Photochemistry of bisphenol F in aqueous solutions: A mechanistic study

Article abstract of DOI:10.1016/j.jphotochem.2015.03.008

In the present work aqueous photochemistry of bisphenol F has been studied by means of stationary (282 nm) and laser flash photolysis (266 nm). Photoionization with formation of hydrated electron - phenoxyl radical pair was observed to be the main primary photochemical process (φ_mono = 2 × 10^-2). Phenoxyl radical decays in recombination and reaction with superoxide anion radical formed during scavenging of hydrated electron by dissolved oxygen. The quantum yield of BPF photodegradation was evaluated to be 2 × 10^-3 upon 282 nm exposure. The main primary product of BPF photolysis determined by LC-MS is hydroxylated BPF.

Full text of DOI:10.1016/j.jphotochem.2015.03.008

Journal of Photochemistry and Photobiology A: Chemistry 305 (2015) 45–50
Contents lists available at ScienceDirect
Journal of Photochemistry and Photobiology A:
Chemistry
journal homepage: www.elsevier.com/locate/jphotochem
Photochemistry of bisphenol F in aqueous solutions: A mechanistic
study
Victoria Salomatova a, , Ivan Pozdnyakova,b, Peter Sherin c, Vjacheslav Grivin a,
*
Victor Plyusnin a,b
a
V.V Voevodsky Institute of Chemical Kinetics and Combustion, 3 Institutskaya Street, 630090 Novosibirsk, Russian Federation
Novosibirsk State University, 2 Pirogova Street, 630090 Novosibirsk, Russian Federation
International Tomography Center, 3a Institutskaya Street, 630090 Novosibirsk, Russian Federation
b
c
A R T I C L E I N F O
A B S T R A C T
Article history:
In the present work aqueous photochemistry of bisphenol F has been studied by means of stationary
(282 nm) and laser flash photolysis (266 nm). Photoionization with formation of hydrated electron –
phenoxyl radical pair was observed to be the main primary photochemical process (fmono = 2 ꢀ10ꢁ2).
Phenoxyl radical decays in recombination and reaction with superoxide anion radical formed during
scavenging of hydrated electron by dissolved oxygen. The quantum yield of BPF photodegradation was
evaluated to be 2 ꢀ10ꢁ3 upon 282 nm exposure. The main primary product of BPF photolysis determined
by LC–MS is hydroxylated BPF.
Received 2 February 2015
Received in revised form 11 March 2015
Accepted 12 March 2015
Available online 14 March 2015
Keywords:
Bisphenol F
ã 2015 Elsevier B.V. All rights reserved.
Endocrine disruptor
Flash photolysis
Photoionization
Photodegradation
Phenoxyl radical
Hydrated electron
1. Introduction
has been widely detected in the environment and food products
[11–14].
In the few past decades scientific concerns related to endocrine-
disrupting chemicals (EDCs) and their effects on living organisms
have increased. EDCs are both natural and synthetic compounds
which affect on living organisms through receptor-mediated
processes mimicking endogenous hormones by inhibiting normal
hormonal activities and producing number of disorders in
endocrine functions and reproduction of living organisms [1–3].
Bisphenol F (4,40-dihydroxydiphenylmethane, BPF) is widely
used in production of polycarbonate plastics, epoxy resins,
adhesives, coatings for drink packages and food cans. As well as
its structural analog bisphenol A, BPF refers to EDCs and was
reported to have a 48-h EC50 of 56.0 mg Lꢁ1 against Daphnia magna
and estrogenic activity comparable to that of BPA [4–7]. Besides the
endocrine disrupting effect, BPF also was found to have genotoxic
potential [8,9]. In recent years production and consumption of
bisphenols which can substitute BPA in industrial applications,
including BPF, have tended to increase [10]. As a consequence, BPF
Conventional treatment techniques are not effective enough for
the removal of majority of EDCs, while photochemical and
photocatalytic processes have proved themselves as perspective
methods for water purification and disinfection from these
compounds.
In recent years a broad number of investigations attempting to
decompose bisphenols using photochemical approaches were
reported [15–23]. For this purpose various technologies were
applied, such as direct photolysis [15,16], TiO2 photocatalyst
[17,18], cyclodextrin-enhanced photolysis [16] and advanced
oxidation processes [15] including photo-Fenton reaction [19]
and UV/H2O2 combination [20]. Also, the influence of different
natural additives, such as dissolved organic matter [21], ferric salts
[22] and inorganic anions [23], was studied. Despite the efforts
made on studying the photodegradation of BPF, direct photolysis of
BPF has been only investigated up to a limited extent. Also, there is
almost no information about mechanistic aspects regarding the
photochemistry of BPF without any additives. This work is aimed to
study photochemistry of BPF in aqueous solutions with the focus
on determination of primary photochemical processes, short-lived
intermediates and their transformation products.
* Corresponding author. Tel.: +7 383 3332385.
E-mail address: salomatova@kinetics.nsc.ru (V. Salomatova).
http://dx.doi.org/10.1016/j.jphotochem.2015.03.008
1010-6030/ã 2015 Elsevier B.V. All rights reserved.

