated-phenyl)-phosphines and Their Evaluation in Rhodium-Catalyzed Hydrogenation of Maleic Acid in Water

Cited by 20 publications

References 26 publications

Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion

Efficient catalytic hydrogenation of levulinic acid: a key step in biomass conversion

Ruthenium-catalyzed solvent-free conversion of furfural to furfuryl alcohol

Sulfonated Phosphine Ligands in the Ruthenium Catalyzed Biphasic Hydrogenation of Unsaturated Hydrocarbons

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