Effect of irradiation intensity on rate and selectivity of photosensitized oxidation of dibutyl sulfide over C70 fullerene

Article abstract of DOI:10.1134/S0018143915030029

Photoinitiated oxidation of dibutyl sulfide (DBS) with air oxygen in a toluene solution of C₇₀ fullerene during irradiation with visible light at a wavelength of 500-700 nm results in the formation of dibutyl sulfone as a main detected product, dibutyl sulfoxide, and butanal. A change in the intensity of radiation incident on the reaction mixture from 2.2 to 44 mW/cm² insignificantly increases the quantum efficiency of the DBS consumption from 4.5 to 5.9%. The selectivity for sulfoxide increases during the process, while selectivity for sulfone decreases.

Full text of DOI:10.1134/S0018143915030029

ISSN 0018ꢀ1439, High Energy Chemistry, 2015, Vol. 49, No. 3, pp. 167–172. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © A.V. Arsentyev, A.V. Vorontsov, V.N. Parmon, 2015, published in Khimiya Vysokikh Energii, 2015, Vol. 49, No. 3, pp. 194–199.
PHOTOCHEMISTRY
Effect of Irradiation Intensity on Rate and Selectivity
of Photosensitized Oxidation of Dibutyl Sulfide over C70 Fullerene
A. V. Arsentyev, A. V. Vorontsov, and V. N. Parmon
Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences,
pr. Akademika Lavrent’eva 5, Novosibirsk, 630090 Russia
eꢀmail: a_voronts@yandex.ru; voronts@catalysis.ru
Received October 28, 2014
Abstract—Photoinitiated oxidation of dibutyl sulfide (DBS) with air oxygen in a toluene solution of C70
fullerene during irradiation with visible light at a wavelength of 500–700 nm results in the formation of dibutyl
sulfone as a main detected product, dibutyl sulfoxide, and butanal. A change in the intensity of radiation inciꢀ
dent on the reaction mixture from 2.2 to 44 mW/cm2 insignificantly increases the quantum efficiency of the
DBS consumption from 4.5 to 5.9%. The selectivity for sulfoxide increases during the process, while selecꢀ
tivity for sulfone decreases.
DOI: 10.1134/S0018143915030029
Photoinitiated (photosensitized and photocataꢀ toluene solution. The choice of С70 as the photocataꢀ
lytic) processes have been actively investigated lyst is due to the fact that it absorbs visible light in a
with the goal of destruction of air and water pollutants wider range compared with С60 fullerene.
[1–4] as well as for production of hydrogen using sunꢀ
light [5–8]. Photocatalytic reactions can be used as
stages in organic synthesis [9]. Singlet oxygen 1О2 can
be formed during interaction of a photoexcited moleꢀ
cule Pc* with triplet oxygen 3О2, which selectively
reacts with alkenes [10, 11], sulfides [13–15], and disꢀ
ulfides [16] yielding various oxidation products [17].
Another reaction pathway of photoexcited Pc* is elecꢀ
tron transfer between the reactant and Pc* [18], which
results in products of oxidation [19, 20] or hydroxylaꢀ
tion [21], cycloaddition of the reactants [22], and
many other transformations [23]. Hence, excited Pc*
molecules function as photosensitizers and photocatꢀ
alysts for various reactions.
EXPERIMENTAL
The chemicals used were toluene of special purity
grade OSChꢀ22ꢀ5 (Reakhim) as the solvent, С70
fullerene of 99% purity (Aldrich), dibutyl sulfide Bu2S
of 96% purity (GC) (Aldrich), dibutyl disulfide of 98%
purity (Aldrich), and butyraldehyde (Vekton, Russia).
The kinetics of the photosensitized oxidation reacꢀ
tion of dibutyl sulfide with air oxygen was investigated
in a toluene solution in 20ꢀmL scintillation vials used
as a static reactor. The choice of toluene as the solvent
is due to high solubility of fullerenes in it, which is
1.4 g/L [33]. The experimental setup is schematized in
Fig. 1. The reaction mixture was prepared by adding
μL of dibutyl sulfide and an accurately measured
aliquot of naphthalene (~12 mg) to 10 mL of 0.21
C70 fullerene solution in toluene. Naphthalene was
used as an internal standard for quantitative chroꢀ
matographic determination of the reactants and prodꢀ
ucts.
