Acid Imidazolium Hydrogen Sulfate Research Articles

Ionic liquid based electroless silver plating bath for Printable circuit boards (PCBs) finishing

Immersion silver-plating technique is typically used for uniform coating on printed circuit boards (PCB) for finishing. Herein, we report an unconventional protocol for preparation of non-toxic immersion silver-plating solution/bath. The solution was prepared through electrolysis using ionic liquid (1, 3-disulfonic acid imidazolium hydrogen sulfate [Dsim] [HSO4]) as electrolyte, metallic silver (Ag) as anode and copper as cathode. As a result of electrolysis, IL-capped aqueous charged silver ion (Ag+) solution [colloidal Ag-IL adduct solution] is obtained. Presence of Ag+ in solution was verified by cyclic voltammetry (CV) experiments. Chemical reduction of Ag+ with Hydrazine Hydrate (NH2-NH2·H2O) yielded AgNPs. The AgNPs analyzed through dynamic light scattering (DLS) exhibiting 269.99 ± 14.2 nm size with Polydispersity Index (PDI) 0.126. The metallic copper strip immersed into the solution and a shiny silver plated surface obtained within 1–5 min at room temperature. Film thickness can be controlled by varying time of immersion. The corrosion rate was found to be 0.0012 mm/a by Tafel fitting. The solution is stable for the months without losing efficiency whereas the recovered IL used five times without significant loss in efficiency.

Selective monoalkylation of hydroquinone in the presence of SO3H-functionalized ionic liquids as catalysts

A process aiming at O-alkylation of hydroquinone (HQ), where ionic liquids (ILs) act as catalyst is objectively described. Five SO3H-functionalized ILs having different cations were prepared and characterized by NMR and FTIR techniques. The acidity and thermal stability of ILs were determined by Hammett function and thermogravimetric analysis (TGA), respectively. The catalytic activity of these ILs were tested for O-alkylation of HQ with methanol in 4-methoxyphenol (4MP) in the presence of small amount of benzoquinone (BQ). The effect of reaction parameters such as temperature, time, catalyst loading and substrate concentration on the conversion of HQ and product distribution was examined and optimized to maximize the yield of 4MP using 1,3-disulfonic acid imidazolium hydrogen sulfate (IL2) catalyst. Maximum yield of desired product 4MP 93.79% was obtained at 338 K temperature, 5.45 × 10–2 mol HQ, 8.33 × 10–3 mol BQ, and 10.37 mol% catalyst loading in 120 min reaction time. Single-product formation was observed up to 338 K temperature but higher temperature (above 338 K) and longer reaction time resulted in the formation of 2,4-dimethoxyphenol (24DMP) as a by-product. Catalyst recyclability was also established up to the fifth run which showed no declination in its activity.

Study on Sulfonic Acid Functional Group Modified Imidazole Ionic Liquids for Oxygen Concentration Detection

The ionic liquid is a kind of ionic salt capable of being liquid state at room temperature. As a new type of green organic solvent, ionic liquid has the advantages of good electrical conductivity, wide electrochemical window, very low vapor pressure, and is widely used in electrochemical, organic synthesis and other fields. The use of ionic liquids as electrolytes in electrochemical oxygen sensors can alter the shortcomings of the current sensor's inability to operate at high temperature and humidity conditions. Besides, ionic liquids with certain catalytic functional group could improve the response performance of sensing devices. Therefore, in this paper, ionic liquids based on imidazolium, 1-methyl-3-propanesulfonic acid imidazolium hydrogensulfate ([Psmim]HSO4) and 1-methyl-3-butpropanesulfonic acid imidazolium hydrogensulfate ([Bsmim]HSO4 )with sulfonic-acid catalytic functional group were studied. Both ionic liquids mentioned above were synthesized through a traditional two-step method. Electrochemical tests including linear scanning voltammetry (LSV) and electrochemical impedance spectroscopy (EIS) of both ionic liquids were carried out with an electrochemical workstation to characterize the intrinsic electrochemical performance of both ionic liquids. On the other hand, cyclic voltammetry (CV) curves were tested, which shows a proportional linear relationship between oxygen reduction peak current and the oxygen concentrations from 0% to 100% O2 with the corresponding R2 (R2 >0.97), and chronoamperometric current tsests were also carried out to futher confirm the ionic liquids promising materials for oxygen sensing. (This paper is funded by the International Exchange Program of Harbin Engineering University for Innovation-oriented Talents Cultivation.)

Synthesis of Tetrahydrotriazoloacridines: A Synergistic Effect of Microwave Irradiation and Brönsted Acidic Ionic Liquids

3‐Methyl‐1‐sulfonic acid imidazolium hydrogen sulfate ([MSIm][HSO4]) catalyzed the condensation of 5‐aminobenzotriazole and 5,5‐dimethyl‐cyclohexane‐1,3‐dione (dimedone) with aromatic aldehydes under microwave irradiation. This method is efficient to synthesize 11‐aryl‐8,8‐dimethyl‐6,7,9,11‐tetrahydro[1,2,3]triazolo[4,5‐a]acridine‐10(1H)‐one derivatives as a series of tetrahydroacridines in good to excellent yields, while the catalyst can be recovered and reused up to six times without significant loss of activity. This one‐pot three‐component reaction provided an efficient method for the synthesis of aromatic heterocycles.

