Application of solid-phase extraction for trace elements in environmental and biological samples: a review.

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Application of Solid-Phase Extraction for Trace Elements in Environmental and Biological Samples: A Review ab

a

a

Wan Aini Wan Ibrahim , Layth Imad Abd Ali , Azli Sulaiman , Mohd. Marsin Sanagi

abc

&

d

Hassan Y. Aboul-Enein a

Separation Science and Technology Group (SepSTec), Department of Chemistry, Faculty of ScienceUniversiti Teknologi Malaysia, Johor Bahru, Malaysia b

Nanotechnology Research Alliance, Universiti Teknologi Malaysia, Johor Bahru, Malaysia

c

Ibnu Sina Institute of Fundamental Science Studies, Universiti Teknologi Malaysia, Johor Bahru, Malaysia d

Department of Pharmaceutical and Medicinal ChemistryPharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo, Egypt Published online: 01 Apr 2014.

To cite this article: Wan Aini Wan Ibrahim, Layth Imad Abd Ali, Azli Sulaiman, Mohd. Marsin Sanagi & Hassan Y. Aboul-Enein (2014) Application of Solid-Phase Extraction for Trace Elements in Environmental and Biological Samples: A Review, Critical Reviews in Analytical Chemistry, 44:3, 233-254, DOI: 10.1080/10408347.2013.855607 To link to this article: http://dx.doi.org/10.1080/10408347.2013.855607

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Critical Reviews in Analytical Chemistry, 44:233–254, 2014 c Taylor and Francis Group, LLC Copyright ISSN: 1040-8347 print / 1547-6510 online DOI: 10.1080/10408347.2013.855607

Application of Solid-Phase Extraction for Trace Elements in Environmental and Biological Samples: A Review Wan Aini Wan Ibrahim,1,2 Layth Imad Abd Ali,1 Azli Sulaiman,1 Mohd. Marsin Sanagi,1,2,3 and Hassan Y. Aboul-Enein4

Downloaded by [University Of Maryland] at 03:47 04 May 2014

1

Separation Science and Technology Group (SepSTec), Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru, Malaysia 2 Nanotechnology Research Alliance, Universiti Teknologi Malaysia, Johor Bahru, Malaysia 3 Ibnu Sina Institute of Fundamental Science Studies, Universiti Teknologi Malaysia, Johor Bahru, Malaysia 4 Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo, Egypt

The progress of novel sorbents and their function in preconcentration techniques for determination of trace elements is a topic of great importance. This review discusses numerous analytical approaches including the preparation and practice of unique modification of solid-phase materials. The performance and main features of ion-imprinting polymers, carbon nanotubes, biosorbents, and nanoparticles are described, covering the period 2007–2012. The perspective and future developments in the use of these materials are illustrated. Keywords Metal ions, novel sorbents, preconcentration techniques, solid-phase extraction

INTRODUCTION In recent years, the topics of preconcentration, separation, and determination of trace concentration of metals ions and organic species in environmental and biological samples have gained interest (Brown and Milton, 2005; Bruzzoniti et al., 2000; Jin et al., 2012; Schlosser et al., 2005). The first limitation in analytical methods for determining trace metals is finding another species in the matrix samples as interferent(s) (Jacek, 2002), which may result in less sensitivity of analytical techniques. Many developments have been applied to the techniques in order to solve these problems depending on the nature of the samples, such as co-precipitation (Atanassova et al., 1998; Minamisawa et al., 2004; Sahin et al., 2005; Sato and Ueda, 2001; Zhang et al., 2001), adsorption (Dey and Airoldi, 2008; Dey et al., 2009; Dumrul et al., 2011; Fan et al., 2011; Hatay et al., 2008;

Address correspondence to W. A. Wan Ibrahim, Separation Science and Technology Group (SepSTec), Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia. E-mail: [email protected], [email protected], or H. Y. Aboul-Enein, Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo 12311, Egypt. E-mail: [email protected]

Li et al., 2010; Puanngam and Unob, 2008; Quétel et al., 2010; Skorik, 2012; Zhang, 2011; Zhang et al., 2012a), ion-exchange (Akieh et al., 2008; Fang and Welz, 1989; Mahmoud et al., 2010b), cloud point (Bezerra et al., 2005, 2006; Donati et al., 2006; Ghaedi et al., 2008; Lemos et al., 2007), liquid-liquid extraction (El Hussaini and Rice, 2004; Fathi et al., 2008; Jain et al., 2005), and solid-phase extraction (Pichon, 2000; Türker, 2007). In this review we are interested in solid-phase extraction (SPE) because this method has been recognized as more active and rapid for separation, with high selectivity for solid sorbents (Fan et al., 2012), safe procedures, low economic cost and small use of organic solvents, simple extraction, high recovery and preconcentration factor (Faraji et al., in press), and automation with more detection techniques. Various studies (Augusto et al., 2010; Türker, 2012) have been reported using solid sorbent and detection methods such as atomic absorption spectrometry (Ghaedi and Niknam, 2010; Khajeh et al., 2011; Kumar et al., 2011; Mahmoud et al., 2010b; Pourreza and Ghanemi, 2009; Topuz and Macit, 2011; Tuzen et al., 2006; Yang et al., 2009), atomic fluorescence (Li et al., 2009; Zhang et al., 2010c), inductively coupled plasma optical emission spectrometer (Das et al., 2012a; Kalal et al., 2011; Menegário et al., 2006), spectrophotometry (Huang et al., 2009; Totur et al., 2012), chemiluminescence (Meng et al., 2011; Su et al., 2007; Xu et al., 2012), voltammetry (Du et al., 2008;

233


234

W. A. WAN IBRAHIM ET AL.

Gong et al., 2010), and infrared spectroscopy (Quétel et al., 2010; Zheng et al., 2011). Several conditions are required for using an SPE sorbent as a powerful extraction material such as a broad range of applied pH, high elution efficiently, large capacity, and reactiveness. Recently, the importance of the SPE method has increased because numerous materials can be used as sorbents, for example, activated carbon (Pyrzynska, 2007), metal oxides (Hua et al., 2012), chelating resin (Pina-Luis et al., 2012), modified or bonded silica (Jal et al., 2004; Sharma et al., 2003), wool (Monasterio and Wuilloud, 2009), cotton (Faraji et al., 2009), cellulose (Akama et al., 2003; Soylak et al., 2010), and polyurethane foam (Burham, 2009). Various modern applications for SPE of trace elements and organic species analysis in environmental and biological samples are discussed in this review. Furthermore, novel sorbents for extracting an analyte in solution using several techniques are described and discussed. SORBENTS Ion-Imprinted Polymers The first challenge in applying SPE using ordinary fixed phase is the decrease of selectivity in the retention process. Methods for planning of the solid phase depend on the ion-selective imprinting that has been used for selective separation and preconcentration of trace metals. Ion imprinting is a procedure for the preparation of a polymer containing specific characterization (Rao et al., 2006). Three stages of ion-imprinting polymer (IIP) preparation are shown in Figure 1, which includes (a) complex reaction between metal ions

FIG. 1. Scheme for the general synthesis of IIPs.

