International Journal of Biological Macromolecules 239 (2023) 124135

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International Journal of Biological Macromolecules

journal homepage: www.elsevier.com/locate/ijbiomac

Review

Chitosan-supported metal nanocatalysts for the reduction of nitroaromatics

Changlei Xia a, Xin Jin a, Ahmad Parandoust b, Reza Sheibani c, *, Zahra Khorsandi d,
Narjes Montazeri e, Yingji Wu a, Quyet Van Le f
a
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of
Materials Science and Engineering, Nanjing Forestry University, Nanjing, Jiangsu 210037, China
b
Farabi Educational Institute, Moghadas Ardebili St., Mahmoodiye St., No 13, 1986743413 Tehran, Iran
c
Amirkabir University of Technology-Mahshahr Campus, University St., Nahiyeh san’ati, Mahshahr, Khouzestan, Iran
d
Department of Chemistry, Isfahan University of Technology, Isfahan 415683111, Iran
e
Department of Chemical Engineering, Science and Research Branch, Islamic Azad University, Tehran, Iran
f
Department of Materials Science and Engineering, Institute of Green Manufacturing Technology, Korea University, 145, Anam-ro, Seongbuk-gu, Seoul 02841, Republic
of Korea

A R T I C L E I N F O A B S T R A C T

Keywords: The second most abundant natural polymer in the earth’s crust is chitosan (CS). The unique physical, chemical,
Reduction structural, and mechanical features of this natural polymer have led to its increased application in a variety of
4-Nitrophenol fields such as medicine, catalysis, removal of pollutants, etc. To eliminate various pollutants, it is preferable to
Environmental applications
employ natural compounds as their use aids the removal of contaminants from the environment. Consequently,
Chitosan-supported metal nanoparticles
Nitroaromatics
employing CS to eliminate contaminants is a viable choice. For this aim, CS can be applied as a template and
support for metal nanoparticles (MNPs) and prevent the accumulation of MNPs as well as a reducing and sta­
bilizing agent for the synthesis of MNPs. Among the pollutants present in nature, nitro compounds are an
important and wide category of biological pollutants. 4-Nitrophenol (4-NP) is one of the nitro pollutants. There
are different ways for the removal of 4-NP, but the best and most effective method for this purpose is the
application of a metallic catalyst and a reducing agent. In this review, we report the recent developments
regarding CS-supported metallic (nano)catalysts for the reduction of nitroaromatics such as nitrophenols,
nitroaniline compounds, nitrobenzene, etc. in the presence of reducing agents. The metals investigated in this
study include Ag, Au, Ni, Cu, Ru, Pt, Pd, etc.

1. Introduction with homogenous catalysts [51–63]. Nanocatalysts have wide applica­

Nanomaterials have been attracting the attention of many re­
searchers because of their size, affinity, high stability, and selectivity
[1–10]. They have unique chemical and physical properties due to their
high surface area and nanoscale size and can be classified into different
classes based on their properties, shapes or sizes [11–20]. They are
suitable candidates for various applications such as catalysis, energy-
based research, medicine, imaging, and environmental protection
[21–40]. The development of catalytic systems to achieve better reac­
tion performance has become a hot topic in the field of catalysis
[41–50]. Among nanomaterials, nanocomposite-based metal nano­
particles (MNPs) show considerable catalytic activities [40]. Nano­
composites have exhibited more efficiency in terms of catalytic activity
in comparison with bulk compounds and better reusability compared
tions in different fields such as the synthesis of important organic
compounds, electrochemistry, and removal of environmental contami­
nants [64–74].
In recent years, water pollution has been one of the significant
concerns in the world because the health of all living beings such as
humans, animals, and plants depends on it. In addition, water pollution
has important effects on the development of agriculture and economy. In
fact, the mechanization of human life and the development of various
factories and industries cause pollution in the environment and water
[75–77]. There are various pollutants in water including organic dyes,
nitroaromatic compounds, heavy metals, bacteria, fungi, etc. [78–82].
Among these, nitroaromatic compounds (NitACs) are hazardous con­
taminants owing to their carcinogenicity, non-biodegradability, and
high toxicity. NitACs are aromatic compounds with one or more nitro

* Corresponding author.
E-mail address: rsheibani2003@gmail.com (R. Sheibani).