Fullerenes were first identified in 1985 [24] and are
promising photocatalysts and photosensitizers in
organic reactions, since their molecules absorb visible
light, participate in electron transfer reactions, and are
capable of 1О2 generation [25] with a high quantum
efficiency reaching 81 15% and 96 4% for С70 [26]
and С60 [27] benzene solutions, respectively. In 1994,
С60 and С70 fullerenes were first used for photocataꢀ
lytic hydroperoxidation of alkenes with oxygen [28].
These fullerenes either in dissolved state or deposited
on solid supports were used in the oxidation reactions
of alkenes [29, 30] or sulfides [31] and in benzene
hydroxylation [32].
17.5
μ
M
A vial was secured with clamps above a LED lamp
(Fig. 1). A narrow fluoroplastic tube was introduced to
a reaction mixture through an opening in a fluoroplasꢀ
tic stopper, through which air was supplied with a flow
rate of 100 mL/min. Airꢀcooling of the reactor with a
fan allowed maintaining the reactor temperature close
Despite the profound interest in fullerenesꢀsensiꢀ to room temperature. A 10ꢀW light emitting diode
tized organic synthesis reactions, the kinetics of these lamp SDOꢀ2ꢀ10 (ASD Corporation, Hong Kong)
reactions was not studied. In this work, we investigated with a ZhSꢀ17 light filter transmitting light in the
the dibutyl sulfide oxidation reaction with air oxygen range of 480–800 nm was used as a light source. The
photosensitized by visible light with С70 fullerene in a light intensity was measured using a 20ꢀmL Pyrex vial
167

168
ARSENTYEV et al.
Radiant power
density,
W/(nm cm)
2
µ
Absorbance
6
0.35
0.30
0.25
0.20
0.15
0.10
0.05
0
400
350
300
250
200
150
100
50
1
1
2
3
4
2
3
4
5
0
300 400 500 600 700 800 900
Wavelength, nm
Fig. 2. Absorption spectrum of 8.9 µM solution of C in
70
toluene and spectrum of radiant power density at different
distances of the reaction mixture from the LED lamp, cm:
(1) 1, (2) 4, (3) 8, and (4) 11.
Fig. 1. Schematic representation of the setup for photocatꢀ
alytic oxidation of dibutyl sulfide: ( ) – air supply tubing,
) 20ꢀmL Pyrex vial,
) SDOꢀ2ꢀ10 light emitting diode
) laboratory stand with clamps.
1
3
(
2
) Teflon lid with two holes, (
The reaction mixture was analyzed using a
Hewlett Packard 5890 gas chromatograph equipped
with a 30ꢀm CPꢀSil 8 CB capillary column (Agilent)
(4
) ZhSꢀ17 light filter, (
5
lamp, and (
6
and a flameꢀionization detector. An aliquot (~50
was taken from the reaction mixture with a 1ꢀmL
syringe, and next a 1ꢀ L sample was introduced into
μL)
of 25 mm in diameter, filled with the reaction mixture,
mounted at different distances from the light source.
μ
an injector of the chromatograph. The chromatograph
was calibrated using a toluene solution containing
known concentrations of dibutyl sulfide, dibutyl sulꢀ
foxide, dibutyl sulfone, dibutyl disulfide, and butyralꢀ
dehyde. Qualitative identification of the gaseous prodꢀ
ucts was performed with a CPꢀ3800 gas chromatoꢀ
graph with a mass spectrometric detector based on a
Saturn 2000 ion trap (Varian).
Spectral irradiance was measured close to the vial
bottom using an ILT950 spectroradiometer (Internaꢀ
tional Light Technologies). The absorption spectrum
of a 8.9 μM С70 fullerene solution in toluene in a 1ꢀcm
path length cell is presented in Fig. 2. The C70 concenꢀ
tration used was 24ꢀfold less than in experiments with
partial Bu2S oxidation due to a too high optical density
of the reaction mixture. The spectrum was recorded
with a Lambda 35 spectrophotometer (Perkin Elmer).