(template) with ligand (complexation), (b) the polymer process of this complex (polymerization), and (c) elimination of metal ion after copolymerization. An ion-imprinted polymer (IIP) is a macroporous material with a three-dimensional figure corresponding in both form and chemical functionality to the template (Rao et al., 2004). The selectivity of an IIP increases because the polymer is prepared in the presence of a template ion and a functional monomer. The selectivity of a polymeric adsorbent also depends on the types of ligands, the coordination geometry, and coordination number of the ions and their charges and sizes. Therefore, an IIP is able to identify the template from other components in a sample (Fan et al., 2012; Li and Sun, 2007). The selectivity of an IIP is very important when analyzing a sample matrix. Ion-imprinted polymers show suitable thermal and chemical stability, and without loss of activity. Furthermore, they possess high retention capacity, toughness to heat and pressure, high mechanical strength, and ability to be used under harsh chemical media. The main IIP application as solid phase for preconcentration of metal ion is because of its low cost, flexibility, and environmentally friendliness (Kala et al., 2004). A number of designer ion-imprinted polymers have been synthesized on binary or ternary complexes of various imprinting ions (Ahmadi et al., 2010; James et al., 2009; Shirvani-Arani et al., 2008). Many examples have been published using IIP techniques for enhanced metal ions from solutions with high selectivity. Cu(II)-imprinted poly(ethylene glycol dimethacrylatemethacryloylamidohistidine micro beads with an average size of 150–200 μm were prepared by dispersion polymerization, and these features made the imprinted micro beads very good candidates for selective removal of Cu(II) ions at high adsorption capacity. The detection limit was increased at least 1000fold with the preconcentration approach using imprinted micro beads. The method was also applied to certified reference and seawater samples (Say et al., 2003). Likewise, a new chelating resin (poly-Cd(II)-DAAB-VP) was prepared by the metal ion-imprinted polymer (MIIP) method. The resin was synthesized by a one-pot reaction of Cd(II)-diazoaminobenzene-vinylpyridine with cross-linker ethylene-glycoldimethacrylate (EGDMA). Compared with a non-imprinted resin, the poly-Cd(II)-DAAB-VP has higher adsorption capacity and selectivity for Cd(II). The distribution ratio (D) values for the Cd(II)-imprinted resin increase for Cd(II) with respect to D values of Zn(II), Cu(II), and Hg(II) and nonimprinted resin. Acceptable Cd(II) determination in natural water samples by flame atomic absorption spectrometry (FAAS) (Liu et al., 2004) was observed. Singh and Mishra (2009a) studied Cd(II) extraction and also extraction of UO2 + ions (Sadeghi and Mofrad, 2008; Singh and Mishra, 2009b) using IIP with success. A unique IIP material was synthesized by copolymerization of palladium-iodide-vinyl pyridinium/palladium-thiocyanatevinyl pyridinium ion ternary ion-association complex taken in methanol/DMSO with 2-hydroxyethyl methacrylate (functional


SPE FOR TRACE ELEMENTS

monomer) and ethylene glycol dimethacrylate (cross-linking monomer) in the presence of 2, 2 -azobisiso-butryonitrile (initiator). On-line flow injection-flame atomic absorption spectrometry (FI-FAAS) offers higher enrichment factor and better precision and can analyze more samples for a given time than the batch method. This procedure is desirable for the analysis of palladium current in the street/fan blade dust samples collected from busy cities of India, and the values obtained were compared with the standard inductively coupled plasma-mass spectrometry (ICP-MS) values (Daniel et al., 2006). Palladium (II) IIP materials were also prepared via bulk, precipitation, and suspension polymerization methods. The selectivity of the IIP is in the order bulk ∼ precipitation > suspension (Daniel et al., 2005). Methyl mercury–imprinted and non-imprinted polymers were prepared by the formation of a monomer complex of methyl mercury with (4-ethenylphenyl)-4-formate-6-phenyl2,2 -bipyridine and thermally polymerized with divinylbenzene (cross-linker) in the presence of 2,2 -azobisisobutyronitrile as initiator and subsequently leached with the acidic thiourea solution. The determination of methyl mercury in human hair sample was achieved by cold vapor atomic absorption spectrometry (CVAAS) (Liu et al., 2006). Metal IIP beads were successfully used for the speciation of mercury in river and mineral waters. They were prepared by copolymerization of methacrylic acid as monomer, trimethylpropane trimethacrylate as cross-linking agent, and 2,2 -azobisisobutyronitrile as initiator in the presence of Hg(II)1-(2-thiazolylazo)-2-naphthol complex (Dakova et al., 2009). The limit of detection for inorganic mercury as determined by CVAAS was 0.006 μg L−1 with good RSD (5–9%). A bi-functionalized 5-vinyl-8-hydroxyquinoline as monomer was successfully used for IIP for nickel recognition with higher selectivity than 8-hydroxyquinoline (Otero-Roman´ı et al., 2009). The IIP was prepared by precipitation polymerization. The limit of detection at 0.26 μg L−1 was achieved for Ni(II) ions from seawater before inductively coupled plasma optical emission spectrometry analysis. Specific examples of the preconcentration technique with ion-imprinted polymers are shown in Table 1.

