Extraction of Alcohols, Phenols, and Aromatic Compounds with ABS

  1. Pino, Verónica 1
  2. Ayala, Juan H. 1
  3. Trujillo-Rodríguez, María J.
  1. 1 Universidad de La Laguna
    info

    Universidad de La Laguna

    San Cristobal de La Laguna, España

    ROR https://ror.org/01r9z8p25

Libro:
Ionic-Liquid-Based Aqueous Biphasic Systems: Fundamentals and Applications

Editorial: Springer

ISSN: 2196-6982,  2196-6990

ISBN: 978-3-662-52875-4,  978-3-662-52873-0

Año de publicación: 2016

Páginas: 135-159

Tipo: Capítulo de Libro

DOI: 10.1007/978-3-662-52875-4_7 GOOGLE SCHOLAR lock_openAcceso abierto editor

Objetivos de desarrollo sostenible

Resumen

Ionic-liquid-based aqueous biphasic systems (IL-based ABS) combine the advantages of both ionic liquids (ILs) and aqueous biphasic systems (ABS) in extraction approaches. Most ILs are liquid solvents exclusively composed of ions, characterized for low to negligible vapor pressures at ambient conditions, extraordinary chemical and thermal stabilities, and impressive solvation abilities for polar to nonpolar compounds, among many other properties. ABS permit the development of extraction methods without the need of using toxic and volatile organic solvents, while both immiscible phases involved in the extraction procedure are aqueous rich. Thus, the combination of hydrophilic ILs with ABS has implied numerous effective applications for different target compounds. In this chapter, attention is focused on applications of IL-based ABS for the extraction of alcohols, phenols, aromatic dyes, and other aromatic compounds. The discussion is centered on the nature of the IL-based ABS, their characterization, and the performance of the extraction procedure, among other features.

