Development of sustainable and efficient nanocatalyst based on polyoxometalate/nickel oxide nanocomposite: A simple and recyclable catalyst for reduction of nitroaromatic compounds

Article abstract of DOI:10.1002/jccs.202100057

In this paper, we report the synthesis and characterization of NiO@PolyMo nanocomposite. The newly synthesized nanocomposite was characterized by transmission electronmicroscopy (TEM), energy-dispersive X-ray spectroscopy (EDS), and powder X-ray diffraction (XRD). The particle sizes of the NiO@PolyMo nanocatalyst are in the range of 10–20 nm. Powder XRD patterns show that the phase of NiO@PolyMo remains unaltered even after the functionalization of NiO. The lattice fringes of d = 0.20 nm were observed, which correspond to the (111) plane of NiO phase. The newly synthesized material shows excellent catalytic performance and good selectivity for reduction of nitroarenes. The advantages of the present protocols are mild, and can be carried out using water as a solvent, which is an eco-friendly benign.

Full text of DOI:10.1002/jccs.202100057

Received: 18 February 2021
DOI: 10.1002/jccs.202100057
Revised: 26 March 2021
Accepted: 6 April 2021
A R T I C L E
Development of sustainable and efficient nanocatalyst
based on polyoxometalate/nickel oxide nanocomposite:
A simple and recyclable catalyst for reduction of
nitroaromatic compounds
Sunshine Dominic Kurbah
Department of Chemistry, Pandit
Abstract
Deendayal Upadhyaya Adarsha
Mahavidyalaya, Karimganj, India
In this paper, we report the synthesis and characterization of NiO@PolyMo
nanocomposite. The newly synthesized nanocomposite was characterized by
transmission electronmicroscopy (TEM), energy-dispersive X-ray spectroscopy
(EDS), and powder X-ray diffraction (XRD). The particle sizes of the
NiO@PolyMo nanocatalyst are in the range of 10–20 nm. Powder XRD patterns
show that the phase of NiO@PolyMo remains unaltered even after the func-
tionalization of NiO. The lattice fringes of d = 0.20 nm were observed, which cor-
respond to the (111) plane of NiO phase. The newly synthesized material shows
excellent catalytic performance and good selectivity for reduction of nitroarenes.
The advantages of the present protocols are mild, and can be carried out using
water as a solvent, which is an eco-friendly benign.
Correspondence
Sunshine Dominic Kurbah, Department
of Chemistry, Pandit Deendayal
Upadhyaya Adarsha Mahavidyalaya,
Eraligool-788723, Karimganj, Assam,
India.
Email: sunshinekurbah@yahoo.com
Funding information
North-Eastern Hill University
K E Y W O R D S
nanocomposite, nanocatalyst, nitroarenes, reduction
1 | INTRODUCTION
pharmaceutical, photographic, plastic fields, and other
industrial applications.[8–11] Therefore, development of
Over the years, with fast growth of many industries and
increased release of various types of contaminants there
has been an environmental burden to the atmosphere.
Among these, nitrophenol (4-NP) has also an adverse
impact on the environment.[1–3] 4-NP is also a toxic
nitroarene, which commonly is used in the production of
dyes, pesticides, leather preservative, and also as an inter-
mediate in the production of paracetamol.[3–5] This com-
pound has been proven to be very harmful, not only to
animals but also to plants.[6,7] Therefore, effective
removal of 4-NP is imminent and has received a lot of
attentions. The simplest and efficient method for removal
of 4-NP is the catalytic reduction to 4-amino phenol,
which is an important precursor material in
efficient catalytic system for reduction of 4-nitrophenol to
4-amino phenol not only prevents its toxicity, but also
meets the great demand for 4-AP.
Traditional methods for the production of 4-AP,
required the reduction of 4-NP in the presence of suitable
