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Chemical Properties

White to light yellow crystalline powder

InChI:InChI=1/C10H22N.BrH/c1-3-4-8-11(2)9-6-5-7-10-11;/h3-10H2,1-2H3;1H/q+1;/p-1

Upstream product

• 626-67-5 N-methylcyclohexylamine 
• 109-65-9 1-bromo-butane 
• 120-94-5 1-Methylpyrrolidine 
• 998-40-3 tributylphosphine 
• 4945-48-6 1-butyl-piperidine 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 1357500-93-6 1-butyl-1-methylpiperidinium trifluoromethanesulfonate 
• 1257647-66-7 1-butyl-1-methylpiperidinium hexafluorophosphate 

Relevant academic research and scientific papers

Synthesis and performance of piperidinium-based ionic liquids as catalyst for alkylation of p-xylene with 1-hexadecene

Piperidinium-based ionic liquids (ILs) were synthesized under mild conditions by coordinating N-alkyl-N-methylpiperidinium bromide ([Pip1,x]Br) with anhydrous AlCl3. The weak basicity of N-methylpiperidine had little impact on downstream problems from proton impurities and catalyst poisoning. The results of Fourier transform infrared (FT-IR), electrospray ionization mass spectrometry (ESI-MS), and nuclear magnetic resonance (27Al NMR) confirmed that the active components in [Pip1,x]Br-2AlCl3 (χ = 0.67) were [Al3Cl9Br]? and [Al2Cl6Br]?. Besides, the reaction performance of [Pip1,8]Br-2AlCl3 under different conditions was carried out by single-factor experiment and further confirmed by orthogonal experimental method. Among these reaction conditions, the optimal combination was the reaction temperature of 40°C, ILs/O molar ratio of 0.2:1, px/O molar ratio of 12:1, and the reaction time of 30 min. Furthermore, [Pip1,8]Br-2AlCl3 had excellent stability and can be recycled 14 times. It was the high-efficiency catalytic activity and prominent recyclability that made continuous industrial production possible.

Free carbonate-based molecules in the electrolyte leading to severe safety concerns of Ni-rich Li-ion batteries

The safety of Li-ion batteries is one of the most important factors, if not the most, determining their practical applications. We have found that free carbonate-based solvent molecules in the hybrid electrolyte system can cause severe safety concerns. Mixing ionic liquids with a carbonate-based solvent as the co-solvent at a fixed salt concentration of 1 M LiPF6 can lead to free carbonate-based molecules causing poor charge storage performance and safety concerns.

Newly designed flow reactor as an original method of synthesis of ionic liquids by ion-exchange reactions

Optimization of chemical reactions is often costly and requires a significant investment in both materials and time. The solution to this type of difficulty may be the use of continuous flow systems. With the use of the newly designed continuous flow system, the method of synthesizing ionic liquids (ILs) by ion exchange was optimized. The flow rate of the substrates and the selection of the packing of the column in which the reactions were carried out (random packing or a chemical compound in the form of a solid, which was the source of the anion exchanged) were also optimized. The purity of the obtained ionic liquids and the progress of the reaction was determined using ion chromatography. Additionally, for the ionic liquids, which were the starting compounds for the ion exchange reaction, the basic physicochemical properties were determined, thus extending the data library available for chemical compounds belonging to the group of ionic liquids.

Chemical Vapor Deposition of Ionic Liquids for the Fabrication of Ionogel Films and Patterns

Film deposition and high-resolution patterning of ionic liquids (ILs) remain a challenge, despite a broad range of applications that would benefit from this type of processing. Here, we demonstrate for the first time the chemical vapor deposition (CVD) of ILs. The IL-CVD method is based on the formation of a non-volatile IL through the reaction of two vaporized precursors. Ionogel micropatterns can be easily obtained via the combination of IL-CVD and standard photolithography, and the resulting microdrop arrays can be used as microreactors. The IL-CVD approach will facilitate leveraging the properties of ILs in a range of applications and microfabricated devices.

Ultrafast dynamics in nonaromatic cation based ionic liquids: A femtosecond raman-induced kerr effect spectroscopic study

Herein, the data of the intermolecular vibrations of forty nonaromatic cation based ionic liquids (ILs) at 293 K measured by femtosecond Raman-induced Kerr effect spectroscopy are reported. The low-frequency spectra in the frequency range of 0.3700 cm11 were obtained by Fourier transform deconvolution analysis. The line shapes of the low-frequency spectra below 3200 cm11 were discussed on the basis of the ion species. The spectral intensity in nonaromatic cation based ILs was much lower than that in aromatic cation based ILs owing to the absence of the aromatic ring, i.e., the libration of the aromatic species had a strong spectral intensity in the low-frequency region. However, nonaromatic cation based ILs with a flat anion, such as dicyanamide and tricyanomethanide, showed stronger spectral intensity because of the libration of the anion. Other unique spectral features were also discussed in the context of the structure of the ion species. Liquid properties, such as density, viscosity, electrical conductivity, and surface tension, were also estimated. On comparing the low-frequency spectra with the bulk liquid properties of the nonaromatic cation based ILs, a mild linear relationship between the first moment of the low-frequency spectrum and a bulk parameter comprised of surface tension and density was observed.

