Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System

Nokami, Toshiki; Matsumoto, Kuninobu; Itoh, Takaaki; Fukaya, Yukinobu; Itoh, Toshiyuki

doi:10.1021/op500131u

Cited by 12 publications

(7 citation statements)

References 25 publications

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“…NMR spectra were recorded using a 5 mm probe on a Varian Inova 400 spectrometer. Spectroscopic data of ILs 1 , 2 , 3 , and 4 were in accordance with the literature. , …”

Section: Methodssupporting

confidence: 86%

Pyrrolidinium-based Ionic Liquids: Aquatic Ecotoxicity, Biodegradability, and Algal Subinhibitory Stimulation

Samorì

Campisi

Fagnoni

et al. 2015

ACS Sustainable Chem. Eng.

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Pyrrolidinium imides are considered among the most promising electrolytes for the development of novel and sustainable portable energy devices. Because of this widespread potentiality, a risk scenario of an erroneous disposal of ionic liquids-based batteries in the environment has to be taken into account. In the present study some of the best energy performing pyrrolidinium-based ionic liquids were evaluated in terms of persistence in aquatic environments and hazard towards freshwater organisms (the crustacean Daphnia magna and the unicellular green alga Raphidocelis subcapitata). The examined ionic liquids were not aerobically biodegradable (biodegradation less than 5% in 28 days) but they demonstrated low toxicity towards algae and crustaceans, according to the standard bioassay endpoints (EC 50 > 100 mg L -1 ). However, ionic liquids were able to alter the cellular morphology of R. subcapitata and an increased amount of proteins (30%) was observed in the exposed cells, suggesting an inhibition of cellular division. rpm for 10 min, washed with a physiological saline solution and then centrifuged again; this procedure was repeated 3 times in order to assure the removal of any eventual IL trace on algal surfaces. Then algal cells were freeze-dried and analyzed to determine their nitrogen (by elemental analysis), protein (by the Lowry protocol 27 ) and lipid (by GC-MS) content. Ammonium (NH 3 -N, mg L -1 ) was measured at day 0 and after 72 h in the filtrate through test kit colorimetric analyses (DR/2010; Hach, Colorado, USA), by using the Nessler Method. 33Algae were also exposed to a concentration of 0.9 mM of 2 under the dark and using 2 as the sole N-source in the growth medium (OECD medium prepared with all nutrients besides NH 4 Cl).Controls were run in parallel in each experiment.The biovolume determination was performed in accordance to the literature 25 : 20 cells were randomly selected and the sizes (length and width) were measured. Elemental analyses were performed by using an elemental analyzer (Thermo Scientific, Flash 2000, Organic Elemental Analyzer) by means of the flash combustion technique. The fatty acid methyl esters (FAMEs) content of algal cells (indicator of the lipid amount) was determined as follows: samples (about 2 mg) were suspended in dimethyl carbonate (0.4 mL).2,2-Dimethoxypropane (0.1 mL) and 0.5 M NaOH in MeOH (0.1 mL) were then added; the samples were placed in an incubator at 90°C for 30 min. After cooling for 5 min to room temperature, 1.3 M BF 3 -methanol 10% (w/w) reagent (0.7 mL) was added before repeating the incubation for 30 min. After cooling for 5 min to room temperature, saturated NaCl aqueous solution (2 mL) and hexane (1 mL) containing methyl nonadecanoate (internal standard for GC-MS quantification, 0.02 mg) were added and the samples were centrifuged at 4000 rpm for 1 min. The upper hexane-dimethylcarbonate layer, containing FAMEs, was transferred to vials for GC-MS analysis. Each analysis was repeated in duplicate. The relative response factors used for the quant...

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“…NMR spectra were recorded using a 5 mm probe on a Varian Inova 400 spectrometer. Spectroscopic data of ILs 1 , 2 , 3 , and 4 were in accordance with the literature. , …”

Section: Methodssupporting

confidence: 86%

Pyrrolidinium-based Ionic Liquids: Aquatic Ecotoxicity, Biodegradability, and Algal Subinhibitory Stimulation

Samorì

Campisi

Fagnoni

et al. 2015

ACS Sustainable Chem. Eng.

