4.5 Article

Synthesis of the acid-base bifunctional hybrid catalyst via covalently anchored organomoieties on to the SBA-15: a recyclable catalyst for the one-pot preparation of 1-amidoalkyl-2-naphthols

Journal

RESEARCH ON CHEMICAL INTERMEDIATES
Volume 48, Issue 10, Pages 4033-4047

Publisher

SPRINGER
DOI: 10.1007/s11164-022-04802-w

Keywords

SBA-amino-amido-carboxylic acid; SBA-NH-NHCO-COOH; 1-Amidoalkyl-2-Naphthols compounds; Heterogeneous catalyst; Computational study

Funding

  1. Abadan branch of Islamic Azad University

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In this research, a new catalyst SBA-NH-NHCO-COOH is synthesized and classified through various characterization techniques. The catalytic activity of the nanocomposite is successfully demonstrated in the synthesis of 1-amidoalkyl-2-naphthols. Furthermore, the chemical shift values, X-ray spectra, and structural characteristics of the compound are studied in depth and compared with computed values.
In this research, SBA-amino-amido-carboxylic acid (SBA-NH-NHCO-COOH) is synthesized by nucleophilic substitution of SBA propylchloride (SBA-Cl) with ethylene diamine and then maleic anhydride. To classify the acid-base composite, the infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), differential thermal analysis (DTA), and Brunauer-Emmett-Teller (BET) measurements are used. The one-pot synthesis of 1-amidoalkyl-2-naphthols using three-component couplings of beta-naphthol, aromatic aldehydes, and acetamide with a 0.05 g of catalyst in ethanol under reflux condition, successfully demonstrated the nanocomposite's catalytic activity. Furthermore, H-1 and C-13 chemical shift values, X-ray spectra, and the structural characteristics of 1-amidoalkyl-2-naphthols compounds have also been studied in depth. The experimental data are compared with the values derived from DFT measurements, which included chemical shifts and structural parameters. The calculated H-1 and C-13 chemical shifts, as well as X-ray spectra, agree well with those obtained experimentally. Based on obtained results, it can be concluded that this new catalyst has many benefits, including high yields (85-91%), high catalytic activity, short reaction time, simple technique, and quick set-up.

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