reducing agents as shown in Scheme 1.[12–15] Therefore, in
order to achieve the reduction of 4-NP to corresponding
4-aminophenol, many noble and non-noble metals have
been frequently utilized as catalysts in the presence of
hydrazine hydrate and NaBH4.[10,14–18] However, there are
many drawbacks associated with the present catalytic sys-
tems, due to the lack of selectivity in the reduction of
nitroarenes, not reusable, and the high cost of noble
metals such as Pd, Ru, Pt, and Au which limits their large-
J Chin Chem Soc. 2021;1–9.
http://www.jccs.wiley-vch.de
© 2021 The Chemical Society Located in Taipei & Wiley-VCH GmbH
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scale commercialization.[19–22] Therefore, it is very impor-
tant to develop catalytic protocols which are more stable,
reusable, low-cost, and noble metal-free catalysts. The cat-
alytic performance of nickel nanoparticles has received
considerable attention recently, because of their low cost
and remarkable catalytic performances in hydrogenation
of nitrophenol, nitrobenzene, and reduction of oxy-
gen.[22–25]
the redox, photocatalytic, and catalytic properties of POMs
can impart unique reactivities to the nanoparticles stabi-
lized by POMs.[28–30]
2 | RESULTS AND DISCUSSION
2.1 | Characterization of NiO@PolyMo
In this context, we developed a simple catalytic
system for reduction of nitroarenes based on nickel
nanoparticles coated with polyoxomolybdate. Hence,
using polyoxometallates as a capping agent or stabiliz-
ing agent would impart additional stability and better
applications of the nanoparticles. As molecular
anions, polyoxometallates have been found to stabilize
the colloidal metal nanoparticles in solution.[26,27]
However, compared to other protecting organic ligands,
The synthetic pathway for NiO@PolyMo nanocatalyst
described in the present study are highlighted in
Scheme 2. The whole process for the synthesis of catalyst
involved the reaction of nickel oxide with poly-
oxomolybdate in deionized water. The resulting mixture
was stirred at room temperature for 5 min and then
heated at 100ꢀC for 1 hr. The resulting mixture was then
cooled to room temperature, dried, and then calcined at
400ꢀC for 3 hr. The resulting dark gray powder obtained
was characterized by transmission electron microscopy
(TEM), EDX, and X-ray diffraction (XRD). TEM analysis
gave direct information with regards to the morphology
and structures of the synthesized materials.
The TEM images of NiO@PolyMo nanocatalyst are
shown in Figure 1a. The maximum number of particle
sizes fall in the range of 10–20 nm in diameter (Figure 1b),
and are irregular in shape, some particles aggregate them-
selves on top of the other particles. In addition, a dark
shell inside the NiO@PolyMo materials was observed that
can be also seen clearly in the TEM images. Furthermore,
the morphology and structure of NiO@PolyMo nanoparti-
cle, when the catalyst was recovered and recycled do not
show much change in their morphology even when the
catalyst was used for five consecutive cycles. Moreover, it
can be seen that from the selected areas electron diffrac-
tion (SAED) pattern, the NiO@PolyMo material is poly-
crystalline in nature (Figure 1c). The existence of each
element such as Ni, O, and Mo in the newly synthesized
NiO@PolyMo was also confirmed by energy-dispersive
X-ray spectroscopy (EDS) mapping (Figure S1). Hence,
these results show that the presence of nickel in the
NiO@PolyMo nanocatalyst. The crystalline nanocatalyst
was also characterized by the powder XRD technique. The
diffraction patterns of NiO@PolyMo nanoparticle are
SCHEME 1 Strategies for nitroarenes reduction by transition
metals
SCHEME 2 Schematic diagram
showing the preparation of
NiO@PolyMo nanocatalyst