The clearly pronounced absorption maxima are
observed: at 380 and 470 nm in the UV range and the
visible range, respectively. In the long wavelength
RESULTS AND DISCUSSION
After switching the LED light source on in the
presence of air stream and dissolved C70, a decrease in
region of
λ > 700 nm, the absorbance becomes negliꢀ
concentration of the reactant dibutyl sulfide (Bu2S
)
gible, being as low as about 0.05. Hence, the light in
the wavelength range 480–700 nm was considered for
the irradiance calculations. The spectral radiant power
density, transmitted through the ZhSꢀ17 light filter, at
different distances from the lamp is also presented in
Fig. 2. There is an intense peak having a maximum at
555 nm and spreading from 500 to 700 nm. Integration
of the spectral radiant power density curves in the
range of overlap of the C70 fullerene absorption specꢀ
trum with the spectrum of the light emitting diode
(LED) lamp from 490 to 700 nm provides the irradiꢀ
ance values of 43.9, 10.5, 3.6, and 2.2 mW/cm2 for disꢀ
tances from the lamp of 1, 4, 8, and 11 cm, respecꢀ
tively.
and the formation of the set of products of its partial
oxidation were observed. The qualitative composition
of the reaction mixture was determined using the gas
chromatograph coupled with a mass spectrometric
detector. Dibutyl sulfoxide (Bu2SO), dibutyl sulfone
(
Bu2SO2), and butyraldehyde (C3H7CHO) were the
major products. The formation of minor amounts of
dibutyl disulfide (Bu2S2) was detected. The overall
reaction of photosensitized Bu2S oxidation can be preꢀ
sented by formal equation (1):
C
70
Bu2S + O2 + hν
xBu2SO + yBu2SO2
(1)
+
zBu2S2 + wC3H7CHO.
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EFFECT OF IRRADIATION INTENSITY ON RATE AND SELECTIVITY
169
Average quantum efficiency of Bu2S consumption and formation of main products with different irradiances of the reaction
mixture
Irradiation intensity,
mW/cm2
Quantum efficiency
of consumption of Bu2S, %
Quantum efficiency
of formation of Bu2SO, %
Quantum efficiency
of formation of Bu2SO2, %
43.9
10.5
3.6
5.9
5.5
5.5
4.5
1.1
1.0
1.2
1.3
1.3
0.59
0.58
0.38
2.2
This reaction is a photoinitiated transformation imum radiant power of 43.9 mW/cm2 observed at a
requiring the presence of a photosensitizer, light, and distance of 1 cm between the vial and the LED lamp.
oxygen, which was confirmed by the following set of
experiments. First, the initial rate of Bu2S consumpꢀ
tion in the absence of the fullerene and under a maxiꢀ
mal radiation intensity was 55ꢀfold lower in compariꢀ
son with the experiment in the presence of the
It may be assumed that gram amounts of a sulfide
can be oxidized for an irradiation time of 8 h at an
increased power of the light source or under sunlight.
Figure 4 shows the dependence of the rate of dubuꢀ
tyl sulfide consumption upon the irradiance as
obtained from the slopes of the approximating linear
functions of the rate curves plotted in Fig. 3. The
dependence of the consumption rate on the radiation
intensity is described well by a straight line passing
through the origin. This indicates the singleꢀphoton
nature of the observed photoinitiated process, whose
quantum efficiency only weakly depends on the light
intensity.
fullerene and was 8.4
×
10–6 mol/(L min). Only trace
amounts of Bu2SO and Bu2SO2 were detected among
the products in this experiment. These data confirm
the role of fullerene as a photosensitizer. Second,
replacing air pumped through the reaction mixture by
argon also resulted in a slight decrease of the reactant
concentration in the solution during the process,
although the photoinduced oxidation did not occur
under these conditions because of the absence of oxyꢀ
gen. We suggest that the concentration change is due
to the experiment protocol, at which the reactant conꢀ
centrations can vary as a result of both evaporation of
the components of the reaction mixture and nonoxiꢀ
The table presents the quantum efficiencies of the
Bu2S consumption calculated by Eq. (2).
dC
V
(2)
φ = −
,
dt IN N A
is the rate of change in the dibutyl sulfide
is the volume of the reaction mixꢀ
dative reactions. The Bu2S consumption rate was 13
×
10–6 mol/(L min). However, the products of the partial
oxidation of Bu2S were not detected. In the third
experiment, the change in the reaction mixture comꢀ
position was monitored without irradiation. The rate
of dibutyl sulfide consumption in this experiment was
dC
dt
where
concentration,
V
ture, NA is Avogadro’s number, IN is the is the number
of photons in the range of 480–700 nm getting into the
system per unit time. It can be seen that the quantum
efficiency of the dibutyl sulfide consumption increases
slightly with an increase of the intensity of irradiation
of the reaction mixture.
