1. Introduction
The sixteen polycyclic aromatic hydrocarbons
(PAHs) in the United States environmental
protection agency and European community (US,
EPA) are considered as priority pollutants [1, 2]
The
PAHs are toxic organic contaminants with great
environmental and health concern, which consist of
two or more fused aromatic rings. PAHs containing
up to two fused benzene rings such as anthracene
and phenanthrene are known as light PAHs and
those containing more than four benzene rings
such as ovalene and corannulene are called heavy
PAHs[3]. The main source of PAHs contamination
is incomplete combustion and pyrolysis of wood
or fossil fuels, the motor oil and petroleum spill
which are disposed of improperly each year into
soil[4]. Owing to the persistence of PAHs in soil
Anal. Methods Environ. Chem. J. 4 (3) (2021) 47-58
Research Article, Issue 3
Analytical Methods in Environmental Chemistry Journal
Journal home page: www.amecj.com/ir
AMECJ
A novel modied fenton-like process for efcient
remediation of anthracene-contaminated soils before
analysis by ultraviolet–visible spectroscopy
Mahdia Hamidinasab
a,b,*
, Mohammad Ali Bodaghifard
a,b
, Sepideh Ahmadi
b
, Ali Seif
a
and Zahra Najahi Mohammadizadeh
a
a
Department of Chemistry, Faculty of Science, Arak University, Arak 88138-38156, Iran.
b
Institute of Nanosciences and Nanotechnology, Arak University, Arak 88138-38156, Iran.
ABSTRACT
Due to the persistence of polycyclic aromatic hydrocarbons (PAHs)
in soil and sediments, and their toxic, mutagenic, and carcinogenic
effects, the remediation of PAH-contaminated sites is an important
role for environment pollution. In this study, the chemical oxidative
remediation of anthracene-contaminated soils was investigated by
magnetite nanoparticles (Fe
3
O
4
) catalyzed Fenton-like oxidation in
the presence of hydrogen peroxide 30% (H
2
O
2
) and urea-hydrogen
peroxide (UHP) at neutral pH. Urea-hydrogen peroxide (UHP), as a
safer oxidizing agent, is used for the rst time in the Fenton process.
The magnetite nanoparticles improved the production of hydroxyl
radicals, and the removal of polycyclic aromatic hydrocarbons
(anthracene as a model compound) from the soil samples. The
structure of Fe
3
O
4
nanoparticles was characterized by Fourier-
transform infrared spectroscopy (FT-IR), X-ray powder diffraction
(XRD), scanning electron microscopy (SEM), and vibrating sample
magnetometer (VSM). The removal efciency of anthracene at an
initial concentration 2500 (mg kg
-1
) was 95% for 2.5 mmol by using
hydrogen peroxide and 93% for 0.1 mmol of UHP at the optimum
oxidation condition. The anthracene reaction was analyzed by
ultraviolet-visible spectroscopy (UV-Vis). The UHP safety and
efciency, neutral pH condition, the limited iron leaching and its easy
magnetic separation makes magnetite nanoparticles-UHP a promising
catalytic system in remediation of polycyclic aromatic hydrocarbons
in contaminated soils.
Keywords:
Polycyclic aromatic hydrocarbon (PAH),
Remediation, Modied Fenton’s
reaction,
Magnetite nanoparticle,
Urea-hydrogen peroxide (UHP)
ARTICLE INFO:
Received 20 May 2021
Revised form 30 Jul 2021
Accepted 17 Aug 2021
Available online 30 Sep 2021
*Corresponding Author: Mahdia Hamidinasab
Email: mahdiahamidinasab@yahoo.com
https://doi.org/10.24200/amecj.v4.i03.140
------------------------
48
and sediments, and their toxic, mutagenic, and
carcinogenic effects, the remediation of PAH-
contaminated sites is an important environmental
issue. Various remediation techniques including
incineration, thermal conduction, solvent
extraction/soil washing, chemical oxidation, bio-
augmentation, bio-stimulation, phytoremediation,
composting/bio-piles and bioreactors have been
explored and studied for the removal of persistent
PAHs from complex matrices like soil or sediments.
