Dicationic Acidic Ionic Liquid Research Articles

Preparation and Identification of a Novel Dicationic Acidic Ionic Liquid Deployed on Cross-Linked Chitosan and its Application in the Promotion of the Synthesis of 1,2,4-Triazolo[5,1-b]quinazolinones and 1,2,4-Triazolo[1,5-a]pyrimidines

Preparation and Identification of a Novel Dicationic Acidic Ionic Liquid Deployed on Cross-Linked Chitosan and its Application in the Promotion of the Synthesis of 1,2,4-Triazolo[5,1-b]quinazolinones and 1,2,4-Triazolo[1,5-a]pyrimidines

Poly Ethylene Glycol Based Dicationic Acidic Ionic Liquid [PEG-DAIL][Cl] Used as Cost Effective and Recyclable Catalyst for Biginelli Reactions

Poly Ethylene Glycol Based Dicationic Acidic Ionic Liquid [PEG-DAIL][Cl] Used as Cost Effective and Recyclable Catalyst for Biginelli Reactions

Synthesis of Symmetric Ethers Using Monocationic and Dicationic Acidic Ionic Liquids

A series of monocationic and dicationic -SO3H functionalized Brønsted acidic ionic liquids (BAILs) are synthesized using different amines int.al., N,N,N′,N′-tetramethylethylenediamine, 1-methylimidazole, pyridine and alkylating agents 1,3-propane- and 1,4-butanesultones. The Hammett acidity (H0) and thermal properties by TG-DSC techniques are investigated. These ionic liquids have been applied to catalyze the dehydration reaction of aliphatic long chain alcohols (1-heptanol, 1-octanol, 1-decanol) at 195 °C. The optimization of reaction conditions and use of dicationic ionic liquids allow to reach rather high yields of symmetric diheptyl ether and dioctyl ether. The reusability of ionic liquids is evaluated using monocationic [PyPS][HSO4], dicationic [TMEDAPS][HSO4] ionic liquids and 1-heptanol.

Kinetics Study of the Transesterification Reaction of Methyl Acetate with Isooctyl Alcohol Catalyzed by Dicationic Heteropolyanion-Based Ionic Liquids

In this work, dicationic acidic heteropolyanion-based ionic liquids were synthesized, and used in transesterification reaction of methyl acetate with isooctyl alcohol for producing isooctyl acetate. Compared with H2SO4, and H3PW12O40, [Bis-BsImB][HPW12O40] and [Bis-Bs-DABCO][HPW12O40] shown excellent catalytic performance. The reaction kinetics and chemical equilibrium of the transesterification catalyzed by [Bis-BsImB][HPW12O40] and [Bis-Bs-DABCO][HPW12O40] were investigated. The effects of reaction temperature, initial reactant molar ratio, and catalyst concentration on the kinetics were studied in detail. The kinetic data were successfully correlated by a pseudohomogeneous model in the temperature range of 328.15 − 343.15 K. The simulation values obtained by the kinetic model were in good agreement with the experimental data. Moreover, [Bis-BsImB][HPW12O40] and [Bis-Bs-DABCO][HPW12O40] could be easily recovered and reused five times without any obvious decrease in catalytic activity.

PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes

An efficient procedure has been researched for the solvent-free synthesis of bis(indolyl)methanes via a one-pot reaction of indoles and aldehydes or ketones promoted by PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL). The catalyst PEG1000-DAIL could be reused seven times with excellent results. Furthermore, through this method, a highly chemoselective reaction of benzaldehyde and acetophenone with indole could be achieved.

Macroalgal biomass hydrolysis using dicationic acidic ionic liquids

AbstractBACKGROUNDMacroalgae has high potential as a bio‐fuel feedstock due to its high carbohydrate content. Conventional aqueous systems require a huge amount of energy to catalyze depolymerization and hydrolysis of macroalgae. Recently various task‐specific ionic liquids (ILs) successfully depolymerized different biomasses, but were thermally unstable. A variety of dicationic acidic ILs (DAILs) connected by oligo‐ethylene glycol (EG) chains bearing hydrogen sulfate (HSO4−) anions were synthesized with better thermal stability and utilized in hydrolysis of macroalgal biomass, Gelidium amansii.RESULTSThe structures of DAILs were confirmed by 1H and 13C NMR as well as FT‐IR. EG‐linker chain lengths and dicationic structure increased the thermal stability of DAILs and influenced their catalytic performance for G. amansii hydrolysis. DAILs linked with short oligo‐EG chains afforded higher sugar yields and exhibited faster hydrolysis rates compared with those linked by long oligo‐EG chains (i.e. PEG400 and PEG600). A maximum sugar yield of 67.45 wt% was recovered from G. amansii using [Tri‐EG‐(MIm)2] 2HSO4 DAIL, after 3 min at 120 °C.CONCLUSIONThe synthesized DAILs showed dual properties as catalyst and reaction medium for hydrolysis of macroalgae in solvent‐less conditions. Shorter oligo‐EG chain linked DAILs exhibited faster reaction rates with higher sugar yields. © 2016 Society of Chemical Industry

ChemInform Abstract: Convenient and Efficient Method for Synthesis of 2,4,6‐Triarylpyridines Using Catalytic Amount of PEG1000‐Based Dicationic Acidic Ionic Liquid under Solvent‐Free Conditions.