Carbon Nanotubes Carbon nanotube (CNT) structure was first designated by Iijima (1991). Since then there have been many studies on CNT because of its unique chemical and physical properties. A carbon nanotube can be imagined as a sheet of graphite that has been curved into a tube; CNTs are classified into single-walled carbon nanotubes (SWCNTs) and multiwalled carbon nanotubes (MWCNTs) according to the carbon atom shells in the wall of the nanotubes (Figure 2) (Ren et al., 2011). MWCNTs consist of numerous tens of graphitic shells defining a hole, typically from 2 to 25 nm, split by a space of about 0.34 nm (Rubianes and Rivas, 2003) (Figure 2(a)). SWCNTs involve one layer of

235

FIG. 2. Two (Super) structure representations of (a) MW-CNTs and (b) SW-CNTs (Ren et al., 2011) © Elsevier. Reproduced by permission of Elsevier. Permission to reuse must be obtained from the rightsholder. hexagonal graphite lattice curved to form a continuous cylinder with a radius of up to a few nanometers (Figure 2(b)). CNTs have specific properties, such as chemical stability, high electrical conductivity, high thermal stability, mechanical strength, and large specific surface area (Vuković et al., 2010, 2011), signifying potential for several applications (HerreraHerrera et al., 2012). The advantage of using CNTs in chemical analysis as adsorbent materials, especially in SPE as new solid sorbent compounds, stems from the fact that the CNT surface consists of hexagonal arrays of carbon atoms in graphite shells, which are capable of a strong interaction with other molecules or atoms (Pan et al., 2005; Pyrzynska, 2010a, 2010b). Furthermore, these surfaces can be modified by presenting numerous organic functional groups, thus supplying a powerful physical sorbing surface area, adjustable surface charge, and a source of protons for chemical ionization. It has been validated that the surfaces of CNTs can be easily modified by various techniques (Sitko et al., 2012). All the evidence stated before reveals that CNTs, and particularly multiwalled carbon nanotubes, have unique analytical potential as active SPE adsorbent for chelates or ion pairs of metal ions, organic compounds, and organometallic compounds (Ravelo-Pérez et al., 2010). For example, novel modified MWCNTs have been used for the determination of morphine and diclofenac in biological and pharmaceutical samples by voltammetric measurement (Mokhtari et al., 2012). Another method has been developed for determination of isoniazid in urine samples, by fabricating MWNT-C18 sorbent for SPE and using electrochemiluminescence (ECL) analysis of this composite (Guo et al., 2009b). A new application for MWCNT-coated quartz wool (MWCNT/QW) prepared by dynamic layer-by-layer

236

Cd(II)

Pd(II)

Hg(II) Pb(II)

Ni(II)

Nd(III)

Fe(III)

Th(IV)

Ni(II)

Zn(II)

Cd(II)

Cu(II)

UO2 2+

Analyte

2-Nitrophenyloctyl ether and polyvinyl chloride Methacrylic acid and trimethylolpropane trimethacrylate Ethylenediamine and pentaerythritol triacrylate 8-Acryloyloxyquinoline and ethylene glycol dimethacrylate 4-Vinylpyridine and divinylbenzene N-(o-carboxyphenyl) maleamic acid and silica gel Silica gel and 3-minopropyltri-methoxy silane 5,7-Dichloroquinoline-8-ol4-vinylpyridine and styrene and divinyl benzene 4-Vinylpyridine and ethyleneglycol dimethacrylate Methacrylic acid and 4-vinylpyridine, ethyleneglycol dimethacrylate, 2,2 -azobisisobutyronirile 4-Vinylpyridine and styrene and divinylbenzene Ethylene glycol dimethacrylate and co-vinylimidazole

Reagent for polymer preparation

FAAS

FAAS

VGA-AAS and GTA-GFAAS

FAAS

ICP-AES

ICP-AES

ICP-OES

ET-AAS

FAAS

ICP-OES

FAAS

Potentiometric sensor

Detection method

38.4

33

— —

—

—

75

125

100

37.8

200

250

—

Preconcentration factor

0.11

5

2.875 0.092

1.6

6.1

0.34

0.51

0.050

0.65

0.14

0.063

4.05

D.L.(μg/L)

Types of water sample, urine

Water sample

Water sample Water sample

Water sample

Synthetic samples

Plants and water

Synthetic samples

Water samples

Synthetic samples

Water sample

Seawater

Water sample

Sample

TABLE 1 Some applications of ion-imprinted polymer (IIP) for preconcentration and determination of metal ions


˙ Godlewska-Zyłkiewicz et al., 2010 Segatelli et al., 2010

Singh and Mishra, 2010a Khajeh et al., 2011

Saraji and Yousefi, 2009

Guo et al., 2009a

Chang et al., 2007

Otero-Roman´ı et al., 2008 He et al., 2007

Zhao et al., 2007

Zhai et al., 2007

Dakova et al., 2007

Metilda et al., 2007

Reference

237

2-Hydroxy ethyl methacrylate and ethylene glycol dimethacrylate 1-Phenyl-3-methylthio-4cyano-5-amino-pyrazole and silica gel Methyl methacrylate and ethyleneglycol dimethacrylate 1,4-Dihydroxy-9,10anthraquinone and ethyleneglycol dimethacrylate Thiosemicarbazide and acetaldehyde thiosemicarbazone and methacrylic acid ethylene glycol dimethacrylate 1-Vinylimidazole and 4-vinylpyridine and styrene Styrene and divinyl benzene Styrene and ethylene glycol dimethacrylate Methacrylic acid and ethylene glycol dimethacrylate Methyl methacrylate and ethyleneglycol dimethacrylate FAAS

GFAAS

FI-FAAS FAAS

ICP-MS

ETAAS

ICP-AES

—

20

74 28 and 118

25

3–4

18.4

—

20.2

UV-vis spectrophotometer ETAAS

—

GTA-AAS

0.26

0.32

0.4 1.02 and 0.48

0.025

Ru-TSd = 0.16 Ru-AcTSn = 0.25

0.3

0.02

0.43

6

Zambrzycka et al., 2011

Shamspur and Besharati-Seidani, 2011

Arbab-Zavar et al., 2011

Lin et al., 2010

Singh and Mishra, 2010b

Natural and water samples

Environmental samples

˙ Godlewska-Zylkiewicz et al., 2012 Xie et al., 2012

Environmental water Tsoi et al., 2012 samples Water samples Tobiasz et al., 2012 Natural water and cereal Shakerian et al., 2012

Water samples, sludge, grass, and human hair

Water sample

Real sample

Biological and water samples

Seawater sample

CVAAS: cold vapor atomic absorption spectrometry; D.L.: detection limit; ETAAS: electrothermal atomic absorption spectrometry; FAAS: flame atomic absorption spectrometry; FI-FAAS: flow injection-flame atomic absorption spectrometry; GFAAS: graphite furnace atomic absorption spectrometry; GTA-AAS: graphite tube atomizer-atomic absorption spectrometer; ICP-AES: inductively coupled plasma-atomic emission spectrometry; ICP-MS: inductively coupled plasma-mass spectrometry; ICP-OES: inductively coupled plasma-optical emission spectrometry; VGA-AAS: vapor generation accessory-atomic absorption spectrometry.

