Use of green alternative solvents in dispersive liquid-liquid microextraction: A review.
deep eutectic solvents
dispersive liquid-liquid microextraction
green chemistry
supramolecular solvents
Journal
Journal of separation science
ISSN: 1615-9314
Titre abrégé: J Sep Sci
Pays: Germany
ID NLM: 101088554
Informations de publication
Date de publication:
Jan 2022
Jan 2022
Historique:
revised:
01
09
2021
received:
30
07
2021
accepted:
01
09
2021
pubmed:
8
9
2021
medline:
8
9
2021
entrez:
7
9
2021
Statut:
ppublish
Résumé
Dispersive liquid-liquid microextraction is one of the most widely used microextraction techniques currently in the analytical chemistry field, mainly due to its simplicity and rapidity. The operational mode of this approach has been constantly changing since its introduction, adapting to new trends and applications. Most of these changes are related to the nature of the solvent employed for the microextraction. From the classical halogenated solvents (e.g., chloroform or dichloromethane), different alternatives have been proposed in order to obtain safer and non-pollutants microextraction applications. In this sense, low-density solvents, such as alkanols, switchable hydrophobicity solvents, and ionic liquids were the first and most popular replacements for halogenated solvents, which provided similar or better results than these classical dispersive liquid-liquid microextraction solvents. However, despite the good performances obtained with low-density solvents and ionic liquids, researchers have continued investigating in order to obtain even greener solvents for dispersive liquid-liquid microextraction. For that reason, in this review, the evolution over the last five years of the three types of solvents already mentioned and two of the most promising solvent alternatives (i.e., deep eutectic solvents and supramolecular solvents), have been studied in detail with the purpose of discussing which one provides the greenest alternative.
Identifiants
pubmed: 34490730
doi: 10.1002/jssc.202100609
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
210-222Subventions
Organisme : Spanish Ministry of Science and Innovation
ID : PID2020-118924RB-I00
Informations de copyright
© 2021 The Authors. Journal of Separation Science published by Wiley-VCH GmbH.
Références
Armenta S, Garrigues S, de la Guardia M. The role of green extraction techniques in Green Analytical Chemistry. TrAC Trends Anal Chem. 2015;71:2-8.
Jalili V, Barkhordari A, Ghiasvand A. New extraction media in microextraction techniques. A review of reviews. Microchem J. 2020;153:104386.
Rezaee M, Assadi Y, Milani Hosseini MR, Aghaee E, Ahmadi F, Berijani S. Determination of organic compounds in water using dispersive liquid-liquid microextraction. J Chromatogr A. 2006;1116:1-9.
Psillakis E. Vortex-assisted liquid-liquid microextraction revisited. TrAC Trends Anal Chem. 2019;113:332-9.
Albero B, Tadeo JL, Pérez RA. Ultrasound-assisted extraction of organic contaminants. TrAC Trends Anal Chem. 2019;118:739-50.
An J, Trujillo-Rodríguez MJ, Pino V, Anderson JL. Non-conventional solvents in liquid phase microextraction and aqueous biphasic systems. J Chromatogr A. 2017;1500:1-23.
Leong MI, Huang SD. Dispersive liquid-liquid microextraction method based on solidification of floating organic drop combined with gas chromatography with electron-capture or mass spectrometry detection. J Chromatogr A. 2008;1211:8-12.
Zanjani MRK, Yamini Y, Shariati S, Jönsson JÅ. A new liquid-phase microextraction method based on solidification of floating organic drop. Anal Chim Acta. 2007;585:286-93.
Musarurwa H, Tavengwa NT. Deep eutectic solvent-based dispersive liquid-liquid micro-extraction of pesticides in food samples. Food Chem. 2021;342:127943.
Food E, Authority S. Conclusion on the peer review of the pesticide risk assessment of the active substance 1-decanol. EFSA J. 2010;8:1-42.
Alshana U, Hassan M, Al-Nidawi M, Yilmaz E, Soylak M. Switchable-hydrophilicity solvent liquid-liquid microextraction. TrAC Trends Anal Chem. 2020;131:116025.
Bazel Y, Rečlo M, Chubirka Y. Switchable hydrophilicity solvents in analytical chemistry. Five years of achievements. Microchem J. 2020;157:105115.
