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Continuous synthesis of peralkylated imidazoles and their transformation into ionic liquids with improved (electro)chemical stabilities

(2012) CHEMPHYSCHEM. 13(13). p.3146-3157
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Abstract
A versatile and efficient method to synthesize tetrasubstituted imidazoles via a one-pot modified DebusRadziszewski reaction and their subsequent transformation into the corresponding imidazolium ionic liquids is reported. The tetrasubstituted imidazoles were also synthesized by means of a continuous flow process. This straightforward synthetic procedure allows for a fast and selective synthesis of tetrasubstituted imidazoles on a large scale. The completely substituted imidazolium dicyanamide and bis(trifluoromethylsulfonyl)imide salts were obtained via a metathesis reaction of the imidazolium iodide salts. The melting points and viscosities are of the same order of magnitude as for their non-substituted analogues. In addition to the superior chemical stability of these novel ionic liquids, which allows them to be applied in strong alkaline media, the improved thermal and electrochemical stabilities of these compounds compared with conventional imidazolium ionic liquids is also demonstrated by thermogravimetrical analysis (TGA) and cyclic voltammetry (CV). Although increased substitution of the ionic liquids does not further increase thermal stability, a definite increase in cathodic stability is observable.
Keywords
aza heterocycles, alkaline stability, cyclic voltammetry, ionic liquids, sustainable chemistry, DICYANAMIDE ANION, ELECTROCHEMICAL APPLICATIONS, CATIONIC STRUCTURES, THERMAL-STABILITY, SALTS, ELECTROLYTES, CATALYSIS, SOLVENTS, BASE, ELECTRODEPOSITION

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Citation

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Chicago
Maton, Cédric, Nils De Vos, Bart Roman, Evert Vanecht, Neil R Brooks, Koen Binnemans, Stijn Schaltin, Jan Fransaer, and Christian Stevens. 2012. “Continuous Synthesis of Peralkylated Imidazoles and Their Transformation into Ionic Liquids with Improved (electro)chemical Stabilities.” Chemphyschem 13 (13): 3146–3157.
APA
Maton, C., De Vos, N., Roman, B., Vanecht, E., Brooks, N. R., Binnemans, K., Schaltin, S., et al. (2012). Continuous synthesis of peralkylated imidazoles and their transformation into ionic liquids with improved (electro)chemical stabilities. CHEMPHYSCHEM, 13(13), 3146–3157.
Vancouver
1.
Maton C, De Vos N, Roman B, Vanecht E, Brooks NR, Binnemans K, et al. Continuous synthesis of peralkylated imidazoles and their transformation into ionic liquids with improved (electro)chemical stabilities. CHEMPHYSCHEM. 2012;13(13):3146–57.
MLA
Maton, Cédric, Nils De Vos, Bart Roman, et al. “Continuous Synthesis of Peralkylated Imidazoles and Their Transformation into Ionic Liquids with Improved (electro)chemical Stabilities.” CHEMPHYSCHEM 13.13 (2012): 3146–3157. Print.
@article{3184235,
  abstract     = {A versatile and efficient method to synthesize tetrasubstituted imidazoles via a one-pot modified DebusRadziszewski reaction and their subsequent transformation into the corresponding imidazolium ionic liquids is reported. The tetrasubstituted imidazoles were also synthesized by means of a continuous flow process. This straightforward synthetic procedure allows for a fast and selective synthesis of tetrasubstituted imidazoles on a large scale. The completely substituted imidazolium dicyanamide and bis(trifluoromethylsulfonyl)imide salts were obtained via a metathesis reaction of the imidazolium iodide salts. The melting points and viscosities are of the same order of magnitude as for their non-substituted analogues. In addition to the superior chemical stability of these novel ionic liquids, which allows them to be applied in strong alkaline media, the improved thermal and electrochemical stabilities of these compounds compared with conventional imidazolium ionic liquids is also demonstrated by thermogravimetrical analysis (TGA) and cyclic voltammetry (CV). Although increased substitution of the ionic liquids does not further increase thermal stability, a definite increase in cathodic stability is observable.},
  author       = {Maton, C{\'e}dric and De Vos, Nils and Roman, Bart and Vanecht, Evert and Brooks, Neil R and Binnemans, Koen and Schaltin, Stijn and Fransaer, Jan and Stevens, Christian},
  issn         = {1439-4235},
  journal      = {CHEMPHYSCHEM},
  language     = {eng},
  number       = {13},
  pages        = {3146--3157},
  title        = {Continuous synthesis of peralkylated imidazoles and their transformation into ionic liquids with improved (electro)chemical stabilities},
  url          = {http://dx.doi.org/10.1002/cphc.201200343},
  volume       = {13},
  year         = {2012},
}

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