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Environmental Technology
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Oxidation of bisphenol A by UV/S2O : Comparison with

UV/H2O2
a

Sung-Hwan Yoon , Seongpil Jeong & Seockheon Lee

Water Environmental Centre, Korea Institute of Science and Technology (KIST) , 39-1
Hawolgok-dong, Seongbuk-gu, Seoul , 136-791 , Republic of Korea
Accepted author version posted online: 27 May 2011.Published online: 19 Dec 2011.

To cite this article: Sung-Hwan Yoon , Seongpil Jeong & Seockheon Lee (2012) Oxidation of bisphenol A by UV/S2O :
Comparison with UV/H2O2 , Environmental Technology, 33:1, 123-128, DOI: 10.1080/09593330.2011.579181
To link to this article: http://dx.doi.org/10.1080/09593330.2011.579181

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Environmental Technology
Vol. 33, No. 1, January 2012, 123128

Oxidation of bisphenol A by UV/S2 O2

8 : Comparison with UV/H2 O2
Sung-Hwan Yoon, Seongpil Jeong and Seockheon Lee
Water Environmental Centre, Korea Institute of Science and Technology (KIST), 39-1
Hawolgok-dong, Seongbuk-gu, Seoul 136-791, Republic of Korea

Downloaded by [UPM] at 19:22 07 January 2015

(Received 4 September 2010; accepted 3 April 2011 )

The UV/S2 O2
8 process was applied to decompose bisphenol A (BPA), which is a representative endocrine-disrupting chemical (EDC), and was comared with the UV/H2 O2 process. The BPA degradation eciency by UV/S2 O2
8 was increased
2
by increasing S2 O8 concentration or decreasing BPA concentration. The presence of humic acid caused an inhibitory
eect. The BPA oxidation rate by UV/S2 O2
8 was increased in the following order: neutral pH (pHi = 7) < acidic pH

(pHi = 4) < basic pH (pHi = 10). The main oxidizing species in the UV/S2 O2
8 system was sulphate radical (SO4 ),

whereas the main oxidizing species in the UV/H2 O2 system was OH radical (OH ). Compared with UV/H2 O2 , the
UV/S2 O2
8 process showed higher performance for not only BPA degradation but also its mineralization, which means

that SO
4 is a more eective oxidant for BPA than the OH . The results shown in this study imply that the SO4 -based
UV/S2 O2
8 process can be an excellent alternative process for the widely used UV/H2 O2 process, with higher remediation
performance.
Keywords: endocrine-disrupting chemical; bisphenol A, UV/S2 O2
8 , UV/H2 O2 , sulphate radical, OH radical.

Introduction
Endocrine-disrupting compounds (EDCs) are natural and
synthetic chemicals that cause adverse eects on humans
and animals by inuencing the endocrine system. They
include natural estrogens, synthetic estrogens and anthropogenic chemicals, and they have been reported to be a
signicant cause of reproductive and sexual disturbance in
animals [1,2]. Various EDCs are released into the aquatic
environment, mainly via the euents of sewage treatment
plants (STPs). The detected concentrations of EDCs in
the aquatic environment are known to range from ng/L
to g/L level [3,4]. Even with those low concentrations,
EDCs can pose a serious threat to the endocrine system of humans and animals. The widespread existence of
EDCs in the aquatic environment implies that EDCs are
not suciently removed by conventional water treatment
processes (e.g. activated sludge, activated carbon, chlorination). Because of the highly hazardous eects on humans
and animals, it is necessary to remove EDCs more eectively from STPs and drinking water treatment plants. For
this purpose, advanced oxidation processes (AOPs) have
been recommended owing to the high potential for the
oxidation of persistent micropollutants such as EDCs, pharmaceutically active compounds and personal care products