Fe(III)

Ru(III)

Cu(II) Zn(II)

As(V)

Ru(III)

Cu(II)

Tl(III)

Th(IV)

Ni(II)



238


self-assembly was as SPE absorbent for on-line separation and preconcentration of lysozyme in egg white with a flow system operated by a sequential injection (SI) system (Du et al., 2012). The proposed method was validated successfully for the extraction of dissolved organic matter (DOM) from seawater by functioning MWCNTs as solid sorbent with size exclusion chromatography (SEC) by UV detection (Sánchez-González et al., 2012). A rapid, sensitive, and cost-effective method for the analysis of phthalate acid esters (PAEs) from beverage and environmental water samples was established by Luo et al. (2012). This method uses magnetic CNTs prepared by mixing magnetic particles and MWCNTs in the extraction of analytes and their analysis using gas chromatography-mass spectrometry (GC-MS). Many functional MWCNTs have been reported for determination of herbicides and pesticides in environmental and real samples. A novel, simple, cost-effective, and sensitive method was developed for the determination of atrazine and its principal metabolites, namely deisopropyl-atrazine (DIA) and deethylatrazine (DEA), in water and soil samples using MWCNTs as SPE adsorbents in common with GC-MS (Min et al., 2008). Similarly, a sensitive and selective preconcentration method using an SPE disk, namely a MWCNTs disk, was proposed for the determination of atrazine and simazine in water samples. Atrazine and simazine were extracted on a MWCNTs disk and then determined by GC-MS (Katsumata et al., 2010). Moreover, a MWCNT-poly (acrylamide) nano composite film modified glassy carbon electrode (MWCNT-PAAM/GCE) proved to be a suitable sensing tool for the fast, sensitive, and selective determination of methyl parathion in environmental water samples by using a sensitive electrochemical differential pulse voltammetry as a detection method (Zeng et al., 2012). The extraction of inorganic species is also possible with the use of CNTs. For example, a novel method has been established for the determination of trace rare earth elements (REEs) in water samples based on preconcentration with a micro-column packed with MWCNTs before their determination by inductively coupled plasma-atomic emission spectrometry (ICP-AES). The method was validated using a certified reference material and has been successfully applied for the determination of trace REEs in lake water and synthetic seawater with satisfactory results (Liang et al., 2005). Furthermore, the effect of oxidation of activated carbon (AC) with various oxidizing agents (nitric acid, hydrogen peroxide, ammonium persulfate) on preconcentration of metal ions (Cr3+, Mn2+, Pb2+, Cu2+, Cd2+, and Zn2+) from environmental waters prior to their FAAS analysis was investigated. The analytical performance of the preconcentration method using AC treated with nitric acid (AC-NA) was close to that of MWCNT-NA, but AC-NA was better than nonoxidized MWCNT. Application of the optimized preconcentration method (using AC-NA sorbent) to environmental waters (tap water, reservoir water, stream water) gave spike recoveries of the metals in the range 63–104% (El-Sheikh, 2008). In addition, functionalized MWCNTs have been applied as adsorptive membrane for Cu(II) removal from

water samples (Salehi et al., 2012). Thus, analytical preconcentration and separation techniques using MWCNTs can be employed for metal determination. Some of the methods for determination of metals using MWCNTs are summarized in Table 2. Various publications discussed the use of SWCNTs as solid extractor metal ions. A novel method using a micro column packed with SWCNTs as a novel adsorption material improved the preconcentration of trace Cu, Co, and Pb in environmental and biological samples before their determination by ICP-MS. The limits of detection for Cu, Co, and Pb were 39, 1.2, and 5.4 pg mL−1 respectively (Chen et al., 2009). Likewise, a preconcentration-separation procedure has been recognized based on SPE of Fe(III) and Cr(III) on a SWCNT disk. The detection limits for iron and chromium were 2.12 and 4.08 μg L−1, respectively, by using AAS, and the method was successfully applied to the preconcentration and separation of iron and chromium in some food and herbal plant samples from Turkey (Soylak and Unsal, 2010). Similarly, a new method was established for the simultaneous speciation of inorganic arsenic and antimony in water by on-line SPE coupled with hydride generation-double channelatomic fluorescence spectrometry (HG-DC-AFS). The preconcentration factors were found to be 25.4 for As(III) and 24.6 for Sb(III), with the detection limits of 3.8 ng L−1 for As(III) and 2.1 ng L−1 for Sb(III), and the method was validated for the speciation of inorganic As and Sb in natural water samples (Wu et al., 2011). Biosorbents The functionality of biological material to collect trace metals has been identified in recent years. However, lately, several investigations and great interest have been focused on the use of biological species for preconcentration techniques (Das, 2010; Mack et al., 2007). The biosorption is based on the metalbinding capacities of various biological materials (Wang and Chen, 2009). Sorbents applied in ordinarily separation and preconcentration methods usually possess only one type of binding site. The benefit of biosorption is that potentially the cell wall is composed of polysaccharide complexed with proteins, lipids, and other substances, containing many active sites that can be involved in metal binding such as carboxyl, hydroxyl, sulfate, phosphate, amino groups, and others. The biosorption system depends on the physicochemical interaction between the charged groups of the microorganisms and ions in solution, in which living (with biological activity) as well as dead organisms (without biological activity) can be used, which probably takes place by means of an ion-exchange method. Biosorbents are used in procedures that required column materials that can withstand recurrent use (Farooq et al., 2010). A variation of nonliving biomaterials can be operated to extract metal ions from the environment and biological samples (Areco et al., 2012; Das et al., 2012b). Free cells are ordinarily used in biosorption research. But the application of free microorganism sources produces comparatively low accuracy

239



TABLE 2 Some of the methods for metal ion separation and preconcentration using MWCNTs Analyte

D.L. (μgL−1)

E.F.