AbstractTitle compounds are conveniently and efficiently synthesized by the reaction of chalcones (I) and ammonium acetate or via one‐pot three‐component condensation of aromatic aldehydes with acetophenones (IV) and ammonium acetate.

Efficient method for the synthesis of 3-arylbenzoquinoline, pyranoquinoline, and thiopyranoquinoline derivatives using PEG1000-based dicationic acidic ionic liquid as recyclable catalyst via a one-pot multicomponent reaction

ABSTRACTA series of 3-arylbenzoquinoline, pyranoquinoline, and thiopyranoquinoline derivatives have been synthesized by one-pot, multicomponent reaction of aromatic aldehyde, naphthalen-2-amine, and ketone using polyethylene glycol (PEG1000)–based dicationic acidic ionic liquid as recyclable catalyst with high yields. The PEG ionic liquid and toluene have the advantages of both homogeneous and heterogeneous phases at different temperatures (biphasic conditions at lower temperatures and monophasic at higher temperatures) with the ease of product as well as catalyst separation. Recycling studies have shown that the ionic liquid can be readily recovered and reused several times without significant loss of activity.

Task specific dicationic acidic ionic liquids catalyzed efficient and rapid synthesis of benzoxanthenones derivatives

A rapid and straightforward approach to the synthesis of dibenzo[a,j]xanthenes and 1,8-dioxo-octahydroxanthenes using task specific dicationic acidic ionic liquids as a highly efficient and readily available catalyst under solvent-free condition have been developed. A series of Brønsted–Lewis acidic ionic liquid were prepared and investigated their catalytic activity for synthesis of various xanthenes derivatives from aldehydes and 2-naphthol or dimedone. The ease of the product separation without organic solvent and column chromatography and reusability of acidic ionic liquid catalyst makes this method economically affordable for large-scale synthesis.

Convenient and efficient method for synthesis of 2,4,6-triarylpyridines using catalytic amount of PEG1000-based dicationic acidic ionic liquid under solvent-free conditions

ABSTRACTA convenient and efficient method for synthesis of substituted 2,4,6-triarylpyridines by the reaction of chalcones and ammonium acetate or via one-pot, three-component condensation of aromatic aldehydes with acetophenones and ammonium acetate has been developed by using the efficient catalyst PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL) under solvent-free conditions. Recycling studies have shown that the PEG1000-DAIL can be readily recovered and reused several times without significant loss of activity.

PEG1000-Based Dicationic Acidic Ionic Liquid Catalyzed One-Pot Synthesis of 4-Aryl-3-Methyl-1-Phenyl-1H-Benzo[h]pyrazolo [3,4-b]quinoline-5,10-Diones via Multicomponent Reactions

A novel and green approach for efficient and rapid synthesis of 4-aryl-3-methyl-1-phenyl-1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-diones has been accomplished by the one-pot condensation reaction of aromatic aldehydes, 3-methyl-1-phenyl-1H-pyrazol-5-amine and 2-hydroxynaphthalene-1,4-dione using PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL) as a catalyst was reported. Recycling studies have shown that the PEG1000-DAIL can be readily recovered and reused several times without significant loss of activity. The key advantages are the short reaction time, high yields, simple workup, and recovered catalyst.

ChemInform Abstract: Manganese Dioxide and N,N′,N′′‐Trihydroxyisocyanuric Acid: A Novel and Recyclable Catalytic System for Aerobic Oxidation of Toluene Derivatives in PEG‐1000‐Based Dicationic Acidic Ionic Liquid.

N,N′,N″-trihydroxyisocyanuric acid (THICA) with MnO2 promotes the aerobic oxidation of toluene derivatives to corresponding acids in PEG-1000-based dicationic acidic ionic liquid (PEG1000–DAIL). It is demonstrated that THICA/MnO2 is very active and selective and several toluene derivatives are efficiently oxidized to corresponding acids under mild conditions. Both the catalyst and PEG1000–DAIL can be reused after simple separation. A plausible mechanism is also proposed based on the experimental observations. Copyright © 2015 John Wiley & Sons, Ltd.