Corresponding

author. Email: seocklee@kist.re.kr

ISSN 0959-3330 print/ISSN 1479-487X online

2012 Taylor & Francis
http://dx.doi.org/10.1080/09593330.2011.579181
http://www.tandfonline.com

[5,6]. Generally, AOPs not only decompose EDCs but also

reduce their estrogenic activities [79].
A lot of studies have shown that AOPs are very eective for the oxidative removal of EDCs [10]. Advanced

oxidation processes, which use the hydroxyl radical (OH ,

EOH = 2.7 V as normal hydrogen electrode [NHE]) or sul

phate radical (SO

4 , ESO4 = 2.53.1 V as NHE) as the
main oxidizing species, include O3 , O3 /H2 O2 , UV/H2 O2 ,
UV/TiO2 , Fe(II)/H2 O2 , UV/Fe(III)/H2 O2 , ultrasonic oxidation, electrochemical oxidation, electron-beam radiation,
and UV/S2 O2
8 . Most previous studies on the removal of

EDCs by AOPs employed OH -induced processes (e.g.

O3 , O3 /H2 O2 , UV/H2 O2 , UV/TiO2 , UV/Fe(III)/H2 O2 )

[1115]. Several AOP studies using SO

4 -induced processes have been conducted for the removal of some
persistent organic pollutants (e.g. butylated hydroxyanisole,
atrazine, 2,4-dichlorophenol) [1619]. However, little

research has been conducted using SO

4 -induced pro2
cesses (e.g. UV/S2 O2
8 , heat/S2 O8 ) for the oxidative
removal of EDCs. That is the reason why this study was
conducted.
In this study, bisphenol A (BPA) was selected as the
target EDC because of its frequent detection in the aquatic
environment. Although it has been recently reported that

S.-H. Yoon et al.

BPA has an insignicant hazardous eect on humans at the

concentration range commonly encountered in the aqueous
environment (less than 1 g/L), BPA is still considered to
be one of the most typical EDCs [20]. It is a key monomer in
the production of polycarbonate plastics and epoxy resins.
The aim of this work was to compare the UV/S2 O2
8 process
and the UV/H2 O2 process for the oxidation of BPA.

All the chemicals except humic acid (HA) were of reagent

grade and used as received. Only HA sodium salt purchased
from Sigma-Aldrich was of technical grade. Sodium persulphate (Na2 S2 O8 ) was used as the source of persulphate
(S2 O2
8 ). Ultrapure water (18.2 Mcm) was obtained using
a laboratory water-purifying system (Millipore). A 6 W
low-pressure mercury lamp (Philips, G6T5, = 254 nm)
was used as the light source.

Photochemical experiments
Disodium hydrogen phosphate (Na2 HPO4 ) was added for
maintaining a desired pH, and 0.1 M H2 SO4 and 0.2 M
NaOH were used for pH adjustment. Experiments were
carried out using a cylindrical borosilicate glass reactor (50 mm i.d. 230 mm height). An aqueous solution
(250 mL) containing BPA and an oxidant (S2 O2
8 or H2 O2 )
was poured into the reactor. The solution was irradiated with UV-C light ( = 254 nm) with magnetic stirring. Sample aliquots were intermittently withdrawn for
analysis. Sodium thiosulphate (Na2 S2 O3 ) was immediately added as a quenching reagent into every sample
before high-performance liquid chromatography (HPLC)
and total organic carbon (TOC) analyses, in order to
stop the potential reaction between BPA and persulphate
([Na2 S2 O3 ]/[persulphate] > 10).

Eects of humic acid (HA) and pH

The eect of HA is shown in Figure 2. The dissolved
organic carbon (DOC) concentration of HA stock solution
A

effect of BPA concentration

10 M BPA
20 M BPA
40 M BPA

0.6

0.4

0.2

0.0
0

10

15

20

Irradiation time (min)

Analysis
The concentration of BPA was measured using a Shimadzu
high-performance liquid chromatography (HPLC) system
with a uorescence detector. A C-18 reverse-phase column served as the stationary phase, with 1 mL/min of
the eluent consisting of 50% acetonitrile and 50% 10 mM
phosphoric acid. An excitation wavelength of 229 nm and
an emission wavelength of 309 nm were used to detect
the uorescence. Mineralization eciency was determined
using a Shimadzu TOC analyser. The S2 O2
8 concentrations were determined by the iodometric spectrophotometer
method [21], and H2 O2 concentrations were measured by
the 2,9-dimethyl-1,10-phenanthroline (DMP) method [22].
An Orion 250 pH meter was used for the pH measurements.
A HACH DR 5000 spectrophotometer was employed for
the absorption measurements.

