Metal–Organic Framework MIL-101-NH2‑Supported Acetate-Based Butylimidazolium Ionic Liquid as a Highly Efficient Heterogeneous Catalyst for the Synthesis of 3‑Aryl-2-oxazolidinones

A novel heterogeneous catalyst, the ionic liquid (IL) of 1-butyl-3-methylimidazolium acetate (BmimOAc) immobilized on MIL-101-NH2, denoted as IL­(OAc–)-MIL-101-NH2, was prepared by the “ship-in-a-bottle” strategy. The IL of BmimOAc was prepared in the MIL-101-NH2 nanocages primordially, in which the...

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Veröffentlicht in:Langmuir 2019-01, Vol.35 (2), p.495-503
Hauptverfasser: Chong, S. Y, Wang, T. T, Cheng, L. C, Lv, H. Y, Ji, M
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel heterogeneous catalyst, the ionic liquid (IL) of 1-butyl-3-methylimidazolium acetate (BmimOAc) immobilized on MIL-101-NH2, denoted as IL­(OAc–)-MIL-101-NH2, was prepared by the “ship-in-a-bottle” strategy. The IL of BmimOAc was prepared in the MIL-101-NH2 nanocages primordially, in which the condensation product of MIL-101-NH2’s amine group with 1,1′-carbonyldiimidazole (CDI) reacted with 1-bromo butane, and then the intermediate exchanged with potassium acetate. The structure and physicochemical properties of IL­(OAc–)-MIL-101-NH2 were characterized by powder X-ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, DRS UV–vis, nitrogen adsorption–desorption, and elemental analysis. The results indicated that BmimOAc was anchored in the MIL-101-NH2 skeleton via the acylamino group and confined in the nanocages in the form of a single molecule. The composite material of IL­(OAc–)-MIL-101-NH2 exhibited excellent catalytic activity and catalytically synthesized 3-aryl-2-oxazolone in an excellent yield of 92%. It can be reused up to six times without noteworthy loss of its activity and demonstrated distinct size-selective property for substrates. It was conjectured that the diffusion kinetics of reactants could be controlled by the aperture size of the metal–organic framework support.
ISSN:0743-7463
1520-5827
DOI:10.1021/acs.langmuir.8b03153