Journal of Hazardous Materials 231232 (2012) 5763

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Journal of Hazardous Materials

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Removal of organic pollutants by surfactant modied zeolite: Comparison

between ionizable phenolic compounds and non-ionizable organic compounds
Jie Xie, Wenna Meng, Deyi Wu , Zhenjia Zhang, Hainan Kong
School of Environmental Science and Engineering, Shanghai Jiao Tong University, No. 800, Dongchuan Rd., Shanghai 200240, China

h i g h l i g h t s






Surfactant modied zeolite could greatly retain organic pollutants.

Uptake of organic compounds was due to the loaded surfactant.
kow is crucial for the uptake of both ionizable and non-ionizable organic solutes.
pKa is another factor affecting adsorption process of ionizable organic pollutants.
Adsorption mechanisms of the two kinds of organic pollutants were proposed.

a r t i c l e

i n f o

Article history:
Received 7 April 2012
Received in revised form 5 June 2012
Accepted 17 June 2012
Available online 26 June 2012
Keywords:
Zeolite
Surfactant
Removal
Organic pollutants
Adsorption

a b s t r a c t
The aim of this study was to examine the adsorption capability and mechanism of hexadecyltrimethylammonium modied zeolite, which was synthesized from coal y ash, for the removal of ionizable phenolic
compounds (phenol, p-chlorophenol and bisphenol A, with different pKa ) and non-ionizable organic
compounds (aniline, nitrobenzene, and naphthalene, with different hydrophobicity). The obtained zeolite was identied as type Na-P1 (Na6 Al6 Si10 O32 12H2 O, JCPDS code 39-0219), which is classied into
the gismondine group with a pore size of 3.1 A 4.5 A [1 0 0] and 2.8 A 4.8 A [1 0 1]. The adsorption
of the two kinds of organic compounds was due to loaded surfactant bilayer because modied zeolite
showed great ability for the removal of organic chemicals while little adsorption by zeolite was observed.
The isotherm data of ionizable compounds tted well to the Langmuir model but those of non-ionizable
chemicals followed a linear equation. Uptake of ionizable compounds depended greatly on pH, increasing
at alkaline pH conditions. In contrary, adsorption of non-ionizable chemicals was essentially the same at
all pH levels studied. The adsorption of both kinds of organic compounds correlated well to kow value,
suggesting that more hydrophobic organic contaminants are more easily retained by modied zeolite.
Based on the different adsorption behavior, the uptake of non-ionizable pollutants was thought to be a
single partitioning process into the surfactant bilayer. For ionizable compounds, however, interaction of
the phenol group(s) with the positively charged head of surfactant additionally functions.
2012 Elsevier B.V. All rights reserved.

1. Introduction
Coal y ash (FA) is a solid waste generated in large amounts
worldwide; therefore, development of new techniques for its productive reuse is important. As a measure to recycle FA, zeolites
synthesized from FA (ZFAs) have been extensively investigated in
recent years. A number of zeolites have been produced from FA,
including Na-P1, philipsite, chabazite, F linde, herschelite, faujasite, analcime, zeolite A, zeolite X, zeolite Y, and hydroxysodalite
[1]. It is shown that ZFA is applicable for the removal of a number of pollutants from water, including ammonium [24], heavy

Corresponding author. Tel.: +86 21 54748529; fax: +86 21 54740825.

E-mail addresses: dywu@sjtu.edu.cn, wudeyi333@yahoo.com.cn (D.Y. Wu).
0304-3894/$ see front matter 2012 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.jhazmat.2012.06.035

metals [516], as well as phosphate [17,18]. Very encouraging

results have also been obtained for ZFA to remove some waste
gases from ue [1921]. Regarding the decontamination of organic
pollutants from water, satisfactory performance was only reported
for methylene blue, a cationic dye [22]. Because the surface of
zeolites is negatively charged and hydrophilic in nature, little afnity toward other organic pollutants such as anionic, ionizable and
non-ionizable organic chemicals is thus expected. Nevertheless,
researchers found that permanent negative charges in crystal structures enable natural zeolites to be modied by cationic surfactants
so that they better retain organic pollutants [2325]. Stimulated
by this advance, we recently presented promising results for the
removal of humic acid (in the form of sodium salt) from water
by surfactant modied zeolite which was synthesized from FA
(SMZFA) [26].