1.0

0.8

1.0

effect of S 2O82- concentration

0.8

[BPA]t / [BPA]0

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Experimental
Materials

Results and discussion

Eects of BPA concentration and S2 O2
8 concentration
The dependence of the BPA degradation eciency on
initial BPA concentration at 100 M S2 O2
and initial
8
pH 4.0 is shown in Figure 1a. The BPA concentration was
changed from 10 to 40 M. The required reaction time
to achieve a certain eciency of BPA degradation (e.g.
90%) increased with the increase in BPA concentration.
The eect of S2 O2
8 concentration at 40 M BPA and initial pH 4.0 is shown in Figure 1b. The S2 O2
8 concentration
was changed from 100 to 400 M. In this case, the required
reaction time decreased with the increase in S2 O2
8 concentration. That is, the BPA degradation by UV/S2 O2
8 could
be accelerated by increasing the ratio of [S2 O2
]/[BPA].
8
The increase of [S2 O2
in the UV/S2 O2
8 ]/[BPA]
8 process

radicals
to
react
with BPA
causes a higher amount of SO
4
for a given amount of BPA, and thus the required reaction
time is shortened.

[BPA]t / [BPA]0

124

100 M S2O820.6

200 M S2O82400 M S2O82-

0.4

0.2

0.0
0

10

15

20

Irradiation time (min)

Figure 1. Eect of (a) BPA concentration ([S2 O2

8 ]0 =100 M)
and (b) S2 O2
concentration
([BPA]
=
40
M)
on BPA degra0
8
dation. pHi = 4 (with 0.2 mM Na2 HPO4 ).

Environmental Technology

1.0

1.0

0.8

[BPA]t / [BPA]0

0.8

[BPA]t / [BPA]0

125

0.6

0.4

0.6

0.4

UV/S 2O8
0.2

0.2

HA-DOC = 0 mg/L
HA-DOC = 8.5 mg/L
HA-DOC = 17 mg/L

2-

w/o alcohols
w/ 10 mM t-butanol
w/ 10 mM ethanol

0.0

0.0
0

Irradiation time (min)

Irradiation time (min)

Figure 2. Eect of humic acid on BPA degradation. [BPA]0 =

10 M, [S2 O2
8 ]0 = 100 M, pHi = 4 (with 0.2 mM Na2 HPO4 ).

1.0

[BPA]t / [BPA]0

0.8

pH 4
pH 7
pH 10

0.8

[BPA]t / [BPA]0

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1.0

0.6

0.6

0.4

UV/H 2O2
0.2

0.4

w/o alcohols
w/ 10 mM t-butanol
w/ 10 mM ethanol

0.0
0

Irradiation time (min)

0.2

0.0
0

Figure 4. Eects of t-butanol and ethanol on the BPA degrada2

tion by (a) UV/S2 O2
8 ([S2 O8 ]0 = 500 M) and (b) UV/H2 O2
([H2 O2 ]0 = 500 M). [BPA]0 = 50 M, pHi = 7 (with 5 mM
Na2 HPO4 ).

Irradiation time (min)

Figure 3. Eect of pH on BPA degradation. [BPA]0 = 10 M,

[S2 O2
8 ]0 = 100 M, pH adjusted with 0.2 mM Na2 HPO4 .

was 85 mg/L. With this HA stock solution, a desired

concentration of HA-DOC was prepared. The BPA degradation eciency decreased with the increase in HA-DOC
concentration. In 6 min, the BPA degradation eciencies corresponding to 0, 8.5 and 17 mg/L HA-DOC were
96.0%, 62.3% and 40.2%, respectively. The presence of
HA-DOC showed an inhibitory eect on the BPA degradation by UV/S2 O2
8 , since HA-DOC acted as a competitive
scavenger for SO
4 radicals and also decreased the light
penetration in the solution.
The eect of pH is shown in Figure 3. Usually, in the
UV/S2 O28 - system, the pH drops to an acidic value owing to
the formation of proton (H+ ) and SO2
4 [23]. However, in
our experiments, the pH drop was insignicant because of
the pH-buering eect of 0.2 mM Na2 HPO4 : pH < 0.3.
The BPA degradation eciency by UV/S2 O2
8 increased
in the following order: neutral pH (pHi = 7) < acidic pH
(pHi = 4) < basic pH (pHi = 10). Although we do not
have a clear explanation for this result, we assume that the

highest eciency at the basic pH is attributable to the most

rapid dissociation of S2 O2
8 to SO4 . The higher eciency
at the acidic pH than at the neutral pH also seems due
to the more rapid decomposition of S2 O2
8 and formation

