862999-80-2Relevant articles and documents
Rate Constants for Reaction of 1,2-Dimethylimidazole with Benzyl Bromide in Ionic Liquids and Organic Solvents
Skrzypczak,Neta
, p. 253 - 258 (2004)
The rate constant for the Menschutkin reaction of 1,2-dimethylimidazole with benzyl bromide to produce 3-benzyl-1,2-dimethylimidazolium bromide was determined in a number of ionic liquids and molecular organic solvents. The rate constants in 12 ionic liquids are in the range of (1.0-3.2) × 10 -3 L mol-1 s-1 and vary with the solvent anion in the order (CF3SO2)2N- 6- 4-. Variations with the solvent cation (butylmethylimidazolium, octylmethylimidazolium, butyldimethylimidazolium, octyldimethylimidazolium, butylmethylpyrrolidinium, and hexyltributylammonium) are minimal. The rate constants in the ionic liquids are comparable to those in polar aprotic molecular solvents (acetonitrile, propylene carbonate) but much higher than those in weakly polar organic solvents and in alcohols. Correlation of the rate constants with the solvatochromic parameter ET(30) is reasonable within each group of similar solvents but very poor when all the solvents are correlated together, Better correlation is obtained for the organic solvents by using a combination of two parameters, π* (dipolarity/polarizibility) and α (hydrogen bond acidity), while additional parameters such as δ (cohesive energy density) do not provide any further improvement.
Alkali stability excellent imidazole and imidazolium cation
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Paragraph 0243-0244; 0296-0298, (2018/04/13)
and membranes and devices comprising the polymers. Also provided are methods of making the inventive compounds and polymers.
Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure-Stability Relationships
Hugar, Kristina M.,Kostalik, Henry A.,Coates, Geoffrey W.
supporting information, p. 8730 - 8737 (2015/07/27)
Highly base-stable cationic moieties are a critical component of anion exchange membranes (AEMs) in alkaline fuel cells (AFCs); however, the commonly employed organic cations have limited alkaline stability. To address this problem, we synthesized and characterized the stability of a series of imidazolium cations in 1, 2, or 5 M KOH/CD3OH at 80 °C, systematically evaluating the impact of substitution on chemical stability. The substituent identity at each position of the imidazolium ring has a dramatic effect on the overall cation stability. We report imidazolium cations that have the highest alkaline stabilities reported to date, >99% cation remaining after 30 days in 5 M KOH/CD3OH at 80 °C.