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J. Xie et al. / Journal of Hazardous Materials 231232 (2012) 5763

Table 1
Chemical composition and some properties of FA and ZFA.
Parameter

FA

ZFA

SiO2 (%)
Al2 O3 (%)
Fe2 O3 (%)
CaO (%)
MgO (%)
Na2 O (%)
K2 O (%)
Moisture (%)
Others (%)a
BET surface area (m2 g1 )
CECb (mmol g1 )
ECECc (mmol g1 )
HDTMA loaded (mmol g1 )

51.4
22.1
9.7
6.9
1.6
1.2
1.3
0.1
5.7
1.3
<0.03
<0.03

38.1
20.6
8.5
5.7
1.3
6.8
0.4
12.3
6.3
59.6
1.872
0.178
0.349

a
b
c

TiO2 , carbon, SO3 , etc.

Cation exchange capacity.
External cation exchange capacity.

Most organic pollutants are either ionizable or non-ionizable

compounds. Phenolic compounds are typical ionizable chemicals
which are weakly acidic and thus could form organic anions at
sufciently high pH levels. Phenolic compounds are important in
industry and draw much attention in the practice of water pollution
control. While non-ionizable organic pollutants are permanently
electrically neutral because they do not possess an ionizable group.
The current study focuses on the removal performance and
mechanism of ionizable phenolic compounds and non-ionizable
organic compounds by SMZFA.
2. Materials and methods
2.1. Materials
ZFA was hydrothermally synthesized from FA that was obtained
from the Shidongerchang electric power station in Shanghai, China.
The sources of Si and Al in ZFA arose from the corresponding components in FA (Table 1). For zeolite synthesis, approximately 25 g of
FA was placed in a ask and was mixed with 150 mL of 2.0 mol L1
NaOH solution. The slurry was boiled with reux for 24 h with
stirring. After centrifugation, the solid product (ZFA) was washed
with doubly distilled water three times and twice with ethanol followed by drying in an oven at 60 C. For surfactant modication,
500 mL of the solution of the surfactant, hexadecyltrimethylammonium (HDTMA) bromide, with a concentration of 55 mmol L1 was
vigorously mixed with 10 g of ZFA at 50 C for 4 h. These reaction
conditions were adopted to assure high loading of surfactant. After
being cooled to room temperature, the product was centrifuged,
washed with doubly distilled water, dried in an oven at 60 C and
ground to pass through an 80-mesh sieve.
2.2. Characterization of materials
For the chemical analysis, except for silicon, the samples were
digested with hydrogen uoride in conjunction with perchloric acid
and dissolved later by hydrochloric acid. For silicon, the samples
were melted with sodium hydroxide. The elemental concentrations were then measured in the digestions by Inductively Coupled
Plasma Atomic Emission Spectrometry (IRIS advantage 1000). The
crystalline phase(s) in the materials were identied by powder
X-ray diffraction analysis on a D8 ADVANCE X-ray diffractometer
using Ni ltered Cu-K radiation (40 kV, 40 mA). Particle morphology was observed by SEM using a JEOL JSM-7401F microscope.
The FTIR spectra were recorded with a FT-IR spectrophotometer
(SHIMAZU IRPrestige-21) using the KBr method. The specic surface area was determined on an ASAP 2010 from Micromeritics by

