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Article history:
Received 5 August 2013
Received in revised form 14 September 2013
Accepted 29 September 2013
Available online 8 October 2013
Keywords:
Cloud point extraction
Copper
Spectrophotometry
Triton X-114
Food, water and biological samples
a b s t r a c t
A new, simple and sensitive cloud point extraction procedure was presented for the preconcentration and
determination of copper(II) ion in food, water and biological samples. The analyte was complexed with a
new synthesized reagent, 2-amino-4-(m-tolylazo)pyridine-3-ol (ATAP) as a new complexing agent and
Triton X-114 as the surfactant. After centrifugation, dilution of the surfactant-rich phase with 0.4 mL
of ethanol acidied with 1.0 M HNO3 was performed after phase separation, and the copper contents
were measured by spectrophotometry at kmax 608 nm. The inuence of analytical parameters including
concentration of complexing agent, Triton X-114, pH, equilibration temperature and time, centrifuge rate
and time were optimized. The analytical characteristics of the method (e.g. linear range, molar absorptivity, Sandell sensitivity, optimum Ringbom concentration ranges limits of detection and quantication,
preconcentration factor, and improvement factors) were obtained. Linearity was obeyed in the range
of 4.0115 ng mL1 of Cu(II) ion. The detection and quantication limits of the method were 1.20 and
3.94 ng mL1 of Cu(II) ion, respectively. The interference effect of some anions and cations was also
tested. The method was applied for determination of copper in food, water and biological samples.
Published by Elsevier B.V.
Introduction
In recent years, the toxicity and the effect of trace elements on
human health and the environment are receiving increasing
attention in pollution and nutritional studies. Copper is one of
Corresponding author. Tel.: +20 552420204; fax: +20 552308213.
E-mail address: aymangouda77@gmail.com (A.A. Gouda).
1386-1425/$ - see front matter Published by Elsevier B.V.
http://dx.doi.org/10.1016/j.saa.2013.09.146
A.A. Gouda, A.S. Amin / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 120 (2014) 8896
of copper in foods originates mainly from fungicide residues containing this metal used in agriculture and from water plumbing.
The determination of trace levels of copper is important because
it could catalyze oxidation of fatty acid chains, exerting a deleterious inuence on shelf life and nutritional value [3].
Therefore, sensitive, reproducible and accurate analytical
methods are required for the determination of trace copper in
environmental biological and water samples. Although inductively
coupled plasma atomic emission spectrometry (ICP-AES) and
atomic absorption spectrometry (AAS) [4,5] are among the most
widely used methods for trace metal determination, they are
usually insufcient due to the matrix interferences and the very
low concentration of metal ions. For these reasons, an efcient separation and preconcentration procedure is often required prior to
the measurement step.
Currently, the most widely used preconcentration methods are
liquid phase microextraction [6], liquidliquid extraction [7], ionexchange [8], resins chelation [9], ber chelation [10], solid-phase
extraction (SPE) [11,12], electrochemical deposition [13] and cloud
point extraction (CPE) [14]. CPE technique has become increasingly
popular in comparison with the classical liquidliquid extraction
method because of its advantages of high enrichment factor, high
recovery, rapid phase separation, low cost, low consumption of
organic solvents and the ability of combination with different
detection.
Micelles and other organized amphiphilic assemblies are
increasingly utilized in analytical chemistry especially in separation and preconcentration procedures. Their unique micro heterogeneous structures capable of selective interaction with different
solute molecules can strongly modify solubility, chemical equilibrium, kinetics and the spectroscopic properties of analytes and
reagents [15,16]. Compared with other extraction methods such
as liquidliquid extraction, cloud point extraction (CPE) exhibits
much more environmentally friendly properties, and it is safer
because small volumes of noxious surfactants are used instead of
toxic organic solvents. CPE is an attractive technique that reduces
the consumption and exposures to a solvent and it also reduces
disposal costs and extraction time that has been used for preconcentration of metal ions after the formation of sparingly watersoluble complexes [1719]. Triton X-114 was chosen as the nonionic surfactant because of its low cloud point temperature and
high density of the surfactant-rich phase as well as its low cost
commercially and lower toxicity. The efciency of the cloud point
extraction depends on the hydrophobicity of the ligand and of the
complex formed, on the apparent equilibrium constants in the
micellar medium and on the formation kinetics of the complex
and on the transference between the phases.
