Solvent-free selective oxidation of alcohols with tert-butyl hydroperoxide catalyzed by palladium(II) isatin Schiff base complex supported into three-dimensional mesoporous silica KIT-6

Article abstract of DOI:10.1007/s11164-020-04319-0

In this work, the catalytic activity of a palladium(II) isatin Schiff base complex immobilized into mesoporous silica KIT-6 (Pd-isatin Schiff base@KIT-6) was studied for the oxidation of different alcohols with tert-butyl hydroperoxide (TBHP, 70% aqueous solution) as an oxidant under solvent-free conditions. To find the suitable reaction conditions, the effect of essential factors including the solvent, temperature, catalyst amount and kind of oxidant on the oxidation of benzyl alcohol was explored. The results showed that in this catalytic system, the corresponding aldehydes and ketones were obtained with high to excellent yields at 50?°C without the formation of carboxylic acids as by-products. The catalyst was easily recovered by simple filtration and reused in five subsequent reaction cycles without any significant loss in the catalytic activity. Moreover, the comparison of the Fourier transform infrared (FT-IR) spectrum, X-ray diffraction (XRD) pattern, scanning and transmission electron microscopy (SEM and TEM) images of the used catalyst with a fresh one showed that the structure of the Pd-isatin Schiff base@KIT-6 catalyst remained intact after five times of reuse.

Full text of DOI:10.1007/s11164-020-04319-0

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-020-04319-0
Solvent‑free selective oxidation of alcohols with tert‑butyl
hydroperoxide catalyzed by palladium(II) isatin Schif base
complex supported into three‑dimensional mesoporous
silica KIT‑6
Davoud Mousavi1 · Mehdi Hatef Ardakani1 · Samira Saeednia1 ·
Mohammad Sabet1
Received: 1 June 2020 / Accepted: 31 October 2020
© Springer Nature B.V. 2020
Abstract
In this work, the catalytic activity of a palladium(II) isatin Schif base complex
immobilized into mesoporous silica KIT-6 (Pd-isatin Schif base@KIT-6) was stud-
ied for the oxidation of diferent alcohols with tert-butyl hydroperoxide (TBHP, 70%
aqueous solution) as an oxidant under solvent-free conditions. To fnd the suitable
reaction conditions, the efect of essential factors including the solvent, tempera-
ture, catalyst amount and kind of oxidant on the oxidation of benzyl alcohol was
explored. The results showed that in this catalytic system, the corresponding alde-
hydes and ketones were obtained with high to excellent yields at 50 °C without the
formation of carboxylic acids as by-products. The catalyst was easily recovered by
simple fltration and reused in fve subsequent reaction cycles without any signif-
cant loss in the catalytic activity. Moreover, the comparison of the Fourier transform
infrared (FT-IR) spectrum, X-ray difraction (XRD) pattern, scanning and transmis-
sion electron microscopy (SEM and TEM) images of the used catalyst with a fresh
one showed that the structure of the Pd-isatin Schif base@KIT-6 catalyst remained
intact after fve times of reuse.
Keywords Palladium · Isatin · Schif base · KIT-6 · Alcohol oxidation · Solvent-free
* Mehdi Hatef Ardakani
m.hatef@vru.ac.ir; m_hatef_chem@yahoo.com
1
Department of Chemistry, Faculty of Science, Vali-E-Asr University of Rafsanjan,
Rafsanjan 77188-97111, Iran
Vol.:(0123456789)
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D. Mousavi et al.
Introduction
The products of the oxidation of alcohols like aldehydes and ketones are widely
used for organic synthesis of fne chemicals in laboratories and chemical indus-
tries [1]. Aldehydes and ketones exist in many biologically active molecules and
functional intermediates for the pharmaceuticals, agricultural chemicals, drugs
and fne chemicals [2–4]. The most common procedures for the oxidation of alco-
hols may use some toxic, unsafe, unstable and expensive reagents such as per-
sulfate and chromate which are not environmentally friendly and economically
justifed [5, 6]. Therefore, the development of environmentally friendly catalytic
systems for the oxidation of alcohols with high activity and selectivity has been
considered by researchers. Recently, Guðmundsson et al. reported the frst Fe(II)
catalyzed biomimetic aerobic oxidation of alcohols along with an electron-rich
quinone and an oxygen-activating Co(salen)-type complex as electron transfer
mediators (ETMs). These electron transfer mediators are part of what is called
the electron transport chain (ETC), where O2 is typically used as the terminal oxi-
dant and lead to a low energy pathway via stepwise electron transfer [7].