tting the amount of N2 adsorbed at 196 C for the BET equation

after preliminary heating at 200 C. Organic carbon content was
measured by the difference in weight loss between 105 and 750 C.
The total cation exchange capacity (TCEC) was determined from the
amount of retained ammonium by the ammonium acetate method
[27]. The external cation exchange capacity was determined by
adsorption of methylene blue from aqueous solution [28,29].
Zeta potential measurements as a function of medium pH were
determined using a Malvern Instruments Zetasizer 2000 equipped
with a microprocessor unit. Suspensions of 0.05 g/100 mL were
prepared and the medium pH was adjusted by adding 0.1 mol L1
or 0.01 mol L1 HCl (or NaOH). The unit automatically calculated
the electrophoretic mobility of the particles and converted it to
the Zeta potential using the Smoluchowski equation.
2.3. Adsorption experiments
Three phenolic compounds with different pKa and thus different
ionizability (phenol, p-chlorophenol and bisphenol A), and three
non-ionizable compounds with different hydrophobicity (aniline,
nitrobenzene, and naphthalene) were selected to assess the decontamination performance of ionizable and non-ionizable organic
chemicals by SMZFA. Adsorption isotherms were prepared for FA,
ZFA, and SMZFA, respectively. The materials were mixed with aqueous solutions containing the organic pollutants ranging in initial
concentrations and then shaken continuously on an orbital shaker
in a thermostatic chamber (model TS-2102C) at 25 0.1 C for 24 h.
Our preliminary experiments conrmed that the reaction time of
24 h is sufcient for the solutes to reach equilibrium concentrations.
The suspensions were then separated by centrifugation (for pollutants other than bisphenol A) or ltration (for bisphenol A) to yield a
clear supernatant or ltrate for analysis of the equilibrium concentrations of the solutes. Blank test revealed little (<1.5%) adsorption
of bisphenol A by the lter. The concentrations were measured
with UV/Visible Unico spectrophotometer (model UV-2102PCS) at
the wavelength of 270 nm for phenol, 280 nm for p-chlorophenol,
276 nm for bisphenol A, 230 nm for aniline, 268 nm for nitrobenzene, and 285 nm for naphthalene, respectively. The effect of pH
on the removal of phenol, p-chlorophenol, bisphenol A and naphthalene was determined at initial concentrations of 50, 50, 100
and 20 mg L1 , respectively, over a pH range of 311. The pH was
adjusted by adding 0.1 mol L1 or 0.01 mol L1 HCl (or NaOH) to
the solutions. The amounts of solute adsorbed per unit mass of
adsorbent were calculated from the differences between the initial and the nal solute concentrations in solution before and after
adsorption:
q=

(co ce )V
m

where V is the sample volume in L, co is the initial solute concentration in mg L1 , ce is the equilibrium concentration in mg L1 , and
m is the dry weight of zeolite in g. Blank determinations including determinations for adsorbent in the absence of adsorbates and
adsorbates in the absence of adsorbent were always carried out. All
experiments were conducted in duplicate and the mean data are
reported.
3. Results and discussion
3.1. Characterization of the materials
Fig. 1a and b shows the scanning electron microscopy images of
FA and ZFA. The original FA particles typically had spherical shapes
at different sizes, with a smooth surface made of an aluminosilicate
glass phase. Upon formation of zeolite, the surface became rough,
indicating the deposition of clusters of zeolite crystals. Formation

J. Xie et al. / Journal of Hazardous Materials 231232 (2012) 5763

59

Fig. 1. Characterization of materials. (a) SEM image of smooth FA particle. (b) SEM image of ZFA particle. (c) FTIR spectra of FA (upper), ZFA (middle) and SMZFA (lower). (d)
XRD patterns of FA (lower) and ZFA (upper), in which the abbreviation was as follows: P, zeolite Na-P1; M, mullite; Q, quartz.

