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Synthesisof Schiffbasefunctionalizedsuperparamagnetic Fe 3 O4 Compositesforeffectiveremovalof PB IIand CD IIfromaqueoussolution
Synthesisof Schiffbasefunctionalizedsuperparamagnetic Fe 3 O4 Compositesforeffectiveremovalof PB IIand CD IIfromaqueoussolution
H I GH L IG H T S G R A P H I C A L A B S T R A C T
A R T I C LE I N FO A B S T R A C T
1. Introduction during the past few years [1,2]. Among these metal ions, Pb(II) and Cd
(II) are considered to be high toxic due to the non-biodegradability and
With the development of industrialization, water pollution aroused poisonousness to human and living beings [3]. The uptake of Pb(II)
by heavy metal ions had become a serious environmental problem would increase blood pressure and cause damage to the kidneys,
⁎
Corresponding author.
E-mail address: niuyuzhong@126.com (Y. Niu).
https://doi.org/10.1016/j.cej.2018.04.151
Received 3 March 2018; Received in revised form 20 April 2018; Accepted 21 April 2018
Available online 23 April 2018
1385-8947/ © 2018 Elsevier B.V. All rights reserved.
J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
nervous, and immune system [4]. While Cd(II) could cause renal da- base ligand was anchored on the surface of Fe3O4@SiO2. Homogeneous
mage, hypertension, and skeletal malformation [5]. Therefore, it is method involves one step reaction with solid support, has been proved
essential to remove Pb(II) and Cd(II) from aqueous solution. to be more efficient for the synthesis of silica gel adsorbents with better
Traditional methods including chemical precipitation, electro- adsorption properties [27,28]. However, little attention has been paid
plating, ion exchange, and membrane separation have been adopted for to the synthesis of Schiff base functionalized Fe3O4 composites by
the treatment of heavy metal ions [4]. Compared with these methods, homogeneous method and the adsorption behavior of the resulting
absorption is identified as one of the most promising methods due to its adsorbents.
simplicity, high efficiency, and cost-effectiveness [4,6]. Hence, various In the present study, Schiff base functionalized superparamagnetic
adsorbents have been constructed for the remediation of Pb(II) and Cd Fe3O4 composites (Fe3O4@SiO2-HO-S and Fe3O4@SiO2-HE-S) were
(II) pollution [7,8]. Superparamagnetic Fe3O4 has attracted extensive synthesized by homogeneous and heterogeneous methods, and their
attention due to its large surface area, high efficiency, low-cost, easy structures were fully characterized. The obtained adsorbents were ap-
functionalization and separation [9,10]. Therefore, the design and plied to remove Pb(II) and Cd(II) from aqueous solution by batch
synthesis of Fe3O4 based adsorbents still attract enormous interests. method. The effects of pH, time, temperature, and initial concentration
However, naked Fe3O4 particle usually suffers the drawbacks of on the adsorption of Pb(II) and Cd(II) were investigated systematically.
poor stability, aggregation and surface oxidation, which limit their The adsorption mechanism was revealed on the basis of experimental
application in metal ion separation and remediation [11,12]. To over- and theoretical calculation.
come these disadvantages, Fe3O4 particles are usually coated with
suitable substances to enhance their stability [13]. Such coating agents 2. Experimental
include silica, carbon, graphene oxide, and chitosan, etc. [14–17].
Among them, coating Fe3O4 by silica is widely employed as silica ex- 2.1. Materials and methods
hibited excellent thermal and chemical stability, well-modified surface
property to construct adsorbents to meet diverse requirements in Superparamagnetic Fe3O4 was prepared via co-precipitation method
practical applications [12,18]. For example, Li et al. synthesized ami- according to the similar procedure described in the reference [20,29].
doxime-functionalized silica coated Fe3O4 (Fe3O4@SiO2) and used for Tetraethoxysilane (TEOS), Salicylicaldehyde (SA), and other regents
the removal of U(VI) from aqueous solutions, which exhibited enhanced were analytical grade and purchased from Sinopharm Chemical Re-
adsorption amount compared with bare Fe3O4@SiO2 [19]. Roto et al. agent Co., Ltd. APTES was provided by Qufu Wanda Chemicals Factory.
described the introduction of thiol group on the surface of Fe3O4@SiO2 Toluene need to be distilled before use, while other regents were used
for effective chloroauric ([AuCl4]−) adsorption [20]. Schiff base ligand as received.