Azomethines or Schif base ligands have played the main role in developing
the transition metal coordination chemistry due to their facile synthesis, versa-
tility, chemical and thermal stabilities [8]. In recent years, special attention has
been paid to the transition metal Schif base complexes owing to their outstand-
ing structural features, catalytic applications, biological roles in biochemical pro-
cesses and designing of chemosensors [9–11]. Schif base transition metal com-
plexes are also interesting oxidation catalysts because of their ease of preparation,
low cost, chemical and thermal stabilities, along with their selective performance
[12]. Recently, Reddy et al. reported new copper Schif base complexes based
pyrene and anthracene with high fuorescence property for the very fast detec-
tion of pyric acid (PA) at diferent pH ranges [13, 14]. They also designed a new
Schif base ligand by condensation of 1,3-diaminopropane with anthracene-9-car-
boxaldehyde, which gave a nickel complex as an efcient fuorescence chemosen-
sor for the selective detection of 2,4,6-trinitrophenol (TNP) [15]. TNP is released
into the environment as industrial wastage and is one of the main reasons for the
pollution. It creates health hazards and chronic, skin and eye diseases and is used
as a powerful explosive similar to TNT [16].
In catalysis science, the separation and recycling of catalysts are one of the
important issue. For this purpose, the homogeneous catalysts are usually sup-
ported on organic substrates such as polystyrene and polyethylene glycol or inor-
ganic supports like clay, carbon nanotubes and silica mesoporous materials [17].
The mesoporous silica KIT-6 has an Ia3d cubic structure with high thermal sta-
bility, high surface area and large pore size [18]. KIT-6 is superior because of its
mesoporous structure with two-dimensional channels like MCM-41 and SBA-15
owing to its better dispersion of catalyst and more rapid difusion of reactants and
products during the reactions [19].
Nowadays, extensive research eforts have been devoted to the eco-friendly
solvent-free conditions. Discarding hazardous organic solvents are the main
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Solvent-free selective oxidation of alcohols with tert-butyl…
problem in chemical industries accounting about 80% of their wastes [20]. The
solvent-free reactions are not interesting just from an ecological point of view,
but also as they take place more efciently and selectively with respect to their
solution counterpart [21, 22].
The homogeneous catalysts undergoing problems related to their separation and
recovery may also bring some unwanted metal impurity in the products [23]. Hence,
for efcient recovery and recycling of the homogeneous catalysts, many investiga-
tions have been focused on their immobilization onto diferent solid supports [24].
Recently, Kumar and co-workers have developed diferent supported Au nano-
structures (nanorods, nanohexagons and nanostars) on amorphous titanium dioxide
(TiO2), and the prepared nanocomposites were utilized as efcient photocatalysts in
the oxidation of methanol to formaldehyde under natural sunlight irradiation [25].
The supported palladium complexes have been widely used as heterogene-
ous catalysts for the oxidation of alcohols [26], epoxidation of olefns [27, 28] and
Suzuki and Heck coupling reactions [29–34]. For example, Chirra and co-workers
have synthesized a novel Pd-KIT-6 catalyst by a room temperature sol–gel method
and utilized this material in Suzuki–Miyaura cross-coupling reactions in the solvent-
free conditions under microwave irradiation [35]. Also, Zhang et al. have reported
a proline–palladium catalyst supported on magnetic nanoparticles for the oxidation
of alcohols into the corresponding carbonyl compounds in excellent yields under
atmospheric pressure of molecular oxygen [36].
Recently, we have reported the synthesis, characterization and use of palladium
isatin Schif base complex immobilized into mesoporous silica KIT-6 (Pd-isatin
Schif base@KIT-6) in the selective oxidation of sulfdes to sulfoxides and oxida-
tive coupling of thiols to disulfdes [37]. In this work, we investigated the potential
of Pd-isatin Schif base@KIT-6 in the oxidation of alcohols with tert-BuOOH (70%
aqueous solution) under the solvent-free conditions. In addition, the reusability and
stability of the involved catalyst were studied in this work.
