R. C. FERREIRA et al., Effect of Solution pH on the Removal of Paracetamol by Activated…, Chem. Biochem. Eng. Q.

, 29 (1) 47–53 (2015) 47

Effect of Solution pH on the Removal of Paracetamol

by Activated Carbon of Dende Coconut Mesocarp
R. C. Ferreira,a,* O. M. Couto Junior,b K. Q. Carvalho,c P. A. Arroyo,a and M. A. S. D. Barrosa
a
Chemical Engineering Department, State University of Maringá (UEM),
5790 Colombo Av., 87020–900, Maringá, Paraná, Brazil
b
Center of Technology and Exact Science, The University Center
of Maringá (Unicesumar), 1610 Guedner Av. – 87050-390
Maringá, Paraná, Brazil doi: 10.15255/CABEQ.2014.2115
c
Academic Department of Civil Construction, Federal Technological Original scientific paper
University of Paraná (UTFPR), 4900 Deputado Heitor Alencar Furtado St., Received: September 19, 2014
81280–340, Curitiba, Paraná, Brazil Accepted: March 3, 2015

Activated carbon of dende coconut mesocarp was used to investigate the removal
of paracetamol from water by adsorption. The results indicated that the retention of
paracetamol was favored in activated carbon with neutral surface properties. The textural
features and presence of a transport pores network contri­buted to ensuring the accessibil-
ity to the inner porosity, and the microporosity must be large enough to accommodate the
paracetamol molecule. Chemisorption and mainly physisorption are important in the
paracetamol removal. Pseudo-second order equation and Langmuir model were chosen
to best present the experimental data. The a­ dsorption process was non-spontaneous and
endothermic with increase in system dis­order.
Key words
paracetamol, adsorption, activated carbon, dende coconut

Introduction seeking the best adsorbent to solve a local problem

through the available natural disposals.
The production of pharmaceuticals has in- Therefore, in this work, the activated carbon
creased rapidly in the last decades, providing better from dende coconut residue was used to remove
health quality for humans and animals. Upon their paracetamol. Dende is a typical Brazilian palm tree
use, large amounts of pharmaceuticals are discharged that produces oil, which is applied in medicine,
into the water bodies, and are thus detected in waste- food industry, and even as biodiesel. The dende ac-
water and surface water at ng L–1 to µg L–1 levels1,2. tivated carbon was obtained by burning mesocarp
Conventional wastewater treatments for pharmaceu- fibers and dende peels15.
ticals are ineffective in eliminating and/or degrading Adsorption of paracetamol on carbon has been
most of these compounds. Therefore, residual quan- widely studied by Terzyk16, Villaescusa17, Mestre11
tities remain in the treated water, and have been and Ribeiro18. Nevertheless, biosorbents based on
found to accumulate in drinking water3,4. Particular- industrial and agricultural wastes to remove organic
ly, paracetamol is one of the pharmaceuticals of compounds are scarely investigated.
common use worldwide due to its effectiveness in
In order to fulfill this lack of information, this
the relief of pain and fever. Unfortunately, its pres-
ence in recycled water has already been detected5. paper presents results related to the influence of
temperature and pH in the adsorption process. Ki-
In this context, adsorption may improve waste- netics, equilibrium data, as well as thermodynamics
water treatment. As adsorbents, activated carbons are reported.
from biomass residues have been widely studied.
Among these residues stand out cork powder6,
peach stones, and PET bottles7, coconut endocarp Materials and methods
and palm endocarp8, olive stone9, tobacco residue10
sisal waste11, mangosteen peel12, coconut meso- Adsorbents
carp13, oil palm empty fruit bunch, bamboo stem,
coconut shells14. Indeed, researchers have been The activated carbon of dende coconut meso-
carp was kindly supplied by Bahiacarbon Inc. (Ba-
 Corresponding author: e-mail: [email protected]
*
hia, Brazil).
48 R. C. FERREIRA et al., Effect of Solution pH on the Removal of Paracetamol by Activated…, Chem. Biochem. Eng. Q., 29 (1) 47–53 (2015)

The samples were previously washed with hot The mechanism of adsorption and kinetic pa-
deionized water (50  °C), dried in an incubator for rameters sorption data were analyzed using pseu-
24 h at 60  °C, ground and sieved with average do-first-order20 and pseudo-second order models21.
­diameter of 0.180 mm (70–100 mesh ASTM). No The pseudo-first-order rate equation of Lager-
previous chemical or physical treatment was done. gren based on solid capacity is expressed as follows:
Nanotextural and chemical characterization dqt
 k1 ( qe  qt ) (2)
of the carbon samples dt
The activated carbon was characterized by N2 where k1 is the constant rate of pseudo-first-order
adsorption in ASAP 2000 Micromeritics equipment adsorption (min–1), qe (mg g–1) is the amount of
at –196 ºC and 0 ºC with liquid N2. paracetamol at equilibrium, and qt (mg g–1) is the
Prior to the experiments, the samples were out- amount of paracetamol at time t (min).
gassed for 2  h at 300  ºC, under vacuum (10–2  Pa). Integration of Eq. (2) for the initial conditions
The isotherms were used to calculate the specific t = 0 and qt = 0 gives:
surface area (SBET), total pore volume, micropore
volume and pore size distribution. Apparent specific qt qe (1 ek1t ) (3)

