Synthesis and Characterization of 5‐Cyanotetrazolide‐Based Ionic Liquids

Bergholz, Timm; Oelkers, Benjamin; Huber, Benedikt; Roling, Bernhard

doi:10.1002/chem.201405264

Cited by 4 publications

(37 citation statements)

References 64 publications

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“…[139] According to the TGA, cyclic voltammetry, viscosimetry,a nd impedance spectroscopy data, the prepared 1-butyl-1-methylpyrrolidinium 5-cyanotetrazolide [Bmpyrr] [C 2 N 5 ]h ad ah igh thermal stability( up to 230 8C), widee lectrochemicalw indow (4.5 V), moderate viscosity (25 mPa s À1 at 20 8C), reasonablei onic conductivity (5.4 mS cm À1 at 20 8C), and could be recommended as ap romising electrolyte for lithiumion batteries. [139] According to the TGA, cyclic voltammetry, viscosimetry,a nd impedance spectroscopy data, the prepared 1-butyl-1-methylpyrrolidinium 5-cyanotetrazolide [Bmpyrr] [C 2 N 5 ]h ad ah igh thermal stability( up to 230 8C), widee lectrochemicalw indow (4.5 V), moderate viscosity (25 mPa s À1 at 20 8C), reasonablei onic conductivity (5.4 mS cm À1 at 20 8C), and could be recommended as ap romising electrolyte for lithiumion batteries.…”

Section: Hypergolic Ilsmentioning

confidence: 99%

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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A global increase in environmental pollution demands the development of new "cleaner" chemical processes. Among urgent improvements, the replacement of traditional hydrocarbon-derived toxic organic solvents with neoteric solvents less harmful for the environment is one of the most vital issues. As a result of the favorable combination of their unique properties, ionic liquids (ILs), dense gases, and supercritical fluids (SCFs) have gained considerable attention as suitable green chemistry media for the preparation and modification of important chemical compounds and materials. In particular, they have a significant potential in a specific and very important area of research associated with the manufacture and processing of high-energy materials (HEMs). These large-scale manufacturing processes, in which hazardous chemicals and extreme conditions are used, produce a huge amount of hard-to-dispose-of waste. Furthermore, they are risky to staff, and any improvements that would reduce the fire and explosion risks of the corresponding processes are highly desirable. In this Review, useful applications of almost nonflammable ILs, dense gases, and SCFs (first of all, CO ) for nitration and other reactions used for manufacturing HEMs are considered. Recent advances in the field of energetic (oxygen-balanced and hypergolic) ILs are summarized. Significant attention is paid to the SCF-based micronization techniques, which improve the energetic performance of HEMs through an efficient control of the morphology and particle size distribution of the HEM fine particles, and to useful applications of SCFs in HEM processing that makes them less hazardous.

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Section: Hypergolic Ilsmentioning

confidence: 99%

Prospective Symbiosis of Green Chemistry and Energetic Materials

et al. 2017

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“…Recently, Bergholz, et al. investigated the electrochemical properties of a series of 5‐cyanotetrazolate salts for such a purpose, and demonstrated electrochemical properties suitable for application as a Li‐ion battery electrolyte. In this same work, electrochemical windows and conductivities of a set of 5‐cyanotetrazolate ILs were determined .…”

Section: Applications Of Azolate Ilsmentioning

confidence: 99%

“…investigated the electrochemical properties of a series of 5‐cyanotetrazolate salts for such a purpose, and demonstrated electrochemical properties suitable for application as a Li‐ion battery electrolyte. In this same work, electrochemical windows and conductivities of a set of 5‐cyanotetrazolate ILs were determined . Conductivities of all salts were appreciably high, with the 1‐ethyl‐3‐methylimidazolium 5‐cyanoimidazolate ([C 2 mim][5‐CN‐im]) salt in particular exhibiting a conductivity of 15×10 −3 S cm −1 at 30 °C, exceeding that of the more commonly used IL electrolyte, 1‐ethyl‐3‐methylimidazolium tris(perfluoroethyl)trifluorophosphate ([C 2 mim][FAP], 6.3×10 −3 S cm −1 ) measured in the same study.…”

