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Science of the Total Environment 433 (2012) 296301

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Science of the Total Environment


journal homepage: www.elsevier.com/locate/scitotenv

Removal of ibuprofen and its transformation products: Experimental and


simulation studies
N. Collado a, G. Buttiglieri b, L. Ferrando-Climent b, S. Rodriguez-Mozaz b, D. Barcel b, c,
J. Comas a, I. Rodriguez-Roda a, b,
a
b
c

LEQUiA, Laboratory of Chemical and Environmental Engineering, University of Girona, Campus Montilivi, Girona, 17071, Spain
ICRA, Catalan Institute for Water Research, Carrer Emili Grahit, 101, Parc Cientc i Tecnolgic de la Universitat de Girona, 17003 Girona, Spain
Dept. Environmental Chemistry, Institute of Environmental Assessment and Water Research (IDAEA), CSIC, c/Jordi Girona 18-26, E-08034 Barcelona, Spain

a r t i c l e

i n f o

Article history:
Received 16 March 2012
Received in revised form 8 June 2012
Accepted 16 June 2012
Available online 15 July 2012
Keywords:
Ibuprofen
Kinetics
Biodegradation
Transformation products

a b s t r a c t
Pharmaceutically active compounds (PhACs) deserve attention because of their effect on ecosystems and
human health, as well as their continuous introduction into the aquatic environment. Classication schemes
are suggested to characterise their biological degradation, e.g., based on pseudo-rst-order kinetics, but these
schemes can vary signicantly, presumably due to pharmaceutical loads, sludge characteristics and experimental conditions. Degradation data for PhAC transformation products (TPs) are largely lacking.
The present work focuses not only on the biodegradation of the pharmaceutical compound ibuprofen but also
on its best-known TPs (i.e., carboxyl ibuprofen and both hydroxyl ibuprofen isomers). Ibuprofen is one of the
most commonly consumed PhACs and can be found in different environmental compartments.
The experiment performed consisted of a set of aerated batch tests with different suspended solid and ibuprofen concentrations to determine the inuence of these parameters on the calculated biodegradation constant (Kbiol). Sampling of the liquid phase at different scheduled times was assessed, removal efciencies
were calculated and pseudo-rst-order kinetics were adjusted to obtain experimental Kbiol values for the parent compound and its TPs.
The experimental data were successfully tted to ASM-based models, with Kbiol values for the target compounds ranging from almost 1 to 17 L gSST 1 d1, depending on the concentrations of the biomass and ibuprofen. This work provides innovative knowledge not only regarding the removal of TPs but also the
formation kinetics of these TPs.
2012 Elsevier B.V. All rights reserved.

1. Introduction
Residues of pharmaceutically active compounds (PhACs) have
raised concern because of their continuous introduction into the aquatic
environment (Barcel and Petrovic, 2007; Santos et al., 2009). PhACs
are administered in large quantities to humans and animals and have
been detected in all compartments of the aquatic environment
(Castiglioni et al., 2006; Bartelt-Hunt et al., 2009). The real effect of
PhACs on ecosystems and human health, directly via drinking water
and/or indirectly via the food chain, has not been completely elucidated.
Moreover, there is no legislation regarding the regulation of PhACs.
However, the impact of PhACs, considering both acute and chronic effects on non-target organisms, has been studied, with an emphasis on
Abbreviations: ASM, activated sludge model; IBU, ibuprofen; IBU-OH, hydroxyl
ibuprofen; IBU-1OH, 1-hydroxyl ibuprofen; IBU-2OH, 2-hydroxyl ibuprofen; IBU-CBX,
carboxyl ibuprofen; Kbiol, biodegradation reaction rate constant; KD, adsorption coefcient; PhACs, pharmaceutically active compounds; TP, transformation product; TSS,
total suspended solid; WWTP, wastewater treatment plant.
Corresponding author.
E-mail address: irodriguezroda@icra.cat (I. Rodriguez-Roda).
0048-9697/$ see front matter 2012 Elsevier B.V. All rights reserved.
doi:10.1016/j.scitotenv.2012.06.060

