Liquid–liquid extraction of sulfur compounds from heptane with tricyanomethanide based ionic liquids

Marek Królikowski


Liquid–liquid phase equilibrium (LLE) data for the {tricyanomethanide-based ionic liquid (1) + tiophene, or benzothiophene (2) + heptane (3)} ternary systems were experimentally determined at T = 308.15 K and at pressure p = 0.1 MPa. In this work three ILs, that is: 1-butyl-1-methylmorpholinium tricyanomethanide, [BMMOR][TCM], 1-butyl-1-methylpyrrolidinium tricyanomethanide, [BMPYR][TCM] and 1-hexyl-1-methylmorpholinium tricyanomethanide, [HMMOR][TCM] have been investigated. The high solubility of sulfur compounds and practically complete immiscibility of heptane with the tested ionic liquids have been observed. The selectivity, and solute distribution ratio, derived from the experimental equilibrium data, were calculated and used to determine the efficiency of these ionic liquids as solvents for the extraction of sulfur compounds from model fuels. The experimental results have been compared to literature data for other tricyanomethanide-based ILs and were discussed in terms of the selectivity and solute distribution ratio of separation of related systems. The NRTL equation was successfully used to correlate the experimental tie-lines. The average root mean square (RMSD) of the phase composition was less than 0.8%. Additionally, the oxidative-extractive desulfurization of model fuels has been studied using tricyanomethanide-based ionic liquid (IL): [BMMOR][TCM] and [BMPYR][TCM] and deep eutectic solvent (DES): ([BMMOR] [Br] + diethylene glycol). Model liquid fuel was prepared by dissolving benzothiophene in octane, 500 ppm of sulfur. Oxidation was achieved by adding hydrogen peroxide and acetic acid to the mixture. Different parameters such as a type of extractant, extraction time, and oxidant to sulfur molar ratio and temperature were optimized. The addition of oxidizing agent improves the efficiency of sulfur extraction and the highest extraction efficiency, equal to 69.1%, was obtained for [BMMOR][TCM] at T = 318.15 K.
Author Marek Królikowski (FC / DPC)
Marek Królikowski,,
- Department Of Physical Chemistry
Journal seriesJournal of Chemical Thermodynamics, ISSN 0021-9614
Issue year2019
Publication size in sheets0.5
Keywords in EnglishDesulfurization(Liquid + liquid) phase equilibriaTricyanomethanide ionic liquidHeptaneThiopheneDibenzothiophene
ASJC Classification1606 Physical and Theoretical Chemistry; 2500 General Materials Science; 3107 Atomic and Molecular Physics, and Optics
Languageen angielski
1-s2.0-S0021961418308450-main.pdf 1.67 MB
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 26-06-2020, ArticleFromJournal
Publication indicators Scopus Citations = 7; WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 1.06; WoS Impact Factor: 2018 = 2.29 (2) - 2018=2.257 (5)
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