Integrating physico-chemical and biological
technologies is also widely practiced for better
clean-up of PAH contaminated soils. Electrokinetic
remediation, vermiremediation and biocatalyst
assisted remediation are at the development stage[5]
In situ chemical oxidation (ISCO) has emerged as
a cost-effective and viable remediation technology
for the treatment of several pollutants in ground
waters, soils and sediments[6–8]. Remediation by
chemical oxidation involves the injection of strong
oxidants such as hydrogen peroxide[9], ozone
gas[10], potassium permanganate[11], etc. In last
two decades a lot of researches have been addressed
to this aim and pointed out the prominent role of
a special class of oxidation techniques dened
as advanced oxidation processes (AOPs), which
usually operated at or near ambient temperature and
pressure[12, 13]. Advanced oxidation processes
(AOPs) are attracting signicant attention
because of their effective and rapid degradation
performance, including photocatalysis [4, 14, 15],
ozonisation[16], electrochemical reactions[17]
and Fenton method[18, 19]. Among chemical
oxidation processes, special attention has been paid
to the use of Fenton’s reagent, which release the
hydroxyl radicals with high oxidation potential
(E
°
=2.73 V), from the catalytic decomposition of
H
2
O
2
in the presence of Fe (II) or Fe (III) ions. The
Fenton method has the ability to oxidize a wide
range of organic pollutants and convert them to
CO
2
, H
2
O and inorganic compounds or, at least,
transform them into harmless or biodegradable
products[20–23].
This conventional Fenton’s
process is limited by the optimum pH (~3), such
as at low pH results in negative impacts on soil
properties and is incompatible with subsequent
biodegradation. In the novel process as known as
Fenton-like oxidation, the iron minerals or organic
chelating agents can be applied to extend its range
of applicability at circumneutral soil pH. The
degradation of PAHs has been reported by Fenton-
like reaction catalyzed by various Fe (III) oxides
like ferrihydrite, hematite or goethite[24–26].
Recently, Fe(II) bearing minerals such as magnetite
(Fe
3
O
4
) were found to be the most effective
nanocatalyst as compared to the only Fe(III)
oxides for heterogeneous catalytic oxidation of
organic pollutants[26-29]. The researchers must
be very careful when dispensing oxidizers from
storage containers, avoid spilling material and
contaminating their skin or clothing which can
cause serious accidents. Urea-hydrogen peroxide
(UHP) contains solid and water-free hydrogen
peroxide, which offers a higher stability and better
controllability than liquid hydrogen peroxide
when used as an oxidizing agent. Urea-hydrogen
peroxide adducts (UHP) is stable, inexpensive and
an easily handled reagent. So, the UHP is used as a
solid state agent for efcient oxidation of different
organic molecules.
In this study, the anthracene as a model polycyclic
aromatic hydrocarbon was removed from
contaminated soil by a modied Fenton’s reaction,
using hydrogen peroxide and urea-hydrogen
peroxide separately in the presence of bare
magnetite nanoparticles (Fe
3
O
4
) as a nanocatalyst
at circumneutral soil pH.
2. Experimental
2.1. Materials and apparatus
Anthracene 96% (CAS 120-12-7) and H
2
O
2
30%
(CAS 7722-84-1) were used as a contaminant and
oxidant respectively. Ethanol 99.7% (CAS 64-
17-5), Iron (II) chloride tetra hydrate 99% (CAS
13478-10-9) and Iron (III) chloride hexahydrate
98% (CAS 10025-77-1) were purchased from
Merck Company. All reagents were used without
further purication. The FT-IR spectra were
recorded on Bruker Alpha spectrophotometer in the
region 400-4000 cm
-1
using pressed KBr discs. The
Anal. Methods Environ. Chem. J. 4 (3) (2021) 47-58
49
eld emission-scanning electron microscopy (FE-
SEM) was carried out by a MIRA III TESCAN-
XMU. The hysteresis loop was measured at
room temperature using a vibrating sample
magnetometer (Model 7300 VSM system, Lake
Shore Cryotronic, Inc., Westerville, OH, USA).
