On the Use of Ionic Liquids to Separate Aromatic Hydrocarbons from a Model Soil

REFERENCES

• European Environment Agency, http://themes.eea.europa.eu/ IMS /IMS/ISpecs/ISpecification20041007131746/IAssessment1152619898983/view_content, accessed April 29, 2009 .
   Google Scholar
• Osu , C.I. , Asuoha , A.N. ( 2010 ) Polycyclic Aromatic Hydrocarbons (PAHs) and Benzene, Toluene, Ethylbenzene, and Xylene (BTEX) contamination of soils in automobile mechanic workshops in port-harcourt metropolis, Rivers State, Nigeria . J. Am. Sci. , 6 : 242 .
   Google Scholar
• Keskin , S. ; Akman , U. ; Hortaçsu , O. ( 2008 ) Soil remediation via an ionic liquid and supercritical CO2 . Chem. Eng. Proc. , 47 : 1693 .
   Web of Science ®Google Scholar
• Weissermel , K. ; Arpe , H.J. ( 2003 ) Industrial Organic Chemistry, , 4th ed. ; Wiley-WCH : Weinheim .
   Google Scholar
• Anitescu , G. ; Tavlarides , L.L. ( 2006 ) Supercritical extraction of contaminants from soils and sediments . J. Supercrit. Fluids , 38 : 167 .
   Web of Science ®Google Scholar
• Paria , S. ( 2008 ) Surfactant-enhanced remediation of organic contaminated soil and water . Adv. Colloid Interfac. , 138 : 24 .
   PubMed Web of Science ®Google Scholar
• Brennecke , J.F. ; Maginn , E.J. ( 2001 ) Ionic liquids: Innovative fluids for chemical processing . AIChE J. , 47 : 2384 .
   Web of Science ®Google Scholar
• Earle , M.J. ; Esperança , J.M.S.S. ; Gilea , M.A. ; Canongia Lopes , J.N. ; Rebelo , L.P.N. ; Magee , J.W. ; Seddon , K.R. ; Widegren , J.A. ( 2006 ) The distillation and volatility of ionic liquids . Nature , 439 : 831 .
   PubMed Web of Science ®Google Scholar
• Smiglak , M. ; Reichert , W.M. ; Holbrey , J.D. ; Wilkes , J.S. ; Sun , L.Y. ; Thrasher , J.S. ; Kirichenko , K. ; Singh , S. ; Katritzky , A.R. ; Rogers , R.D. ( 2006 ) Combustible ionic liquids by design: Is laboratory safety another ionic liquid myth? Chem. Commun. , 24 : 2554 .
   PubMed Web of Science ®Google Scholar
• Baranyai , K.J. ; Deacon , G.B. ; MacFarlane , D.R. ; Pringle , J.M. ; Scott , J.L. ( 2004 ) Thermal degradation of ionic liquids at elevated temperatures . Aust. J. Chem. , 57 : 145 .
   Web of Science ®Google Scholar
• Plechkova , N.V. ; Seddon , K.R. ( 2008 ) Applications of ionic liquids in the chemical industry . Chem. Soc. Rev. , 37 : 123 .
   PubMed Web of Science ®Google Scholar
• Pereiro , A.B. ; Rodriguez , A. ( 2008 ) Azeotrope-breaking using [BMIM] [MeSO4] ionic liquid in an extraction column . Sep. Purif. Technol. , 62 : 733 .
   Web of Science ®Google Scholar
• Gonzalez , E.J. ; Calvar , N. ; Gonzalez , B. ; Dominguez , A. ( 2010 ) Liquid extraction of benzene from its mixtures using 1-Ethyl-3-methylimidazolium ethylsulfate as a solvent . J. Chem. Eng. Data , 55 : 4931 .
   Web of Science ®Google Scholar
• Letcher , T.M. ; Reddy , P. ( 2005 ) Ternary (liquid plus liquid) equilibria for mixtures of 1-hexyl-3-methylimidazolium (tetrafluoroborate or hexafluorophosphate) plus benzene plus an alkane at T = 298.2 K and p = 0.1 Mpa . J. Chem. Thermodyn. , 37 : 415 .
