Research Article

Received: 28 August 2009 Revised: 6 November 2009 Accepted: 7 January 2010 Published online in Wiley Interscience: 17 March 2010

(www.interscience.wiley.com) DOI 10.1002/sia.3230

Preparation of HDTMA-bentonite:
Characterization studies and its adsorption
behavior toward dibenzofuran†
Bilge Erdem, A. Safa Özcan∗ and Adnan Özcan
Bentonite is one of the most commonly used raw materials in the water treatment processes because of its low cost, easily
availability and high mechanical and chemical stability. In this study, natural bentonite was modified with a large organic
surfactant, which is hexadecyltrimethyl ammonium (HDTMA) bromide. The modified bentonite was called organobentonite.
The surface characterization of natural bentonite and HDTMA-bentonite was examined by Fourier transform infrared (FTIR)
spectroscopy, X-ray diffractometry (XRD), Brunauer-Emmett-Teller (BET) and thermogravimetric (TG) analysis. FTIR spectroscopy
showed the existence of HDTMA functional groups on bentonite surface. XRD results revealed randomly lateral-monolayer
arrangements of the intercalated alkylammonium cation. The BET surface area significantly decreased after the modification
due to the coverage of the pores of natural bentonite. Differences in the differential thermogravimetric (DTG) peaks for natural-
and HDTMA-bentonite were observed and interpreted. HDTMA-bentonite was then tested as an adsorbent for the removal of
organic compounds such as dibenzofuran (DBF) from aqueous solutions. The amount of adsorption for HDTMA-bentonite was
found to be around 20 times higher than that of natural bentonite in 10 mg dm−3 DBF solution at 20 ◦ C. The adsorption kinetics
of DBF onto HDTMA-bentonite was also studied at 20, 30 and 40 ◦ C and thermodynamic parameters were calculated. The overall
adsorption process was exothermic and physical in nature. The results indicate that HDTMA-bentonite is an effective and a
low-cost adsorbent for the removal of heterocyclic aromatic compounds such as DBF. Copyright
c 2010 John Wiley & Sons, Ltd.

Keywords: surface characterization; organoclay; adsorption; dibenzofuran; kinetics; thermodynamics

Introduction
One of the major types of environmental pollution is contami-
nation of ground and surface waters. In wastewater treatment
processes such as adsorption, catalytic and rheologic applications,
clays are the widely used raw materials because they are low-
cost, effective, abundant and easily available materials, and have
mostly high specific surface area and mechanical and chemical
stability.[1,2]
Bentonite is a clay material (2 : 1 type) consisting essentially
of the montmorillonite group. The inner layer is composed of
one octahedral alumina sheet placed between two tetrahedral
silica sheets. Bentonite surface is negatively charged due to the
isomorphous substitutions within the layers of Al3+ for Si4+ in
the tetrahedral sheet and Mg2+ for Al3+ in the octahedral sheet.
The charge imbalance is offset by exchangeable cations (Na+ and
Ca2+ , etc.) on the layer surfaces. In the presence of water, Na+
and Ca2+ exist as hydrates and the clay surface has a hydrophilic
property. Therefore, natural bentonite is an ineffective adsorbent
for the nonpolar, nonionic organic compounds in water.[3] The
surface properties of natural bentonite can be greatly modified
with large organic surfactants such as long chain quaternary
alkylammonium salts by simple ion-exchange reactions, by van
der Waals interaction between organic surfactant cations and the
adsorbate.[4,5] As a result, the organobentonite obtained becomes
a more effective adsorbent for the removal of poorly water-soluble
organic pollutants from wastewater.
Dibenzofuran (DBF) is a three-ring heterocyclic aromatic
compound containing an oxygen atom in the skeleton. It is largely
tar, and natural processes such as forest fires.[6] It has a wide
variety of uses as an insecticide, in the production of polyvinyl
chloride (PVC), in industrial bleaching and incineration. Although it
is known to be toxic, there is no information on the acute, chronic,
reproductive, developmental and carcinogenic effects of DBF in
humans or animals. Exposure to DBF may occur from inhalation
of contaminated air or ingesting contaminated drinking water or
food.[7,8] Due to its toxic effects, the removal of the heterocyclic
compound, DBF, from ground and drinking waters becomes very
important.
Adsorption will be a feasible and an effective method for this
purpose. The present work investigates the adsorption capacities
of natural bentonite and hexadecyltrimethyl ammonium bromide
modifying bentonite (HDTMA-bentonite) for DBF with respect to
pH. Various kinetic models including the Lagergren-first-order,
pseudo-second-order and intraparticle diffusion were applied to
the experimental data to evaluate the adsorption mechanism
of DBF onto HDTMA-bentonite. The effects of contact time
and temperature were studied. Kinetic and thermodynamic
parameters were also calculated.
∗
Correspondence to: A. Safa Özcan, Department of Chemistry, Faculty of Science,
Anadolu University, Yunusemre Campus, 26470 Eskişehir, Turkey.
E-mail: asozcan@anadolu.edu.tr
† Paper published as part of the ECASIA 2009 special issue.
1351

