Kinetics of homogeneous and heterogeneous reactions in the reductive aminolysis of glucose with dimethylamine

Poissonnier, Jeroen; Pelckmans, Michiel; Waes, Frederik Van; Moonen, Kristof; Sels, Bert F.; Thybaut, Joris; Marin, Guy

doi:10.1016/j.apcatb.2018.01.025

Cited by 15 publications

(18 citation statements)

References 52 publications

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“…The adsorption/desorption steps are labeled as 1, −1, 2, −2, 6, −6, 7, and −7; while the surface reaction ones are labeled as 3, −3, 4, −4, 5, and −5. In this microkinetic methodology, apart from the set of ordinary differential equations describing the mass balance of each bulk species (Equation (1)), the pseudo-steady state approximation for the intermediates (Equation (2)), and the mass balance of the active sites (Equation 3) were also taken into account [7]:…”

Section: Methodsmentioning

confidence: 99%

Microkinetic Modeling of the Water-Gas Shift Reaction over Cobalt Catalysts Supported on Multi-Walled Carbon Nanotubes

Cavalcanti

Poissonnier

Vandevyvere

et al. 2020

The 1st International Electronic Conference on Catalysis Sciences

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Section: Methodsmentioning

confidence: 99%

Microkinetic Modeling of the Water-Gas Shift Reaction over Cobalt Catalysts Supported on Multi-Walled Carbon Nanotubes

Cavalcanti

Poissonnier

Vandevyvere

et al. 2020

The 1st International Electronic Conference on Catalysis Sciences

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“…Most of the currently reported catalysts for the preparation of biomass-based organoamines (CN bond formation) via catalytic reductive amination are loaded with noble or transition metal particles via direct impregnation. [31,32] On the one hand, these catalysts require harsh reaction conditions with low product selectivity; on the other hand, the metal particles tend to aggregate into large particles and are severely lost during the reaction. Finding a catalyst that is cheap, low toxic and easy to recover, and can convert LA to pyrrolidone under relatively mild conditions is paramount.…”

Section: Introductionmentioning

confidence: 99%

Synergistic Catalysis of Co‐Zr/CN_x Bimetallic Nanoparticles Enables Reductive Amination of Biobased Levulinic Acid

Fang

2022

Advanced Sustainable Systems

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Bimetallic synergy and carbon–nitrogen doping can contribute to enhanced catalytic activity due to the strong electronic state and unique geometrical structure. In this work, a series of biomass‐derived Co‐M bimetallic CN doped catalysts (Co‐M@Chitosan‐X; M = Zr, Ni, Fe, Cu, In; X denotes the molar percentage of M) are prepared via simple oil bath reflow and annealing. The Co‐Zr@Chitosan‐X catalysts are determined to contain alloys (Co‐Zr), metal‐carbon bonds (Co‐C, Zr‐C), metal‐nitrogen bonds (Co‐N, Zr‐N), and metal oxides (Co3O4, ZrO2) through a series of characterizations, in which graphite‐coated alloys and metal oxides are found to be the catalytically active species. The doping of the second metal results in a significant enhancement for the number of active sites in the catalyst, and the d‐band center is shifted toward a deviation from the Fermi energy level. Among the tested catalysts, Co‐Zr@Chitosan‐20 exhibits superior catalytic activity for the reductive amination of biobased levulinic acid to 5‐methyl‐2‐pyrrolidone in 99.3% selectivity and 92.8% yield. This non‐noble metal bimetallic synergistic catalytic protocol opens an avenue for efficiently producing biomass‐derived nitrogenous chemicals.

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“…Particularly, nitrogen species are contained in over 80% of the top 200 pharmaceuticals 11 . A number of bio-based amines (e.g., aryl-amines, furyl-amines, alkyl-amines, and alkanolamines) have been reported to be efficiently synthesized from small platform molecules via a range of reaction routes like reductive amination of carbonyl compounds 12–16 , reductive aminolysis of simple sugars 17–20 , and hydrogenation-decarbonylation of amino acids 21 . Among these approaches, catalytic reductive amination of carboxides using molecular hydrogen is extensively performed over either transition (Raney Ni) or noble metals (e.g., Ru, Pd) 12,22 .…”

Section: Introductionmentioning

confidence: 99%

N-formyl-stabilizing quasi-catalytic species afford rapid and selective solvent-free amination of biomass-derived feedstocks

Guo

et al. 2019

Nat Commun

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Nitrogen-containing compounds, especially primary amines, are vital building blocks in nature and industry. Herein, a protocol is developed that shows in situ formed N-formyl quasi-catalytic species afford highly selective synthesis of formamides or amines with controllable levels from a variety of aldehyde- and ketone-derived platform chemical substrates under solvent-free conditions. Up to 99% yields of mono-substituted formamides are obtained in 3 min. The C-N bond formation and N-formyl species are prevalent in the cascade reaction sequence. Kinetic and isotope labeling experiments explicitly demonstrate that the C-N bond is activated for subsequent hydrogenation, in which formic acid acts as acid catalyst, hydrogen donor and as N-formyl species source that stabilize amine intermediates elucidated with density functional theory. The protocol provides access to imides from aldehydes, ketones, carboxylic acids, and mixed-substrates, requires no special catalysts, solvents or techniques and provides new avenues for amination chemistry.

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Kinetics of homogeneous and heterogeneous reactions in the reductive aminolysis of glucose with dimethylamine

Cited by 15 publications

References 52 publications

Microkinetic Modeling of the Water-Gas Shift Reaction over Cobalt Catalysts Supported on Multi-Walled Carbon Nanotubes

Microkinetic Modeling of the Water-Gas Shift Reaction over Cobalt Catalysts Supported on Multi-Walled Carbon Nanotubes

Synergistic Catalysis of Co‐Zr/CN_x Bimetallic Nanoparticles Enables Reductive Amination of Biobased Levulinic Acid

N-formyl-stabilizing quasi-catalytic species afford rapid and selective solvent-free amination of biomass-derived feedstocks

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Kinetics of homogeneous and heterogeneous reactions in the reductive aminolysis of glucose with dimethylamine

Cited by 15 publications

References 52 publications

Microkinetic Modeling of the Water-Gas Shift Reaction over Cobalt Catalysts Supported on Multi-Walled Carbon Nanotubes

Microkinetic Modeling of the Water-Gas Shift Reaction over Cobalt Catalysts Supported on Multi-Walled Carbon Nanotubes

Synergistic Catalysis of Co‐Zr/CNx Bimetallic Nanoparticles Enables Reductive Amination of Biobased Levulinic Acid

N-formyl-stabilizing quasi-catalytic species afford rapid and selective solvent-free amination of biomass-derived feedstocks

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Resources

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Synergistic Catalysis of Co‐Zr/CN_x Bimetallic Nanoparticles Enables Reductive Amination of Biobased Levulinic Acid