Hostname: page-component-586b7cd67f-t7czq Total loading time: 0 Render date: 2024-11-22T08:42:27.701Z Has data issue: false hasContentIssue false
  • English
  • Français

Microwave-assisted Synthesis of 1-(perfluorohexyl)-3-methylimidazolium iodide

Published online by Cambridge University Press:  27 December 2019

James E. Knoop Open the ORCID record for James E. Knoop [Opens in a new window]  and
Jeffrey R. Alston Open the ORCID record for Jeffrey R. Alston [Opens in a new window]
James E. Knoop
Affiliation:
Joint School of Nanoscience and Nanoengineering, North Carolina Agricultural and Technical State University, Greensboro, NC, 27401, USA
Jeffrey R. Alston*
Affiliation:
Joint School of Nanoscience and Nanoengineering, North Carolina Agricultural and Technical State University, Greensboro, NC, 27401, USA
*
(Email: [email protected])
Get access

Abstract

A perfluorinated ionic liquid, 1-(perfluorohexyl)-3-methylimidazolium iodide, was synthesized via microwave reaction and compared to a non-fluorinated analog. Typically, the synthesis of fluorinated ionic liquids involves long reaction times and multiple steps. We have demonstrated a shortened synthesis and a more straightforward procedure, by using a microwave reactor for the microwave-assisted synthesis of 1-(perfluorohexyl)-3-methylimidazolium iodide. The addition of fluorinated alkyl chains on imidazolium ionic liquid cations increases the molecular free volume of the ionic liquid which is beneficial for increasing CO2 physisorption. Computational and experimental data shows an increased CO2 solubility and capacity for fluorinated ionic liquids. The perfluoroalkyl functionalized ionic liquid is characterized using 1H and 19F NMR spectroscopy, FTIR spectroscopy, and DSC. By DSC, a crystallization onset is near -31 °C and while the onset of the melting point between -30 and -17 °C.

Keywords

microwave heatingsustainabilitychemical synthesisnuclear magnetic resonance (NMR)carbon dioxide
Type
Articles
Information
MRS Advances , Volume 5 , Issue 27-28: Energy & Environment , 2020 , pp. 1449 - 1456
Check for updates
Copyright
Copyright © Materials Research Society 2019

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Blanchard, L.A., Hancu, D., Beckman, E.J. and Brennecke, J.F.: Green processing using ionic liquids and CO2. Nature 399, 28 (1999).CrossRefGoogle Scholar
Almantariotis, D., Pensado, A.S., Gunaratne, H.Q., Hardacre, C., Padua, A.A., Coxam, J.Y. and Costa Gomes, M.F.: Influence of Fluorination on the Solubilities of Carbon Dioxide, Ethane, and Nitrogen in 1-n-Fluoro-alkyl-3-methylimidazolium Bis(n-fluoroalkylsulfonyl)amide Ionic Liquids. J Phys Chem B 121, 426 (2017).CrossRefGoogle ScholarPubMed
Zeng, S., Zhang, X., Bai, L., Zhang, X., Wang, H., Wang, J., Bao, D., Li, M., Liu, X. and Zhang, S.: Ionic-Liquid-Based CO2 Capture Systems: Structure, Interaction and Process. Chemical Reviews 117, 9625 (2017).10.1021/acs.chemrev.7b00072CrossRefGoogle ScholarPubMed
Lei, Z., Dai, C. and Chen, B.: Gas solubility in ionic liquids. Chem Rev 114, 1289 (2014).CrossRefGoogle ScholarPubMed
Zhang, X., Liu, X., Yao, X. and Zhang, S.: Microscopic Structure, Interaction, and Properties of a Guanidinium-Based Ionic Liquid and Its Mixture with CO2. Industrial & Engineering Chemistry Research 50, 8323 (2011).CrossRefGoogle Scholar
Ramdin, M., de Loos, T.W. and Vlugt, T.J.H.: State-of-the-Art of CO2 Capture with Ionic Liquids. Industrial & Engineering Chemistry Research 51, 8149 (2012).CrossRefGoogle Scholar
Pereiro, A.B., Araújo, J.M.M., Martinho, S., Alves, F., Nunes, S., Matias, A., Duarte, C.M.M., Rebelo, L.P.N. and Marrucho, I.M.: Fluorinated Ionic Liquids: Properties and Applications. ACS Sustainable Chemistry & Engineering 1, 427 (2013).CrossRefGoogle Scholar
Breen, J.M., Olejarz, S. and Seddon, K.R.: Microwave Synthesis of Short-Chained Fluorinated Ionic Liquids and Their Surface Properties. ACS Sustainable Chemistry & Engineering 4, 387 (2015).CrossRefGoogle Scholar
Almantariotis, D., Gefflaut, T., Pádua, A.A.H., Coxam, J.Y. and Costa Gomes, M.F.: Effect of Fluorination and Size of the Alkyl Side-Chain on the Solubility of Carbon Dioxide in 1-Alkyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)amide Ionic Liquids. The Journal of Physical Chemistry B 114, 3608 (2010).CrossRefGoogle ScholarPubMed