Murata K, Yokoyama Y, Ikeda S. Homogeneous liquid-liquid extraction method : extraction of iron(III) thenoyltrifluoroacetonate by propylene carbonate. Anal Chem. 1972;44:805-10.
Vakh C, Pochivalov A, Andruch V, Moskvin L, Bulatov A. A fully automated effervescence-assisted switchable solvent-based liquid phase microextraction procedure: Liquid chromatographic determination of ofloxacin in human urine samples. Anal Chim Acta. 2016;907:54-9.
Pochivalov A, Vakh C, Garmonov S, Moskvin L, Bulatov A. An automated in-syringe switchable hydrophilicity solvent-based microextraction. Talanta 2020;209:120587.
Behpour M, Nojavan S, Asadi S, Shokri A. Combination of gel-electromembrane extraction with switchable hydrophilicity solvent-based homogeneous liquid-liquid microextraction followed by gas chromatography for the extraction and determination of antidepressants in human serum, breast milk and wastewater. J Chromatogr A. 2020;1621:461041.
Reclo M, Yilmaz E, Soylak M, Andruch V, Bazel Y. Ligandless switchable solvent based liquid phase microextraction of nickel from food and cigarette samples prior to its micro-sampling flame atomic absorption spectrometric determination. J Mol Liq. 2017;237:236-41.
Erarpat S, Bodur S, Er EÖ, Bakırdere S. Combination of ultrasound-assisted ethyl chloroformate derivatization and switchable solvent liquid-phase microextraction for the sensitive determination of L-methionine in human plasma by GC-MS. J Sep Sci. 2020;43:1100-6.
Vanderveen JR, Durelle J, Jessop PG. Design and evaluation of switchable-hydrophilicity solvents. Green Chem. 2014;16:1187-97.
Guest I, Varma DR. Developmental toxicity of methylamines in mice. J Toxicol Environ Health. 1991;32:319-30.
Zeiger E. Review of toxicological literature. Integrated laboratory systems. 1997;1-63.
Regulation (EU) no 528/2012 concerning the making available on the market and use of biocidal products. Assesment Report: Octanoic acid; 2012.
Regulation (EU) no 528/2012 concerning the making available on the market and use of biocidal products. Assesment Report: Decanoic acid; 2012.
Aguilera-Herrador E, Lucena R, Cárdenas S, Valcárcel M. The roles of ionic liquids in sorptive microextraction techniques. TrAC Trends Anal Chem. 2010;29:602-16.
Han D, Tang B, Ri Lee Y, Ho Row K. Application of ionic liquid in liquid phase microextraction technology. J Sep Sci. 2012;35:2949-61.
Yavir K, Konieczna K, Marcinkowski Ł, Kloskowski A. Ionic liquids in the microextraction techniques: the influence of ILs structure and properties. TrAC Trends Anal Chem. 2020;130:115994.
Trujillo-Rodríguez MJ, Rocío-Bautista P, Pino V, Afonso AM. Ionic liquids in dispersive liquid-liquid microextraction. TrAC Trends Anal Chem. 2013;51:87-106.
Liu Y, Zhao E, Zhu W, Gao H, Zhou Z. Determination of four heterocyclic insecticides by ionic liquid dispersive liquid-liquid microextraction in water samples. J Chromatogr A. 2009;1216:885-91.
Feng J, Loussala HM, Han S, Ji X, Li C, Sun M. Recent advances of ionic liquids in sample preparation. TrAC Trends Anal Chem. 2020;125:115833.
Carda-Broch S, Ruiz-Ángel MJ. Ionic liquids in analytical chemistry. 1st ed. Elsevier: Amsterdam; 2021.
Marcinkowska R, Konieczna K, Marcinkowski Ł, Namieśnik J, Kloskowski A. Application of ionic liquids in microextraction techniques: current trends and future perspectives. TrAC Trends Anal Chem. 2019;119:115614.
Chisvert A, Román IP, Vidal L, Canals A. Simple and commercial readily-available approach for the direct use of ionic liquid-based single-drop microextraction prior to gas chromatography. Determination of chlorobenzenes in real water samples as model analytical application. J Chromatogr A. 2009;1216:1290-5.