Department of Chemistry, Faculty of Science, Anadolu University, Yunusemre

derived from anthropogenic products such as petroleum and coal Campus, 26470 Eskişehir, Turkey

Surf. Interface Anal. 2010, 42, 1351–1356 Copyright

c 2010 John Wiley & Sons, Ltd.
 B. Erdem, A. S. Özcan, A. Özcan

Experimental were carried out at this pH range by increasing periods of time

(1–180 min) and temperatures of 20, 30 and 40 ◦ C until the
Materials
equilibrium had been achieved. After the adsorption procedure,
Natural bentonite used in this study was from Çanakkale, Turkey. the solutions were filtered and DBF concentration in the
It was crushed, ground and sieved to the particle size of less than supernatant was measured by using a spectrophotometer (UV-
63 µm by using an ASTM-standard sieve and dried in an oven at 2101PC) at the respective λmax value, which is 279 nm for DBF.
110 ◦ C for 24 h before use. The amount of DBF adsorbed onto per gram of bentonite (q,
DBF was purchased from Fluka and its 10 mg dm−3 solutions mg g−1 ) was calculated by the difference between the initial and
were prepared by dissolving definite amounts of DBF crystals in remaining concentrations of DBF solution. All experiments were
5% dioxan solutions. carried out in triplicates and the average values were used for
further calculations.
Preparation of HDTMA-bentonite
Respective quantities of natural bentonite and the surfactant of Results and Discussion
HDTMA bromide were suspended in 0.8 dm3 of deionized water.
The amount of HDTMA bromide was equal to 1.5 times the Characterization
cation exchange capacity (CEC) of natural bentonite, which was Chemical composition of natural bentonite
determined as 980 mmol kg−1 by the methylene blue method.[9]
The suspension obtained was stirred for 24 h and it was filtered The XRD results combined with EDX analysis show that silica
through a filter paper. The prepared HDTMA-bentonite was (70.75%) and alumina (16.18%) are the major constituents of nat-
washed with deionized water until a negative bromide test had ural bentonite along with minor amounts of sodium, potassium,
been obtained with 0.1 M AgNO3 . It was dried in an oven and iron, magnesium, calcium and titanium oxides in the form of
sieved through a 63-µm size sieve. HDTMA-bentonite was dried in impurities in the bentonite structure.
an oven at 65 ◦ C for 24 h before to use.
XRD analysis
Characterization The XRD patterns of natural bentonite and HDTMA-bentonite
The chemical analysis of natural bentonite was conducted using were recorded (Fig. 1) and their basal spaces were observed
an energy dispersive X-ray spectrometer (EDX-LINK ISIS 300, at 14.38 and 18.70 Å, respectively. The thickness of bentonite
Cambridge, UK) attached to a scanning electron microscope (SEM- layer was 14.38 Å. The expansion in the basal spacing of natural
Cam Scan S4, UK). The crystalline phases present in bentonite were bentonite after the modification was calculated as 4.32 Å. This
determined by X-ray (XRD-Rigaku Rint 2000, Rigaku Co., Tokyo, result revealed randomly lateral-monolayer arrangements of the
Japan) using Cu Kα radiation. XRD patterns of natural bentonite intercalated alkylammonium cation into bentonite. According to
and HDTMA-bentonite were also recorded.
The Brunauer-Emmett-Teller (BET) surface areas of natural
bentonite and HDTMA-bentonite were determined from N2
adsorption isotherm with a surface area analyzer (Quantachrome
Instruments, Nova 2200e, Florida, USA) after degassing under
vacuum for 2 h at 75 ◦ C. The elemental analysis (Vario EL III
Elemental Analyzer, Hanau, Germany) was carried out to determine
C/N ratio in HDTMA-bentonite.
Fourier transform infrared (FTIR) and thermogravimetric (TG)
analysis of natural bentonite and HDTMA-bentonite were per-
formed with a Perkin-Elmer spectrum 100 model infrared spec-
trophotometer (Waltham, USA) by preparing KBr discs of the
samples and a Setaram Labsys TGDTA model thermal analyzer
(Caluire, France) in the temperature range of 25–1000 ◦ C at a
heating rate of 10 ◦ C min−1 .