0.2
×
10–6 mol/(L min), and likewise no products of
partial Bu2S oxidation were detected after 80 min of
the experiment.
In another set of experiments, the intensity of radiꢀ
ation incident on the reaction mixture was varied by
changing the distance between the bottom of the vial
and the LED lamp. The obtained kinetic curves for the
concentrations of Bu2S and reaction products are preꢀ
sented in Fig. 3. It can be seen that the changes in the
concentrations are described quite well by linear funcꢀ
tions. The Bu2S consumption rate during the process
increases with an increase in the radiation intensity,
thereby confirming that the transformations occur in
the mode of photoinitiation. It is also seen that the
radiation intensity affects the product formation rates;
for example, the Bu2SO and butanal formation rates
decrease faster with a decreasing in radiation intensity
than the rate of Bu2SO2 formation. The selectivity for
the products is considered in more detail below. The
Figure 5 presents selectivity values for the detected
products of the partial oxidation of Bu2S with the same
duration of the irradiation process of 21 min, as well as
the total yield in terms of sulfur atoms as found by
summing the selectivities for Bu2SO and Bu2SO2 and
the doubled selectivity for Bu2S2. The selectivity was
calculated as the ratio of the amount of the product to
the amount of Bu2S consumed. We see that the total
yield in terms of sulfur atoms only slightly varies with
a change in the radiation intensity, being in the range
of 35–40%. This figure can be associated with the forꢀ
mation of sulfurꢀcontaining products that cannot be
detected by the methods used. Note that the values of
selectivity for the products of partial oxidation were
calculated for the same irradiation time of 21 min
despite the fact that different extents of the reaction
data in Fig. 3a show that ~80% of initial dibutyl sulfide are achieved in the experiments at this time. Nevertheꢀ
was consumed during 20 min of irradiation at the maxꢀ less, the change in the selectivity for the products with
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170
ARSENTYEV et al.
(а)
Concentration, mmol/L
0.012
(b)
Concentration, mmol/L
0.012
0.0020
0.0015
0.0010
0.0030
0.0025
0.0020
0.0015
0.0010
0.0005
0
0.010
0.008
0.006
0.004
0.002
0.010
0.008
0.006
0.004
0.002
0.0005
0
0
10
20
30
40
0
5
10 15 20 25
Time, min
Time, min
(d)
(c)
Concentration, mmol/L
0.012
Concentration, mmol/L
C(Bu S)
0.0020
0.0020
0.0015
0.0010
0.0005
0
2
C(Bu SO)
0.014
0.012
0.010
0.008
0.006
0.004
0.002
2
C(Bu SO )
2
C(Bu S )
2
0.010
0.008
0.006
0.004
0.002
2
2
0.0015
C(butyraldehyde)
0.0010
0.0005
0
0
50
100
0
50
100
Time, min
Time, min
Fig. 3. Kinetics of concentration change of dibutyl sulfide and its partial oxidation products during photocatalytic oxidation at
2
radiant powers of (a) 43.9, (b) 10.5, (c) 3.6, and (d) 2.2 mW/cm .
the decrease in the radiation intensity is of interest in catalyst 2,4,6ꢀtriphenyl(thio)pyrylium, the electron
view of the linear character of the kinetic dependenꢀ transfer is the only reaction pathway and the formation
cies (Fig. 3). For example, the sulfone to sulfoxide of diethyl sulfoxide, ethanesulfonic acid, diethyl sulꢀ
selectivity ratio increases from 1 to 3.5, whereas the fide, diethyl thiosulfinate, and diethyl thiosulfonate is
selectivity for dibutyl disulfide only slightly changes to observed [35]. It was noted [36] that the oxidation of
be ~2%.
diethyl sulfide (DES) in the presence of С60 and С70
fullerenes in a toluene solution also resulted in preꢀ
dominant formation of sulfoxide. An admixture of
1,4ꢀdiazobycyclo[2.2.2]octane as a singlet oxygen
quencher completely suppressed the formation of sulꢀ
fone and sulfoxide, with 10–20% of DES being conꢀ
verted into unspecified products.