In the present work, a new reagent, 2-amino-4-(m-tolylazo)
pyridine-3-ol (ATAP) was synthesized, characterized and used for
preconcentration and determination of copper(II) by spectrophotometry based on cloud-point extraction (CPE) of the copper(II)
complexed with ATAP using Triton X-114 as surfactant. The proposed method was also applied to the determination of copper in
food, water and biological samples.
Experimental
Apparatus
All Absorption spectra and absorbance measurements were
recorded and measured with a Perkin-Elmer k3B double beam
UVVIS spectrophotometer with 5.0 mm quartz cuvettes. An Orion
research model 601A/digital ionalyzer tted with a combined
glasscalomel electrode was used for pH adjustment and checking
the pH value of buffer solutions. An inductively coupled plasma
89
(ICP) model Varian Liberty 150AX Turbo was used for copper concentration determination. A Hettich, EBA 21 model centrifuge with
50 mL calibrated centrifuge tubes were used to achieve and accelerate the phase separation process, respectively. A thermostated
water bath with a good temperature control within 1.0 C was
used for cloud point temperature experiments.
In order to characterize the synthesized reagent, the IR
spectrum was recorded as KBr discs using Matson FTIR spectrophotometer in the 4000200 cm1 range. The 1H-NMR spectrum of the
reagent was performed using a varian EM 390-90 NMR spectrometer in d6-DMSO as solvent using tetramethylsilane (TME) as an
internal standard. The microanalysis of C, H and N of this
compound was performed in the Microanalytical Center of Cairo
University.
Chemicals and reagents
High-purity ethanol, methanol, isopentyl alcohol, chloroform,
nitric acid, hydrochloric acid, and ammonia solution all from Merck
(Darmstadt, Germany) were used without any further purication.
Analytical-grade cupric nitrate, mercuric chloride, sodium molybdate, sodium tungstate, sodium acetate, hydroxylamine hydrochloride and nitrate salts of sodium, potassium, lithium, calcium,
barium, beryllium, magnesium, manganese, strontium, cobalt, iron,
lead, and nickel all from Merck were of the highest purity available
and used without any further purication. Doubly distilled and
deionized water was used throughout.
A standard stock copper solution (1000 mg L1) was prepared
by dissolving 0.3802 g of Cu(NO3)23H2O, (Merck) in water and
diluting to 100 mL. This solution was standardized by iodimetric
titration. Working solutions were prepared by appropriate dilution
of the stock solution. A 2.0% (v/v) Triton X-114 from Merck was
prepared by dissolving 2.0 mL of Triton X-114 in bidistilled water
in 100 mL volumetric ask with stirring. Cloud point of Triton
X-114 in aqueous solution is 24 C [20].
Thiel buffer solutions of pH 2.012 were prepared by mixing
different proportions of two successive solutions in the following
list to obtain the required pH-value:
(a) 0.05 M oxalic acid +0.20 M boric acid;
(b) 0.20 M boric acid +0.05 M succinic acid +0.05 M sodium
sulphate;
(c) 0.05 M sodium tetraborate;
(d) 0.05 M sodium bicarbonate; resulting in a + b (pH 1.52.5),
b + c (pH 3.09.0), and c + d (pH 9.512) [21].