PhACs as a continuous threat to environmental stability (Santos et al.,


2010; Schnell et al., 2009) and the need for a better understanding of
their fate to facilitate their removal from the environment.
PhACs are primarily released through wastewater treatment
plant (WWTP) discharges (Heberer, 2002). WWTPs are not currently designed for complete removal of PhACs (Joss et al., 2008). Extensive WWTP sampling campaigns have been explored in several
countries where various WWTP treatment technologies have been
applied, and extensive information is available on PhAC inuent
and efuent concentrations with reported concentrations typically
on the order of ng L 1 or low g L 1 (Kolpin et al., 2002;
Buttiglieri and Knepper, 2008; Carballa et al., 2008). Several studies
have demonstrated that some PhACs are efciently removed within
WWTP facilities (e.g., ibuprofen, naproxen and ketoprofen), while
others are more persistent (e.g., diclofenac and clobric acid)
(Quintana et al., 2005; Kosjek et al., 2007; Onesios et al., 2009;
Tambosi et al., 2010). Within the WWTP, the PhAC may be removed
from the liquid phase depending on its susceptibility to adsorption
or biodegradation (Ternes and Joss, 2006). Little information has
been reported on the presence of PhAC transformation products

N. Collado et al. / Science of the Total Environment 433 (2012) 296301

(TPs), the formation of these TPs or their removal because most of


the available reports focus on the parent compound.
Modelling and simulation of the transport and removal of macropollutants (such as organic matter, nitrogen, phosphorus and suspended
solids) in WWTPs can be considered a mature scientic discipline. The
standard and most widely used models are deterministic, describing
the removal of organic matter and nutrients from activated sludge (AS)
(Gernaey et al., 2004), or metabolic (van Loosdrecht and Heijnen,
2002). Modelling and simulating micropollutants are currently a growing area of interest and activity within urban water cycle modelling
to support load estimation, predict environmental impact and nd optimal organic removal technologies for micropollutants and PhACs in
particular.
The activated sludge models (ASMs) have been extended to include the occurrence, transport and fate of micropollutants, with
consideration of parent compound formation, sorption and biodegradation processes, both aerobic and anoxic conditions and different
wastewater fractions (aqueous, solid, retransformable and sequestered) to predict the capability of removing several micropollutants
from activated sludge systems (Plsz et al., 2010, 2011). Extensions
of the ASMs to micropollutants in different units of the urban water
systems (sewer systems, WWTP and receiving waters), including
physical (sedimentation, resuspension and volatilisation), physicochemical (sorptiondesorption, hydrolysis and photolysis) and biological (aerobic and anoxic biodegradation) processes have also
been documented (Benedetti et al., 2010).
For PhAC biodegradation processes in activated sludge,
pseudo-rst-order reaction kinetics and the use of biodegradation reaction rate constants (Kbiol) have been proposed (Joss et al., 2006). Data
are available for some pharmaceutical compounds under specic
conditions and at specic concentrations. However, the Kbiol values
reported in the literature differ signicantly among authors. Some authors ascribe this variability of biodegradation rates to differences in
the initial pharmaceutical load (Abegglen et al., 2009), while others
also highlight the importance of sludge composition (i.e., diversity of
biomass, types of primary substrates, and so on) and experimental conditions (Tran et al., 2009). To the authors' knowledge, no modelling
studies have been published yet regarding the biodegradation of parent
compounds and their TPs.
Ibuprofen, a non-steroidal anti-inammatory drug, has been selected for the study because of its worldwide use and presence. The
estimated annual consumption of ibuprofen in developed countries
is several hundred tonnes (Daughton and Ternes, 1999). The presence
of ibuprofen in raw wastewater (ranging broadly from low g L 1 to
373 g L 1, with an average inuent concentration of 37 g L 1), its
removal (95% or higher in secondary treatment; Smook et al., 2008)
and transformation in WWTPs have been studied extensively
(Onesios et al., 2009; Verlicchi et al., 2012). A large proportion of
the active compound is excreted as the parent compound together
with its known human metabolites, hydroxyl ibuprofen (IBU-OH)
and carboxyl ibuprofen (IBU-CBX) (Zwiener et al., 2002). However,
the human metabolites of ibuprofen are identical to its TPs (Stumpf
et al., 1999; Buser et al., 1999) i.e. generated from biotic/abiotic processes in the environment. Ibuprofen in the water environment has
been shown to affect on the reproduction in both vertebrates and invertebrates (Hayashi et al., 2008). Parental exposure to as low as
0.1 g L 1 ibuprofen can delay hatching of eggs of freshwater sh
(Han et al., 2010). Acute and sub-chronic assays carried out at
ng L 1 ibuprofen concentrations demonstrated also genotoxic effects
for sh (Ragugnetti et al., 2011).
The aim of this manuscript is twofold. The rst objective is to present
an experimental study of the biodegradability of ibuprofen to determine the inuence of the initial concentration of the pharmaceutical
and biomass contents. The second objective is to t the experimental
data to ASM-based models with pseudo-rst-order kinetics, relating
parent compound degradation to TP formation.