https://doi.org/10.1016/j.ijbiomac.2023.124135
Received 8 December 2022; Received in revised form 17 March 2023; Accepted 19 March 2023
Available online 23 March 2023
0141-8130/© 2023 Elsevier B.V. All rights reserved.
C. Xia et al.
Fig. 1. Different types of NitACs.
functional groups (Fig. 1), which are widely used for different applica­
tions such as fabrication of explosives, polymers, dyes, pesticides, and
other intermediates [83–85].
The release of these NitACs from various industries along with
improper disposal of wastes causes serious pollution to the environment.
NitACs are continually discharged into the environment and water,
which is dangerous for humans and other living beings [86,87]. Almost
all NitACs are known mutagenic and carcinogenic agents for humans
and as a result, cause serious problems for human health. For instance,
nitrobenzene (NB) is one of NitACs, which leads to some health prob­
lems such as liver damage, methemoglobinemia, hepatic toxicity, and
anemia [88–91]. Other NitACs are nitropyrenes (NP) including dini­
tropyrenes and mononitropyrenes, which are highly carcinogenic and
mutagenic agents [92]. In addition, 2,4,6-trinitrotoluene (2,4,6-TNT),
which is an explosive compound, causes cytotoxic effects on the spleen
and liver [93]. Moreover, TNT and its derivatives can form hemoglobin
adducts, which result in genotoxicity and possible carcinogenicity [93].
As a result, due to the toxicity of NitACs, they must be removed from the
environment and waters. There are several methods for the removal of
NitACs from water including adsorption, sonolysis, radiolysis, catalytic
reduction, etc. [93–97].
Today, catalytic reduction is very important because various amine
derivatives are prepared by reducing NitACs. Meanwhile, the use of
heterogeneous catalysts, which contain different metals such as Cu, Pt,
Pd, Ag, etc. is an effective method. Among different types of catalysts,
heterogeneous catalysts are very efficient in the reduction of NitACs
owing to their clean handling, high efficiency, easy process, and eco­
nomic nature [98–102]. Consequently, the appropriate design of het­
erogeneous catalysts and their precise choice can significantly improve
the reduction process. With the growing requirement for greener cata­
lytic systems, the development of eco-friendly processes, which could be
preferably carried out in an aqueous environment, is highly desired.
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International Journal of Biological Macromolecules 239 (2023) 124135
Nowadays, different catalytic reduction processes have been developed
using volatile and toxic solvents and reducing agents such as NaBH4,
which has several advantages including water solubility and different
features as an alternative hydrogen source [103,104]. In this regard, CS-
supported metallic (nano)catalysts are appropriate choices for the cat­
alytic reduction of NitACs [104].
The application of biopolymers as appropriate supports to prepare
different catalysts has recently attracted much consideration. In fact,
these natural polymers can be applied as efficient supports and reducing
and stabilizing agents for different reactions. Among biopolymers,
polysaccharides, which include cellulose, pectin, alginate, starch, gum,
chitin, and CS, are a large class of natural polymers [105–112]. Among
these, CS is currently of special importance due to its many advantages
such as biodegradability, non-toxicity and availability, as well as con­
taining –NH2 and –OH functional groups [113–116]. CS is a liner
biopolymer with glucosamine units, which is produced from chitin
deacetylation. The source of chitin is the exoskeleton of lobsters, crabs,
and shrimps (Fig. 2). One of the important features of CS for making
catalysts is that it is capable of absorbing transition metals, and as a
result, it can be used to make heterogeneous catalysts containing metals.
In addition, CS has useful functional groups in its structure, which makes
it a suitable substrate for making heterogeneous catalysts [117–120]. In
this paper, the recent studies concerning CS-supported metallic (nano)
catalysts for the reduction of NitACs have been reviewed.
2. CS-supported metallic (nano)catalysts
CS is insoluble in most solvents and water. Therefore, it can be used
as a heterogeneous catalyst for different transformations. The presence
of free –NH2 and –OH groups on CS allows its coordination with
different metals (ions or nanoparticles) and makes it an attractive nat­
ural polymeric support for the decoration of metals such as Pd, Cu, Ag,
C. Xia et al.
Fig. 2. The source of chitin and the chemical structure of the chitin and CS.
Pt, Au, Ru, Ni, etc. [121–128]. In this section, we report previous studies
on the application of CS-supported metallic (nano)catalysts for the
reduction of NitACs.
2.1. CS-supported Ag (nano)catalysts
Murugadoss and Chattopadhyay reported a facile procedure to pre­
pare CS-Ag NPs composite, which can be effectively used in the reduc­
tion of 4-NP in the presence of excess NaBH4 in H2O with TOF of (1.5 ±
0.3) × 10− 3 s− 1 [129]. In this polymeric composite, chitosan acts as a
reducing and stabilizing agent for metal ions and the synthesis of Ag
NPs. In another study in 2014, a green and efficient technique for the
synthesis of Ag NPs by CS was reported by Venkatesham et al. [130]. The
bare Ag NPs prepared were highly stable in the reaction and their cat­
alytic prowess led to the reduction of 4-NP to 4-aminophenol (4-AP). In
the same year, Zhai and co-workers synthesized Ag NPs onto a magnetic
core-shell (Fe3O4@SN/HPW@CG-Ag), as shown in Fig. 3 [131]. The as-
synthesized catalyst exhibited high catalytic performance for 4-NP
reduction using NaBH4 within 7 min.
In 2015, Ling et al. reported the synthesis of chitosan/rectorite/Ag
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International Journal of Biological Macromolecules 239 (2023) 124135
NP nanocomposite (QCRAg) via microwave radiation using quaternized
CS (QCS) and rectorite (REC), which acted as reducing and stabilizing
agents, respectively [132]. The as-prepared nanocomposite was in the
form a film and used for 4-NP reduction by NaBH4 (Fig. 4). The nanofilm
showed great catalytic performance with considerable recyclability even
after 10 cycles.
In 2015, Kumar and colleagues prepared chitosan functionalized
graphene oxide decorated with Ag/Au NPs (GO-CS-Ag/AuNPs) using a
facile approach via anchoring Au and Ag NPs on GO-CS in the presence
of NaBH4 (Fig. 5) [133]. The GO-CS-Ag/AuNPs nanocatalysts were used
for the reduction of nitroarene by NaBH4 with 100 % conversion in most
of the cases.
In 2016, Alshehri et al. introduced a simple method to prepare a
novel nanocatalyst for 4-NP reduction (Fig. 6) [134]. This polymer
composite was successfully prepared using carboxyl group-
functionalized multi-walled carbon nanotubes (MWCNTs-COOH), Ag
NPs, and a chitosan-based polymeric matrix. The Ag NPs with an
average diameter of 3 nm were prepared via silver nitrate reduction by
trisodium citrate in MWCNTs-polymer nanocomposite. The as-prepared
Ag@MWCNTs-polymer composite showed stability to Ag NPs in the
C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 3. Synthesis of Fe3O4@SN/HPW@CG-Ag and its application for 4-NP reduction [131] with permission of RSC Copyright © (2014).