ChemInform Abstract: PEG1000‐Based Dicationic Acidic Ionic Liquid Catalyzed One‐Pot Synthesis of 1,4‐Dihydropyridines via the Hantzsch Reaction.

AbstractThe catalyst can be reused nine times with excellent results.

Manganese dioxide and N,N′,N″‐trihydroxyisocyanuric acid: a novel and recyclable catalytic system for aerobic oxidation of toluene derivatives in PEG‐1000‐based dicationic acidic ionic liquid

N,N′,N″‐trihydroxyisocyanuric acid (THICA) with MnO2 promotes the aerobic oxidation of toluene derivatives to corresponding acids in PEG‐1000‐based dicationic acidic ionic liquid (PEG1000–DAIL). It is demonstrated that THICA/MnO2 is very active and selective and several toluene derivatives are efficiently oxidized to corresponding acids under mild conditions. Both the catalyst and PEG1000–DAIL can be reused after simple separation. A plausible mechanism is also proposed based on the experimental observations. Copyright © 2015 John Wiley & Sons, Ltd.

Polyethylene Glycol-400-Functionalized Dicationic Acidic Ionic Liquids for Highly Efficient Conversion of Fructose into 5-Hydroxymethylfurfural

A variety of polyethylene glycol-400-functionalized dicationic acidic ionic liquids (ILs) (PEG400-DAILs) were synthesized and tested in the dehydration of fructose. Among these catalysts, hydrogen sulfate anion-based ILs showed the higher catalytic performance in the conversion of fructose. The highest HMF yield of 96.5 % with 100 % consumption of fructose were obtained after 60 min at 110 °C. The effects of catalyst concentration, reaction time, reaction temperature, and solvents were systematically investigated. In addition, the generality of the catalysts was examined by processing inulin and sucrose to HMF with yield of 71.9 and 52.1 % under certain conditions, respectively. PEG400-DAILs possess modified physicochemical properties such as low viscosity, strong hydrophilicity and hydrogen bonding with sugars so as to improve activity for the dehydration of fructose into HMF. The used IL catalyst could be separated and recycled repeatedly without significant loss of catalytic activity. The research emphasizes preparation of the novel catalysts combining polymers with functionalized ILs for conversion of renewable biomass.

ChemInform Abstract: PEG1000‐Based Dicationic Acidic Ionic Liquid as an Efficient Catalyst for Mannich‐Type Reaction in Water.

AbstractThe reaction is performed in water, and the catalyst can be reused in six runs with only a slight loss of activity.

PEG1000-Based Dicationic Acidic Ionic Liquid Catalyzed One-pot Synthesis of 1,4-Dihydropyridines via the Hantzsch Reaction

Devising reactions that achieve multiple-bond formation in one operation has become one of the major challenges in the search for efficient syntheses. Multi-component reactions (MCRs) allow the cre...

PEG1000-Based Dicationic Acidic Ionic Liquid as an Efficient Catalyst for Mannich-Type Reaction in Water

PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL) was found to be an efficient and recyclable catalyst for Mannich-type reaction of different ketones with various aromatic aldehydes and aromatic amines in water to give various β-arylamino ketones in good yields. The catalytic system could be easily recovered and reused for at least six runs only with slight decrease in its activity.

Facile protection of carbonyl compounds as oxathiolanes and thioacetals promoted by PEG1000-based dicationic acidic ionic liquid as chemoselective and recyclable catalyst

Efficient oxathioacetalization and thioacetalization of carbonyl compounds have been achieved in high yields employing PEG1000-based dicationic acidic ionic liquid as a catalyst. The PEG ionic liquid and toluene have the advantages of both homogeneous and heterogeneous phases at different temperatures (biphasic conditions at lower temperatures and monophasic at higher temperatures) with the ease of product as well as catalyst separation. Recycling studies have shown that the ionic liquid can be readily recovered and reused several times without significant loss of activity. In addition, by using this catalyst, high chemoselective protection of carbonyl compounds has been achieved.

A facile and efficient protocol for esterification and acetalization in a PEG1000-D(A)IL/toluene thermoregulated catalyst–media combined systems

A novel efficient and recyclable temperature-dependent biphasic catalyst and reaction media combined system comprised of PEG-1000 linked dicationic acidic ionic liquid and toluene was developed and applied in esterification of aromatic acids and acetalization of aromatic aldehydes with good to excellent yields. This system is characteristic of temperature-dependent reversible biphasic property, simple and facile recyclability, high catalytic activity and extensive substrate and reaction adaptability.