Referencias bibliográficas

  • Welton T (1999) Room–temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071–2083
  • Rogers RD, Seddon KR (2003) Ionic liquids–solvents of the future? Science 302:792–793
  • Hallett JP, Welton T (2011) Room–temperature ionic liquids: solvents for synthesis and catalysis. Chem Rev 111:3508–3576
  • Ho TD, Zhang C, Hantao LW, Anderson JL (2014) Ionic liquids in analytical chemistry: fundamentals, advances, and perspectives. Anal Chem 86:262–285
  • Müller K, Albert J (2014) Contribution of the individual ions to the heat capacity of ionic liquids. Ind Eng Chem Res 53:10343–10346
  • Karunanithi AT, Mehrkesh A (2013) Computer−aided design of tailor−made ionic liquids. AICHE J 59:4627–4640
  • Davis JH (2004) Task–specific ionic liquids. Chem Lett 33:1072–1077
  • Swatloski RP, Holbrey JD, Rogers RD (2003) Ionic liquids are not always green: hydrolysis of 1–butyl–3–methylimidazolium hexafluorophosphate. Green Chem 5:361–363
  • Pham TPT, Cho CW, Yun YS (2010) Environmental fate and toxicity of ionic liquids: a review. Water Res 44:352–372
  • Cevasco G, Chiappe C (2014) Are ionic liquids a proper solution to current environmental challenges? Green Chem 16:2375–2385
  • Welton T (2011) Ionic liquids in green chemistry. Green Chem 13:225
  • Bubalo MC, Radošević K, Redovniković IR, Halambek J, Srček VG (2014) A brief overview of the potential environmental hazards of ionic liquids. Ecotoxicol Environ Saf 99:1–12
  • MacFarlane DR, Tachikawa N, Forsyth M, Pringle JM, Howlett PC, Elliott GD, Davis JH, Watanabe M, Simon P, Angell CA (2014) Energy applications of ionic liquids. Energy Environ Sci 7:232–250
  • Smiglak M, Pringle JM, Lu X, Han L, Zhang S, Gao H, MacFarlane DR, Rogers RD (2014) Ionic liquids for energy, materials, and medicine. Chem Commun 50:9228–9250
  • Armand M, Endres F, MacFarlane DR, Ohno H, Scrosati B (2009) Ionic–liquid materials for the electrochemical challenges of the future. Nat Mater 8:621–629
  • Nevagi RJ, Dighe SN, Dighe SN, Chaskar PK, Srinivasan KV, Jain KS (2014) Use of ionic liquids as neoteric solvents in the synthesis of fused heterocycles. Arch Pharm Chem Life Sci 347:540–551
  • Díaz M, Ortiz A, Ortiz I (2014) Progress in the use of ionic liquids as electrolyte membranes in fuel cells. J Membr Sci 469:379–396
  • Kar M, Simons TJ, Forsyth M, MacFarlane DR (2014) Ionic liquid electrolytes as a platform for rechargeable metal–air batteries: a perspective. Phys Chem Chem Phys 16:18658–18674
  • Werner S, Haumann M, Wasserscheid P (2010) Ionic liquids in chemical engineering. Annu Rev Chem Biomol Eng 1:203–230
  • Tan Z-Q, Liu J-F, Pang L (2012) Advances in analytical chemistry using the unique properties of ionic liquids. Trends Anal Chem 39:218–227
  • Joshi MD, Anderson JL (2012) Recent advances of ionic liquids in separation science and mass spectrometry. RSC Adv 2:5470–5484
  • Marrucho IM, Branco LC, Rebelo LPN (2014) Ionic liquids in pharmaceutical applications. Annu Rev Chem Biomol Eng 5:527–546
  • Fontanals N, Borrull F, Marcé RM (2012) Ionic liquids in solid–phase extraction. Trends Anal Chem 41:15–26
  • Trujillo–Rodríguez MJ, Rocío–Bautista P, Pino V, Afonso AM (2013) Ionic liquids in dispersive liquid–liquid microextraction. Trends Anal Chem 51:87–106
  • Liu R, Liu J-F, Yin Y-G, Hu X-L, Jiang G-B (2009) Ionic liquids in sample preparation. Anal Bioanal Chem 393:871–883
  • Poole CF, Poole SK (2010) Extraction of organic compounds with room temperature ionic liquids. J Chromatogr A 1217:2268–2286
  • Freire MG, Cláudio AFM, Araújo JMM, Coutinho JAP, Marrucho IM, Canongia Lopes JN, Rebelo LPN (2012) Aqueous biphasic systems: a boost brought about by using ionic liquids. Chem Soc Rev 41:4966–4995
  • Pereira JBF, Ventura SPM, e Silva FA, Shahriari S, Freire MG, Coutinho JAP (2013) Aqueous biphasic systems composed of ionic liquids and polymers: a platform for the purification of biomolecules. Sep Purif Technol 113:83–89
  • Gutowski KE, Broker GA, Willauer HD, Huddleston JG, Swatloski RP, Holbrey JD, Rogers RD (2003) Controlling the aqueous miscibility of ionic liquids: aqueous biphasic systems of water–miscible ionic liquids and water–structuring salts for recycle, metathesis, and separations. J Am Chem Soc 125:6632–6633
  • Li Z, Pei Y, Wang H, Fan J, Wang J (2010) Ionic liquid–based aqueous two-phase systems and their applications in green separation processes. Trends Anal Chem 29:1336–1346
  • Pereira JBF, Rebelo LPN, Rogers RD, Coutinho JAP, Freire MG (2013) Combining ionic liquids and polyethylene glycols to boost the hydrophobic–hydrophilic range of aqueous biphasic systems. Phys Chem Chem Phys 15:19580–19583
  • de Souza RL, Campos VC, Ventura SPM, Soares CMF, Coutinho JAP, Lima AS (2014) Effect of ionic liquids as adjuvants on PEG–based ABS formation and the extraction of two probe dyes. Fluid Phase Equilib 375:30–36
