Microchim Acta (2012) 177:4752
DOI 10.1007/s00604-011-0751-8
ORIGINAL PAPER
Separation and preconcentration of mercury in water
samples by ionic liquid supported cloud point extraction
and fluorimetric determination
Serap Seyhan Bozkurt & Kasim Ocakoglu &
Melek Merdivan
Received: 23 September 2011 / Accepted: 11 December 2011 / Published online: 28 December 2011
# Springer-Verlag 2011
Abstract We have developed a cloud point extraction proce-
dure based on room temperature ionic liquid for the preconcen-
tration and determination of mercury in water samples. Mercury
ion was quantitatively extracted with tetraethyleneglycol-bis(3-
methylimidazolium) diiodide in the form of its complex with
5,10,15,20-tetra-(4-phenoxyphenyl)porphyrin. The complex
was back extracted from the room temperature ionic liquid
phase into an aqueous media prior to its analysis by spectro-
fluorimetry. An overall preconcentration factor of 45 was ac-
complished upon preconcentration of a 20 mL sample. The
limit of detection obtained under the optimal conditions is
0.08 g mL1, and the relative standard deviation for 10 repli-
cate assays (at 0.5 g mL1 of Hg) was 2.4%. The method was
successfully applied to the determination of mercury in tap,
river and mineral water samples.
Keywords Ionic liquid . Preconcentration . Mercury . Cloud
point extraction . Spectrofluorimetry
Introduction
Mercury is one of the most harmful pollutants and it has
become widespread into the environment mainly as a result
S. S. Bozkurt (*) : M. Merdivan
Chemistry Department, Dokuz Eylul University,
Faculty of Sciences and Arts,
Kaynaklar Campus,
35160 Izmir, Turkey
e-mail: serap.seyhan@deu.edu.tr
K. Ocakoglu
Advanced Technologies Research & Application Center,
Mersin University,
Ciftlikkoy Campus,
TR33343 Mersin, Turkey
of anthropogenic activities [1]. Mercury has no beneficial
biological function, and its presence in living organisms is
associated with cancer, birth defects, and other undesirable
outcomes [2]. One of the routes of incorporation of mercury
into the human body is drinking water [3]. Hence, control of
mercury is becoming increasingly important, especially in
water sources. Since mercury concentrations in waters are
expected to be very low [4], powerful techniques are re-
quired and only few of them show enough sensitivity.
Different analytical techniques have been used for
mercury determination at low concentrations including,
cold vapor atomic absorption spectrometry [5], cold
vapor atomic fluorescence spectrometry [6], inductively
coupled plasma optical emission spectrometry [7], and
inductively coupled plasma mass spectrometry [8]. Mo-
lecular fluorescence is attracting a great deal of interest
in environmental monitoring since it is inherently more
sensitive than other molecular spectroscopies and so it
can be used for the analysis of very low trace concen-
trations [9].
Separation and preconcentration procedures based on
cloud point extraction and liquid liquid microextraction
have been extensively applied to separate and preconcen-
trate mercury ions from different matrices [1012]. The use
of cloud point extraction as an alternative to conventional
solvent extraction technique has presented several advan-
tages, such as excellent concentration factors, lower cost,
higher safety and simplicity, and it does not need to handle a
great volume of organic solvent that is generally toxic [13].
In very diluted solutions of non-ionic or zwitterionic surfac-
tant, the monomers are dispersed in the solvent. But above
the critical micellar concentration of the surfactant, these
monomers associate spontaneously, forming aggregates of
colloidal dimensions termed micelles, due to the diminished
solubility of the surfactant in water [14].
48
This clouding phenomenon can be induced by changing
the temperature, additive content, or pressure, resulting the
separation of a single isotropic micellar phase into two
isotropic phases: (a) a surfactant-rich phase of small volume
composed mainly of surfactant, and (b) an aqueous phase
containing surfactant with the concentration level near to
critical micellar concentration. Any species originally pres-
ent that associates and binds to micelles can be extracted and
subsequently preconcentrated in a surfactant-rich phase
[15].
Recently, considerable interest has been manifested in the
use of room temperature ionic liquids (RTIL) as an alterna-
tive to regular solvents in a wide range of applications due to
their unique chemical and physical properties [16, 17].
Some of them are water stability, negligible vapor pressure,
the fact that they remain liquid at room temperature, and
their relatively favorable viscosity and density character-
istics [18]; what makes their use very attractive in separation
processes [19].
In this work, a novel application of the RTIL (tetraethy-
leneglycol-bis(3-methylimidazolium)diiodide, TEGII) as
surfactant and 5,10,15,20-tetra-(4-phenoxyphenyl)porphy-
rin (TPPP) as complexing agent for separation and precon-
