Synthesis of nano magnetite Fe3O4 based vanadic acid: A highly efficient and recyclable novel nanocatalyst for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ols)

Article abstract of DOI:10.5562/cca2854

Nano magnetic Fe₃O₄ based vanadic acid [MNPs@VO(OH)₂] (average diameter 20-26 nm) has been synthesized by grafting VOCl₃ on the Fe₃O₄ surface nanoparticles as a retrievable supporter to pro

Full text of DOI:10.5562/cca2854

O R I G I N A L S C I E N T I F I C P A P E R
Croat. Chem. Acta 2016, 89(3), 317–322
Published online: November 2, 2016
DOI: 10.5562/cca2854
Synthesis of Nano Magnetite Fe
3
O Based Vanadic
4
Acid: A Highly Efficient and Recyclable Novel Nano-
catalyst for the Synthesis of 4,4’-(arylmethylene)-
bis(3-methyl-1-phenyl-1H-pyrazol-5-ols)
Maliheh Safaiee,1, Mohammad Ali Zolfigol, Fatemeh Derakhshan-Panah, Vahid Khakyzadeh, Leila Mohammadi
*
2
2
3
2
1
2
3
Department of Medicinal Plants Production, Nahavand University, Nahavand, 6593139565, Iran
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran
Department of Chemistry, Khaje Nasir Toosi University, Tehran 1969764499, Iran
*
Corresponding author’s e-mail address: azalia_s@yahoo.com & msafaiee@nahgu.ac.ir
RECEIVED: March 3, 2016  REVISED: September 12, 2016  ACCEPTED: September 12, 2016
Abstract: Nano magnetic Fe
3
O
4
based vanadic acid [MNPs@VO(OH)
2
] (average diameter 20–26 nm) has been synthesized by grafting VOCl on
3
the Fe surface nanoparticles as a retrievable supporter to produce novel heterogeneous reusable solid acid with dual ability (Bronsted and
3
O
4
Lewis acid) followed by stirring in the air. The resultant material was characterized by scanning electron microscopy (SEM), transmission
electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD) analysis and energy-dispersive X-ray
spectroscopy (EDX). Significantly, the as-prepared [MNPs@VO(OH)
arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols). Additionally, the newly synthesized heterogeneous solid acid catalyst can be reused
for several times without apparent loss of its catalytic activity.
2
] exhibits a high catalytic activity in the synthesis of 4,4’-
(
Keywords: nano magnetite Fe
heterogeneous, nanoparticles.
3
O
4
based vanadic acid, 4,4’-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols), acid catalysed reactions,
dodecylsulfate,[10] tetramethyl-tetra-3,4-pyridinoporphyra-
INTRODUCTION
[
11]
zinato copper(II) methyl sulfate,
poly(ethyleneglycol)-
[
12]
[13]
OWADAYS, the pyrazolone derivatives are an
important class of heterocyclic compounds were paid
bound sulfonic acid,
cellulose sulfuric acid,
lithium
[14]
N
hydroxide monohydrate, silica chloride nano particle[15]
much attention for their various biological activities such as
antipyretic, antitumor, analgesic, antianxiety, and anti-
can be used as catalysts for this transformation.
However, some of these methods suffer from at
least one of the following disadvantages: using the
expensive catalyst at reflux condition, long reaction time,
low yield, non-recovered catalyst, tedious work-up
procedure and the using of large amount of catalyst. Thus,
there is still a need to develop a new and convenient
method for the synthesis of 4,4′-(arylmethylene)bis(1H-
pyrazol-5-ols).
[
1]
inflammatory properties. More specifically, derivatives
such as 4,4′ (arylmethylene)-bis-(1H-pyrazol-5-ols) are
applied as fungicides, pesticides, insecticides and
dyestuffs.
The condensation of aldehydes with two equivalents
of 3-methyl-1-phenyl-5-pyrazolone is a known used path to
synthesize 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols).
[
2]
[3]
[4]
[
5]
Xanthan sulfuric acid, phosphomolybdic acid,[7]
[6]
Therefore, finding an efficient and capable protocol for
the preparation of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) is
silica sulfuric acid,[8] 3-aminopropylated silica gel,[9] sodium
This work is licensed under a Creative Commons Attribution 4.0 International License.