46
V. Salomatova et al. / Journal of Photochemistry and Photobiology A: Chemistry 305 (2015) 45–50
Fig. 1. Transient absorption spectra recorded after 0.05 (1), 0.4 (2), 0.8 (3), 4 (4) and
48 (5) s after the laser excitation of BPF air-free aqueous solution. Insert – the
m
structural formula of BPF.
2. Experimental
BPF was purchased from Test Scientific and Technology Co. Ltd.
(St. Louis, MO) (GC grade >99.0%) and used without further
purification. Acetonitrile was of HPLC grade (Cryochrom). The
reaction solutions were prepared with doubly distilled water. The
BPF concentration was within the range (2–4) ꢀ 10ꢁ4 M. All
photochemical experiments were performed in a 1 cm quartz cell
in air-equilibrated or air-free (argon purging) solutions at initial pH
6.5, temperature 298 K and atmospheric pressure.
Fig. 2. (a) – The dependence of the (1) hydrated electron (lreg = 720 nm, argon-
saturated solution) and (2) ArOꢃ
lreg = 400 nm, air-saturated solution) yields on
laser excitation energy in log–log coordinates; (b) – the dependence of the observed
(
quantum yield of the hydrated electron on excitation energy.
were mixed using the linear gradient 30–70% of B (0–15 min). The
injection volume was 40 mL. Mass spectra were acquired in the
negative mode in the m/z range of 25–350. The instrument
parameters were set as: end plate offset ꢁ500 V; capillary voltage
4000 V; nebulizer pressure 1 bar; dry gas flow 8 l/min; dry gas
temperature 200 ꢂC. The MS calibration was performed with an
injection of the sodium formate cluster calibration solution. The
most intense ions were fragmented using collisional induced
dissociation in the MS/MS mode. The obtained data were analyzed
with DataAnalysis software 4.0 (Build 275, Bruker Daltonics,
Germany).
UV absorption spectra were recorded using an Agilent
8453 spectrophotometer (Agilent Technologies). The laser flash
photolysis setup based on an LS-2137U Nd:YAG laser (Lotis TII,
Belarus) with excitation wavelength of 266 nm, pulse duration of
5–6 ns, illumination spot area of 0.03 cm2, and energy per pulse up
to 10 mJ was used in the time-resolved experiments; the device
was similar to that described in [24]. Time resolution of the setup
was ca. 50 ns. XeBr excimer lamp with excitation wavelength of
282 nm was used for steady-state irradiation. Lamp and laser
intensities were measured by means of SOLO 2 laser power meter
(Gentec EO).
3. Results and discussion
The irradiated samples were quantified with a high perfor-
mance liquid chromatography (HPLC) Agilent LC 1100 system,
equipped with diode array detector. The separations were
performed using Zorbax Eclipse XBD-C18 column (4.6 ꢀ150 mm,
The evolution of transient absorption spectra obtained during
the flash photolysis of air-free aqueous solution of BPF is shown in
Fig. 1. These spectra exhibit the characteristic bands with maxima
at 720 nm and 400 nm, which disappear with different rates
indicating the formation of at least two different species. The broad
band with mꢁaximum at 720 nm is a clear evidence of hydrated
80 Å, 5 mm) with a flow rate 1.0 mL/min in the isocratic elution of
0.05% (v/v) trifluoroacetic acid (TFA) in water/acetonitrile mixture
with equal parts of each solvent (50/50, v/v). The injection volume
was 50 mL. The chromatograms were recorded at 260, 280, 320,
360 and 450 nm; the analysis of the obtained results was
performed by Agilent ChemStation software.
The photodegradation products were analyzed with HPLC
electrospray ionization mass spectrometry (HPLC-ESI-MS) system:
ultra-HPLC system UltiMate 3000RS (Dionex, Germany) connected
with high-resolution ESI time-of-flight mass spectrometer maXis
4G (Bruker, Germany). HPLC separations were made using the
same column and flow rate as it was described above. Mobile
phases A (0.1% formic acid in water) and B (0.1% formic acid in ACN)
electron (eaq
,
e
720 = 2.27 ꢀ104 Mꢁ1 cmꢁ1 [25]) formation upon
flash excitation [26]. The peak around 400 nm can be assigned to
the absorption of BPF phenoxyl radical [27]. Thus, UV excitation of
BPF results in photoionization with formation of hydrated electron
– phenoxyl radical (ArOꢃ) pair which is a typical primary process in
aqueous photochemistry of phenols and bisphenols [28–30].
In order to determine the quantum yield of photoionization,
transient absorption at 720 nm was measured as a function of the
laser pulse energy in deaerated solution. The dependence has a
nonlinear character with a slope of 1.5 in log–log coordinates

