Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

3-(1-Methyl-3-imidazolio)propane-sulfonate: a precursor to a Bronsted acid ionic liquid.

ABSTRACT: The title compound, C(7)H(12)N(2)O(3)S, is a zwitterion precursor to a Brønsted acid ionic liquid with potential as an acid catalyst. The C-N-C-C torsion angle of 100.05?(8)° allows the positively charged imidazolium head group and the negatively charged sulfonate group to inter-act with neighboring zwitterions, forming a C-H?O hydrogen-bonding network; the shortest among these inter-actions is 2.9512?(9)?Å. The C-H?O inter-actions can be described by graph-set notation as two R(2) (2)(16) and one R(2) (2)(5) hydrogen-bonded rings.

SUBMITTER: Reichert WM

PROVIDER: S-EPMC2983509 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

3-(1-Methyl-3-imidazolio)propane-sulfonate: a precursor to a Brønsted acid ionic liquid.

Reichert W Matthew WM Trulove Paul C PC De Long Hugh C HC

Acta crystallographica. Section E, Structure reports online 20100213 Pt 3

The title compound, C(7)H(12)N(2)O(3)S, is a zwitterion precursor to a Brønsted acid ionic liquid with potential as an acid catalyst. The C-N-C-C torsion angle of 100.05 (8)° allows the positively charged imidazolium head group and the negatively charged sulfonate group to inter-act with neighboring zwitterions, forming a C-H⋯O hydrogen-bonding network; the shortest among these inter-actions is 2.9512 (9) Å. The C-H⋯O inter-actions can be described by graph-set notation as two R(2) (2)(16) and o ...[more]

PMID: 21580354

Similar Datasets

Ultrasonication-Assisted and Benzimidazolium-Based Bronsted Acid Ionic Liquid-Catalyzed Transesterification of Castor Oil.

Project description:In this investigation, we report the synthesis of biodiesel using benzimidazolium-based brønsted acid ionic liquid (BBAIL) catalyst under the influence of ultrasonication. The prepared BBAIL catalyst was characterized by Fourier transform infrared and NMR spectroscopy techniques, and its acidity was determined by the Hammett method with 4-nitroaniline as the indicator. Ultrasonicator horn (22 kHz, 500 W) was used in this work with an on-off cycle of 50-20 s at 70% amplitude. The highest biodiesel yield of 96% was achieved by ultrasonication when 1:10 molar ratio of castor oil to methyl alcohol was used at 50 °C temperature with 9 mol % of the catalyst in just 90 min, which is about 10 times lesser than the process without ultrasonication. At similar conditions, 96% biodiesel yield was obtained in 14 h without ultrasonication. In summary, ultrasonication proved to be an efficient way to improve biodiesel synthesis in less time and BBAIL showed excellent activity toward the conversion of glycerides to synthesize biodiesel. Other important highlights are easy separation of the catalyst and recyclability up to three cycles with small decrease in its activity.

| S-EPMC6643412 | biostudies-literature

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Bronsted acidic ionic liquid.

Project description:Raw material from biomass and green preparation processes are the two key features for the development of green products. As a bio-lubricant in metalworking fluids, estolides of ricinoleic acid are considered as the promising substitute to mineral oil with a favorable viscosity and viscosity index. Thus, an efficient and sustainable synthesis protocol is urgently needed to make the product really green. In this work, an environment-friendly Brønsted acidic ionic liquid (IL) 1-butanesulfonic acid diazabicyclo[5.4.0]undec-7-ene dihydrogen phosphate ([HSO3-BDBU]H2PO4) was developed as the efficient catalyst for the production of oligomeric ricinoleic acid from ricinoleic acid under solvent-free conditions. The reaction parameters containing reaction temperature, vacuum degree, amount of catalyst and reaction time were optimized and it was found that the reaction under the conditions of 190 °C and 50 kPa with 15 wt % of the [HSO3-BDBU]H2PO4 related to ricinoleic acid can afford a qualified product with an acid value of 51 mg KOH/g (which corresponds to the oligomerization degree of 4) after 6 h. Furthermore, the acid value of the product can be adjusted by regulating the reaction time, implying this protocol can serve as a versatile method to prepare the products with different oligomerization degree and different applications. The other merit of this protocol is the facile product separation by stratification and decantation ascribed to the immiscibility of the product and catalyst at room temperature. It is also worth mentioning that the IL catalyst can be used at least for five cycles with high catalytic activity. As a result, the protocol based on the IL catalyst, i.e. [HSO3-BDBU]H2PO4 shows great potential in industrial production of oligomeric ricinoleic acid from ricinoleic acid.

| S-EPMC7082613 | biostudies-literature

Tunable Aryl Imidazolium Recyclable Ionic Liquid with Dual Bronsted-Lewis Acid as Green Catalyst for Friedel-Crafts Acylation and Thioesterification.

