148019-49-2

Basic information

• Product Name: 3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate
• CAS NO: 148019-49-2
• Molecular Weight: 204.25
• Mol File: 148019-49-2.mol
• Article Data: 76

Chemical Properties

• CAS DataBase Reference: 3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate(148019-49-2)
• EPA Substance Registry System: 3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate(148019-49-2)

Safety Data

• Hazardous Substances Data: 148019-49-2(Hazardous Substances Data)

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 1633-83-6 1,4-butane sultone 
• 7732-18-5 water 
• 5687-92-3 thiethane 1,1-dioxide 
• 1120-71-4 1,3-propanesultone 

Relevant articles and documents

Performance of Br?nsted-Lewis acidic ionic liquids supported Ti-SBA-15 for the esterification of acetic acid to benzyl alcohol

Br?nsted-Lewis acidic ionic liquids (BLAILs)[3-methyl-1-(3-sulfonic acid) imidazolium zinc sulfate ([MIMPS]+(1/2Zn2+)SO42?)] with Br?nsted acid ionic liquid [MIMPS]+HSO4- and ZnO were synthesized, and their acidities were determined by infrared pyridine probe. Ti doped SBA-15 mesoporous molecular sieves (Ti-SBA-15) were synthesized by co-condensation method. Ionic liquid [MIMPS]+(1/2Zn2+)SO42? and Ti-SBA-15 are compounded at different mass ratios by impregnation method. FT-IR, TG, XRD, N2 physical adsorption, elemental analysis, mass spectroscopy, TEM, and XPS were used to characterize the composition and structure of the catalysts. The catalytic activities of catalysts were investigated via esterification of acetic acid with benzyl alcohol (BnOH). When the reaction temperature is 90 ℃, reaction time is 3 h, nbenzyl alcohol/nacetic acid =1.8, and the amount of catalyst was 0.4 g, the conversion of acetic acid was as high as 93.8 %. After 5 cycles, the conversion of acetic acid decreased only 5%, suggesting that the resulting catalyst had good stability.

Addition of suitably-designed zwitterions improves the saturated water content of hydrophobic ionic liquids

The saturated water content in a hydrophobic ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)-imide, was improved from 0.4 wt% to 17.8 wt% by adding a 3-(1-butyl-3-imidazolio)propanesulfonate- type zwitterion in appropriate amounts. The mixture containing 17.8 wt% water successfully dissolved horse heart cytochrome c without significant change of the higher ordered structure.

Synthesis of immobilized heteropolyanion-based ionic liquids on mesoporous silica SBA-15 as a heterogeneous catalyst for alkylation

Phosphotungstic acid (H3PW12O40) has been successfully loaded onto sulfonate-functionalized ionic liquid-modified mesoporous silica SBA-15 by total anion-exchange. The immobilized catalysts were characterized by XRD, N2 adsorption, TEM, and FTIR spectroscopy. Characterization results show that the mesopore structure of SBA-15 was maintained well even after surface modification and the subsequent anion-exchange step of [PW12O40]3- (PW). In comparison with the task-specific basic ionic liquid (1-(propyl-3-sulfonate) 3-methyl-imidazolium phosphotungstate), the obtained catalyst showed much higher efficiency in alkylation of o-xylene with styrene. More importantly, such an immobilized task-specific basic ionic liquid could be reused without significant loss of catalytic activity even after recycling six times. This journal is the Partner Organisations 2014.

Synthesis and thermophysical properties of imidazolium-based bronsted acidic ionic liquids

A range of imidazolium-based Bronsted acidic ionic liquids (ILs) have been synthesized by varying the side chain length of the alkyl and alkyl sulfonic group incorporated to the C1 and C3 positions in the imidazolium ring respectively with a fixed HSO4- anion. The synthesized ILs were characterized using NMR for structure confirmation and CHNS for elemental analysis. The thermal properties such as thermal decomposition temperature were determined using thermogravimetric analysis, and several key physical properties such as viscosity and density were measured within a temperature range of 20 C to 80 C using an Anton Paar viscometer and densitometer. The density measurement results and established equations were used to calculate the molecular volumes, standard entropies, crystal lattice energies, and thermal expansion coefficients of the synthesized ILs.