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C. Xia et al.
Fig. 4. Possible mechanism for 4-NP reduction by QCRAg nanocomposite [132] with permission of Elsevier Copyright © (2015).
environment and the reaction medium. The nanocomposite could be
reused in several catalytic cycles.
In 2017, a simple, safe, and inexpensive method to synthesize Ag NPs
deposited CS microcapsules with Fe3O4 cores was reported by Xu and
colleagues (Fig. 7) [135]. The microcapsules obtained were utilized as a
powerful and efficient catalyst for 4-NP reduction with 98 % conversion
within 15 min. The Fe3O4/CS-Ag nanocatalyst could be easily separated
from the reaction medium and maintained excellent activity after ten
runs.
In 2017, Ahmad et al. reported the synthesis of Ag NPs impregnated
porous CS beads [136]. The as-synthesized catalyst was used in 4-NP
reduction by NaBH4. In 2018, Xiao and colleagues prepared dispersed
quasi-spherical Ag NPs on CS-TiO2 composite via bioaffinity adsorption-
photocatalysis in a photocatalytic reactor (Fig. 8) [137]. The produced
recyclable nanocatalyst showed efficient catalytic activity in 4-NP
reduction and led to 100 % conversion in 2 h. The catalytic prowess of
the nanocatalyst was constant for five runs.
In 2018, reduced graphene oxide (RGO) was decorated with Ag NPs
for antibacterial properties and catalytic reduction tests by An and co-
workers via a facile solution-based method in CS solution (Fig. 9)
[138]. Ag/RGO/CS nanocomposite showed significant catalytic prowess
in 4-NP reduction by NaBH4.
In 2018, Ali and co-workers reported the synthesis of supported
metal MNPs by treating chitosan-silica (CS-SiO2) fiber with metal salt
solution and NaBH4 (Fig. 10) [139]. The catalytic activity of CS-SiO2
templated with Ag, Co, Ni, and Cu was examined for 4-nitroaniline (4-
NA) reduction. Among these nanocomposites, Cu/CS-SiO2 showed great
catalytic activity.
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International Journal of Biological Macromolecules 239 (2023) 124135
In 2019, Alshehri and his research group prepared highly porous Ag
NPs embedded in N-doped carbon derived from CS-based hydrogel (Ag/
N-C) (Fig. 11) [140]. Ag/N-C nanocomposite was used for 4-NP reduc­
tion under visible light (Fig. 12). 98 % of 4-NP was reduced to 4-AP and
the catalyst could be reused in seven successive cycles.
Murugave et al. introduced a synthetic method to prepare Fe3O4@C­
S_AgNi composite via dispersing AgNi bimetallic NPs on Fe3O4@CS
(Fig. 13) [141]. The as-prepared catalyst showed excellent catalytic
prowess for the reduction of different NitACs and led to 100 % conversion
and selectivity in most cases. This reusable catalytic system was stable and
reusable for several runs with no reduction of catalytic activity.
Laghrib et al. carried out the synthesis of CS-stabilized silver NPs on
the carbon paste electrode (CS-SNPs/CPE) in 2019 (Scheme 1) [142].
The electrochemical performance of CS-SNPs/CPE was examined in the
reduction of p-nitroaniline (p-NA). The results revealed a detection limit
of 5.0 nM in the range of 7 nM-1 μM.
In the same year, the same group synthesized chitosan-stabilized Ag
NPs on the carbon paste electrode (CS-Ag NPs/CPE) using NaBH4
(Scheme 2) [143]. They investigated the electro-catalytic reduction of 4-
NA using CS-Ag NPs/CPE. The results revealed a detection limit of 0.86
μM with 4-NA concentration in the range of 1 μM-0.5 mM.
In 2019, a simple process was reported by Sargin for the synthesis of
Ag(0)@chitosan gel beads via the immobilization of Ag particles on
glutaraldehyde cross-linked CS gel beads under thermal conditions
[144]. The Ag(0)@CS gel beads exhibited considerable catalytic activity
in the reduction of nitroaromatics (Scheme 3). This catalyst was sepa­
rated and reused for three runs without any considerable decrease in the
catalytic performance.
C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 5. Synthesis of GO-CS-Ag/AuNPs.

Reprinted from ref. [133] with permission of RSC Copyright © (2015).

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Fig. 6. Schematic representation of the synthesis of Ag@MWCNTs-polymer composite and its application for 4-NP reduction [134] with permission of Elsevier
Copyright © (2016).

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C. Xia et al.
Fig. 7. Synthesis and application of Fe3O4/CS-Ag for 4-NP reduction [135] with permission of Elsevier Copyright © (2017).
Fig. 8. Synthesis of Ag NPs@CS-TiO2 composite.
Reprinted from ref. [131] with permission of RSC Copyright © (2014).
Makaudi et al. reported the synthesis of Ag NPs@chitosan-
functionalized graphene oxide (Ag NPs@GO-FL-CS) catalyst in 2021
(Scheme 4) [145]. The synthesized Ag NPs@GO-FL-CS catalyst was
studied in the reduction of 2,4-dinitrophenol (2,4-DNP) (Scheme 5). It
was shown that the catalytic performance of the catalyst remained
constant after at least six cycles.
In 2022, Balram et al. successfully synthesized Ag NPs anchored
Co3O4 nanoflowers and CS functionalized carbon nanofibers (Ag-Co3O4
NFs/CS-CNFs) using a sonochemical approach (Fig. 14) [146]. The
electrocatalytic prowess of Ag-Co3O4 NFs/CS-CNFs porous nano­
composite was studied in the detection and degradation of 4-NP in un­
derground water, domestic sewage, and tomato.
2.2. CS-supported Au (nano)catalysts
Green methods for the reduction of various metals in the absence of
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International Journal of Biological Macromolecules 239 (2023) 124135
dangerous chemical compounds are very important in chemistry. In
2009, Chang and Chen reported the formation of Au NPs via the
adsorption of ions on CS surface coated on iron oxide NPs (Fig. 15)
[147]. The catalytic activity of nanocomposite was investigated and the
results showed great activity for 4-NP reduction.
In 2014, Hu et al. synthesized core-satellites nanostructural
magnetic-Au NPs composite (Fe3O4@C16@CS-Au NPs nano-composites)
via self-assembly combined with in-situ growth process including func­
tionalization of Fe3O4 NPs with C16 by adding hexadecyltrimethox­
ysilance, coating CS on Fe3O4@C16 via ionotropic gelation, and
decoration of Au NPs on Fe3O4@C16@CS (Fig. 16) [148]. The obtained
nanostructure had an active and stable surface for 4-NP reduction. The
catalytic activity of the composite did not change even after 11 runs.
In 2012, Ma and colleagues reported an environmentally friendly
and efficient method for the modification of 3D graphene nanosheets
using CS and Au nanostructures (3DG@CS@AuNSs) (Fig. 17) [149].
C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 9. Synthesis of Ag/RGO/CS nanocomposite and its application for 4-NP reduction [138] with permission of Wiley Copyright © (2018).