Section: Applications Of Azolate Ilsmentioning

confidence: 99%

“…Other interionic interactions can be visualized clearly through these SCXRD analyses, with factors such as anion p-stacking observedf or triethylammonium 5-cyanotetrazole ([HN 2,2,2 ][5-CN-tet]), whereby the in-ring carbon atom sits 3.383 from the centero faneighboring anionic heterocycle. [39] Analysis of nitro-substituted azolates revealed the nitro groups can exist in either planar or non-planar configurations depending on the position of substitution at the azole ring, as shown in Figure 1. When in ap lanar configuration, the nitro groups contribute substantiallyt ot he resonance features of the anion, thus decreasing the melting point with the increasedd elocalization of charge.…”

Section: Structural Observationsmentioning

confidence: 99%

“…[5] The lithium salt of 5-cyanotetrazolate, when substituted with an electron-deficient Rg roup, had been proposed previously for use in Li-ion batteries, [66] with the anion's weakly coordinating and fluoride-free nature considered advantageous to more common IL anions such as [PF 6 ] À ,w hich can hydrolyzet of orm HF. [17] Recently,B ergholz, et al investigated the electrochemical properties of as eries of 5-cyanotetrazolate salts for such ap urpose, [39] and demonstrated electrochemical properties suitable for application as aL i-ion battery electrolyte. In this same work, electrochemical windows and conductivities of as et of 5-cyanotetrazolate ILs were determined.…”

Section: Applications Of Azolate Ilsmentioning

confidence: 99%

See 2 more Smart Citations

Azolate Anions in Ionic Liquids: Promising and Under‐Utilized Components of the Ionic Liquid Toolbox

Easton

Choudhary

Rogers

2018

Chemistry A European J

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Owing to their ease of synthesis, diffuse positive charge, and chemical stability, 1-alkyl-3-methylimidazolium cations (i.e., [C mim] ) are one of the most routinely utilized and historically important components in ionic liquid (IL) chemistry. However, while this is a routinely encountered member of the IL family as cations, relatively few workers have explored the versatile chemistry of azoles to allow their use as an anionic component in ILs, as azolates. Azolate anions possess many of the desired properties for IL formation, including a diffuse ionic charge, tailorable asymmetry, and synthetic flexibility, with the added advantages of not relying on halogen atoms for electron-withdrawing effects, as is commonly encountered with IL anions such as hexafluorophosphate. This review explores the 122 azolate-containing ILs known in the literature (prepared from only 39 disparate azolate anions), with a view to highlighting not only their demonstrated utility as an IL component, but the ways in which the larger scientific community may utilize their advantageous properties for new tailored materials.

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Pathways in the Degradation of Geminal Diazides

Holzschneider¹,

Häring²,

Haack³

et al. 2017

J. Org. Chem.

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The degradation of geminal diazides is described. We show that diazido acetates are converted into tetrazoles through the treatment with bases. The reaction of dichloro ketones with azide anions provides acyl azides, through in situ formation of diazido ketones. We present experimental and theoretical evidence that both fragmentations may involve the generation of acyl cyanide intermediates. The controlled degradation of terminal alkynes into amides (by loss of one carbon) or ureas (by loss of two carbons) is also shown.

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Synthesis and Characterization of 5‐Cyanotetrazolide‐Based Ionic Liquids

Cited by 4 publications

References 64 publications

Prospective Symbiosis of Green Chemistry and Energetic Materials

Prospective Symbiosis of Green Chemistry and Energetic Materials

Azolate Anions in Ionic Liquids: Promising and Under‐Utilized Components of the Ionic Liquid Toolbox

Pathways in the Degradation of Geminal Diazides

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