318
M. SAFAIEE et al.: Synthesis of Nano Magnetite Fe
3
4
O Based Vanadic Acid …
very important. Thus, design of novel nano magnetically
separable catalytic systems have attracted attention in
recent times as an interesting alternative to improve the
efficient separation of heterogeneous (nano) catalysts from
solutions over reaction completion by applying a simple
magnet, providing improved recyclability in the designed
Typical Procedure for Synthesis of Nano
Magnetic Fe Based Vanadic Acid
3
O
4
MNPs Fe
previous report by Qu et al.
MNPs Fe (1g) suspended in n-Hexane (15 ml) with
3 4
O particles (I) were prepared according to a
[21]
3 4
O
sonication for 5 minutes. Then, vanadiumoxytrichloride (1 g)
was dissolved in n-hexane (10 mL). The mixture was added
drop wise to MNPs Fe O suspension (15–20 min) and
3 4
shaked for 30 minutes. The result material were separated
by an external magnet, washed three times with ethanol,
dried under vacuum, and shaked in the air for 48 h to
promote the hydrolysis of V-Cl bonds to yield the final
catalyst.
[
16]
systems.
In addition, surface modification impacts the activity
and selectivity of magnetite nano-catalysts.[17]
Acid catalyzed reactions have been also widely used
in the modern chemical industry. It has been showed that
catalytic systems that contain both Lewis and Bronsted
acidity are more beneficial than Lewis or Bronsted acidic
catalysts alone.[
18]
Among the various transition metals as a Lewis acid,
vanadium exists on the surface of the earth more plentifully
and vanadium based oxidants are effectively used for
General Procedure for Synthesis of
Bis(pyrazolyl)methanes
To a solution of an aldehyde (1 mmol), 3-methyl-l-phenyl-
[
19]
various organic reactions.
5
-pyrazolone (2 mmol), and 4-5 drop ethanol was added
Vanadium and vanadium peroxides generate a
number of biological and biochemical responses and
have a potential as insulin-mimetic agents in the
treatment of human diabetes. Moreover, vanadium is an
essential prosthetic group of some haloperoxidase
MNPs@VO(OH) (20 mg). The resulting mixture was
2
magnetically stirred at 40 °C. The progress of the reaction
was monitored by TLC. After the completion of the
reaction, the catalyst was separated from the product by an
external magnet and washed with ethanol (20 mL) and
reused for subsequent runs. The mixture was concentrated
to give the crude product. Finally, the products were
purified by column chromatography on silica gel (n-
hexane/EtOAc) or by recrystallization from ethanol.
[
20]
enzymes.
Therefore, immobilization of the functionalized acid
via covalent attachment to the supporting materials can
combine the acid characteristics with the advantages of
magnetic nanoparticles to design the acidic catalyst that
facilitate catalyst recovery, recycling and reducing effluent
contamination.
RESULTS AND DISCUSSION
In continuation of our previously reported methodo-
logies for designing, synthesis and applications of tasked
specific heterogeneous catalysts such as silica based
EXPERIMENTAL
Chemicals and Apparatus
The materials were purchased from Merck and Fluka and
were used without any additional purification. All reactions
were monitored by thin layer chromatography (TLC) on gel
F254 plates. The synthesized catalyst was characterized by
FT-IR, XRD, SEM, TEM, and elemental analysis.
[22]
[23]
[24]
sulfuric, phosphoric, vanadic acid, and magnetic
[25]
nano particles herein, we wish to report the synthesis
and application of novel nano magnetite Fe based
vanadic acid [MNPs@VO(OH) ] with dual ability both as
Lewis and Bronsted acid sites. The described catalyst
MNPs@VO(OH) ] was synthesized successfully and
3
O
4
2
[
2
XRD patterns of all catalysts were performed on a
APD 2000, Ital structure with Cu Kα radiation (k = 0.1542
nm) operating at 50 kV and 20 mA in a 2 h range of 10–70°
with step size 0.01° and time step 1.0 s to assess the
crystallinity of the catalyst.
used for the synthesis of 4,4′-(arylmethylene)bis(1H-
pyrazol-5-ols).