3DG@CS@AuNSs displayed high activity in 4-NP reduction.

Fig. 10. Production of MNPs templated on CS-SiO2 nano-fiber [139] with
permission of Elsevier Copyright © (2018).
Eisa et al. reported a simple method for the synthesis of CS/Au NPs
nanocomposite film [150]. The mean diameter and size distribution of
Au NPs were 7–27 and 14 nm, respectively. The Cs/Au nano-film
showed high catalytic activity in 4-NP reduction. Moreover, this nano-
film was easily separated and reused three times. CS modified with
different activators provided a suitable and active surface for the
deposition of various MNPs. In 2019, Fu and co-workers reported a
green method for the functionalization of CS by activated coke (AC) as a
platform for Au NP anchoring (Fig. 18) [151]. The Au NPs/CS/AC
nanocatalyst showed high catalytic activity in the hydrogenation of
nitrophenols with good recyclability.
In another study, a simple and environmentally friendly method to
prepare CS‑gold bionanocomposite without using reducing agents was
reported by Bonardd et al. (Scheme 6) [152]. The prepared bio-
nanocatalyst was used as a heterogeneous composite for 4-NP reduc­
tion. The catalytic activity increased as Au NPs content in the bio­
nanocomposite increased.

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C. Xia et al.
Fig. 11. Fabrication of Ag/N-C.
Reprinted from ref. [140] with permission of Elsevier Copyright © (2019).
Fig. 12. A possible mechanism for 4-NP reduction by Ag/N-C nanocomposite
[140] with permission of Elsevier Copyright © (2019).
2.3. CS-supported Ni (nano)catalysts
In 2014, Yang et al. reported the synthesis of Ni-based mesoporous
carbon through CTAB-chitosan-Ni supramolecular aggregates (Fig. 19)
[153]. The prepared composite showed high activity for 4-NP reduction.
In 2017, Karakas et al. synthesized Ni(0) NPs on the surface of
electrospun polymeric (polycaprolactone(PCL)/CS) nanofibers and
produced Ni-NP/ENF nanocatalyst for the reduction of 2-NP, 2,4-DNP,
and 2,4,6-TNP at room temperature (Fig. 20) [154]. The results indi­
cated that Ni-NP/ENF nanocatalyst could reduce nitro compounds in the
presence of NaBH4 and showed high activity and reusability.
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International Journal of Biological Macromolecules 239 (2023) 124135
In 2017, Pal et al. reported the synthesis of POSTCS beads [155]. As
shown in Fig. 21, Ni(II) was overloaded on the POSTCS beads through
adsolubilization. Afterward, Ni@NiO core-shell particles were produced
by the addition of NaBH4. According to the results, nickel loading in
POSTCS beads was ~4 times higher compared to CS beads. The catalyst
showed outstanding catalytic prowess for 4-NP reduction.
2.4. CS-supported Cu (nano)catalysts
In 2017, Souza et al. introduced a process for the synthesis of chi­
tosan/poly(vinyl alcohol)-based film supported Cu NPs (CP-Cu)
(Fig. 22) using an eco-friendly method [156]. The catalytic prowess of
CP-Cu film was investigated in the reduction of NB. This novel catalytic
system showed high catalytic activity with constant efficiency even after
6 consecutive cycles.
In 2019, Guo and co-workers prepared chitosan-modified Cu2O NPs
(Cu2O-CS) by a facile chemical reduction procedure [157]. The catalytic
activity of Cu2O-CS was investigated in 4-NP reduction. In this study, the
TEM images of Cu2O and Cu2O-CS were used to characterize the
morphology of these compounds. According to Fig. 23, Cu2O NPs
generally exist in spherical and cubic shapes and are irregularly formed.
The results indicated that Cu2O-CS nanocomposite was merely cubic-
like in shape. The limited morphology of Cu2O-CS is assumed to be
the influence of chitosan on the growth process of Cu2O.
In 2019, chitosan-graphene oxide (CS + GO) nanocomposite fibers
were fabricated and Cu NPs were grown on them via treatment with
NaBH4 and CuSO4⋅5H2O solution (Fig. 24) [158]. Cu@CS + GO was
applied as an economic catalyst for 4-NP detection (high sensitivity:
1.729 ± 0.027 μAmM− 1 cm− 2) and reduction (high rate constant: (1.310
± 0.093 min− 1) and showed high stability and reusability.
Bakhsh et al. reported the synthesis of copper NPs embedded in CS
[159]. The CuNPs-CS were studied in the reduction of 4-NA. The results
indicated high catalytic activity of CuNPs-CS to produce dia­
minobenzene in a short time.
C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 13. Schematic representation of the production of Fe3O4@CS and Fe3O4@CS-AgNi nanocatalyst.
Reprinted from ref. [141] with permission of ACS Copyright © (2019).

Scheme 1. Schematic representation of the synthesis of CS-SNPs/CPE for the reduction p-NA [142] with permission of Elsevier Copyright © (2019).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Scheme 2. The formation mechanism of CS-Ag NPs [143] with permission of Elsevier Copyright © (2019).

Scheme 3. Ag(0)@CS gel beads catalyzed the reduction of NitACs [144] with permission of Elsevier Copyright © (2019).

Scheme 4. Synthesis of Ag NPs@GO-FL-CS [145].

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

The catalyst could be efficiency reused four times.

2.5. CS-supported Ru (nano)catalysts

In 2017, Liew et al. reported the fabrication of magnetic CS

(Mn@CS), followed by the deposition of ruthenium NPs on Fe3O4@CS
surface (Mn@CS@Ru) (Fig. 27) [163]. Mn@CS@Ru catalyst showed
excellent performance in 4-NP and 4-NA reduction with considerable
TOF (273.9 and 336.5 min− 1, respectively) (Fig. 28). Moreover, the
catalyst was recovered simply and efficiency reused for 10 cycles.

