171058-21-2

Basic information

• Product Name: 1-TETRADECYL-3-METHYLIMIDAZOLIUM CHLORIDE
• Synonyms: 1-TETRADECYL-3-METHYLIMIDAZOLIUM CHLORIDE;3-METHYL-1-TETRADECYLIMIDAZOLIUM CHLORIDE;1-Tetradecy-3-methyllimidazolium chloride;1-Tetradecyl-3-methylimidazolium chloride,98%;1-Teradecyl-3-methyimidazolium Chloride;[C14MIm]Cl
• CAS NO: 171058-21-2
• Molecular Formula: C18H35ClN2
• Molecular Weight: 314.94
• Mol File: 171058-21-2.mol

Chemical Properties

• Melting Point: 51-52 °C
• Appearance: /
• CAS DataBase Reference: 1-TETRADECYL-3-METHYLIMIDAZOLIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-TETRADECYL-3-METHYLIMIDAZOLIUM CHLORIDE(171058-21-2)
• EPA Substance Registry System: 1-TETRADECYL-3-METHYLIMIDAZOLIUM CHLORIDE(171058-21-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 171058-21-2(Hazardous Substances Data)

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 2425-54-9 myristyl chloride 

Downstream Products

• 404001-49-6 1-tetradecyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide 

Relevant articles and documents

Binding interactions of anesthetic drug with surface active ionic liquid

The application of aggregation behavior of a surface active ionic liquids (SAILs), 1-dodecyl-3-methylimidazolium chloride [C12mim][Cl] and 1-tetradecyl-3-methylimidazolium chloride [C14mim][Cl] in drug delivery of lidocaine hydrochloride has been investigated from surface tension and fluorescence measurements at 298.15?K and from conductance at 288.15, 298.15 and 308.15?K. Critical aggregation concentration (CAC), degree of ionization (α), and various thermodynamic parameters like Gibbs free energy of aggregation (??Gagg.°) standard enthalpy of aggregation (??Hagg.°)?and standard entropy of aggregation (??Sagg.°) are calculated using conductivity measurements. The surface activity of the ILs in various mixed solvents are examined from surface tension measurements by calculating various surface parameters like maximum surface excess concentration (Гmax), minimum surface area per ionic liquid molecule (Amin), adsorption efficiency (pC20), effectiveness of surface tension reduction (Πcac) surface tension at CAC (γcac), p (packing parameter), and CAC at different compositions. Fluorescence measurements have been employed to get detailed insight of the local microenvironment of the aggregates, and critical aggregation concentration (CAC). Decrease in the CAC values was observed with the increase in the amount of drug which is attributed to the balancing between electrostatic and hydrophobic interactions. This shows that the spontaneity of aggregation process of IL increases with the increase in the concentration of drug.

Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts

For the purpose of developing new disinfectants and antiseptics, we searched for compounds having high bactericidal activity against gram-positive bacteria, gram-negative bacteria, and fungi. Three different series of quaternary imidazolium and pyrrolidinonium salts were synthesized: series A (1-alkyl-3-methylimidazolium chlorides and bromides); series B (1-alkyl-2-methyl-3-hydroxyethylimidazolium chlorides); and series C (N-alkyl-N-hydroxyethylpyrrolidinonium). Series B and C were newly designed. These three series were tested to evaluate their antibacterial and antifungal properties for the first time. Seven microbial strains were used in the study: Escherichia coli KCTC1924, Salmonella typhimurium KCTC1926, Staphylococcus aureus 209 KCTC1916, Staphylococcus aureus R209 KCTC1928, Bacillus subtilis KCTC1914, Candida albicans KCTC1940, and Chlorella regularis. The antimicrobial efficiency was measured by bacterial and fungal growth inhibition expressed as minimal inhibitory concentration (MIC) values. Series A and B imidazolium salts had very good antimicrobial activity against the examined Gram-negative bacteria, Gram-positive bacteria, and fungi. Also the pyrrolidinonium salt was found to have low MIC for some of tested microorganisms. The antibacterial and antifungal active properties of the salts depend upon the structure of functional groups and the alkyl chain length in the imidazolium and pyrrolidinonium ring. Among the synthesized quaternary imidazolium and pyrrolidinonium salts, the imidazolium salts containing a long alkyl chain and the introduction of a hydroxyethyl chain and methyl group into the imidazolium ring structure leads to broad spectrum active antimicrobial agents which not only have bacteriostatic properties but could be powerful bactericides.