Synthesis of task-specific imidazolium ionic liquid as an efficient catalyst in acetylation of alcohols, phenols, and amines

Herein, we report the synthesis of task-specific amino-functionalized imidazolium ionic liquid, acetate1-(2-tert-butoxycarbonylamino-ethyl)-3-methyl-3H-imidazol-1-ium; (Boc-NH-EMIM.OAc), as an efficient catalyst for the acetylation of alcohols, phenols, and amines in the presence of acetic anhydride (acetylating reagent). Remarkably, acetic anhydride in the presence of 10?molpercent of catalyst (Boc-NH-EMIM.OAc) under solvent-free conditions showed excellent acetylation activity in shorter duration of time. On the basis of this, a general procedure for acetylation of alcohols, phenols, and amines has been developed. The ionic liquid (Boc-NH-EMIM.OAc) can be readily recovered and reused successfully up to four consecutive cycles without any significant loss of its catalytic activity. We have been able to show that this acetylating method has many advantages. It gives high yields, takes shorter time, and develops the possibility of benign environmental-friendly process.

Oxidative Thioesterification of Alkenes Mediated by 1,3-Dibromo-5,5-dimethylhydantoin and DMSO for the Synthesis of α-Ketothioesters

A simple and mild approach for the synthesis of α-ketothioesters via 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α-ketothioesters products were produced in moderate to good y

Physicochemical and thermodynamic properties of the {1-alkyl-1-methylpiperidinium bromide [C1Cn =2,4PIP][Br], or 1-butylpyridinium bromide, [C4Py][Br], or tri(ethyl)butylammonium bromide [N2,2,2,4] [Br] + water} binary systems

This work is a continuation of our comprehensive study of ionic liquids, ILs (including organic salts with melting temperature above 100 °C) and their aqueous solutions as a novel alternative working pair for the absorption heat pump. A series of organic salts: 1-ethyl-1-methyl-piperidinium bromide, [C1C2PIP][Br], 1-butyl-1-methyl-piperidinium bromide, [C1C4PIP][Br], 1-butylpyridinium bromide, [C4Py][Br] and tri(ethyl)butylammonium bromide, [N2,2,2,4][Br] have been synthesized. The structures of compounds have been confirmed using NMR spectra. The basic thermal characterization of pure organic salts, including temperature and enthalpy of phase transition (Ttr, ΔtrH), temperature and enthalpy of melting (Tfus ΔfusH) have been measured using a differential scanning microcalorimetry technique (DSC). The physico-chemical properties that are: density (ρ) and dynamic viscosity (η) of the tested binary systems have been determined at wide temperature and composition range. From experimental densities data, the apparent molar volumes (V?,1) were calculated. In order to obtain limiting apparent molar volumes (V?,1 0), the concentration dependence of apparent molar volumes was correlated with Redlich–Mayer type equation. Additionally, the limiting molar expansibilities (E? 0) and isobaric thermal expansion coefficients (αP) have been calculated. Temperature dependence of the dynamic viscosity has been correlated using VFT equation. The solid?liquid phase equilibria (SLE) have been determined using a dynamic method and correlated using NRTL equation. The influence of the alkyl chain length in the piperidinium cation substituent, as well as the cation structure, on investigated properties are presented and discussed.

Rational selection of the cation of an ionic liquid to control the reaction outcome of a substitution reaction

A range of ionic liquids was examined as solvents for a substitution reaction. They were chosen through rationally varying the ionic liquid cation in order to enhance the rate constant. Access to charge and electron-withdrawing substituents benefitted rat

Effect of cation structure on the oxygen solubility and diffusivity in a range of bis{(trifluoromethyl)sulfonyl}imide anion based ionic liquids for lithium-air battery electrolytes

This paper reports on the solubility and diffusivity of dissolved oxygen in a series of ionic liquids (ILs) based on the bis{(trifluoromethyl)sulfonyl}imide anion with a range of related alkyl and ether functionalised cyclic alkylammonium cations. Cyclic voltammetry has been used to observe the reduction of oxygen in ILs at a microdisk electrode and chronoamperometric measurements have then been applied to simultaneously determine both the concentration and the diffusion coefficient of oxygen in different ILs. The viscosity of the ILs and the calculated molar volume and free volume are also reported. It is found that, within this class of ILs, the oxygen diffusivity generally increases with decreasing viscosity of the neat IL. An inverse relationship between oxygen solubility and IL free volume is reported for the two IL families implying that oxygen is not simply occupying the available empty space. In addition, it is reported that the introduction of an ether-group into the IL cation structure promotes the diffusivity of dissolved oxygen but reduces the solubility of the gas.