Silica ionogels for proton transport

A number of ionogels - silica-ionic liquid (IL) hybrid materials - were synthesized and studied for their ionic conductivity. The materials are based on a sulfonated IL, 1-methyl-3-(3-sulfopropyl-)-imidazolium p-toluenesulfonate, [PmimSO3H][PTS], which contains a sulfonic acid/sulfonate group both in the IL anion and in the side chain of the IL cation. By way of the sulfonate-sulfonic acid proton transfer, the IL imparts the ionogel with a high ionic conductivity of ca. 10-2 S cm-1 in the as-synthesized state at 120 °C and 10-3 S cm-1 in the dry state at 120 °C. The ionogels are stable up to ca. 150 °C in dynamic thermogravimetric analysis. This suggests that these materials, which are relatively cheap and easily fabricated, could find application in fuel cells in intermediate temperature ranges where many other membrane materials are not suitable. The Royal Society of Chemistry 2012.

Improved 1-butene/isobutane alkylation with acidic ionic liquids and tunable acid/ionic liquid mixtures

A new process for 1-butene/isobutane alkylation to yield C 8-alkylates is described using binary mixtures of certain acidic imidazolium ionic liquids (ILs) and strong acids such as sulfuric or trifluoromethanesulfonic (triflic) acid. Equivalent or better conversion (>95%), C8-alkylates selectivity (>70%) and trimethylpentane/ dimethylhexane selectivity (TMP/DMH > 7) were achieved with the IL/acid mixtures over the pure acids themselves. Six types of substituted 3-methyl-imidazolium ionic liquids were investigated, wherein acidity is imparted via either the cation with sulfonic acid groups or the anion (hydrogen sulfate) or both. Long-term studies up to 30+ recycles indicate that the catalyst stability was increased by sometimes greater than 30+% with the IL/acid mixtures over the pure acid. The ionic liquid is believed to tune the acidity, solubility, and interfacial properties, resulting in these enhanced results. In addition, this concept could also be applicable to Friedel-Crafts alkylation, acylation chemistries, or other acid-catalyzed reactions.

Sulfonated palladium(II) N-heterocyclic carbene complex immobilized on nano-micro size poly(4-vinylpyridinium chloride) for Suzuki-Miyaura cross-coupling reaction

The sulfonated palladium(II) N-heterocyclic carbene complex PdII(NHC)SO3-, supported on poly(4-vinylpyridinium chloride), was used as a heterogeneous, recyclable and active catalyst for the Suzuki-Miyaura reaction. This catalyst was applied for coupling of various aryl halides with phenylboronic acid and the corresponding products were obtained in excellent yields and short reaction times. The catalyst was characterized using Fourier transform infrared and diffuse reflectance UV-visible spectroscopies, scanning electron microscopy and elemental analysis. After each reaction, the catalyst was recovered easily by simple filtration and reused several times without significant loss of its catalytic activity.

Palladium catalysts with sulfonate-functionalized-NHC ligands for Suzuki-Miyaura cross-coupling reactions in water

Four new Pd(II) complexes containing sulfonate-functionalized N-heterocyclic carbene ligands have been synthesized. All new complexes are palladium bis-NHCs, in which the ligands adopt a monodentate, bis-chelating, and pincer coordination form, so that a good comparison between their catalytic activities can be performed. The complexes have been used in the Suzuki-Miyaura cross-coupling reaction between aryl halides and phenylboronic acid in water and in iPrOH/water. The bis-NHC-palladium complex 1, in which the two NHC ligands are in a relative cis configuration, affords the best catalytic outcomes, with high TON values of 105 for 4-bromoacetophenone and 3.7 - 104 for 4-chloroacetophenone.

SO3H-functionalized acidic ionic liquids as catalysts for the hydrolysis of cellulose

The conversion of cellulose into valuable chemicals to deal with the depletion of fossil fuel has got much attention. Completing the hydrolysis of cellulose under mild conditions is the key step. In this study, six kinds of SO3H-functionalized acidic ionic liquids were used as acid catalyst to promote the hydrolysis of cellulose in 1-butyl-3-methylimidazolium chloride ([BMIM]Cl). All of them were efficient for the hydrolysis of cellulose, with the maximum total reducing sugars (TRS) yields over 83% at 100 °C. Acidic ionic liquids with analogous structures showed similar catalytic activities. Triethyl-(3-sulfo-propyl)-ammonium hydrogen sulfate (IL-5 in this study) was the optimum ionic liquid for cellulose hydrolysis, with the maximum TRS yield at 100 °C up to 99% when the dosage used was 0.2 g. In addition, the water in [BMIM]Cl had negative effect on cellulose hydrolysis. Therefore, controlling the content of water in a comparatively low level is quite necessary.

