1-Ethyl-3-methylimidazolium trifluoromethanesulfonate
[CAS# 145022-44-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ionic liquid
• Name: 1-Ethyl-3-methylimidazolium trifluoromethanesulfonate
• Molecular Formula: C₇H₁₁F₃N₂O₃S
• Molecular Weight: 260.23
• CAS Registry Number: 145022-44-2
• EC Number: 680-002-1
• SMILES: CCN1C=C[N+](=C1)C.C(F)(F)(F)S(=O)(=O)[O-]

Properties

• Density: 1.387
• Boiling point: >350 °C
• Refractive index: 1.435
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

1-Ethyl-3-methylimidazolium trifluoromethanesulfonate (EMIM OTf) is an ionic liquid known for its unique properties and wide range of applications in various fields. With the molecular formula C7H11F3N2O3S, EMIM OTf belongs to a class of organic salts that are liquid at relatively low temperatures, making it useful in a wide range of industrial and research applications.

The discovery of ionic liquids such as EMIM OTf dates back to the mid-20th century, when researchers began to explore the potential of organic salts with melting points below 100°C. EMIM OTf itself is a relatively recent development, and its synthesis is intended to exploit the favorable properties of ionic liquids, such as low volatility, high thermal stability, and excellent solvency. The synthesis involves the reaction of 1-ethyl-3-methylimidazolium chloride with silver trifluoromethanesulfonate, exchanging the chloride ion with the trifluoromethanesulfonate ion to produce EMIM OTf.

During the synthesis of EMIM OTf, 1-ethyl-3-methylimidazolium chloride (EMIM Cl) reacts with silver trifluoromethanesulfonate (AgOTf) to produce EMIM OTf and silver chloride (AgCl) as a byproduct. The reaction usually takes place in a suitable solvent, followed by purification to isolate the desired ionic liquid.

The most important application of EMIM OTf is as a green solvent in various chemical reactions. Traditional organic solvents often pose environmental and health hazards due to their volatility and toxicity. In contrast, EMIM OTf is non-volatile and can be reused, thus reducing the environmental impact of chemical processes. It is particularly useful in catalysis, where it can dissolve a variety of organic and inorganic compounds and increase reaction rates and selectivity.

EMIM OTf is widely used in electrochemical applications due to its high ionic conductivity and stability. It can be used as an electrolyte in batteries, fuel cells, and supercapacitors, helping to improve efficiency and performance. Its wide electrochemical window and low viscosity make it an excellent choice for these applications, enabling the development of advanced energy storage and conversion devices.

In the field of extraction and separation, EMIM OTf is used to extract valuable compounds from various mixtures. Its ability to dissolve both polar and non-polar substances allows for efficient extraction of target molecules, such as bioactive compounds from plant materials or metals from ores. In addition, its low volatility and recyclability make it an environmentally friendly alternative to traditional solvents in extraction processes.

EMIM OTf can be used in the pharmaceutical industry, especially in drug formulation and delivery. Its unique properties enable the solubilization and stabilization of poorly soluble drugs, thereby improving their bioavailability. In addition, its use in drug synthesis can lead to more efficient and selective reactions, aiding in the development of new drugs.

In catalysis, EMIM OTf can act as both a solvent and a catalyst to promote various chemical transformations. Its ability to stabilize transition states and intermediates can increase reaction rates and yields. EMIM OTf is used in organic synthesis, polymerization reactions, and the production of fine chemicals, contributing to cleaner and more sustainable processes.

References

2024-06. The iontronic sensor based on biodegradable polycaprolactone for interfacial capacitive pressure sensing
DOI: 10.1007/s10854-024-12808-w

2023-07-29. Recent advances in the use of ionic liquids in the CO2 conversion to CO and C2+ hydrocarbons
DOI: 10.1007/s10098-023-02583-3

2023-06-28. Synthesis of poly(vinyl acetate)-based gel polymer electrolyte for application in electric double layer capacitors
DOI: 10.1007/s11581-023-05104-w