surface area was assessed applying the BET equa-
tion (in the range 0.05 < P/P0 < 0.30). The point of The pseudo-second-order kinetic model equa-
zero charge (pHPZC) was estimated using the mass tion is expressed as follows:
titration procedure18.
dqt
Adsorbate  k2 ( qe  qt ) 2 (4)
dt
Paracetamol or acetaminophen (N-(4-hydroxy- where k2 is the constant rate of pseudo-second-order
phenyl)ethanamide), the common name of N-ace- adsorption (g mg–1 min–1), qe (mg g–1) is the amount
til-p-aminophenol, was bought by Sigma-Aldrich of paracetamol at equilibrium, and qt (mg g–1) is the
(purity 98 %). All paracetamol solutions contained amount of paracetamol at time t (min).
10 % v/v of methanol and concentration of 50 mg
dm–3. They were prepared with ultra-pure water ob- Integration of Eq. (4) for the initial conditions
tained from Milli-Q water purification systems. The t = 0 and qt = 0 gives:
pH solutions of paracetamol were adjusted to 2, qe2 k2t
pHPZC and 11 adding 0.1 mol dm–3 of HCl or NaOH. qt  (5)
1 k2 qet
A volume of 20 cm3 of the para­cetamol solutions
was used in all adsorption studies.
Equilibrium modeling
Kinetic of adsorption
Equilibrium adsorption studies were carried out
Kinetic adsorption studies were carried out in varying the adsorbent doses (0.07–60 mg), keeping
finite bath (Dubnoff, Nova Ética) systems at 25 ºC constant the solution volume (20 cm3), and the tem-
and 150 rpm, where the paracetamol solution was perature (25 ºC).
mixed with 10 mg of activated carbon in glass vials. Adsorption isotherms are the equilibrium rela-
Time-recording started when the stirring began, and tionships between the concentrations of the ad-
samples were collected between 5 minutes and 8 sorbed paracetamol and the paracetamol ion in the
hours. After filtration, paracetamol concentration solution at a given temperature. Langmuir and Fre-
was determined for analysis by UV-VIS spectro- undlich isotherm models were used to investigate
photometry technique using Hach DR 5000 equip- the adsorption equilibrium between the paracetamol
ment (lmax = 240 nm). Paracetamol removal was solution and the activated carbon phase.
calculated according to the following equation:
The Langmuir adsorption isotherm equation, ex-
 0   pressed as follows, requires for its applicability a mo-
qt  V (1) no-layered coverage on the surface of adsorbent22:
m
q k 
qe  max L e (6)
where qt is the amount (mg g–1) of paracetamol ad- 1 k L  e
sorbed at time t, 0 is the paracetamol initial con-
centration (mg dm–3),  is the paracetamol concen- where qe, kL, qmax and e are the paracetamol uptake
tration at time t (mg dm–3), V is the volume (dm3) of at equilibrium (mg g–1), the Langmuir constant
the adsorbate solution, and m is the mass (g) of (dm3 mg–1), the monolayer adsorption capacity
dried activated carbon of dende coconut mesocarp. (mg g–1) and the solution concentration at equilibri-
R. C. FERREIRA et al., Effect of Solution pH on the Removal of Paracetamol by Activated…, Chem. Biochem. Eng. Q., 29 (1) 47–53 (2015) 49

um (mg dm–3), respectively. The Freundlich equa-

tion is applicable for multi-component adsorption.
The Freundlich isotherm is expressed by23:

qe k F 1/n
e (7)

where kF is the Freundlich constant (mg1–1/n (dm3)1/n

g–1), and n is the Freundlich exponent. The Freun-
dlich equation was successfully used to fit the ex-
perimental data for many fluid–solid systems, but
one of the main drawback of this equation is that it
does not tend to a limiting value when the equilibri-
um concentration increases.