centration of mercury in cloud point extraction and
spectrofluorimetric determination of mercury by TPPP is
presented. Mercury was successfully extracted and precon-
centrated under the form of Hg-TPPP complex and later
back extracted into tetrahydrofuran. The feasibility of the
developed method was demonstrated by determining mer-
cury at trace levels in tap, river and mineral water samples.
Experimental
Instrumentation
All fluorescence measurements were carried out on a
Varian-Cary Eclipse Fluorescence Spectrophotometer (Mul-
grave, Australia. http://www.chem.agilent.com), equipped
with a xenon lamps source and 1.0 cm quartz, excitation
and emission slit at 10 nm. pH measurements were made Ino
Lab WTW (Weilheim, Germany. http://www.wtw.com)
model digital pH-meter. Nuve model NF 1,215 centrifuge
was used to accelerate the phase separation.
Chemical and reagents
All chemicals were of analytical reagent grade and were
obtained from Merck (Darmstadt, Germany. http://www.
merck-chemicals.com). A 1,000 g mL1 Hg(II) stock so-
lution was prepared from mercury (II) chloride in doubly
deionized water. Working standard solutions were obtained
daily by stepwise dilution from stock solution. Ionic liquid
S.S. Bozkurt et al.
was synthesized according to the literature [20, 21] and
prepared by dissolving 1.0 g of ionic liquid in 100 mL
deionized water. The ligand TPPP was synthesized accord-
ing to literature [22] and 100 g mL1 stock porphyrin
solution was prepared in tetrahydrofuran. HCl and NaOH
were used for pH adjustment. The water used throughout the
study has been deionized by means of a Millipore Milli-Q
system.
Tap water was allowed to run for 20 min and approxi-
mately 2,000 mL of tap water was collected directly at the
laboratory at Dokuz Eylul University of Turkey. River sam-
ples were collected in cleaned bottles from Meri River, in
Turkey and extracted in developed method [23]. Mineral
water samples were acquired from a local market in Izmir,
Turkey. The water samples were filtered through 0.45 m
pore sized membrane filters and analyzed as soon as
possible.
Synthesis of tetraethyleneglycol-bis(3-methylimidazolium)
diiodide
A mixture of 5 g (12.1 mmol) of 1,11-diiodo-3,6,9-triox-
oundecane, 10 mL of toluene, and 1.92 mL (24.2 mmol) of
1-methylimidazole was heated to 110C (reflux) for 12 h.
After cooling to room temperature the yellow colored lower
phase, which contains the product, was separated from the
upper phase, and washed a few more time with 5 mL tolu-
ene. After the washing step the raw product was dissolved in
dichloromethane and filtered. The filtrate was evaporated to
dryness in a rotary evaporator and a yellowish viscous liquid
was obtained (Scheme 1).
Synthesis of 5,10,15,20-tetra-(4-phenoxyphenyl)porphyrin
0.2 g tetrahydroxyphenylporphyrin was stirred in 15 mL
dimethylformamide with 0.120 g of crushed sodium hy-
droxide. 0.4 g chlorobenzene was added over a period of
an hour from a dropping funnel. After 30 h, 10 mL ethanol
was added to the solution, followed by 80 mL of distilled
water. The product was filtered off and washed with abso-
lute ethanol and then dried (Scheme 2).
Extraction and preconcentration procedure
The extraction/preconcentration procedure was performed
as follows: 0.5 g mL1 of porphyrin solution and 0.2%
Scheme 1 The chemical structure of TEGII
Separation and preconcentration of mercury
Scheme 2 The chemical structure of 5,10,15,20-tetra-(4-phenoxy-
phenyl) porphyrin
(w/v) of ionic liquid were added to 20 mL of 0.5 g mL1
sample solution in a centrifuge tube and was adjusted to pH
7 with NaOH. The mixture was left to stand in a thermo-
stated bath at 60C, for 20 min. Separation of phases was
achieved by centrifugation at 3,500 rpm for 15 min. The
whole system was cooled in an ice bath for 20 min so that
the surfactant-rich phase would regain its viscosity and the
bulk aqueous phase was easily decanted. The remaining
ionic liquid phase was dissolved in 500 L THF as Hg-
TPPP complex and diluting in the ratio of 5:1 and then
analyte contents were determined by spectrofluorimetry.
Fluorescence measurements
A spectrofuorimetric method was based on fuorescence
quenching of porphyrin with Hg(II) for the determination of
the mercury in water samples. The aqueous solutions of Hg(II)
in the concentration range of 0.1 g mL1 to 100 g mL1
were added to 2.0 g mL1 TPPP solution at pH 7. The
fluorescence intensity of TPPP was measured (Fig. 1) in the
absorption solution at an excitation wavelength of 570 nm and
an emission wavelength of 658 nm and calibration curve was
constituted. The fluorescence intensity of Hg-TPPP complex
dissolved in tetrahydrofuran after extraction was measured
and the mercury was determined. All measurements were
carried out at room temperature.
Fig. 1 Fluorescence emission spectra of TPPP in the presence of differ-
ent mercury concentrations (ex 0570 nm, em 0658 nm, pH07, a) TPPP,
[Hg(II)] 0 b) 0.1 g mL1, c) 1.0 g mL1, d) 10 g mL1, e) 20 g mL1,
f) 40 g mL1, g) 60 g mL1, h) 80 g mL1, ) 100 g mL1)
49
Results and discussion
