The Synergy Effect in Tio2 Supported Bi-Mo Catalysts for Facile and Environmentally-Friendly Synthesis of Pyridylaldehydes from Oxidation of Picolines

Article abstract of DOI:10.1134/S0965544120020061

Abstract: The oxidation of picolines to pyridlaldehydes was studied over bismuth molybdate catalysts supported on TiO₂. The research results showed that α-Bi₂Mo₃O₁₂ was superior to β-Bi₂Mo₂O₉ and γ-Bi₂MoO₆ in terms of reactivity. Further doping MoO₃ to α-Bi₂Mo₃O₁₂/TiO₂ gave rise to increased catalytic performance, which was due to the synergy effect of α-Bi₂Mo₃O₁₂ and MoO₃. The effect was on one hand manifested in the intimate relationship between α-Bi₂Mo₃O₁₂ and MoO₃ in stabilizing the crystallographic structure of catalysts and thereafter maintaining the surface area of the catalyst, as indicated by the BET surface area and XRD analysis. Moreover, NH₃-TPD analysis demonstrated the effect in modifying the surface acidity of the catalysts, and thus facilitating the substrate adsorption as the picolines are alkaline substances. Additionally, the effect between α-Bi₂Mo₃O₁₂ and MoO₃ rendered the modification of the electronic properties and thereafter the oxygen desorption properties and reducible properties of the catalysts, as evidenced in the H₂-TPR and O₂-TPD analysis.

Full text of DOI:10.1134/S0965544120020061

ISSN 0965-5441, Petroleum Chemistry, 2020, Vol. 60, No. 2, pp. 181–186. © Pleiades Publishing, Ltd., 2020.
Published in Russian in Neftekhimiya, 2020, Vol. 60, No. 2, pp. 199–205.
The Synergy Effect in TiO Supported Bi-Mo Catalysts for Facile
2
and Environmentally-Friendly Synthesis of Pyridylaldehydes
from Oxidation of Picolines
a, c,
b
c,
Jie Yu *, Viachaslau Zhylko , and Liyan Dai **
a
College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou, 310015 China
b
Faculty of Environmental Monitoring of International Sakharov Environment Institute of Belarusian State University,
Minsk, 220070 Republic of Belarus
c
College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027 China
*e-mail: yj313513@sina.com
**e-mail: dailiyan@zju.edu.cn
Received April 5, 2019; revised May 23, 2019; accepted October 14, 2019
Abstract—The oxidation of picolines to pyridlaldehydes was studied over bismuth molybdate catalysts sup-
ported on TiO . The research results showed that α-Bi Mo O was superior to β-Bi Mo O and γ-Bi MoO
2
2
2
3
3
12
12
12
2
2
9
2
6
in terms of reactivity. Further doping MoO to α-Bi Mo O /TiO gave rise to increased catalytic perfor-
3
2
mance, which was due to the synergy effect of α-Bi Mo O and MoO . The effect was on one hand mani-
2
3
3
fested in the intimate relationship between α-Bi Mo O and MoO in stabilizing the crystallographic struc-
2
3
12
3
ture of catalysts and thereafter maintaining the surface area of the catalyst, as indicated by the BET surface
area and XRD analysis. Moreover, NH -TPD analysis demonstrated the effect in modifying the surface acid-
3
ity of the catalysts, and thus facilitating the substrate adsorption as the picolines are alkaline substances. Addi-
tionally, the effect between α-Bi Mo O and MoO rendered the modification of the electronic properties
2
3
12
3
and thereafter the oxygen desorption properties and reducible properties of the catalysts, as evidenced in the
H -TPR and O -TPD analysis.