Aguilera-Herrador E, Lucena R, Cárdenas S, Valcárcel M. Direct coupling of ionic liquid based single-drop microextraction and GC/MS. Anal Chem. 2008;80:793-800.
Zhao FQ, Li J, Zeng BZ. Coupling of ionic liquid-based headspace single-drop microextraction with GC for sensitive detection of phenols. J Sep Sci. 2008;31:3045-9.
Zhao F, Lu S, Du W, Zeng B. Ionic liquid-based headspace single-drop microextraction coupled to gas chromatography for the determination of chlorobenzene derivatives. Microchim Acta. 2009;165:29-33.
De Boeck M, Damilano G, Dehaen W, Tytgat J, Cuypers E. Evaluation of 11 ionic liquids as potential extraction solvents for benzodiazepines from whole blood using liquid-liquid microextraction combined with LC-MS/MS. Talanta 2018;184:369-74.
Jackson GP, Duckworth DC. Electrospray mass spectrometry of undiluted ionic liquids. Chem Commun. 2004;4:522-3.
Plechkova NV, Seddon KR. Applications of ionic liquids in the chemical industry. Chem Soc Rev. 2008;37:123-50.
Deetlefs M, Seddon KR. Assessing the greenness of some typical laboratory ionic liquid preparations. Green Chem. 2010;12:17-30.
Ballesteros-Gómez A, Sicilia MD, Rubio S. Supramolecular solvents in the extraction of organic compounds. A review. Anal Chim Acta. 2010;677:108-30.
Rubio S. Twenty years of supramolecular solvents in sample preparation for chromatography: achievements and challenges ahead. Anal Bioanal Chem. 2020;412:6037-58.
Ballesteros-Gómez A, Rubio S, Pérez-Bendito D. Potential of supramolecular solvents for the extraction of contaminants in liquid foods. J Chromatogr A. 2009;1216:530-9.
Feizi N, Yamini Y, Moradi M, Ebrahimpour B. Nano-structured gemini-based supramolecular solvent for the microextraction of cyhalothrin and fenvalerate. J Sep Sci. 2016;39:3400-9.
Moradi M, Yamini Y, Feizi N. Development and challenges of supramolecular solvents in liquid-based microextraction methods. TrAC Trends Anal Chem. 2021;138:116231.
Seebunrueng K, Dejchaiwatana C, Santaladchaiyakit Y, Srijaranai S. Development of supramolecular solvent based microextraction prior to high performance liquid chromatography for simultaneous determination of phenols in environmental water. RSC Adv. 2017;7:50143-9.
Salatti-Dorado JÁ, Caballero-Casero N, Sicilia MD, Lunar ML, Rubio S. The use of a restricted access volatile supramolecular solvent for the LC/MS-MS assay of bisphenol A in urine with a significant reduction of phospholipid-based matrix effects. Anal Chim Acta. 2017;950:71-9.
Zong Y, Chen J, Hou J, Deng W, Liao X, Xiao Y. Hexafluoroisopropanol-alkyl carboxylic acid high-density supramolecular solvent based dispersive liquid-liquid microextraction of steroid sex hormones in human urine. J Chromatogr A. 2018;1580:12-21.
Chen J, Deng W, Li X, Wang X, Xiao Y. Hexafluoroisopropanol/Brij-35 based supramolecular solvent for liquid-phase microextraction of parabens in different matrix samples. J Chromatogr A. 2019;1591:33-43.
Gissawong N, Boonchiangma S, Mukdasai S, Srijaranai S. Vesicular supramolecular solvent-based microextraction followed by high performance liquid chromatographic analysis of tetracyclines. Talanta 2019;200:203-11.
Najafi A, Hashemi M. Feasibility of liquid phase microextraction based on a new supramolecular solvent for spectrophotometric determination of orthophosphate using response surface methodology optimization. J Mol Liq. 2020;297:111768.
Accioni F, García-Gómez D, Rubio S. Exploring polar hydrophobicity in organized media for extracting oligopeptides: application to the extraction of opiorphin in human saliva. J Chromatogr A. 2021;1635:461777.
