Effect of the type of ammonium salt on the extractive desulfurization of fuels using deep eutectic solvents

Samah E.E. Warrag, Idowu Adeyemi, Nerea R. Rodriguez, Inas M. Nashef, Martin van Sint Annaland, Maaike C. Kroon, Cor J. Peters

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Abstract

In a previous work, we proved that the deep eutectic solvents (DESs) consisting of mixtures of tetraalkylammonium salts with polyols are promising candidates for oil desulfurization based on the obtained liquid-liquid equilibrium (LLE) data. In this study, the capability of DESs containing other salts (e.g., different alkyl chain lengths or different functional groups on the ammonium cation) for the extraction of thiophene from {n-hexane + thiophene} mixtures via LLE was evaluated. Therefore, four DESs composed of tetraethylammonium chloride or methyltriphenylphosphonium bromide as hydrogen bond acceptors and ethylene glycol or glycerol as hydrogen bond donors were prepared. Thereafter, the binary solubilities of the aliphatic hydrocarbon (n-hexane) and the thiophene in DESs were measured at 298.2 K and atmospheric pressure. Next, ternary liquid-liquid equilibrium (LLE) data for the four ternary systems {n-hexane + thiophene + DES} were measured at 298.2 K and atmospheric pressure. The conductor-like screening model for real solvents (COSMO-RS) was used to better understand the extraction mechanism of thiophene. Experimentally obtained solute distribution coefficients and selectivities were calculated and compared to relevant literature. All DESs were found to be good candidates for extractive desulfurization with higher selectivities but somewhat lower distribution coefficients as compared to conventional ionic liquids. It was found that longer alkyl chain lengths on the cation yield higher distribution coefficients but lower selectivities, and the replacement of an alkyl group by a phenyl group on the cation generally yields lower distribution ratios ratios but higher selectivities.

Original languageEnglish
Pages (from-to)1088-1095
Number of pages8
JournalJournal of Chemical and Engineering Data
Volume63
Issue number4
DOIs
Publication statusPublished - 12 Apr 2018

Fingerprint

Desulfurization
Ammonium Compounds
Eutectics
Thiophenes
Salts
Thiophene
Liquids
Hexane
Cations
Positive ions
Chain length
Atmospheric pressure
Hydrogen bonds
Ionic Liquids
Tetraethylammonium
Ethylene Glycol
Polyols
Ternary systems
Hydrocarbons
Ethylene glycol

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Warrag, Samah E.E. ; Adeyemi, Idowu ; Rodriguez, Nerea R. ; Nashef, Inas M. ; van Sint Annaland, Martin ; Kroon, Maaike C. ; Peters, Cor J. / Effect of the type of ammonium salt on the extractive desulfurization of fuels using deep eutectic solvents. In: Journal of Chemical and Engineering Data. 2018 ; Vol. 63, No. 4. pp. 1088-1095.
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Effect of the type of ammonium salt on the extractive desulfurization of fuels using deep eutectic solvents. / Warrag, Samah E.E.; Adeyemi, Idowu; Rodriguez, Nerea R.; Nashef, Inas M.; van Sint Annaland, Martin; Kroon, Maaike C.; Peters, Cor J.

In: Journal of Chemical and Engineering Data, Vol. 63, No. 4, 12.04.2018, p. 1088-1095.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Effect of the type of ammonium salt on the extractive desulfurization of fuels using deep eutectic solvents

AU - Warrag, Samah E.E.

AU - Adeyemi, Idowu

AU - Rodriguez, Nerea R.

AU - Nashef, Inas M.

AU - van Sint Annaland, Martin

AU - Kroon, Maaike C.

AU - Peters, Cor J.

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N2 - In a previous work, we proved that the deep eutectic solvents (DESs) consisting of mixtures of tetraalkylammonium salts with polyols are promising candidates for oil desulfurization based on the obtained liquid-liquid equilibrium (LLE) data. In this study, the capability of DESs containing other salts (e.g., different alkyl chain lengths or different functional groups on the ammonium cation) for the extraction of thiophene from {n-hexane + thiophene} mixtures via LLE was evaluated. Therefore, four DESs composed of tetraethylammonium chloride or methyltriphenylphosphonium bromide as hydrogen bond acceptors and ethylene glycol or glycerol as hydrogen bond donors were prepared. Thereafter, the binary solubilities of the aliphatic hydrocarbon (n-hexane) and the thiophene in DESs were measured at 298.2 K and atmospheric pressure. Next, ternary liquid-liquid equilibrium (LLE) data for the four ternary systems {n-hexane + thiophene + DES} were measured at 298.2 K and atmospheric pressure. The conductor-like screening model for real solvents (COSMO-RS) was used to better understand the extraction mechanism of thiophene. Experimentally obtained solute distribution coefficients and selectivities were calculated and compared to relevant literature. All DESs were found to be good candidates for extractive desulfurization with higher selectivities but somewhat lower distribution coefficients as compared to conventional ionic liquids. It was found that longer alkyl chain lengths on the cation yield higher distribution coefficients but lower selectivities, and the replacement of an alkyl group by a phenyl group on the cation generally yields lower distribution ratios ratios but higher selectivities.

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