ChemInform Abstract: 1,3‐Disulfonic Acid Imidazolium Hydrogen Sulfate: A Reusable and Efficient Ionic Liquid for the One‐Pot Multi‐Component Synthesis of Pyrimido[4,5‐b]quinoline Derivatives.

A green, simple and convenient method for the synthesis of pyrimido[4,5-b]quinoline derivatives has been developed through a three-component one-pot condensation of 6-amino-1,3-dimethyluracil, aldehydes, and cyclic 1,3-diketones in the presence of 1,3-disulfonic acid imidazolium hydrogen sulfate [dsim]HSO4 as an efficient catalyst. The present methodology offers several advantages such as excellent yields, simple procedure, short reaction times, high yields of the products and easy work-up procedures. Also, the catalyst was readily recovered and could be reused several times without a noticeably decrease in its activity.

1, 3-Disulfonic acid imidazolium hydrogen sulphate as an efficient and reusable ionic liquid for the multicomponent synthesis of polyhydroquinoline derivatives under solvent-free conditions

A facile and highly effective one-pot synthesis of polyhydroquinoline derivatives is reported via Hantzsch condensation of aldehydes, 1,3-dicarbonyl compounds, ethyl acetoacetate, and ammonium acetate in the presence of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient and recyclable ionic liquid under solvent-free conditions. This methodology offers several advantages such as short reaction times, high yields, environmentally benign, mild reaction conditions, simple work-up procedure, and reusability of the ionic liquid.

1,3-Disulfonic acid imidazolium hydrogen sulfate: a reusable and efficient ionic liquid for the one-pot multi-component synthesis of pyrimido[4,5-b]quinoline derivatives

1,3-Disulfonic acid imidazolium hydrogen sulfate (DSIMHS) has been used for the simple and efficient synthesis of pyrimido[4,5-b]quinoline derivatives. The procedure gave the products in excellent yields in very short reaction times.

1,2-Dimethyl-N-butanesulfonic acid imidazolium hydrogen sulfate as efficient ionic liquid catalyst in the synthesis of indeno fused pyrido[2,3-d]pyrimidines

Indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidin-4,6-(5H,11H)dione derivatives were synthesized regioselectively in high yields by a three-component reaction of 1,3-indanedione, aromatic aldehydes and 2,6-diaminopyrimidin-4(3H)-one in the presence of 1,2-dimethyl-N-butanesulfonic acid imidazolium hydrogen sulfate ([DMBSI]HSO4) ionic liquid as green and reusable catalyst. This protocol produced the desired products in high yields (87–95%) and short reaction times (3–6min).

Synthesis of benzo[g]indeno[2,1-b]quinoline derivatives via four-component and one-pot synthesis in presence of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate

A simple and facile synthesis of 12-arylbenzo[g]indeno[2,1-b]quinoline-6,11,13-trione derivatives was accomplished by the one-pot condensation of 2-hydroxynaphthalene-1,4-dione, aryl aldehydes, 2H-indene-1,3-dione, and ammonium acetate under solvent-free conditions in the presence of a Brönsted ionic liquid catalyst, namely 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate.

Four-component one-pot synthesis of unsymmetrical polyhydroquinoline derivatives using 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as a catalyst

3-Methyl-1-sulfonic acid imidazolium hydrogen sulfate has been used as an efficient, halogen-free, and reusable Brönsted acidic ionic liquid catalyst for the synthesis of ethyl-4-aryl/heteryl-hexahydro-trimehtyl-5-oxoquinoline-3-carboxylates via the one-pot condensation of dimedone with aryl/heteryl aldehydes, ethyl acetoacetate, and ammonium acetate under solvent-free conditions. This method has the advantage of being clean and simple, as well as providing the desired product in high yield over a short reaction time. Furthermore, the catalyst could be recycled and reused four times without any discernible reduction in activity.

ChemInform Abstract: One‐Pot Synthesis of Various Xanthene Derivatives Using Ionic Liquid 1,3‐Disulfonic Acid Imidazolium Hydrogen Sulfate as an Efficient and Reusable Catalyst under Solvent‐Free Conditions.

Abstract In this study, 1,3-disulfonic acid imidazolium hydrogen sulfate (DSIMHS) is used as an efficient and reusable ionic liquid for the green, mild, and efficient synthesis of xanthenes under solvent-free conditions. Simple and easy work-up, low cost, green process, short reaction times and excellent yields of the products are the advantages of this procedure. Further, the catalyst can be recycled and reused at least for four times without a noticeably decrease in its catalytic activity.