Project description:Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.

| S-EPMC7024267 | biostudies-literature

Synthesis and Characterization of a Novel Hydroquinone Sulfonate-Based Redox Active Ionic Liquid.

Project description:Introducing redox-active moieties into an ionic liquid (IL) structure is an exciting and attractive approach that has received increasing interest over recent years for a various range of energy applications. The so-called redox-active ionic liquids (RAILs) provide a highly versatile platform to potentially create multifunctional electroactive materials. Ionic liquids are molten salts consisting of ionic species, often having a melting point lower than 100 °C. Such liquids are obtained by combining a bulky asymmetric organic cation and a small anion. Here, we report on the synthesis of a novel RAIL, namely 1-butyl-3-methylimidazolium hydroquinone sulfonate ((BMIM)(HQS)). (BMIM)(HQS) was synthesized in a two-step procedure, starting by the quaternization of methylimidazole using butylchloride to produce 1-butyl-3-methylimidazolium chloride ((BMIM)(Cl)), and followed by the anion exchange reaction, where the chloride anion is exchanged with hydroquinone sulfonate. The resulting product was characterized by 1H NMR, 13C NMR, FT-IR spectroscopy, themogravimetric analysis, and differential scanning calorimetry, and shows a high stability up to 340 °C. Its electrochemical behavior was investigated using cyclic voltammetry at different temperatures and its viscosity analysis was also performed at variable temperatures. The electrochemical response of the presented RAIL was found to be temperature dependent and diffusion controlled. Overall, our results demonstrated that (BMIM)(mix of HQS and HSQ) is redox active and possesses high stability and low volatility, leading to the employment of this RAIL without any additional supporting electrolyte or additives.

| S-EPMC8231554 | biostudies-literature

3-(2-Methyl-1,3-benzo-thia-zol-3-ium-3-yl)propane-1-sulfonate monohydrate.

Project description:In the title hydrated zwitterion, C11H13NO3S2·H2O, the N-C-C-C and C-C-C-S torsion angles in the side-chain are 171.06?(14) and 173.73?(12)°, respectively. In the crystal, inversion-related mol-ecules are ?-stacked with an inter-planar separation of 3.3847?(2)?Å. O-H?O hydrogen bonds link inversion-related mol-ecules with a pair of water mol-ecules to form R 4 (2)(8) rings. The closest S?S contact is 3.4051?(15)?Å between inversion-related mol-ecules.

| S-EPMC4051035 | biostudies-literature

Two-stage conversion of high free fatty acid Jatropha curcas oil to biodiesel using Bronsted acidic ionic liquid and KOH as catalysts.

Project description:Biodiesel was produced from high free fatty acid (FFA) Jatropha curcas oil (JCO) by two-stage process in which esterification was performed by Brønsted acidic ionic liquid 1-(1-butylsulfonic)-3-methylimidazolium chloride ([BSMIM]Cl) followed by KOH catalyzed transesterification. Maximum FFA conversion of 93.9% was achieved and it reduced from 8.15 wt% to 0.49 wt% under the optimum reaction conditions of methanol oil molar ratio 12 : 1 and 10 wt% of ionic liquid catalyst at 70 °C in 6 h. The ionic liquid catalyst was reusable up to four times of consecutive runs under the optimum reaction conditions. At the second stage, the esterified JCO was transesterified by using 1.3 wt% KOH and methanol oil molar ratio of 6 : 1 in 20 min at 64 °C. The yield of the final biodiesel was found to be 98.6% as analyzed by NMR spectroscopy. Chemical composition of the final biodiesel was also determined by GC-MS analysis.

| S-EPMC3988968 | biostudies-literature

Geminal Bronsted acid ionic liquids as catalysts for the Mannich reaction in water.

