One-pot amination of cyclohexanone-to-secondary amines over carbon-supported Pd: Unraveling the reaction mechanism and kinetics

Arteaga-Pérez, Luis E.; Manrique, Raydel; Castillo-Puchi, Francisca; Ortega, Maray; Bertiola, Camila; Pérez, Andy J.; Jiménez, Romel

doi:10.1016/j.cej.2021.129236

Cited by 13 publications

(11 citation statements)

References 37 publications

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“…Moreover, the imine is formed regardless of the nature of the support, which is consistent with previous findings. 19,79 The conversion values for Pd/Al 2 O 3 -D3 and Pd/C were 5 times higher than that for Pd/SiO 2 , and the yield of secondary amines increased from 13% for Pd/SiO 2 to 64 and 82% for Pd/C and Pd/Al 2 O 3 -D3, respectively. In addition, different product distributions were observed among these catalysts, which could be related to the promotion or suppression of different reaction steps in the catalytic cycle owing to the density and/or nature of the acidic sites.…”

Section: Resultsmentioning

confidence: 98%

Reductive amination of phenol over Pd-based catalysts: elucidating the role of the support and metal nanoparticle size

et al. 2023

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Section: Resultsmentioning

confidence: 98%

Reductive amination of phenol over Pd-based catalysts: elucidating the role of the support and metal nanoparticle size

et al. 2023

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“…The XRD pattern of Pd/C (Figure c) shows sharp signals centered at 2θ = 39.8, 46.0, 68, 81.8, and 86.4°. According to the COD database and literature, these reflections are respectively ascribed to the (111), (200), (220), (311), and (222) planes in zero-valence palladium (Pd 0 ) while the broad diffraction peak around 2θ = 24° was attributed to the amorphous phase of the carbon support. , Finally, the two weak reflections at 54.6 and 59.7°are attributed to the presence of some oxidized (PdO) phases. These results confirm that the predominant phase in Pd/C is the Pd0, which is known by its activity in phenolic hydrogenation reactions and thus a high activity to lignin deconstruction into phenolic monomers and monoaromatics is expected.…”

Section: Resultsmentioning

confidence: 99%

High Phenol Yields from Catalytic Hydropyrolysis of Lignin and Phenolic-Rich Raffinate

Ghysels,

Arteaga-Pérez,

Léon

et al. 2023

ACS Sustainable Chem. Eng.

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In this work, fast pyrolysis of woody biomass for levoglucosan production was combined with reductive thermocatalytic valorization of its two main side streams, being (i) pyrolytic lignin and (ii) a phenolic-rich raffinate. Pyrolytic lignin is the precipitate, obtained upon cold water precipitation of pyrolysis oil. The phenolic-rich raffinate is the organic phase that originates from subsequent solvent extraction of the former water and levoglucosan-rich stream. This organic raffinate contains watersoluble phenolic monomers and is as such an underexplored (co-)feed for hydropyrolysis. Hydropyrolysis was performed of (i) pyrolytic lignin, (ii) pyrolysis oil-derived phenolics from the organic raffinate, (iii) organosolv lignin as model technical lignin, and a combination of pyrolytic lignin and pyrolysis oil-derived phenolics. The effect of hydrogen pressure (4 and 30 bar) and the presence of a Pd/C catalyst on the product slate and yields were assessed. Without catalytic vapor-phase upgrading, many different low-concentration phenolics were obtained, with a total yield of ca. 10 wt % (for pyrolytic lignin) to 13 wt % (for pyrolysis oilderived phenolics). The product slate positively decomplexified upon catalytic vapor-phase upgrading. The yield in phenolics decreased modestly to 7−10 wt %, mostly being phenol, cresol, and xylenol. Pyrolysis oil-derived phenolics had for these conditions the highest yield in phenolics; its application as co-feed thus always goes in tandem with a yield increase in phenolics. It was also calculated that conversion of all quantified monomers to either phenol or catechol, yielded ca. 5−6 wt % phenol or 5−7 wt % catechol. From pine wood to phenolics, the yield varied between 1.9 (catalytic hydropyrolysis) and 2.3 wt% (non-catalytic). Overall, this work demonstrates value creation from overlooked side streams of the pyrolysis refinery.

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“…Figure shows the parity within the close relationship between the theoretical rate of reaction (calculated from model execution) and the experimentally obtained reaction rate. The parity plot explains that the model can simulate the experiment trend properly, and therefore, model 9, i.e., LHHW 2-site competitive associative adsorption, is accepted as a kinetic model. , …”

Section: Resultsmentioning

confidence: 99%

“…The parity plot explains that the model can simulate the experiment trend properly, and therefore, model 9, i.e., LHHW 2-site competitive associative adsorption, is accepted as a kinetic model. 55,56…”

Section: Kinetic Modelingmentioning

confidence: 99%

Kinetics of Reductive Alkylation of Aniline with Acetone Using a Ni/Organoclay Catalyst

Gajbhiye,

Rathod,

Kantam

2024

Ind. Eng. Chem. Res.

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The kinetic model for reductive alkylation of aniline with acetone using 30 wt % Ni/Organoclay was derived and validated at different temperatures. The catalyst was synthesized and characterized for structural and morphological properties, showcasing promising potential in organic synthesis due to the synergistic effects of nickel on organoclay. As per our knowledge, no one reported the reductive alkylation of aniline using Ni/ Organoclay. Additionally, very few articles are reported on the kinetic modeling of this reaction. To address this gap, we have investigated the kinetics of reductive alkylation of aniline with acetone using a Ni/ Organoclay catalyst. The study systematically investigates the influence of various reaction parameters, such as temperature, pressure, catalyst screening, concentration of the catalyst, mole ratio, agitation speed, and reactant concentrations, on the reaction kinetics. The kinetic analysis involves the determination of crucial parameters, such as reaction rate, activation energies, and heat of adsorption. A number of rate equations were derived to fit the batch reactor data, and rate models based on Langmuir−Hinshelwood competitive associative adsorption of the surface reaction between the Schiff base and hydrogen as the rate-limiting catalytic steps were found to represent the experimental data.

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One-pot amination of cyclohexanone-to-secondary amines over carbon-supported Pd: Unraveling the reaction mechanism and kinetics

Cited by 13 publications

References 37 publications

Reductive amination of phenol over Pd-based catalysts: elucidating the role of the support and metal nanoparticle size

Reductive amination of phenol over Pd-based catalysts: elucidating the role of the support and metal nanoparticle size

High Phenol Yields from Catalytic Hydropyrolysis of Lignin and Phenolic-Rich Raffinate

Kinetics of Reductive Alkylation of Aniline with Acetone Using a Ni/Organoclay Catalyst

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