Detection technique

Cd(II) Cr(VI) Cu(II) Pb(II)

0.15 0.9 0.32 2.6

— — — 44.2

FAAS AAS FAAS FAAS

Cd(II) Pb(II) Cu(II) Zn(II) MnO4 − Cu(II) Au(III) Cu(II) Cd(II) Pb(II) Zn(II) Cr(III) Fe(III) Pb(II) Au(III) Mn(II) Cu(II) Co(II) Ni(II) Cu(II) Rh(III) Cu(II) Ni(II) Co(II) As(V) Fe(III) Cu(II) Mn(II) Pb(II) Cd(II) Ga(III) Rh(III) Au(III) Cd(II) Ni(II) Pb(II) Hg(II) Cu(II) Ni(II)

0.15 0.278 0.465 0.867 0.709 2.1 0.15 0.3 0.45 0.6 0.35 0.24 0.19 0.33 0.03 0.01 1.64 5.31 5.68 1.46 0.01 0.31 0.63 0.05 0.002 4.9 6.5 3.5 8 1.03 3.03 0.01 < 0.041 0.01 0.03 0.01 0.0123 50 40

31.5 —

12 75 80

Sample

Reference Xiao et al., 2007a Tuzen and Soylak, 2007 Xiao et al., 2007b Barbosa et al., 2007

FAAS AAS

Environmental water samples Water samples Environment Water samples and common medicinal herbs Water samples Water samples

AAS FAAS FAAS

Water samples Geological and water samples Food and environmental samples

Stafiej and Pyrzynska, 2008 Liang et al., 2008 Tuzen et al., 2008a

200

ICP-OES

Biological and natural water samples

Zang et al., 2009

250

FAAS

Water and standard samples

40

FAAS


Shamspur and Mostafavi, 2009 Duran et al., 2009

60 120 29 28 180 — 20

FAAS FAAS FAAS

Environmental samples Aqueous solution Environmental and biological materials Metals in natural water Real water samples Food and environmental samples

Soylak and Ercan, 2009 Ghaseminezhad et al., 2009 Liu et al., 2009

Environmental samples Fly ash samples Aqueous solution Environmental samples Serum protein Solid samples (sediments and sludges) Water samples Wastewater and real water sample

Parodi et al., 2011 Zhang et al., 2010c Ghaseminezhad et al., 2009 Ebrahimzadeh et al., 2013 Acosta et al., 2013 Savio et al., 2011

120 43 120 244 40 38 40 30 25

FAAS AFS FAAS

USN-ICP-OES FAAS FAAS FAAS ETAAS ETAAS CVAAS FAAS

Corazza et al., 2012 El-Sheikh et al., 2007

Pacheco et al., 2009 Li et al., 2009 Ozcan et al., 2010

El-Sheikh et al., 2011b Vellaichamy and Palanivelu, 2011 (Continued on next page)

240


TABLE 2 Some of the methods for metal ion separation and preconcentration using MWCNTs (Continued)


Analyte Zn(II) As(III) As(V) Sb(III) Sb(V) Pb(II) Cd(II) Cd(II) Pb(II) Mn(II) V(V) Cr(VI) Cu(II) As(V)

D.L. (μgL−1) 60 0.02 0.05

0.0044 0.0015 0.3 1 0.058 0.0021 0.0038 0.0035 0.0013 0.0036

E.F.

Detection technique

250

ETAAS

Water samples

López-Garc´ıa et al., 2011

100

ETAAS

Real water samples

Yang et al., 2011

282 304 100 111 95 60 52 128

FAAS FAAS

Environmental samples Standard alloys and water samples Herring, spinach, river water, and tap water

Nabid et al., 2012 Afzali et al., 2012

ICP-MS

Sample

Reference

Dai et al., 2012

AAS: atomic absorption spectrometry; AFS: atomic fluorescence spectrometry; CVAAS: cold vapor atomic absorption spectrometry; E.F.: enrichment factor; ETAAS: electrothermal atomic absorption spectrometry; FAAS: flame atomic absorption spectrometry; ICP-MS: inductively coupled plasma-mass spectrometry; ICP-OES: inductively coupled plasma-optical emission spectrometry; USN-ICP-OES: ultrasonic nebulization-inductively coupled plasma-optical emission spectrometry.

results. Thus, in this procedure, there are limitations to the lower ability of the biomass to regenerate and/or be reused. Alternatively, the use of immobilized cells of bacteria, fungi, and yeast on suitable supports for preconcentration and determination of numerous heavy metal ions has been recently validated (Areco et al., 2012) (Figure 3). Many advantages were seen with biosorption by microorganisms immobilized on a solid support,

FIG. 3. Distribution of microorganisms (MOs) employed as biosorbents for analytical purposes (Pacheco et al., 2011. © Elsevier. Reproduced by permission of Elsevier. Permission to reuse must be obtained from the rightsholder).

such as high efficiency for preconcentration, simplicity, low cost, high recovery, and environmental friendliness (Pacheco et al., 2011). Microorganisms can involve a large interaction limit with metal ions because of their small size and high surface-areato-volume ratio. Various supports, e.g., silica gel (Akar et al., 2009), glass beads (Shriver-Lake et al., 2002), sepiolite (Ba˘g et al., 2000), polyurethane (Menegário et al., 2006), nanoparticles (Mahmoud et al., 2012), and XAD resin series resins (Kocaoba and Arisoy, 2011), have been applied to immobilize biomaterials either by adsorption or physical entrapment. Table 3 summarizes the characteristics of preconcentration techniques with solid supports connected to biomaterials. Nanoparticles In recent years, many features have been defined for the structures and functions of nanoparticles (NPs). Likewise, numerous applications for NPs have been found in several fields, such as biomedicine, bioseparation, and wastewater treatment (BlancoAndujar et al., 2010; Hua et al., 2012). The nanometer-sized material components of clusters of atoms or molecules of metal oxides, NPs have a size range from 1 to about 100 nm. Nanoparticles possess a large number of unsaturated atoms on their surface, which can interact with different atoms through interactive forces. Furthermore, these nanoparticles have the ability to act as efficient adsorbent and selective agents to metal ions. Several types of nanometer-sized metal oxides, such as