Physicochemical Properties of Long Chain Alkylated Imidazolium Based Chloride and Bis(trifluoromethanesulfonyl)imide Ionic Liquids

In this research synthesis, purification and characterization of six long-chain imidazolium based ionic liquids (ILs) including C10, C12, and C14 alkyl chain with chloride and NTf2 anions was investigated. All of these studied ILs were characterized using NMR, CHNSO, and DSC, and some impurities such as water, chloride, and metal contents were reported. The temperature dependence of some physicochemical properties such as density, dynamic and kinematic viscosity, refractive index, surface tension, and thermal stability of the synthesized ILs were also studied in the range 283.15 to 363.15 K, and the results were compared with those from the literature. Moreover, using the measured data, the thermal expansion coefficient and molar polarizability of the ILs were calculated. On the other hand the effects of alkyl chain length and anion were explained. The results revealed that although the refractive indices and viscosities increased as alkyl chain length increased, the density and surface tension results were reciprocally decreased. Besides, the results suggest that the synthesized ILs were the best choice as fuel additives.

Interactions Between Surface Active Ionic Liquid and Procaine Hydrochloride Drug in Aqueous Solution

Complex formation between the anesthetic drug, procaine hydrochloride and a surface active ionic liquid (SAIL), 1-tetradecyl-3-methylimidazolium chloride, [C14mim][Cl], in aqueous medium has been investigated using surface tension, fluorescence and DLS measurements at 298.15?K and conductance at 288.15, 298.15 and 308.15?K. Critical aggregation concentration (CAC), degree of ionization (α), and various thermodynamic parameters were determined using the conductivity measurements. The interfacial behavior of SAIL at different concentrations of the drug was evaluated from surface tension measurements by calculating a series of surface parameters and CAC values. Fluorescence spectroscopy was used to evaluate the binding constant (K) and the standard state Gibbs energy change (ΔG°) for the formation of drug–SAIL complexes, which confirms the existence of cation–π interactions between the drug molecules and imidazolium ring of the SAIL molecules. The CAC values were found to decrease with increase in the concentration of the drug, which is due to the balancing between hydrophobic and electrostatic interactions. Dynamic light scattering provides sufficient information about the size of the aggregates and the variation in the hydrodynamic diameters pertaining to the changes in the drug concentration. The results from above methods show that the aggregation process of SAIL is favored by increases in the concentration of the drug. It is demonstrated that with the better understanding of the interactions, [C14mim][Cl] can be judiciously utilized in making use of procaine hydrochloride.

Effects of alkyl chain length on properties of 1-alkyl-3-methylimidazolium fluorohydrogenate ionic liquid crystals

A series of 1-alkyl-3-methylimidazolium fluorohydrogenate salts (C xMIm(FH)2F, x=8, 10, 12, 14, 16, and 18) have been characterized by thermal analysis, polarized optical microscopy, IR spectroscopy, X-ray diffraction, and anisotropic ionic conductivity measurements. Liquid crystalline mesophases with a smectic A interdigitated bilayer structure are observed from C10 to C18, showing a fan-like or focal conic texture. The temperature range of the mesophase increases with the increase in the alkyl chain length (from 10.1°C for C10MIm(FH)2F to 123.1°C for C18MIm(FH) 2F). The distance between the two layers in the smectic structure gradually increases with increasing alkyl chain length and decreases with increasing temperature. Conductivity parallel to the smectic layers is around 10mS-cm?1 regardless of the alkyl chain length, whereas that perpendicular to the smectic layers decreases with increasing alkyl chain length because of the thicker insulating sheet with the longer alkyl chain.

Adsorption behavior of long alkyl chain imidazolium ionic liquids at the n-butyl acetate + water interface

The adsorption behavior of amphiphilic long alkyl chain imidazolium ionic liquids (ILs), 1-alkyl-3-methylimidazolium chloride {[Cnmim][Cl], n = 12, 14, 16} at the interface of n-butyl acetate + water system was studied. Within IL bulk concentration range of 1.00 · 10- 5-1.00 · 10- 2 mol/dm3 and temperature of 293.2-318.2 K, the used ILs act as excellent surfactants and reduce the interfacial tension significantly. The corresponding interfacial activity appeared logically in the order of [C16mim][Cl] > [C14mim][Cl] > [C12mim][Cl]. An almost linear decrease in interfacial tension was also relevant by temperature. For modeling, the Szyszkowski adsorption equation was used to reproduce the experimental data. The consistent fittings confirm the ideal adsorption of the used IL molecules at the interface. Results also show that adsorption effectiveness increases with the alkyl chain length; however, it declines with temperature. On the other hand, adsorption tendency increases with alkyl chain length as well as with temperature. Negative standard free energy values indicate simultaneous adsorption for all cases.