Synthesis of 2-amino-4-(m-tolylazo)pyridine-3-ol (ATAP) reagent
The azo dye under investigation was prepared by the common
way used for preparing azo dye derivatives of aromatic amines. A
0.01 mole of p-toluidine was converted to the hydrochloric form
by adding the least amount of 1:1 HCl then diluting with water
and cooling at 2.0 C. A cooled solution of NaNO2 (0.01 mole) is
added gradually with continuous stirring to the amine salt. The
resulting diazonium salt solution is allowed to stand in ice bath
for 15 min with stirring at 2.0 C and added gradually to a solution of 0.01 mole of 2-amino-3-hydroxypyridine dissolved in 10%
NaOH which cooled at 2.0 C. The resulting solution is allowed
to stand for 15 min with constant stirring until the azo dye completely formed. The obtained azo compound is ltered off, dried
and recrystallized in ethanol. The purity of the resulting azo compound is checked by measuring the melting point constancy. The
chemical structure of the synthesized reagent (ATAP) (Fig. 1) was
detected by elemental analysis (C, H, N), IR and 1H-NMR spectra.
A 5.0 104 M solution of the ATAP reagent was prepared by
dissolving an appropriate weight of reagent in 10 mL ethanol and
90
A.A. Gouda, A.S. Amin / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 120 (2014) 8896
H2N
OH
CH 3
H 2N
CH 3
OH
H 2N
H
N
CH 3
91
A.A. Gouda, A.S. Amin / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 120 (2014) 8896
2
OH
3
CH 3
0.3
0.2
0.1
0
500
540
580
620
660
700
Wavelength (nm)
Fig. 2. Absorption spectra for 75 ngAbsorption spectra for 75mL1 and lg mL1
Cu(II) complexed with 3.0 105 M ATAP using 0.1% (v/v) Triton X-114 at pH 4.5,
with and without CPE, respectively.
0.6
CH3
0.4
II
0.5
0.5
N
The signal lying at very downeld side 3.84 ppm are due to the
hydrogens of NH2 group. A new multiple signals at 1.23 ppm is due
to the protons of CH3 group. The multi signals appear at 7.327.07
and 6.586.45 ppm are due to the protons of rings I and II
respectively.
Absorption spectra
ATAP shows maximum absorbance at 496 nm at pH 4.5; Cu(II)
in buffer medium of pH 4.5 reacts with ATAP in absence (kmax
575 nm) and in the presence of Triton X-114 and the absorbance
of solution shift to bathochromic at 608 nm. Therefore the ternary
complex of Cu(II)ATAPTriton X-114 can be extracted by CPE
method. After separation of surfactant-rich phase, the absorbance
was measured at 608 nm against a reagent blank (Fig. 2). Therefore, the method is suitable for preconcentration and spectrophotometric determination of Cu(II).
Optimization of the system
To take full advantage of the procedure, the reagent concentrations and reaction conditions must be optimized. Various experimental parameters were studied in order to obtain optimized
system. These parameters were optimized by setting all parameters to be constant and optimizing one each time.
The effect of pH
The formation of metalcomplex and its chemical stability are
the two important inuence factors for CPE. The pH plays an unique role on metalcomplex formation and subsequent extraction,
0.4
Absorbance
1
H 2N
with CPE
without CPE
0.6
Absorbance
0.3
0.2
0.1
10
11
pH
Fig. 3. Effect of pH of thiel buffer on the absorbance of the Cu(II)ATAP complex.
Conditions: 75 ng mL1 Cu(II), 3.0 105 M ATAP, 0.1% (v/v) Triton X-114, temperature 50 C.
92
A.A. Gouda, A.S. Amin / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 120 (2014) 8896
Table 1
Analytical characteristics of the proposed method.