297

2. Materials and methods


2.1. Batch tests
A set of laboratory batch biodegradation studies with activated
sludge from a municipal WWTP has been performed to investigate
the biodegradation proles of ibuprofen and the formation and removal of its major TPs.
The batch experiments consisted of a set of two-litre glass bottles,
with permanent aeration and automatic continuous stirring. Experiments were performed at room temperature (20 C 2 C) and
with an oxygen content of approximately 7.5 mg O2 L 1. Dissolved
oxygen was not a limiting factor.
The sludge was taken from a conventional WWTP (Castell Platja
d'Aro, NE Spain; 35,000 m 3 d 1, 175,000 I.E.) with an observed inuent ibuprofen concentration of approximately 10 g L 1 (Dolar et al.,
in preparation).
Different suspended solid concentrations (ranging from 50 to
1000 mgTSS L 1) and ibuprofen concentrations (from 10 to
1000 g L 1) were tested in a total of nine combinations. According
to the initial conditions, different scheduled times for sampling were
determined to occur between 24 and 72 h (shorter intervals for higher
TSS content). The sludge was sampled from the WWTP (average
suspended solid concentration from 1 to 2 gTSS L 1), aerated for 2 h
before use (to minimise the amount of rapidly degradable organic
matter still present) and diluted with tap water to the appropriate
concentration for each batch study.

2.2. Analysis of pharmaceuticals


Aqueous samples (10 mL) were ltered through 0.45 m glass bre
lters and kept in 20-mL glass vials with 1 mL of paraformaldehyde solution at 37% v/v to avoid any further degradation prior to analysis. All of
the samples were well homogenised and frozen at 20 C until their
analysis. Ibuprofen and selected ibuprofen transformation products
(carboxyl ibuprofen (IBU-CBX), 1-hydroxyl-ibuprofen (IBU-1OH) and
2-hydroxyl-ibuprofen (IBU-2OH) (Fig. 1)) were analysed using a UPLC
system (Waters Corp., Mildford, MA, USA) coupled to a triple quadrupolelinear ion trap mass spectrometer (5500 QTRAP, Applied Biosystems, Foster City, CA, USA) in negative ionisation mode.

