Self-assembled ionic liquid based organosilica-titania: A novel and efficient catalyst for green epoxidation of alkenes

Article abstract of DOI:10.1016/j.jorganchem.2021.121787

A novel titanium-containing self-assembled ionic liquid based hybrid organic-inorganic organosilica (Ti-ILOS) was prepared, characterized and applied as highly effective catalyst for the green epoxidation of alkenes in the presence of hydrogen peroxide as

Full text of DOI:10.1016/j.jorganchem.2021.121787

Journal of Organometallic Chemistry 940 (2021) 121787
Contents lists available at ScienceDirect
Journal of Organometallic Chemistry
journal homepage: www.elsevier.com/locate/jorganchem
Self-assembled ionic liquid based organosilica-titania: A novel and
efficient catalyst for green epoxidation of alkenes
∗
Omolbanin Yari, Dawood Elhamifar , Masoumeh Shaker
Department of Chemistry, Yasouj University, Yasouj, 75918-74831, Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
A novel titanium-containing self-assembled ionic liquid based hybrid organic-inorganic organosilica (Ti-
ILOS) was prepared, characterized and applied as highly effective catalyst for the green epoxidation of
alkenes in the presence of hydrogen peroxide as oxidant. The Ti-ILOS catalyst was characterized using
FT-IR, SEM, XPS and EDX analyses. This catalyst was recovered and reused several times without signifi-
cant loss of performance. The leaching test was also performed to investigate the stability and nature of
designed catalyst under applied conditions.
Received 6 December 2020
Revised 5 March 2021
Accepted 15 March 2021
Available online 20 March 2021
Keywords:
Ionic liquid based organosilica-titania
Supported titanium catalyst
Alkene epoxidation
©
2021 Elsevier B.V. All rights reserved.
Recoverable catalyst
1. Introduction
diphenyl sulfide, [15] Ti−Fe O @MCM-41 for selective epoxida-
3
4
tion of olefins, [28] TMS-TS4 for cyclohexene oxidation reaction,
Since epoxides are key intermediates in the organic chemistry
and drug synthesis for production of fine chemicals, the epoxi-
dation of alkenes is a significant and attractive process between
chemists [1,2]. This process has been performed using many ho-
mogeneous and heterogeneous catalytic systems in the presence
of several oxidants such as hydrogen peroxide, in which the use
of heterogeneous catalysts is more interested in green chemistry
due to their easy recoverability, reusability and stability [3-7]. One
of effective and well-known catalysts is titanium based ones that
considered to be an environmentally friendly, excellent and inex-
pensive heterogeneous catalyst with good properties under most
conditions [8-11]. An effort to enhance these properties, expand
applications and grow catalytic activity of Ti-based catalysts, is
preparation of titanium containing composites [12-14]. One of the
most important composites is silica-titania materials that can be
prepared via both simultaneous hydrolysis and condensation of ti-
tanium and silicon precursors and also chemical attachment of
tetraaloxy titaniums onto silica materials [15-22]. Titanium species
have also been well incorporated in several mesoporous silicas
such as MCM-41, MCM-48 and SBAs via the grafting of titanium
precursors on the pore surface of these nanomaterials [23-27].
The Ti-containing materials have been applied as effective cata-
lyst in oxidation of several organic compounds. Some of recently
[18] Pd/SiO @Ti-MS for one-pot oxidation of methyl phenyl sul-
2
fide and diphenyl sulfide, [29] Ti-SBA-15 for selective oxidation of
aromatic sulfur compounds, [30] Au/TS-1@meso-SiO2 for selective
epoxidation of propylene, [31] PdAu@Ti-MHSS for one-pot oxida-
tion of methyl phenyl sulfide [32] and ILNOS-Ti for green oxidation
of alcohols [33].
Ionic liquids with unique properties such as low melting point,
high thermal and chemical stability, non-flammability, high electri-
cal conductivity, low vapor pressure and excellent solubility have
found many applications in the synthesis of organic compounds
as catalysts and solvents. Especially, the supported ionic liquids
simultaneously have the benefits of ionic liquids and recoverable
heterogeneous solids. Ionic liquids are often stabilized on solid sur-
faces through both chemical and physical methods. Among these,
organosilica materials containing ionic liquids have wide appli-
cations in adsorbents, chromatography, catalyst, electrochemistry,
solid phase extraction, sensor technology and gas storage due to
their unique properties such as high lipophilicity, thermal and me-
chanical stability. In particular, the incorporation/immobilization of
metals such as Cu, Pd, Au, Ni, Fe, Mn, and Ti in the framework of
ionic liquids led to the development of their applications in the
catalytic field [26,33-42].
Although significant studies have been reported on the use of
Ti-containing silica catalysts in oxidation processes, however, most
of these processes have been performed in the presence of toxic
organic solvents. In view of the above and in continuation of our
recent studies in the development of heterogeneous catalysts con-
taining ionic liquid, [26,33,35,43-45] herein, we have reported the
developed systems are Co-SiO @Ti-Si for the aerobic oxidation of
2
∗
CorrespondingAuthor.
E-mail address: d.elhamifar@yu.ac.ir (D. Elhamifar).
https://doi.org/10.1016/j.jorganchem.2021.121787
0
022-328X/© 2021 Elsevier B.V. All rights reserved.

