Reductive Oligomerization of Nitroaniline Catalyzed by Fe 3 O 4 Spheres Decorated with Group 11 Metal Nanoparticles.

Autor: Huerta-Aguilar CA; School of Engineering and Sciences, Tecnologico de Monterrey, 5718 Atlixcáyotl, 72453 Puebla, Mexico., Srivastava R; Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar 140001, Panjab, India., Arenas-Alatorre JA; Instituto de Física, Universidad Nacional Autónoma de México (UNAM), Cd. Universitaria, 04510 México, D. F., México., Thangarasu P; Faculty of Chemistry, National Autonomous University of Mexico (UNAM), 04510 Mexico City, Mexico.
Jazyk: angličtina
Zdroj: ACS omega [ACS Omega] 2023 Feb 13; Vol. 8 (8), pp. 7459-7469. Date of Electronic Publication: 2023 Feb 13 (Print Publication: 2023).
DOI: 10.1021/acsomega.2c06326
Abstrakt: The present work demonstrates a simple and sustainable method for forming azo oligomers from low-value compounds such as nitroaniline. The reductive oligomerization of 4-nitroaniline was achieved via azo bonding using nanometric Fe 3 O 4 spheres doped with metallic nanoparticles (Cu NPs, Ag NPs, and Au NPs), which were characterized by different analytical methods. The magnetic saturation ( M s ) of the samples showed that they are magnetically recoverable from aqueous environments. The effective reduction of nitroaniline followed pseudo-first-order kinetics, reaching a maximum conversion of about 97%. Fe 3 O 4 -Au is the best catalyst, its a reaction rate ( k Fe 3 O 4 -Au = 0.416 mM L -1 min -1 ) is about 20 times higher than that of bare Fe 3 O 4 ( k Fe 3 O 4 = 0.018 mM L -1 min -1 ). The formation of the two main products was determined by high-performance liquid chromatography-mass spectrometry (HPLC-MS), evidencing the effective oligomerization of NA through N = N azo linkage. It is consistent with the total carbon balance and the structural analysis by density functional theory (DFT)-based total energy. The first product, a six-unit azo oligomer, was formed at the beginning of the reaction through a shorter, two-unit molecule. The nitroaniline reduction is controllable and thermodynamically viable, as shown in the computational studies.
Competing Interests: The authors declare no competing financial interest.
(© 2023 The Authors. Published by American Chemical Society.)
Databáze: MEDLINE
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