2.6. Chitosan-supported Pt and Pd (nano)catalysts

Jouannin et al. reported the fabrication of CS-supported phospho­

Scheme 5. A plausible mechanism for Ag NPs@GO-FL-CS-catalyzed reduction nium-based ionic liquids and Pd HPMs (highly porous monoliths) [164].
of 2,4-DNP with NaBH4 [145]. These compounds showed significant catalytic prowess in the hydro­
genation of 4-NA in the presence of formic acid.
In 2017, Zhang et al. reported the fabrication of cross-linked CS
polymer via Schiff reaction of CS by terephthalic aldehyde (TPA), fol­
lowed by modification using trimethoxysilylpropanethiol (SH) (Fig. 29)
Arora et al. reported the synthesis of organoselenium ligand-
[165]. This compound could act as a support and stabilizer agent for
stabilized copper NPs and their immobilization on CS-layered mag­
Pd2+ particles. The achieved Pd/CS-TPA-SH catalyst showed high ac­
netic support in 2021 (Fig. 25) [160]. They investigated the catalytic
tivity and recyclability in 4-NP reduction.
activity of the prepared magnetic catalyst in the reduction of nitroarene
In 2018, Liang et al. synthesized cross-linked CS superfine fiber with
(Scheme 7).
a diameter of 321 ± 99 nm using a facile and suitable method via
Baranwal et al. reported the successful CS-mediated fabrication of
electrospinning with itaconic acid (IA) and polyethylene oxide (PEO) as
Cu-doped NiO NPs with a size of ~12 nm via the wet chemical method
the in-situ cross-linking agent and co-spinning polymer, respectively
[161]. The prepared catalyst was employed efficiently in the reduction
(Scheme 8) [166]. Afterward, Pd NPs were decorated on the cross-linked
of 4-NP, 4-nitrobenzoic acid (4-NBA), and 4-NA within 1.66, 5, and 4
CS/PEO/IA composite fibers with a large surface area. This modified
min, respectively.
fiber (Pd-CS/PEO/IA) exhibited high catalytic activity for the reduction
In 2021, Ali et al. reported the synthesis of Fe and Cu NPs and their
of 4-NP in an aqueous medium with nearly 100 % conversion. Pd-CS/
immobilization on the eggshell membranes coated CS (ESM-CS)
PEO/IA catalyst could be efficiency reused in five runs.
(Fig. 26) [162]. They investigated MNPs@ESM-CS catalytic prowess for
In 2018, Berillo and Cundy synthesized stable 3D-macroporous CS-
the reduction of 4-NA, 4-NP, and methylene blue (MB) within 6–7 min.
based scaffolds (cryogels) with incorporated Pd and Pt NPs (Fig. 30)

Fig. 14. Schematic representation of the fabrication of Ag-Co3O4 NFs/CS-CNFs modified screen-printed carbon electrode (SPCE) for 4-NP detection.
Reprinted from ref. [146] with permission of Elsevier Copyright © (2022).

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Fig. 15. Schematic representation of the production of reusable Au catalyst and its application for 4-NP reduction [147] with permission of Elsevier Copyright
© (2009).

Fig. 16. Schematic representation of the preparation of Fe3O4@C16@CS-Au NPs(G) [148] with permission of Elsevier Copyright © (2014).

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C. Xia et al.
Fig. 17. Synthesis of 3DG@CS@AuNSs and catalytic reduction property [149] with permission of RSC Copyright © (2015).
[167]. The macroporous compound was synthesized via the in-situ
fabrication of Pt and Pd NPs incorporated into the cryogel walls using
glutaraldehyde for the reduction of Pd or Pt complexes to form Pd and Pt
NPs, respectively. The catalytic activity of the 3D-macroporous was
investigated in 4-NP reduction. The TON and TOF values using 2.66,
13.3, and 21 μg of incorporated Pd NPs were 10.24 & 0.529, 4.34 &
0.206, and 6.22 & 0.285 h− 1, respectively.
In 2019, Baran and Nasrollahzadeh prepared Pd NPs stabilized on
magnetically separable CS/agar micro beads (Pd NPs@Fe3O4/CS-AG
microcapsules) (Fig. 31) [168]. The catalytic activity of the microcap­
sules obtained was studied in 4-NP reduction in a very short time. Pd
NPs@Fe3O4/CS-AG showed high catalytic activity and could be easily
separated and reused in ten consecutive runs.
In 2019, an efficient process for the fabrication of Pd and Fe3O4 NPs
supported on a novel biocompatible hybrid composed of CS, GO, and
ionic liquid decorated cyclodextrin nanosponge (CDNS-IL) was reported
by Sadjadi et al. (Scheme 9) [169]. This catalyst (Fe3O4/Pd@Hybrid)
exhibited considerable activity and stability in the hydrogenation of
nitro compounds.
In 2019, Sarvestani and Azadi prepared chitosan-functionalized
graphene oxide for the immobilization of Pd NPs (GO-CS-Pd) and used
it for the reduction of various nitroarenes under aqueous conditions
(Scheme 10) [170]. This catalyst could be easily separated and reused in
five consecutive cycles.
Sargin et al. reported CS‑carbon nanotube-supported palladium NPs
(Scheme 11) as an efficient catalyst for the reduction of nitroarenes
[171]. Pd NPs@CS-MWCNT showed excellent activity in the hydroge­
nation of 4-NP, 2-nitroaniline (2-NA), 4-nitro-o-phenylenediamine (4-
NPD), and 2,4-dinitrophenol using NaBH4 at room temperature within
1.5–12 min.
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International Journal of Biological Macromolecules 239 (2023) 124135
Hamzavi et al. reported a process for preparing Pt NPs on proline-
functionalized cross-linked CS particles in 2020 [172]. The prepared
Pt-immobilized CS (Pt/PCS) was used as a catalyst in the reduction of
nitrobenzene derivatives using NaBH4 (Scheme 12).
Esmaeilzadeh et al. reported a process for preparing Pd decorated on
magnetic graphene quantum dots incorporated in cyclodextrin-
decorated CS in 2020 (Fig. 32) [173]. The prepared Pd@CS-CD-
MGQDs was employed in the hydrogenation of NitACs in aqueous
media.
In 2020, Ge et al. reported the fabrication of CS/GA/RGO/Pd com­
posite hydrogel via loading Pd NPs on CS/RGO-based composite
hydrogel prepared by glutaraldehyde (GA) [174]. They observed that
CS/GA/RGO/Pd catalyst showed excellent activity in the reduction of 2-
NA and 4-NP using NaBH4 for 28 and 64 min, respectively.
Kalanpour et al. reported the fabrication of Pd NPs/graphene
quantum dots supported on chitosan (Pd/GQD-Chitosan) in 2021 [175].
Pd/GQD-chitosan was prepared according to Scheme 13 and used as an
efficient catalyst in the reduction of nitroarenes by NaBH4 in water
(Scheme 14).
Baran and Nasrollahzadeh reported that Pd/CoFe2O4/CS beads could
act as an effective and active hybrid nanocatalyst for the reduction of 2-
NA in 65 s [176]. Pd/CoFe2O4/CS hybrid nanocatalyst was prepared via
the immobilization of Pd NPs on CoFe2O4/CS as a stabilizer (Scheme
15). The catalyst could be easily recovered and efficiently used several
times.
Baran et al. reported the immobilization of Pd(0) on micro-sized CS-
g-C3N4 hybrid spheres in 2021 (Scheme 16) [177]. The prepared Pd-CS-
g-C3N4 nanocatalyst was utilized in the reduction of nitroarenes and
dyes using NaBH4 within very short reaction times.
Pei et al. reported the fabrication of Pd catalyst on nanoporous CS for
C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 18. Schematic representation of the synthesis of Au NPs/CS/AC and its application in the hydrogenation of nitrophenols [151] with permission of Elsevier
Copyright © (2019).