Durand E, Lecomte J, Villeneuve P. From green chemistry to nature: the versatile role of low transition temperature mixtures. Biochimie 2016;120:119-23.
Zhang Q, De Oliveira Vigier K, Royer S, Jérôme F. Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev. 2012;41:7108-46.
Musarurwa H, Tavengwa NT. Emerging green solvents and their applications during pesticide analysis in food and environmental samples. Talanta 2021;223:121507.
Plotka-Wasylka J, de la Guardia M, Andruch V, Vilková M. Deep eutectic solvents vs ionic liquids: similarities and differences. Microchem J 2020;159:105539.
Makoś P, Słupek E, Gębicki J. Hydrophobic deep eutectic solvents in microextraction techniques-a review. Microchem J. 2020;152:104384.
Li X, Row KH. Development of deep eutectic solvents applied in extraction and separation. J Sep Sci. 2016;39:3505-20.
Farajzadeh MA, Mogaddam MRA, Aghanassab M. Deep eutectic solvent-based dispersive liquid-liquid microextraction. Anal Methods. 2016;8:2576-83.
Zeng H, Qiao K, Li X, Yang M, Zhang S, Lu R, Li J, Gao H, Zhou W. Dispersive liquid-liquid microextraction based on the solidification of deep eutectic solvent for the determination of benzoylureas in environmental water samples. J Sep Sci. 2017;40:4563-70.
Zounr RA, Tuzen M, Khuhawar MY. Ultrasound assisted deep eutectic solvent based on dispersive liquid liquid microextraction of arsenic speciation in water and environmental samples by electrothermal atomic absorption spectrometry. J Mol Liq. 2017;242:441-6.
Farajzadeh MA, Sattari Dabbagh M, Yadeghari A. Deep eutectic solvent based gas-assisted dispersive liquid-phase microextraction combined with gas chromatography and flame ionization detection for the determination of some pesticide residues in fruit and vegetable samples. J Sep Sci. 2017;40:2253-60.
Ge D, Zhang Y, Dai Y, Yang S. Air-assisted dispersive liquid-liquid microextraction based on a new hydrophobic deep eutectic solvent for the preconcentration of benzophenone-type UV filters from aqueous samples. J Sep Sci 2018;41:1635-43.
Ferrone V, Genovese S, Carlucci M, Tiecco M, Germani R, Preziuso F, Epifano F, Carlucci G, Taddeo VA. A green deep eutectic solvent dispersive liquid-liquid micro-extraction (DES-DLLME) for the UHPLC-PDA determination of oxyprenylated phenylpropanoids in olive, soy, peanuts, corn, and sunflower oil. Food Chem. 2018;245:578-85.
Panhwar AH, Tuzen M, Deligonul N, Kazi TG. Ultrasonic assisted deep eutectic solvent liquid-liquid microextraction using azadipyrromethene dye as complexing agent for assessment of chromium species in environmental samples by electrothermal atomic absorption spectrometry. Appl Organomet Chem. 2018;32:1-9.
Altunay N, Elik A, Gürkan R. Monitoring of some trace metals in honeys by flame atomic absorption spectrometry after ultrasound assisted-dispersive liquid liquid microextraction using natural deep eutectic solvent. Microchem J. 2019;147:49-59.
Pacheco-Fernández I, González-Martín R, Silva FAE, Freire MG, Pino V. Insights into coacervative and dispersive liquid-phase microextraction strategies with hydrophilic media-a review. Anal Chim Acta. 2021;1143:225-49.
Shishov A, Chromá R, Vakh C, Kuchár J, Simon A, Andruch V, Bulatov A. In situ decomposition of deep eutectic solvent as a novel approach in liquid-liquid microextraction. Anal Chim Acta. 2019;1065:49-55.
Tomai P, Lippiello A, D'Angelo P, Persson I, Martinelli A, Di Lisio V, Curini R, Fanali C, Gentili A. A low transition temperature mixture for the dispersive liquid-liquid microextraction of pesticides from surface waters. J Chromatogr A. 2019;1605:360329.
Francisco M, Van Den Bruinhorst A, Kroon MC. New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing. Green Chem. 2012;14:2153-7.