241

Dowex optipore V-493

Bacillus thuringiensis israelensis

Sepabeads SP 70

MWCNTs

Chromo-sorb 106

Pseudomonas aeruginosa Penicillium italicum

Pseudomonas aeruginosa

—

Saccharomyces cerevisiae

Chromo- sorb 101

Cu(II) Cd(II) Pb(II) Mn(II) Fe(III) Ni(II) Co(II) Cd(II) Pb(II) Mn(II) Cr(III) Ni(II) Co(II) Cd(II) Pb(II) Mn(II) Cr(III) Ni(II) Cu(II) Fe(III) Zn(II)

Diaion SP-850

Bacillus sphaericus

Bacillus thuringiensis var. israelensis

Al(III)

Pumice stone

Penicillium digitatum

Cu(II) Zn(II) Pb(II) Cu(II) Pb(II) Fe(II) Co(II) Sb(III) Sb(V)

CPG Cellex-T

Baker’s yeasts Chlorella vulgaris

Cu(II) Cd(II) Mo(VI) Pt(IV)

Analyte

Amberlite XAD-4

Support

Bacillus subtilis

Biomaterials

1.29 0.41 2.70 0.55 1.60 1.33 1.43 0.37 2.85 0.71 1.15 1.67 0.74 0.24 2.60 0.43 1.18 1.30 1.14 2.01 0.14

1.8 1.3 5.8 0.20 0.75 0.25 0.30 0.002 0.005 7 0.9 0.03

1.81 0.012 0.021 0.057

D.L. (μg/L)

37

50

31

25

50

9

50

50

50 50 480 —


FAAS

FAAS

FASS

FAAS

GFAAS

ICP-MS ICP-OES

FAAS

FAAS

FI-USN-ICP OES FI-CL

FAAS

Detection technique

Marcellino et al., 2008

Tuzen et al., 2007b

Gil et al., 2007 ˙ Godlewska-Zylkiewicz et al., 2007 Baytak et al., 2008

Dogru et al., 2007

Reference

Tuzen et al., 2008b

Mendil et al., 2008b

Mendil et al., 2008a

Multivitamin-multimineral Tuzen et al., 2008c tablet, dialysis solutions, natural water, and some food samples (Continued on next page)

Tomato leaves, bovine liver, boiled wheat, canned fish, black tea, lichen, and spring, snow and tap water samples

Red wine, rice, canned fish, seawater, spring water, urine samples

Natural water, mushroom, lichen, moss, refined table salt samples

Natural water and food samples Tuzen and Soylak, 2008

Water

Tea, mushroom, boiled wheat, rice, and soil


Water Environmental samples

Water

Sample

TABLE 3 Some examples of metal ion preconcentration by solid-phase extraction with solid support immobilized biomaterials


242 —

Alizarin fluorine blue Diaion HP-2MG resin —

Cellex-T

— —

As(III) AS(V) Cr(III)

Pt(IV) Pd(II) Cr(III) Cr(VI) Cu(II)

As(III) As(V) Cd(II) Ag(I) Pb(II) Pt(IV) Cu(II) Cr(III) Cu(II) Fe(III) Mn(II) Ni(II) Zn(II) Cr(III) Cs(I)

Cd(II) Cu(II) Cd(II) Zn(II) Hg(II) MeHg

Analyte

0.08

0.011

0.020 0.012 1.92 2.45 0.018

5.50 0.22 0.78 0.1 0.8 0.17 0.45 0.25 0.15 0.33 0.10 1.58 3.9

1.7 0.042 0.172 0.076 0.0021 0.0015

D.L. (μg/L)

—

35

75

9.7 11.5 —

— 50

— 35 868 — 18 250

25

32 11

Preconcentration factor Fuel alcohol Environmental water

Sample

Tobacco leaf samples

Water

Road dust samples

Water and tobacco leaves Water

Alcohol fuel Water Water Environmental samples Food samples Water

Hydride generation Water, food, and biological AAS samples FAAS Aqueous solution

FAAS

FAAS

ETAAS

FAAS FAAS

FAAS FAAS FAAS FI-CL FASS ICP-AES

CVAAS Natural water, environmental Hydride generation samples AAS Natural water and food

FAAS FAAS

Detection technique

Dittert et al., 2012

Tuzen et al., 2010

Dias et al., 2012

Woińska and ˙ Godlewska- Zylkiewicz, 2011 Alves and Coelho, 2013

El-Sheikh et al., 2011a Mao et al., 2011

Alves et al., 2010 Araújo et al., 2010 Bakircioglu et al., 2010 Malejko et al., 2010 Xiang et al., 2010 Baytak et al., 2011

Uluozlu et al., 2010

Tuzen et al., 2009

Bianchin et al., 2009 El-Sheikh et al., 2009

Reference

CVAAS: cold vapor atomic absorption spectrometry; ETAAS: electrothermal atomic absorption spectrometry; FAAS: flame atomic absorption spectrometry; FI-CL: flow injectionchemiluminescence; FI-USN-ICP-OES: flow injection and ultrasonic nebulization with inductively coupled plasma-optical emission spectrometry; GFAAS: graphite furnace atomic absorption spectrometry; HGAAS: hydride generation atomic absorption spectrometry; HG-AFS: hydride generation-atomic fluorescence spectrometry; ICP-AES: inductively coupled plasma-atomic emission spectrometry; ICP-MS: inductively coupled plasma-mass spectrometry; ICP-OES: inductively coupled plasma-optical emission spectrometry.

Laminaria seaweed

Alternaria solani

Agave sisalana

Moringa oleifera

Olive pomace (OP) Pseudomonas fluorescens C-2 Aspergillus sp.

Moringa oleifera seeds — Moringa oleifera seeds — Filamentous fungal TiO2 –NPs Chlorella vulgaris Cellex-T resin Soybean hull — Yamadazyma spartinae TiO2 –NPs

Streptococcus pyogenes Sepabeads SP 70

Dowex Optipore SD-2

— —

Vermicompost Olive pomace OP-200

Streptococcus

Support

Biomaterials

TABLE 3 Some examples of metal ion preconcentration by solid-phase extraction with solid support immobilized biomaterials (Continued)




243

FIG. 4. Scheme for chemical modification of nanoparticles.