The UV-Vis spectrophotometer (Agilent 8453) was
used to determine the oxidation process.
2.2. Soil Samples
Crushing and preparing of the samples was
performed at geology department of Kharazmi
University (Iran, Tehran) and powdering was done
at the Iranian mineral processing research center
(IMPRC). The analysis of whole-rock major and
trace elements was conducted at ETH, Zurich. The
major elements are summarized in Table 1.
2.3. Preparation of Fe
3
O
4
nanoparticles
Magnetite nanoparticles (MNPs) was synthesized
by co-precipitation method [31]. Aqueous solutions
of FeCl
3
.6H
2
O (56 mmol) and FeCl
2
.4H
2
O (28
mmol) were prepared in de-ionized water (25 mL)
and NaOH (3 M) solution was added to it slowly
and stirred continuously using a magnetic stirrer to
reach the pH=12. This solution was heated under N
2
atmosphere at 90 °C for 4 hours. The mixture was
ltered and washed 3 times with deionized water
DW/ ethanol before dried at 60 ºC (Equation 1).
FeCl
2
.4
H
2
O
+
2FeCl
3
.6
H
2
O
+
8NH
4
OH
N
2
atmosphere
Water,
90
°C
Fe
3
O
4
+
8NH
4
Cl
+
20H
2
O
FeCl
2
.4
H
2
O
+
2FeCl
3
.6
H
2
O
+
8NH
4
OH
N
2
atmosphere
Water,
90
°C
Fe
3
O
4
+
8NH
4
Cl
+
20H
2
O
(Eq. 1)
2.4. Calibration curve
Figure 1 shows the UV-Vis absorption spectra
and calibration curve of anthracene for different
concentration. The absorption coefcient (ε) obtained
by using the Lambert-Beer’s law (Equation 2) [32].
(Eq. 2)
Anthracene removal from soils by Fe3O4-Fenton process Mahdia Hamidinasab et al
Table 1. Total elemental analyses of soil sample.
Compound SiO
2
TiO
2
Al
2
O
3
Fe
2
O
3
FeO MnO MgO CaO Na
2
O K
2
O P
2
O
3
Wt.% 56.84 0.69 16.84 0.90 5.98 0.11 2.15 6.20 4.38 1.93 0.19
Fig. 1. UV-Vis absorption spectra and calibration curve of anthracene
in the wavelength range 200-400 nm
50
2.5. Preparation of anthracene-contaminated soil
Soil samples was prepared as detailed in the
literature,[33] where an ethanol solution with
approximately 500 mg of anthracene was distributed
and mixed manually onto 20 g of clean soil with a
spatula which was homogenized.
2.6. Procedure od anthracene extraction
All experiments were carried out without pH
adjustment and the experiments were done
on a laboratory scale. All experimental runs
were performed at room temperature. For all
experiments, 1 gr (dry mass) of contaminated soil
sample was placed in the tube, 2 mL of deionized
water (DW) was added, followed by the required
quantities of oxidants (H
2
O
2
and urea- H
2
O
2
)
and magnetite as a nanocatalyst (Table 2). The
samples were shacked for 30 minutes. The residual
anthracene in the soil sample was extracted in 8
mL of ethanol during 10 minutes and controlled
the tube centrifugation for 15 min at 3000 rpm.
The presence of anthracene in the solutions was
analyzed by UV-Vis spectrophotometer (λ
max
=250
nm). Figure 2 illustrates the oxidation process of
anthracene in modied Fenton’s reaction. The
quantify decomposition of anthracene in soil was
shown in Equation 3 as follows,
(Eq. 3)
Where X
Anthracene
is the percentage of anthracene
decomposed in soil, C
0
and C
t
are the initial and
nal concentration of anthracene at a given time.
3. Result and discussions
3.1. Characterizations
The Fe
3
O
4
nanoparticles were carefully prepared[34]
and characterized by Furrier-transform infrared
spectroscopy (FT-IR), X-ray powder diffraction
(XRD), scanning electron microscopy (SEM),
and vibrating sample magnetometer (VSM).