The factors that affect the cloud point extraction such as
extraction temperature, extraction time, sample pH, amount
of ionic liquid and ligand were investigated. Each parameter
was studied three times under identical experimental con-
ditions to confirm the reproducibility of analytical data. The
results were reported with standard deviations (Figs. 1, 2, 3,
4 and 5). To evaluate the practical applicability of the
method, linearity, limits of detection (LOD), recoveries
and relative standard deviations (RSD) were measured un-
der the optimized extraction conditions.
Effect of pH on mercury extraction
The influence of pH on the method sensitivity has been
carried out by conducting a replicate set of similar cloud
point extraction experiments by changing the pH of aqueous
solution of sample in the range of 310. Figure 2 shows the
effect of pH on the sensitivity of the method. It was found
that at pH 68 maximum sensitivities were achieved. There-
fore, a pH 7 was selected for subsequent work. In acidic
medium, a weak complexation and uptake occurs, which is
explained by competition between mercury ions and hydro-
gen ions for the binding to ligand. On the other hand by
increasing the pH, the potential of active sites of ligand for
mercury ion binding and consequently the mercury ions
uptake were increased. The uptake capacities increased with
increasing pH, reaching plateau values at around pH 68.
The uptake of mercury ion beyond pH >8 is attributed to the
formation of metal hydroxide species such as soluble M
(OH)+ and/or insoluble precipitate of M(OH)n.
Effect of ligand concentration
In order to determine the concentration of TPPP required for
quantitative recoveries, the method was applied. The results
were shown in Fig. 3. At point zero for concentration of
ligand, recoveries of mercury ions were not quantitative.
The recovery of the mercury ions increased with increasing
concentrations of porphyrin added and reached a constant
Fig. 2 Effect of pH on the extraction efficiency (n03)
50
Fig. 3 Effect of ligand concentration on cloud point extraction (n03)
value (98%) with at least 0.5 g mL1 TPPP. The optimum
amount of ligand was taken as 0.5 g mL1 TPPP for further
experiments.
Effect of concentration of ionic liquid
This is one of the important parameters to be considered
while developing an analytical method which involves pre-
concentration and simultaneous extraction. The concentra-
tion of TEGII was optimized evaluating concentrations
between 0.05% and 0.5% (w/v). As showed in Fig. 4, max-
imum recoveries of mercury ions were attained at concen-
tration 0.2% (w/v). Above this concentration, there was an
expressive decrease on the recovery of mercury ions. The
decrease could be attributed to increased dilution and the
corresponding decrease in the preconcentration factor. For
further experiments 0.2% (w/v) TEGII was used.
Effect of equilibration temperature and time
It is desirable to have the shortest incubation time and the
lowest possible equilibration temperature, which compro-
mise completion of the reaction and efficient separation of
the phases. In this work, the temperature of the thermostatic
bath was investigated within a range of 3070C (Fig. 5). It
was observed higher extraction efficiency at a temperature
of 60C for mercury ions and this temperature was selected
for the procedure.
Fig. 4 Effect of ionic liquid concentration on the preconcentration (n03)
S.S. Bozkurt et al.
Fig. 5 Effect of equilibration temperature on the recoveries of mercury
ions (n03)
The dependence of extraction efficiency upon incubation
time was also studied in the range of 550 min as shown
Fig. 6. An incubation time of 20 min was optimal for
quantitative extraction of mercury ions. It was therefore
decided to carry out the extraction of mercury at 60C for
20 min as these conditions provided the highest recovery
and the maximum extraction efficiency.
Interferences study
The effect of concomitant ions regularly found was studied
on mercury determination. The study was performed by
analyzing 20 mL solutions containing 0.5 g mL1 mercury
and concomitant ions at the concentration levels at which
they may occur in the sample. Thus, Cu2+, Zn2+, Pb2+, Ni2+,
Mn2+, and Fe3+ could be tolerated up to at least 75 g mL1.
Commonly encountered concomitant ions such as alkali and
alkaline earth elements do not form stable complexes with
TPPP complexing agent at the working pH, and hence are
not extracted from the aqueous solution. On the other hand,
the amounts of anions, usually present in natural water
samples (S2-, CO32-, F-, SO42-, Cl-, PO43-) do not produce
any interference. Analytical signal of the blank was not
modified in the presence of the concomitant ions assayed.
Analytical performance
A 90% extraction was achieved for mercury when the pro-
cedure was developed under optimal experimental condi-
tions. Therefore, the preconcentration factor obtained for a
Fig. 6 Effect of equilibration time on the recoveries of analytes (n03)
Separation and preconcentration of mercury 51

