Preparation, Characterization and First Application of Alumina Supported Polyphosphoric Acid (PPA/Al2O3) as a Reusable Catalyst for the Synthesis of 14-Aryl-14H-dibenzo[a, j]xanthenes
Abstract:Alumina supported polyphosphoric acid (PPA/Al 2 O 3 ) was successfully prepared by impregnation of alumina support by polyphosphoric acid and characterized using FT-IR spectroscopy, the N 2 adsorption/desorption analysis (BET), thermal analysis (TG/DTG), and X-ray diffraction (XRD) techniques. The catalytic behavior of this new solid acid supported heterogeneous catalyst was checked in the synthesis of 14-aryl-14H-dibenzo[a, j]xanthenes by cyclocondensation reaction of β-naphthol and aryl aldehydes under solve… Show more
“…In most of these cases, the supported catalysts so prepared could provide advantages over their unsupported counterparts in terms of separation, reusability, and particularly, the ability to provide practical conveniences in a continuous system that is valued in industry. [5][6][7] In supported catalysts, the catalytic behavior of the catalyst is strongly dependent on support properties. Among the various supported catalysts, particularly, alumina and silica supported reagents have advantages of low cost, ease of preparation, and catalyst recycling.…”
A new heterogeneous acidic catalyst was successfully prepared by impregnation of silica (Aerosil 300) by an acidic ionic liquid, named 1-(4-sulfonic acid)butylpyridinium hydrogen sulfate [PYC 4 SO 3 H][HSO 4 ], and characterized using FT-IR spectroscopy, the N 2 adsorption/desorption analysis (BET), thermal analysis (TG/ DTG), and X-ray diffraction (XRD) techniques. The amount of loaded acidic ionic liquid on Aerosil 300 support was determined by acid-base titration. This new solid acidic supported heterogeneous catalyst exhibits excellent activity in the synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation reaction of 2-aminobenzamide with aromatic aldehydes under solvent-free conditions and the desired products were obtained in very short reaction times with high yields. This catalyst has the advantages of an easy catalyst separation from the reaction medium and lower problems of corrosion. Recycling of the catalyst and avoidance of using harmful organic solvent are other advantages of this simple procedure.
“…In most of these cases, the supported catalysts so prepared could provide advantages over their unsupported counterparts in terms of separation, reusability, and particularly, the ability to provide practical conveniences in a continuous system that is valued in industry. [5][6][7] In supported catalysts, the catalytic behavior of the catalyst is strongly dependent on support properties. Among the various supported catalysts, particularly, alumina and silica supported reagents have advantages of low cost, ease of preparation, and catalyst recycling.…”
A new heterogeneous acidic catalyst was successfully prepared by impregnation of silica (Aerosil 300) by an acidic ionic liquid, named 1-(4-sulfonic acid)butylpyridinium hydrogen sulfate [PYC 4 SO 3 H][HSO 4 ], and characterized using FT-IR spectroscopy, the N 2 adsorption/desorption analysis (BET), thermal analysis (TG/ DTG), and X-ray diffraction (XRD) techniques. The amount of loaded acidic ionic liquid on Aerosil 300 support was determined by acid-base titration. This new solid acidic supported heterogeneous catalyst exhibits excellent activity in the synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation reaction of 2-aminobenzamide with aromatic aldehydes under solvent-free conditions and the desired products were obtained in very short reaction times with high yields. This catalyst has the advantages of an easy catalyst separation from the reaction medium and lower problems of corrosion. Recycling of the catalyst and avoidance of using harmful organic solvent are other advantages of this simple procedure.
“…As shown, the compound 3d was obtained in moderate yields in H 2 O, CH 3 CN, AcOEt, and EtOH (entries [16][17][18][19], but in high-yield in CH 2 Cl 2 (entry 20) and also in solvent-free conditions (entry 13). Although, there is no significant difference between solvent-free conditions and CH 2 Cl 2 as solvent in the model reaction, based on our investigations, in CH 2 Cl 2 as solvent, the catalyst has poor reusability, but in solvent-free condition, the reusability of [Et 3 NC 4 SO 3 H][HSO 4 ]/Al 2 O 3 was found to be favorable and it could be recovered and subsequently reused several times.…”
Section: G Of [Et 3 Nc 4 So 3 H][hso 4 ]/Al O 3 (Entry 13mentioning
confidence: 99%
“…For showing the effect of solvent, the same model reaction was also carried out in different solvents including H 2 O, CH 3 CN, AcOEt, EtOH, and CH 2 Cl 2 in the presence of 0.2 g of the catalyst ( Table 2, entries [16][17][18][19][20]. As shown, the compound 3d was obtained in moderate yields in H 2 O, CH 3 CN, AcOEt, and EtOH (entries [16][17][18][19], but in high-yield in CH 2 Cl 2 (entry 20) and also in solvent-free conditions (entry 13).…”
Section: G Of [Et 3 Nc 4 So 3 H][hso 4 ]/Al O 3 (Entry 13mentioning
confidence: 99%
“…Among the various supported catalysts, particularly, alumina and silica supported reagents have advantages of low cost, ease of preparation, and catalyst recycling. [15][16][17][18] Xanthenes have received great attention because of their wide range of therapeutic and biological properties, such as antibacterial, [19] antiviral, [20] and anti-inflammatory activities. [21] Apart from their use as valuable synthetic precursors for many organic compounds [22] and dyes [23] they also found uses in laser technologies, [24] and fluorescent materials for visualization of biomolecules.…”
Preparation of a novel heterogeneous acidic catalyst by impregnation of alumina support by N-(4-sulfonic acid)butyl triethylammonium hydrogen sulfate ([Et 3 NC 4 SO 3 H][HSO 4 ]), an acidic ionic liquid, and its primary application as a solid acidic supported catalyst in the synthesis of 1,8-dioxo-octahydroxanthenes by reaction of dimedone with aromatic aldehydes are described. Characterization of the catalyst was performed by FT-IR, BET, TG/DTG, and XRD techniques. The results showed that the catalyst has high activity and the desired products were obtained in high yields. Moreover, the recovered catalyst was found to be reusable and a considerable catalytic activity still could be achieved after third run.
A polymer support immobilized acidic ionic liquid was prepared by copolymerization of 3-vinyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate with styrene in the presence of benzoyl peroxide and its primary application as a solid acidic heterogeneous catalyst to the synthesis of Hantzsch 1,4-dihydropyridines through a one-pot three-component reaction of aromatic aldehydes, ethyl acetoacetate and ammonium acetate was investigated. The results showed that this heterogeneous catalyst has high catalytic activity and the desired products were obtained in good to high yields. Moreover, the catalyst was found to be reusable and a considerable catalytic activity still could be achieved after third run.
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