Tracking the transition behavior and dynamics of ionic transport in crystalline ionic gel electrolytes

The transition behavior and dynamics of ionic transport were strongly influenced by changes in the crystal structure and interaction field of the crystalline ionic gel electrolytes with respect to chemical compositions, as proven by impedance, 7Li NMR, PCA and 2D IR COS.

Polysulfide Regulation by the Zwitterionic Barrier toward Durable Lithium-Sulfur Batteries

Rational regulation on polysulfide behaviors is of great significance in pursuit of reliable solution-based lithium-sulfur (Li-S) battery chemistry. Herein, we develop a unique polymeric zwitterion (PZI) to establish a smart polysulfide regulation in Li-S batteries. The zwitterionic nature of PZI integrates sulfophilicity and lithiophilicity in the matrix, fostering an ionic environment for selective ion transfer through the chemical interactions with lithium polysulfides (LiPS). When implemented as a functional interlayer in the cell configuration, PZI empowers strong obstruction against polysulfide permeation but simultaneously allows fast Li+ conduction, thus contributing to significant shuttle inhibition as well as the resultant facile and stable sulfur electrochemistry. The PZI-based cells realize excellent cyclability over 1000 cycles with a minimum capacity fading rate of 0.012% per cycle and favorable rate capability up to 5 C. Moreover, a high areal capacity retention of 5.3 mAh cm-2 after 300 cycles can be also obtained under raised sulfur loading and limited electrolyte, demonstrating great promise in developing high-efficiency and long-lasting Li-S batteries.

p-Toluenesulfonic acid functionalized imidazole ionic liquids encapsulated into bismuth SBA-16 as high-efficiency catalysts for Friedel-Crafts acylation reaction

Bismuth SBA-16 catalyst was synthesized by the hydrothermal method. Four kinds ofp-toluenesulfonic acid functionalized imidazole ionic liquids were prepared by a two-step method and their molecular structures were characterized by1H NMR and MS. The post-synthesis impregnation method was used to functionalize the Bi(10)-SBA-16 silicon mesoporous material with the ionic liquids and the obtained materials were characterized by FT-IR, XRD, BET, XPS, and TG. The results show that the volume and pore size of SBA-16 were changed by loading Bi and ionic liquids, while the three-dimensional cubic pore structure of SBA-16 was not destroyed. The composite catalyst was evaluated in Friedel-Crafts acylation of anisole with acetic anhydride. The effects of reaction temperature and the ratio of anisole and acylating agent on the acylation of anisole were investigated by experimental design. The results showed that 1.2ILc@Bi(10)-SBA-16 was used as the catalyst, the conversion of anisole was 85.41% and the yield of aromatic ketone was 69.19% under the conditions of a reaction temperature of 100 °C, a catalyst dosage of 0.5 g, a time period of 4 h and a molar ratio of 1?:?1.5. After 5 recycling runs, the reduction in the overall ratio of reactant conversion and product yield did not exceed 7.5%, indicating that 1.2ILc@Bi(10)-SBA-16 has good stability and reusability.

Hybrid Liquid-Crystalline Electrolytes with High-Temperature-Stable Channels for Anhydrous Proton Conduction

Modern electrochemical and electronic devices require advanced electrolytes. Liquid crystals have emerged as promising electrolyte candidates due to their good fluidity and long-range order. However, the mesophase of liquid crystals is variable upon heating, which limits their applications as high-temperature electrolytes, e.g., implementing anhydrous proton conduction above 100 °C. Here, we report a highly stable thermotropic liquid-crystalline electrolyte based on the electrostatic self-assembly of polyoxometalate (POM) clusters and zwitterionic polymer ligands. These electrolytes can form a well-ordered mesophase with sub-10 nm POM-based columnar domains, attributed to the dynamic rearrangement of polymer ligands on POM surfaces. Notably, POMs can serve as both electrostatic cross-linkers and high proton conductors, which enable the columnar domains to be high-temperature-stable channels for anhydrous proton conduction. These nanochannels can maintain constant columnar structures in a wide temperature range from 90 to 160 °C. This work demonstrates the unique role of POMs in developing high-performance liquid-crystalline electrolytes, which can provide a new route to design advanced ion transport systems for energy and electronic applications.