2.3. Blanks, controls, reproducibility tests and interpretation of results


Several blank tests, with the same conguration as the batch tests
described in Section 2.1 but without ibuprofen, were performed in
parallel, and no signicant contamination was detected (ibuprofen
concentration was always less than 0.32 g L 1).
Tests with ibuprofen (concentration ranging from 10 to 1000 g L1)
but without biomass (to check possible chemical or physical removal)
conrmed that there was no abiotic removal in the system (b 1%) that
would decrease the ibuprofen concentration.
Experimental reproducibility, homogeneity and intrinsic variability
of the nal biodegradation rate values were assessed by performing a
test with a set of six two-litre aerated glass bottles with the same content (1 gTSS L 1 biomass and 10 g L 1 ibuprofen). Almost complete
removal of ibuprofen (nal concentration b 0.08 g L1) was observed
in all of the tests, with a standard deviation of 0.3 g L 1 (samples
at 3, 5 and 24 h).
Removal efciencies were calculated and pseudo-rst-order kinetics
were adjusted with Matlab software. The experimental biodegradation
rate constants (Kbiol; Joss et al., 2006) were obtained for the parent compound for each combination of the batch tests of paragraph 2.1 and,
under specic conditions (100 mgTSS L 1 and 10 gIBU L 1), for the
aforementioned TPs.

298

N. Collado et al. / Science of the Total Environment 433 (2012) 296301

Fig. 1. Structures of: (a) ibuprofen; (b) carboxyl ibuprofen (IBU-CBX); (c) 1-hydroxyl-ibuprofen (IBU-1OH); (d) 2-hydroxyl-ibuprofen (IBU-2OH).

3. Results
3.1. Biodegradation studies on ibuprofen
Aerobic batch tests were run at different initial ibuprofen and solid
concentrations. The removal efciencies obtained are presented in
Fig. 2, illustrating variable degradation rates.
A nal signicant ibuprofen removal was achieved in most of the
tested combinations within three days. The proles shown in Fig. 2 demonstrate that the higher removal rates were obtained at higher concentrations of biomass, with faster and more complete ibuprofen removal.
In contrast, high loads of pharmaceutical compound with low biomass
concentration (50 mgTSS L1) lead to a partial ibuprofen biodegradation (b 10%, 44% and 60% accounting for 10, 100 and 1000 g L1 of
ibuprofen, respectively) and thus slower removal rates.

3.2. ASM-based model for ibuprofen


Due to the low Henry's law constant for ibuprofen (6,10E 06
atm m 3 mol 1) volatilisation can be neglected as a potential removal
pathway (Schwarzenbach et al., 2003). Photodegradation does not
represent a relevant process for the fate of ibuprofen under the tested
conditions (Tixier et al., 2003). These hypotheses were conrmed by
control tests without biomass (b 1% decrease in the initial ibuprofen
concentration, Section 2.3).

Therefore, the most important degradation mechanisms for ibuprofen are sorption into the sludge and biodegradation. The literature suggests that for most of the pharmaceutical compounds, removal in
activated sludge is typically described with pseudo-rst-order or mixed
second-order reaction kinetics (Joss et al., 2006; Schwarzenbach et al.,
2003). The transformation of the total (soluble plus sorbed) concentration of micropollutant is proportional to the concentrations of both
soluble micropollutant and suspended solids with a proportionality
rate constant Kbiol. If sorption equilibrium is assumed, the total concentration can be estimated as a function of the soluble concentration, a
sorption coefcient and the sludge concentration. Thus, the observed decrease in ibuprofen concentration in solution can be expressed as
rbiol


dSIBU Kbiol; IBU  SIBU  XTSS 
1 1

L gSST d
dt
1KD;IBU  XTSS

where SIBU is the soluble compound concentration [g L1], t is the time


[d], Kbiol,IBU is the reaction rate constant [L gTSS1 d1], KD,IBU is the adsorption coefcient [L gTSS1] and XTSS is the suspended solid concentration [gTSSL1]. The latter parameter can be treated as constant for
short-term batch experiments.
Assuming a constant KD,IBU value of 0.007 L gTSS 1 from the literature (Joss et al., 2006), the term KD,IBU XTSS is less than 0.1 for the
batch experiments described in this study (range 0.00350.07,
depending on XTSS) and can thus be neglected (Urase and Kikuta,
2005). The former equation can consequently be simplied as follows:
r biol