Parameters
After CPE
Before CPE
Amount of ethanol
pH
Optimum [ATAP]
Reaction time (min)
Stirring time (min)
kmax (nm)
Beers range (ng mL1)
Ringbom range (ng mL1)
Molar absorptivity (L mol1 cm1)
Sandell sensitivity (ng cm2)
Regression equation a
Slope
Intercept
Correlation coefcient (r)
RSD a (%)
Detection limits (ng mL1)
Quantication limits (ng mL1)
Preconcentration factor
Enrichment factor
Consumptive index (mL)
0.4
4.5
3.0 105
10
10
608
4.0115
10110
4.37 105
0.0145
4.5
3.0 105
20
575
5000250,000
7500225,000
1.40 103
45
6.87
0.005
0.9996
1.25
1.20
3.94
125
3122
0.016
0.0022
0.009
0.9985
2.90
1500
4950
93
A.A. Gouda, A.S. Amin / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 120 (2014) 8896
Table 2
Comparative data from some recent studies on CPE preconcentrationseparation of Cu(II).
Reagent
Micellar system
Detection
DL
(ng mL1)
PF/
EF
Sample
Ref.
Dithizone
HEPTS
Triton X-114
Triton X-114
Tetrahydrofuran
2.0 mL methanol
ST
ST
4.6
0.1
10
5
[29]
[30]
4-BPDC
Isoleucine
Diethyldithiocarbamate
Thiamine
Triton
Triton
Triton
Triton
X-114
X-100
X-100
X-114
NA
Up to 1.0 mL with methanol
3.0 mL ethanol
At 2.5 mL with ethanol/water (1:1)
ST
ST
ST
SF
1.6
5
0.4
0.29
NA
22
18
10
Me-BTABr
Triton X-114
FAAS
1.08
17
NDTT
Triton X-114
FAAS
0.22
22.4
Water
[36]
Cupron
Triton X-114
FAAS
0.04
88
Triton X-114
FAAS
1.5
14
[37]
Me-BDBD
Alizarin Red S
Triton X-114
FAAS
1.07
21
Water
[39]
PDBDM (chrysoidine)
Triton X-114
Liver
Water and saturated
saline
Natural water
Food and water
Water and food
Water and parenteral
solutions
Water samples
FAAS
0.6
15
[24]
PTU
PAN
DFID (thiophenytoin)
Triton X-114
OP-7
Triton X-114
FAAS
FAAS
FAAS
1.6
8.54
1.5
30
NA
39
[40]
[41]
[42]
N,N0 -bis(2-hydroxyacetophenone)1,2-propanediimine
Sulfathiazolylazo resorsin
Caproic acid and octylamine
N-phenyl benzohydroxamic acid
MPMP
Triton X-114
FAAS
0.06
20
Environmental and
biological
Environmental
Waters
Water, blood,
vegetables
Waters
Triton X-100
OP-10
Triton X-114
Triton X-114
FAAS
FAAS
FI-FAAS
FI-FAAS
0.64
10
1
0.15
25
NA
45
81
Waters
Water
Water and hair
Rice our and water
[44]
[45]
[46]
[47]
DDTC
Triton X-114
FAAS
1.1
11
[48]
ATAP
Triton X-114
ST
1.2
125
This work
[31]
[32]
[33]
[34]
[35]
[38]
[43]
HEPTS: 4-ethyl-1-(pyridin-2-yl)thiosemicarbazide; 4-BPDC: (4-bencylpiperidine-ditiocarbamate; Me-BTABr: 2-[20 -(6-methyl-benzothiazolylazo)]-4-bromophenol; NDTT: 6(2-naphthyl)-2,3-dihydro-as-triazine-3-thione; Me-BDBD: 6-[20 -(60 -methyl-benzothiazolylazo)]-1,2-dihydroxy-3,5-benzenedisulfonic acid; Alizarin Red S: 1,2-dihydroxyanthraquinone-3-sulfonic acid sodium salt; PDBDM: 4-(Phenyl diazenyl) benzene-1,3-diamine; PTU: 4-hydroxy-2-mercapto-6-propylpyrimidine; PAN: 1-(2-pyridylazo)-2naphthol; MPMP: 2-[(2-mercaptophenylimino)-methyl]phenol; DDTC: sodium diethyldithiocarbamate; OP-10: Polyoxyethylated phenol; OP = 7: polyoxyethylated alkylphenol; Cupron: 1,5-diphenyl-benzoin; DFID (thiophenytoin): 5,5-diphenylimidazolidine-2-thione-,4-one; TritonX-114: octylphenoxypolyethoxyethanol; FAAS: ame
atomic absorption spectrometry, ST: spectrophotometry; SF: spectrouorimetry; CE: capillary electrophoresis; SRP surfactant-rich phase; PF preconcentration factor; EF:
enrichment factor; DL detection limit; NA: non-available data.