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Scheme 6. Schematic representation of the preparation of CS-Au NPs [152] with permission of Elsevier Copyright © (2019).

Fig. 19. Schematic representation of the synthesis of Ni-based mesoporous carbon [153] with permission of RSC Copyright © (2014).

Fig. 20. Schematic representation of the preparation of Ni-NP/ENF and its application in the reduction of nitrophenols [154] with permission of Elsevier Copyright
© (2017).
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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 21. Schematic representation of synthesis of Ni-POSTCS [155] with permission of Elsevier Copyright © (2017).

Fig. 22. Schematic representation of the synthesis and catalytic activity of CP-Cu NPs [156] with permission of Elsevier Copyright © (2017).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 23. TEM images of a) Cu2O and b) Cu2O-CS.

Reprinted from ref. [157] with permission of Elsevier Copyright © (2019).

Fig. 24. Schematic representation of the preparation of Cu@CS + GO nano-fiber [158] with permission of Elsevier Copyright © (2019).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 25. Synthesis of ligand-stabilized Cu NPs on Fe3O4@CS surface.

Reprinted from ref. [160] with permission of Elsevier Copyright © (2021).

Scheme 7. Fe3O4@CS@L1-stabilized-Cu NPs-catalyzed nitroarenes reduction [160] with permission of Elsevier Copyright © (2021).

Fig. 26. Synthesis of MNPs@ESM-CS and its application for 4-NP reduction.
Reprinted from ref. [162] with permission of Elsevier Copyright © (2021).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 27. Fabrication of Mn@CS@Ru.

Reprinted from ref. [163] with permission of Wiley Copyright © (2017).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 28. A plausible mechanism for Mn@CS@Ru-catalyzed nitroarenes reduction with NaBH4.
Reprinted from ref. [163] with permission of Wiley Copyright © (2017).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 29. The catalytic activity of Pd/CS-TPA-SH [165] with permission of Springer Copyright © (2017).

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Scheme 8. Synthesis of Pd-CS/PEO/IA fibers for 4-NP reduction [166] with permission of RSC Copyright © (2018).

Fig. 30. Schematic representation of biocatalytic and reduction activity.

Reprinted from ref. [167] with permission of Elsevier Copyright © (2018).

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Fig. 31. The schematic representation of production of Pd NPs@Fe3O4/CS-AG and its catalytic application [168] with permission of Elsevier Copyright © (2019).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Scheme 9. Schematic representation of the preparation of Fe3O4/Pd@Hybrid.

Reprinted from ref. [169] with permission of Elsevier Copyright © (2019).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Scheme 10. Fabrication of GO-CS-Pd and its catalytic activity [170] with permission of Canadian Science Publishing Copyright © (2019).

Scheme 11. Fabrication of Pd NPs@CS-MWCNT.

Reprinted from ref. [171] with permission of Elsevier Copyright © (2020).