of zeolite was conrmed by the shift of the band from 1074 cm1
for FA to 995 cm1 for ZFA on Fourier transformed infrared (FTIR)
spectra (Fig. 1c), because tetrahedral Al is characteristic of the zeolite structure and an increase in tetrahedral Al (formation of zeolite)
would induce a shift of the band within the range of 1180950 cm1
(which is assigned to the asymmetric internal T O stretching vibration mode of the TO4 tetrahedra, where T = Si or Al) to a lower
wavenumber [30,31]. The four bands at 438, 596, 675, 739 cm1
are analogous to the Na-P1 zeolite obtained from thermally treated
sediment [31]. Investigation by powder X-ray diffraction (Fig. 1d)
identied the formed zeolite as type Na-P1 (Na6 Al6 Si10 O32 12H2 O,
JCPDS code 39-0219). This zeolite is classied into the gismondine
group with a pore size of 3.1 A 4.5 A [1 0 0] and 2.8 A 4.8 A [1 0 1]
[32]. The presence of mullite and quartz in both FA and ZFA was also
conrmed. The very wide reection at low 2 values (318 ) on
XRD pattern of FA gives the evidence of the presence of amorphous
material. Due to the production of zeolite, ZFA exhibited a greatly
enhanced total cation exchange capacity (TCEC, 1.872 mmol g1 )
and BrunauerEmmettTeller (BET) area (59.6 m2 g1 ) when compared to FA (<0.03 mmol g1 and 1.3 m2 g1 , respectively) (Table 1).
It is worthy of note that ZFAs are usually not pure and contain a
number of components other than zeolite. The comparison of the
CEC value of a ZFA with that of a pure zeolite may provide a semiquantitative estimate of the zeolite content in the ZFA given that
the ZFA contained only one kind of zeolite. The zeolite content in

ZFA of current study was estimated to be 44%, based on the CEC

value of the pure NaP1 zeolite (4.30 mmol g1 ).
The external cation exchange capacity (ECEC) of ZFA, as measured by the adsorption of methylene blue from aqueous solution,
was 0.178 mmol g1 , which accounts for 9.5% of TCEC. The external
surface was used to load HDTMA because the pore size of zeolite is
too small for the HDTMA cation to enter. The amount of HDTMA
loaded was determined to be 0.349 mmol g1 based on the difference in the carbon content between SMZFA and ZFA. This was
nearly twice as the amount of ECEC, indicating that HDTMA formed
a bilayer micelle on the external surface of ZFA. The FTIR absorption bands at 2850 and 2920 cm1 (Fig. 1c), which are attributed
to the symmetric and asymmetric stretching vibrations of C C in
the alkyl chain of HDTMA, indicate that HDTMA formed a bilayer
micelle, rather than monolayer coverage [33,34].
3.2. Adsorption of ionizable phenolic compounds and
non-ionizable organic compounds
Adsorption isotherms of the phenolic compounds from water
on SMZFA are shown in Fig. 2. We conducted the adsorption experiments for FA and ZFA without surfactant modication at the same
time, but as expected, little adsorption by these two materials was
observed. This indicates that adsorption of phenolic compounds
was due to the loaded surfactant bilayer.

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J. Xie et al. / Journal of Hazardous Materials 231232 (2012) 5763

Fig. 2. Adsorption isotherms of ionizable phenolic compounds (upper) and nonionizable organic pollutants (lower). Temperature: 25 0.1 C; liquid/solid ratio:
100 mL/0.05 g for bisphenol A and naphthalene and 40 mg/0.2 g for other solutes;
pH: unadjusted, 10.3; initial concentration: 5100 mg L1 for bisphenol A,
520 mg L1 for naphthalene and 101000 mg L1 for other solutes.

Analysis of the results revealed that the Langmuir model showed

good ts to the experimental data. The Langmuir model can be
expressed as:
1
C
C
+
=
q
Qm
bQm
where q is the amount of solute adsorbed per unit mass of adsorbent
(mg g1 ), C is the concentration of solute in solution at equilibrium
(mg L1 ), Qm is the Langmuir adsorption maximum (mg g1 ), and
b is a constant related to the binding strength of solute. The tting
results are shown in Table 2 and the adsorption maxima from the
Langmuir isotherms are calculated and listed in Table 3. The adsorption ability of the phenolic compounds was in the order bisphenol
A > p-chlorophenol > phenol. The maximum adsorption capacity of
FA and ZFA was also listed but this was obtained from the adsorption capacity at the highest initial concentration investigated, not
from the Langmuir model because the adsorption was too low to
t the model well.
Adsorption isotherms of the non-ionizable compounds from
water on SMZFA are also shown in Fig. 2. In contrary to ionizable
Table 2
Fitting results of the adsorption isotherms of organic pollutants by SMZFA to the
Langmuir model or linear model.
Pollutant

