Abstract
We have successfully incorporated iron species into mesoporous aluminosilicates (Al-SBA-15) using a simple mechanochemical milling method. The catalysts were characterized by nitrogen physisorption, inductively coupled plasma mass spectrometry (ICP-MS), pyridine (PY) and 2,6-dimethylpyridine (DMPY) pulse chromatography titration, powder X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and scanning electron microscopy with energy-dispersive X-ray spectroscopy (SEM-EDX). The catalysts were tested in the N-alkylation reaction of aniline with benzyl alcohol for imine production. According to the results, the iron sources, acidity of catalyst and reaction conditions were important factors influencing the reaction. The catalyst showed excellent catalytic performance, achieving 97% of aniline conversion and 96% of imine selectivity under optimized conditions.
Highlights
N-alkylation of amines is an important reaction in organic chemistry for the synthesis ofN-containing compounds, basic intermediates used in dyestuff synthesis, herbicides, synthetic rubbers, pharmaceuticals and insecticides [1,2,3,4]
The catalysts were characterized by using various techniques including nitrogen physisorption, inductive coupling plasma mass spectrometry (ICP-MS), pyridine (PY) and 2,6-dimethyl pyridine (DMPY) pulse chromatography titration, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and scanning electron microscope-energy dispersive X-ray spectroscopy (SEM-EDX)
According to the international union of pure and applied chemistry (IUPAC), the nitrogen adsorption/desorption isotherms of all samples were of type IV with H1 type hysteresis loop between 0.5 and 0.8 P/P0 (Figure 1), characteristic of mesoporous materials [22,25]
Summary
N-containing compounds, basic intermediates used in dyestuff synthesis, herbicides, synthetic rubbers, pharmaceuticals and insecticides [1,2,3,4]. Among these nitrogen compounds, secondary amine or imine are of high interest. N-alkylation of amines with alcohols emerged as a more sustainable protocol [5], with alcohols having a low toxicity and being inexpensive by-products generated during the reaction being only water. Homogeneous catalysts of metal complexes (i.e., Ru, Ir, Rh, Pt, Au, Ni, Cu, and Fe) have been used in amine alkylation with alcohols [6,7,8,9,10]. Homogeneous catalysts present a complicated separation of the reaction medium, making it difficult to isolate them from the obtained products
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