The X-ray diffraction analysis (XRD) of Fe
3
O
4
nanoparticles shows several diffraction peaks at
2θ = 30.54, 35.89, 43.9, 54.28, 57.55, 63.3 and
74.33 that attributed to the miller planes 220, 311,
400, 422, 511, 440 and 533 respectively (Fig. 3a).
These results are in accordance with the standard
patterns (JCPDS CardNo. 85-1436)[34] The FT-
IR spectra of Fe
3
O
4
MNPs is shown in Figure 3b.
The appeared vibrational frequencies in the 584-
631 cm
-1
region are attributed to the Fe-O bonds.
Anal. Methods Environ. Chem. J. 4 (3) (2021) 47-58
Fig. 2. The oxidation process of anthracene in modied Fenton’s reaction
51
The stretching frequencies of hydroxyl groups,
on the surface of the nanoparticles, appeared
at 3420 cm
-1
and the peak in the 1625 cm
-1
are
related to the bending vibrations of OH groups.
The morphology and particle size distribution of
Fe
3
O
4
nanoparticles was performed by FE-SEM
technique. The average size of nanoparticle is
32 nm and confirm the spherical and regular
shape of nanoparticles (Fig. 3c). The magnetic
properties of the synthesized nanoparticles were
determined by VSM at room temperature, which
contains the magnetization curve (M) in terms of
the applied magnetic field (H) (hysteresis curve)
of Fe
3
O
4
MNPs particles which shows the great
paramagnetic properties (Fig. 3d).
3.2. The optimization of H
2
O
2
, urea-hydrogen
peroxide and magnetite values
A different combination of magnetite and hydrogen
peroxide was selected for optimization (Table 2).
First, the effect of varying H
2
O
2
and urea-hydrogen
peroxide concentrations on anthracene removal
efciency was investigated while the amount of
magnetite was kept constant (Fig. 4). As H
2
O
2
and UHP concentration rises, the removal of
anthracene is increased and nally leveled off. The
maximum removal efciency of 95% at 0.2 mL
H
2
O
2
concentration and 93% at 6 mg UHP content
was observed, respectively. Therefore, the H
2
O
2
and UHP concentrations was optimized for further
experiments. In the next stage, the effect of various
amounts of magnetite on the Fenton oxidation of
anthracene was investigated at optimum H
2
O
2
concentration of 0.2 mL (2.5 mmol) and 6 mg
UHP. The removal efciency was increased with an
increase in magnetite dosage up to 8 mg, and then
was remained constant at higher concentrations
(Fig. 5). The anthracene removal reached 93% at
the optimum concentration levels of H
2
O
2
, UHP,
and magnetite.
Anthracene removal from soils by Fe3O4-Fenton process Mahdia Hamidinasab et al
Fig. 3. The XRD spectra (a), The FT-IR spectra (b), The FE-SEM image (c)
and The VSM (d) of Fe
3
O
4
nanoparticles
52
Anal. Methods Environ. Chem. J. 4 (3) (2021) 47-58
Table 2. Optimization of combination of magnetite and hydrogen peroxide
Urea-
H
2
O
2
(mg)
Magnetite
(mg)
Samples
H
2
O
2
(ml)
Magnetite (mg)SamplesEntry
310M
10
-UHP
c
3
0.110M
a
10
-H
b
0.1
1
38M
8
-UHP
3
0.18M
8
-H
0.1
2
36M
6
-UHP
3
0.16M
6
-H
0.1
3
610M
10
-UHP
6
0.210M
10
-H
0.2
4
68M
8
-UHP
6
0.28M
8
-H
0.2
5
66M
6
-UHP
6
0.26M
6
-H
0.2
6
1010M
10
-UHP
10
0.310M
10
-H
0.3
7
108M
8
-UHP
10
0.38M
8
-H
0.3
8
106M
6
-UHP
10
0.36M
6
-H
0.3
9
1510M
10
-HUP
15
0.410M
10
-H
0.4
10
158M
8
-UHP
15
0.48M
8
-H
0.4
11
156M
6
-UHP
15
0.46M
6
-H
0.4
12
2010M
10
-UHP
20
---13
208M
8
-UHP
20
---14
206M
6
-UHP
20
---15
a
Magnetite,
b
H
2
O
2
30%
,
c
Urea-H
2
O
2
(UHP)
Fig. 4. The anthracene removal efciency in varying (a) H
2
O
2
concentrations
of 0.1-0.4 mL (b) UHP 0.1-0.4 mg (reaction time of 30 min, pH=7 and magnetite concentration of 8 mg)
53
Anthracene removal from soils by Fe3O4-Fenton process Mahdia Hamidinasab et al
Fig. 5. The anthracene removal efciency varying Fe
3
O
4
content in optimized (a) H
2
O
2
and (b) UHP
concentration (reaction time of 30 min and pH=7)
3.3. The effect of contact time on anthracene
removal
The effect of reaction time on anthracene removal at
optimum H
2
O
2
or UHP and magnetite concentration
was investigated (Fig. 6).