2
2
Keywords: picoline, pyridylaldehyde, oxidation, bismuth molybdate, synergy
DOI: 10.1134/S0965544120020061
INTRODUCTION
Generally, the synergetic effect of two metal active
components may result in a surprising catalytic activ-
Pyridylaldehydes as synthetic intermediates are of ity in oxidation reactions, such as Cu-Ce [11], Fe-V
paramount significance in chemistry because of their [12] and Bi-Mo [13]. The Bi-Mo system is well-
widespread application in the fields of pharmaceuti- known owing to its good catalytic performance in
cals, agrochemicals, chiral catalysts, functional poly- hydrocarbon oxidative reactions since 1960s [14–16],
especially propylene oxidation to acrolein [17] that has
been industrialized successfully, and researches of this
system are ongoing in discovering new properties and
applications [18–20]. Till now, research work con-
cerning the oxidation of picolines to pyrdiylaldehydes
over this system has been rarely reported, we envi-
sioned that the Bi-Mo catalyst could be an effective
candidate in the oxidation of picolines in that they
have similar unsaturated structures and active hydro-
gen atoms with propylene. Our previous study [21] by
using 2-picoline as probe molecular showed that α-
mers and as well as others [1–5]. Therefore, intensive
study for their preparation turns out to be meaningful.
Molecular oxygen as a green oxidant is preferably
involved in oxidative processes [6] since it is environ-
mentally benign, especially for bulk chemical indus-
tries. Meanwhile, water as a nontoxic, economical and
environmentally friendly medium is of widespread
interest in organic synthesis [7]. Based on these, it is
extremely desirable to achieve the green synthesis of
pyridylaldehydes from picolines via heterogeneous
catalysis employing oxygen as terminal oxidant and Bi Mo O and MoO supported onto titania in coop-
2
3
12
3
water as reaction medium. As for the catalysts erative catalysis gave outstanding performances better
reported, vanadia based catalysts [8–10] were the than that of V O and MoO also supported onto tita-
2
5
3
most commonly used, however, the yield was relatively nia [22]. However, the reasons accounting for the
low and dissatisfying. Thus, to develop an effective cooperative catalysis between α-Bi Mo O and MoO
3
2
3
12
and highly efficient catalyst is still a challenge.
haven’t been understood well yet.
81
1

1
82
JIE YU et al.
Therefore, in the present work, the synergy effect reached the set point and stabilized, oxygen regulated
between α-Bi Mo O and MoO was uncovered. by a flowmeter was fed in for one hour, then deionized
2
3
12
3
Besides, by taking into consideration process integrity, water was introduced into the system using a pulseless
the catalytic behaviors of three phases of bismuth pump for one hour, after that, the picoline in water was
molybdates as well as the performances of titania sup- used in place of pure water. Crude products were col-
ported α-Bi Mo O and MoO catalysts in oxidation lected and analyzed using an Agilent 6820 GC instru-
2
3
12
3
ment. The conversion of picolines and the selectivity
to pyridylaldehydes were calculated based on their
peak areas in gas chromatograph (external standard
method).
reactions of picolines were also investigated in detail.
EXPERIMENTAL
Catalyst Preparation. Catalysts were prepared
using the co-precipitation method. Commercially
available chemical reagents were used without any fur-
RESULTS AND DISCUSSION
ther purification. (NH ) Mo O · 4H O was dissolved
4
6
7
24
2
Our initial efforts then focused on screening of
in deionized water and heated to 70°C with stirring,
then a solution of 1M Bi(NO ) · 5H O in 2M HNO
three bismuth molybdates, namely, Bi Mo O (α),
2
3
12
3
3
2
3
Bi Mo O (β), and Bi MoO (γ), by using 2-picoline
2 2 9 2 6
was dropwise added. Subsequently, a certain amount
as the probe molecule. Catalytic test results were sum-
marized in Table 1. As shown, all the three phases can
be readily prepared at 600°C (Entry 1–3 and 6–8),
while at 550°C (Entry 5 and 10), the β phase was
unstable, and thus decomposed into α and γ phases
of TiO (anatase) was added, the resulting slurry was
2
stirred for 3 h and water was removed by a rotary evap-
orator, the residue was then extruded with the size of
2
mm in diameter and 2.5 mm in length, dried at 80°C
for 2 h, and calcined at 550°C for 10 h.
[
23], irrespective of whether loaded into titania or not.
Catalyst Characterization. The BET surface areas It is obvious that catalysts with pure α or β phase
were determined by nitrogen adsorption at 77K exhibited similar reactivity, both better than that of the
employing a Micromeritics TriStar II 3020 instru- γ phase (e.g. Entry 6, 7 to Entry 8), and the existence
ment.
of the γ phase in the catalyst caused a decline in con-
version of 2-picoline and selectivity to 2-pyridylalde-
hyde (Entry 5 and 10). In addition, for α and β phases,
the conversion nearly doubled when supported on
titania, while the selectivity only slightly changed with
a difference not exceeding 7%, exemplified in the case
of MB32/550 (α, conv. 15.5%, sel. 87.3%) and
MB32T550 (α, conv. 29.5%, sel. 81.3%).