Thermodynamic parameters
F i g . 1 – N2 adsorption–desorption isotherms at 77 K of the
It is well known that thermodynamic parame- dende (●) adsorption and (○) desorption
ters can evaluate the orientation and feasibility of
the physicochemical adsorptive reaction. The three liquid nitrogen was condensed in slit-shaped meso-
thermodynamic parameters considered were stan- pores24.
dard enthalpy (∆H°), standard free energy (∆G°), The SBET surface area of activated carbon was
and standard entropy (∆S°). The value of ∆H° and 672 m2  g–1. Total pore volume obtained was
∆S° was obtained from the following equation: 0.369 cm3  g–1, 0.287  cm3  g–1 related to micro­pores
and 0.082  cm3  g–1 related to mesopores. Fig. 2 de-
S  H  picts the pore diameter distribution. The average
K
ln  (8)
R RT pore diameter of 34.5 Å indicated that the ­activated
carbon was in the micropores (region < 20 Å) and
where K is called the adsorption affinity and corre- mesopores (region between 20 to 500 Å). Regard-
sponds to the ratio of qe, related to the amount adsorbed ing the surface chemistry, the value of pHPZC re-
per unit mass (mg g−1), and e, the equilibrium concen- vealed that the activated carbon pre­sented predomi-
tration (mg dm−3) of the solute (K = qe/γe), R is the uni- nantly neutral nature with value of 6.5.
versal gas constant (8.314 J mol–1 K–1), T is the absolute
solution temperature (K). The values of ΔH° and ΔS°
were determined from the slope and the intercept of the
linear plot of ln K versus 1/T, and from these values
Gibbs free energy (ΔG°) was calculated as follows:

G   H  T S  (9)

The effect of temperature on adsorption was

studied at 298, 308 and 318 ± 1 K, by considering
samples of activated carbon (0.07–60 mg) added in
paracetamol solution and constantly stirred until
equilibrium time.

Results and discussion

F i g . 2 – Pore diameter distribution curves, based on the BJH
Characterization of the adsorbent method for dende activated carbon

The nitrogen adsorption-desorption isotherm

is presented in Fig. 1. The activated carbon of Paracetamol adsorption
dende coconut mesocarp was a typical micropo- Kinetic studies and the effect of solution pH
rous–mesoporous material (type I in the IUPAC
classification) with a hysteresis loop (H4 types) This study was carried out with the control
in the desorption branch at relative pressures of  pH and temperature, as reported by Fonte-
above 0.5. The adsorption–desorption hysteresis cha-Cámara25. The study of adsorption from aque-
on activated carbon isotherm showed clearly that ous solutions requires at least the control of these
50 R. C. FERREIRA et al., Effect of Solution pH on the Removal of Paracetamol by Activated…, Chem. Biochem. Eng. Q., 29 (1) 47–53 (2015)

portional to the micropore volume6,26,27. Therefore,

the promising results obtained at pH 6.5 and 2 may
be a consequence of the significant contribution of
the predominant microporous adsorbent and its sur-
face charge. Probably, the carbonyl group of parac-
etamol induced some chemisorption, although phy-
sisorption should have higher contribution mainly
in the micropores, in which the molecule can be
better retained. In basic solutions with pH > pKa,
the amount retained represented a drastic decrease
due to the anionic charges involved.
The adjusted parameters of adsorption kinetics
at pH 2.0, 6.5 and 11.0 (Table 1) were calculated
from the non-linear regressions of the integrated
F i g . 3 – Kinetic results of paracetamol adsorption at 25 °C Eqs. (2)–(5).
to pH 2.0, 6.5 and 11.0
The best fitting of adsorption kinetics at pH 6.5
(R2 = 0.988) was obtained for the pseudo-second-or-
parameters, with no addition of salts. The adsorp- der model. The maximum amount of paracetamol
tion that occurs in a solid–liquid is generally experimentally retained in equilibrium was 65.57
more  complex than that verified in a solid–gas, ­as mg g–1 for pH 2.0, 64.85 mg g–1 for pH 6.5, and
water is a reactive solvent, present in various forms 44.12 mg g–1 for pH 11.0 similar to the ones pre­
(H2O, OH– and H+). Concentration of each species
dicted by the pseudo-second order model. Moreover,
depends on the pH5.
it was seen that adsorption decreases in basic solu-
Kinetic results are displayed in Fig. 3. tions. The pseudo-second-order rate constant k2 ob-
Paracetamol removal efficiency was very simi- tained at pH 11.0 (0.0016 g mg–1 h–1) was lower than
lar for pH values of 2.0 and 6.5. Concentration de- at pH 6.5 (0.0018 g mg–1 h–1), indicating that the
creases rapidly at pH 6.5 and 20 up to 120 min. paracetamol adsorption at pH 11.0 required a higher
Then after such time it was assumed that this sys- amount of activated carbon than at pH 6.5 to reach
tem reached equilibrium. the same adsorption efficiency.
Differences between kinetic curves of pH 2 and
6.5 compared to the one obtained for pH 11 are due Adsorption isotherms
to the pH influence in the ionization state of weak
electrolyte of paracetamol (pKa~9) and the charges Fig. 4 illustrates the paracetamol adsorption
that may appear in the carbon surface. At pH 11, isotherms. The isotherm shape may be classified as
paracetamol molecule was repealed by the nega- L type28, characteristic of a steep initial rise and a
tively charged carbon surface26,27. At pHPZC and pH concave curvature at low equilibrium concentra-
2, the neutral paracetamol molecules were adsorbed tions typical by a plateau or saturation limit. This is
by the equally neutral and positively charged adsor- characteristic of systems where the adsorbate pres-
bent surface. ents high affinity towards the adsorbent, and there-
The amount of pharmaceutical compounds ad- fore indicates no strong competition of the solvent
sorbed onto activated carbon is usually directly pro- for the active sites of adsorption.