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FIGURE 1 (a) TEM image of NiO@PolyMo nanoparticle, (b) Particles size distribution, (c) SEAD pattern of NiO@PolyMo nanocatalyst,
and (d) High resolution transmission electron microscopy image of NiO@PolyMo nanocatalyst
shown in Figure 2. From the powder XRD pattern, it has
been observed that the phase of the newly synthesized
NiO@PolyMo remains unaltered even after the func-
tionalization of NiO, which is in good agreement with the
TEM images. The diffraction peaks appearing at
2θ = 36.92ꢀ, 44.5ꢀ, and 62.50ꢀ correspond to the crystal
planes of (111), (200), and (220), respectively. As shown in
Figure 1d, the lattice fringes of d = 0.20 nm were observed,
which correspond to the (111) plane of the NiO
phase.[25,31]
2.2 | Catalytic reduction of nitroarenes
To evaluate the catalytic activity of NiO@PolyMo, we
carried out the catalytic studies for reduction of various
FIGURE 2 XRD patterns of polyoxomolybdate and
nitroarenes to their corresponding aromatic amines. The
catalytic reduction of 1-iodo-4-nitrobenzene was selected
as the model substrate. Our initial studies were carried
out by examining the impact of catalyst loading and
it was found that 2.0 mg of NiO@PolyMo gave the
best yield (Table 1, Entry 13). When the amount of
NiO@PolyMo was reduced, the yield also decreases and
on the other hand, when the amount of NiO@PolyMo
increased from 2.5 to 3.0 mg, the yield decreased
(Table 1, Entry 14–16). The catalytic reduction of 1-iodo-
4-nitrobenzene was tested using variety of organic
NiO@PolyMo nanocatalyst
solvents and the results are presented in Table 1. It is
evident that the reaction proceeds smoothly in water as a
medium (Table 1, Entry 4). The effects of temperature
and reducing agents were also studied and the results are
depicted in Table 1. The best results were obtained with
NaBH4 as reducing agents at room temperature, which
selectively gave the corresponding p-iodoaniline with
91% conversion (Table 1, Entry 13). Profound effects

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TABLE 1 Optimization of the reaction conditions for catalytic reduction of nitroarenesa
Entry
1
Catalyst
1 mg
Reductants
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NaBH4
NH2NH2
NaBH4
Solvents
CH3OH
C2H5OH
CH3CN
H2O
Temp (ꢀC)
RT
Time/hr
Yield (%)b
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
69
72
23
81
11
54
63
80
78
74
7
2
1 mg
RT
3
1 mg
RT
4
1 mg
RT
5
1 mg
Toluene
DMF
DMSO
H2O
RT
6
1 mg
RT
7
1 mg
RT
8
1 mg
50
9
1 mg
H2O
75
10
11
12
13
14
15
16
17
1 mg
H2O
100
RT
0.0 mg
1.5 mg
2.0 mg
2.5 mg
3.0 mg
2.0 mg
Ni@bulk
H2O
H2O
RT
85
91
88
86
41
11
H2O
RT
H2O
RT
H2O
RT
H2O
RT
H2O
RT
Abbreviations: DMF, dimethylformamide; DMSO, dimethyl sulfoxide.
aReaction conditions: Substrate (2.0 mmol), catalyst (2.0 mg), Reducing agents (3.0 mmol), solvent (5.0 ml), temperature (RT).
bIsolated yield after chromatography.
were observed on the conversion of the desired products
by altering different reaction parameters. The results
obtained amplified the higher activity of the present
protocols.
corresponding halogenated anilines in excellent yields
(Table 2, Entry 2, 5, 14, and 15). 4-nitrobenzonitrile
was also reduced to p-aminobenzonitrile with 87% yield
(Table 2, Entry 4). Halogen groups presented at the ortho and
meta-position, such as o-chloro nitrobenzene and p-chloro
nitrobenzene were also converted to o-chloroaniline (94%),
and 3-chloroaniline (95%) which is lower than that of p-
chloroaniline (Table 2, Entry 6, 7). The catalytic reduction of
1,2-dinitrobenzene and 1,4-dinitrobenzene was also per-
formed which yielded o-phenylene diamine (91%), and p-
phenylene diamine (93%) in excellent conversion (Table 2,
Entry 12, 13). We were delighted to find that a numerous
functionalized nitroarenes, especially those bearing
electron-deficient substrates, are converted successfully
and selectively into the desired products with excellent
yields. Substrates containing methyl groups at ortho, meta,
and para-position, methoxy, and amino groups in the
para-position were also reduced smoothly and were iso-
lated in excellent yields (Table 2, Entry 9–11, 8, 16). The
reduction reaction of p-nitrophenol was carried out, it was
To validate the scope and application of this novel
heterogeneous catalytic procedure, we extended our strat-
egy using wide ranges of nitroarenes. The substrates were
selected those having both electron-donating and
electron-withdrawing groups, to determine the scope of
the reduction processes, and the results are presented in
Table 2. Hence, it can be seen that several nitroarenes
bearing electron-rich (OMe, NMe) and electron-deficient
(Halogen, CN, NO2) groups undergoes reduction success-
fully with water as solvent, to produce the corresponding
amines groups, respectively, in excellent yields. Nitroben-
zene was also successfully reduced to aniline with 94%
conversion within the time frame of 4 hr. The halogens
containing groups of nitrobenzene, such as 1-bromo-
4-nitrobenzene, 1-iodo-4-nitrobenzene, and 1-chloro-
4-nitrobenzene were also successfully converted to their