Adsorption studies
Adsorption experiments were carried out by using a batch
technique. Two hundreds and 50 ml of 10 mg dm−3 DBF solutions
were treated with 20 mg bentonite and 5 mg HDTMA-bentonite,
respectively. They were sealed with parafilm to avoid evaporation
and stirred for 60 min using a magnetic stirrer at a constant
temperature of 20 ◦ C to determine the adsorption capacity of
natural- and HDTMA-bentonite with respect to pH. The pH values
of the solutions were carefully adjusted between 1.5 and 10.0 by
adding small amounts of HCl or NaOH solutions and measured by
using Fischer Accumet AB15 Model pH meter.
Since the optimum pH range of DBF adsorption onto HDTMA-
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bentonite was determined as 3.5–4.0, the kinetic experiments Figure 1. XRD patterns of (a) natural bentonite and (b) HDTMA-bentonite.

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c 2010 John Wiley & Sons, Ltd. Surf. Interface Anal. 2010, 42, 1351–1356
Preparation of HDTMA-bentonite
Zhu et al.[10] the theoretical length of the HDTMA cation is 25 Å,
and the height of alkyl chain is 4.0 Å and the nailhead is 5.1 Å since
HDTMA cation lies flat between the bentonite layers.
BET analysis
The BET surface areas of natural bentonite and HDTMA-bentonite
were determined as 80.09 and 16.43 m2 g−1 , respectively. By the
intercalation of HDTMA cations, the interparticle pores are covered
and the interlamellar spaces are blocked leading to the inhibition
of the passage of N2 molecules.[11] As a result of the modification
process, the BET surface area decreases.
Elemental analysis
The ratio of C/N for HDTMA-bentonite from elemental analysis
results was found to be 14.97. This value is close to the theoretical
value of C/N ratio which was calculated as 16.29. The percentage of
the modification of natural bentonite with HDTMA is determined
to be 29.14. These results indicate that the modification of natural
bentonite by using HDTMA was accomplished.[2]
FTIR analysis
The FTIR spectra of natural bentonite and HDTMA-bentonite
(Fig. 2) were recorded in the range 400–4000 cm−1 and compared
with each other to observe the modification of natural bentonite
with HDTMA.
As it can be seen from the spectra of natural bentonite and
HDTMA-bentonite (a and b in Fig. 2), the absorption peaks at 3625
and 3431 cm−1 are due to H–O–H stretching vibration bands of
water molecules weakly hydrogen bonded to the Si–O surface and
the –OH stretching vibration of adsorbed water, respectively. The
Figure 2. FTIR spectra of (a) natural bentonite and (b) HDTMA-bentonite.
Surf. Interface Anal. 2010, 42, 1351–1356 Copyright