   Web of Science ®Google Scholar
• Deenadayalu , N. ; Ngcongo , K.C. ; Letcher , T.M. ; Ramjugernath , D. ( 2006 ) Liquid-liquid equilibria for ternary mixtures (an ionic liquid plus benzene plus heptane or hexadecane) at T = 298.2 K and atmospheric pressure . J. Chem. Eng. Data , 51 : 988 .
   Web of Science ®Google Scholar
• Meindersma , G.W. ; Podt , A.J.G. ; de Haan , A.B. ( 2006 ) Ternary liquid-liquid equilibria for mixtures of toluene plus n-heptane plus an ionic liquid . Fluid Phase Equilib. , 247 : 158 .
   Web of Science ®Google Scholar
• Meindersma , G.W. ; Podt , A. ; de Haan , A.B. ( 2006 ) Ternary liquid-liquid equilibria for mixtures of an aromatic plus an aliphatic hydrocarbon+4-methyl-N-butylpyridinium tetrafluoroborate . J. Chem. Eng. Data , 51 : 1814 .
   Web of Science ®Google Scholar
• Domanska , U. ; Pobudkowska , A. ; Krolikowski , M. ( 2007 ) Separation of aromatic hydrocarbons from alkanes using ammonium ionic liquid C2NTf2 at T = 298.15 K . Fluid Phase Equilib. , 259 : 173 .
   Web of Science ®Google Scholar
• Domanska , U. ; Pobudkowska , A. ; Zołek-Tryznowska , Z. ( 2007 ) Effect of an ionic liquid (IL) cation on the ternary system (IL plus p-xylene plus hexane) at T = 298.15 K . J. Chem. Eng. Data , 52 : 2345 .
   Web of Science ®Google Scholar
• Cassol , C.C. ; Umpierre , A.P. ; Ebeling , G. ; Ferrera , B. ; Chiaro , S.S.X. ; Dupont , J. ( 2007 ) On the extraction of aromatic compounds from hydrocarbons by imidazolium ionic liquids . Int. J. Mol. Sci. , 8 : 593 .
   Web of Science ®Google Scholar
• Arce , A. ; Earle , M.J. ; Rodriguez , H. ; Seddon , K.R. ( 2007 ) Separation of aromatic hydrocarbons from alkanes using the ionic liquid 1-ethyl-3-methylimidazolium bis{(trifluoromethyl) sulfonyl} amide . Green Chem. , 9 : 70 .
   Web of Science ®Google Scholar
• Arce , A. ; Earle , M.J. ; Rodriguez , H. ; Seddon , K.R. ; Soto , A. ( 2008 ) 1-Ethyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}amide as solvent for the separation of aromatic and aliphatic hydrocarbons by liquid extraction - extension to C-7- and C-8-fractions . Green Chem. , 10 : 1294 .
   Web of Science ®Google Scholar
• Arce , A. ; Earle , M.J. ; Katdare , S.P. ; Rodriguez , H. ; Seddon , K.R. ( 2008 ) Application of mutually immiscible ionic liquids to the separation of aromatic and aliphatic hydrocarbons by liquid extraction: A preliminary approach . Phys. Chem. Chem. Phys. , 10 : 2538 .
   PubMed Web of Science ®Google Scholar
• Pereiro , A.B. ; Rodríguez , A. ( 2009 ) Application of the ionic liquid Ammoeng 102 for aromatic/aliphatic hydrocarbon separation . J. Chem. Thermodyn. , 41 : 951 .
   Web of Science ®Google Scholar
• Pereiro , A.B. ; Rodríguez , A. ( 2009 ) An ionic liquid proposed as solvent in aromatic hydrocarbon separation by liquid extraction . AICHE J. , 56 : 381 .
   Web of Science ®Google Scholar
• Meindersma , G.W. ; Hansmeier , A.R. ; de Haan , A.B. ( 2010 ) Ionic liquids for aromatics extraction. present status and future outlook . Ind. & Eng. Chem. Res. , 49 : 7530 .
   Web of Science ®Google Scholar
• RD 9/2005, January 14 th. Potential activities causing contaminated soil and general criteria and standards to declare as a polluted soil (in Spanish), State Official Bulletin (BOE) 15 (January, 18, 2005) .
   Google Scholar
• Pereiro , A.B. ; Legido , J.L. ; Rodríguez , A. ( 2007 ) Physical properties of ionic liquids based on 1-alkyl-3-methylimidazolium cation and hexafluorophosphate as anion and temperature dependence . J. Chem. Thermodyn. , 39 : 1168 .