Experimental
Materials and methods
All the used chemical materials were of commercial reagent grade. The alcohols
were obtained from Merck and Fluka. The Pd-isatin Schif base@KIT-6 catalyst was
prepared and characterized based on the procedure previously described in detail
[37]. The Fourier transform infrared (FT-IR) spectra were obtained as KBr pellets in
the wavenumber range of 400–4000 cm−1 with a Thermo SCIENTIFIC NICOLET
iS10 spectrometer. An ICP-SpectroCiros CCD instrument was used for the induc-
tively coupled plasma spectroscopy to determine the metal content of the catalyst. A
ʼ
Panalytical X pert Pro difractometer with Cu-Kα radiation was employed to obtain
the X-ray powder difraction (XRD) patterns of the powder samples at room tem-
perature. A Zeiss Sigma VP-500 FE-SEM instrument was used to take scanning
electron micrographs. TEM images were recorded using a Zeiss-EM10C transmis-
sion electron microscope. The progress of the reaction was studied by thin-layer
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D. Mousavi et al.
chromatography (TLC) on silica-gel polygram SILG/UV 254 plates. The gas chro-
matography (GC) was carried out by a Philips GC-PU 4600 instrument armed with
a fame ionization detector (FID) and a 2 m column packed with silicon DC-200.
General procedure for the oxidation of alcohols with tert‑BuOOH catalyzed
by Pd‑isatin Schif base@KIT‑6 under solvent‑free conditions
In a test tube equipped with a condenser, a mixture of alcohol (1 mmol), Pd-isatin
Schif base@KIT-6 (20 mg, 0.0048 mmol), as the catalyst, and tert-BuOOH (70%
aqueous solution), as the oxidant, was prepared. The test tube was put in an oil bath
at 50 °C, and the mixture was stirred for the appropriate times. The reaction pro-
gress was checked by thin-layer chromatography (TLC) using eluent n-hexane: ethyl
acetate with various ratios. After the completion of reaction, the solid catalyst was
fltered and washed thoroughly with diethyl ether, and the combined washings and
fltrates were purifed on a silica-gel column to achieve the pure product. The prod-
ucts were identifed by comparing their physical data with the authentic materials.
Results and discussion
Catalytic oxidation of alcohols
Scheme 1 shows the preparation route of Pd-isatin Schif base@KIT-6 catalyst.
At frst, the mesoporous silica KIT-6 was prepared according to the procedure as
reported by Kleitz et al. [38]. Then, the prepared KIT-6 was reacted with 3-amino-
propyltriethoxysilane (3-APTES) to obtain amino-functionalized KIT-6 (KIT-6-pr-
NH2). Subsequently, the condensation reaction between the amine group of KIT-
6-pr-NH2 and the keto group at the third position of isatin resulted in isatin Schif
base@KIT-6. Finally, the Pd-isatin Schif base@KIT-6 catalyst was synthesized by
the reaction of dissolving palladium(II) acetate in methanol with the above prepared
isatin Schif base@KIT-6. The Pd content of the prepared catalyst was determined
by ICP, showed a value about 0.24 mmol/g of supported catalyst.
The high catalytic activity of Pd-isatin Schif base@KIT-6 in the selective oxi-
dation of sulfdes and oxidative coupling of thiols [37] encouraged us to study the
ability of this heterogeneous catalyst in other organic transformation reactions such
as oxidation of alcohols to carbonyl compounds. In this regard, to achieve the opti-
mized reaction conditions, the efect of reaction parameters including kind of sol-
vent and oxidant, temperature and catalyst amount, was investigated in the oxidation
of benzyl alcohol as a model reaction.
Firstly, diferent solvents such as acetonitrile, methanol, ethanol, water, toluene,
chloroform, dichloromethane, as well as the solvent-free conditions were used for
the oxidation of benzyl alcohol with tert-BuOOH in the presence of Pd-isatin Schif
base@KIT-6. The obtained results (Table 1) showed that the higher amount of ben-
zaldehyde was obtained under the solvent-free conditions (Table 1, entry 8). Hence,
the efect of reaction parameters was studied on the solvent-free conditions.