c 2010 John Wiley & Sons, Ltd.
peak at around 1638 cm−1 corresponds to the OH− deformation
of water in both natural bentonite and HDTMA-bentonite.[12,13]
The intensity of this band for HDTMA-bentonite was lower than
that of natural bentonite.
The peaks at 2918 and 2849 cm−1 can be assigned to the
symmetric and asymmetric stretching vibrations of methylene
groups and their bending vibrations at 1473 and 1408 cm−1 were
only observed on HDTMA-bentonite (b in Fig. 2). The observed
peak at around 719 cm−1 corresponds to the rocking band in the
FTIR spectrum of HDTMA-bentonite (b in Fig. 2). These bands are
also an evidence of the modification.
The bands at around 1091 and 1040 cm−1 appearing in a and
b of Fig. 2 represent the Si–O coordination vibrations and the
stretching of Si–O in the Si–O–Si groups of the tetrahedral sheet,
respectively. Also, Si–O–Al (octahedral) and Si–O–Si bending
vibrations were observed at 521 and 468 cm−1 , respectively, for
natural bentonite and HDTMA-bentonite.[12 – 14]
TG analysis
The TG and differential thermogravimetric (DTG) analysis curves
of natural bentonite (Fig. 3(a)) show two stages of mass losses.
The first stage is at 100–200 ◦ C (6.23% mass loss) related to
the desorption of adsorbed water and the second stage is at
600–800 ◦ C (5.80% mass loss) related to the dehydroxylation of
–OH groups on the surface of natural bentonite. The intensities
of DTG peaks at these temperature ranges were decreased
after modification with HDTMA-bentonite (Fig. 3(c)) due to the
removing of some water with modification of HDTMA cations
between bentonite layers. The other two DTG peaks appearing
in Fig. 3(c) at 250–300 and 400–450 ◦ C correspond to the
decomposition of HDTMA cations. Since the pure HDTMA bromide
decomposes at about 250 ◦ C (Fig. 3(b)), the first peak corresponds
to the decomposition of some HDTMA cations on the surface of
bentonite and the second one assigned to the decomposition of
some HDTMA cations between the layers of bentonite.[12,15] These
results confirm the modification indicating that the surfactants
both locate on the surface and enter into the interlayer spaces of
bentonite.
DBF adsorption onto natural- and HDTMA-bentonite
The adsorption capacities of natural bentonite and HDTMA-
bentonite for DBF with respect to pH were determined. The
results indicate that the amount of adsorption for HDTMA-
bentonite (212.44 mg g−1 ) is around 20 times higher than that
of natural bentonite (10.98 mg g−1 ) in 10 mg dm−3 DBF solu-
tion at 20 ◦ C (Fig. 4). The optimum pH range was also found
to be 3.5–4.0 for DBF adsorption onto HDTMA-bentonite. In
the other pH ranges, the adsorption capacity does not differ
much. After the modification with HDTMA, the hydrophilic prop-
erty of natural bentonite surface became strongly hydrophobic.
Therefore, the amount of DBF adsorption on HDTMA-bentonite
increases due to the fact that DBF has hydrophobic charac-
ter.
Because of the limited adsorption sites, natural bentonite has a
lower adsorption capacity than that of HDTMA-bentonite.
Effect of contact time and temperature
The effect of contact time on the adsorption of DBF onto HDTMA-
1353
bentonite was examined with 10 mg dm−3 DBF solutions at 20,
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 B. Erdem, A. S. Özcan, A. Özcan

250
HDTMA-bentonite
Bentonite

200

q (mg g-1)
20

10

0
0 2 4 6 8 10 12
pH

Figure 4. DBF adsorption onto natural- and HDTMA-bentonite with

respect to pH.

280
260
240
220

q (mg g-1)
200
180
160
140
20°C
120 30°C
40°C
100
0 20 40 60 80 100 120 140 160 180 200
t (min)

Figure 5. Effect of contact time for the adsorption of DBF onto HDTMA-
bentonite at various temperatures.

Adsorption kinetics of DBF onto HDTMA-bentonite

Lagergren-first-order (Eqn (1)),[17] pseudo-second-order
(Eqn (2)) and intraparticle diffusion (Eqn (3))[19] kinetic models
[18]

were applied to the experimental data to find out the adsorption

mechanism by using the following equations:

Figure 3. TG and DTG curves of (a) natural bentonite, (b) HDTMA bromide
and (c) HDTMA-bentonite.
30 and 40 ◦ C (Fig. 5). As can be seen from Fig. 5, the amount
of adsorption increases with an increase in the contact time.
The equilibrium time was found to be 75 min at all studied
temperatures.
The amount of DBF adsorption onto HDTMA-bentonite at
equilibrium decreased with increasing temperature from 20 to
40 ◦ C, indicating that the adsorption of DBF was controlled
by an exothermic process. This can be due to a weakening
of the attractive forces between DBF molecules and adsor-
bent sites at higher temperatures. Since the adsorption is an
exothermic process, it can be called a physical adsorption
1354
ln(qe − qt ) = ln qe − k1 t (1)
t 1 1
= + t (2)
qt k2 q2e qe
qt = kp t1/2 + C (3)
where qe and qt (mg g−1 ) are the amounts of adsorbate adsorbed
at equilibrium and at any time, t (min), respectively, k1 (min−1 )
is the rate constant of Lagergren-first-order kinetic model, k2
(g mg−1 min−1 ) is the rate constant of the pseudo-second-order
kinetic model and kp (mg g−1 min−1/2 ) is the intraparticle diffusion
rate constant.
The straight-line plots of ln(qe − qt ) versus t for the Lagergren-
first-order model, t/qt against t for the pseudo-second-order
model and qt versus t1/2 for the intraparticle diffusion model for
the adsorption of DBF onto HDTMA-bentonite have been drawn
and kinetic parameters were calculated from the respective figures.
These results are listed in Table 1. The correlation coefficients for
the Lagergren-first-order kinetic model (r12 ) are relatively small

(physisorption).[16] and the calculated qe values for the Lagergren-first-order kinetic

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c 2010 John Wiley & Sons, Ltd. Surf. Interface Anal. 2010, 42, 1351–1356
Preparation of HDTMA-bentonite

Table 1. Kinetic parameters for DBF adsorption onto HDTMA-bentonite at various temperatures

Lagergren-first-order Pseudo-second-order Intraparticle diffusion

t k1 qe k2 qe kp
(◦ C) (min−1 ) (mg g−1 ) r12 (g mg−1 min−1 ) (mg g−1 ) r22 (mg g−1 min−1/2 ) rp2

20 −0.024 61.01 0.968 1.17 × 10−3 259.14 0.999 8.102 0.995

30 −0.024 49.45 0.762 1.24 × 10−3 250.25 0.999 8.763 0.987
40 −0.026 46.01 0.853 1.30 × 10−3 242.17 0.999 8.465 0.980

The value of Ea is in the range of 5–40 kJ mol−1 for physical

Table 2. Thermodynamic parameters calculated for DBF adsorption
onto HDTMA-bentonite at various temperatures adsorption and 40–800 kJ mol−1 for chemical adsorption.[21] In
this study, the value of Ea was determined as 4.05 kJ mol−1 (see
t Ea H◦ G◦ S◦ Table 2) indicating that DBF adsorption onto HDTMA-bentonite is
(◦ C) (kJ mol−1 ) KC (kJ mol−1 ) (kJ mol−1 ) (J K mol−1 )
−1
a physical process.
20 4.05 1.84 −6.91 −1.49 −18.51 The thermodynamic parameters such as changes in Gibbs free
30 1.67 −1.29 energy (G◦ ), enthalpy (H◦ ) and entropy (S◦ ) were determined
40 1.53 −1.11 by using the following equations:

model are not compatible with the experimental q values. Since the
correlation coefficients for the pseudo-second-order kinetic model
(r22 ) are 0.999 for all studied temperatures, the adsorption data
fitted with the pseudo-second-order kinetic model. The calculated
qe values for the pseudo-second-order kinetic model also agree
very well with the experimental q values.
The Lagergren-first-order and pseudo-second-order kinetic
models cannot identify the diffusion mechanism. The most
commonly used method to clarify the diffusion mechanism is
the intraparticle diffusion model. According to this model, the plot
of qt versus t1/2 , should be linear, if the adsorption process involves
intraparticle diffusion and the intraparticle diffusion will be the
sole rate-limiting step if the obtained straight-line passes through
the origin.[20] The plots did not pass through the origin indicating
that the adsorption process involves some degree of boundary
layer control and the intraparticle diffusion was not the rate-
controlling step. The initial curved portion of the plots corresponds
to the boundary layer adsorption and the linear portion refers to
the intraparticle diffusion, with the plateau corresponding to
equilibrium.[2] In this study, it was found that the plots of qt
versus t1/2 exhibited an initial linear portion with the correlation
coefficients (rp2 ) between 0.980 and 0.995 followed by a plateau
which occurred after 75 min. According to these results, it can be
said that intraparticle diffusion played a significant role, but it was
not the main rate-determining step during the adsorption.
CA
KC = (5)
CS
◦
G = −RT ln KC (6)
◦ ◦
S H
ln KC = − (7)
R RT
where KC is the equilibrium constant, CA (mg dm−3 ) is the amount
of DBF (mg) adsorbed on the adsorbent per cubic decimeter of
the solution at equilibrium and CS (mg dm−3 ) is the equilibrium
concentration of DBF in the solution. To calculate CA and CS , the
qe values for the pseudo-second-order kinetic model in Table 1
were used. H◦ and S◦ were calculated from the slope and the
intercept of van’t Hoff plots of ln KC versus 1/T. The results are
listed in Table 2.
The negative values of G◦ confirm the spontaneous nature of
the adsorption and the magnitude of G◦ gives an information
about the type of adsorption. Generally, the value of G◦ is
between −20 and 0 kJ mol−1 for physisorption and −80 and
−400 kJ mol−1 for chemisorption.[14] G◦ value of DBF adsorption
onto HDTMA-bentonite was −1.49 kJ mol−1 indicating that the
adsorption process is a spontaneous physical process at 20 ◦ C.
The H◦ value of −6.91 kJ mol−1 indicates that the adsorption
process is exothermic and physical in nature involving weak forces
of attraction. The negative values of S◦ correspond to a decrease
of freedom of the adsorbed species.

Thermodynamic parameters
The pseudo-second-order rate constant (k2 ) of the adsorption is
expressed as a function of temperature by the Arrhenius equation:
Ea
ln k2 = ln A −
RT
where Ea (kJ mol−1 ) is the Arrhenius activation energy of
adsorption which is the minimum energy that reactants must
have for the adsorption to proceed, A is the Arrhenius factor, R is
the gas constant which is equal to 8.314 J mol−1 K−1 and T (K) is
the solution temperature. The linear plot of ln k2 versus 1/T gives
a slope of −Ea /R. The magnitude of Ea may also give an opinion
Conclusions
In this study, HDTMA-bentonite was prepared by modifying natural
bentonite with HDTMA bromide. The surface characterization of
HDTMA-bentonite was examined by using XRD, BET, FTIR and TG
and elemental analysis.
(4) Chemical composition of natural bentonite obtained from
XRD/EDX shows that it is composed mainly of SiO2 and Al2 O3 .
According to the values of basal spaces obtained from XRD
analysis, HDTMA cations intercalate into natural bentonite with
randomly lateral-monolayer arrangements. The BET surface area
significantly decreased after the modification due to the coverage
of the interparticle pores of natural bentonite. The percentage of
the modification of natural bentonite with HDTMA is determined as
1355

about the mechanism of adsorption (if it is physical or chemical). 29.14 by elemental analysis. Existence of HDTMA functional groups

Surf. Interface Anal. 2010, 42, 1351–1356 Copyright

c 2010 John Wiley & Sons, Ltd. www.interscience.wiley.com/journal/sia

on bentonite surface was also characterized by FTIR spectroscopy
technique. TG analysis show that HDTMA cations both locate on
the surface and enter into the interlayers of bentonite.
The adsorption capacities of natural- and HDTMA-bentonite for
an organic pollutant of DBF were compared with respect to pH.
The amount of adsorption for HDTMA-bentonite was found to be
around 20 times higher than that of natural bentonite, in 10 mg
dm−3 of DBF solution at 20 ◦ C. The adsorption kinetics of DBF
adsorption onto HDTMA-bentonite was also studied at 20, 30 and
40 ◦ C. The amount of adsorption increased with the contact time
and decreased with increasing temperature indicating that the
adsorption of DBF was controlled by a physical and exothermic
process. However, the adsorption process fitted well with the
pseudo-second-order kinetic model, it was also followed by the
intraparticle diffusion up to 75 min. The maximum adsorption
capacity was determined as 259.14 mg g−1 from the pseudo-
second-order kinetic model at 20 ◦ C. The results indicate that
HDTMA-bentonite can be an effective and a low-cost adsorbent
for DBF removal from aqueous solutions.
Acknowledgement
The authors gratefully acknowledge the financial support of
Anadolu University for the Scientific Research Projects (Project
No. 061027).
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