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1-butyl-3-methylimidazolium tetrafluoroborate (BMImBF4), a yellow transparent viscous liquid, molecular formula C8H15BF4N2, CAS 174501-65-6,can be used in ionic liquids, can be used in many reactions, such as hydrogenation or asymmetric hydrogenation, and has higher enantioselectivity compared with homogeneous phase; Suzuki cross-coupling reaction at room temperature. BMImBF4 is a transparent light yellow orange oily substance at room temperature and pressure, with certain hygroscopicity. BMIMBF4 is an imidazole type ionic liquid that is miscible with acetone, acetonitrile, ethyl acetate, isopropanol, and dichloromethane, but not with n-hexane, toluene, and water. This compound is commonly used as a solvent phase in organic chemical reactions and is often used for homogeneous catalytic organic chemical reactions.
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Chemical Formula |
C8H15BF4N2 |
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Exact Mass |
368 |
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Molecular Weight |
368 |
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m/z |
226 (100.0%), 225 (24.8%), 227 (8.7%), 226 (2.1%) |
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Elemental Analysis |
C, 42.51; H, 6.69; B, 4.78; F, 33.62; N, 12.39 |
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Melting point - 71 ° C, Density 1.21 g / ml at 20 ° C (lit.), Refractive index N20 / D 1.52, Flashpoint 288 ° C, Storage condition: store below + 30 ° C, Form: viscous liquid, Color clear yellow-orange, PH value 5 (H2O, 20 ℃), Miscible with acetone, acetonitrile, ethyl acetate, isopropyl alcohol and methyl chloride Immiscible with hexane, toluene, and water., Stability hygroscopic, InChIKeyYKVHBSVCYVBXQM-UHFFFAOYSA-M.
1-butyl-3-methylimidazolium tetrafluoroborate (CAS number: 174501-65-6) is an ionic liquid composed of 1-butyl-3-methylimidazolium cation ([BMIM] ⁺) and tetrafluoroborate anion ([BF ₄] ⁻), which appears as a transparent pale yellow to orange oily liquid at room temperature. Its unique physical and chemical properties, such as low vapor pressure, high thermal stability, wide liquid range, and excellent solubility, make it widely applicable in fields such as green chemistry, catalytic reactions, electrochemistry, and separation technology.
1. Asymmetric synthesis and chiral catalysis
Application mechanism: As a solvent or catalyst carrier, it can enhance enantioselectivity by regulating the reaction microenvironment (such as polarity, hydrogen bonding network). For example, in asymmetric hydrogenation reactions, its cations form ion pairs with transition metal catalysts (such as ruthenium and rhodium complexes), stabilizing chiral intermediates and increasing enantiomer excess (ee%) by 15% -20% compared to traditional organic solvents.
Case: When synthesizing multi substituted aryl isopropyl ether from bromoisopropanol and substituted phenol as raw materials, the ionic liquid used as a solvent can achieve a conversion rate of 98% of the raw materials, and the product is easy to separate by extraction. The recovery rate of the ionic liquid exceeds 95%, significantly reducing organic solvent pollution.
2. Suzuki cross coupling reaction
Room temperature catalytic advantage: In the presence of palladium catalyst, the activation energy of the reaction can be reduced, allowing the coupling reaction between arylboronic acid and halogenated aromatic hydrocarbons to be completed at 25 ℃ with a yield of 92% (traditional methods require 80 ℃). Its high polarity promotes the stability of ionic intermediates and reduces side reactions.
Industrial value: This reaction is a key step in the synthesis of biphenyl compounds (such as pharmaceutical intermediates and liquid crystal materials), and the use of ionic liquids can simplify the process flow and reduce energy consumption.
3. Biocatalysis and Enzymatic Reactions
Enzyme immobilization carrier: Lipases, oxidoreductases, etc. are immobilized on the surface of ionic liquids through physical adsorption or covalent bonding, forming recyclable biocatalysts. For example, in a supercritical carbon dioxide (ScCO ₂) biphasic system, the ionic liquid can maintain enzyme activity as an enzyme coating for over 100 hours, which is three times longer than in an aqueous system.
Product separation optimization: In ester synthesis reactions, ionic liquids and ScCO ₂ form a biphasic system, and the products are automatically extracted into the CO ₂ phase after the reaction, while enzymes are retained in the ionic liquid phase, achieving continuous production.