27
C. Xia et al.
Scheme 12. Pt/PCS catalyzed the reduction of nitrobenzene derivatives [172] with permission of Springer Copyright © (2020).
the hydrogenation of nitroarenes [178]. Pd@CS catalyst showed high
catalytic activity, stability, and recyclability with no activity reduction
after 12 cycles (Scheme 17).
In 2022, Çalışkan and Baran developed a simple process for pre­
paring Pd NPs and their immobilization on CS/γMnO2 composite hybrid
microspheres [179]. The catalytic prowess of Pd/CS/γMnO2 was
investigated for the reduction of nitroarenes using NaBH4 at room
temperature within short reaction times (55–150 s).
2.7. CS-supported other metallic (nano)catalysts
Han et al. reported the fabrication of Cu, Zn, Ni, and Cr complexes of
silica-supported CS (Scheme 18) [180]. The catalytic prowess of the
complexes was examined in the hydrogenation of aromatic nitro com­
pounds (Scheme 18).
In 2014, Lu et al. reported the fabrication of CS-stabilized nano zero-
valent iron (CNZVI) [181]. This composite was used as a catalyst for 4-
NP reduction with the rate constant of 2.45 × 10− 3 s− 1. Furthermore, the
reusability of CNZVI was also studied. The catalyst could be easily
separated and reused in at least 5 successive cycles.
In 2017, Chen et al. reported the fabrication of chitosan-crafted ZnO
nanoneedle (CHT/ZnO NDs) modified screen printed carbon electrode
(SPCE) (Fig. 33). CHT/ZnO/SPCE showed good electrocatalytic activity
in the determination of 4-NP [182].
In 2017, Ai et al. prepared a novel and stable nanocomposite based
on the chitosan non-covalently functionalized oxidized CNT immobi­
lized iron and bismuth oxides (oCNT-chitosan-xFe2O3.yBi2O3) for the
reduction of nitroaromatics (Fig. 34) [183]. The oCNT-chirosan-xFe2O3.
yBi2O3 nanocomposite showed outstanding efficiency and great che­
moselectivity towards various nitro-compounds with >99 % conversion
using hydrazine hydrate as a reductant.
In 2021, Anusuya et al. reported the fabrication of TiO2/ZnO@CS
composite via the green thermal treatment of TiO2, ZnO, and CS acetic
acid solution in ethanol [184]. They investigated the catalytic prowess
of TiO2/ZnO@CS obtained in the hydrogenation of 2-NA and 1-nitro­
benzene in water (Scheme 19). The best results were obtained at
45 ◦ C and the reduction was completed in 0.14–0.15 min. In another
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International Journal of Biological Macromolecules 239 (2023) 124135
study, Anusuya et al. reported the fabrication of CS/TiO2-Fe2O3 nano­
material via a modified colloidal processing method in 2021 [185]. They
investigated the catalytic prowess of CS/TiO2-Fe2O3 in 4-NP reduction
using NaBH4.
3. Summary and discussion
Biopolymers are environmentally friendly, biodegradable, green,
and non-toxic supports applied for the synthesis of heterogeneous cat­
alysts. In this review, the applications of CS-supported metal nano­
particles as heterogeneous catalysts in the reduction of nitroarenes have
been reviewed. For the convenience of readers, a number of articles
concerning the reduction of nitroarenes using CS-supported MNPs cat­
alysts are summarized in Table 1 while paying attention to the important
results and activity factors of the presented catalytic systems. The review
of these publications shows that there are no special rules or general
ways to theoretically predict the results of a catalytic reduction.
Commonly, the variations in the performance of the described catalysts
depend on the different reaction conditions such as solvent and catalyst
type, reducing agents, catalyst loading, and features such as production
methods, size, porosity, morphology, chemical structures, chemical
composition, specific surface area, loading of metal/metal oxide on the
catalyst surface, etc. According to Table 1 and the comparison of some
selected catalysts, it is important to note that this comparison depends
on the reaction conditions and follows no predictive rules.
4. Conclusion and future prospects
Today, one of the most important challenges is the environmental
issue. Given the development of industries, many pollutants, which are
harmful to all living beings such as humans, animals, and plants, and
especially lead to serious problems for human health, enter the envi­
ronment and waters. Among the toxic compounds in the environment,
nitroaromatic compounds (NitACs) are one of the most important types.
NitACs are dangerous compounds, which are usually present in water.
The important aim of the present review has been to provide a complete,
dependable reference for researchers in the field of the progress of CS-
C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 32. Synthesis of Pd@CS-CD-MGQDs.

Reprinted from ref. [173] with permission of Elsevier Copyright © (2020).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Scheme 13. Synthesis of Pd/GQD-Chitosan catalyst [169] with permission of Elsevier Copyright © (2019).

Scheme 14. Pd/GQD-Chitosan-catalyzed the reduction of nitroarenes [175] with permission of Springer Copyright © (2021).

supported metallic (nano)catalysts for significant reduction of NitACs.
In fact, this paper has reviewed the latest progresses on the different
metallic catalytic systems based on CS, to convert NitACs into useful
products, which are less damaging to the environment and all living
things. As mentioned, CS-based catalytic systems have been used
because CS has many advantages such as biodegradability, availability,
natural availability, and presence of useful functional groups in its
structure (–OH and –NH2), etc. In this review, different systems using
transition metals and metal oxides such as Ag, Ru, Ni, Cu, Pt, Pd,
bimetallic NPs, etc. decorated on CS support have been reported. In
addition, NitACs reduction by NaBH4 and different catalytic systems has
been reviewed. Based on the results reported, NitAC reduction using CS-
supported metallic (nano)catalysts has been assessed several times to
assure reproducibility. The mentioned catalytic systems have different
advantages including ease of separation, high catalytic performance,
and recyclability.
Although many studies have been performed in this field, there are
still some issues, which need to be further investigated in the future,
such as:

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Scheme 15. Fabrication of Pd/CoFe2O4/CS hybrid nanocatalyst [176] with permission of Elsevier Copyright © (2021).

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Scheme 16. Synthesis of Pd-CS-g-C3N4 catalyst.

Reprinted from ref. [177] with permission of Elsevier Copyright © (2021).

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Scheme 17. Pd@CS-catalyzed the reduction of nitroarenes [178] with permission of Elsevier Copyright © (2022).

Scheme 18. Metal complexes of silica-supported CS-catalyzed the hydrogenation of nitro compounds [180] with permission of Wiley Copyright © (1996).

Fig. 33. (a) Fabrication of CHT/ZnO NDs and (b) electrocatalytic activity of CHT/ZnO/SPCE for 4-NP determination.
Reprinted from ref. [182] with permission of Elsevier Copyright © (2017).

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C. Xia et al. International Journal of Biological Macromolecules 239 (2023) 124135

Fig. 34. Schematic representation of the fabrication of oCNT-chirosan-xFe2O3.yBi2O3 nanocomposite [183] with permission of Elsevier Copyright © (2017).

Scheme 19. Reduction of nitroarenes at different temperatures [185] with permission of Elsevier Copyright © (2021).

Table 1
Different CS-supported MNPs catalysts developed for the reduction of nitroarenes.
Entry CS-supported metal catalysts (amount) Size (nm) Reaction rate (s− 1) Reaction time (min) Recyclability (no. of cycles) Ref.

