Science China Chemistry

, Volume 55, Issue 8, pp 1638–1647 | Cite as

Properties of alkylbenzimidazoles for CO2 and SO2 capture and comparisons to ionic liquids

  • Matthew S. Shannon
  • Michelle S. Hindman
  • Scott. P. O. Danielsen
  • Jason M. Tedstone
  • Ricky D. Gilmore
  • Jason E. Bara
Articles Special Issue · Ionic Liquid and Green Chemistry
First Online:
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Accepted:

Abstract

To date, few reports have been concerned with the physical properties of the liquid phases of imidazoles and benzimidazoles-potential starting materials for a great number of ionic liquids. Prior research has indicated that alkylimidazole solvents exhibit different, and potentially advantageous physical properties, when compared to corresponding imidazolium-based ionic liquids. Given that even the most fundamental physical properties of alkylimidazole solvents have only recently been reported, there is still a lack of data for other relevant imidazole derivatives, including benzimidazoles. In this work, we have synthesized a series of eight 1-n-alkylbenzimidazoles, with chain lengths ranging from ethyl to dodecyl, all of which exist as neat liquids at ambient temperature. Their densities and viscosities have been determined as functions of both temperature and molecular weight. Alkylbenzimidazoles have been found to exhibit viscosities that are more similar to imidazolium-based ILs than alkylimidazoles, owed to a large contribution to viscosity from the presence of a fused ring system. Solubilities of CO2 and SO2, two species of concern in the emission of coal-fired power generation, were determined for selected alkylbenzimidazoles to understand what effects a fused ring system might have on gas solubility. For both gases, alkylbenzimidazoles were determined to experience physical, non-chemically reactive, interactions. The solubility of CO2 in alkylbenzimidazoles is 10%–30% less than observed for corresponding ILs and alkylimidazoles. 1-butylbenzimidazole was found to readily absorb at least 0.333 gram SO2 per gram at low pressure and ambient temperature, which could be readily desorbed under an N2 flush, a behavior more similar to imidazolium-based ILs than alkylimidazoles. Thus, we find that as solvents for gas separations, benzimidazoles share characteristics with both ILs and alkylimidazoles.

Keywords

benzimidazole imidazole ionic liquids carbon dioxide (CO2) capture sulfur dioxide (SO2) 
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Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2012

Authors and Affiliations

  • Matthew S. Shannon
    • 1
  • Michelle S. Hindman
    • 1
  • Scott. P. O. Danielsen
    • 2
    • 3
  • Jason M. Tedstone
    • 2
    • 4
  • Ricky D. Gilmore
    • 1
  • Jason E. Bara
    • 1
  1. 1.Department of Chemical & Biological EngineeringUniversity of AlabamaTuscaloosaUSA
  2. 2.NSF-REU Site: Engineering Solutions for Clean Energy Generation, Storage and Consumption, Department of Chemical & Biological EngineeringUniversity of AlabamaTuscaloosaUSA
  3. 3.Department of Chemical & Biomolecular EngineeringUniversity of PennsylvaniaPhiladelphiaUSA
  4. 4.Department of Chemical & Biomolecular EngineeringClemson UniversityClemsonUSA

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