2534-66-9

Usage

Uses

Used in Chemical Reactions and Processes:
1-octylpyridinium bromide is used as a phase transfer catalyst for facilitating the transfer of materials between different phases, which is crucial in various chemical reactions and processes.
Used in Pharmaceutical and Personal Care Products:
1-octylpyridinium bromide is used as an antimicrobial and antifungal agent, contributing to the preservation and efficacy of pharmaceutical and personal care products.
Used in Metal Extraction and Separation:
1-octylpyridinium bromide is used as an extracting agent for the separation of metals from aqueous solutions, enhancing the efficiency of metal recovery processes.
Used in Industrial and Environmental Applications:
1-octylpyridinium bromide is used in the development of novel materials for various industrial and environmental applications, leveraging its versatile properties to create innovative solutions.

InChI:InChI=1/C13H22N.BrH/c1-2-3-4-5-6-8-11-14-12-9-7-10-13-14;/h7,9-10,12-13H,2-6,8,11H2,1H3;1H/q+1;/p-1

Upstream product

• 110-86-1 pyridine 
• 111-83-1 1-bromo-octane 

Downstream Products

• 384347-06-2 1-octylpyridinium bis(trifluoromethylsulfonyl)imide 

Relevant academic research and scientific papers

Physicochemical properties of hydrophobic ionic liquids containing 1-octylpyridinium, 1-octyl-2-methylpyridinium, or 1-octyl-4-methylpyridinium cations

This paper reports the synthesis of some ionic liquids containing cations 1-octylpyridinium [OPYR]+, 1-octyl-2-methylpyridinium [2MOPYR] +, or 1-octyl-4-metnylpyridinium [4MOPYR]+ and anions dicyanamide [N(CN)2]-, bis(trifluoromethylsulfonyl)imide [Tf2N]-, bis(pentafluoroethylsulfonyl)imide [BETI] -, trifluoromethyl sulfonate [TfO]-, nonafluorobutyl sulfonate [NfO]-, tetrafluoroborate [BF4]-, trifluorophenylborate [BF3PH]-, tetraphenylborate [BPh4] or hexafluoroarsenate [AsF6]-. Melting points, decomposition temperatures, densities, mutual solubilities with water, and viscosities have been measured. Unlike similar ionic liquids containing imidazolium cations, pyridinium ionic liquids studied here are nearly immiscible with water. Viscosities are similar, and water contents are slightly lower than those for ionic liquids containing imidazolium cations.

Octanol/water partition coefficients of pyridinium-based ionic liquids

Nine pyridinium-based ionic liquids were synthesised, which include 1-butylpyridinium bromide ([BPYR] [Br]), 1-hexylpyridinium bromide ([HPYR][Br]), 1-octylpyridinium bromide ([OPYR][Br]), 1-hexylpyridinium bis(trifluoromethylsulfonyl)imide ([HPYR] [NTf2]), 1-octylpyridinium bis(trifluoromethylsulfonyl)imide ([OPYR][NTf2]), 1-hexylpyridinium trifluoromethanesulfonate ([HPYR] [TFO]), 1-octylpyridinium trifluoromethanesulfonate ([OPYR][TFO]), 1-hexylpyridinium tetrafluoroborate ([HPYR] [BF4]), 1-octylpyridinium I tetrafluoroborate ([OPYR][BF4]). The octanol/water partition coefficients (KOWs) of these pyridinium-based ionic liquids were determined by shake-flask method. It is found that the pyridinium-based ionic liquids measured in this work are extremely hydrophilic except for [OPYR] [NTf2]. It is also found that KOWs of [NTf2] ionic liquids were dependent on the concentration and high ionic liquids concentration in water leads to big KOW.

Micelle formation as a factor influencing the mode(s) of metal ion partitioning into: N -alkylpyridinium-based ionic liquids (ILs): Implications for the design of IL-based extraction systems

Prior studies of metal ion partitioning between an acidic aqueous phase and an ionic liquid in the presence of a macrocyclic polyether have demonstrated that the overall partitioning is a composite of three distinct pathways: neutral complex/ion-pair extraction, exchange of a cationic metal-crown ether (CE) complex for the cationic constituent of the IL, and exchange of the metal ion for a hydronium ion in a CE-H3O+ complex formed during acid preconditioning of the IL. The obvious undesirability of the ion-exchange pathways, which can lead to substantial loss of the IL cation to the aqueous phase, has led to efforts to identify means by which these processes can be suppressed or eliminated. Prior work with N,N′-dialkylimidazolium and quaternary ammonium bis [(trifluoromethyl)sulfonyl]imides has shown that increasing the hydrophobicity of the IL cation can be an effective means of diminishing the contribution of ion-exchange. Work with the corresponding N-alkylpyridinium ILs, however, indicates that in certain instances, an increase in the hydrophobicity of the IL cation is accompanied by a marked increase in its propensity to self-associate, leading to the formation of micelles in the aqueous phase. The net effect is to diminish or even negate the expected beneficial effect of IL cation hydrophobicity in reducing the contribution of ion exchange to the overall metal ion partitioning process, adversely impacting the "greenness" of extraction processes employing these ILs.

