Extraction techniques with deep eutectic solvents

Abstract In last years, a plethora of extraction techniques has emerged as environmental-friendly alternatives to conventional extraction procedures. In this particular field, a novel class of solvents known as deep eutectic solvents (DES) has arisen as a new and very promising tool. Compared with conventional organic solvents, DES as well as the so-called natural deep eutectic solvents (NADES) have attracted considerable attention due to the fact that they not only are eco-friendly, non-toxic, and biodegradable organic compounds but also have a low cost, being easy to produce in the own laboratory. The present review provides a critical and organized overview of novel extraction techniques using DES as extracting solvents that were applied in food, biological and environmental sample analysis. An evaluation of how these DES/NADES could improve extraction yields of a variety of analytes and advantages and limitations of each proposal will be discussed and compared with earlier studies.

[1]  T. Kazi,et al.  Deep eutectic solvent based advance microextraction method for determination of aluminum in water and food samples: Multivariate study. , 2018, Talanta.

[2]  M. Soylak,et al.  A simple and novel deep eutectic solvent based ultrasound-assisted emulsification liquid phase microextraction method for malachite green in farmed and ornamental aquarium fish water samples , 2017 .

[3]  Matteo Tiecco,et al.  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. , 2018, Food chemistry.

[4]  Qi Wang,et al.  Deep Eutectic Solvent-Based Microwave-Assisted Method for Extraction of Hydrophilic and Hydrophobic Components from Radix Salviae miltiorrhizae , 2016, Molecules.

[5]  S. Casal,et al.  Polybrominated diphenyl ethers and metabolites – An analytical review on seafood occurrence , 2017 .

[6]  Shijun Shao,et al.  Preparation of a nitro-substituted tris(indolyl)methane modified silica in deep eutectic solvents for solid-phase extraction of organic acids. , 2016, Talanta.

[7]  Robert Verpoorte,et al.  Application of natural deep eutectic solvents to the extraction of anthocyanins from Catharanthus roseus with high extractability and stability replacing conventional organic solvents. , 2016, Journal of chromatography. A.

[8]  M. Soylak,et al.  Deep eutectic solvent based ultrasonic assisted liquid phase microextraction for the FAAS determination of cobalt , 2016 .

[9]  Mladen Brnčić,et al.  Natural deep eutectic solvents and ultrasound-assisted extraction: Green approaches for extraction of wine lees anthocyanins , 2017 .

[10]  Guillermo Rodríguez-Gutiérrez,et al.  Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs). , 2016, Food chemistry.

[11]  K. Ghanemi,et al.  A novel digestion method based on a choline chloride-oxalic acid deep eutectic solvent for determining Cu, Fe, and Zn in fish samples. , 2013, Analytica chimica acta.

[12]  W. Bi,et al.  Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization. , 2013, Journal of chromatography. A.

[13]  B. König,et al.  Low-melting sugar-urea-salt mixtures as solvents for Diels-Alder reactions. , 2005, Chemical communications.

[14]  S. Cunha,et al.  Mycotoxins in cereals and related foodstuffs: A review on occurrence and recent methods of analysis , 2014 .

[15]  Mingliang Zhang,et al.  Utilization of deep eutectic solvents as novel mobile phase additives for improving the separation of bioactive quaternary alkaloids. , 2016, Talanta.

[16]  Geert-Jan Witkamp,et al.  Ionic liquids and deep eutectic solvents in natural products research: mixtures of solids as extraction solvents. , 2013, Journal of natural products.

[17]  M. Gutiérrez,et al.  Resorcinol-Formaldehyde Polycondensation in Deep Eutectic Solvents for the Preparation of Carbons and Carbon−Carbon Nanotube Composites , 2010 .

[18]  Hongdeng Qiu,et al.  Deep eutectic solvents as novel extraction media for phenolic compounds from model oil. , 2014, Chemical communications.

[19]  Heng Zhang,et al.  Deep Eutectic Solvent-Based HS-SME Coupled with GC for the Analysis of Bioactive Terpenoids in Chamaecyparis obtusa Leaves , 2014, Chromatographia.

[20]  L. Corte,et al.  Novel zwitterionic deep eutectic solvents from trimethylglycine and carboxylic acids: characterization of their properties and their toxicity , 2014 .

[21]  Robin D. Rogers,et al.  Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction , 1998 .