X-ray diffraction (XRD) patterns were collected on
a Rigaku D/max-2550pc diffractometer using Cu Kα
radiation (40 kV, 250 mA) at diffraction angles (2θ)
from 20° to 90°.
Temperature-programmed desorption of ammonia
(
NH -TPD) was determined by a PX200 adsorption
3
instrument. The sample (100 mg) was pretreated at
5
00°C for 1 h in helium atmosphere, cooled to 40°C,
Based on the above, the α phase supported on tita-
filled with 4% NH /He mixed gas for half an hour, and nia (MB32T550) was subsequently used for further
3
–1
research on account of its stability as well as the supe-
rior catalytic performance over others. The reaction
temperature was an important parameter in terms of
the reactivity. With other conditions remaining
unchanged as in Table 1, when the reaction was car-
ried out at 290°C, an increase of the conversion to
then switched to pure helium (30 mL min ) for 1 h to
remove weakly adsorbed ammonia, and finally heated
–1
–1
to 500°C at 10°C min in pure He (30 mL min ).
Temperature-programmed reduction (TPR) was
carried out on a Micromeritics AutoChem II 2920
instrument, and the samples of the catalyst (100 mg)
were crushed into 60 meshes and preheated under
argon atmosphere at 400°C for 1 h, then cooled down
4
7
5.2% followed by a decrease of the selectivity to
0.3% was observed, further increasing the tempera-
ture to 310°C provided an improvement of the conver-
sion to 57.2% but also led to a downturn of the selec-
to 80°C and reduced with a 10% H /Ar mixed gas
2
–1
(
1
30 mL min ) from 80 to 800°C at a heating rate of
tivity to 61.0%. In terms of atom economy and as well
–
1
5°C min .
as product yield, a temperature of 290°C was assumed
Temperature-programmed desorption of oxygen as a reasonable and expedient value for follow-up
(
O -TPD) was performed with a GC1690 instrument, experiments.
2
and the samples of the catalyst (100 mg) were treated
In the previous research, in order to pursue
better catalytic performance, we had found
–1
with a 5% O /Ar mixed gas (30 mL min ) at 300°C for
2
1
2
h, then cooled down to 50°C, and heated to 900°C at that by introducing an extra amount of MoO into the
3
–1 –1
0°C min in pure He (40 mL min ).
Catalytic Tests. The catalytic tests were carried out cantly improved. Therefore, five catalyst samples were
in a fixed-bed stainless tube reactor with 10 mm ID of prepared (Table 2) and catalytic tests were carried out
α-Bi Mo O /TiO catalyst, the reactivity was signifi-
2 3 12 2
6
00 mm length under atmospheric pressure. The tem- accordingly (Table 3) [21]. It was shown that the con-
perature in the catalyst zone was kept constant and version for MB32T and MT each with only one active
measured using a thermocouple, after the temperature component was much lower than that for the other
PETROLEUM CHEMISTRY
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THE SYNERGY EFFECT IN TiO SUPPORTED Bi-Mo CATALYSTS
183
2
Table 1. Bi-Mo catalysts screening for oxidation of 2-picolinea
Conversion
of 2-picoline, %
Selectivity to
2-pyridylaldehyde, %
Catalystsb
Entry
Active phase
1
2
3
MB32/600
MB11/600
α
β
γ
8.6
9.9
N.a.
94.1
93.2
N.a.
MB12/600c
MB32/550
MB11/550
MB32T600
MB11T600
MB12T600
MB32T550
MB11T550
MB12T550
4
5
6
7
8
9
α
15.5
12.2
17.7
19.1
13.1
29.5
19.7
87.3
78.5
87.2
86.6
63.5
81.3
68.1
52.1
α and γ
α
β
γ
α
1
0
α, β, and γ
11
γ
16.0
a
b
–1
–1
Reaction conditions: 4 g catalyst, 270°C, flow rate of 10% 2-picoline aqueous solution 0.5 mL min , oxygen flow rate 0.1 L min
.