A solvent-free synthesis of coumarins using 1,3-disulfonic acid imidazolium hydrogen sulfate as a reusable and effective ionic liquid catalyst

1,3-Disulfonic acid imidazolium hydrogen sulfate has been used as an effective and reusable ionic liquid catalyst for the synthesis of coumarins from phenol derivatives with β-ketoesters via the Von Pechmann condensation under solvent-free conditions. This method consistently has the advantages of excellent yields, easy and quick isolation of the products, short reaction times, and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be recovered and reused for four times without loss of activity.

3-Methyl-1-sulfonic acid imidazolium hydrogen sulfate-catalyzed three-component, one-pot synthesis of 13-aryl-12H-benzo[f]indeno[1,2-b]quinoline-12-one derivatives

3-Methyl-1-sulfonic acid imidazolium hydrogen sulfate, an efficient, halogen-free, and reusable Bronsted ionic liquid, catalyzed the synthesis of 13-aryl-12H-benzo[f]indeno[1,2-b]quinoline-12-one derivatives by one-pot condensation of 2-naphthylamine, aromatic aldehydes, and 2H-indene-1,3-dione under solvent-free conditions. This method has the advantages of high yields, clean reaction, simplicity, and short reaction time. The catalyst can be recycled and reused four times without significant loss of activity.

Solvent-free synthesis of quinoline derivatives via the Friedländer reaction using 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient and recyclable ionic liquid catalyst

Abstract A convenient, highly versatile and eco-friendly protocol for the synthesis of quinoline derivatives via the Friedlander reaction is presented. The method is based on the use of 1,3-disulfonic acid imidazolium hydrogen sulfate (DSIMHS) as an efficient and reusable ionic liquid catalyst. A variety of ketones afforded the substituted quinolines in excellent yields during relatively short reaction times under solvent-free conditions; the catalyst could be easily recovered and reused for several times without any appreciable loss of activity.

Biodiesel from Citrullus colocynthis oil: sulfonic-ionic liquid-catalyzed esterification of a two-step process.

Biodiesel was prepared from Citrullus colocynthis oil (CCO) via a two-step process. The first esterification step was explored in two ionic liquids (ILs) with 1,3-disulfonic acid imidazolium hydrogen sulfate (DSIMHSO4) and 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate (MSIMHSO4). Both ILs appeared to be good candidates to replace hazardous acidic catalyst due to their exceptional properties. However, the two sulfonic chains existing in DSIMHSO4 were found to increase the acidity to the IL than the single sulfonic chain in MSIMHSO4. Based on the results, 3.6 wt% of DSIMHSO4, methanol/CCO molar ratio of 12 : 1, and 150°C offered a final FFA conversion of 95.4% within 105 min. A 98.2% was produced via second KOH-catalyzed step in 1.0%, 6 : 1 molar ratio, 600 rpm, and 60°C for 50 min. This new two-step catalyzed process could solve the corrosion and environmental problems associated with the current acidic catalysts.

One-pot synthesis of various xanthene derivatives using ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable catalyst under solvent-free conditions

Abstract In this study, 1,3-disulfonic acid imidazolium hydrogen sulfate (DSIMHS) is used as an efficient and reusable ionic liquid for the green, mild, and efficient synthesis of xanthenes under solvent-free conditions. Simple and easy work-up, low cost, green process, short reaction times and excellent yields of the products are the advantages of this procedure. Further, the catalyst can be recycled and reused at least for four times without a noticeably decrease in its catalytic activity.

ChemInform Abstract: Ionic Liquid 1,3‐Disulfonic Acid Imidazolium Hydrogen Sulfate: A Novel and Highly Efficient Catalyst for the Preparation of 1‐Carbamatoalkyl‐2‐naphthols and 1‐Amidoalkyl‐2‐naphthols.

AbstractThe title compounds (16 examples) are prepared in short reaction times (≤ 35 min) and without a solvent by the multicomponent reaction of β‐naphthol, benzaldehydes, and either carbamates or amides.

Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines

In this work, novel Brønsted acidic ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate {[Dsim]HSO4} is synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR, mass, TG, DTG and XRD spectra. This ionic liquid, with three acidic functional groups, is utilized as a highly efficient, homogeneous and reusable catalyst for the preparation of hexahydroquinolines via one-pot multi-component condensation of arylaldehydes, dimedone (5,5-dimethylcyclohexane-1,3-dione), β-ketoesters and ammonium acetate under solvent-free conditions. The catalyst can form dual hydrogen-bond using its SO3H groups which this subject can direct to its assembly and efficiency.

ChemInform Abstract: Synthesis of Coumarins via Pechmann Reaction Catalyzed by 3‐Methyl‐1‐sulfonic Acid Imidazolium Hydrogen Sulfate as an Efficient, Halogen‐Free and Reusable Acidic Ionic Liquid.

AbstractAcidic ionic liquid [Msim]HSO4 is used as an efficient catalyst for Pechmann condensation reaction.

1,3-Disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable ionic liquid catalyst for the N-Boc protection of amines

1,3-Disulfonic acid imidazolium hydrogen sulfate is easily prepared and used as an efficient and recyclable ionic liquid for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be reused and recovered for several times without loss of activity.