[22]  Geert-Jan Witkamp,et al.  Natural deep eutectic solvents as new potential media for green technology. , 2013, Analytica chimica acta.

[23]  L. H. Keith,et al.  Green analytical methodologies. , 2007, Chemical reviews.

[24]  Maaike C. Kroon,et al.  Hydrophobic deep eutectic solvents as water-immiscible extractants , 2015 .

[25]  Weize Wu,et al.  Separation of phenol from model oils with quaternary ammonium salts via forming deep eutectic solvents , 2013 .

[26]  T. Zhu,et al.  Pipette-tip solid-phase extraction based on deep eutectic solvent modified graphene for the determination of sulfamerazine in river water. , 2017, Journal of separation science.

[27]  K. Row,et al.  Recent developments in deep eutectic solvents in chemical sciences , 2013, Monatshefte für Chemie - Chemical Monthly.

[28]  Ping Li,et al.  Deep eutectic solvents as green media for extraction of flavonoid glycosides and aglycones from Platycladi Cacumen , 2017, Journal of pharmaceutical and biomedical analysis.

[29]  K. Ghanemi,et al.  Dissolution of biological samples in deep eutectic solvents: an approach for extraction of polycyclic aromatic hydrocarbons followed by liquid chromatography-fluorescence detection. , 2015, Journal of chromatography. A.

[30]  Emma L. Smith,et al.  Deep eutectic solvents (DESs) and their applications. , 2014, Chemical reviews.

[31]  T. Zhu,et al.  Deep eutectic solvents for the purification of chloromycetin and thiamphenicol from milk. , 2017, Journal of separation science.

[32]  T. Khezeli,et al.  Synthesis and application of magnetic deep eutectic solvents: Novel solvents for ultrasound assisted liquid-liquid microextraction of thiophene. , 2017, Ultrasonics sonochemistry.

[33]  I. Lavilla,et al.  Natural deep eutectic solvents in combination with ultrasonic energy as a green approach for solubilisation of proteins: application to gluten determination by immunoassay. , 2017, Talanta.

[34]  R. Metelka,et al.  Carbon paste electrodes in electroanalytical chemistry , 2009 .

[35]  R. Sahraei,et al.  A green ultrasonic-assisted liquid-liquid microextraction based on deep eutectic solvent for the HPLC-UV determination of ferulic, caffeic and cinnamic acid from olive, almond, sesame and cinnamon oil. , 2016, Talanta.

[36]  Dandan Ge,et al.  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. , 2018, Journal of separation science.

[37]  Marek Tobiszewski,et al.  Green analytical chemistry--theory and practice. , 2010, Chemical Society reviews.

[38]  Tao Wu,et al.  Green and efficient extraction of rutin from tartary buckwheat hull by using natural deep eutectic solvents. , 2017, Food chemistry.

[39]  Sylwia Bajkacz,et al.  Evaluation of new natural deep eutectic solvents for the extraction of isoflavones from soy products. , 2017, Talanta.

[40]  Jacek Namieśnik,et al.  Analytical eco-scale for assessing the greenness of analytical procedures , 2012 .

[41]  K. Row,et al.  Application of deep eutectic solvents in the extraction and separation of target compounds from various samples. , 2015, Journal of separation science.

[42]  Burkhard König,et al.  Low melting mixtures in organic synthesis – an alternative to ionic liquids? , 2012 .

[43]  Q. Wang,et al.  Deep Eutectic Solvents Modified Molecular Imprinted Polymers for Optimized Purification of Chlorogenic Acid from Honeysuckle. , 2015, Journal of chromatographic science.

[44]  Heather D. Bean,et al.  DNA and RNA in anhydrous media: duplex, triplex, and G-quadruplex secondary structures in a deep eutectic solvent. , 2010, Angewandte Chemie.

[45]  Y. Yamini,et al.  Novel generation of deep eutectic solvent as an acceptor phase in three-phase hollow fiber liquid phase microextraction for extraction and preconcentration of steroidal hormones from biological fluids. , 2018, Talanta.

[46]  Y. Choi,et al.  Natural deep eutectic solvents providing enhanced stability of natural colorants from safflower (Carthamus tinctorius). , 2014, Food chemistry.

