Magnetic nanoparticles supported Cu2+ and Ce3+ complexes: toward the chemical and electrochemical oxidation of alcohol and sulfide derivatives

Article abstract of DOI:10.1007/s11164-019-03846-9

Abstract: Heterogeneous catalysts are more prominent rather than homogenous catalysts since they are simply separated from products. To improve and develop heterogeneous catalysts, two core–shell magnetic nanocatalysts are prepared by anchoring of Cu and Ce complexes on the surface of Fe₃O₄, then the efficiency of the obtained catalysts are tested toward both chemical and electrochemical oxidation of sulfide and alcohol derivatives. Characterization of mentioned catalysts was performed by using FT-IR, XRD, EDX and SEM. The obtained results confirm that the reported method has outstanding advantages such as short reaction time, high yield, easy operation, easy separation, inexpensive and non-toxic material and chemical and thermal stability. Graphical abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s11164-019-03846-9

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-019-03846-9
Magnetic nanoparticles supported Cu2+ and Ce3+
complexes: toward the chemical and electrochemical
oxidation of alcohol and sulfde derivatives
Taiebeh Tamoradi, et al. [full author details at the end of the article]
Received: 15 February 2019 / Accepted: 28 April 2019
© Springer Nature B.V. 2019
Abstract
Heterogeneous catalysts are more prominent rather than homogenous catalysts since
they are simply separated from products. To improve and develop heterogeneous cat-
alysts, two core–shell magnetic nanocatalysts are prepared by anchoring of Cu and
Ce complexes on the surface of Fe3O4, then the efciency of the obtained catalysts
are tested toward both chemical and electrochemical oxidation of sulfde and alcohol
derivatives. Characterization of mentioned catalysts was performed by using FT-IR,
XRD, EDX and SEM. The obtained results confrm that the reported method has
outstanding advantages such as short reaction time, high yield, easy operation, easy
separation, inexpensive and non-toxic material and chemical and thermal stability.
Graphical abstract
Vol.:(0123456789)
1 3

T. Tamoradi et al.
Keywords Fe3O4 · Cu · Ce · Sulfde · Alcohol · Chemical oxidation ·
Electrochemistry
Introduction
In the last decade, vast research interest has lead to performing oxidation reac-
tions because of their applications in many pharmaceutical, biological active mol-
ecules and chemical synthesis. On the other hand, oxidation of sulfdes and alco-
hols are an important class of oxidation reactions in organic synthesis because
of their properties and applications in many biological active molecules, chemi-
cal synthesis and pharmaceuticals such as lansoprazole, fpronil, acetaminophen,
and pantoprazole. Therefore, there is a great interest to synthesis of abovemen-
tioned compounds with an economic and simple pathway [1–4]. In connection
with this topic, heterogeneous catalysts contain various metal complexes (Fe, Co,
Ni) supported on nanoparticles and the mesoporous were recently employed for
the oxidation of sulfdes and alcohols [5–10]. In line with this, there are reports
of metal-based catalysts for oxidation of alcohols and sulfdes using H2O2 as the
oxidant.
Among the enormous variety of oxidizing reagents, H2O2 is suggested as a
sustainable green because traditional reagents have disadvantages such as the use
of stoichiometric amounts of oxidant, the formation of toxic waste products, and
rendering impossible the reusability of the catalyst. Also, among various sup-
ports, magnetic nanoparticles are considered as ideal supports because of their
simple recovery [11–13]. In recent years, attention focused on the Fe3O4 because
such nanoparticles have much better magnetic properties than other magnetic
nanoparticles. Notably, transfer of electrons between Fe2+ and Fe3+ on octahedral
sites in Fe3O4 inverse cubic spinal structure caused unique electrical and magnetic
properties in these nanoparticles. It should be mentioned that properties of Fe3O4
arise from their size and structure of particles. These nanoparticles are widely
studied because of their application in the feld of biomedical, corrosion protec-
tive, catalyst, as anticancer agent, pigments in paints and coating [14–17]. In spite
of the great attention to the oxidation reactions in recent years, oxidation of alco-
hol and sulfde have rarely been done in the presence of the catalyst heterogene-
ous based on Cu [18–21]. Also, up to date, the reports about oxidation of alcohol
and sulfde were not done in the presence of heterogeneous catalysts based on Ce.
On the other hand, electrocatalytic conversion of organic compounds to useful
chemicals is the eco-friendly vision in the green and low-cost synthesis approach
[22]. Herein, we have simply immobilized Cu and Ce complexes on the surface
of coated Fe3O4 magnetic nanoparticles with aspartic acid as the green and avail-
able ligand. Then, prepared catalysts were characterized by physical techniques
and tested in the oxidation of alcohols and sulfdes. The ofered protocol has out-
standing advantages such as easy separation of catalyst from mixed reaction, high
yield, reaction short time, the use of green and available materials, etc.
1 3