The reaction time positively affected the removal
efciency and the anthracene removal of 98%
was achieved after 30 min of contact time. After
24 h, about 99% conversion was achieved for all
contaminants.
54
3.4. The blank experiments
After the remediation experiments, two blank
tests were performed. In a sample experiment, 2
ml of deionized water was used without adding
the magnetite and hydrogen peroxide (blank 1) to
contaminated soil. In other sample, only 0.2 mL
H
2
O
2
without magnetite was added (blank 2) to
contaminated soil. The evolution of the conversion
of anthracene in blank 1 and blank 2 is shown in
Figure 7. In the blank 1, the degradation is attributed
to the natural attenuation during the reaction period
(45 days). It is shown the low anthracene content
(20%) in the soil was remediated during 45 days,
which is attributed to biodegradation of anthracene.
Anal. Methods Environ. Chem. J. 4 (3) (2021) 47-58
Fig. 6. The effect of contact time on anthracene removal in optimum H
2
O
2
,
UHP and magnetite concentrations at pH=7
55
The comparative study confirmed the Fenton-
like oxidation capability of the magnetic
nanoparticles for efficient degradation of
anthracene using 8 mg of the nanocatalyst, 0.2
mL H
2
O
2
30 % (2.5 mmol) and 6 mg urea-H
2
O
2
(0.1 mmol) at neutral pH as optimum operational
parameters under mild reaction conditions.
The solid urea-H
2
O
2
is
safer
than liquid H
2
O
2
(Fig. 8a). The magnetite (Fe
3
O
4
) is an efficient
nanocatalyst for the degradation of anthracene
and the urea-H
2
O
2
with lower content has a better
oxidizing effect than H
2
O
2
(Fig. 8b).
Anthracene removal from soils by Fe3O4-Fenton process Mahdia Hamidinasab et al
Fig. 7. The blank experiments in optimum oxidation condition
Fig. 8. (a) The sign of acute exposure of skin to hydrogen peroxide (H
2
O
2
30%)
(b) The comparison of H
2
O
2
and urea-H
2
O
2
as oxidants in Fenton’s method
56
4. Conclusions
In the present study, the Fenton-like oxidation
capability of the magnetite nanoparticles for the
efcient degradation of anthracene at neutral pH
under mild reaction conditions, was conrmed. The
urea-H
2
O
2
with lower content has a better oxidizing
effect than H
2
O
2
. Furthermore, the solid urea-H
2
O
2
is
safer
than liquid H
2
O
2
. The natural concentration
attenuation during the treatment time (45 days) was
less than 20% of the anthracene in soil. It was stated
that the magnetite nanocatalyst could activate
molecular oxygen via single-electron reduction
pathway to produce reactive oxygen species,
including hydroxyl radical (°OH), which are
capable of oxidizing contaminants. The generated
hydroxyl radicals oxidized the polycyclic aromatic
hydrocarbon contaminants by breaking them down
into non-toxic products. Therefore, the magnetite/
UHP system is a promising and environmentally
benign catalytic process for the remediation of
PAH-contaminated soils.
5. Acknowledgements
The Authors gratefully acknowledge the research
council of Arak University and department of
chemistry for providing the chemicals and apparatus.
6. Declaration of funding
The Authors gratefully acknowledge the partial
support from the research council of Arak
University.
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