Synthesis and characterization of eight hydrophilic imidazolium-based ionic liquids and their application on enhanced oil recovery

In order to difficulties in producing large amount of crude oil and remaining oil by primary and secondary oil recovery processes, enhanced oil recovery (EOR) techniques have been developed. Water injection is one of the EOR methods which has shown great potential in recent years. The water flooding process is more effective when the injected water is enriched by chemicals which improve the oil recovery by reducing interfacial tension (IFT) and alternating wettability. In this work eight long alkyl chain imidazolium based ionic liquids (ILs) including Octyl, Decyl, Dodecyl and Tetradecyl methylimidazolium and two different anions namely Chlorid and trihydrogen diphosphate (THDP), were synthesized and characterized by 1HNMR and elemental analysis. As a nobility it should be noted that ILs containing THDP anion have not been synthesized yet and they were used in upstream oil industry for the first time. Furthermore, some physicochemical properties were investigated for studied ILs as a function of temperature. The synthesized ILs were examined as additives in injected water to reduce the IFT in water flooding process. The critical micelle concentration (CMC) point and IFT of enriched sea water by ILs/crude oil, were measured as a function of ILs concentration. The results showed that ILs can be good candidates for EOR technology due to their significant behavior in IFT reduction and their low consumption. The consumed concentrations for ILs were observed at ppm levels, so they are favorable choices when economic concerns are considered. According to obtained results, as the alkyl chain was longer, the CMC point and IFT values were lower. Moreover the investigation of IFT values, revealed that ILs containing THDP anion were more efficient in IFT reduction compared with ILs including chloride anion. [C14mim][Cl] and [C14mim][THDP] were the most effective ILs which 50 and 25 ppm of these ILs, reduced the IFT values to 0.65 ± 0.04 and 0.5 ± 0.02, respectively.

Multifunctional amphiphilic ionic liquid pathway to create water-based magnetic fluids and magnetically-driven mesoporous silica

Amphiphilic ionic liquids, 1-alkyl-3-methylimidazolium chloride (CnmimCl with n = 10, 12, 14, 16) were firstly used as modifiers to construct a self-assembly bilayer on the surface of iron oxide nanoparticles for generation of highly stable, water-based magnetic fluids. Subsequently, a magnet-driven mesoporous silica was synthesized by in situ self-assembly in the bilayer CnmimCl-stabilized magnetic fluid using the C16mimCl as template and tetraethylorthosilicate (TEOS) as silicon source via a hydrothermal synthesis and following calcination procedure. A systematic study was carried out addressing the influence of the alkyl chain length of CnmimCl in the primary and secondary layers on the stability of magnetic fluids. The characterization of TEM, XRD, VSM, electrophoresis experiments, TGA and DTA showed that stable water-based magnetic fluids can be synthesized based on the assembly of the well-defined bilayer-CnmimCl structure with long-chain C16mimCl as secondary layer on the magnetite (Fe3O4) nanoparticles. The results of small and wide-angle XRD, TEM, VSM, and N2 absorption experiments indicated that the nano-scale magnetic Fe3O4 particles were inlayed into hexagonal p6mm mesoporous silica (MCM-41 type) framework. Importantly, it was found that the obtained Fe3O4/MCM-41 was an appropriate adsorbent for the adsorption of rhodamine B and methylene blue from their aqueous solution. In addition, the adsorbent could be separated and reclaimed fleetly from the solution under external magnetic field.

Long Chain Alkylated Ionic Liquids as Pour Point Depressant and Rheology Improver for Crude Oil

Abstract: Cold flow properties of Iranian crude oil have been investigated by twodifferent imidazolium ionic liquids including 1-dodecyl-3-methylimidazoliumreduce the pour point up to bis(trifluoromethanesulfonyl) imide([C12min](NTf2]) and1-tetradecyl-3-methylimidazolium bis(trifluoromethanesulfonyl) imide([C14min](NTf2]).([C14min](NTf2]) showed highability to 12°C optimal performance by addition of 2000 ppm. Wax crystallizationbehaviour of untreated and treated crude oil was monitored using differentialscanning calorimetry (DSC) and the polarized optical microscopy (POM). Resultsfrom DSC and POM revealed that the presence of both ILs changes the process ofcrystallization and extends wax precipitation time. Furthermore, rheologicalbehaviour of the crude oil was improved and viscosity was decreased by 73% at23.5°C and 87% at 15°C by addition of[C14mim][NTf2].

Nanoreactors stable up to 200 °c: A class of high temperature microemulsions composed solely of ionic liquids

It is a challenge to develop microemulsions which can serve as nanoreactors for the synthesis of nanoparticles and chemical reactions at high temperature. In this work, a class of novel high temperature microemulsions consisting solely of ionic liquids have been designed and prepared for the first time. It is found that nanoscale droplets formed in the ionic liquid microemulsions can be maintained up to 200 °C, and the size distribution of the droplets can be easily tuned by selection of the ionic liquids and varying compositions of the systems. By using such microemulsions as nanoreactors, porous metals such as Pt have been prepared at 180 °C without using any purposely added reductant.