  • Passos H, Sousa ACA, Pastorinho MR, Nogueira AJA, Rebelo LPN, Coutinho JAP, Freire MG (2012) Ionic–liquid–based aqueous biphasic systems for improved detection of bisphenol A in human fluids. Anal Methods 4:2664–2667
  • Ferreira AM, Coutinho JAP, Fernandes AM, Freire MG (2014) Complete removal of textile dyes from aqueous media using ionic–liquid–based aqueous two–phase systems. Sep Purif Technol 128:58–66
  • Müller A, Górak A (2012) Extraction of 1,3–propanediol from aqueous solutions using different ionic liquid–based aqueous two-phase systems. Sep Purif Technol 97:130–136
  • Moscoso F, Deive FJ, Esperança JMSS, Rodríguez A (2013) Pesticide removal from aqueous solutions by adding salting out agents. Int J Mol Sci 14:20954–20965
  • Chen Y, Meng Y, Yang J, Li H, Liu X (2012) Phenol distribution behavior in aqueous biphasic systems composed of ionic liquids–carbohydrate–water. J Chem Eng Data 57:1910–1914
  • Hirayama N, Higo T, Imura H (2012) Evaluation of a hydrophilic ionic liquid as a salting–out phase separation agent to a water–tetrahydrofuran homogeneous system for aqueous biphasic extraction separation. Anal Sci 28:541–543
  • Zhang D, Deng Y, Chen J (2010) Enrichment of aromatic compounds using ionic liquid and ionic liquid–based aqueous biphasic systems. Sep Sci Technol 45:663–669
  • Noorashikin MS, Mohamad S, Abas MR (2014) Extraction and determination of parabens in water samples using an aqueous two–phase system of ionic liquid and salts with beta–cyclodextrin as the modifier coupled with high performance liquid chromatography. Anal Methods 6:419–425
  • Ruiz–Angel MJ, Pino V, Carda–Broch S, Berthod A (2007) Solvent systems for countercurrent chromatography: an aqueous two phase liquid system based on a room temperature ionic liquid. J Chromatogr A 1151:65–73
  • Sheikhian L, Akhond M, Absalan G (2014) Partitioning of reactive red–120, 4– (2–pyridylazo) –resorcinol, and methyl orange in ionic liquid–based aqueous biphasic systems. J Environ Chem Eng 2:137–142
  • Amini M, Arami M, Mahmoodi NM, Akbari A (2011) Dye removal from colored textile wastewater using acrylic grafted nanomembrane. Desalination 267:107–113
  • Harrelkas F, Azizi A, Yaacoubi A, Benhammou A, Pons MN (2009) Treatment of textile dye effluents using coagulation–flocculation coupled with membrane processes or adsorption on powdered activated carbon. Desalination 235:330–339
  • Charumathi D, Das N (2012) Packed bed column studies for the removal of synthetic dyes from textile wastewater using immobilised dead C. tropicalis. Desalination 285:22–30
  • Aksu Z, Tezer S (2005) Biosorption of reactive dyes on the green alga Chlorella vulgaris. Process Biochem 40:1347–1361
  • Kiran I, Akar T, Ozcan AS, Ozcan A, Tunali S (2006) Biosorption kinetics and isotherm studies of Acid Red 57 by dried Cephalosporium aphidicola cells from aqueous solutions. Biochem Eng J 31:197–203
  • Taylor P, Gagan M (eds) (2002) Alkenes and aromatics. In: The molecular word. The Open University, Cambridge
  • Ortiz de García S, Pinto Pinto G, García Encina P, Irusta Mata R (2013) Consumption and occurrence of pharmaceutical and personal care products in the aquatic environment in Spain. Sci Total Environ 444:451–465
  • Etschmann MMW, Bluemke W, Sell D, Schrader J (2002) Biotechnological production of 2–phenylethanol. Appl Microbiol Biotechnol 59:1–8
  • Flint S, Markle T, Thompson S, Wallace E (2012) Bisphenol a exposure, effects, and policy: a wildlife perspective. J Environ Manag 104:19–34
  • Feng Y, Su G, Zhao H, Cai Y, Cui C, Sun-Waterhouse D, Zhao M (2015) Characterisation of aroma profiles of commercial soy sauce by odour activity value and omission test. Food Chem 167:220–228
  • Pal A, He Y, Jekel M, Reinhard M, Gin KY-H (2014) Emerging contaminants of public health significance as water quality indicator compounds in the urban water cycle. Environ Int 71:46–62
  • Kovacic P, Somanathan R (2014) Nitroaromatic compounds: environmental toxicity, carcinogenicity, mutagenicity, therapy and mechanism. J Appl Toxicol 34:810–824
  • Banat FA, Al–Bailey B, Al–Asheh S, Hayajneh O (2000) Adsorption of phenol by bentonite. Environ Pollut 107:391–398
  • Dutta NN, Brothakur S, Baruaha R (1998) A novel process for recovery of phenol from alkaline wastewater: laboratory study and predesign cost estimate. Water Environ Res 70:4–9
  • United States Environmental Protection Agency EPA (2013) Alphabetical list of national primary and secondary drinking water standards. http://water.epa.gov/lawsregs/rulesregs/regulatingcontaminants/basicinformation.cfm . Accessed 6 Jul 2016
  • Roger MS (eds) (2001) Handbook of analytical separations, Vol 3. Environmental analysis. Elsevier. Amsterdam
  • Kraus G (2008) Synthetic methods for the preparation of 1,3–propanediol. Clean–Soil Air Water 36:648–651