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TABLE 2 Reduction of various nitroarenes with NiO@Poly-Mo nanocatalysta
Entry
Reactants
Products
Time (hr)
Conv. (%)
Yieldb (%)
Select. (%)
1
4.0
97
94
97
2
3
4
5
6
7
3.45
4.0
98
60
90
98
98
97
95
54
87
96
94
95
97
90
97
98
96
98
4.0
4.0
3.45
4.0
8
4.0
95
90
95
9
4.0
4.0
90
86
87
83
97
97
10
11
4.0
89
81
91
(Continues)

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TABLE 2 (Continued)
Entry
Reactants
Products
Time (hr)
Conv. (%)
Yieldb (%)
Select. (%)
12
4.0
95
91
96
13
3.45
97
93
96
14
15
16
4.0
4.0
4.0
99
94
99
97
91
95
98
97
96
17
4.0
91
74
81
aStandard reaction conditions: Substrate (2.0 mmol), catalyst (2.0 mg), NaBH4 (3.0 mmol), solvent (5.0 ml), temperature (RT).
bIsolated yield after chromatography.
observed that the yield of the reduction product, p-
aminophenol is lower compared to other substituents' pres-
ence on the benzene ring, the lower yield could be attrib-
uted to the acidity of the phenolic hydroxyl group. Having
demonstrated the wide substrate scope of this reaction, we
also performed the catalytic reduction of o-nitropyridine
(Table 2, Entry 17). Extension of this protocol to nitro-
substituted heterocycles was also successful, providing the
desired product o-aminopyridine in 74% yield.
It is well known that the catalytic of NiO@PolyMo
nanoparticle significantly depends on the sizes. Hence,
increasing the size of NiO@PolyMo leads to decrease in
catalytic performance for reduction of nitroarenes. These
same experiments were applied, when the model reaction
was done in the presence of Ni@bulk under identical
reaction conditions (Table 1, Entry 17). Catalytic
reduction of nitroarenes using nickel nanoparticles as
a catalyst has been widely used. Such reduction of
nitroarenes to corresponding amines is unique
straightforward reactions. However, using the newly
synthesized catalyst NiO@PolyMo, we have success-
fully isolated its corresponding aniline compounds in
good yield. Moreover, the catalyst can be recovered
easily, without any loss of the catalytic performance in
the next cycles. Similarly, the observations were also
quantified by spectrophotometric analysis, which showed
decrease of the characteristic absorption band of p-
nitrophenol (λmax = 401 nm) and a simultaneous increase
of the characteristic absorbance of p-aminophenol
(λmax = 294–311 nm) as shown in Figure S18.
2.3 | Proposed mechanism
To gain insight into the reaction mechanism, a suggested
reaction pathway for the catalytic reduction of nitroarenes
to corresponding aromatic amines using NiO@PolyMo cat-
alyst with NaBH4 as hydrogen source is shown in Scheme 3.