V. Salomatova et al. / Journal of Photochemistry and Photobiology A: Chemistry 305 (2015) 45–50
47
recorded in airꢁ-equilibrated solution the strong absorption
belonging to eaq is not observed at times after 0.4 s (Fig. 3).
Comparison of amplitude of ArOꢃ absorption at 400 nm ( A400
m
D
)
with concentration of hydrated electron allows to estimate
absorption coefficient of first one, e400 (ArOꢃ) = 3200 Mꢁ1 cmꢁ1
(Fig 3, insert).
During analysis of kinetic curves obtained in air-equilibrated
solutions in broad range of registration wavelength, it was found
that they have complex nature with three possible to distinguish
components (Fig. 4a). Initial part of kinetic curves with
a
monoexponential decay (ꢄ1
m
s) could be assigned to transition
absorption of BPF triplet excited state. Second part apparently
belongs to phenoxyl radical decay and also long-lived absorption
(t > 400 ms) is observed which could be explained by formation of
intermediate/final photoproducts of ArOꢃ reactions. Thus, the set of
kinetics curves obtained in air-saturated solutions was processed
by following formula (Fig. 4a):
ðA2 ꢁ A3Þ
D
A ¼ A1expðꢁkTtÞ þ
þ A3
(2)
ð1 þ kobstÞ
where A1,A2 and A3 corresponds to amplitudes of the triplet state,
phenoxyl radical and the long-lived absorption, accordingly; kT and
kobs observed rate constants of BPF triplet state decay by oxygen
quenching and disappearance of ArOꢃ radical in second-order
Reactions (3.1, 3.2, see below).
The triplets of phenols were reported to have weak broad
absorption in visible region (ꢅ430 nm) and lifetime of a few
microseconds under aerated conditions [32,33]. Obtained spec-
trum supposed to belong BPF triplet state (Fig. 4b, A1) matches well
this data.
The extracted spectrum of phenoxyl radical (Fig. 4b, A2) is in a
good agreement with the described ones in literature [27]. The
decay of ArOꢃ obeys second-order law both in air-free and
air-saturated solutions and can be explained by reaction between
two ArOꢃ radicals or reaction with superoxide-anion radical [34]:
Fig. 3. Transient absorption spectra recorded after 0.05 (1), 0.4 (2), 0.8 (3), 4 (4) and
48 (5) s after the laser excitation of BPF air-saturated aqueous solution. Insert – the
m
dependence of A2 on the initial concentration of
a hydrated electron upon
photolysis of BPF.
(Fig. 2a) and could be adequately fitted by Eq. (1). This fact
indicates that two-photon ionization plays a significant role under
the laser excitation of BPF.
D
A
720 = a ꢀ I + b ꢀ I2 (1)
Indeed, the plot A720/I against I (Fig. 2b) gives a straight line
supporting validity of Eq. (1). The cut-off on the ordinate allows to
estimate the quantum yield of monophotonic ionization at 266 nm
ArOꢃ + ArOꢃ —(k1)! products (3.1)
excitation, fmono = 2 ꢀ10ꢁ2
.
In the air-saturated solutions the hydrated electron decays
rapidly in reactioꢁn with dissolved oxygen yielding superoxide-
anion radical O2 (k = 2 ꢀ1010 [31]) and in transient spectra
ꢁꢃ
ArO+ O2 —(k2)! ArO(O2)ꢁ (3.2)
Fig. 4. (a) – Kinetics curves registered during photolysis in air-equilibrated BPF solution at 300 (1), 350 (2), 400 (3), 450 (4) nm; (b) – Amplitudes obtained during processing
the set of kinetics curves by formula (2): A1 (1), A2 (2), A3 (3).