   Web of Science ®Google Scholar
• Pereiro , A.B. ; Santamarta , F. ; Tojo , E. ; Rodríguez , A. ; Tojo , J. ( 2006 ) Temperature dependence of physical properties of ionic liquid 1,3-dimethylimidazolium methyl sulfate . J. Chem. Eng. Data , 51 : 952 .
   Web of Science ®Google Scholar
• Pereiro , A.B. ; Verdía , P. ; Tojo , E. ; Rodríguez , A. ( 2007 ) Physical properties of 1-butyl-3-methylimidazolium methyl sulfate as a function of temperature . J. Chem. Eng. Data , 52 : 377 .
   Web of Science ®Google Scholar
• Pereiro , A.B. ; Veiga , H.I.M. ; Esperanca , J.M.S.S. ; Rodriguez , A. ( 2009 ) Effect of temperature on the physical properties of two ionic liquids . J. Chem. Thermodyn. , 41 : 1419 .
   Web of Science ®Google Scholar
• Pereiro , A.B. ; Tojo , E. ; Rodriguez , A. ; Canosa , J. ; Tojo , J. ( 2006 ) Properties of ionic liquid HMIMPF6 with carbonates, ketones and alkyl acetates . J. Chem. Thermodynamics , 38 : 651 .
   Web of Science ®Google Scholar
• Chen , B. ; Guo , Z. ; Tan , T. ; Xu , X. (2007) Structures of ionic liquids dictate the conversion and selectivity of enzymatic glycerolysis: Theoretical characterization by COSMO-RS. Biotechnol. Bioeng. , 99: 18.
   Web of Science ®Google Scholar
• Bevington , P. ( 1969 ) Data Reduction and Error Analysis for the Physical Sciences ; McGraw-Hill : New York .
   Google Scholar
• Domanska , U. ; Pobudkowska , A. Eckert , F. ( 2006 ) Liquid–liquid equilibria in the binary systems (1,3-dimethylimidazolium, or 1-butyl-3-methylimidazolium methylsulfate +hydrocarbons) . Green Chem. , 8 : 268 .
   Web of Science ®Google Scholar
• García , J. ; Torrecilla , J.S. ; Fernández , A. ; Oliet , M. ; Rodríguez , F. ( 2010 ) (Liquid + liquid) equilibria in the binary systems (aliphatic, or aromatic hydrocarbons+1-ethyl-3-methylimidazolium ethylsulfate, or 1-butyl-3-methylimidazolium methylsulfate ionic liquids) . J. Chem. Thermodynamics , 42 : 144 .
   Web of Science ®Google Scholar
• Silva , A. ; Delerue-Matos , C. ; Fiúza , A. ( 2005 ) Use of solvent extraction to remediate soils contaminated with hydrocarbons . J. Hazard. Mat. B , 124 : 224 .
   PubMed Web of Science ®Google Scholar
• Singh1 , D. ; Fulekar , M.H. ( 2010 ) Biodegradation of petroleum hydrocarbons by Pseudomonas putida strain MHF 7109 . Clean-Soil, Air, Water , 38 : 781 .
   Web of Science ®Google Scholar
• Liu , J.H. ; Maity , J.P. ; Jean , J.S. ; Chen , C.Y. ; Chen , C.C. ; Ho , S.Y. ( 2010 ) Biodegradation of benzene by pure and mixed cultures of Bacillus spp . World J. Microbiol. Biotechnol. , 26 : 1557 .
   Web of Science ®Google Scholar
• Khodadoust , A.P. ; Chandrasekaran , S. ; Dionysiou , D.D. ( 2006 ) Preliminary assessment of imidazolium-based room-temperature ionic liquids for extraction of organic contaminants from soils . Env. Sci. Technol. , 40 : 2339 .
   PubMed Web of Science ®Google Scholar
• Matzke , M. ; Thiele , K. ; Müller , A. Filser , J. ( 2009 ) Sorption and desorption of imidazolium based ionic liquids in different soil types . Chemosphere , 74 : 568 .
   PubMed Web of Science ®Google Scholar
• Majid , S.A. ; Sparks , B.D. ( 2002 ) Removal of Aroclor 1016 from contaminated soil by solvent extraction soil agglomeration process . J. Environ. Eng. Sci. , 1 : 59 .
   Google Scholar