[47]  M. Gutiérrez,et al.  Freeze-drying of aqueous solutions of deep eutectic solvents: a suitable approach to deep eutectic suspensions of self-assembled structures. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[48]  Francisco Pena-Pereira,et al.  Ionic liquids and deep eutectic mixtures: sustainable solvents for extraction processes. , 2014, ChemSusChem.

[49]  Sanbing Zhang,et al.  Deep eutectic solvent-based ultrasound-assisted dispersive liquid-liquid microextraction coupled with high-performance liquid chromatography for the determination of ultraviolet filters in water samples. , 2017, Journal of chromatography. A.

[50]  P. Anastas,et al.  Green Chemistry , 2018, Environmental Science.

[51]  M. Tomašević,et al.  Green extraction of grape skin phenolics by using deep eutectic solvents. , 2016, Food chemistry.

[52]  Sanbing Zhang,et al.  Dispersive liquid-liquid microextraction based on the solidification of deep eutectic solvent for the determination of benzoylureas in environmental water samples. , 2017, Journal of separation science.

[53]  M. Coelho,et al.  Menthol-based Eutectic Mixtures: Hydrophobic Low Viscosity Solvents , 2015 .

[54]  Raymond K. Rasheed,et al.  Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. , 2001, Chemical communications.

[55]  Raymond K. Rasheed,et al.  Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. , 2004, Journal of the American Chemical Society.

[56]  Alain Walcarius,et al.  Carbon Paste Electrodes in Facts, Numbers, and Notes: A Review on the Occasion of the 50‐Years Jubilee of Carbon Paste in Electrochemistry and Electroanalysis , 2009 .

[57]  J. Coutinho,et al.  Solvatochromic parameters of deep eutectic solvents formed by ammonium-based salts and carboxylic acids. , 2017, Fluid phase equilibria.

[58]  K. Abdi,et al.  Air assisted emulsification liquid-liquid microextraction based on deep eutectic solvent for preconcentration of methadone in water and biological samples. , 2017, Talanta.

[59]  R. Sahraei,et al.  Emulsification liquid-liquid microextraction based on deep eutectic solvent: An extraction method for the determination of benzene, toluene, ethylbenzene and seven polycyclic aromatic hydrocarbons from water samples. , 2015, Journal of chromatography. A.

[60]  S. Cunha,et al.  Current Trends in Liquid-Liquid Microextraction for Analysis of Pesticide Residues in Food and Water , 2011 .

[61]  Lynn F. Gladden,et al.  Glycerol eutectics as sustainable solvent systems , 2010 .

[62]  G. Baker,et al.  New eutectic ionic liquids for lipase activation and enzymatic preparation of biodiesel. , 2011, Organic & biomolecular chemistry.

[63]  David L Davies,et al.  Novel solvent properties of choline chloride/urea mixtures. , 2003, Chemical communications.

[64]  S. Ghorbanian,et al.  Enhanced headspace single drop microextraction method using deep eutectic solvent based magnetic bucky gels: Application to the determination of volatile aromatic hydrocarbons in water and urine samples. , 2018, Journal of separation science.

[65]  T. Kazi,et al.  Ultrasonic assisted dispersive liquid-liquid microextraction method based on deep eutectic solvent for speciation, preconcentration and determination of selenium species (IV) and (VI) in water and food samples. , 2017, Talanta.

[66]  M. Soylak,et al.  Ultrasound assisted-deep eutectic solvent based on emulsification liquid phase microextraction combined with microsample injection flame atomic absorption spectrometry for valence speciation of chromium(III/VI) in environmental samples. , 2016, Talanta.

[67]  I. Arends,et al.  Are Natural Deep Eutectic Solvents the Missing Link in Understanding Cellular Metabolism and Physiology?[W] , 2011, Plant Physiology.

[68]  S. Pandey,et al.  How polar are choline chloride-based deep eutectic solvents? , 2014, Physical chemistry chemical physics : PCCP.

[69]  M. Farajzadeh,et al.  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. , 2017, Journal of separation science.

[70]  François Jérôme,et al.  Deep eutectic solvents: syntheses, properties and applications. , 2012, Chemical Society reviews.

[71]  M. Soylak,et al.  Vortex assisted deep eutectic solvent (DES)-emulsification liquid-liquid microextraction of trace curcumin in food and herbal tea samples. , 2018, Food chemistry.

[72]  Y. Yamini,et al.  Developments in hollow fiber based liquid-phase microextraction: principles and applications , 2012, Microchimica Acta.