48
V. Salomatova et al. / Journal of Photochemistry and Photobiology A: Chemistry 305 (2015) 45–50
Fig. 6. (a) – Chromatograms at 280 nm of (1, dash line) air-equilibrated and (2, solid
line) air-free BPF solution irradiated 45 min by XeBr exilamp; (b) – normalized
optical spectra of BPF and P1; (c) – dependence C/C0 on irradiation time during
photolysis in (1) air-equilibrated and (2) air-free BPF solution.
D
At times longer than 3 ms the disappearance of transient
absorption at 400 nm can be described by the following formula:
ðA2 ꢁ A3Þ
D
A400
¼
þ A3
(4)
ð1 þ kobstÞ
In argon-saturated solutions O2ꢁ is not formed and ArOꢃ could
disappear in Reaction (3.1) only. So, kobs should be the linear
function of
A400 (t = 0) = A2:
Fig. 5. (a) – The dependence of kobs of ArOꢃ decay on A2 for (1) – air-equilibrated
solutions, (2) – air-free solutions; (b) – Kinetics curves at 400 nm obtained during
photolysis of (1) aerated and (2) air-free BPF solution.
D
Scheme 1. Photolysis of BPF in air-equilibrated conditions.

V. Salomatova et al. / Journal of Photochemistry and Photobiology A: Chemistry 305 (2015) 45–50
49
Table 1
LC–MS results of BPF photodegradation in air-equilibrated solutions.
Retention time, (min)
3.4
(m/z)
Proposed structure
Commentaries and calculated formula
P5, C7H9O3
139.037
3.6
231.062
P4, Doubly hydroxylated BPF, C13H12O4
4.6
5.8
121.027
213.052
P3, C7H6O2
P2, C13H10O3
6.2
215.068
P1, main product of BPF photolysis, C13H12O3
8.2
199.075
Initial compound BPF, C13H12O2
2k1
the presence of oxygen the value of (2 k1 + k2) = 16.6 ꢀ109 Mꢁ1 sꢁ1 is
2.3 times higher than 2k1 indicating considerable contribution of
Reaction (3.2) in total ArOꢃ decay. Transient absorption at 400 nm
reaches a constant value at approximately 3 ms after excitation
both in aerated and air-free solutions indicating the formation of
intermediate/final photoproducts of ArOꢃ reactions (Fig 5b).
Stationary irradiation of BPF solutions at 282 nm (XeBr-
excilamp) leads to its disappearance with quantum yield
2 ꢀ10ꢁ3 with formation one main product P1 at initial stages of
photodecomposition (Fig. 6a, c). P1 possessing higher polarity than
BPF and optical spectrum close to the initial compound (Fig. 6b)
was identified as hydroxylated BPF (m/z 215.068, C13H12O3). In air-
free conditions quantum yield of BPF degradation is roughly
4 times lower (Fig. 6c) and P1 forms in rather lower amount than in
air-equilibrated solutions (Fig. 6a). These facts indicate that P1
apparently forms via Reaction (3.2) and oxygen plays a significant
kobs
¼
A2
eArO
where
e
ArO is the absorption coefficient of ArOꢃ radical at 400 nm,
k1 is the rate constant of Reaction (3.1).
In the presence of oxygen formula (4) is not precise but still
could be used as a simple approximation of real complex decay of
ArOꢃ radicals with:
2k1 þ k
2A2
kobs
¼
eArO
where k2 – the rate constant of Reaction (3.2).
Indeed, the treatment of set of kinetic curves obtained for
different initial ArOꢃ concentration at 400 nm (Fig. 5) by formula
(4) gives a good linear dependence of kobs from A2 (Fig. 5a) in both
air-free and air-saturated solutions. The value of rate constant of
Reaction (3.1) was determined as equal to 2k1 = 7.4 ꢀ109 Mꢁ1 sꢁ1. In

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V. Salomatova et al. / Journal of Photochemistry and Photobiology A: Chemistry 305 (2015) 45–50
role in photodegradation of BPF. Along with P1 formation of other
products of BPF oxidation and hydroxylation occurs which are
listed in Table 1 and Table 1S (supplemental materials). On the
basis of obtained data the tentative scheme (Scheme 1) of BPF
photolysis under air-equilibrated conditions was proposed which
includes formation of the products of deep oxidation (P2) and C—C
bond cleavage (P3). Highly hydroxylated products P4 and P5 are
probably formed upon secondary photolysis of P1.
UV-method was found to be sufficiently effective way for BPF
removal from water, but obviously this method is needed in further
improvements and modifications to reach endurable results. One
of the perspective and currently upcoming way is using of
cyclodextrins-based technologies [16,30,35]. Preliminary studies
showed that complexation with CD leads to 3-times increasing of
photoionization yield of BPF.
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The work was financially supported by the Russian Foundation
for Basic Research (No. 14-03-00692_a). HPLC and MS measure-
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Scientific Foundation (No. 14-14-00056) and RFBR (No. 14-03-
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