O. Yari, D. Elhamifar and M. Shaker
Journal of Organometallic Chemistry 940 (2021) 121787
tBu
O
(
MeO) Si
N
N
Si(OMe)3
3
But O Ti O Bu
t
Cl
+
O
tBu
TEOS
Super dry MeOH
HCl (2M), H O
2
25 °C, 1 h, Ar
40 °C, 1 h
B
A
OH
Si
HO
Si
3
N
3
N
Cl
O
O
O
40 °C, 24 h
100 °C, 36 h
Si
Ti OH
O
A + B
Si
O
Ti
N
N
Si
3
3
O
Cl HO
Si OH
O
HO
O
Si
OH
N
N
Cl
Si
3
3
HO
Ti-ILOS
R1
R3
R2
R4
R1 O R2
R3 R4
Ti-ILOS
H O , solvent free, 70 °C
2
2
Scheme 1. Synthesis of Ti-ILOS and its catalytic application in the epoxidation of alkenes
synthesis of an organic-inorganic hybrid xerogel material in which
ionic liquids and titanium are dispersed very well in the silica
framework (Ti-ILOS, Scheme 1). In fact, our motivation in this
study is the design and preparation of a novel catalyst for green
oxidation of alcohols involving the advantages of both supported
ionic liquids and chemically immobilized catalysts. The Ti-ILOS was
characterized using FT-IR, EDX, SEM and XPS techniques.
2.2. General procedure for the epoxidation of alkenes using Ti-ILOS
catalyst
For this purpose, the Ti-ILOS catalyst (0.014 g) and alkene (1
mmol) were added into a reaction vessel. Then, H O2 (3 mL) was
2
added slowly and drop by drop during the reaction time. The re-
sulted mixture was stirred at 70°C and the reaction progress was
monitored by studying oxidized products at different times. The
oxidized products were analyzed by using a gas chromatograph
(
Agilent 6890N) equipped with SE-30 capillary column and a FID
2. Experimental section
detector. To ensure the reproducibility of the results, the experi-
ments were repeated under identical reaction conditions.
2
.1. Procedure for the preparation of Ti-ILOS
The titanium-containing self-assembled ionic liquid based hy-
2.3. Procedure for the recovery of the Ti-ILOS catalyst in the
epoxidation of alkenes
brid organic-inorganic organosilica (Ti-ILOS) was prepared through
simultaneous hydrolysis and condensation of propyl-imidazolium
ionic liquid, TBOT and TEOS by sol-gel method. The molar ratios of
the precursors were as follows: 6Si:1IL:3Ti. The sols were prepared
following this procedure: The IL (2 mmol) and TEOS (6 mmol)
For this, the epoxidation of styrene was selected as a test
model. The styrene (1 mmol) and catalyst (0.014 g) were added
in a reaction vessel and H O2 (3 mL) was added slowly and drop
2
were hydrolyzed for 1 h at 40°C in HCl (2 M, 30 mL) and H O
by drop during the reaction time. Then, this mixture was magneti-
cally stirred at 70°C under solvent free conditions and the reaction
progress was monitored using TLC and GC. After completion of the
reaction, the catalyst was collected and separated using centrifuge,
washed with EtOH and dried under vacuum. The recovered cata-
lyst was reused in the next run under the same conditions as the
first run. These steps were repeated several times and the results
showed that the catalyst could be recovered and reused at least
five times without significant decrease in efficiency.
2
(
20 mL) to give a mixture called A. The TBOT (3 mmol) was also
dissolved in super dry methanol while stirring for 1 h at 25°C un-
der Argon atmosphere to give a mixture called B. The A was added
to B and this mixture was firstly stirred for 24 h at 40°C and then
statically heated at 100°C for 36 h. The obtained solid material was
filtered and washed completely with deionized water and ethanol.
The final sample was dried at 70°C for 12 h and designated as Ti-
ILOS.
2

