Preparation of Novel Room-Temperature Molten Salts by Neutralization of Amines

Hirao, Michiko; Sugimoto, Hiromi; Ohno, Hiroyuki

doi:10.1149/1.1394036

Cited by 214 publications

(123 citation statements)

References 20 publications

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“…The synthesis of the protic ILs can follow two different routes, the first of which consists in the neutralization of an aqueous solution of the starting amine with a suitable acid [26]; the second method is carried out under solvent-free conditions, by directly mixing the reagents and heating the mixture above the components' melting points in argon atmosphere [20].…”

Section: Protic Ilsmentioning

confidence: 99%

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Potentialities of ionic liquids as new electrolyte media in advanced electrochemical devices

Fernicola

Scrosati

Ohno

2006

Ionics

240

156

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This paper reviews the various classes of ionic liquids (ILs) in view of their established and expected applications in advanced electrochemical devices, such as lithium batteries, fuel cells, and supercapacitors. In this respect, particular attention is devoted to aprotic and protic ILs, with a related discussion in terms of their thermal and transport properties. In addition, the role in the electrochemical technology of a new class of ILs having cation and anion tethered in an intramolecular form is stressed. Due to their emerging importance, IL-based polymers are finally reported and discussed. A conclusion, where the expected evolution of the ILs research and development is evaluated, is also included.

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Section: Protic Ilsmentioning

confidence: 99%

“…The effect of the cation structure has been studied by Hirao et al [26]. By neutralizing a series of tertiary amines, e.g., pyrroline, indole, pyrazole, and pyrrolidine derivatives, with tetrafluoroboric acid, several RTILs have been obtained.…”

Section: Protic Ilsmentioning

confidence: 99%

Potentialities of ionic liquids as new electrolyte media in advanced electrochemical devices

Fernicola

Scrosati

Ohno

2006

Ionics

240

156

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“…Since "ILs" became attractive as synthetic media, many protic ILs have been reported, particularly by Ohno and co-workers. [13][14][15] To provide ILs that were unequivocally ionic, Ohno and co-workers used proton transfer from a very powerful acid, hydrogen bis-trimethylsulfonyl imide, HTFSI, the conjugate base of which is an anion that is well known for promoting low melting points. In a more recent study, our own group has explored the relationship between this protontransfer process and the nature of the acid transferring the proton.…”

Section: Introductionmentioning

confidence: 99%

Protic Ionic Liquids: Preparation, Characterization, and Proton Free Energy Level Representation

2007

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We give a perspective on the relations between inorganic and organic cation ionic liquids (ILs), including members with melting points that overlap around the borderline 100°C. We then present data on the synthesis and properties (melting, boiling, glass temperatures, etc.) of a large number of an intermediate group of liquids that cover the ground between equimolar molecular mixtures and ILs, depending on the energetics of transfer of a proton from one member of the pair to the other. These proton-transfer ILs have interesting properties, including the ability to serve as electrolytes in solvent-free fuel cell systems. We provide a basis for assessing their relation to aprotic ILs by means of a Gurney-type proton-transfer free energy level diagram, with approximate values of the energy levels based on free energy of formation and pK a data. The energy level scheme allows us to verify the relation between solvent-free acidic and basic electrolytes, and the familiar aqueous variety, and to identify neutral protic electrolytes that are unavailable in the case of aqueous systems.

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“…[2][3][4] In contrast to organic systems which are either scarce or environmentally unfriendly, ionic liquids (ILs) have emerged as a relatively new class of non-aqueous electrolytes for energy storage applications. [5][6][7][8][9] ILs are salts that are liquid below 100…”

mentioning

confidence: 99%

Investigation of Ammonium- and Phosphonium-Based Deep Eutectic Solvents as Electrolytes for a Non-Aqueous All-Vanadium Redox Cell

Bahadori

Hashim

Manan

et al. 2016

J. Electrochem. Soc.

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The charge/discharge characteristics for vanadium acetylacetonate in deep eutectic solvents were evaluated using an H-cell with an anion-exchange membrane separator for the first time. Coulombic (CE) and energy efficiencies (EE) of the electrolyte containing V(acac) 3 /0.5 M TEABF 4 in DES3 (a hydrogen bonded eutectic between choline chloride and ethylene glycol) were obtained as 49-52% and 25-31%, respectively, when charging from 0 to 50% of theoretical maximum state-of-charge for 12 cycles. The low CE may be due to the crossover of the active species through the separator, or to the loss of active vanadium due to a parasitic reaction. However, the CE was similar to that for acetonitrile (CH 3 CN) indicating the promise of DESs as suitable electrolytes for future evaluation. Charge and discharge voltages are respectively higher and lower than the formal cell potential obtained by voltammetry. Ohmic drop in the DES results from the low conductivity of the electrolyte and the relatively large distance between the two electrodes in the H-cell. Further studies require investigation in a flow cell with analyses of polarization curves and impedance to determine the loss mechanisms in sufficient detail. Low energy density is often reported as a barrier in the commercialization of redox flow batteries using current aqueous electrolytes. Non-aqueous electrolytic solvents offer a wide potential window of operation and increase the energy capacity of the system.2-4 In contrast to organic systems which are either scarce or environmentally unfriendly, ionic liquids (ILs) have emerged as a relatively new class of non-aqueous electrolytes for energy storage applications. [5][6][7][8][9] ILs are salts that are liquid below 100• C. ILs have many favorable characteristics, e.g., low volatility, high intrinsic conductivity, large electrochemical window, etc. In addition, ILs can be tuned by combining different cations and anions. However, many reports point out the hazardous toxicity and the poor biodegradability of most ILs.7 ILs with high purity are also required since impurities, even in trace amounts, affect their physical properties. Additionally, their synthesis is not entirely environmentally friendly since it generally requires a large amount of salts and solvents in order to completely exchange the anions.10 These drawbacks together with the high price of common ILs unfortunately hamper their industrial applications. Such issues may be overcome by using deep eutectic solvents (DESs). 11,12A DES is a eutectic mixture of an organic salt (ammonium or phosphonium) and a hydrogen bond donor (HBD), that is made up of different components such as amides, metallic salts, alcohols, carboxylic acids and amines that may be used as complexing agents (typically an H-bond donor).13,14 DESs have a melting point that is far below that of either individual constituent. The mechanism is that the complexing agent interacts with the anion and increases its effective size. This, in turn, decreases the anionic interaction with the cation ther...

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Preparation of Novel Room-Temperature Molten Salts by Neutralization of Amines

Cited by 214 publications

References 20 publications

Potentialities of ionic liquids as new electrolyte media in advanced electrochemical devices

Potentialities of ionic liquids as new electrolyte media in advanced electrochemical devices

Protic Ionic Liquids: Preparation, Characterization, and Proton Free Energy Level Representation

Investigation of Ammonium- and Phosphonium-Based Deep Eutectic Solvents as Electrolytes for a Non-Aqueous All-Vanadium Redox Cell

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