1 3

Solvent-free selective oxidation of alcohols with tert-butyl…
Scheme 1 Preparation route of Pd-isatin Schif base@KIT-6 catalyst
1 3

D. Mousavi et al.
Table 1 The efect of solvent on
the oxidation of benzyl alcohol
to benzaldehyde with tert-
BuOOH catalyzed by Pd-isatin
Schif base@KIT-6a
Entry
Solvent
Time (h)
Isolated
yield
(%)
1
2
3
4
5
6
7
8
CH3CN
CH3OH
C2H5OH
H2O
Toluene
CHCl3
3
3
3
3
3
3
3
3
65
53
70
47
38
25
30
90
CH2Cl2
Solvent-free
aReaction conditions: benzyl alcohol (1 mmol), tert-BuOOH
(3 mmol), catalyst (20 mg), solvent (1 mL), T=50 °C
To investigate the efect of temperature on the reaction, the oxidation of benzyl
alcohol was carried out in the range of 25–60 °C, while the other parameters were
kept fxed. The results (Table 2) showed that the benzaldehyde yield enhanced with
increasing temperature, and the highest yield was observed at 50 °C. Therefore, in
this catalytic system, 50 °C was chosen as the optimum temperature.
Also, the catalyst amount in the oxidation of benzyl alcohol was optimized. The
results given in Table 3 reveal a trace amount of product in the absence of a catalyst,
while increasing the catalyst amount from 5 to 20 mg led to more conversion of
alcohol. By using 25 mg of the catalyst, no noticeable increase in the yield of the
product was observed. Therefore, 20 mg (0.0048 mmol) of the catalyst was selected
as the optimum catalyst amount.
Another important factor in the oxidation of alcohol is the nature of oxidant.
Diferent oxygen donors such as 30% H2O2, urea hydrogen peroxide (UHP), tert-
BuOOH (70% aqueous solution) and NaIO4 were tested for the oxidation of ben-
zyl alcohol in the presence of Pd-isatin Schif base@KIT-6 catalyst. The results
(Table 4) showed that among them, tert-BuOOH (70% aqueous solution) provides
the best benzaldehyde yield.
Table 2 The efect of
Entry
Temperature (°C) Time (h)
Isolated
yield
(%)
temperature on the oxidation of
benzyl alcohol to benzaldehyde
with tert-BuOOH catalyzed by
Pd-isatin Schif base@KIT-6
under solvent-free conditionsa
1
2
3
4
5
25
30
40
50
60
3
3
3
3
3
30
38
63
90
85
aReaction conditions: benzyl alcohol (1 mmol), tert-BuOOH
(3 mmol), catalyst (20 mg)
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Solvent-free selective oxidation of alcohols with tert-butyl…
Table 3 The efect of catalyst
Entry
catalyst amount Time (h)
Isolated yield (%)
amount on the oxidation of
benzyl alcohol to benzaldehyde
with tert-BuOOH catalyzed by
Pd-isatin Schif base@KIT-6
under solvent-free conditionsa
(mg)
1
2
3
4
5
6
0
5
10
15
20
25
3
3
3
3
3
3
Trace
35
48
67
90
87
aReaction conditions: benzyl alcohol (1 mmol), tert-BuOOH
(3 mmol), catalyst, T=50 °C
Table 4 The efect of various
oxidants on the oxidation of
benzyl alcohol to benzaldehyde
catalyzed by Pd-isatin Schif
base@KIT-6 under solvent-free
conditionsa
Entry
Oxidant
Time (h)
Isolated yield (%)
1
2
3
30% H2O2
H2O2/urea (UHP)
tert-BuOOH (TBHP,
70% aqueous solu-
tion)
3
3
3
70
53
90
4
Anhydrous tert-
3
85
BuOOH (26%
TBHP in benzene)
5
6
NaIO4
No oxidant
3
3
18
Trace
aReaction conditions: benzyl alcohol (1 mmol), oxidant (3 mmol),
catalyst (20 mg), T=50 °C
Scheme 2 Oxidation of alcohols with tert-butyl hydroperoxide (TBHP) catalyzed by Pd-isatin Schif
base@KIT-6 under solvent-free conditions
Afterward, the ability of this heterogeneous catalyst in the oxidation of vari-
ous types of primary and secondary alcohols was studied under the optimum reac-
tion conditions (Scheme 2). The results are presented in Table 5. As seen, diferent
benzylic alcohols including electron-donating (such as –CH3 and –C(CH3)3) and
electron-withdrawing substitutes (e.g. –NO2 and –Cl) on benzene ring, were selec-
tively oxidized into the corresponding carbonyl compounds with good to excellent
yields, without any overoxidation to the corresponding carboxylic acid (Table 5,
entries 1–7). Also, the benzylic alcohols containing electron-withdrawing groups
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D. Mousavi et al.
