179863-07-1

Basic information

• Product Name: 1-MethyliMidazoliuM sulfobutyrolactone
• Synonyms: 1-MethyliMidazoliuM sulfobutyrolactone;BSO3MIM;1-Butylsulfonic-3-methylimid azolium;1-(4-Sulfobutyl)-3-methylimidazolium betaine;1-Methyl-3-(4-sulfobutyl)-1H-imidazolium inner salt;4-(1-Methylimidazolium-3-yl)butane-1-sulfonate
• CAS NO: 179863-07-1
• Molecular Formula: C9H14N2O5S
• Molecular Weight: 262.28286
• Mol File: 179863-07-1.mol
• Article Data: 47

Chemical Properties

• Melting Point: 217.30 °C(Solv: methanol (67-56-1))
• Appearance: /
• CAS DataBase Reference: 1-MethyliMidazoliuM sulfobutyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-MethyliMidazoliuM sulfobutyrolactone(179863-07-1)
• EPA Substance Registry System: 1-MethyliMidazoliuM sulfobutyrolactone(179863-07-1)

Safety Data

• Hazardous Substances Data: 179863-07-1(Hazardous Substances Data)

Usage

General Description

1-Methylimidazolium sulfobutyrolactone is a chemical compound that is a type of ionic liquid, also known as a room temperature ionic liquid (RTIL). It is formed by combining 1-methylimidazole, a basic heterocyclic compound, with sulfobutyrolactone, a sulfonic acid. This combination results in a stable and versatile ionic liquid that is often used as a solvent or electrolyte in various applications, including electrochemistry, catalysis, and as a reaction medium. Its unique properties, such as high thermal stability, low volatility, and good solvation capabilities, make it valuable in industrial and research settings for a wide range of purposes. Additionally, its environmentally friendly nature, due to its low toxicity and biodegradability, has led to its increasing use in green chemistry and sustainable processes.

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 1633-83-6 1,4-butane sultone 
• 2386-47-2 butane-1-sulfonic acid 

Downstream Products

• 909390-59-6 3-methyl-1-(4-sulfobutyl)imidazol-3-ium bis((trifluoromethyl)sulfonyl)azanide 

Relevant articles and documents

Decision support towards agile eco-design of microreaction processes by accompanying (simplified) life cycle assessment

Continuously running syntheses in microstructured reactors offers novel ways to intensify conventional chemical processes. An outstanding advantage of microreaction technology is the high surface-to-volume-ratio which enables intensive mixing phenomena as well as high mass and heat transfer rates. Thus, microstructured reactors may be a suitable means to improve multiphase reactions by increasing the interfacial area and the intensification of internal mixing. This improvement in reaction performances may lead to reduced environmental burdens of the process under consideration. The method of simplified life cycle assessment (SLCA) is a suitable tool to evaluate the environmental burdens caused by chemical processes. It has been applied already in research and development to identify the key parameters for a deliberate green process design of two biphasic reactions, the esterification of phenol and benzoyl chloride resulting in phenyl benzoate and the synthesis of one of the corresponding phase transfer catalysts, [BMIM]Cl. Further, SLCA is complemented by a simple cost estimation to investigate the main cost drivers relevant for possible industrial application of the syntheses investigated.

Catalytic hydrolysis of cellulose into furans in MnCl2-ionic liquid system

Production of 5-hydroxymethylfurfural (HMF) and furfural from microcrystalline cellulose (MCC) was studied in 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate (IL-1) with catalytic amount of MnCl2 under atmospheric pressure within 300 min at 150 °C, in which 88.62% of conversion was obtained. With the presence of a catalytic amount of MnCl2, HMF and furfural yields were up to 37% and 18%, respectively, and generated small amount of levulinic acid (LA) and the total reducing sugars (TRS). Dimer of furans compounds as the important by-products were analyzed through HPLC-MS; some small molecular substances, methane, ethane, CO, CO2 and H2, as gas products were detected using mass spectrometry analysis. Comparing with the previous reports, our catalytic system is simple, and it provides an effective route for the conversion of microcrystalline cellulose into biofuels and important platform chemicals.

Direct hydroxylation of p-xylene to 2,5-xylenol with hydroxylamine in ionic liquids/molybdenum catalytic system

Direct hydroxylation of p-xylene to 2,5-xylenol with hydroxylamine was carried out in an ionic liquids/molybdenum catalytic system. High 2,5-xylenol selectivity (80-98 %) can be achieved with good p-xylene conversion (5.9-9.9 %) in this catalytic system. The recycling experiments suggested the ionic liquids/molybdenum catalytic system was stable enough to be recycled for the hydroxylation reaction.

