4.7 Article

Dual functionalized imidazolium ionic liquids as a green solvent for extractive desulfurization of fuel oil: Toxicology and mechanistic studies

Journal

JOURNAL OF CLEANER PRODUCTION
Volume 213, Issue -, Pages 989-998

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.jclepro.2018.12.207

Keywords

Ionic liquids; Dual functionality; Desulfurization; EC50; Biodegradability

Funding

  1. Centre of Research in Ionic Liquids (CORIL), Universiti Teknologi Petronas (PRF) [0153AB-A30]

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Readily biodegradable and practically non-toxic dual functionalized imidazolium ionic liquids (ILs) carrying nitrile and varying number of ether group were developed to improve the extractive desulfurization performance and ecotoxicity of ILs. Dicyanamide (N(CN)(2)), trifluoroacetate (CF3COO) and bis(trifiuoromethylsulfonyl)imide (NTf2) were selected as anions. Evaluation of thermophysical properties of the synthesized ILs revealed that bis(trifiuoromethylsulfonyl)imide anion based ILs have lowest viscosity, which contributed to excellent mass transfer and enhanced desulfurization performance. The effect of temperature, time and mass ratio (ILs: model oil) were investigated for extractive desulfurization and the performance of ILs were in the anion order; dicyanamide < trifluoroacetate < bis(trifluoromethylsulfonyl)imide. Dibenzothiophene was more selectively extracted over 4,6- dimethyldibenzothiophene. Increasing alkoxy group on the cation side chain improved the desulfurization efficiency. More than 70% of dibenzothiophene was extracted in 15 min (single stage extraction) with a mass ratio of 1.5:1 at 25 degrees C by bis(trifluoromethylsulfonyl)imide anion based ILs with three ether groups on the imidazolium cation. Conductor like Screening Model for Real Solvents tool (COSMO-RS) and FTIR spectroscopy study revealed that interaction between dibenzothiophene and ILs were mainly dominated by pi-pi interaction and hydrogen bonding. The microbial toxicity and biodegradability assessment indicated that ILs were practically harmless and readily biodegradable through the incorporation of alkoxy groups on the cationic core of bis(trifluoromethylsulfonyl)imide anion based ILs. The ILs can be reused more than 8 cycles for the desulfurization process without regeneration. (C) 2018 Elsevier Ltd. All rights reserved.

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