Electrochemical field: high-performance electrolytes and energy storage materials
1. Electrolyte for lithium-ion batteries
Wide electrochemical window: The electrochemical stability window of 1-butyl-3-methylimidazolium tetrafluoroborat reaches 4.5V (vs. Li ⁺/Li), which can be adapted to high-voltage positive electrode materials (such as nickel manganese cobalt ternary materials). Its ionic conductivity (about 8mS/cm at 25 ℃) is close to that of organic carbonate solvent system, but its volatility is reduced by 90%.
Modification of solid electrolyte: gel electrolyte prepared by compounding with polyvinylidene fluoride (PVDF) can increase the lithium ion migration number to 0.6 (about 0.4 for traditional liquid electrolyte), reduce concentration polarization and extend battery cycle life.
2. Supercapacitors
Enhancement of double-layer capacitance: As an electrolyte, its high dielectric constant (ε ≈ 11) enhances charge storage at the electrode/electrolyte interface, resulting in a specific capacitance of 120F/g for the activated carbon electrode (40% higher than that of aqueous electrolytes).
Wide temperature range application: Maintain liquid state within the range of -40 ℃ to 100 ℃, suitable for energy storage devices in extreme environments. For example, in the power system of an Arctic research station, the low-temperature performance of supercapacitors based on this ionic liquid is three times higher than that of traditional equipment.
Separation and Extraction Technology: Efficient and Environmentally Friendly Separation Media
1. Fuel oil desulfurization
Extraction mechanism: By utilizing the π - π interaction between [BF ₄] ⁻ and sulfur-containing compounds (such as dibenzothiophene) and the hydrophobicity of cations, selective extraction of sulfur components is achieved. The desulfurization rate of single-stage extraction at 60 ℃ reached 54.39%, and the removal rate after three-stage continuous extraction exceeded 80%.
Economy: Compared to traditional hydrogenation desulfurization processes, the operating temperature is reduced by 150 ℃, equipment investment is reduced by 30%, and there is no hydrogen consumption, making it suitable for small and medium-sized refineries.
2. Separation of metal ions
Complex extraction: After compounding with macrocyclic compounds such as crown ethers and calixarenes, it can selectively extract rare earth metals such as uranium and thorium. For example, in nuclear waste liquid treatment, the distribution ratio of UO ₂ ² ⁺ reaches 120, which is 5 times higher than the traditional tributyl phosphate system.
Regeneration cycle: Ionic liquid regeneration can be achieved through reverse extractants (such as dilute nitric acid), and the extraction efficiency only decreases by 8% after 10 cycles of use.
Materials Science: Functional Modification and Synthesis of New Materials
1. Polymer electrolyte membrane
Ionic conductivity enhancement: 1-butyl-3-methylimidazolium tetrafluoroborate is doped into a polyether sulfone (PES) or polybenzimidazole (PBI) matrix to prepare an all solid state polymer electrolyte. Its ion conductivity reaches 1.2 × 10 ⁻ S/cm at 80 ℃, meeting the requirements of fuel cells.
Mechanical performance optimization: By adjusting the ionic liquid content (5% -15%), the flexibility and mechanical strength of the membrane can be balanced, with a tensile strength of 45MPa, which is twice as high as pure polymers.
2. Synthesis of nanomaterials
Template guiding function: when synthesizing silica nanoparticles by sol-gel method, ionic liquid can control particle size (10-50nm) and pore size distribution (2-5nm) as a structure guiding agent. The electrostatic interaction between its cation and silicon hydroxyl group inhibits particle aggregation, with a specific surface area of 800m ²/g.
Stability of metal nanoparticles: As a reducing agent and stabilizer, platinum nanoparticles with uniform particle size (3-5nm) can be synthesized in one step, exhibiting high catalytic activity in methanol oxidation reaction (mass activity up to 0.5A/mg ₙₚ).
Other innovative applications
1. Gas adsorption and storage
CO ₂ capture: At 298K and 5bar, the absorption capacity of CO ₂ is 0.11mol/mol ILs, which is 30% higher than traditional amine solutions. Its regeneration energy consumption only requires heating at 50 ℃, which is 60% lower than the monoethanolamine method.
Hydrogen purification: By modifying ionic liquid anions (such as introducing fluorinated groups), impurities such as CO and CH can be selectively adsorbed, resulting in a hydrogen purity of 99.999%.
2. Photochemical regulation
Electron transfer rate regulation: In the benzoyl photochemical reaction, ionic liquids stabilize the triplet excited state, extending the triplet lifetime of tetraphenylporphyrin from 2.95 μ s to 184 μ s and increasing the photon yield by 5 times.