Initially, Fe
3
O
4
particles (I) were prepared according
based
to a previous report. Then, nano magnetic Fe
3 4
O
The weight loss between 200 and 600 °C was
determined. Semi-quantitative EDX (Röntec, Quantax/QX2)
analysis was used for the characterization of element
concentration and vanadium distribution within prepa-
red catalysts. The SEM analyses were done with a
TESCAN/MIRA with a maximum acceleration voltage of the
primary electrons between 10 and 15 kV. Transmission
electron microscope, TEM measurements were carried out
on a Philips CM10 analyzer.
MNPs@ VO(OH)
2
Scheme 1. Synthesis of nano magnetic Fe
acid [MNPs@VO(OH) ].
3 4
O based vanadic
2
Croat. Chem. Acta 2016, 89(3), 317–322
DOI: 10.5562/cca2854

M. SAFAIEE et al.: Synthesis of Nano Magnetite Fe
3
O
4
Based Vanadic Acid …
319
3 4 2
Figure 1. FT-IR spectra (a) Fe O and (b) MNPs@VO(OH)
vanadic acid [MNPs@VO(OH)
2
] was synthesized by the
followed by stirred in
reaction of Fe particles with VOCl
3
O
4
3
the air (Scheme 1) and its structure was identified by IR,
SEM, XRD and EDX.
In order to confirm the modification of the
magnetite surface, the FT-IR spectrum of the prepared
materials were obtained and have been shown in Figure 1.
Figure 1. shows the FT-IR spectra of the MNPs (a) and
MNPs@VO(OH)
5
2
(b). The Fe−O stretching vibraꢀon near
92 cm and the O-H stretching vibration at 3429 cm−1
were observed for the Fe (Figure 1a). The introduction
of VO(OH) to the surface of MNPs is confirmed by the
−1
3 4 2
Figure 2. The XRD of the (a) Fe O and (b) [MNPs@VO(OH) ].
3 4
O
2
−1
bands at 786.7 and 1007 cm assigned to the V−O and V=O
respectively, and the bands at 3384 assigned to the O−H
stretching vibration.
can be remained after the surface modification with
VO(OH) and new peaks attributable to these groups could
2
not be detected in the XRD. However, the crystallinity of
the samples clearly decreases after the coating process and
the catalyst was going to amorphous structure. These
results provide further evidence that functionalization on
the nano magnetite take place.
The EDX elemental analysis is shown in Figure 3.
From the spectrum, it can be seen that iron, oxygen and
vanadium elements present in the [MNPs@VO(OH) ]
2
samples which is in good agreement with the proposed
catalyst structure (Figure 3).
3 4 2
XRD patterns of (a) Fe O and (b) [MNPs@VO(OH) ]
are shown in Figure 2. As shown in Figure 2a, weak
diffraction peaks with 2θ at 30°, 35.4°, 43°, 53.4, 57.4°, and
[
26]
6
2
2.4° which are attributed to the (2 2 0), (3 1 1), (4 0 0), (4
2), (5 1 1) and (4 4 0) phases of Fe , respectively.
In Figure 2b, we can observe that the XRD pattern of
the [MNPs@VO(OH) ] is similar to the pattern of Fe
nanoparticles because the structure of [MNPs@VO(OH)
3
O
4
2
3
O
4
2
]
TEM and SEM images of the synthesized catalyst
Figure 3. EDX analysis for [MNPs@VO(OH)
2
].
2
Figure 4. The TEM (a) and SEM (b) of the [MNPs@VO(OH) ].
DOI: 10.5562/cca2854
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320
M. SAFAIEE et al.: Synthesis of Nano Magnetite Fe
3
4
O Based Vanadic Acid …
Table 1. Optimization of the catalyst amount and
temperature on the reaction of 3-methyl-1-phenyl-1H-
pyrazol-5(4H)-one with benzaldehyde
Time/
min
Yield(a)
(%)
1
2
3
Entry
Catalyst / g
Temperature/ °C
R: aryl, heteroaryl
1
2
3
5
6
3
5
6
0.04
0.04
0.02
0.01
0.005
0.04
0.01
0.005
60
40
40
40
40
25
25
25
10
10
10
10
20
30
30
30
92
93
90
75
46
78
75
35
Scheme 2. Tandem Knoevenagel–Michael reaction of 1-
phenyl-3-methyl-5-pyrazolone with aldehydes catalyzed by
MNPs@VO(OH) ].