Al2 O3 , TiO2 , ZrO2 , CeO2 , Fe3 O4 , and SiO2 , were documented in new studies because of their unique properties such as surface reactivity and high surface area. Recently, these substances have been used in the preconcentration of hazardous trace metal ions since they provide rapid chemical activity, due to their high surface area, and high adsorption capacity (Garc´ıa-Ruiz et al., 2011; Quétal et al., 2010). These materials can be easily prepared and produced compared to other types of solid sorbent materials, and numerous techniques have been used for producing nanometer particles, such as vapor condensation, chemical synthesis, solidstate processes, and biological processes. Various types of techniques have been used detect nanoparticles, such as SEM, TEM, STM, AFM, and SNOM (Kaur and Gupta, 2009). Furthermore, nanoparticles can be coated by complex reagents for supporting and increasing the number of binding sites of interations and thus enhance the uptake of the target analyte. The selectivity of nanoparticles for adsorbent metal ions can be increased by using a modification of nanometer-sized adsorption with an organic compound. Ordinarily, this modification can completed in two different ways:

1. Physical modification with organic reagent on the sorbent by steeping the solid sorbent with a solution containing particular substances (Zheng et al., 2006). This method is simple and the procedure more easily performed. 2. Chemical modification with organic chelating ligand (Afkhami et al., 2011a; Cui et al., 2007) (Figure 4). Likewise, modification by chemical bonding has strong covalent bonds that allows saving the loaded reagent on the sorbent during the sample elution process. Magnetite nanoparticles for extraction of metal ions, such as Fe2 O3 , by immobilization on different substrates, like diamide derivatives of p-tert-butylcalix-4-arene for the removal of U(VI) from aqueous solutions, has been described (Sayin and Yilmaz, 2011). A novel magnetic nano-adsorbent was synthesized for the adsorption of metal ions by surface modification of Fe3 O4 nanoparticles with carboxymethyl-β-cyclodextrin. The adsorption behavior of these sorbents was examined using Cu2+ as the target metal contaminant because of its extensive environmental impact (Badruddoza et al., 2011). A comparison of analytical features of techniques for metal preconcentration with nanomaterials is shown in Table 4.

244

γ -MPTMS

— Bismuthiol-II

—

PAN

— — PAN

2,6-PDCA

— AMT

—

MBT/SDS —

SA

SDS-PAN SDS-PAN

TiO2 SiO2 /Fe3 O4

TiO2

TiO2

B2 O3 /TiO2 Fe3 O4 Fe3 O4

SiO2

ZrO2 /B2 O3 Fe3 O4 /TMSPT

ZrO2 /B2 O3

Al2 O3 /Fe3 O4 Fe3 O4

SiO2 /Fe3 O4

Fe3 O4 /Al2 O3 Fe3 O4 /Al2 O3

Ligand

SiO2 /Fe3 O4

Support

As(V) Ag(I) Cd(II) Cu(II) Zn(II) Co(II) Cu(II) Cd(II) Ag(I) Pd(II) Rh(II) Cu(II) Cd(II) Ni(II) Cr(III) Pb(II) Cd(II)

Hg(II)

Cd(II) Cu(II) Hg(II) Pb(II) Pb(II) Cr(III) Cu(II) Pb(II) Cd(II) Ni(II) Mn(II) Cd(II) Cd(II) Hg(II) Mn(II)

Analyte

0.00925 0.12 0.12 0.13 0.11 3.8 3.3 3.1 0.56 2.9 1.4 0.22 0.11 0.27 0.15 8.0 1.5

0.09

0.000024 0.000092 0.000107 0.000056 0.0095 0.043 0.058 0.085 0.25 1.0 1.0 0.96 1.44 0.04 0.1

D.L. (μg/L)

83 83

200

20 194 190 170 182 10 10 15 250 150

175

50 1230 28

462 476 427 413 50 96 95 87 66.7 66.7 —


FAAS FAAS

FAAS

FAAS FAAS

FAAS

HGAAS ICP-OES

ICP-AES

FAAS (FI)-ICP-OES ICP-OES

FAAS

FAAS

GFAAS ICP-OES

ICP-MS

Detection technique

Water and soil samples Water samples

Water samples Pt-Ir alloy and road dust samples Water and food samples

Tap water and tea leaves

Environmental and biological samples Water samples Environmental samples

Tap water and tea leaves Aqueous samples Cereal samples

Water samples

Water samples

Water samples Environmental samples

Biological and environmental samples

Sample

TABLE 4 Some examples of metal ion preconcentration by solid-phase extraction with nanomaterials


Tavallali, 2011b Tavallali, 2011a

Shishehbore et al., 2011

Karimi et al., 2011 Mohammadi et al., 2011

Yalçinkaya et al., 2011

Erdo˘gan et al., 2011 Mashhadizadeh and Karami, 2011

Kalfa et al., 2009 Faraji et al., 2010 Khajeh and Sanchooli, 2010 Zhang et al., 2010a

Manzoori et al., 2009

Zhou et al., 2009

Liu and Liang, 2008 Suleiman et al., 2009

Huang and Hu, 2008

Reference

245

—

PANI SDS-PAN H2 Dz

Zincon

SiO2 /Al2 O3

Fe3 O4 Fe3 O4 /Al2 O3 SiO2 /Fe3 O4

SiO2 /Fe3 O4

MeHg Co(II) Cr(III) Cu(II) Pb(II) Zn(II) Pb(II)

Cd(II)

—

CTAB- PAN

AET — —

Fe3 O4 /ZrO2

Fe3 O4

Fe3 O4 SiO2 /MnOx TiO2

Hg(II) Cd(II) Tl(I)

0.04 0.20 0.087

0.005

0.004 0.0026 0.0016 0.0023 0.14 0.19 0.12 0.69

0.1 0.006 0.035 0.011 0.062 0.008 0.01

0.19

0.00016 0.00026 0.00026 0.43 0.55

0.00021

500 39.4 100

1050

25

87.5

100

200

91 30 100

18.4

267

200

300

ICP-OES FAAS GFAAS

FAAS

FAAS

FAAS

ICP-MS

GFAAS

GC-MS SI-LOV-ETAAS ICP-OES

FAAS

FAAS

ICP-MS

ICP-MS

Environmental and biological samples Environmental water samples Water and fish samples Natural water samples Environmental water samples