The photocatalytic oxidation of dibutyl sulfide was
investigated in the presence of 9,10ꢀdicyanoantracene
and benzophenone in acetonitrile and methanol [34].
The main reaction product was sulfoxide, whereas sulꢀ
fone and disulfide were byproducts. Lacombe et al.
[34] suggested that this process occurs via two parallel
routes, the formation of singlet oxygen and electron
In this study, the yield of sulfone was always higher
transfer from the sulfurꢀcontaining molecules to than the yield of sulfoxide. The disagreement with the
excited photosensitizer molecules. When diethyl sulꢀ published data can be due to the fact that the values
fide is oxidized in the presence of the cationic photoꢀ reported in the literature were obtained in experiments
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EFFECT OF IRRADIATION INTENSITY ON RATE AND SELECTIVITY
S radiant power
171
Bu S consumption rate, mol/(L min)
2
45
40
35
30
25
20
15
10
5
density selectivity Bu SO, %
2
0.00040
0.00035
0.00030
0.00025
0.00020
0.00015
0.00010
0.00005
S radiant power
density selectivity Bu SO , %
2
2
S radiant power
density selectivity Bu S , %
2
R
= 0.9999
2
2
Total yield for
S, %
0
2
43.9 10.5 3.6 2.2 Irradiation intensity, mW/cm
0
10
20
30
40
50
2
Irradiation intensity, mW/cm
Fig. 4. Dependence of the average rate of Bu S consumpꢀ
tion on irradiance of the reaction mixture during its phoꢀ
tocatalytic oxidation.
Fig. 5. Histogram of selectivity values for the formation of
2
Bu S oxidation products after 21 min of irradiation of the
2
reaction mixture at different radiation intensities.
Bu• + O2
…
C3H7CHO.
(10)
with the insufficiently pure solvent that contained
water. In this work, we used the extra pure, waterꢀfree
chemicals. The presence of polar solvents is known to
significantly increase the yield of sulfoxide, and this is
the case that the cited authors could observe because
of the presence of water in the solvents used.
Since the amount of the product butanal is an order
of magnitude above that of dibutyl sulfide, the formaꢀ
tion of other sulfurꢀcontaining products, such as
butanesulfonic acid and dibutyl thiosulfonate, is likely.
Based on the obtained data, we can conclude that
the reaction of photoinitiated oxidation of dibutyl sulꢀ
fide in the presence of С70 fullerene as the photosensiꢀ
tizer follows a complex mechanism comprising the
competing parallel steps of formation of the products
involving a common intermediate. Since the quantum
yield of singlet oxygen in the presence of С70 fullerene
can be close to unity, it may be assumed that the main
route of the reaction involving singlet oxygen includes
the following stages:
CONCLUSIONS
Photoinitiated oxidation of dibutyl sulfide in toluꢀ
ene solution in the presence of fullerene C70 occurs
under illumination with visible light to yield dibutyl
sulfoxide, dibutyl sulfone, dibutyl disulfide, and
butyraldehyde, with the selectivity of the process
depending on the intensity of light. Sulfurꢀcontaining
products undetectable by gas chromatography are also
formed, which amount up to 60 mol % of the reactant
dibutyl sulfide. The composition of the identifiable
products and published data indicate that the process
involves both energy transfer and electron transfer in
the primary photochemical reaction.
C
3O2 +
Bu2S + 1O2
Bu2S+OO–
Bu2S+OO– + Bu2S
hν
1O2,
(3)
(4)
(5)
(6)
70
Bu2S+OO–,
Bu2SO2,
ACKNOWLEDGEMENTS
2Bu2SO.
This work was supported by the Presidium of the
Russian Academy of Sciences, project no. 24.49, and
in part by the basic funding, project no. V.45.3.2, and
the Russian Foundation for Basic Research, project
nos. 13ꢀ08ꢀ01286 and 15ꢀ08ꢀ01936.
The formation of an intermediate persulfoxide,
dibutyl persulfoxide Bu2S+OO– in our case, as a result
of singlet oxygen binding to organic sulfides was
proven in [37]. The formation of dibutyl disulfide as a
product cannot occur with participation of singlet
oxygen, but this is possible as a result of the reactions
of electron transfer from Bu2S to the photoexcited
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Translated by L. Brovko
HIGH ENERGY CHEMISTRY
Vol. 49
No. 3
2015