Catalysts MBxy/z were unsupported and MBxyTz were those loaded into TiO , M = Mo, B = Bi, xy = molar ratio of Mo/Bi, and z =
2
calcination temperature.
c
Catalyst inapplicable for activity test due to its poor mechanical strength.
a
Table 2. Detailed information of various Bi-Mo catalysts supported on TiO
2
Catalysts composition
Hydrogenconsumption
2
–1
Catalyst
Surface area, m g
α phase/MoO3,
in TPR, mmol g−1
MoO content, %
3
cat
mol/mol
MT
0 : 1
∞
1 : 1
2 : 1
5 : 1
15
0
2.1
1.1
0.5
4.1
3.1
4.0
4.0
3.9
1.56
1.77
1.96
1.98
1.96
MB32T
MB21T
MB74T
MB85T
a
Catalysts MBxyT were with 15% load amount supported on TiO and calcined at 550°C, M = Mo, B = Bi, xy = molar ratio of Mo/Bi.
2
three catalysts with two active components, and the Table 3. Influence of various Bi-Mo catalysts on oxidation
a
of 2-picoline
similar trend for the selectivity. Moreover, catalyst
MB21T with a 1/1 molar ratio of α-Bi Mo O /MoO
2
3
12
3
Selectivity
to 2-pyridylaldehyde,
%
Conversion
of 2-picoline, %
gave the best performance. By these, it might be con-
Entry Catalysts
sidered the outstanding performance of MoO doped
3
α-Bi Mo O /TiO catalysts was owing to the synergy
2
3
12
2
1
2
3
4
5
MT
51.8
45.2
70.9
63.6
61.0
78.1
70.3
83.1
80.3
81.7
effect between α-Bi Mo O and MoO .
2
3
12
3
MB32T
MB21T
MB74T
MB85T
To interpret this synergy effect, BET analysis
Table 2) and XRD analysis (Fig. 1) were carried out
(
in the first place. In some sense, the much lower reac-
tivity of MB32T can be perceived partly in terms of its
2
–1
reduced BET surface area (3.0 m g ) by about 25%
a
Reaction conditions: 4 g catalyst, 290°C, flow rate of 10% 2-pico-
2
–1
line aqueous solution 0.5 mL min– , oxygen flow rate 0.1 L min .
1
–1
compared with others (4.0 m g or so), which may as
a result generate much less active sites. It can be seen
in Fig. 2 that catalyst MT bears MoO and anatase
3
MoO , whereas MoO in the Bi-containing catalysts
TiO , and the other four Bi-containing samples con-
3
3
2
sist of α-Bi Mo O and anatase TiO . According to was not detected by XRD analysis because its quantity
2
3
12
2
the literature [23], catalysts with Bi/Mo molar ratios was too small, but it was observed by SEM analysis
lower than 2/3 consisted of both α-Bi Mo O and [21]. At the same time, the analysis shows that rutile
2
3
12
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84
JIE YU et al.
4
0
0
a
MT
a
MT
a
a
a
a
MB21T
MB74T
MB85T
MB32T
b
b
b
a
a
b
3
a*
a
MB32T
c
a
a
a
a
a
a
a
c
c
a
a
a
a
a
a
c
c
c
c
20
c
a
a
a
MB21T
c
a
a
c
c
c
c
a
a
10
MB74T
a
c
c
c
c
a
0
MB85T
a
a
c
c
c
a
a
0
100
200
Temperature, °С
300
400
500
10
20
30
40
50
θ, deg
60
70
80
2
Fig. 2. NH -TPD analysis of the catalysts.
3
Fig. 1. XRD analysis of MT, MB32T, MB21T, MB74T
and MB85T, (a) anatase TiO , (a*) rutile TiO , (b) MoO
2
2
3
and the relative reactivity of α-Bi Mo O was much
2 3 12
and (c) α-Bi Mo O .
2
3 12
better than that of MoO as MoO had no α-hydrogen
3
3
abstracting sites [28]. Based on the explanation above,
the formation of a picolinic intermediate via α-hydro-
gen abstraction during the oxidation of 2-picoline to
TiO , which was not found in the other three Bi-con-
2
taining samples, had comparable intensity with ana-
2-pyridylaldehyde was proposed. However, in the case
tase TiO in MB32T. On the other hand, Bond G. C.
