Investigating the solubility of chlorophenols in hydrophobic ionic liquids

R. Sulaiman, M. K. Hadj-Kali, S. W. Hasan, S. Mulyono, I. M. AlNashef

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Chlorophenols (CPs) are synthetic chemicals that are generated and used widely by different industries such as textile, pharmaceutical, metallurgic, oil, and pulp and paper manufacturing. Except water, most of the solvents used in these industries are volatile and toxic. Therefore, there is an imminent need for replacing these solvents by solvents that have less negative impact on the environment. In addition, CPs are considered as hazardous pollutants due to their resistance to biodegradation and persistence in the environment. Their toxic effects are severe including DNA damage, endocrine disruption, cytotoxicity, mutagenicity, and carcinogenicity. Hence, the water contaminated by CPs must be treated before being released to the environment. Ionic liquids (ILs) are molten salts that are liquid below 100 °C, which have been used as solvents for many processes including liquid-liquid extraction and as electrolytes in electrochemical devices. ILs are characterized by negligible vapor pressure and non-flammability. These compounds are liquid over a wide range of temperatures; possess high thermal and chemical stability. ILs are being used as media for many reactions to reduce the negative impact of traditional solvents on the environment. In addition, using ILs as green solvents in water treatment has become a research hotspot. Solubility data of CPs in ILs is important for assessing the potential use of ILs as reaction media and in water treatment, but relevant data for ILs are scarce. To our best knowledge, no solubility data of chlorophenols in ILs were reported in the literature. Thus, in this study, the solubility of 3-chlorophenol (3-CP), 2,5-dichlorophenol (DCP), 2,4,6-trichlorophenol (TCP), and pentachlorophenol (PCP) in six hydrophobic bis(trifluoromethylsulfonyl)imide based ILs at 25 °C, 35 °C and 45 °C was investigated. It was found that the solubility of 3-CP in all studied ILs at 25 °C was greater than 70 wt%, thus the solubility measurements of 3-chlorophenol in the studied IL were stopped at 70 wt% and further measurement was not conducted. The solubility of other CPs in all studied ILs decreased with increasing the number of chlorine atoms in the CP and increased with the increase in temperature, but the degree of increase depended on the structure of both the IL and chlorinated phenol. In general, it was found that the tested chlorophenols have substantial solubility in pyridinium and imidazolium-based ILs. In addition, the non-random two-liquid model (NRTL) and Conductor-like Screening Model for Real Solvents (COSMO-RS) models were applied to predict the solubility of chlorophenols in all ILs used in this study. There was a good quantitative and qualitative agreement between experimental and calculated solubility data in most of the cases.

Original languageBritish English
Pages (from-to)97-106
Number of pages10
JournalJournal of Chemical Thermodynamics
Volume135
DOIs
StatePublished - Aug 2019

Keywords

  • Chlorophenols
  • COSMO-RS
  • Hydrophobic ionic liquids
  • Ionic liquids
  • NRTL
  • Solubility
  • Water pollutants

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