Table 3
Comparison of selected reagents for the spectrophotometric determination of Cu(II).
Reagent
2-(5-Bromo-2-pyridylazo)-5-diethylamino amino phenol, polyglycol octylphenyl ether
1,5-Bis(di-2-pyridylmethylene) thiocarbonohydrazide
Diethyldithiocarbamate, b-cyclodextrin
Bis(acetylacetone)ethylenediimine
Poly[allylamine-co-N-4-(8-aminoquinolyl-5-azo) benzylideneallylamine]
3,30 -(1,3-Propanediyldiimine)bis-[3-methyl-2-butanone]dioxime
1-[Pyridyl-(2)-azo]-naphthol-(2), TX-100, N,N0 -diphenylbenzamidine
S,S0 -bis(2-aminophenyl)oxalate
3-{2-[2-(2-Hydroxyimino-1-methyl-propylideneamino)-ethylamino]-ethyl-imino}-butan-2one oxime
Naphthazarin
1-Phenyl-1,2-propanedione-2-oxime thiosemi-carbazone
Thiomichlersketone, polyethylene octyl phenyl ether
Dimethylindodicarbocyanine
Bromosulphonazo III
4-(20 -benzothiazolylazo)-salicylic acid (BTAS)
ATAP
kmax
(nm)
e/
Linear range
(lg mL1)
Ref.
560
500
436
370
590
525
520
504
570
15
4.2
1.3
4.1
2.95
11.4
0.54
0.16
0.018
NA
06.0
Up to 80
0l.0
0.5350
To 0.6
0.4150
0.2225
[49]
[50]
[51]
[52]
[53]
[54]
[55]
[56]
[57]
330
465
500
650
616.8
485
608
1.84
0.56
5.7
12
33
2.35
43.7
Up to 4.5
0.387.63
00.6
0.01.2
01.024
0.635.04
0.0040.115
[58]
[59]
[60]
[61]
[62]
[63]
This work
94
A.A. Gouda, A.S. Amin / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 120 (2014) 8896
Table 4
Tolerance ratio of diverse ions on the determination of 75 ng mL1 Cu(II) (relative
error 5.0%).
Ion added
6000a
4500
2500
1750
1000
750
400
250
125
70
45
Table 5
Recovery studies of Cu(II) in real samples.