Regression equation

r2

Phenol
p-Chlorophenol
Bisphenol A
Aniline
Nitrobenzene
Naphthalene

c/q = 0.0265c + 5.1055

c/q = 0.0191c + 1.7165
c/q = 0.0110c + 0.1006
q = 0.0033c 0.4763
q = 0.0823c + 0.0661
q = 4.2493c + 6.5737

0.9944
0.9885
0.9996
0.9847
0.9961
0.9988

Fig. 3. Inuence of pH on the adsorption of ionizable phenolic compounds (upper)

and naphthalene, a representative of non-ionizable organic pollutants (lower).
Temperature: 25 0.1 C; liquid/solid ratio: 100 mL/0.05 g for bisphenol A and naphthalene and 40 mg/0.2 g for other solutes.

phenolic compounds, the adsorption isotherms of non-ionizable

compounds followed a linear form, which is typical when the
adsorption process is dominated by hydrophobic partitioning. The
linear model can be expressed as:
q = kd C
where q is the amount of solute adsorbed per unit mass of adsorbent
(mg g1 ), C is the concentration of solute in solution at equilibrium
(mg L1 ), and kd is the adsorption distribution coefcient showing
the adsorptive capability of adsorbents. The tting results are given
in Table 2, and the kd values are listed in Table 3. The adsorption
performance of SMZFA for non-ionizable compounds was in the
order naphthalene > nitrobenzene > aniline. Similarly to ionizable
phenolic compounds, adsorption of non-ionizable compounds was
owing to the surfactant bilayer of SMZFA since both FA and ZFA
exhibited very trivial adsorption and most are two low to build an
isotherm model.
3.3. pH dependency of adsorption
Ionizable phenolic compounds differ from other organic chemicals in that they exist as different species, ionic or electrically
neutral ones, depending on solution pH. The pH of the equilibrium suspensions which contained solid material was around 10.3,
when no articial adjustment of pH was done. The phenolic compounds are mostly ionized to form mono- or di-valent anions at this
pH value. Specically, the percentage of anion species calculated
from the pKa of the compounds is 72.0% for phenol, 89.5% for pchlorophenol, and 89.1% for bisphenol A (in it, monovalent species
51.5%, divalent species 38.0%), respectively. On the other hand, the
non-ionizable compounds occur completely as electrically neutral
species regardless of pH value.
Dependency of adsorption on pH is illustrated in Fig. 3. It can
be seen that the adsorption of ionizable phenolic compounds was

J. Xie et al. / Journal of Hazardous Materials 231232 (2012) 5763

61

Table 3
Adsorption capacity of ionizable phenolic compounds and non-ionizable organic compounds by the investigated materials.a
Material

Phenol

p-Chlorophenol

Bisphenol A

Aniline

Nitrobenzene

Naphthalene

FA
ZFA
SMZFA

1.2
1.3
37.7

1.0
1.5
52.4

1.3
2.7
90.9

N.D.
N.D.
3.3

N.D.
0.4
82.3

N.D.
1.3
4249.3

a
For ionizable phenolic compounds, adsorption capacity was expressed by the maximum sorption capacity, which was calculated from the Langmuir model, while for nonionizable organic compounds, it was expressed by the adsorption distribution coefcient kd , which was determined from the linear sorption isotherm. Units: 103 L mg1
for non-ionizable organic compounds and mg g1 for ionizable phenolic compounds. N.D., not detectable.

dependent on pH; the adsorption remained roughly unchanged at

pH below about 7.58.0, while increase in pH above about this level
resulted in a gradually enhanced adsorption. This behavior suggests
that anionic species has higher afnity toward SMZFA than the neutral one. This behavior suggests the importance of the interaction of
negative charge of organic anions with the positively charged heads
of HDTMA. Measurement of Zeta potential showed that SMZFA was
positively charged due to the formation of surfactant bilayer and
modication of ZFA with surfactant caused a signicant increase in
Zeta potential (Fig. 4).
As anticipated, the adsorption of naphthalene, a non-ionizable
organic chemical, did not show distinct pH dependency (Fig. 3).