Ta b l e 1 – Kinetic modeling of paracetamol adsorption

Kinetic model Parameters pH = 2.0 pH = 6.5 pH = 11.0

qe (mg g–1) 59.11±1.892 58.31±1.756 43.07±1.142

Pseudo-first-order k1 (h–1) 0.092±0.016 0.081±0.013 0.055±0.005

R2 0.911 0.928 0.979

qe (mg g–1) 63.11±1.244 62.91±0.929 46.81±0.804

Pseudo-second-order k2 (g mg –1 h–1) 0.0020±3.3·10–4 0.0018±1.9·10–4 0.0016±1.7·10–4

R2 0.976 0.988 0.978

k1 is the pseudo-first-order rate constant; k2 is the pseudo-second-order rate constant; qe is the amount of paracetamol at equilibrium.
R. C. FERREIRA et al., Effect of Solution pH on the Removal of Paracetamol by Activated…, Chem. Biochem. Eng. Q., 29 (1) 47–53 (2015) 51

F i g . 4 – Experimental adsorption isotherms of paracetamol

onto activated carbon at 25 oC and solution pH 2.0, F i g . 5 – Experimental adsorption isotherms of paracetamol
6.5 and 11.0 fitted to Langmuir model onto activated carbon at 298, 308 and 318 K

The experimental adsorption isotherms were is in accordance with the fact that chemisorption
fitted to the classic Langmuir22 and Freundlich mod- played an important role in the global adsorption.
els23 (equations (6) – (7)).
Adsorption thermodynamics
The maximum experimental retention of parac-
etamol (qt) was 64.75 mg g–1 for pH 2.0, 74.31 mg g–1 The isotherms at different temperatures were
for pH 6.5, and 42.75 mg g–1 for pH 11.0. It is pos- used to estimate the adsorption parameters.
sible to verify (Table 2) that Langmuir adjustment Values of ∆Hº, ∆Sº and ∆Gº are shown in Table
obtained the best fitting with higher R2 and lower 3. The ∆Gº values for all temperatures were posi-
parameter deviation. Then, such model was chosen tive, which reflected the non-spontaneous nature of
as one that best represents experimental data. Com- the adsorption processes. The positive ∆Hº value
parison of maximum experimental retention of indicated that the adsorption process was endo­
paracetamol and the qmax from Langmuir verified thermic in nature. Possibly an increase in tem­
that the maximum amount was not experimentally perature is needed for better accommodation of
reached. It can be noted that the highest removal paracetamol molecules previously attracted by the
was obtained for pH 2.0 and 6.5, which is in agree- superficial positive charge in the micropores. The
ment with the kinetic data and can be explained
through pKa and surface pH. Moreover, samples Ta b l e 3 – Thermodynamic parameters for the adsorption of
with pH 2.0 and 6.5 presented the highest adsorp- activated carbon of dende coconut mesocarp
tion affinity (kL values) to paracetamol molecules,
according to data quoted in Table 2. T ∆G° ∆H° ∆S°
R2
(K) (kJ mol–1) (kJ mol–1) (kJ mol–1)
Isotherms at 298 K, 308 K and 318 K were ob-
tained in neutral (pH 6.5). As most wastewaters 298 4.434
have this characteristic. Figure 5 shows such exper- 308 5.366 16.666 71 0.945
imental data where it can be seen that increase tem-
318 5.845
peratures provide higher paracetamol removal. This

Ta b l e 2 – Fitting parameters of the equilibrium adsorption isotherms to the Langmuir and Freundlich models
Isotherms Parameters pH = 2.0 pH = 6.5 pH = 11.0

qmax (mg g–1) 80.620±1.599 90.813±3.073 62.911±5.872

Langmuir equation kL (dm3 mg–1) 0.280±0.026 0.187±0.019 0.117±0.029

R2 0.980 0.984 0.925

kF (mg1–1/n (dm3)1/n g–1) 25.843±1.937 21.398±2.209 12.212±2.388

Freundlich equation 1/n 0.281±0.349 0.404±0.235 0.422±0.393

R2 0.948 0.944 0.879

52 R. C. FERREIRA et al., Effect of Solution pH on the Removal of Paracetamol by Activated…, Chem. Biochem. Eng. Q., 29 (1) 47–53 (2015)

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