2
[
were recorded and showed in Figure 4. The average
diameter of the catalyst is around 25 nm with an
approximate spherical shape.
The activity of the catalyst was subsequently
investigated upon characterization in the synthesis of
bis(pyrazolyl)methanes (Scheme 2).
Reaction conditions: benzaldehydes (1 mmol), 3-methyl-l-phenyl-5-pyra-
zolone (2 mmol), catalyst, 4-5 drop ethanol at different temperature.
(
a)
Isolated yield.
To optimize the reaction conditions, the solvent-free
condensation of 3-methyl-1-phenyl-5-pyrazolone (1) (2
mmol) with benzaldehyde (1 mmol), as model reaction
using different amounts of catalyst at range of 25–60°C was
examined (Table 1). The best results were obtained using
of aromatic aldehydes with electron releasing groups
(methoxy, methyl), electron withdrawing substituents
(nitro), in the ortho, meta and para positions of the
benzene ring, polycyclic aromatic (naphthyl) and
heterocyclic aldehyde (furyl, pyridyl) reacted efficiently
with two equivalents of 5-methyl-2-phenyl-2,4-dihydro-3H-
pyrazol-3-one to afford the product 3a–p in a short
experimental time (5–45 min) with high yields (72–96 %).
The reusability of the catalysts is one of the most
2
0.02 g of [MNPs@ VO(OH) ] at 40°C. After optimization of
the reaction conditions, to explore the efficiency and the
scope of the presented protocol, 3-methyl-1-phenyl-5-
pyrazolone was treated with structurally diverse aromatic
aldehydes under the optimized reaction conditions in the
important benefits and makes it useful for commercial
applications. Thus, the recovery and reusability of
presence of [MNPs@VO(OH)
2
]
as catalyst. The
corresponding results are depicted in Table 2.
[MNPs@VO(OH)
2
] were investigated. For this purpose,
The results reported in Table 2 showed that a variety
condensation of 3-methyl-1-phenyl-5-pyrazolone with
2
Table 2. The preparation of bis(pyrazolyl)methanes 3a–p using [MNPs@VO(OH) ] as catalyst at 40 °C
Entry
R
product
Time (min)
Yield(a) (%)
M.p. °C (lit.)Ref
1
2
3
4
5
6
7
8
9
C
6
H
5
C
C
3a
3b
3c
3d
3e
3f
10
5
90
95
96
94
87
85
89
92
84
87
79
72
74
91
83
79
168–170 (171–172)[27]
229–231(230–232)[27]
145–147 (149–150)[27]
221–223 (224–225)[27]
181-183 (182−184)[28]
213–215 (207–209)[27]
150–152 (153–154)[27]
235–236 (236–237)[27]
173–175 (172–175)[29]
201–203 (203–204)[27]
201–203 (203–204)[27]
210-212 (210−213)[28]
175-177 (155−157)[28]
205–207 (206−208)[27]
190–193 (189–191)[27]
228–231 (230–232)[27]
4- NO
3- NO
2
6
6
H
4
4
2
H
5
2-NO
2
C
6
H
4
10
5
4-FC
6
H
4
4-ClC
3-ClC
2-ClC
6
6
6
H
H
H
4
4
4
10
10
10
15
15
15
30
45
10
10
10
3g
3h
3i
3-BrC
6 4
H
1
1
1
1
1
1
1
0
1
2
3
4
5
6
4-MeC
2-MeC
6
H
4
3j
6
H
4
3k
3l
2-MeOC
4-MeOC
6
H
4
4
6
H
3m
3n
3o
3p
2-Naphthyl
2-Furyl
2-Pyridyl
Reaction conditions: Aldehydes (1 mmol), 3-methyl-l-phenyl-5-pyrazolone (2 mmol), MNPs@VO(OH)
Isolated yield.
