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1-Ethyl-3-methylimidazolium chloride (abbreviated as [EMIm]Cl or EMIC) is an organic salt belonging to the ionic liquid class. Molecular formula C6H11ClN2, CAS 65039-09-0. It is a light yellow to yellow transparent liquid with no fixed solid form. Ionic liquids are ionic compounds that are liquid at or near room temperature. It is an ionic compound, therefore it has good conductivity. This cation is composed of a five membered ring with two nitrogen atoms and three carbon atoms, namely an imidazole derivative, which replaces the ethyl and methyl groups at the two nitrogen atoms. It is an organic chloride salt and ionic liquid containing 1-ethyl-3-methylimidazolium. It is an organic chloride salt, with a cationic component of 1-ethyl-3-methylimidazole. Its conductivity at a certain concentration depends on its composition and concentration, and can reach a higher level. Has a slight irritating odor, and appropriate protective measures should be taken after prolonged contact. It has wide applications in many fields, such as chemical reaction media, electrochemical energy storage systems, extraction and separation, etc. It is an ionic compound, therefore it has good conductivity. Its conductivity at a certain concentration depends on its composition and concentration, and can reach a higher level. As an ionic liquid, it has important application value in electrochemical energy storage systems. It can be used as an electrolyte or additive in fields such as secondary batteries, capacitors, supercapacitors, and fuel cells to improve the performance and stability of energy storage equipment. It is an ionic liquid that can be used for cellulose processing.
|
Chemical Formula |
C4H2KN3O4- |
|
Exact Mass |
195 |
|
Molecular Weight |
195 |
|
m/z |
195 (100.0%), 196, (4.3%), 197 (4.3%) |
|
Elemental Analysis |
C, 24.62; H, 1.03; N, 21.53; O, 32.79 |
Melting point 77-79 ° C (lit.), Density 1.435 g/cm3, Flash point 186 ° C, Storage condition store below +30 ° C, Morphology agglomerating crystal powder, Color pale yellow, Soluble in water, Sensitivity hygroscopic, BRN 5163190, Stable Very hygroscopic. Incompatible with strong oxidizing agents., InChIKeyBMQZYMYBQZGEEY-UHFFFAOYSA-M, Warning, Hazard description h315-h319-h413, Precautions p264-p280a-p321-p332+p313-p337+p313-p305+p351+p338, Dangerous goods sign Xi, N, t, Hazard category code 36/38-51/53-36/37/38-25, Safety instructions 26-57-45-37/39-29, Dangerous goods transport No. 2811, WGK Germany 2, F 3-10, TSCA Yes.
Because 1-Ethyl-3-methylimidazolium Chloride is widely used, understanding its synthesis methods and process conditions is of great significance for the study and application of this compound. At present, there are various reports on the synthesis methods of 1-ethyl-3-methylimidazole chloride, and one of the commonly used methods will be introduced.
The main steps of this method are as follows: synthesis of thiourea, reaction of thiourea with 1-ethyl-3-methylimidazole, and chlorination reaction.
1. Firstly, thiourea can be prepared by the reaction of ammonium sulfite and sodium carbonate. The reaction takes place at a certain temperature, with reactants mixed in a certain molar ratio and an appropriate amount of solvent added. After a period of reaction, the product can be obtained through filtration, crystallization, and other methods. The preparation conditions of thiourea need to be strictly controlled to ensure a high-purity product.
2. Next, the prepared thiourea will react with 1-ethyl-3-methylimidazole in an appropriate solvent. This reaction is usually carried out at a certain temperature and an appropriate amount of catalyst is added. The reaction time should be adjusted according to the experimental results to achieve the desired reaction effect. After the reaction, 1-ethyl-3-methylimidazole chloride can be obtained through filtration, purification, and other methods.
3. Finally, perform a chlorination reaction on the obtained product. The chlorination reaction is a crucial step in introducing chlorine atoms into the target compound. This reaction needs to be carried out at a certain temperature and pH value, with the addition of an appropriate amount of chlorinating agent. The reaction process requires strict control of temperature and reaction time to ensure high yield and purity of the product. After the reaction is completed, the product can be obtained as pure 1-ethyl-3-methylimidazole chloride through crystallization, washing, and other methods.