.
The
acidand
base-catalysed
decomposition
of
of SO
4
persulphate is a well-known phenomenon [24,25]. However, it seems that this pH dependence (pHi 7 < pHi 4 <
pHi 10) is not always apparent in the UV/S2 O2
8 system.
In a previous study by Lau et al. [18], it was reported
that the degradation eciency of butylated hydroxyanisole
(BHA) by UV/S2 O2
8 increases with the increase in initial
pH (pHi = 312). It is inferred that the pH eect on the
UV/S2 O2
8 process is not constant but varies depending on
target pollutants.

Eects of t-butanol and ethanol

The eects of two alcohols, t-butanol and ethanol, on the
degradation of BPA by UV/S2 O2
and UV/H2 O2 are
8
shown in Figure 4a and 4b, respectively. The alcohols were
added at 10 mM for 50 M BPA, corresponding to a 200:1
molar ratio of alcohol versus BPA. Since the reactivity

S.-H. Yoon et al.

1.0

BPA degradation
0.8

UV + 2 mM S2O82UV + 2 mM H2O2
UV + 0.5 mM S2O82-

0.6

UV + 0.5 mM H2O2
UV alone
0.4

0.2

0.0
0

Irradiation time (min)

1.0
UV + S2O82UV + H2O2

0.8

0.6

0.4

BPA mineralization
0.2
0

10

20

30

40

Irradiation time (min)

Comparison between UV/S2 O2

8 and UV/H2 O2
The BPA degradation eciencies by UV/S2 O2
and
8
process
UV/H2 O2 are shown in Figure 5a. The UV/S2 O2
8
was a more eective process than the UV/H2 O2 process.
When S2 O2
8 or H2 O2 was added at 2 mM, the BPA degradation eciencies in 2 min by UV/S2 O2
8 and UV/H2 O2 were
98.8% and 85.3%, respectively. In the case of adding S2 O2
8
or H2 O2 at 0.5 mM, the BPA degradation eciencies in
6 min of UV/S2 O2
8 and UV/H2 O2 were 99.0% and 87.4%,
respectively. For the BPA mineralization also, UV/S2 O2
8
was more eective than UV/H2 O2 (Figure 5b). In 60 min,
the BPA mineralization eciencies by UV/S2 O2
and
8
UV/H2 O2 were 68.6% and 55.7%, respectively. The photodegradation of S2 O2
8 and H2 O2 during the mineralization
experiments was monitored (Figure 5c). The molar extinc1
tion coecients of S2 O2
8 and H2 O2 are 20 and 19.6 M
2
1
cm , respectively [23]. The degradation of S2 O8 and
H2 O2 could be expressed by pseudo-rst-order kinetics:

Ln

Ct
C0


= kt

(1)

where k is the pseudo-rst-order rate constant, C0 is the

initial concentration and Ct is the concentration at a certain
time. The pseudo-rst-order rate constants of S2 O2
8 and
H2 O2 were 0.020 and 0.034 min1 , respectively. That is,
the photodegradation rate of S2 O2
8 was lower than that
of H2 O2 . Since the photodecomposed S2 O2
8 and H2 O2

1.0
S2O82H 2 O2

0.8

0.6

C / C0

Downloaded by [UPM] at 19:22 07 January 2015

[BPA]t / [BPA]0

of t-butanol with SO
4 is greatly dierent from that with

OH , the addition of t-butanol is an eective approach for

dierentiating SO
4 -induced reactions from OH -induced
reactions [17]. Alcohols containing no -hydrogen, such

as t-butanol, are eective scavengers for OH radicals,

but not for SO4 radicals. The bimolecular rate constant

of t-butanol with OH (3.8 108 to 7.6 108 M1 s1 )

