Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering Solvents
In this work, a set of novel fluorinated ionic liquids (FILs), based on different tetra-alkyl-phosphonium cations with perfluorobutanesulfonate and perfluoropentanoate anions, were synthesized and characterized in order to check their suitability to apply as engineering solvents. Thermophysical and...
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| Format: | Article |
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MDPI AG
2022-05-01
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| Series: | ChemEngineering |
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| Online Access: | https://www.mdpi.com/2305-7084/6/3/38 |
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| author | María C. Naranjo Andres E. Redondo Jacqueline C. Acuña Nicole S. M. Vieira João M. M. Araújo Ana B. Pereiro |
| author_facet | María C. Naranjo Andres E. Redondo Jacqueline C. Acuña Nicole S. M. Vieira João M. M. Araújo Ana B. Pereiro |
| author_sort | María C. Naranjo |
| collection | DOAJ |
| description | In this work, a set of novel fluorinated ionic liquids (FILs), based on different tetra-alkyl-phosphonium cations with perfluorobutanesulfonate and perfluoropentanoate anions, were synthesized and characterized in order to check their suitability to apply as engineering solvents. Thermophysical and thermal properties were both determined between 293.15 and 353.15 K, and the molecular volumes and free volumes and the coefficients of isobaric thermal expansion were determined from experimental values of refractive index and density. Lastly, the Walden plot was used to evaluate the ionicity of the novel FILs. The cytotoxicity of these compounds was also determined using the human hepatocellular carcinoma cells (HepG2) and the human colon carcinoma cells (Caco-2). Finally, the results were all discussed with the aim of understanding the behaviour of these compounds, considering the influence of the anion and the hydrogenated alkyl chain length. In summary, the new FILs synthesized in this work present adequate properties for their application in different industrial processes. Most of these compounds are liquid at room temperature with high decomposition temperatures. All phosphonium-based FILs have lower densities than conventional ionic liquids and common organic solvents, and the viscosity depends directly on the selected anion. Furthermore, the ionicity of FILs based on the sulfonate anion is higher than those based on the carboxylate anion. Finally, the phosphonium-based FILs have no significant effect on cellular viability at lower concentrations. |
| first_indexed | 2024-03-10T00:09:19Z |
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| institution | Directory Open Access Journal |
| issn | 2305-7084 |
| language | English |
| last_indexed | 2024-03-10T00:09:19Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | ChemEngineering |
| spelling | doaj.art-92f1ecea3dcf440985701d6e42f7b8162023-11-23T16:03:11ZengMDPI AGChemEngineering2305-70842022-05-01633810.3390/chemengineering6030038Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering SolventsMaría C. Naranjo0Andres E. Redondo1Jacqueline C. Acuña2Nicole S. M. Vieira3João M. M. Araújo4Ana B. Pereiro5LAQV, REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA University Lisbon, 2829-516 Caparica, PortugalLAQV, REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA University Lisbon, 2829-516 Caparica, PortugalFaculty of Architecture and Engineering, Chemical Engineering Research Group, SINVINQ, University of Pamplona, Pamplona 543050, ColombiaLAQV, REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA University Lisbon, 2829-516 Caparica, PortugalLAQV, REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA University Lisbon, 2829-516 Caparica, PortugalLAQV, REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA University Lisbon, 2829-516 Caparica, PortugalIn this work, a set of novel fluorinated ionic liquids (FILs), based on different tetra-alkyl-phosphonium cations with perfluorobutanesulfonate and perfluoropentanoate anions, were synthesized and characterized in order to check their suitability to apply as engineering solvents. Thermophysical and thermal properties were both determined between 293.15 and 353.15 K, and the molecular volumes and free volumes and the coefficients of isobaric thermal expansion were determined from experimental values of refractive index and density. Lastly, the Walden plot was used to evaluate the ionicity of the novel FILs. The cytotoxicity of these compounds was also determined using the human hepatocellular carcinoma cells (HepG2) and the human colon carcinoma cells (Caco-2). Finally, the results were all discussed with the aim of understanding the behaviour of these compounds, considering the influence of the anion and the hydrogenated alkyl chain length. In summary, the new FILs synthesized in this work present adequate properties for their application in different industrial processes. Most of these compounds are liquid at room temperature with high decomposition temperatures. All phosphonium-based FILs have lower densities than conventional ionic liquids and common organic solvents, and the viscosity depends directly on the selected anion. Furthermore, the ionicity of FILs based on the sulfonate anion is higher than those based on the carboxylate anion. Finally, the phosphonium-based FILs have no significant effect on cellular viability at lower concentrations.https://www.mdpi.com/2305-7084/6/3/38synthesisfluorinated ionic liquidsthermal propertiesthermophysical propertiescytotoxicity |
| spellingShingle | María C. Naranjo Andres E. Redondo Jacqueline C. Acuña Nicole S. M. Vieira João M. M. Araújo Ana B. Pereiro Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering Solvents ChemEngineering synthesis fluorinated ionic liquids thermal properties thermophysical properties cytotoxicity |
| title | Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering Solvents |
| title_full | Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering Solvents |
| title_fullStr | Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering Solvents |
| title_full_unstemmed | Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering Solvents |
| title_short | Synthesis and Characterization of Fluorinated Phosphonium Ionic Liquids to Use as New Engineering Solvents |
| title_sort | synthesis and characterization of fluorinated phosphonium ionic liquids to use as new engineering solvents |
| topic | synthesis fluorinated ionic liquids thermal properties thermophysical properties cytotoxicity |
| url | https://www.mdpi.com/2305-7084/6/3/38 |
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