1-Ethyl-3-methylimidazolium Chloride (CAS number 65039-09-0) is a typical precursor of imidazolium ionic liquids. In its molecular structure, the N-1 position of the imidazole ring is replaced by an ethyl group and the N-3 position is replaced by a methyl group, forming a stable cationic skeleton. When combined with chloride ions, it exhibits unique physicochemical properties. This compound has demonstrated extensive application value in fields such as ionic liquid synthesis, catalytic reactions, materials science, biomass conversion, environmental governance, and electronics industry due to its low volatility, high thermal stability, strong solubility, and designability.
It is a key precursor for the preparation of imidazole ionic liquids, which can be functionalized by exchanging with metal chlorides (such as AlCl3, ZnCl ₂) or organic anions (such as BF ₄⁻, PF ₆⁻). For example:
Composite with AlCl3: forms an acidic ionic liquid for Friedel Crafts alkylation reaction, catalyzing the alkylation of benzene with long-chain olefins to produce straight chain alkylbenzene with a yield of over 90% and selectivity superior to traditional Lewis acid catalysts (such as H ₂ SO ₄).
Exchange with BF ₄⁻: Generate hydrophobic ionic liquids as efficient extractants for separating metal ions (such as Pb ² ⁺, Cd ² ⁺) or organic pollutants (such as phenols and dyes) in aqueous solutions, with a distribution coefficient 3-5 times higher than traditional solvents.
Combined with PF ₆⁻: Preparation of highly conductive ionic liquids for use in lithium-ion battery electrolytes, significantly improving battery cycling stability (capacity retention rate>85% after 500 cycles).
Technical advantages: Ionic liquids achieve solvent performance regulation through the synergistic effect of anions and cations, which can replace volatile organic solvents (VOCs), reduce environmental pollution, and comply with green chemistry principles.
Its derivatives have shown outstanding performance in the field of catalysis, and can be used independently as catalysts or as reaction media to improve reaction efficiency
Acid catalyzed reaction: Ionic liquids formed with AlCl3 exhibit high activity in alkylation and acylation reactions. For example, in the alkylation reaction of benzene with dodecene, ionic liquid catalysts increase the selectivity of the target product (linear dodecylbenzene) from 65% to 92%, while reducing the by-product (branched alkylbenzene) to below 8%.
Enzyme catalyzed reaction: As a co solvent, it improves the enzyme catalytic environment.
For example, in lipase catalyzed ester exchange reactions, adding 5% 1-ethyl-3-methylimidazole chloride can increase the reaction rate by 2 times and extend the enzyme half-life to over 30 days.
Photocatalytic reaction: Preparation of photocatalyst by composite with TiO ₂ for degradation of organic pollutants (such as bisphenol A). Experiments have shown that under UV irradiation, the degradation rate of bisphenol A by composite catalysts is 40% higher than that of pure TiO ₂, and can be recycled more than 10 times.
Technical principle: The π - electron cloud of the imidazole ring forms a strongly polar environment with the lone pair electrons of the chloride ion, stabilizing the reaction intermediates and reducing the activation energy, thereby accelerating the reaction process.
The applications in the field of materials cover the preparation of polymers, nanomaterials, and composite materials
Surface imprinted polymer: Using this substance as a template molecule, methacrylic acid and ethylene glycol dimethacrylate as bifunctional monomers, and polystyrene divinylbenzene as a carrier, a highly selective adsorption material is prepared. The polymer has an adsorption capacity of 120mg/g for template molecules and a selectivity coefficient of 5.2 for structurally similar compounds such as 1-butyl-3-methylimidazole.
Nanomaterial synthesis: as a structural directing agent to regulate the morphology of nanoparticles.
For example, when synthesizing ZnO nanorods, adding 1-Ethyl-3-methylimidazolium chloride can reduce the diameter of the nanorods from 100nm to 30nm, extend the length from 500nm to 2 μ m, and increase the crystallinity to over 95%.