Sample
Added
Vegetablec
0.0
30
60
0.0
35
70
0.0
25
50
0.0
40
80
0.0
45
90
0.0
20
35
0.0
30
60
90
0.0
15
30
0.0
20
40
0.0
35
70
105
Liverc
Meatc
Lotus (tree)
Soilc
Blood
Tap waterd
Waste waterd
River waterd
Chocolate
a
b
c
d
Founda
Proposed
ICP-AES
28.9
59.2
88.5
29.1
64.2
99.5
30.6
55.3
80.2
17.7
57.5
98.3
18.0
63.5
107.3
77.7
98.2
112.4
6.2
36.3
66.5
95.8
75.6
91.0
105.1
63.2
83.0
102.5
0.2
35.3
70.1
105.4
28.8
59.0
89.2
29.0
64.5
99.7
30.5
55.8
81.0
17.8
57.6
88.0
18.1
63.6
108.0
77.5
98.4
113.1
6.3
36.5
66.0
96.6
75.5
91.2
105.9
63.0
83.6
104.0
0.2
35.4
70.3
105.3
RSD (%)
Recovery (%)
1.4
1.1
100.51
99.55
100.16
100.40
99.46
99.50
99.65
100.61
100.79
99.35
100.51
99.73
100.28
100.46
99.58
100.44
99.52
99.76
99.32
100.28
99.86
100.19
1.3
1.0
1.3
0.9
1.3
1.0
1.4
1.0
1.3
0.9
1.2
1.4
1.1
1.2
1.5
0.9
1.3
1.1
0.8
1.1
1.0
1.2
1.4
1.1
0.9
t-Testb
F-Valueb
0.87
1.11
2.12
2.60
0.78
1.19
1.93
2.92
0.96
1.10
2.13
2.54
1.23
1.15
3.18
2.78
1.24
0.90
3.19
2.02
1.17
2.85
0.82
1.09
1.34
1.99
2.47
3.41
1.11
1.25
2.69
3.13
0.94
1.18
2.17
2.90
0.89
0.98
1.08
2.12
2.33
2.41
A.A. Gouda, A.S. Amin / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 120 (2014) 8896
The separation occurred efciently, resulting in good enrichment factor and low LOD. A comparison of the proposed method
with other preconcentration procedures [24,2948] for Cu using
several reagents is given in Table 2. The proposed methodology offers a simple, rapid, inexpensive and nonpolluting alternative to
other preconcentration techniques. The detection limits of analytes
are superior to those of preconcentration techniques. The sensitivity expressed as molar absorptivity of the proposed method is
compared with those of published spectrophotometric methods
(Table 3). The proposed method is more sensitive than other methods [4963], that based on spectrophotometry (Table 3).
Interference
In order to study the selective separation and determination of
copper ions from its binary mixtures with diverse metal ions, an
aliquot of aqueous solutions (50 mL) containing 75 ng Cu(II) and
mg amounts of other cations was taken and the proposed procedure was followed. The tolerance limit was taken as the ratio of
foreign ions to the Cu(II) ion determined that causes maximum
limit tested 5.0% error in the absorbance value. The results are
summarized in Table 4. The result shows that most common ions
do not interfere with the determination suggesting the highly
selectivity of the proposed method.
Analytical applications
In order to conrm the applicability of the proposed method, it
has been applied to the determination of nanogram amounts of
Cu(II) in food, water and biological samples. The reliability of the
presented method was checked by spiking experiments and independent analysis. The results for this study are presented in Table 5.
An ICP-AES method was used as a reference method and the results
are also shown in Table 5. The recovery of spiked samples is satisfactorily reasonable and was conrmed using addition method,
which indicates the capability of the system in the determination
of ions. A good agreement was obtained between the added and
measured analyte amounts. The recovery values calculated for
the added standards were always higher than 95%, thus conrming
the accuracy of the procedure and its independence from the matrix effects.
The performance of the proposed method was assessed by
calculation of the t-value (for accuracy) and F-test (for precision)
compared with ICP-AES method. The mean values were obtained
in a Students t- and F-tests at 95% condence limits for ve
degrees of freedom [64]. The results showed that the calculated
values (Table 5) did not exceed the theoretical values. A wider
range of determination, higher accuracy, more stability and less
time consuming, shows the advantage of the proposed method
over other method.
Conclusions
Cloud point extraction was used to the preconcentration of
copper in different samples. The method, which is based on the
cloud point extraction of the complex of copper with ATAP, allows
the determination of copper as low as 1.2 ng mL1. The proposed
method requires inexpensive instrumentation and offers safety,
good selectivity, accuracy and precision that can be applied to
the determination of copper in real samples. The surfactant has
been used for preconcentration of copper in samples, and thus
toxic solvent extraction, has been avoided. The methodology offers
a simple, rapid, inexpensive and nonpolluting alternative to other
preconcentration techniques. The method is relatively rapid
95
comparing with previously reported procedures for the enrichment of analyte ions.
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