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Selective N-Alkylation of Amines with DMC over Biogenic Cu-Zr Bimetallic Nanoparticles.

ABSTRACT: Herein, we report the green synthesis of copper-zirconium bimetallic nanoparticles (Cu-Zr BNPs) from aqueous solutions using Azadirachta indica leaf extract as a reducing and stabilizing agent. The CuO, ZrO₂ NP, and Cu-Zr BNP samples were characterized by X-ray diffraction and Fourier transform infrared (FTIR) spectroscopy, and the morphologies of the samples were analyzed by high-resolution transmission electron microscopy (HR-TEM) with selected area electron diffraction analysis (SAED). The synthesized Cu-Zr BNPs have been employed as efficient catalysts for the selective N-methylation of aromatic and aliphatic amines with dimethyl carbonate. The effect of process conditions on the percentage conversion of benzylamine with dimethyl carbonate as a model reaction has been investigated. The Cu-Zr bimetallic nanoparticle catalytic system in a 1:2 molar ratio was able to convert amines into the corresponding N-methylated amines with a selectivity up to 91% at 180 °C in 4 h. The analysis of catalytic reusability confirmed that the reported heterogeneous catalyst can be used for five consecutive cycles without much loss in activity. Thus, the current protocol can be considered as a simpler, reproducible, and environmentally benign approach for N-methylation of amines.

SUBMITTER: Sharma A

PROVIDER: S-EPMC8210448 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Heterogeneous Zr-Mont catalyst prepared by a simple protocol was employed for the production of diesel fuel precursors via Friedel-Crafts (FC) alkylation of petroleum-derived arenes (e.g., mesitylene, xylene, and toluene) with biomass-derived 5-(hydroxymethyl)furfural (HMF), HMF derivatives, and carbohydrates. Initially, several acidic catalysts were screened for the FC alkylation of mesitylene with HMF in nitroethane solvent. Among all, Zr-Mont catalyst gave an exceptionally high yield (80%) of mesitylmethylfurfural (MMF). The catalytic activity of Zr-Mont was also evaluated for the alkylation of different petroleum-derived arenes with ester/halogen derivatives of HMF. Suitable acid strength and high surface area of Zr-Mont were its major attributes to make it the most efficient solid acid catalyst for this FC reaction. Even after several reuses, the catalytic activity of Zr-Mont was found to be consistent, which was also evidenced by the acidity measurements of fresh and reused Zr-Mont catalysts by temperature-programmed desorption of ammonia and pyridine Fourier transform infrared spectroscopy techniques. Direct conversion of glucose to diesel fuel precursors was also attempted over Zr-Mont catalyst in mesitylene and polar nonacidic solvents at 150 °C. However, the activity of Zr-Mont catalyst was limited for glucose dehydration to HMF and MMF did not form. When the same experiment was performed in formic acid medium, MMF was produced in 34% yield. After the addition of formic acid, the reaction becomes biphasic which contains mesitylene as an organic phase and formic acid as an aqueous phase. Formic acid worked as a solvent, reactant, and cocatalyst, whereas mesitylene worked as a reactant and product extraction phase to enable easy product isolation. With this strategy, other diesel fuel precursors were also produced in 26-30% yields from glucose and different arenes. Similar strategy was successfully extended for the conversion of sucrose to diesel fuel precursors.

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Selective N-Alkylation of Amines with DMC over Biogenic Cu-Zr Bimetallic Nanoparticles.

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