dSIBU
1 1
:
K biol; IBU  SIBU  X TSS L gSST d
dt

The experimental data at different biomass and ibuprofen concentrations from the previous section were tted to Eq. (1), and the ibuprofen biodegradation constants were calculated. Table 1 summarises
the corresponding set of Kbiol values obtained and the pertinent R 2
values (which were satisfactory (0.90), except for the batch test at
a low biomass content (50 mgTSS L 1) and high ibuprofen concentration (1000 g L 1)). A correspondence can be observed between
the highest Kbiol values (e.g., 1000 mgTSS L 1 with 10 gIBU L 1)
Table 1
Kbiol,IBU values with 95% condence interval and R2 values in parentheses.
[gTSS L1]
Fig. 2. Ibuprofen removal normalised to the spiked concentration (C0) at the initial time.
The continuous lines correspond to the lowest biomass concentration (50 mgTSS L1);
the discontinuous lines correspond to 100 mgTSS L1, and the dotted and discontinuous
lines correspond to 1000 mgTSS L1.

[gIBU L1]

10
100
1000

50

100

1000

6.12 (0.97)
3.97 (0.90)
0.72 (0.47)

15.70 (0.95)
6.92 (0.97)
2.02 (0.98)

17.44 (0.99)
8.57 (0.98)
4.76 (0.99)

N. Collado et al. / Science of the Total Environment 433 (2012) 296301

and the more pronounced degradation proles obtained (Fig. 2), indicating a high biodegradability. The degradation proles were less pronounced for the lower reaction rate constants.
The Kbiol values obtained range from 0.72 to 17.44 L gTSS1 d1;
these values correspond well with the classication proposed by Joss
et al. (2006), indicating a partial biodegradation (2090%) for 0.1 b Kbiol b 10 and substantial removal for Kbiol values higher than
10 L gTSS 1d 1. Similar Kbiol values (935 L gTSS 1 d 1) were
observed in activated sludge systems (3 g L 1 ibuprofen and
0.51 gTSS L 1), depending on the applied technology (Joss et al.,
2006).
In contrast, lower values at higher biomass concentrations (3.8
6.2 gTSS L 1 at 1.333 L gTSS 1 d 1; Abegglen et al., 2009 and
0.209 L gTSS 1 d 1 at 2.5 gTSS L 1; Urase and Kikuta, 2005) were
obtained for low (0.52 gIBU L 1) and medium (100 gIBU L 1)
ibuprofen concentrations, respectively.
These values also depend on the sludge activity and operating
conditions. Our tests were only performed under aerobic conditions.
Values obtained at concentrations (of ibuprofen or biomass) that
are different by one or more orders of magnitude may not be representative. Thus, the correlation between the different combinations
of ibuprofen concentration, biomass concentration and Kbiol values
becomes essential (Fig. 3). The higher the ibuprofen concentration,
the lower the Kbiol value. A pattern of decreasing Kbiol values with a
decrease in the biomass concentration was also observed.

3.3. Biodegradation studies on ibuprofen and ibuprofen TPs


The formation and removal of ibuprofen TPs were investigated to
obtain valuable information regarding the parent compound metabolic
degradation pathways as well as the possible impact of the TPs on the
environment. The batch test with a solid content of 100 mgTSS L1
and 10 g L 1 ibuprofen was also analysed for ibuprofen TPs within a
period of 72 h. The resulting concentrations (gL1 and mM) are
reported in Table 2 with the corresponding formation percentage versus the initial concentration of the parent compound.
A signicant removal of the three TPs, resulting in a nal concentration of less than 0.33 g L 1, was observed; this nding corresponds
with the literature from Buser et al. (1999), who found removals of
over 90%. According to Zwiener et al. (2002), TPs are expected to
occur as degradation products during sewage treatment at a level accounting for approximately 10% of the ibuprofen input. Based our
data, however, this percentage reaches 32% over 24 h (comprising the