5
is c.1000-fold greater than that with SO
4 (4.0 10 to
5
1 1
9.1 10 M s ) [26,27]. On the other hand, alcohols
containing -hydrogen, such as ethanol, react at comparable

rates with OH and SO

4 . The rate constant of ethanol with

9
OH (1.2 10 to 2.8 109 M1 s1 ) is approximately

7
7
50-fold greater than that with SO
4 (1.6 10 to 7.7 10
1 1
M s ) [26,27]. Hence, the change in the oxidation eciency caused by t-butanol makes it possible to dierentiate

between SO
4 -induced reactions and OH -induced reactions. As shown in Figure 4a, the eciency change due
to t-butanol was very small in the UV/S2 O2
8 process compared with the eciency decrease due to ethanol. On the
other hand, as shown in Figure 4b, in the UV/H2 O2 process,
t-butanol caused a great inhibition eect on the degradation
of BPA, similarly with ethanol. These results imply that the

2
SO
4 is the main oxidizing species in the UV/S2 O8 pro
cess, whereas the OH plays the main role in the oxidation
by the UV/H2 O2 process.

[DOC]t / [DOC]0

126

0.4

0.2

2-

Decay of S 2O8 and H2O2

0.0
0

10

20

30

40

Irradiation time (min)

Figure 5. Comparison of UV/S2 O2

and UV/H2 O2 for
8
(a) BPA degradation, (b) BPA mineralization, ([S2 O2
8 ]0 or
[H2 O2 ]0 = 2000 M), (c) degradation of S2 O2
and
H 2 O2
8
([S2 O2
]
or
[H
O
]
=
2000
M).
[BPA]
=
50
M,
pH
2 2 0
0
i =7
8 0
(with 5 mM Na2 HPO4 ).

produce two SO
4 radicals and two OH radicals (Equations (2) and (3)), the result shown in Figure 5c implies that

2
the number of SO
4 radicals produced by UV/S2 O8 was
fewer than that of OH radicals produced by UV/H2 O2 .

S2 O2
8 + hv 2SO4

H2 O2 + hv 2OH .

(2)
(3)

Environmental Technology

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Nevertheless, as shown in Figure 5b, UV/S2 O2

8 showed
signicantly higher performance than UV/H2 O2 for
the removal and mineralization of BPA. This implies

that the SO
4 is more eective than the OH for the oxida2
tion of BPA. Therefore, the UV/S2 O8 process can be an
excellent alternative to the widely used UV/H2 O2 process,
with higher remediation performance. The redox potentials

of OH and SO
4 are 2.7 and 2.6 VNHE , respectively. In
our assumption, due to the lower redox potential (i.e. lower

reactivity), SO
4 is more stable and is able to transport to
greater distances (i.e. greater mass transfer rate) in aque

ous media than OH . Thus, SO

4 is able to reach nearby

compounds in the solution bulk more eectively than OH .

In our opinion, this is the reason that SO4 can be a more

eective oxidant than OH .

Conclusions
This study focused on the comparison of UV/S2 O2
8 and
UV/H2 O2 for the oxidation of BPA. The BPA oxidation
eciency by UV/S2 O2
8 could be increased by increasing the ratio of [S2 O2
8 ]/[BPA]. The increase in HA
concentration showed an inhibitory eect on the BPA oxidation by UV/S2 O2
8 . The BPA oxidation eciency by
UV/S2 O2
was
increased
in the following order: neutral pH
8
(pHi = 7) < acidic pH (pHi = 4) < basic pH (pHi = 10).
The main oxidizing species in the UV/S2 O2
8 system was
sulphate radical, whereas the main oxidizing species in
the UV/H2 O2 system was OH radical. The UV/S2 O2
8
process was more eective for not only BPA removal
but also BPA mineralization than the UV/H2 O2 process,

which means that SO

for
4 is a more eective oxidant

BPA than OH . This study implies that the SO

4 -based
UV/S2 O2
8 process can be an excellent alternative to the
widely used UV/H2 O2 process, with higher remediation
performance.

[6]
[7]

[8]

[9]

[10]

[11]

[12]

[13]
[14]
[15]

[16]

[17]

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