1 Ag@CS (10.0 mM) 25 1.5 × 10− 3 25 10 129

2 Ag@CS (10.0 mM) 15 – 50 – 130
3 Fe3O4@SN/HPW@CG-Ag (10.0 mM) 8 8.9 × 10− 3 7 10 131
4 CS/rectorite/AgNP 12 – 45 10 132
5 GO-CS-Ag/AuNPs 5 5.5 × 10− 3 50 – 133
6 Ag@MWCNTs-polymer 3 – 5 5 134
7 Fe3O4/CS-Ag (10.0 mM) 15 – 15 10 135
8 AgNPs@CS-TiO2 (50 nM) 130 11.67 × 10− 3 120 5 137
9 Ag/RGO/CS (50 mM) 20 4.27 × 10− 3 10 – 138
10 Ag/CS-SiO2 (10 mg) 29 6.17 × 10− 3 9 5 139
11 Ag/N-C (10.0 mM) 13 – 40 7 140
12 Fe3O4@CS-AgNi (10.0 mM) 20 3.7 × 10− 3 60 7 141
13 CS/AgNPs@carbon paste electrode 51 – 1 – 142
14 CS-Ag NPs/CPE 51.5 0.125 × 10− 3 – – 143
15 Ag(0)@CS beads (24 mg) – – 0.28 3 144
16 Ag NPs@GO-CS-FL (5 mg) 20–60 0.22 × 10− 3 30 7 145
17 Ag-Co3O4 NFs/CS-CNFs/SPCE (40 mg) 180 0.31 × 10− 3 135 5 146
18 Au/CS@MNPs (0.49 mg) 3.14 – 10 11 147
19 Fe3O4@CS-AuNPs (0.02 mg) 0.21 3.06 × 10− 2 – 11 148
20 3DG@CS@AuNSs (3.3 mM) 15 6.33 × 10− 3 5 10 149
21 CS/Au NPs (5 × 10− 5 M) 14 1.7 × 10− 3 40 3 150
(continued on next page)

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Table 1 (continued )
Entry CS-supported metal catalysts (amount) Size (nm) Reaction rate (s− 1) Reaction time (min) Recyclability (no. of cycles) Ref.

22 Au NPs/CS/AC (5 mg) 0.2 11.7 × 10− 3 7 6 151

23 CS/Au NPs (10.0 mM) 20 4.8 × 10− 3 – – 152
24 Ni-NP@polycaprolactone/CS (2 mg) 95 – 3 3 154
25 Ni-POSTCS (0.1 Mm) 100 6.33 × 10− 3 15 – 155
26 CP-Cu NPs (100 mg) 2.48 0.42 × 10− 3 60 6 156
27 Cu2O-CS – – 5 3 157
28 Cu@CS + GO (5 mg) 11.93 15.2 × 10− 3 6 4 158
29 CuNPs-CS 5 7.51 × 10− 3 3 4 159
30 Fe3O4@CS@L1-stabilized-CuNPs (1 mg) 5–7 5.8 × 10− 3 10 5 160
31 CS/Cu doped NiO NPs (3 mg) 12 0.22 × 10− 3 1.66 10 161
32 Cu@@CS-ESM 17.2 8.31 × 10− 1 6 4 162
33 Magnetic@CS@Ru (0.5 mg) 3.9 60 × 10− 3 1.17 10 163
34 CS-phosphonium-IL-Pd 1–3 5.83 × 10− 3 20 – 164
35 Pd/CS-TPA-SH (0.02 g) 12 – 1 5 165
36 Pd-CS/PEO/IA (0.63 μmol) 9.3 1.91 × 10− 3 30 5 166
37 3D CS-based scaffolds@Pd & Pt NPs (0.021 mg) 2–3.5 0.25 × 10− 3 50 17 167
38 Pd NPs@Fe3O4/CS-AG (0.015 mmol) 28–39 5.1 × 10− 3 2 8 168
39 GO-CS-CDNS-IL (1 % wt) 18 – 60 3 169
40 Pd NPs@CS-MWCNT (4 mg) – – 12 6 171
41 Pt@proline-functionalized/CS 8–14 – 60 5 172
42 Pd@CS-CD-MGQDs (0.5 mg) 10 – 60 10 173
43 CS/GA/RGO/Pd 7 2.08 × 10− 3 28 7 174
44 PdNPs/GQD-CS (0.062 mol%) 6–8 – 60 5 175
45 Pd/CoFe2O4/CS (4 mg) 20 13.1 × 10− 3 1 5 176
46 Pd-CS-g-C3N4 (10 mg) 8 11.0 × 10− 3 2 10 177
47 Pd@CS (0.2 mol%) 1.8 16.5 × 10− 3 4 18 178
48 Pd/CS/γMnO2 10 – 1 8 179
49 CS@nanozero-valent iron – 2.45 × 10− 3 28 7 181
50 CS/ZnO ND (nanoneedles) 39.9 – – – 182
51 oCNT-CS-xFe2O3-yBi2O3 7–9 – 60 10 183
52 TiO2/ZnO@CS gel beads (18 mg) 35.6 – 1.7 – 184
53 CS/TiO2-Fe2O3 8.7 – 70 – 185

➢ The use of these catalytic systems on an industrial scale.
➢ More use of these catalytic systems in magnetic form.
➢ Further functionalization of CS with various compounds such as al­
dehydes to make Schiff base catalytic systems.
➢ Catalytic reduction of aliphatic nitro compounds.
Declaration of competing interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence
the work reported in this paper.
Data availability
No data was used for the research described in the article.
Acknowledgments
We gratefully acknowledge the funding support from National Key
R&D Program of China (2022YFD2200705), Jiangsu Agricultural Sci­
ence and Technology Innovation Fund (CX(22)2045), and the Iranian
Nano Council, Amirkabir University of Technology-Mahshahr Campus,
and Farabi Educational Institute for the support of this work. This
research was also supported by Brain Pool Program through the National
Research Foundation of Korea (NRF) funded by the Ministry of Science
and ICT (grant number 2020H1D3A1A04081409).
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