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“…To the best of our knowledge, although the preparation and a part of physicochemical properties of Pyr 1,6 TFSA and Pyr 1,1O2O1 TFSA have been reported, [34,35] those of Pyr 1,1O4 TFSA and Pyr 1,4O1 TFSA have not. The physicochemical properties of these four RTILs were therefore evaluated under an inert atmosphere.…”

Section: Resultsmentioning

confidence: 89%

Ether‐Functionalized Pyrrolidinium‐Based Room Temperature Ionic Liquids: Physicochemical Properties, Molecular Dynamics, and the Lithium Ion Coordination Environment

et al. 2021

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The physicochemical properties of room temperature ionic liquids (RTILs) consisting of bis(trifluoromethanesulfonyl)amide (TFSA−) combined with 1‐hexyl‐1‐methylpyrrolidinium (Pyr1,6+), 1‐(butoxymethyl)‐1‐methylpyrrolidinium (Pyr1,1O4+), 1‐(4‐methoxybutyl)‐1‐methyl pyrrolidinium (Pyr1,4O1+), and 1‐((2‐methoxyethoxy)methyl)‐1‐methylpyrrolidinium (Pyr1,1O2O1+) were investigated using both experimental and computational approaches. Pyr1,1O2O1TFSA, which contains two ether oxygen atoms, showed the lowest viscosity, and the relationship between its physicochemical properties and the position and number of the ether oxygen atoms was discussed by a careful comparison with Pyr1,1O4TFSA and Pyr1,4O1TFSA. Ab initio calculations revealed the conformational flexibility of the side chain containing the ether oxygen atoms. In addition, molecular dynamics (MD) calculations suggested that the ion distributions have a significant impact on the transport properties. Furthermore, the coordination environments of the Li ions in the RTILs were evaluated using Raman spectroscopy, which was supported by MD calculations using 1000 ion pairs. The presented results will be valuable for the design of functionalized RTILs for various applications.

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“…Two kinds of ionic liquids used in this study were synthesized by an organic method as previously reported, 35 and are shown in Fig. 1.…”

Section: Preparation Of Electrolytes and Electrodesmentioning

confidence: 99%

Functional ionic liquids for enhancement of Li-ion transfer: the effect of cation structure on the charge–discharge performance of the Li₄Ti₅O₁₂electrode

Shimizu

Usui

2016

Phys. Chem. Chem. Phys.

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As the development of high energy-density Li-ion batteries moves ahead, ensuring safety of the batteries has become increasingly important. Among the unique physicochemical properties of ionic liquids, thermal stability can be one of the answers to the challenge. The use of ionic liquids, however, causes critical issues concerning the kinetics of Li-ion transfer at the electrode-electrolyte interface. In the present study, ionic liquids consisting of 1-((2-methoxyethoxy)methyl)-1-methylpiperidinium (PP1MEM) or 1-hexyl-1-methylpiperidinium (PP16) and bis(trifluoromethanesulfonyl)amide (TFSA) were applied to an electrolyte for Li-ion batteries, and we investigated the effect of cation structure on interfacial Li-ion transfer using Li4Ti5O12 as a model electrode by means of Raman spectroscopy and electrochemical impedance spectroscopy. It was found that the ether functional group in the PP1MEM cation has the meaningful function; the cation structure reduces the electrostatic interaction between the Li ion and TFSA anions in an ionic liquid electrolyte. The solvation number of the TFSA anion per Li ion consequently became smaller than that in PP16-TFSA, and the lower solvation number in PP1MEM-TFSA allowed the facile Li-ion diffusion in the electrolyte bulk rather than the interfacial Li-ion transfer and significantly improved the rate performance. The results offer the prospect of utilization of PP1MEM-TFSA as an electrolyte solvent. The knowledge obtained from this study contributes to the development of next-generation Li-ion batteries having both high energy density and high safety.

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Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System

Cited by 12 publications

References 25 publications

Pyrrolidinium-based Ionic Liquids: Aquatic Ecotoxicity, Biodegradability, and Algal Subinhibitory Stimulation

Pyrrolidinium-based Ionic Liquids: Aquatic Ecotoxicity, Biodegradability, and Algal Subinhibitory Stimulation

Ether‐Functionalized Pyrrolidinium‐Based Room Temperature Ionic Liquids: Physicochemical Properties, Molecular Dynamics, and the Lithium Ion Coordination Environment

Functional ionic liquids for enhancement of Li-ion transfer: the effect of cation structure on the charge–discharge performance of the Li₄Ti₅O₁₂electrode

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Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System

Cited by 12 publications

References 25 publications

Pyrrolidinium-based Ionic Liquids: Aquatic Ecotoxicity, Biodegradability, and Algal Subinhibitory Stimulation

Pyrrolidinium-based Ionic Liquids: Aquatic Ecotoxicity, Biodegradability, and Algal Subinhibitory Stimulation

Ether‐Functionalized Pyrrolidinium‐Based Room Temperature Ionic Liquids: Physicochemical Properties, Molecular Dynamics, and the Lithium Ion Coordination Environment

Functional ionic liquids for enhancement of Li-ion transfer: the effect of cation structure on the charge–discharge performance of the Li4Ti5O12electrode

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Product

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Functional ionic liquids for enhancement of Li-ion transfer: the effect of cation structure on the charge–discharge performance of the Li₄Ti₅O₁₂electrode