O. Yari, D. Elhamifar and M. Shaker
Journal of Organometallic Chemistry 940 (2021) 121787
Fig. 1. FT-IR spectrum of the Ti-ILOS catalyst
2
.4. Procedure for hot filtration test
This test was also performed on the epoxidation of styrene un-
der optimized conditions. For this, after about 45% of the reaction
was completed, it was stopped and the catalyst was separated us-
ing centrifuge. The catalyst-free residue was allowed to continue
under optimum conditions as above. After about 10 h, no notice-
able conversion was observed confirming no leaching of active ti-
tanium centers under applied media.
3. Results and discussion
3
.1. Characterization of Ti-ILOS
The FT-IR spectroscopy (Fig. 1) of the Ti-ILOS showed the C-Si
stretching vibrations at 700-800 cm 1. This analysis also showed
−
−
1
absorption bands at 946.8 cm
(for Si-O-Ti stretching), 1079,
1
185 and 962 cm 1 (for Si-O-Si stretching), 1384 cm
−
−1
(for C=C
Fig. 2. EDX analysis of the Ti-ILOS catalyst
−
1
−1
stretching) 1634 cm
(for C=N stretching), 2900-3000 cm
(for
−1
aliphatic C-H stretching), 3100 cm (for unsaturated C-H stretch-
ing) and 3300 cm−1 (for O-H stretching).
One at 458.5 eV, that is assigned to Ti (VI) ion in octahedral coor-
dination. Another peak at 460.0 eV corresponding to Ti (IV) ion in
tetrahedral coordination [31,46-49]. As shown in Fig. 4, only one
peak around 460.0 eV related to Ti 2p3/2 component in tetrahedral
coordination is seen for the Ti-ILOS catalyst.
The EDX analysis also showed the signals of Si, C, Cl, Ti, N and
O elements for the material (Fig. 2). The results of FT-IR and EDX
analyses confirmed the successful incorporation/immobilization of
ionic liquid, silica and titania moieties into/onto the material
framework.
The SEM image showed the presence of spherical particles with
an average size of about 80 nm for the material (Fig. 3).
The XPS spectrum showed two sharp peaks at 460.0 eV and
3.2. Catalytic activity of the Ti-ILOS
Due to epoxides are important intermediates in the chemical
industry and laboratory, in the next study, the catalytic efficiency
of Ti-ILOS was studied in the epoxidation of alkenes to give their
corresponding epoxides (Scheme 1). To obtain an optimized pro-
4
64.6 eV that are, respectively, attributed to Ti 2p3/2 and Ti 2p1/2
Fig. 4). It is well documented in the literature that the BE of the Ti
P3/2 in the titanosilicate materials is deconvoluted into two peaks.
(
2
3

O. Yari, D. Elhamifar and M. Shaker
Journal of Organometallic Chemistry 940 (2021) 121787
Fig. 5. Recyclability of Ti-ILOS catalyst
Fig. 3. SEM image of the Ti-ILOS catalyst
sult is delivered at 70 ºC (Table 1, entries 9-13). In the following,
the epoxidation of the model substrate was investigated in the ab-
sence of the Ti-ILOS in which no oxidation product was obtained
indicating the presence of the Ti-ILOS is required to perform the
reaction (Table 1, entry 12 versus entry 14). Also, it was found that
the reaction is not performed in the absence of oxidant (Table 1,
entry 12 versus entry 15). In the next, to show the exact role of Ti
species in the catalytic process, the activity of titanium-free ILOS
material was studied and the result was compared with that of Ti-
ILOS (Table 1, entry 12 versus entry 16). Interestingly, the Ti-free
ILOS delivered no epoxide product under the same conditions as
Ti-ILOS, confirming that the epoxidation process is completely cat-
alyzed by immobilized-Ti sites. Accordingly, the use of 0.014 g of
Ti-ILOS at 70 ºC and solvent-free media in the presence of H O
2
2
were chosen as optimal conditions.
To show the generality and substrate scope of designed catalytic
system, several alkenes were applied as substrate under optimal
conditions. The results showed that Ti-ILOS catalyst can epoxidize
styrene and α-methylstyrene efficiently and selectively. Also, cyclo-
hexene, cyclooctene, (Z)-stilbene and 1-octene were converted to
their corresponding epoxides with excellent selectivity by using Ti-
ILOS catalyst. It should be noted that the by-products synthesized
during the epoxidation of each substrate are shown in Table 2.
In the next study, the recyclability of the catalyst was inves-
tigated. For this, after reaction was completed in the epoxidation
of styrene as a test model, the catalyst was separated and washed
with EtOH. The recycled catalyst was used in the next reaction af-
ter being dried under vacuum. It was found that the Ti-ILOS cat-
alyst can be recovered and reused for at least five runs with no
significant decrease in its efficiency (Fig. 5).
Fig. 4. XPS spectrum in the Ti2p region of the Ti-ILOS catalyst
tocol for performing the aforementioned process, the oxidation of
styrene was selected as a reaction model and the effect of cat-
alyst loading, solvent, oxidant and temperature was investigated
(
Table 1). As can be seen, the investigations showed that increas-
ing the amount of catalyst has a significant effect on increasing
the product yield (Table 1, entries 1-4). As shown in the presence
of 0.005, 0.01, 0.014 and 0.02 g of the designed catalyst, respec-
tively, 15, 28, 35 and 35% yield of desired epoxide are obtained.
Therefore, the use of 0.014 g of catalyst was selected as optimum
catalyst loading for next studies. The effect of solvent study also
showed between water, THF, toluene, methanol and solvent-free
media, under solvent-free conditions the best result is delivered
Next, a leaching test was also performed to determine the true
nature of the catalyst under applied conditions. For this, after the
epoxidation was completed about 45%, the catalyst was separated
from reaction mixture and the catalyst-free residue was allowed to
continue under optimal condition. This showed no further progress
in the epoxidation process indicating the high stability and no
leaching of active titanium centers under applied media.
(
Table 1, entry 3 versus entries 5-8). Importantly, between several
oxidants in hand, molecular oxygen and hydrogen peroxide were
used due to their low cost, environmentally-friendly and also pro-
duce water as the sole by-product. The study showed that the
Finally, the efficiency of Ti-ILOS was compared with some of the
catalysts used recently in the epoxidation of alkenes. According to
Table 3, our catalyst is better than and/or comparable with former
catalysts in terms of reaction conditions and recycling times. The
high efficiency of our designed catalyst is attributed to the valu-
H O oxidant compared to oxygen is more effective in the epox-
2
2
idation process (Table 1, entry 8 versus entry 9). It was also found
that the reaction temperature considerably impresses the reaction
rate. As shown, between 25, 40, 60, 70 and 80 ºC, the best re-
4

