Synthesis and thermophysical properties of ionic liquids: cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids

Kwan, Man-Lung; Mirjafari, Arsalan; McCabe, John R.; O’Brien, Richard A.; Essi, David F.; Baum, Leah; West, Kevin N.; Davis, James H.

doi:10.1016/j.tetlet.2012.09.101

Cited by 22 publications

(22 citation statements)

References 8 publications

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“…[6] The melting point depression was observed for both cis and trans double bonds, but the effect was more pronounced for cis unsaturations, presumably due to a greater decrease in packing efficiency when the "kinked" cis bond was present. Additional structural moieties, such as cyclopropyl rings added mid-chain, [12] were also observed to lower melting points relative to saturated n-alkyl chains and commercially available cationic lipids used for liposome formation and gene delivery were observed to collapse into ionic liquids when hydrophilic anions (Cl -, Br -) were replaced with bistriflimide. [13] Recently, we have shown that the inclusion of a sulfur atom, rather than an unsaturation, in the side chain (resulting in 1-thiaalkyl-3-methylimidazolium bistriflimide salts) produces similar melting point depression without the possibility of oxidative cleavage of double bonds.…”

Section: Introductionmentioning

confidence: 99%

Thermophysical and absorption properties of brominated vegetable oil

Thomas

Bramblett

Green

et al. 2015

Journal of Molecular Liquids

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Brominated vegetable oil (BVO) is a dense, bio-derived food additive used to emulsify citrus flavors in a variety of manufactured beverages. Although its high density is well known, accurate values for density and other properties, such as melting point, viscosity, refractive index and liquid phase heat capacity are not available in the literature. In this work, these properties are measured and correlated as a function of temperature from ~273K to ~353K. The volume expansivity, derived from the density, is also calculated. The density, viscosity and heat capacity are then compared with corresponding literature values for natural, unmodified oils. While the density and viscosity are markedly higher than the natural oils, the heat capacity is not significantly different. Through comparison with the viscosities of halogenated internal alkenes, it is shown that the increase in viscosity is likely due to enhanced dispersion forces, rather than enhanced polarity upon bromination. Additionally, the solubility of N2O and CO2 in brominated vegetable oil are measured at 310 K from 0.01 MPa to 2 MPa and, like unmodified olive oil, brominated vegetable oil exhibits higher N2O solubility than CO2 solubility. Such property trends are expected to be predictive of trends encountered when recently described lipidic ionic liquids are compared with their brominated analogues.

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Section: Introductionmentioning

confidence: 99%

Thermophysical and absorption properties of brominated vegetable oil

Thomas

Bramblett

Green

et al. 2015

Journal of Molecular Liquids

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“…In a third instance, cyclopropanated oleic acid methyl ester synthesized the reaction of the double bond of the oleate with diiodomethane, and diethylzinc was used to alkylate the tertiary amine. After reacting the obtained alkyl iodide with the imidazoles, anion exchange of the iodide with bistriflimide gave imidazolium bistriflimide ILs [108].…”

Section: Lipid-based Ionic Liquidsmentioning

confidence: 99%

Bio-Solvents: Synthesis, Industrial Production and Applications

Oklu¹,

Matsinha²,

Makhubela³

2020

Solvents, Ionic Liquids and Solvent Effects

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Solvents are at the heart of many research and industrial chemical processes and consumer product formulations, yet an overwhelming number are derived from fossils. This is despite societal and legislative push that more products be produced from carbon-neutral resources, so as to reduce our carbon footprint and environmental impact. Biomass is a promising renewable alternative resource for producing bio-solvents, and this review focuses on their extraction and synthesis on a laboratory and large scale. Starch, lignocellulose, plant oils, animal fats and proteins have been combined with creative synthetic pathways, novel technologies and processes to afford known or new bio-derived solvents including acids, alkanes, aromatics, ionic liquids (ILs), furans, esters, ethers, liquid polymers and deep eutectic solvents (DESs)-all with unique physiochemical properties that warrant their use as solvation agents in manufacturing, pharmaceutical, cosmetics, chemicals, energy, food and beverage industries, etc. Selected bio-solvents, conversion technologies and processes operating at commercial and demonstration scale including (1) Solvay's Augeo™ SL 191 renewable solvent, (2) Circa Group's Furacell™ technology and process for making levoglucosenone (LGO) to produce dihydrolevoglucosenone (marketed as Cyrene™), (3) Sappi's Xylex ® technology and demonstration scale processes that aim to manufacture precursors for biosolvents and (4) Anellotech's Bio-TCat™ technology and process for producing benzene, toluene and xylenes (BTX) are highlighted.

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“…After high temperature conditioning to 250 ºC, the resolution of the selected pairs of analytes decreased indicating that the MAOT for 10 was between 200 ºC and 250 ºC (see Figure S6). A final approach to improve the thermal stability of the lipidic IL involved the net addition of a methylene (CH 2 ) fragment to the double bond within the side chain to obtain an IL possessing a cyclopropanyl group in the side chain [32]. As shown in Figures S7 and S8, IL 11 exhibited a similar thermal stability to R1.…”

Section: Thermal Stability Of Lipidic Il Stationary Phasesmentioning

confidence: 99%

“…Recently, novel lipid-inspired ILs containing long alkyl side chains (≥ C 8 ) were reported [29][30][31][32]. By strategically incorporating various functional groups (i.e., double bonds, thioether branched chains, and cyclopropanyl groups), the melting point of the resulting ILs can be significantly reduced.…”

Section: Introductionmentioning

confidence: 99%

Lipidic ionic liquid stationary phases for the separation of aliphatic hydrocarbons by comprehensive two-dimensional gas chromatography

Zhang

O’Brien

et al. 2017

Journal of Chromatography A

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Lipidic ionic liquids (ILs) possessing long alkyl chains as well as low melting points have the potential to provide unique selectivity as well as wide operating ranges when used as stationary phases in gas chromatography. In this study, a total of eleven lipidic ILs containing various structural features (i.e., double bonds, linear thioether chains, and cyclopropanyl groups) were examined as stationary phases in comprehensive two dimensional gas chromatography (GC×GC) for the separation of nonpolar analytes in kerosene. N-alkyl-N'-methyl-imidazolium-based ILs containing different alkyl side chains were used as model structures to investigate the effects of alkyl moieties with different structural features on the selectivities and operating temperature ranges of the IL-based stationary phases. Compared to a homologous series of ILs containing saturated side chains, lipidic ILs exhibit improved selectivity toward the aliphatic hydrocarbons in kerosene. The palmitoleyl IL provided the highest selectivity compared to all other lipidic ILs as well as the commercial SUPELCOWAX 10 column. The linoleyl IL containing two double bonds within the alkyl side chain showed the lowest chromatographic selectivity. The lipidic IL possessing a cyclopropanyl group within the alkyl moiety exhibited the highest thermal stability. The Abraham solvation parameter model was used to evaluate the solvation properties of the lipidic ILs. This study provides the first comprehensive examination into the relation between lipidic IL structure and the resulting solvation characteristics. Furthermore, these results establish a basis for applying lipidic ILs as stationary phases for solute specific separations in GC×GC.

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Synthesis and thermophysical properties of ionic liquids: cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids

Cited by 22 publications

References 8 publications

Thermophysical and absorption properties of brominated vegetable oil

Thermophysical and absorption properties of brominated vegetable oil

Bio-Solvents: Synthesis, Industrial Production and Applications

Lipidic ionic liquid stationary phases for the separation of aliphatic hydrocarbons by comprehensive two-dimensional gas chromatography

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