“Water soluble” palladium nanoparticle engineering for C–C coupling, reduction and cyclization catalysis

Ayad, Anas Iben; Marín, C.; Colaço, Elodie; Lefèvre, Christophe; Méthivier, Christophe; Driss, A. Ould; Landoulsi, Jessem; Guénin, Erwann

doi:10.1039/c9gc02546d

Cited by 32 publications

(16 citation statements)

References 90 publications

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“…Nanopure water (18 MΩ cm −1 ), obtained from a Millipore Gradiant Elix-3A10 system (Millipore SAS, Molsheim, France), was used for all experiments. Synthesis and characterization of the Pd NPs as well as their bisphosphonic acid ligand were performed using the protocols described in our previous work [15].…”

Section: Chemicalsmentioning

confidence: 99%

“…Pd NPs have been shown to be excellent catalysts for different reactions performed in aqueous media, such as carbon-carbon cross-coupling, hydrogenation of alkenes, and oxidation of primary alcohols as shown in our previous work [15]. We used benzyl bisphosphonic acid as a ligand for the nanoparticles (see Figure 2).…”

Section: Catalytic Reduction Of 4-nitrophenol Using Pd Npsmentioning

confidence: 99%

“…In this work, we propose to study the catalytic reduction of 4-nitrophenol (4-Nip) to 4-aminophenol (4-Amp) in the presence of Pd NPs and sodium borohydride as a reductant in water and to study the kinetics of the reaction. These Pd NPs are obtained in a simple and eco-friendly manner and have already shown high efficiency for several organic reactions in aqueous media [15]. Therefore, understanding their kinetics in a well-defined model such as 4-Nip reduction is of interest.…”

Section: Introductionmentioning

confidence: 99%

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Kinetic Analysis of 4-Nitrophenol Reduction by “Water-Soluble” Palladium Nanoparticles

et al. 2020

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The most important model catalytic reaction to test the catalytic activity of metal nanoparticles is the reduction of 4-nitrophenol to 4-aminophenol by sodium borohydride as it can be precisely monitored by UV–vis spectroscopy with high accuracy. This work presents the catalytic reduction of 4-nitrophenol (4-Nip) to 4-aminophenol (4-Amp) in the presence of Pd nanoparticles and sodium borohydride as reductants in water. We first evaluate the kinetics using classical pseudo first-order kinetics. We report the effects of different initial 4-Nip and NaBH4 concentrations, reaction temperatures, and mass of Pd nanoparticles used for catalytic reduction. The thermodynamic parameters (activation energy, enthalpy, and entropy) were also determined. Results show that the kinetics are highly dependent on the reactant ratio and that pseudo first-order simplification is not always fit to describe the kinetics of the reaction. Assuming that all steps of this reaction proceed only on the surface of Pd nanoparticles, we applied a Langmuir−Hinshelwood model to describe the kinetics of the reaction. Experimental data of the decay rate of 4-nitrophenol were successfully fitted to the theoretical values obtained from the Langmuir–Hinshelwood model and all thermodynamic parameters, the true rate constant k, as well as the adsorption constants of 4-Nip, and BH4− (K4-Nip and KBH4−) were determined for each temperature.

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Section: Chemicalsmentioning

confidence: 99%

Section: Catalytic Reduction Of 4-nitrophenol Using Pd Npsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Kinetic Analysis of 4-Nitrophenol Reduction by “Water-Soluble” Palladium Nanoparticles

et al. 2020

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“…Metal nanoparticles are widely used in catalyzing organic synthesis and antibacterial materials due to their catalytic activity and bactericidal effect [152,153]. However, they are considered potentially harmful to the environment because of long-term exposure and the difficulty of recycling [154,155].…”

Section: Anti-pollution Applicationsmentioning

confidence: 99%

Lignin Nanoparticles and Their Nanocomposites

2021

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Lignin nanomaterials have emerged as a promising alternative to fossil-based chemicals and products for some potential added-value applications, which benefits from their structural diversity and biodegradability. This review elucidates a perspective in recent research on nanolignins and their nanocomposites. It summarizes the different nanolignin preparation methods, emphasizing anti-solvent precipitation, self-assembly and interfacial crosslinking. Also described are the preparation of various nanocomposites by the chemical modification of nanolignin and compounds with inorganic materials or polymers. Additionally, advances in numerous potential high-value applications, such as use in food packaging, biomedical, chemical engineering and biorefineries, are described.

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“…Metal nanoparticles (NPs) with different composition, morphology, and surface chemistry can be used for applications like NP-mediated catalysis, [1][2][3][4][5][6][7] cancer therapy, [8][9][10][11][12] and chemosensing. [13][14][15][16][17][18] To ensure the solubility of pristine metallic NPs in polar solvents, stabilizing agents like citrate and tetraoctylammonium bromide must be introduced into the mixture.…”

Section: Introductionmentioning

confidence: 99%

Dispersion State Phase Diagram of Citrate-Coated Metallic Nanoparticles in Saline Solutions

Franco-Ulloa

Tatulli²,

Moglianetti³

et al. 2020

Preprint

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The fundamental interactions underlying citrate-mediated chemical stability of metal nanoparticles (NPs), and their surface characteristics dictating particle dispersion/aggregation in aqueous solutions, are largely unclear. Here, we used a newly developed theoretical model to estimate the stoichiometry of citrate molecules chemisorbed onto spherical metallic NPs and define the uncovered solvent-accessible surface area of the NP. Then, we exploited two-body free energy calculations and extended coarse-grained molecular dynamics simulations of citrate-capped metallic NPs in saline solutions to explore an experimentally relevant range of NP charge, as well as the electrolytic medium’s ionic strength, a known trigger for aggregation. In this way, we define dispersion state phase diagrams of citrate-capped metal nanocolloids. UV-vis spectroscopy experiments validated our predictions and extended our results to NPs up to 35 nm. Altogether, our results disclose a complex interplay between the particle size, its surface charge density, and the ionic strength of the medium, which ultimately clarifies how these variables impact colloidal stability. <br>

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“Water soluble” palladium nanoparticle engineering for C–C coupling, reduction and cyclization catalysis

Abstract: Water stable Pd-NPs prepared in an eco-friendly manner enable highly efficient catalysis of 6 organic reactions in aqueous media with quantities of Pd down to the ppm level and high turnover frequencies.

Cited by 32 publications

References 90 publications

Kinetic Analysis of 4-Nitrophenol Reduction by “Water-Soluble” Palladium Nanoparticles

Kinetic Analysis of 4-Nitrophenol Reduction by “Water-Soluble” Palladium Nanoparticles

Lignin Nanoparticles and Their Nanocomposites

Dispersion State Phase Diagram of Citrate-Coated Metallic Nanoparticles in Saline Solutions

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