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7
SCHEME 3 Proposed mechanistic
pathway for reduction of nitroarenes
using NiO@PolyMo nanocatalyst in the
presence of NaBH4
FIGURE 3 Recyclability of NiO@PolyMo nanocatalyst in hydrogenation of nitrobenzene
Based on the similar mechanism reported in the literature,
we proposed the following steps taking place in the forma-
tion of the products. The reduction of nitro compound
involved the transfer of electron from BH4− ions to the nitro
group through the catalyst. In the initial step, the H−
absorbed in the surface of the catalyst, and it was then
transferred to the rich oxygen atom of the nitro group. In
the next step, it involved the removal of water molecule,
and nucleophilic attack of H− to the electron-deficient nitro-
gen atom, resulting in the formation of N-(4-iodophenyl)
hydroxylamine. In the final step, transfer of H− to the nitro-
gen atom and elimination of water molecule which results
in the formation of p-iodoaniline takes place.
nanocatalyst was then subjected for further use in the next
cycles. These results show that the cycles proceeded
with neither deactivation of the NiO@PolyMo nano-
catalyst nor a reduction in selectivity. The TEM image of
NiO@PolyMo nanocatalyst after five consecutive cycles
shows no alteration on the structure morphology and no
particles aggregation of NiO@PolyMo occurred.
3 | EXPERIMENTAL SECTION
3.1 | Chemicals and instruments
It is worth mentioning that the catalyst can be
recovered, reused, and recycled. The recyclability of
NiO@PolyMo nanocatalyst was analyzed by per-
forming a series of five consecutive runs for the cata-
lytic studies for reduction of nitrobenzene (Figure 3).
The recycling experiments were performed by recovering
the catalyst by centrifugation, washing with ethyl acetate,
and drying at 70ꢀC for 5 hr. The recovered NiO@PolyMo
Solvents were reagent grade purchased from HiMedia,
Sigma Aldrich. Other chemicals such as nitrobenzene,
nickel nitrate hexahydrate (Ni(NO3)2Á6H2O, Sigma,
99.99%), sodium borohydride (NaBH4, Sigma, 99%),
ammonium heptamolybdate tetrahydrate (NH4)6Mo7O24,
Merk). All of the reagents were used as received, without
further processing or purification. XRD patterns of the
samples shown in Figure 1 were recorded in a Bruker D8

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Discover X-ray diffractometer, equipped with a LynxEye
detector, using an acrylic sample holder. The H NMR
ligand. The NiO@PolyMo nanocatalyst has been
tested for the catalytic hydrogenation of nitroarenes.
The advantages of the present protocols are mild, and
were carried out using water as a solvent, which is an
eco-friendly benign. It can be concluded that the synthe-
sized NiO@PolyMo nanomaterial shows an outstanding
performance in the catalytic reduction of nitro aromatic to
their corresponding amine compounds. This process aims
toward the development of a sustainable chemical process
for the catalytic reduction of nitro compounds. Focusing on
the whole process involved, and the available literatures
report, NiO@PolyMo has been found to be a promising
candidate for catalytic reduction of nitro compounds to
amines.
1
and 13C NMR spectra were recorded on AMX-400 MHz
and 100 MHz in DMSO-d6 solution using tetra-
methylsilane as internal standard. The morphologies of
the NiO@PolyMo were characterized using a scanning
electron microscope (JSM-6360, Joel, with oxford EDS
detector) operating at 1–30 kV. For sample preparation,
diluted sample was put into the thin aluminum sheet by
using capillary tube and then allowing it to dry in air.
The sample was also coated with a thin layer of gold
before the experiment to minimize sample charging.
3.2 | Synthesis of NiO@PolyMo
ACKNOWLEDGMENTS
In a typical synthesis of NiO@PolyMo, fine nickel oxide
powdered (0.149 g, 2.0 mmol) was dispersed in deionized
water (50 ml) for 30 min. To this solution, poly-
oxomolybdate (2.47 g, 2.0 mmol) also stirred in deionized
water (10 ml) was added, and stirred at room temperature.
The mixture was then heated at 100ꢀC to dryness for 2 hr.
Finally, the prepared NiO@PolyMo nanoparticle was
heated in a muffle furnace at the rate of 4ꢀC/min under air
conditions until reaching 400ꢀC and held at this tempera-
ture for 3 hr. The resulting gray black powder obtained was
finely ground into fine powder and kept for further use.
Sunshine Dominic Kurbah would like to thank Head
SAIF, North-Eastern Hill University, Shillong-793022,
India for providing TEM, EDX, 1H and 13C NMR spectra.
CONFLICT OF INTEREST
The authors declare no potential conflict of interest.
ORCID
Sunshine Dominic Kurbah https://orcid.org/0000-0001-
5029-3815
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How to cite this article: Kurbah SD.
Development of sustainable and efficient
nanocatalyst based on polyoxometalate/nickel
oxide nanocomposite: A simple and recyclable
catalyst for reduction of nitroaromatic compounds.
J Chin Chem Soc. 2021;1–9. https://doi.org/10.
1002/jccs.202100057