Anionic SO3H-functionalized ionic liquid: An efficient and recyclable catalyst for the Pechmann reaction of phenols with ethyl acetoacetate

This paper has reported an anionic SO3H-functionalized ionic liquid N-methylimidazolium sulfomethylsulfonate ([Hmim][HO3SCH2SO3]) for the synthesis of coumarins by Pechmann reaction. The [Hmim][HO3SCH2SO3] is easier to prepare by one-step neutralization reaction of N-methylimidazole with methanedisulfonic acid and show high catalytic performance for Pechmann reaction. Besides, the catalyst can simply be separated from the reaction mixture and recycled ten times without noticeable loss of activity.

CFacile biodiesel synthesis from esterification of free fatty acids catalyzed by SO3H-Functionalized Ionic Liquid

The esterifications of free fatty acids with methanol were efficiently accomplished over a SO3H-functionalized ionic liquid, 1-(4-sulphonic acid)butyl-3-methylimidazolium hydrogen sulphate ([BSMim]HSO4), which are commonly considered as both one of the typical synthetic routes and the representative pretreatment process for biodiesel production. Particularly, the maximum yield of methyl oleate was obtained in 99.9 %. Methyl oleate could be isolated through simple decantation from the biphasic system, which is attributed to the immiscibility of [BSMim]HSO4 with hydrophobic ester and the good stability and operability of ionic liquid were demonstrated by the six times reuses without dramatic decrease in methyl oleate yield.

Imidazolium-based zwitterionic butane-1-sulfonates: Synthesis and properties of 4-(1-(2-Cyanoethyl)imidazolium)butane-1-sulfonate and Crystal Structures of 4-(1-Alkylimidazolium)butane-1-sulfonates (Alkyl = Methyl, Ethyl, Propyl)

The reaction of 1-alkylimidazoles (alkyl = methyl, ethyl, propyl, 2-cyanoethyl) with 1,4-butane sultone in equimolar stoichiometry resulted in the formation of 4-(1-methylimidazolium)butane-1-sulfonate SBMIm, 4-(1-ethylimidazolium)butane-1-sulfonate SBEIm, 4-(1-propylimidazolium)butane-1- sulfonate SBPIm, and 4-(1-(2-cyanoethyl)imidazolium)butane-1-sulfonate SBCNEtIm, respectively, in high yields. Properties of these four imidazolium-based zwitterionic compounds were investigated with respect to question of their use as suitable precursors for Ionic Liquids. The structures of the compounds SBMIm, SBEIm, and SBPIm were determined by single-crystal X-ray diffraction. SBMIm and SBEIm crystallize both in the triclinic space group P 1, SBMIm: a = 8.4454(6), b = 8.4492(6), c = 8.7532(7) A, α = 66.610(2), β = 66.235(2), γ = 70.625(2)°, Z = 2, R1(F)/wR2(F2) = 0.0279/0.0832; SBEIm: a = 8.4359(2), b = 8.5900(2), c = 8.6790(2) A, α = 73.487(2), β = 71.228(1), γ = 70.979(2)°, Z = 2, R1(F)/wR2(F2) = 0.0333/0.0820; SBPIm with monoclinic symmetry, space group P21/c: Z = 4; a = 7.2979(3), b = 17.5312(8), c = 9.5682(4) A, β = 90.922(3)°, R1(F)/wR2(F2) = 0.0507/0.1198. Copyright

Bronsted acid ionic liquid catalyzed formation of pyruvaldehyde dimethylacetal from triose sugars

A series of sulfonic acid functionalized ionic liquids (SO 3H-ILs) have been synthesized, characterized and investigated as catalysts for the conversion of the triose sugars, 1,3-dihydroxyacetone (DHA) and glyceraldehyde (GLA), to pyruvaldehyde dimethylacetal (PADA) in methanol. Depending on the reaction conditions and the applied SO3H-ILs a good yield of up to 52% of PADA was obtained. Under identical reaction conditions the derivative of PADA, 1,1,2,2-tetramethoxy propane (TMP), could be obtained in yields up to 49% using another SO3H-IL.

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.

Mechanistic studies on counter-ionic effects of camphorsulfonate-based ionic liquids on kinetics, thermodynamics and stereoselectivity of β-amino carbonyl compounds

Catalysis is important in various applications of organic chemistry and its output product control for stereoselective compounds is outrageous. Establishment of experimental facts of stereoselective compounds from catalysis and their validation using theoretical evidences is the key to understand various mechanisms of optically active compounds. A family of new ionic liquids (ILs) with various imidazolium cations and camphorsulfonate anion as environmentally benign liquid salts have been synthesized and deployed for catalysis of β-amino carbonyl compounds. The products were formed using ILs as a homogeneous catalyst with excellent product yield and diastereoselectivity. The effect of counter ions, Hammett acidity and viscosity of ILs along with solvent and temperature are explored in terms of reaction kinetics and product yields. Density functional theory (DFT) was used to investigate thermodynamical study of mechanistic pathway of the reaction. The DFT calculations predicted that the catalysis mechanism involved both counterions of the IL. Moreover, it is evidenced that the syn-pathway required lower activation energy while anti-pathway led to thermodynamically stable product. This study explores new avenues for using ILs as potential homogeneous catalysts for the production of stereoselective species.