2
of oxidation of 2-picoline to 2-pyridylaldehyde, the
fact that the reactivity of MT was better than that of
reported that anatase wouldn’t transform into rutile
TiO lower than 600°C in pure samples [24], so the co-
2
MB32T proves MoO does have α-hydrogen abstract-
3
existence of anatase and rutile TiO in MB32T cal-
2
ing sites. A plausible explanation for this is that pico-
line is an alkaline substance, so that the acidity of the
catalyst is favourable for its adsorption and the interac-
tion with the catalysts accordingly, and thereafter pos-
cined at 550°C implies that α-Bi Mo O facilitated
2
3
12
the transformation from anatase to rutile, which
reduced the surface area of the catalyst by 25% com-
pared with others as shown in Table 2, but this trans-
sibly α-hydrogen abstraction. NH -TPD was per-
3
formation effect was inhibited by MoO as there was
3
formed to determine the acidity of the catalysts, as
shown in Fig. 2. It is seen that week acidic sites existed
in all samples. Integration of the desorption peaks
no formation of rutile in the other three Bi-containing
catalysts with excess MoO . It may be concluded that
3
the existence of Mo retarded the association between showed the surface acidic sites density followed the
α-Bi Mo O and TiO , thus delaying the change of order of MB21T > MT > MB74T > MB85T >
2
3
12
2
crystallographic structure of TiO . In other words, this MB32T, implying that the surface acidity of those cat-
2
synergy effect was on one hand interpreted by the alysts containing α-Bi
Mo
O
12 increased with the
2
3
active components in stabilizing the crystallographic addition amount of MoO . Moreover, the slightly
3
structure of catalysts and thereafter maintaining the higher density of MB21T than that of MT demon-
surface area.
strates the synergy effect of α-Bi Mo O and MoO in
2 3 12 3
modifying the surface acidity of the catalysts.
Oxidation reactions of hydrocarbons in heteroge-
Additionally, α-hydrogen abstraction of picolines
was easy to take place because the picolinic intermedi-
ate should be much more easily and steadily formed
than the allyl intermediate in that the electron of the
picolinic radical is delocalized by a conjugated hetero-
cycle after α-hydrogen abstraction while that of the
allyl radical is delocalized merely by a double bond.
Moreover, the N atom at which the converging of the
electrons takes place due to its strong negativity may
further stabilize the picolinic radical.
neous catalysis is a process that follows Mars-van
Krevelen mechanism [25, 26] which includes many
steps: (1) chemisorption of hydrocarbon on the sur-
face of the catalyst and abstraction of an α-hydrogen
to form an intermediate; (2) insertion of lattice oxygen
into the intermediate to form product; and (3) replen-
ishment of lattice oxygen removed from the surface of
the catalyst during the second step in order to recon-
stitute the active site. The generally accepted approach
for propylene oxidation is proceeded through the for-
mation of an allyl intermediate by α-hydrogen
Literature shows that lattice oxygen mobility plays
abstraction [27]. Bi was considered the α-hydrogen a key role in determining the reactivity of the bismuth
abstraction center to generate allyl species, while Mo molybdate catalysts [29], and addition of a small
was the chemisorption and oxygen insertion center, amount of conductive metal oxide can promote the
PETROLEUM CHEMISTRY
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2020

THE SYNERGY EFFECT IN TiO SUPPORTED Bi-Mo CATALYSTS
185
2
This was an indication that the α-Bi Mo O and
2
3
12
MB85T
MB74T
MoO cooperated in synergy and enhanced the lattice
3
oxygen mobility of the catalyst.
The synergy effect can be due to either the forma-
tion of a new phase or the “remote control mecha-
nism” where there is no generation of new phases [32].