Conductive composite materials: Preparation of highly conductive materials by compounding with carbon nanotubes (CNT). Experiments have shown that adding 10% of this substance to CNT composite materials results in a conductivity of 10 ⁴ S/m, which is 2 orders of magnitude higher than pure CNT.
Application case: Surface imprinted polymers have been used for solid-phase extraction (SPE) column preparation, combined with high-performance liquid chromatography (HPLC), to selectively separate and enrich ionic liquid pollutants in water samples, with a detection limit as low as 0.1 μ g/L.
Has demonstrated significant value in the field of biomass conversion, particularly in the preparation of 5-hydroxymethylfurfural (HMF):
HMF synthesis: Using fructose as the raw material, its ionic liquid as the solvent, and superhydrophobic solid acid (such as sulfonated carbon nanotubes) as the catalyst, the HMF yield reached 85% after 6 hours of reaction at 120 ℃, which is 30% higher than traditional methods (such as H ₂ SO ₄ catalysis). Its advantages lie in:
Ionic liquids have strong ability to dissolve fructose and high uniformity of the reaction system;
Superhydrophobic catalysts inhibit HMF hydrolysis and improve selectivity;
The product is easy to separate, and the catalyst can be recycled.
Cellulose depolymerization: In a mixed solvent of 1-ethyl-3-methylimidazole chloride and water, cellulose can be directly depolymerized to produce glucose with a yield of 70%, without the need for pretreatment (such as acid hydrolysis or enzymatic hydrolysis), significantly reducing production costs.
Technological breakthrough: Through the synergistic effect of solvents and catalysts, high-value utilization of biomass is achieved, providing a new path for the production of biofuels and bio based chemicals.
The application in the field of environment covers heavy metal pollution control, organic pollutant degradation, and waste gas treatment:
Heavy metal adsorption: The modified magnetic nanoparticles (Fe ∝ O ₄ @ C ₂ mimCl) have a maximum adsorption capacity of 150mg/g for Pb ² ⁺ and can be quickly separated under an external magnetic field, making them suitable for the treatment of heavy metal pollution in water bodies.
Organic pollutant extraction: Using ethylene glycol solution containing 1-ethyl-3-methylimidazole chloride as the extractant, the isopropanol water azeotrope is separated by extraction distillation. The purity of isopropanol reaches 99.5%, and the extractant can be recycled for more than 20 times.
Waste gas treatment: Preparation of photocatalytic filter membrane with TiO ₂ composite for the degradation of volatile organic compounds (VOCs). Experiments have shown that under visible light irradiation, the degradation rate of formaldehyde by the filter membrane reaches 90% and can operate stably for a long time.
Technical advantage: Selective adsorption or degradation of pollutants is achieved through molecular design, which combines high efficiency and environmental friendliness, and meets the requirements of sustainable development.
In the electronics industry, it is mainly used to prepare conductive materials, electrolytes, and semiconductor materials:
Lithium ion battery electrolyte: The electrolyte is prepared by compounding with LiPF ₆, which can suppress the corrosion of aluminum current collector and extend the battery life. The experiment showed that adding 5% 1-Ethyl-3-methylimidazolium chloride electrolyte increased the capacity retention rate of the battery from 75% to 88% after 500 cycles.
Fuel cell catalyst support: Its modified carbon nanotube (CNT) support can improve the dispersion of platinum nanoparticles (Pt NPs), resulting in an oxygen reduction reaction (ORR) mass activity of 0.35A/mg Pt in fuel cells, which is 2.5 times higher than commercial Pt/C catalysts.
Flexible electronic materials: Composite with polyurethane (PU) to prepare conductive elastomers, with a conductivity of 10 ⁻ S/cm and a tensile strength of 10MPa, suitable for electrode materials in wearable devices.
Technological breakthrough: Through the synergistic effect of ionic liquids and nanomaterials, the performance of electronic materials is significantly improved, promoting the development of flexible electronics, new energy and other fields.
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