Table 5 Oxidation of various alcohols with tert-BuOOH catalyzed by Pd-isatin Schif base@KIT-6
under solvent-free conditionsa
Entry
Alcohol
Product
Time (h)
3
Yield (%)
87
CHO
CH2OH
1
CHO
CH2OH
2
3
4
5
3
3
3
3
91
90
93
71
Me
Me
CHO
CHO
CH2OH
MeO
MeO
CH2OH
(Me)3C
(Me)3C
CHO
CHO
CH2OH
Cl
Cl
CH2OH
6
3
58
Cl
Cl
CH2OH
CHO
7
8
3
3
63
82
O2N
O2N
CHO
CH2OH
H2N
H2N
9
3
3
78
71
OH
CHO
O
O
10
CHO
OH
CHO
11
12
3
4
72
85
OH
O
OH
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Solvent-free selective oxidation of alcohols with tert-butyl…
Table 5 (continued)
Entry
Alcohol
Product
Time (h)
4
Yield (%)
83
OH
O
13
OH
O
14
15
4
4
78
74
OH
O
OH
O
16
4
67
aReaction conditions: alcohol (1 mmol), tert-BuOOH (3 mmol), catalyst (20 mg), T=50 °C
in para-position exhibit less activity than the electron-donating counterparts. The
involved catalytic system was found to be efective in oxidizing the primary ali-
phatic alcohols. The results showed that these aliphatic alcohols were converted to
carbonyl compounds with a good yield (Table 5, entries 9 and 10). Moreover, this
catalyst was efective for the oxidation of aliphatic and aromatic secondary alco-
hols, and the corresponding ketones were obtained in good yields (Table 5, entries
11–15). The present oxidizing system could be used for the oxidation of sterically
hindered alcohols such as diphenylmethanol. In this oxidation process, the corre-
sponding ketone was obtained with the good yield (Table 5, entry 15). Furthermore,
in this catalytic system, furfuryl alcohol as a heteroaromatic alcohol was oxidized to
furfural with a good yield without any decomposition or polymerization (Table 5,
entry 8).
The advantages of this method such as high yields of products, environment
benignity and recyclability make it amenable to scalability readily. As an example, a
scaled up procedure (10 mmol) for oxidation of benzyl alcohol led to isolation of the
benzaldehyde in 85% yield at the same time and conditions mentioned in Table 5.
The proposed mechanism for oxidation of alcohols with tert-BuOOH catalyzed
by Pd-isatin Schif base@KIT-6 is given in Scheme 3. The catalytic cycle begins
with binding of the alcohol to the Pd(II) catalyst (A) to form alcohol bound interme-
diate B. Deprotonation of B then occurs to form a Pd alkoxide (C), which undergoes
β-hydride elimination to release the carbonyl product and form a Pd hydride species
(D). The Pd hydride can reductively eliminate an equivalent of acid to form Pd(0),
which is then reoxidized to Pd(II) catalyst by tert-BuOOH and 2 equivalent of acid
1 3

D. Mousavi et al.
Scheme 3. Proposed mechanism for oxidation of alcohols with tert-BuOOH catalyzed by Pd-isatin
Schif base@KIT-6
[39–41]. Hence, any steric hinderance around the hydroxyl group of alcohols such
as ortho-substituted benzylic alcohols (Table 5, entry 6) or more hindered secondary
alcohols such as diphenylmethanol (Table 5, entry 16) causes longer reaction time
and lower yields. Also, the oxidation of benzyl alcohol was controlled in the pres-
ence of Ph2NH as the radical trap and results showed that there was no change in the
catalyst activity.
A comparison of the Pd-isatin Schif base@KIT-6 catalyst with other reported
ones, presented in Table 6. As seen, our system has some advantages including short
reaction time and high catalytic performance such as selectivity, TON and TOF
under the solvent-free conditions.
Catalyst reusability
To explore the reusability and stability of the Pd-isatin Schif base@KIT-6 catalyst,
its activity in the oxidation of benzyl alcohol was tested for fve subsequent cycles.