Since the XRD analysis gave no indication of forma-
tion of a new phase, the increase in the intrinsic reac-
MB21T
MB32T
tivity of MoO doped α-Bi Mo O /TiO catalysts can
3
2
3
12
2
be interpreted in terms of the “remote control mecha-
nism” in which activated “spillover oxygen” by a
“
donor phase” migrates to an “acceptor phase” where
MT
new active catalytic sites are created [33]. Previous
research revealed that Bi facilitates the dissociation of
gaseous oxygen into lattice oxygen and its subsequent
diffusion into the active sites [34]. The mobility of lat-
200
400
600
800
Temperature, °С
tice oxygen in MoO is very high [35], thus the lattice
3
Fig. 3. O -TPD analysis of the catalysts.
oxygen facilitated by α-Bi Mo O should be able to
2
2
3
12
easily diffuse into MoO where new active catalytic
3
sites are created, resulting in increased reactivity. It
can be inferred that the intimate relationship between
α-Bi Mo O and MoO led to the modification of the
electronic properties and thereafter the oxygen
desorption properties and reducible properties of the
catalysts, giving rise to its increased catalytic perfor-
mance.
transfer of the lattice oxygen in the bismuth molybdate
catalysts [30], and hence the improvement of the reac-
2
3
12
3
tivity of the catalysts accordingly. MoO is a conduc-
3
tive metal oxide [31] in this case, though the connec-
tion between conductivity and catalytic activity was
not the objective of the present research.
Catalyst MB21T was also used for catalytic test for
the other two isomers of picoline, and as it was shown
in Table 4, the catalyst was also effective when used in
In H -TPR analysis (Table 2), the fact that the
2
hydrogen consumption amount of MB21T, MB74T,
MB85T were almost the same and higher than that of
MT and MB32T implied that α-Bi Mo O and MoO
4-picoline oxidation. Nevertheless, the low conver-
2
3
12
3
sion of 3-picoline with access use of catalyst amount
was mainly because the methyl at meta-position of N
would have higher electron density than that at ortho-
and para-positions, which was unfavorable for depro-
tonation of the methyl.
in synergy could enhance the lattice oxygen mobility
of the catalyst and thus its reducibility, which was fur-
ther evidenced in the O -TPD analysis results, as
2
shown in Fig. 3. There was one apparent desorption
peak at around 500°C with a shoulder and a weak
desorption peak at around 800°C for MT, two weak
broad desorption peaks at around 500 and 750°C for
MB32T, and one apparent desorption peak at around
CONCLUSIONS
In the present work, oxidation of picolines to pyr-
5
00°C with a shoulder and one apparent desorption
idylaldehydes over TiO supported bismuth molybdate
2
peak at around 850°C all for MB21T, MB74T, and
MB85T. It is also seen that the overall intensities of the
desorption peaks for MB21T, MB74T and MB85T
were stronger than that of MB32T and MT, and
among which, the one for MB21T was the strongest.
catalysts was studied. The research results showed that
α-Bi Mo O was superior to β-Bi Mo O and
2
3
12
2
2
9
γ-Bi MoO in terms of reactivity. Further doping
2
6
MoO to α-Bi Mo O /TiO gave rise to increased
3
2
3
12
2
catalytic performance, which was due to the synergy
effect of α-Bi Mo O and MoO . Catalyst with 1 : 1
2
3
12
3
Table 4. Oxidation of picolines over the catalyst MB21Ta
molar ratio of α-Bi Mo O and MoO gave the best
2 3 12 3
performance. 2-picoline and 4-picoline could be
readily oxidized to 2-pyridylaldehyde and 4-pyridylal-
dehyde, respectively. The much lower conversion of
Selectivity
to pyridylaldehyde,
%
Conversion
of picoline, %
Entry Substrate
3-picoline was mainly because the methyl at meta-
position of N would have higher electron density than
that at ortho- and para-positions, which was unfavor-
able for deprotonation of the methyl. Further research
on the Bi-Mo catalyst system as well as catalyst adapt-
ability to a variety of picoline derivatives and other
related substrates is now being carried out in our labo-
ratories.
1
2
2-Picoline
-Picolineb
4-Picoline
70.9
18.9
83.1
93.7
3
3
73.1
80.3
a
b
Reaction conditions: 4 g catalyst, 290°C, flow rate of 10% picoline
aqueous solution 0.5 mL min , oxygen flow rate 0.1 L min
6 g catalyst.
–1
–1
.
1
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JIE YU et al.
FUNDING
This work was supported by the Provincial Intelligence
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PETROLEUM CHEMISTRY
Vol. 60
No. 2
2020