that formed by the reaction of amine group with active carbonyl group Fourier Transform Infrared Spectroscopy (FTIR) was performed on a
bears both nitrogen and oxygen donor atoms, have been proved to have Nicolet iS50 (Thermo Fisher Scientific). The morphology of the ad-
excellent binding ability for metal ions [21–23]. Thus, the introduction sorbents was observed on Hitachi S-4800 field emission scanning
of Schiff base ligand to the surface of Fe3O4 would combine the virtues electron microscope (SEM) and field emission transmission electron
of both components, which provide the feasibility to construct ad- microscope (TEM, FEI TF 20). Elemental analysis was conducted by
sorbents with high efficiency. The diversity of amine and carbonyl Elementar vario EL cube. Thermogravimetric analysis (TGA) was per-
compounds enables to construct various Schiff base functionalized formed on NETZSCH STA409PC. The wide-angle X-ray diffraction
Fe3O4 adsorbents. For example, Yuvaraja et al. reported the synthesis of (XRD) was recorded by Rigaku D/max-2500VPC. Porous structure
superparamagnetic Fe3O4 supported chitosan-4-((pyridin-2-ylimino) analysis was determined by the ASAP 2020 analyzer. The concentration
methyl)benzaldehyde Schiff base for the removal of Pb(II) [24]. Mor- of metal ion was detected by VARIAN AA240 atomic adsorption spec-
adinasab et al. reported the use of Schiff base modified Fe3O4@SiO2 trophotometer (AAS).
that formed by salicylaldehyde to remove Cu(II), Zn(II), and Ni(II) [25].
Setoodehkhah et al. synthesized water soluble Schiff base functiona-
2.2. Synthesis of Schiff base functionalized superparamagnetic Fe3O4
lized Fe3O4 nanoparticles by sodium salicylaldehyde-5-sulfonate to re-
composites (Fe3O4@SiO2-HO-S and Fe3O4@SiO2-HE-S)
move Pb(II) and Cu(II) [26]. The present method adopted for the
synthesis of Schiff base functionalized Fe3O4 composites generally in-
Fe3O4@SiO2-HO-S and Fe3O4@SiO2-HE-S were prepared according
volves two steps reaction with the solid Fe3O4@SiO2, which attributed
to the procedures depicted in Scheme 1.
to heterogeneous method. The method involves the introduction of
amino group by the reaction of 3-aminopropyltriethoxysilane (APTES)
with Fe3O4@SiO2 and the subsequent reaction of amino group with 2.2.1. Synthesis of Fe3O4@SiO2
active carbonyl compounds [25,26]. As an alternative method, homo- Fe3O4@SiO2 was synthesized according to the similar procedure
geneous method allows the reaction of APTES with active carbonyl described in previous report [13]. 5.0 g Fe3O4 was dispersed in a mix-
compounds first to form Schiff base ligand, and then the resulting Schiff ture of 100 mL distilled water and 100 mL ethanol by ultrasonication
for 1 h. The pH of the suspension was adjusted to 10 by ammonia
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J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
the solution.
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J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
Fig. 2. The SEM (a), TEM (b) images and lattice fringes (c) of Fe3O4@SiO2-HO-S.
Fig. 3. TGA curves of Fe3O4 (1), Fe3O4@SiO2 (2), Fe3O4@SiO2-HE-S (3), and
Fe3O4@SiO2-HO-S (4).
577
J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
where B is time constant, n is the integer that defines the infinite series
solution and F is the equilibrium fractional attainment at time t. F can
be calculated by Eq. (5):
Fig. 5. Nitrogen adsorption–desorption isotherms of Fe3O4@SiO2, Fe3O4@SiO2- qt
HO-S, and Fe3O4@SiO2-HE-S. F=
qe (5)
Table 1 where qe and qt are the equilibrium and the adsorption amount at time t
The parameters of porous structure of Fe3O4@SiO2, Fe3O4@SiO2-HO-S, and (mmol·g−1), respectively.
Fe3O4@SiO2-HE-S. The Bt value can be obtained by the corresponding F value [46]. The
fitting plots of Bt versus t can be used to determine the rate controlling
Adsorbent BET surface BJH desorption BJH desorption
area (m2·g−1) cumulative volume of average pore radius
step. If the fitting curve exhibits good linearity and pass through the
pores (cm3·g−1) (nm) origin, the adsorption is controlled by intraparticle diffusion process.