299

three TPs and IBU-2OH (the predominant TP)) but decreases to 3% at


the end of the test. Both ibuprofen and its TPs can be present in raw
wastewater, modifying the ratio of ibuprofen to its transformation
products and potentially explaining such differences.
The relatively low concentrations of IBU-1OH, IBU-2OH and IBU-CBX
in this batch study, together with the rapid decrease in concentration,
indicate that the TPs are easily degradable. IBU-2OH had the higher biodegradability, while the other isomer (IBU-1OH) was not removed
completely in 72 h. However, the nal concentration of IBU-1OH was
rather low, and IBU-1OH was likely to be removed at longer times or
higher biomass contents. Quintana et al. (2005) found similar trends
(easily biodegradable isomers that did not accumulate to higher concentrations). IBU-OH was detected in raw, untreated wastewater but
not in biologically treated wastewater (Buser et al., 1999).
3.4. ASM-based model proposal for ibuprofen and ibuprofen TPs
A simplied ASM-model is proposed for the three TPs analysed
(1-hydroxyl-ibuprofen, 2-hydroxyl-ibuprofen, and carboxyl ibuprofen). The combined equations for each TP represent their formation
according to ibuprofen removal and their further degradation. It is assumed that the metabolic pathways for the formation of the three
ibuprofen TPs are completely independent.
The purpose of this study was to provide a Kbiol value not only for
the parent compound but also for each of its TPs, together with an
individualised yield factor to reect the formation coefcient of
each TP according to ibuprofen degradation. The dened formulas
are Eq. (1), relating to the parent compound (ibuprofen) and the following three equations for the three TPs considered in this study.
The following equation encompasses the formation and removal
for the TP 1-hydroxyl-ibuprofen:
dSIBU1OH
Kbiol;IBU1OH  SIBU1OH  XTSS y1OH  KbiolIBU
dt
 SIBU  XTSS

where Kbiol,IBU-1OH [L gSST 1 d 1] refers to the constant value of the


1-hydroxyl-ibuprofen (IBU-1OH), SIBU-1OH [g L 1] refers to the total
TP concentration in the liquid phase, and y1OH [gIBU-1OH gIBU 1] refers to the yield coefcient (calculated by the formation of the TP as a
function of ibuprofen degradation).
The following equations consider the other two TPs:
dSIBU2OH
Kbiol;IBU2OH  SIBU1OH  XTSS y2OH  Kbiol;IBU
dt
 SIBU  XTSS

Ibup

rofen

[g L -1
]

TS
S

[m
gT
SS

L -1
]

Kbiol [L gTSS-1d-1]

dSIBUCBX
Kbiol;IBUCBX  SIBUCBX  XTSS yCBX  Kbiol;IBU  SIBU
dt
 XTSS
4

Fig. 3. Kbiol,IBU variability among the different combinations of TSS and ibuprofen concentrations. The colour intensity of the graph changes according to the Kbiol value.

where the symbols, as presented for Eq. (2), pertain to 2-hydroxylibuprofen and carboxy-ibuprofen for Eqs. (3) and (4), respectively.
The model was applied successfully, and the experimental data
(TP formation and degradation included) were tted satisfactorily
to the simulated curve, as shown in Fig. 4, leading to the determination of Kbiol and the yield factors (Table 3). The values obtained
show a higher TP formation for IBU-2OH, while the other two TPs
maintain lower concentrations.
No references regarding yield factors for TPs are available in the
literature so far because most of the research published on the topic
investigates only their biodegradation (Quintana et al., 2005), not
their formation coordinated with the parent compound removal. As
a preliminary result, we can afrm that the yield factors obtained illustrate a higher value for IBU-2OH, indicating the predominance of
the formation of this compound compared to those of the other two
compounds. Regarding the Kbiol values, the increase in biodegradation