9.89, p-chlorophenol 9.37, bisphenol A 9.63 and 10.43. From the

standpoint of ionizability, p-chlorophenol is more ionizable than
phenol and thus should be more benign for being adsorbed. Hence,
pKa value could interpret, in part, the higher adsorptive capability of p-chlorophenol than phenol. On the other hand, the greater
adsorption of bisphenol A might be due to the fact that it has two

3.4. Adsorption mechanism

Good t of isotherm data of ionizable phenolic compounds to the
Langmuir model suggests that they are likely adsorbed on specic
sites of the surface of SMZFA. Possible mechanisms are proposed as
follows: (1) the Coulombic interaction of anionic species of phenolic compounds with the positively charged head of HDTMA
on both the inner layer and the outer layer (the interaction with
HDTMA on inner layer was given in Fig. 5a). In this case, the
hydrophobic benzene ring(s) was probably pointed to the inside
of HDTMA bilayers, because this orientation could be stabilized by
allowing the hydrophobic interaction between benzene ring(s) and
the C16 tail of HDTMA to take place; (2) the coordination of the
electron-donating oxygen atoms of phenol compounds with positively charged heads of HDTMA, but this interaction would be much
weaker than 1) (Fig. 5b); and (3) the adsorption of uncharged phenolic compounds by hydrophobic partitioning into HDTMA bilayers
(Fig. 5c). In each case, however, the hydrophobicity of the organic
chemical would be important for adsorption process. This was supported by the positive relationship between kow and adsorption
maxima for the three phenolic compounds (Fig. 6).
Based on the substantial dependence of the adsorption on pH, it
is deemed that the pKa value is another important parameter inuencing the removal of phenolic compounds, besides kow . The pKa
value of the ionizable phenolic compounds was as follows: phenol

Fig. 4. Zeta potential of ZFA before and after HDTMA modication as a function of
pH.

Fig. 5. Interaction mechanisms of phenol, as an example of organic pollutants, with

SMZFA. In this gure, the meaning of the symbols are as follows: () the head of
) the C-16 chain of HDTMA; (
) zeolite in which
HDTMA; (
represents the negative charge. In (a) and (b) the interaction of the charged and
uncharged phenol group with the head of HDTMA of the outer layer, as well as
the interaction between the hydrophobic benzene ring of organic pollutants and
the hydrophobic C-16 chain of HDTMA may function simultaneously to contribute
to sorption.

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J. Xie et al. / Journal of Hazardous Materials 231232 (2012) 5763

Acknowledgement
This research was supported by the National Key Project for
Water Pollution Control (2012ZX07105002-03).

References

Fig. 6. The relationship between kow and adsorptive capacity for ionizable phenolic
compounds (upper) and non-ionizable organic compounds (lower).

phenol groups to interact with the head of HDTMA, in addition to

its high hydrophobicity.
However, in our current study, only the comparison of phenol
and p-chlorophenol was made to elucidate the importance of pKa
in the adsorption of ionizable phenolic compounds. Further investigation using more compounds with a series of pKa values but
similar kow values is thus needed in future to sufciently support
the conclusion.
For non-ionizable organic contaminants, the interaction mechanism was proposed as a single hydrophobic partitioning process
into the surfactant bilayer. This was supported by the linear
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4. Conclusions
After modication with the surfactant (HDTMA, hexadecyltrimethylammonium), zeolitic material that was hydrothermally synthesized from FA exhibited greatly enhanced adsorptive
capability for both ionizable phenolic compounds and nonionizable organic compounds. The adsorption of the two kinds of
organic chemicals showed different isotherm type and the dependency on pH. The adsorption of non-ionizable compounds was a
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