O. Yari, D. Elhamifar and M. Shaker
Journal of Organometallic Chemistry 940 (2021) 121787
Table 1
The effect of solvent, temperature, oxidant and catalyst loading in the epoxidation of styrene
Entry
Catalyst (g)
Oxidant
Solvent
Temperature (°C)
Time (h)
Yield (%) a
1
2
3
4
5
6
7
8
9
0.005
0.010
0.014
0.020
0.014
0.014
0.014
0.014
0.014
0.014
0.014
0.014
0.014
—
O2
Water
60
60
60
60
60
60
60
60
60
25
40
70
80
70
70
70
12
12
12
12
12
12
12
12
3
15
28
35
35
—
O2
Water
O2
Water
O2
Water
O2
Toluene
O2
THF
—
O2
Methanol
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
18
38
76
20
55
95
92
—
O2
H2O2
H2O2
H2O2
H2O2
H2O2
H2O2
—
1
1
1
1
1
1
1
0
3
1
3
2
3
2
2
4
12
12
12
5
6b
0.014
0.014
—
H2O2
—
a
GC yields. b ILOS was used as catalyst.
Table 2
Epoxidation of alkenes using Ti-ILOSa
Table 3
The comparison study between efficiency of the present catalyst with that of former catalysts
Catalyst
MoCT
Conditions
Oxidant
Time (h)
Recovery times
Ref.
5
Cat. 100 mg, dichloroethane, 80 ºC
Cat. 0.1 g, 1,2-dichloroethane, 70 ºC
Cat. 0.1 g, toluene, 80 ºC
Cat. 10 mg, DMF, 100 ºC
Cat. 0.2 g, decane, 368 ºK
Cat. 0.4 g, CH3CN, 338 ºK
Cat. 50 mg, decane, 333 ºK
Cat. 150 mg, TFT, 363 ºK
t-BuOOH
t-BuOOH
t-BuOOH
Air
10
6
5
5
8
4
2
5
2
4
5
[50]
PTA/Si–imid@ Si–MNPs
Ti−Fe3O4@MCM-41
Co-250
[51]
6
[28]
4
[52]
Ti-SBA-15
t-BuOOH
H2O2
5
[53]
Ti–SiO2
3
[54]
6
0Si/Ti-MCM-41
t-BuOOH
t-BuOOH
H2O2
5
[55]
Ti/S9460iO2-Dav
Ti-ILOS
24
2
[56]
Cat. 0.014 g, Solvent free, 70 ºC
This work
5

O. Yari, D. Elhamifar and M. Shaker
Journal of Organometallic Chemistry 940 (2021) 121787
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Declaration of Competing Interest
[
30] T.W. Kim, M.J. Kim, F. Kleitz, M.M. Nair, R. Guillet-Nicolas, K.E. Jeong, H.J. Chae,
C.U. Kim, S.Y. Jeong, ChemCatChem 4 (2012) 687.
The authors declare that they have no known competing finan-
cial interests or personal relationships that could have appeared to
influence the work reported in this paper
[
31] L. Xu, Y. Ren, H. Wu, Y. Liu, Z. Wang, Y. Zhang, J. Xu, H. Peng, P. Wu, J. Mater.
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The authors thank Yasouj University and the Iran National Sci-
ence Foundation (INSF) for supporting this work.
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