2
(20 mg), 4–5 drop ethanol at 40 °C.
(
a)
Croat. Chem. Acta 2016, 89(3), 317–322
DOI: 10.5562/cca2854

M. SAFAIEE et al.: Synthesis of Nano Magnetite Fe
3
O
4
Based Vanadic Acid …
321
Figure 5. The reaction of 3-methyl-1-phenyl-5-pyrazolone
with benzaldehydes in the presence of recycled
MNPs@VO(OH) ] within 10 min.
[
2
benzaldehyde was studied. It catalysts were easily
collected by means of a magnet, washed with ethanol and
dried to be reused in subsequent reactions. Recovered
[
2
MNPs@VO(OH) ] was washed with ethanol and has been
also use at least 5 times without any noticeable loss of
catalytic activity (Figure 5).
Scheme 3. Plausible mechanism for the formation of
bis(pyrazolyl)methanes.
2
We believe that the [MNPs@VO(OH) ] activates the
aldehyde group for nucleophilic attack by 3-methyl-1-
phenyl-1H-pyrazol-5-ol (IV) 2 to form (V) which undergoes
Michael addition with second molecule of 3-methyl-1-
phenyl-1H-pyrazol-5-ol to form the product (VI) (Scheme
CONCLUSION
[
30]
3).
The major advantages of the present protocol
In conclusion, we have described the development of a mild
efficient and simple method for the one-pot three-
component condensation reaction of aromatic aldehydes
with 1-phenyl-3-methylpyrazol-5-one in ethanol for the
synthesis of 4,4'-(arylmethylene)bis(1H-pyrazol-5-ol) deriva-
over existing methods can be seen by comparing our re-
sults with the most popular recently reported pro-
cedures, as shown in Table 3. The reaction of benzalde-
hyde with 3-methyl-5-pyrazolones for the preparation
4,4'-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols)
2
tives, catalyzed by [MNPs@VO(OH) ] as a new and hetero-
(
entry 1, Table 3) was chosen as a model reaction and the
geneous organic catalyst at 40°C. The catalyst is char-
acterized by FT-IR, XRD, TEM, SEM and EDX. The procedure
has several advantages such as high reaction rates, ease of
preparation and handling of the catalyst, simple experi-
mental procedure and use of a reusable catalyst.
comparison is in terms of reaction time, reaction
conditions and percentage yields. Shorter reaction time
and milder reaction condition was obtained using SVA
instead of Bronsted acid catalyst.
Table 3. Comparison of the efficiencies of a number of different reported catalysts with SVA in the condensation of
benzaldehyde with 2 equivalents of 3-methyl-l-phenyl-5-pyrazolone
Entry
Catalyst
Solvent/Temperature (°C)
EtOH/40
Time / min
10
Yield (%)
90
Ref
1
2
3
4
5
6
7
8
9
Our catalyst
This work
[10]
[1]
Sodium dodecyl sulfate
Silica-bonded S-sulfonic acid
Silica sulfuric acid
H
2
O/Reflux
EtOH/Reflux
EtOH-H O/70
60
86.8
80
120
60
2
93
[31]
[32]
[33]
[34]
[35]
[36]
Silica-bonded ionic Liuid[spipim]HSO
{[Dsim]AlCl4}
4
EtOH/Reflux
120
60
89
Solvent free /50
EtOH/Reflux
86
[P
4
VPyBuSO
3
H]HSO
4
42
95
SASPSPE
SBPPSA
EtOH/Reflux
180
45
90
Solvent free /80
93
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Croat. Chem. Acta 2016, 89(3), 317–322

322
M. SAFAIEE et al.: Synthesis of Nano Magnetite Fe
3
4
O Based Vanadic Acid …
Acknowledgment. The authors gratefully acknowledge the
Bu-Ali Sina and Nahavand, University Research Councils,
and also Center of Excellence in Development of
Environmentally Friendly Methods for Chemical Synthesis
J. Org. Chem. 2002, 67, 6718; (d) M. Kirihara, Y.
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