1-Methyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
[CAS# 174899-81-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 1-Methyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
• Synonyms: 1,3-Dimethylimidazolium bis[(trifluoromethyl)sulfonyl]imide; 1-Methyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide
• Molecular Formula: C₅H₉N₂.C₂F₆NO₄S₂
• Molecular Weight: 377.29
• CAS Registry Number: 174899-81-1
• EC Number: 801-349-9
• SMILES: CN1C=C[N+](=C1)C.C(F)(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F

Properties

• Density: 1.574 g/cm³ (20 °C)^*
• Melting point: 26 °C^**
• Refractive index: 1.422 (25 °C)^**

^* Bogdanov, Milen G.

^** Buffeteau, Thierry

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1-Methyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide (MMIM TFSI) is a unique ionic liquid known for its exceptional properties and wide range of applications. With the molecular formula C8H10F6N2O4S2, MMIM TFSI belongs to a class of organic salts that remain liquid at ambient temperature and have unique applications in a variety of scientific and industrial purposes.

The synthesis and exploration of MMIM TFSI was part of the extensive research on ionic liquids that rose to prominence in the late 20th century. Researchers aimed to develop solvents with superior properties compared to traditional organic solvents, including low volatility, high thermal stability, and a wide electrochemical window. MMIM TFSI was developed to provide these advantages by combining a methyl-substituted imidazolium cation with a bis(trifluoromethyl)sulfonyl imide anion, thus addressing the need for solvents and electrolytes with enhanced performance characteristics.

The synthesis of MMIM TFSI involves the reaction of 1-methyl-3-methylimidazolium chloride (MMIM Cl) with lithium bis(trifluoromethyl)sulfonyl imide (LiTFSI). During this process, MMIM Cl reacts with LiTFSI to form MMIM TFSI and lithium chloride (LiCl) as a byproduct. The reaction takes place in a suitable solvent or directly in an ionic liquid phase, followed by purification to obtain the desired product.

MMIM TFSI is widely used in electrochemical applications due to its excellent ionic conductivity and wide electrochemical stability window. It can be used as an electrolyte in a variety of energy storage devices, including lithium-ion batteries, supercapacitors, and fuel cells. Its low viscosity and high thermal stability help improve the performance and efficiency of these devices, making it an important component in advanced energy technologies.

As a green solvent, MMIM TFSI has advantages over traditional organic solvents, which are volatile and toxic. MMIM TFSI is non-volatile and recyclable, making it an environmentally friendly alternative for chemical processes. It is used in organic synthesis and extraction processes, and its ability to dissolve a wide range of compounds can improve reaction efficiency and selectivity.

In catalysis, MMIM TFSI can be used as both a solvent and a co-catalyst. Its ability to dissolve a wide range of organic and inorganic compounds makes it a versatile medium for catalytic reactions. MMIM TFSI is used in homogeneous and heterogeneous catalysis to promote reactions such as hydrogenation, oxidation, and polymerization. Its use can lead to more efficient and selective reactions, contributing to sustainable chemical synthesis.

MMIM TFSI is very effective in separation processes, including liquid-liquid extraction and gas absorption. Its unique solvation properties allow for the selective extraction and separation of specific compounds from a mixture. This application is valuable in drug purification, metal extraction, and separation of organic compounds, improving process efficiency and selectivity.

In materials science, MMIM TFSI is used to synthesize and modify materials with specific properties. It plays a role in the preparation of nanoparticles, polymers, and other advanced materials. MMIM TFSI can act as a template or stabilizer during the synthesis of nanomaterials, affecting their size, shape, and stability, and leading to the development of new materials with customized properties.

References

2023. Structure and Reactivity of the Ionic Liquid [C1C1Im][Tf2N] on Cu(111). Topics in Catalysis.
DOI: 10.1007/s11244-023-01801-y

2021. Intermolecular Vibrations in Aprotic Molecular Liquids and Ionic Liquids. Molecular Basics of Liquids and Liquid-Based Materials.
DOI: 10.1007/978-981-16-5395-7_7

2019. Review of Ionic Liquids in Microextraction Analysis of Pesticide Residues in Fruit and Vegetable Samples. Chromatographia.
DOI: 10.1007/s10337-019-03818-6