Project description:Quaternary ammonium geminal Brønsted acid ionic liquids (GBAILs) based on zwitterionic 1,2-bis[N-methyl-N-(3-sulfopropyl)-alkylammonium]ethane (where the carbon number of the alkyl chain is 4, 8, 10, 12, 14, 16, or 18) and p-toluenesulfonic acid monohydrate were synthesized. The catalytic ionic liquids were applied in three-component Mannich reactions with an aldehyde, ketone, and amine at 25 °C in water. The effects of the type and amount of catalyst and reaction time as well as the scope of the reaction were investigated. Results showed that GBAIL-C14 has excellent catalytic activity and fair reusability. The catalytic procedure was simple, and the catalyst could be recycled seven times via a simple separation process without noticeable decreases in catalytic activity.

| S-EPMC4057752 | biostudies-literature

Catalytic preparation of levulinic acid from cellobiose via Bronsted-Lewis acidic ionic liquids functional catalysts.

Project description:Brønsted-Lewis acidic ionic liquids (ILs) were applied to catalyze cellobiose to prepare levulinic acid (LA) in one pot under hydrothermal conditions. Under the optimum conditions, the highest LA yield of 67.51% was obtained when low [HO3S-(CH2)3-mim]Cl-FeCl3 (molar fraction of FeCl3 x?=?0.60) was used. This indicated the Brønsted-Lewis acidic ILs played an active role in the conversion of cellobiose to LA. The catalytic mechanism of ILs had been established, disclosing that the Brønsted-Lewis acidic ILs had the catalytic synergistic effect originating from its double acid sites. During the reaction process, the Lewis acid sites improved the isomerization of glucose to fructose, then the Brønsted and Lewis acid sites simultaneously enhanced the dehydration of fructose to produce hydroxymethylfurfural (HMF), which was propitious to the synthesize LA with high yield. In addition, LA could be easily extracted by methyl isobutyl ketone (MIBK), and the ILs could retain its basic activity after 5 cycles. The solid residues were characterized using SEM, FT-IR and TG-DTG spectroscopy. It was the conclusion that a large amount of humins were produced during the cellobiose conversion process. In this reaction, the ILs not only overcomes the problems of the conventional catalyst, but also completes the reaction-separation integration and the recycling of the catalyst. This paper provided an important theoretical basis for the application of ILs in the field of biomass.

| S-EPMC6372595 | biostudies-literature

Green Bronsted acid ionic liquids as novel corrosion inhibitors for carbon steel in acidic medium.

Project description:New ionic liquids with multiple Brönsted acid sites were synthesized in ?98% yield, and their inhibiting properties for the corrosion of carbon steel in 0.5?M HCl solution had been evaluated using electrochemical impedance spectroscopy, potentiodynamic polarization and weight loss method, finally the possible inhibiting mechanism was proposed according to UV-visible spectroscopic measurements and surface analysis including SEM and XPS techniques. The designed cation structure of Brönsted acid ionic liquids (BAILs), with one phenyl and two imidazolium rings, makes them good mixed-type inhibitors via the adsorption of BAILs on the steel surface to suppress both anodic and cathodic processes, obeying Langmuir adsorption isotherm. As potential acid catalysts, BAILs show nice corrosion inhibiting performance in acidic medium regardless of their Brönsted acidity, which is of great significance to enlarge the industry applications of BAILs.

| S-EPMC5562793 | biostudies-literature

Alendronic Acid as Ionic Liquid: New Perspective on Osteosarcoma.

Project description:Herein the quantitative synthesis of eight new mono- and dianionic Organic Salts and Ionic Liquids (OSILs) from alendronic acid (ALN) is reported by following two distinct sustainable and straightforward methodologies, according to the type of cation. The prepared ALN-OSILs were characterized by spectroscopic techniques and their solubility in water and biological fluids was determined. An evaluation of the toxicity towards human healthy cells and also human breast, lung and bone (osteosarcoma) cell lines was performed. Globally, it was observed that the monoanionic OSILs showed lower toxicity than the corresponding dianionic structures to all cell types. The highest cytotoxic effect was observed in OSILs containing a [C2OHMIM] cation, in particular [C2OHMIM][ALN]. The latter showed an improvement in IC50 values of ca. three orders of magnitude for the lung and bone cancer cell lines as well as fibroblasts in comparison with ALN. The development of OSILs with high cytotoxicity effect towards the tested cancer cell types, and containing an anti-resorbing molecule such as ALN may represent a promising strategy for the development of new pharmacological tools to be used in those pathological conditions.

| S-EPMC7151258 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data