Water, food, and biological samples

Natural and drinking water samples Environmental water samples

Seawater sample Water samples Environmental and biological samples

Various water, food, industrial effluent, and urine samples Water samples

Environmental water of tobacco growing area Biological and environmental samples

Rofouei et al., 2012 Lima et al., 2013 Asadpour et al., in press

Faraji et al., in press

Wu et al., 2012

Bagheri et al., 2012

Zhang et al., 2012a

Jiang et al., 2012

Mendoça-Costa et al., 2011 Mehdinia et al., 2011 Wang et al., 2012 Cheng et al., 2012

Afkhami et al., 2011b

Zhang et al., 2011

Huang et al., 2011

FAAS: flame atomic absorption spectrometry; (FI)-ICP-OES: flow injection-inductively coupled plasma-optical emission spectrometry; GC-MS: gas chromatography-mass spectrometry; GFAAS: graphite furnace atomic absorption spectrometry; HGAAS: hydride generation atomic absorption spectrometry; ICP-AES: inductively coupled plasmaatomic emission spectrometry; ICP-MS: inductively coupled plasma-mass spectrometry; ICP-OES: inductively coupled plasma-optical emission spectrometry; SI-LOV-ETAAS: sequential injection-lab-on-valve-electrothermal atomic absorption spectrometry.

L

Fe3 O4 /SiO2

Pb(II)

SDS-DNPH

Al2 O3

Cd(II) Mn(II) Pb(II) Pb(II) Cr(III)

Cd(II) Cr(III) Mn(II) Cu(II) Pb(II) Cd(II) Cu(II) Cr(III)

IDA

SiO2 /Fe3 O4

As(V)

Fe3 O4 /SiO2 /TiO2 —

AAPTS

SiO2 /Fe3 O4



246


CONCLUSION AND TRENDS Various developments were described and presented for the application of solid-phase extraction as unique analytical methods for preconcentration, separation, and determination of trace metal ions in biological and real samples. Several categories of solid sorbents have been discussed e.g., ion-imprinted polymers, carbon nanotubes, biosorbents, and nanoparticles. These types of solid sorbents provide new properties and novel applications in a wide range of matrix samples. Recently, the extensive use of solid-phase extraction involving ion-imprinted polymers as multipurpose compounds has resulted in more selective sorbents, with high retention capacity and low cost compared with traditional solid-phase extraction methods. CNTs exhibit a wide range of applications as solid sorbent for preconcentration and separation of metal ions from environmental and biological samples. CNTs possess chemical stability, high electrical conductivity, high thermal stability, mechanical strength, and large specific surface area. This review also discussed a number of solid-phase extraction methods based on biosorption applied for extraction of metal ions from a matrix sample. These sorbents rely on the activities of the cell wall, composed of polysaccharides, proteins, lipids, and other substances, presenting several active sites that can be implicated in metal binding, such as carboxyl, hydroxyl, sulfate, phosphate, and amino groups. Biosorption species are categorized into living organisms (with biological activity) and dead organisms (without biological activity). Many cells of organisms, e.g., bacteria, fungi, and yeast, have been immobilized on appropriate supports for preconcentration systems for various heavy metal ions. Several solid supports have been used such as silica gel, glass beads, sepiolite, polyurethane, nanoparticles, and XAD series resins. Biosorption by microorganisms immobilized on a solid support possesses several advantages, such as efficient preconcentration with high recovery, simplicity, cost effectiveness, and environmental friendliness. Nanoparticles (NPs) represent novel solid sorbents for preconcentration of hazardous metal ions. Their particle size ranges from 1 to about 100 nm. Many applications have been cited for several types of nanometer-sized metal oxides such as Al2 O3 , TiO2 , ZrO2 , CeO2 , Fe3 O4 , and SiO2 . Also, NPs are established as being highly selective and sensitive for determination of trace levels of metal ions. REFERENCES Acosta, M.; Savio, M.; Talio, M. C.; Ferramola, M. L.; Gil, R. A.; Martinez, L. D. On-line Solid Phase Extraction of Cd from Protein Fractions of Serum Using Oxidized Carbon Nanotubes Coupled to Electrothermal Atomization Atomic Absorption Spectrometry. Microchem J. 2013, 110, 94–98. Afkhami, A.; Madrakian, T.; Ahmadi, R.; Bagheri, H.; Tabatabaee, M. Chemically Modified Alumina Nanoparticles for Selective Solid Phase Extraction and Preconcentration of Trace Amounts of Cd(II). Microchim. Acta 2011a, 175, 69–77.

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Influence of ashing techniques on the analysis of trace elements in biological samples : II. Dry ashing.

back-extraction.

Extraction of trace nitrophenols in environmental water samples using boronate affinity sorbent.

New developments in the extraction and determination of parabens in cosmetics and environmental samples. A review.

Rapid screening of heavy metals and trace elements in environmental samples using portable X-ray fluorescence spectrometer, A comparative study.

Guest editorial: Environmental aspects of trace elements in coal.

Trace elements and carcinogenicity: a subject in review.

Synthesis and application of ion-imprinted polymer nanoparticles for the extraction and preconcentration of copper ions in environmental water samples.

Application of nanoclay for preconcentration of ultra trace amounts of palladium in environmental samples prior to its determination by ETAAS.

Cloud-point extraction, preconcentration and spectrophotometric determination of trace quantities of copper in food, water and biological samples.

Fabrication of a Dipole-assisted Solid Phase Extraction Microchip for Trace Metal Analysis in Water Samples.

A separation scheme for the determination of trace elements in biological materials by neutron activation analysis.

Characterization of carbon nanotubes and analytical methods for their determination in environmental and biological samples: a review.

Automation of ⁹⁹Tc extraction by LOV prior ICP-MS detection: application to environmental samples.

The environmental geochemistry of trace elements and naturally radionuclides in a coal gangue brick-making plant.

Application of a magnetic molecularly imprinted polymer for the selective extraction and trace detection of lamotrigine in urine and plasma samples.

Determination of trace elements in plants by the X-ray fluorescence analysis for environmental pollution investigations.

Application of gas chromatography high-resolution mass spectrometry to the determination of trace monobromopolychlorodibenzo-p-dioxins in environmental samples.

A new thiourea derivative [2-(3-ethylthioureido)benzoic acid] for cloud point extraction of some trace metals in water, biological and food samples.

Trace elements.

Trace elements.

Trace elements in man.

Trace elements in animals.

Reliability of the ICP-AES for trace elements studies of biological materials.