Otherwise, if the fitting curve do not pass through the origin, film
Fe3O4@SiO2 71.58 0.23 71.87 diffusion process is the rate controlling step [46]. The linear equations
Fe3O4@SiO2- 42.02 0.20 57.67
HE-S
and the corresponding parameters of Bt versus t plots were shown in
Fe3O4@SiO2- 31.02 0.15 33.71 Table 3. It is evident that the lines of the Bt versus t plot exhibited
HO-S excellent linearity and do not pass through the origin, indicating the
adsorption process of Fe3O4@SiO2-HO-S and Fe3O4@SiO2-HE-S for Pb
(II) and Cd(II) was controlled by film diffusion mechanism.
3.2. Adsorption kinetic
3.3. The effect of pH on the adsorption
The adsorption kinetic curves of Fe3O4@SiO2-HO-S and Fe3O4@
SiO2-HE-S for Pb(II) and Cd(II) at different concentration were shown in
The effect of pH on the adsorption of Pb(II) and Cd(II) was shown in
Fig. 6. As can be seen from Fig. 6, the equilibrium adsorption capacity
Fig. 7. It is evident that the adsorption capacity of Fe3O4@SiO2-HO-S
of Fe3O4@SiO2-HO-S for both Pb(II) and Cd(II) are higher than Fe3O4@
and Fe3O4@SiO2-HE-S for Pb(II) and Cd(II) increased with the increase
SiO2-HE-S at different concentration due to higher content of functional
of solution pH, and the maximum adsorption for both ions appeared at
group Fe3O4@SiO2-HO-S possessed. It can also observed that the ad-
pH 6. At low pH, the functional groups of –N] and –OH was proto-
sorption of Pb(II) and Cd(II) was very rapidly in the first 150 min, then
nated due to the presence of H+, the electrostatic repulsion between
the adsorption rate gradually slow down and equilibrium was reached
positively charged functional group and metal ion prevented the con-
at about 270 and 210 min for Pb(II) and Cd(II), respectively. In the
tact of Pb(II) and Cd(II) to coordinate with the adsorbents, resulting in
initial adsorption stage, the rapid adsorption rate attributed to the
the low adsorption capacity [18,47]. With the increase of pH, the
higher concentration of metal ion and abundant available binding sites
concentration of H+ decreased and the protonation of functional group
of the adsorbent, which facilitate the binding of metal ion with ad-
decreased accordingly, leading to the increase of available binding
sorbent. With the adsorption proceeding, both the metal ion con-
sites. Hence, the adsorption capacity increased accordingly. However,
centration and available binding sites were decreased. The decreased
when pH was more than 6, Pb(II) and Cd(II) would be hydrolyzed to
concentration gradient made it difficult for metal ion to diffusion to the
produce hydroxide precipitation [4,48]. Therefore, this condition is
surface of the adsorbent, leading to the decrease of adsorption rate
often not desirable and the optimum adsorption pH is 6 for both Pb(II)
gradually until the equilibrium was reached.
and Cd(II).
The kinetic data were fitted by pseudo-first-order, pseudo-second-
order, and Boyed film diffusion models to reveal the adsorption kinetic
mechanism. The linear forms of pseudo-first-order and pseudo-second- 3.4. Isotherm adsorption
order model can be described as Eqs. (2) and (3) [41–44].
The isotherm adsorption data is very important for describing the
ln(qe−q) = lnqe−k1 t (2) state of adsorption equilibrium, and it provides the basic information
about thermodynamic performance [4]. The isotherm adsorption
t 1 1 curves of Fe3O4@SiO2-HO-S and Fe3O4@SiO2-HE-S for Pb(II) and Cd(II)
= + t
q k2 qe2 qe (3) were showed in Fig. 8. It is clearly shown that the adsorption amount
increased with the increase of initial metal ion concentration and
where qe and q are the equilibrium and instant adsorption amount temperature. The adsorption amount increased with the increase of
(mmol·g−1), k1 (min−1) and k2 (g·mmol−1·min−1) are the rate constant temperature indicated the adsorption process was endothermic process.
of pseudo-first-order and pseudo-second-order model, respectively. The The increased of adsorption capacity associate with initial metal ion
fitting results were listed in Table 2. According to Table 2, The concentration suggested the adsorption favored high concentration due
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J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
Fig. 6. Adsorption kinetic curves of Fe3O4@SiO2-HO-S and Fe3O4@SiO2-HE-S for Pb(II) and Cd(II) at different concentration.
to the larger driving force arise from high concentration gradient. Table 3
In order to reveal the isotherm adsorption mechanism, Langmuir, The linear equations and corresponding parameters of Bt versus t plots.