At the end of each cycle, the solid catalyst was simply fltered from the reaction
mixture, washed carefully with methanol and dried in vacuum. Then, the recycled
catalyst was used for the subsequent run under the optimum reaction conditions. The
results show that it is possible to reuse the catalyst several times without noticeable
loss of its initial activity (Table 7). After each run, the fltrate was analyzed by the
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Solvent-free selective oxidation of alcohols with tert-butyl…
1 3

D. Mousavi et al.
Table 7 Reusability and
Run
Time (h)
Yield (%)b
Pd leached (%)c
stability of Pd-isatin Schif
base@KIT-6 catalyst in the
oxidation of benzyl alcohol to
benzaldehyde with tert-BuOOH
under solvent-free conditionsa
1
2
3
4
5
3
3
3
3
3
90
87
85
85
83
2.1
1.5
0
0
0
aReaction conditions: benzyl alcohol (1 mmol), tert-BuOOH
(3 mmol), catalyst (20 mg), T=50 °C
bIsolated yield
cDetermined by ICP
inductively coupled plasma (ICP) technique to determine the amount of leached Pd.
It was found that just a small amount of palladium had been leached in the frst two
runs (Table 7).
The recovered catalyst was also characterized by FT-IR, XRD, SEM and TEM
techniques. The FT-IR spectrum of the recycled catalyst presented in Fig. 1b was
found to be similar to that of fresh catalyst (Fig. 1a). For the recycled catalyst, the
FT-IR bands at 1085, 805 and 464 cm−1 can be assigned to Si–O-Si vibrations
and the band at 2932 cm−1 is associated with vibrations of aliphatic CH2 groups.
Moreover, the characteristic frequencies of C=N and C=O stretching modes were
observed at 1624 and 1728 cm−1, respectively. All of these FT-IR bands appeared
for the fresh catalyst (Fig. 1a), as well. The XRD pattern of reused catalyst is
shown in Fig. 2b. As shown, XRD pattern is in good agreement with XRD pat-
tern of fresh catalyst (Fig. 2a). Also, the Debye–Scherrer formula was used to
determine the crystal size of fresh and reused catalyst. The average crystallite
Fig.1 FT-IR spectrum of a fresh and b recycled Pd-isatin Schif base@KIT-6 catalyst
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Solvent-free selective oxidation of alcohols with tert-butyl…
Fig.2 XRD pattern of a fresh and b reused Pd-isatin Schif base@KIT-6 catalyst
size was estimated about 43.5 and 43.7 nm for fresh and reused Pd-isatin Schif
base@KIT-6, respectively. Moreover, the SEM and TEM images of the recov-
ered Pd-isatin Schif base@KIT-6 compared with the fresh one (Figs. 3 and 4,
respectively) showed that the morphology remained intact after recovering.
These observations demonstrated the preservation of the catalyst’s structure after
recycling.
Conclusions
In summary, palladium(II) isatin Schif base complex supported into the mesoporous
silica KIT-6, Pd-isatin Schif base@KIT-6, was used as a heterogeneous catalyst
for the oxidation of a wide range of alcohols with tert-butyl hydroperoxide (TBHP,
70% aqueous solution) as an oxidant under the solvent-free conditions. The good to
excellent yields, eco-friendly and selective oxidation of alcohols without by-product
formation can be mentioned as the benefts of this protocol for the oxidation of alco-
hols. Furthermore, the involved catalyst could be conveniently recovered by simple
fltration and reused fve times with no signifcant loss of efciency.
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D. Mousavi et al.
Fig.3 SEM images of a fresh and b recovered Pd-isatin Schif base@KIT-6 catalyst
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Solvent-free selective oxidation of alcohols with tert-butyl…
Fig.4 TEM images of a fresh and b recovered Pd-isatin Schif base@KIT-6 catalyst
Acknowledgements The support received for this work from Vali-e-Asr University of Rafsanjan is grate-
fully acknowledged. The corresponding author also appreciates Professor Majid Moghadam from Univer-
sity of Isfahan, Dr. Zahra Pakdin-Parizi from Razavi Hospital of Mashhad, Dr. Jamileh Seyedyazdi, and
Dr. Parisa Salarizadeh from Vali-e-Asr University of Rafsanjan for their valuable helps.
Funding This research did not receive any specifc grant from funding agencies.
Availability of data and material Not applicable.
Code availability Not applicable.
1 3

D. Mousavi et al.
Compliance with ethical standards
Confict of interes The authors declare that they have no confict of interest.
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