Synthesis of new low-viscous sulfonic acid-functionalized ionic liquid and its application as a Brönsted liquid acid catalyst for the one-pot mechanosynthesis of 4H-pyrans through the ball milling process

Khaligh, Nader Ghaffari; Mihankhah, Taraneh; Johan, Mohd Rafie

doi:10.1016/j.molliq.2019.01.024

Cited by 46 publications

(7 citation statements)

References 79 publications

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“…Ionic liquids as novel promoter/additive which could be regenerated were employed for the synthesis of imines [77] and in multicomponent synthesis of 4H-pyrans which started with Knoevenagel reaction [78].…”

Section: Synthesismentioning

confidence: 99%

Recent Advances in Mechanochemical Organic Synthesis

Margetić¹,

Štrukil²

2020

Organic Synthesis [Working Title]

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Section: Synthesismentioning

confidence: 99%

Recent Advances in Mechanochemical Organic Synthesis

Margetić¹,

Štrukil²

2020

Organic Synthesis [Working Title]

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“…Ionic liquids (ILs), which are salts in a liquid state at low temperature, continue to attract intense research attention for a diverse range of applications such as energy storage, extraction and separation, , sensing, catalysis, , and lubrication. , This interest is driven by ILs’ mix of physical properties which often include low vapor pressures, high electrical conductivity, thermal stability, nonflammability, nonvolatility, large electrochemical window (ECW), and high thermal and mechanical stability . However, another well-known IL physical property hinders performance for many potential applications: high viscosity.…”

Section: Introductionmentioning

confidence: 99%

Nanostructure of Locally Concentrated Ionic Liquids in the Bulk and at Graphite and Gold Electrodes

Wang,

Buzolic,

Mullen

et al. 2023

ACS Nano

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The physical properties of ionic liquids (ILs) have led to intense research interest, but for many applications, high viscosity is problematic. Mixing the IL with a diluent that lowers viscosity offers a solution if the favorable IL physical properties are not compromised. Here we show that mixing an IL or IL electrolyte (ILE, an IL with dissolved metal ions) with a nonsolvating fluorous diluent produces a low viscosity mixture in which the local ion arrangements, and therefore key physical properties, are retained or enhanced. The locally concentrated ionic liquids (LCILs) examined are 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (HMIM TFSI), 1hexyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate (HMIM FAP), or 1-butyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate (BMIM FAP) mixed with 1,1,2,2-tetrafluoroethyl 2,2,2-trifluoroethyl ether (TFTFE) at 2:1, 1:1, and 1:2 (w/w) IL:TFTFE, as well as the locally concentrated ILEs (LCILEs) formed from 2:1 (w/w) HMIM TFSI−TFTFE with 0.25, 0.5, and 0.75 m lithium bis(trifluoromethylsulfonyl)imide (LiTFSI). Rheology and conductivity measurements reveal that the added TFTFE significantly reduces viscosity and increases ionic conductivity, and cyclic voltammetry (CV) reveals minimal reductions in electrochemical windows on gold and carbon electrodes. This is explained by the small-and wide-angle X-ray scattering (S/WAXS) and atomic force microscopy (AFM) data, which show that the local ion nanostructures are largely retained in LCILs and LCILEs in bulk and at gold and graphite electrodes for all potentials investigated.

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“…[22,23] Recently, chemists have used various catalysts for the elegant synthesis of chromenes due to their unique properties. [24][25][26][27][28][29][30][31][32][33] Reporting the effects of different catalysts such as synthetic copper iodide (CuI), [34] 1,8-diazabicyclo [5.4.0] undec-7ene (DBU), [35] nanoparticles (9Fe 3 O 4 @CÀ SO 3 H), [39] Rochelle salt, [36] iron oxide nanoparticle (Fe 3 O 4 ), [37] tripotassium phosphate (K 3 PO 4 ), [38] dual-organocatalytic (pTsOH.H 2 O & pyrrolidine), [39] ammonium acetate (NH 4 OAc), [40] and sodium citrate [41] in the synthesis of several heterocyclic compounds. Although the developed methods have some advantages, they have several limitations, including low yield, unavailable reagents, effluent pollution, rough reaction conditions, and laborious work-up processes.…”

Section: Introductionmentioning

confidence: 99%

One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

Salmalian,

Mahmoodi,

Sheykhan

2023

ChemistrySelect

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A new method for synthesizing chromene derivatives as an essential class of heterocyclic compounds has been reported. This research described synthesizing and identifying three new organic salt catalysts based on phosphate moieties. Among the synthesized new phosphate‐based organic salt catalysts, disodium ethyl (phenyl) amino phosphate (DSEAP) plays an essential role and reusable catalyst for the preparation of chromene derivatives under different reaction conditions following the principles of green chemistry. Cost‐effectiveness, non‐toxicity and easy availability are among the salient features of this environmentally friendly catalyst. Furthermore, the catalyst was satisfactorily recycled up to four times without significant performance degradation in the yield of synthesized chromenes. X‐ray diffraction (XRD), infrared spectroscopy (FT‐IR), thermal gravimetric analysis (TGA), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) were employed to illustrate the structural and morphologic characteristics of the catalysts. Some synthesized chromene derivatives, including 4I and 4P, showed good antibacterial and biological antioxidant activity compared to the standard drug, respectively. In this research, DSEAP was used as a heterogeneous catalyst in performing one‐pot 3MCRs of aryl aldehyde, an active methylene group e. g. ethyl acetoacetate or diethyl malonate and 5,5‐dimethyl‐1,3‐cyclohexanedione.

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Synthesis of new low-viscous sulfonic acid-functionalized ionic liquid and its application as a Brönsted liquid acid catalyst for the one-pot mechanosynthesis of 4H-pyrans through the ball milling process

Cited by 46 publications

References 79 publications

Recent Advances in Mechanochemical Organic Synthesis

Recent Advances in Mechanochemical Organic Synthesis

Nanostructure of Locally Concentrated Ionic Liquids in the Bulk and at Graphite and Gold Electrodes

One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

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