Freundlich, and Dubinin-Radushkevich (D-R) models were employed to Adsorbent Ion C(mol·L−1) Linear equation Intercept R2
analyze the isotherm adsorption data [18,30]. Langmuir model describe error
single molecular layer adsorption on the uniform surface with a finite
number of identical sites of the adsorbent, the linear equation of Fe3O4@ Cd(II) 0.002 Bt = 0.0082 t + 0.1827 0.0409 0.9768
SiO2- 0.004 Bt = 0.0052 t + 0.0631 0.0158 0.9914
Langmuir model can be described by Eq. (6): HE-S Pb(II) 0.002 Bt = 0.0129 t − 0.4601 0.0529 0.9878
0.004 Bt = 0.0168 t − 0.3820 0.0678 0.9801
Ce C 1
= e + Fe3O4@ Cd(II) 0.002 Bt = 0.0120 t − 0.2722 0.0855 0.9894
qe qm qm KL (6) SiO2- 0.004 Bt = 0.0111 t − 0.3638 0.0844 0.9756
HO-S Pb(II) 0.002 Bt = 0.0173 t − 0.5311 0.1325 0.9892
where Ce (mmol·ml−1) and qe (mmol·g−1) are the equilibrium con- 0.004 Bt = 0.0112 t − 0.1620 0.0601 0.9788
centration of metal ion and adsorption amount, respectively; qm
(mmol·g−1) is the maximum adsorption amount; KL (mL·mmol−1) is the
Langmuir constant.
Freundlich model is used to describe the multilayer adsorption of
Table 2
The fitting parameters of pseudo-first-order and pseudo-second-order model.
Adsorbent Ion C (mol·L−1) qe,exp (mmol·g−1) Pseudo-first-order Pseudo-second-order
Fe3O4@SiO2-HE-S Cd(II) 0.002 0.18 0.71 0.0382 0.6312 0.17 0.2101 0.9984
0.004 0.21 1.34 0.0378 0.5785 0.21 0.0082 0.9716
Pb(II) 0.002 0.23 1.54 0.0420 0.6420 0.27 0.0874 0.9812
0.004 0.24 2.21 0.0436 0.7574 0.31 0.0347 0.9930
Fe3O4@SiO2-HO-S Cd(II) 0.002 0.24 2.46 0.0381 0.6235 0.33 0.0405 0.9815
0.004 0.33 3.56 0.0413 0.5887 0.40 0.0321 0.9860
Pb(II) 0.002 0.25 0.62 0.0374 0.7128 0.27 0.0903 0.9910
0.004 0.36 3.59 0.0490 0.7139 0.41 0.0562 0.9890
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J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
non-uniform surfaces, the linear equation of Freundlich model can be Langmuir model with monolayer adsorption behavior. In addition, the
expressed by Eq. (7): qm calculated from Langmuir model was much closer to the experi-
mental value, further demonstrate the adsorption process could be well
lnCe fitted by Langmuir model. The comparison of qm with other alternative
lnqe = lnKF +
n (7) adsorbents was presented in Table 5. It can be seen that Fe3O4@SiO2-
HO-S and Fe3O4@SiO2-HE-S exhibited relative larger adsorption capa-
where KF (mmol·g−1) is the Freundlich constant and n is adsorption city than most of the adsorbents, and could be potentially used as
intensity index (dimensionless) related to the adsorption intensity. promising candidates for the separation and preconcentration of Pb(II)
The fitting parameters of Langmuir and Freundlich models were and Cd(II) from aqueous solution.
listed in Table 4. It can be seen that the correlation coefficient of D-R model was employed to identify whether the adsorption is
Langmuir model (RL2) were all higher than Freundlich model (RF2), physical or chemical in nature [59,60]. The linear equation of D-R
indicating the uptake of Pb(II) and Cd(II) can be well described by
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Table 4
The fitting parameters of Langmuir and Freundlich model.
Adsorbent Ion T (°C) Langmuir Freundlich
−1 −1
qm (mmol·g ) KL (mL·mmol ) RL 2
KF (mmol·g−1) n RF2
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J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
Table 6
The fitting parameters of D-R model.