Fluorescent probe carrier: After being complexed with fluorescent dyes such as Rhodamine B, it can be used to detect heavy metal ions (such as Pb ² ⁺, Hg ² ⁺) in aqueous solutions, with a detection limit of ppb level.
1-Butyl-3-methylimidazolium tetrafluoroborate (BMIM BF4) is an ionic liquid with a wide range of applications.
1. Solvent:
BMIM BF4, as an ionic liquid solvent, can be used in various chemical processes such as dilution, catalytic reactions, and extraction. Due to its low volatility and high chemical stability, BMIM BF4 has the potential to replace traditional organic solvents.
2. Electrolyte:
BMIM BF4 can be used as an electrolyte in electrochemical and energy storage devices, such as lithium-ion batteries, supercapacitors, and fuel cells. As a component of the electrolyte, BMIM BF4 can provide good ion transport performance, improve the cycling stability and energy density of the battery.
3. Catalyst/reaction medium:
BMIM BF4 can be used as a catalyst or reaction medium to promote organic synthesis reactions. It can provide a favorable reaction environment, changing reaction rate, selectivity, or product distribution. BMIM BF4 can also form corresponding catalytic systems with metal complexes, participating in rare earth metal catalytic reactions, olefin polymerization, etc.
4. Extractant:
BMIM BF4 can be used for the extraction and separation process of organic and inorganic substances. It has high solubility and selectivity, and can form complexes or interact with target compounds for extraction, separation, or concentration of target components in samples.
5. Flame retardant:
BMIM BF4 has potential in the field of flame retardancy. Adding it as an additive to the polymer system can significantly improve the flame retardancy of the polymer, providing a lower combustion rate and higher flame retardancy index.
6. Lubricants:
BMIM BF4 can be used as a liquid based lubricant to improve friction and wear characteristics. Form a protective film on the surface of the friction pair to reduce surface contact and wear, and provide better lubrication effect.
7. Chemical analysis:
BMIM BF4 can be used as a standard compound, internal standard, or ionic liquid additive in techniques such as mass spectrometry and chromatography. It can provide stable reference points and background signals to help accurately determine and analyze target compounds.
8. Metal electrodeposition:
BMIM BF4 can be used as a component of the metal electrodeposition system for processes such as electroplating, electrolysis, and electrodeposition. It can provide more uniform metal deposition and improve the quality and performance of the coating.
9. BMIMBF4 is a type of room temperature ionic liquid. These compounds are salts composed of organic cations and inorganic or organic anions that are liquid at or near room temperature. They have many unique properties that molecular solvents cannot compare to, such as high boiling point, low vapor pressure, high density, and unique solubility. They are often used in organic synthetic chemistry to improve reaction yields and conversions.
We are the supplier of 1-Butyl-3-Methylimidazolium tetrafluoroborat (BMIMBF4).
Remark: BLOOM TECH(Since 2008), ACHIEVE CHEM-TECH is the subsidiary of us.
Synthetic BMIMBF4, BMIMBF4 as bulk solvent phase, provide new opportunities for recyclable alternatives to conventional organic solvents and can be used for biocatalysis to produce commercially important chemicals, including asymmetric synthesis, In some cases, the formation rate and enantioselectivity of the product were improved. 1chemicalbook-butyl-3-methylimidazole tetrafluoroborate has been used as an enzyme coating for the development of recyclable heterogeneous biocatalysts, as an immobilized carrier of enzymes in a two-phase system using SCCO2, and as a component of a supporting liquid membrane for the continuous separation of reactants and products in enzyme catalyzed reactions.
In a dry reactor, 1-methylimidazole and 1-chlorobutane were mixed in a molar ratio of 1:1.1, and the resulting reaction mixture was stirred at approximately 60 ° C for a reaction time of approximately 108 hours. Wash the obtained 1-butyl-3-methylimidazolium with ethyl acetate. In the second step, the above mixture was used, and 65 mL of HBF4 and a few mL of water were used to treat the 1-butyl-3-methylimidazolium obtained in the previous step to replace chloride ions with BF4 ions. The resulting reaction mixture was stirred overnight, and then the reactant was dissolved in dichloromethane. The reactant was washed with water, and finally evaporated under vacuum to obtain 1-butyl-3-methylimidazolium tetrafluoroborate as the target product molecule.
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