300

N. Collado et al. / Science of the Total Environment 433 (2012) 296301

Table 2
Concentrations of ibuprofen and its TPs, together with their formation percentage ratio according to the initial parent compound concentration (100 mgTSS L1; 10 g L1
ibuprofen).
% TP/ibuprofen
t (h)

IBU
gL

0
1
18
24
42
48
66
72

10.89
8.89
4.24
3.61
1.29
0.81
0.09
0.06

IBU-1OH

IBU-2OH

mM

gL

5.29E05
4.32E05
2.06E05
1.75E05
6.26E06
3.93E06
4.37E07
2.91E07

0.18
0.31
0.21
0.72
0.43
0.48
0.34
0.33

mM

gL

7.92E07
1.42E06
9.57E07
3.23E06
1.93E06
2.17E06
1.52E06
1.47E06

0.00
1.04
1.64
2.29
1.44
0.93
0.00
0.00

IBU-CBX
1

mM

gL

0.00
4.66E06
7.37E06
1.03E05
6.50E06
4.19E06
0.00
0.00

0.00
0.98
1.21
0.80
0.59
0.58
0.65
0.00

IBU-1OH

IBU-2OH

IBU-CBX

mM

0.00
4.14E06
5.14E06
3.41E06
2.51E06
2.44E06
2.75E06
0.00

1.50
2.68
1.81
6.11
3.65
4.10
2.87
2.78

0.00
8.82
13.95
19.49
12.30
7.93
0.00
0.00

0.00
7.82
9.72
6.44
4.75
4.61
5.21
0.00

is in the following order: IBU-1OH b IBU-CBXb IBU-2OH. The most present yet most biodegradable TP was IBU-2OH, as shown by its higher
Kbiol value.

A model that separately encompasses both the formation and degradation of the three major ibuprofen TPs was suggested. A satisfactory t
was obtained, and the yield factor and Kbiol values were calculated.

4. Conclusions

Acknowledgements

Ibuprofen removal was adjusted successfully to a pseudo-rst-order


kinetic equation at different activated sludge and pharmaceutical compound concentrations under aerobic conditions, obtaining Kbiol values
consistent with the literature. Correlations of Kbiol values with these
two parameters were illustrated. The observed trend corresponds to
higher Kbiol values when the ibuprofen concentration decreases and
when the biomass content increases.
Ibuprofen TP formation and removal were also monitored, and a
complete elimination of each TP was obtained, except for 1OH-IBU,
which showed low residual concentrations at the end of the degradation experiments. A major role for the formation of 2OH-IBU was observed, which also resulted in the consideration of 2OH-IBU as the
most biodegradable transformation product (considering its Kbiol
value).

This study has been co-nanced by the Spanish Ministry of Science


and Innovation and the European Union through the European Regional Development Fund and national research projects (CTM200914742-C02-01, CDTI INNPRONTA ITACA project (IPT-2011102) and
CTQ2010-21776-C02-02, DEGRAPHARMAC), as well as by the Catalan Agency for Administration of University and research grants
(AGAUR, 2009 CTP 00034, MBRMed). Prof. Barcel acknowledges
King Saud University for his visiting professorship.

IBU

IBU-CBX

IBU-2OH

8
6
4
2
0

IBU-1OH

12
10

simulated
experimental

simulated
experimental

2
1
0
3

simulated
experimental

2
1
0
3

simulated
experimental

2
1
0
0

10

20

30

40

50

60

70

80

Time (h)
Fig. 4. Experimental and simulated data, in g L1, for ibuprofen and its TPs (test at
100 mgTSS L1, 10 g L1 ibuprofen).

Table 3
Kbiol and yield values for the ibuprofen TPs (100 mgTSS L1; 10 g L1 ibuprofen).

Kbiol [L gSST1 d1]


y [gTP gIBU1]

IBU

IBU-1OH

IBU-2OH

IBU-CBX

15.7

6
0.1

12
0.4

9.6
0.2

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