Adsorbent Ion T (°C) Linear equation qm (mmol·g−1) k (mol2·J−2) E (kJ·mol−1) R2
Fe3O4@SiO2-HE-S Cd(II) 15 y = −3.02 · 10−9x + 0.17 1.21 3.02 · 10−9 12.81 0.9861
25 y = −4.65 · 10−9x + 0.60 1.83 4.06 · 10−9 11.11 0.9974
35 y = −4.06 · 10−9x + 0.81 2.20 4.25 · 10−9 10.92 0.9986
Fe3O4@SiO2-HE-S Pb(II) 15 y = −3.83 · 10−9x + 0.01 1.02 3.83 · 10−9 11.45 0.9665
25 y = −4.66 · 10−9x + 0.44 1.62 4.66 · 10−9 10.42 0.9280
35 y = −3.74 · 10−9x + 0.53 1.71 3.74 · 10−9 11.67 0.9834
Fe3O4@SiO2-HO-S Cd(II) 15 y = −3.86 · 10−9x + 0.28 1.31 3.86 · 10−9 11.45 0.9867
25 y = −2.20 · 10−9x + 0.64 1.92 4.22 · 10−9 10.93 0.9957
35 y = −3.98 · 10−9x + 0.70 2.01 3.98 · 10−9 11.38 0.9923
Fe3O4@SiO2-HO-S Pb(II) 15 y = −3.67 · 10−9x + 0.78 2.27 3.67 · 10−9 11.68 0.9996
25 y = −3.86 · 10−9x + 0.80 2.29 3.86 · 10−9 11.45 0.9954
35 y = −4.89 · 10−9x + 0.94 2.61 4.89 · 10−9 10.17 0.9967
Table 7 between N atom and Pb(II) dominated the adsorption, while O atom
The thermodynamic parameters of the adsorption. also participate in the coordination. Similar phenomenon was observed
Adsorbent Ion T (°C) ΔG (kJ·mol−1) ΔH (kJ·mol−1) ΔS (J·mol−1·K−1)
in the complex of Cd(II), the E(2) stabilization energies of LP(N) →
LP∗(Pb) and LP(O) → LP∗(Pb) were 47.93 and 10.78 kcal/mol, respec-
Fe3O4@ Cd(II) 15 −11.50 22.11 116.45 tively. It can observed that the E(2) stabilization energies of Pb(II)
SiO2- 25 −12.23 complex were higher than Cd(II) complex, implying the binding ability
HO-S 35 −13.16
of the adsorbent for Pb(II) was stronger than Cd(II), which is consistent
Fe3O4@ Pb(II) 15 −10.89 12.96 82.80 with the experimental results as both Fe3O4@SiO2-HO-S and Fe3O4@
SiO2- 25 −11.76
SiO2-HE-S exhibited relative higher adsorption capacity for Pb(II).
HO-S 35 −11.85
In order to make the DFT calculation more close to the adsorption
Fe3O4@ Cd(II) 15 −12.67 27.35 138.53
process, the coordination geometries of Pb(II) and Cd(II) with two
SiO2- 25 −13.26
HE-S 35 −14.82 Schiff base ligands were optimized and presented in Fig. 11. It is clearly
that the two Schiff base ligands also tend to bind Pb(II) and Cd(II) by
Fe3O4@ Pb(II) 15 −15.04 7.89 79.57
SiO2- 25 −15.84
nitrogen and oxygen atoms to form quadri-coordianted complexes,
HE-S 35 −15.99 which is similar to the complexes formed by single Schiff base ligand.
The bond distances of N–Pb, N–Cd, O–Pb, and O–Cd become longer
than the single Schiff base ligand complexes due to the steric hindrance
caused by the presence of two Schiff base ligands. The NBO partial
charge of Pb(II) and Cd(II) in the complexes were 1.55 and 1.68, and
the electron configuration of Pb(II) and Cd(II) were 6s1.916p0.537p0.01
and 5s0.324d9.985p0.01, respectively. The results further indicated charge
transfer from Schiff base ligand to metal ion occurred during the ad-
sorption. The transferred electron was mainly from Schiff base ligands
to the 6s and 6p empty orbital of Pb(II), and the 5s empty orbital of Cd
(II), which is consistent with the result obtained from the complex of
single Schiff base ligand with Pb(II) and Cd(II).
4. Conclusion
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J. Zhao et al. Chemical Engineering Journal 347 (2018) 574–584
Fig. 10. Optimized geometries of Schiff base ligand with Pb(II) and Cd(II) complexes.
Fig. 11. Optimized geometries of Pb(II) and Cd(II) complexes with two Schiff base ligands.
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