Shishov A, Gerasimov A, Nechaeva D, Volodina N, Bessonova E, Bulatov A. An effervescence-assisted dispersive liquid-liquid microextraction based on deep eutectic solvent decomposition: determination of ketoprofen and diclofenac in liver. Microchem J. 2020;156:104837.
Ge D, Gao Y, Cao Y, Dai E, Yuan L. Preparation of a new polymeric deep eutectic solvent and its application in vortex-assisted liquid-liquid microextraction of parabens in foods, cosmetics and pharmaceutical products. J Braz Chem Soc. 2020;31:2120-8.
Soni J, Sahiba N, Sethiya A, Agarwal S. Polyethylene glycol: A promising approach for sustainable organic synthesis. J Mol Liq. 2020;315:113766.
Mogaddam MRA, Farajzadeh MA, Azadmard Damirchi S, Nemati M. Dispersive solid phase extraction combined with solidification of floating organic drop-liquid-liquid microextraction using in situ formation of deep eutectic solvent for extraction of phytosterols from edible oil samples. J Chromatogr A. 2020;1630:461523.
Dil EA, Ghaedi M, Asfaram A, Tayebi L, Mehrabi F. A ferrofluidic hydrophobic deep eutectic solvent for the extraction of doxycycline from urine, blood plasma and milk samples prior to its determination by high-performance liquid chromatography-ultraviolet. J Chromatogr A. 2020;1613:460695.
Jouyban A, Farajzadeh MA, Mogaddam MRA, Nemati M, Alizadeh Nabil AA. Ferrofluid-based dispersive liquid-liquid microextraction using a deep eutectic solvent as a support: applications in the analysis of polycyclic aromatic hydrocarbons in grilled meats. Anal Methods. 2020;12:1522-31.
Masrouri M, Mogaddam MRA, Farajzadeh MA, Nemati M, Lotfipour F. Combination of solvent extraction with deep eutectic solvent based dispersive liquid-liquid microextraction for the analysis of aflatoxin M1 in cheese samples using response surface methodology optimization. J Sep Sci. 2021;44:1501-9.
Hussin SAM, Varanusupakul P, Shahabuddin S, Yih Hui B, Mohamad S. Synthesis and characterization of green menthol-based low transition temperature mixture with tunable thermophysical properties as hydrophobic low viscosity solvent. J Mol Liq. 2020;308:113015.
Sanders JM, Bucher JR, Peckham JC, Kissling GE, Hejtmancik MR, Chhabra RS. Carcinogenesis studies of cresols in rats and mice. Toxicology 2009;257:33-9.
Garcia MT, Kaczerewska O, Ribosa I, Brycki B, Materna P, Drgas M. Biodegradability and aquatic toxicity of quaternary ammonium-based gemini surfactants: Effect of the spacer on their ecological properties. Chemosphere 2016;154:155-60.
Sirisattha S, Momose Y, Kitagawa E, Iwahashi H. Toxicity of anionic detergents determined by Saccharomyces cerevisiae microarray analysis. Water Res. 2004;38:61-70.
Lee MY, Wang WL, Xu ZB, Ye B, Wu QY, Hu HY. The application of UV/PS oxidation for removal of a quaternary ammonium compound of dodecyl trimethyl ammonium chloride (DTAC): the kinetics and mechanism. Sci Total Environ. 2019;655:1261-9.
Atta DY, Negash BM, Yekeen N, Habte AD. A state-of-the-art review on the application of natural surfactants in enhanced oil recovery. J Mol Liq. 2021;321:114888.
Kurpiers M, Wolf JD, Spleis H, Steinbring C, Jörgensen AM, Matuszczak B, Bernkop-Schnürch A. Lysine-based biodegradable surfactants: increasing the lipophilicity of insulin by hydrophobic ion paring. J Pharm Sci. 2021;110:124-34.
Shishov A, Volodina N, Nechaeva D, Gagarinova S, Bulatov A. Deep eutectic solvents as a new kind of dispersive solvent for dispersive liquid-liquid microextraction. RSC Adv. 2018;8:38146-9.
Shishov A, Terno P, Moskvin L, Bulatov A. In-syringe dispersive liquid-liquid microextraction using deep eutectic solvent as disperser: determination of chromium (VI) in beverages. Talanta 2020;206:120209.