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

We studied the ultrafast dynamics of 40 aromatic cation based ionic liquids (ILs) by means of femtosecond Ramaninduced Kerr effect spectroscopy. The low-frequency Kerr spectra (ca. 0.3700 cm1) of the ILs were obtained from the Kerr transients by Fourier-Transform deconvolution analysis. The low-frequency Kerr spectra in the frequency range less than 200 cm-1 coming mainly from the intermolecular vibrations for the ILs were discussed in terms of (i) anion dependence, (ii) imidazolium cations vs. pyridinium cations, (iii) alkyl group dependence, and (iv) effect of methylation in aromatic cations. Several liquid properties, such as density, viscosity, electrical conductivity, and surface tension, of the present sample ILs at 293K were also estimated in this study. We clarified that the aromatic cation based ILs show a different relation of the first moment of the low-frequency spectral band to the bulk liquid parameter, which is the square root of surface tension divided by liquid density, from aprotic molecular liquids. The slope of the first moment to the bulk parameter for the aromatic cation based ILs is gentler than that for aprotic molecular liquids.

Thermochemistry of the pyridinium- and pyrrolidinium-based ionic liquids

We applied DSC for the determination of enthalpies of synthesis reactions of pyridinium- and pyrrolidinium-based ionic liquids (ILs) from pyridine (or N-methyl-pyrrolidine) and n-alkyl bromides (with n = 4, 5, 6, 7, and 8). The combination of reaction enthalpy measurements by DSC with modern high-level first-principles calculations opens valuable indirect thermochemical options to obtain values of enthalpies of the formation and vaporization enthalpies of ILs.

Does alkyl chain length really matter? Structure-property relationships in thermochemistry of ionic liquids

DSC was used for determination of reaction enthalpies of synthesis of ionic liquids [Cnmim][Cl]. A combination of DSC with quantum chemical calculations presents an indirect way to study thermodynamics of ionic liquids. The indirect procedure for vaporization enthalpy was validated with the direct experimental measurements by using thermogravimetry. First-principles calculations of the enthalpy of formation in the gaseous phase have been performed for the ionic species using the CBS-QB3 and G3 (MP2) theory. Experimental DSC data for homologous series of alkyl substituted imidazolium, pyridinium, and pyrrolidinium based ionic liquids with anions [Cl] and [Br] were collected from the literature. We have shown that enthalpies of formation, enthalpies of vaporization, and lattice potential energies are linearly dependant on the alkyl chain length. The thermochemical properties of ILs generally obey the group additivity rules and the values of the additivity parameters for enthalpies of formation and vaporization seem to be very close to those for molecular compounds.

Three different types of heterocycle of nitrogen-containing alkaline ionic liquids treatment of acid oil to remove naphthenic acids

Ionic liquids had enormous potential for industrial use as environmental friendly chemicals. A green and effective deacidification method was found based on ionic liquids. N-alkylpyridinium bromide ([APy]Br), 1-alkyl-3- methylimidazolium bromide ([AMIm]Br) and 1-alkyl-3-methylimidazolium imidazolide ([AMIm]Im) were used to remove naphthenic acids from acid oil. The performance of deacidification followed the order [APy]Br [AMIm]Br [AMIm]Im. The stronger alkalinity of ionic liquids was, the higher deacidification would be. The growth of alkyl chain length was also beneficial to get high deacidification. The deacidification mechanism was that liquid clathrate could form due to interaction between the ionic liquids and π-bond in naphthenic acids through π-π interaction. When the reagent/oil ratio of [OMIm]Im (1-octyl-3-methylimidazolium imidazolide)/oil was 0.008, the deacidification rate could be reached 100%. The preliminary results reveal that the process consumes less energy, saves time and produces less pollution to environment.

Scalable synthesis of ionic liquids: Comparison of performances of microstructured and stirred batch reactors

A range of alkylpyridinium bromide ionic liquids have been synthesized in a stirred reactor at multigram scale and characterized by physical methods (viscosity, conductivity, melting point, electrochemical window, and water content). One ionic liquid, octylpyridinium bromide, was chosen to be synthesized in both macro and reduced scale reactors, in order to compare its performance and to afford evidence of the advantages of a cross channel micro reactor (channel width = 1 mm) compared to a stirred reactor.

Parallel microwave-assisted synthesis of ionic liquids and screening for denitrogenation of straight-run diesel feed by liquid-liquid extraction

Fifty-six ionic liquids were efficiently synthesized in parallel format under one-pot, solvent-free microwaveassisted synthesis. These compounds were evaluated as extracting agents of nitrogen-containing compounds from a real Diesel feed before being submitted to the hydrodesulfurization process to obtain ultralow sulfur Diesel. Our results showed that halogenated ionic liquids are an excellent alternative due to these ionic liquids are relatively inexpensive, presenting a high selectivity for the extraction of nitrogen-containing compounds and can be regenerated and recycled.

H2O2/NaHCO3-mediated enantioselective epoxidation of olefins in NTf2-based ionic liquids and under ultrasound

The bicarbonate-activated peroxide (BAP) system has been shown to constitute an excellent and versatile combination for the epoxidation of olefins. Herein, we demonstrate that the benign H2O 2/NaHCO3 oxidative combination can be used for the enantioselective epoxidation of olefins using a chiral manganese porphyrin as a catalyst. This unprecedented result was made possible by the use of an ionic liquid with ultrasound, which leads to the activation of Mn-porphyrin catalysis.