Table 1 Determination of mercury in the water samples by developed be of great interest especially for mercury determination in
method
routine analytical laboratories.
Sample Mercury concentration (g L1) Recovery
(%) Application of real water samples
Added Found

Present ICP-OES In order to validate the developed methodology, the devel-

method oped procedure was applied to the determination of mercury
in tap water, river water and mineral water samples. For this
Tap water n.d.a 2.060.1
purpose, 20 mL of each of the samples were preconcentrated
100 101.910.2 99.8
with according to in extraction and preconcentration proce-
200 201.970.2 100
dure. Also, water samples were analyzed by inductively
River water 4.110.1 4.250.1 coupled plasma optical emission spectrometry (ICP-OES)
100 104.020.2 99.9 and the results were given in Table 1.
200 204.350.2 100.1
Mineral n.d.a 0.180.05
water 100 100.10.2 99.9
Conclusion
200 201.20.2 100.5
a
not detected In this work, a novel and sensitive analytical methodology
(95% confidence interval; n06) for mercury preconcentration and determination in different
water samples using ionic liquid was developed. The com-
sample volume of 20 mL and a resulting ionic liquid phase parison of the results found in the presented study and some
volume of 500 L was 45. The preconcentration factor was works in literature was given in Table 2. The use of room
obtained as the ratio of the slopes of the calibration curves temperature ionic liquids biphasic systems as an alternative
for mercury with and without a preconcentration step. RSD to conventional solvents offers several advantages including
resulting from the analysis of 10 replicates of 20 mL solu- safety and high capacity to extract Hg(II) and other elements
tion containing 0.5 g mL1 was 2.4%. The calibration with high recoveries. Ionic liquid in combination with por-
graph was linear between 0.1 and 100 g mL1, with a phyrin complexing reagent was successfully applied in this
correlation coefficient of 0.9995. The regression equation study for the extraction and preconcentration of Hg(II).
was y05.7815+550.33, where y is fluorescence intensity Likewise, a fast and quantitative back extraction of the
and x is mercury concentration in g mL1. LOD for mercury analyte from room temperature ionic liquid phase into aque-
was defined as the concentration at which the signal is equal to ous phase was possible, allowing its further determination
the blank signal plus 3 and found to be 0.08 g mL1 for the by spectrofluorimetry. It has to be pointed out that, although
preconcentration of 20 mL of sample solution. The method effective, room temperature ionic liquid -mediated extrac-
developed in this work is developed for mercury determina- tion is mostly a batch process and further efforts focused on
tion at trace levels. Thus, RTIL based analytical method could automating the extraction process using flow injection or

Table 2 Comparison of other cloud point extraction methods given for mercury in literature

Surfactant Reagent PF RSD (%) Determination method Reference

Triton X-114 TMK 33 0.27 Uv-visible [24]

PONPE 5 5-Br-PADAP 200 3.4 ICP-OES [25]
Triton X-114 MG 18 3.6 ICP-OES [7]
Triton X-114 DDTC 42 1.08 HPLC/ICP-MS [26]
PONPE 7.5 5-Br-PADAP 22 4.0 ETAAS [27]
[C4 mim][PF6] 5-Br-PADAP 36 2.8 CVAAS [28]
Triton X-114 PAN 52 2.0 ICP-MS [29]
TritonX-100 Dithizone 6 4.8 Uv-visible [30]
Triton X-114 DDTP 12 4.6 CVAAS [31]
TEGII TPPP 45 2.4 Fluorimetry This

PF Preconcentration factor, Triton X-114: octylphenoxypolyethoxyethanol, PONPE 5: polyethyleneglycolmono-p-nonylphenylether, [C4mim]

[PF6]: 1-butyl-3-methylimidazolium hexafluorophosphate, TMK Thio-Michlers Ketone, MG methyl green, DDTC diethyldithiocarbamate, 5-Br-
PADAP: 5-bromo-2-pyridylazo)-5-Diethylaminophenol, PAN: 1-(2-pyridylazo)- 2-naphthol (PAN), DDTP: o,o-diethyldithiophosphate
52
sequential injection system need to be made to fully explore
the advantages of room temperature ionic liquid-mediated
extraction. The preconcentration method allowed mercury
determination in tap, river and mineral water samples at
trace levels with high accuracy and reproducibility.
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