Magnetic nanoparticles supported Cu2+ and Ce3+
…
Experimental
Materials
Used materials in this work such as metal ions, aspartic acid, all reagents and all
solvents are purchased from Merck, Flucka or Aldrich and used without further
purifcation.
Measurement
Fourier transform infrared (FTIR) spectra and powder X-ray difraction (XRD)
measurements of samples were recorded using with a Bruker VERTEX 80 v model
using the KBr pellets and Co radiation source with a wave length=1.78897 Å,
40 kV, respectively. TGA measurement and elemental analysis of all samples were
performed by a Shimadzu DTG-60 instrument and energy-dispersive X-ray spec-
troscopy (EDAX, TSCAN), respectively. The amount of metals (Cu and Ce) and the
external morphology of catalyst were investigated by inductively coupled plasma-
optical emission spectrometry (ICP-OES) and FESEM-TESCAN MIRA3.
Preparation of Fe3O4@Aspartic‑M (M = Cu and Ce)
The 1 g of Fe3O4 nanoparticles were synthesized by the reported methods in the
literature and then reacted with 1.5 mL of (3-Chloropropyl)trimethoxysilane in hex-
ane under refux conditions for 24 h. The obtained back powder was separated with
an external magnetic feld and dried at 60 C and then reacted with 1.5 g of aspartic
acid in 50 mL of toluene under a refux reaction for 24 h. Finally, Fe3O4@Aspartic
was separated from a mixed reaction by an external magnetic feld. Then, in order
to have synthesis of Fe3O4@Aspartic-M (M=Cu and Ce) catalyst, 2.5 mmol metal
ions (Cu or Ce) was added to 1 g of Fe3O4@Aspartic in ethanol for 16 h. Finally,
prepared Fe3O4@Aspartic-M (M=Cu and Ce) was separated from a mixed reaction
by an external magnetic feld and washed with ethanol.
General procedure for the oxidation of sulfdes
A mixture containing sulfde (1 mmol), H2O2 (0.5 mL) and catalyst (0.007 g) was
stirred at room temperature under solvent-free conditions. After completion of the
reaction (tested by TLC), catalyst was easily separated by an external magnet and
sulfoxide derivatives were extracted with ethyl acetate to give the pure products.
General procedure for the oxidation of alcohols
A mixture containing of 1 mmol aromatic alcohols (1 mmol), H2O2 (0.7 mL) and
catalyst (0.015 g) in acetonitrile solvent was stirred at room temperature. After
1 3

T. Tamoradi et al.
completion of the reaction (tested by TLC), catalyst was easily separated by an
external magnet and aldehyde derivatives were extracted with acetonitrile to give the
pure products.
Electrocatalytic oxidation of sulfde and benzyl alcohol
The electrocatalytic oxidation of sulfde and alcohols was tested by µAutolab type
III in an electrochemical cell containing a three electrode system, an Ag/AgCl as
reference electrode, a platinum wire as counter electrode and glassy carbon elec-
trode (GCE) as working electrode for support of nanocatalyst. The electrochemical
reactions were tested in both acetonitrile and aqueous 1 M KOH solutions.
Results and discussion
Catalyst preparation
In order to design a recoverable catalyst system for oxidation sulfdes and alco-
hols, according to Scheme 1, magnetic nanoparticles were coated with Cu and Ce
complexes.
Catalyst characterization
The successfully immobilization of Cu and Ce complexes on the surface of Fe3O4
was confrmed by using Fourier transform infrared spectroscopy, scanning electron
Scheme 1 General route for the fabrication of M@Fe3O4 (M=Cu and Ce)
1 3

Magnetic nanoparticles supported Cu2+ and Ce3+
…
microscopies, X-ray difraction, energy-dispersive X-ray spectroscopy, and a vibrat-
ing sample magnetometer.
In order to investigate the morphology of prepared samples, we used SEM analy-
sis in which prepared nanoparticles have spherical and homogeneous morphology in
these images (Fig. 1).
The energy-dispersive X-ray spectroscopy (EDX) analysis of Cu@Fe3O4 (a) and
Ce@Fe3O4 (b) indicated the presence of N, O, C, Si, Cu species and N, O, C, Si, Cu,
Ce species in the mentioned catalysts in which was confrmed the immobilization
Cu and Ce complexes on the surface of Fe3O4 (Fig. 2).
FT-IR spectra of Fe3O4, chloro-functionalized Fe3O4, Cu@Fe3O4 and Ce@
Fe3O4 is a confrmation for the synthesis of the mentioned compounds (Fig. 3).
Fig. 1 SEM images of Cu@Fe3O4 (a) and Ce@Fe3O4 (b)
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T. Tamoradi et al.
Fig. 2 EDX spectrum of Cu@Fe3O4 (a) and Ce@Fe3O4 (b)
Fig. 3 FT-IR spectra of Fe3O4 (a), chloro-functionalized Fe3O4 (b), Fe3O4@Aspartic (c) Ce@Fe3O4 (d)
and Cu@Fe3O4 (e)
The presence of a sharp peak at approximately 578 cm−1 at all samples is depend-
ent to the Fe–O band of the spinel structure. The characteristic absorption band at
2850–2965 cm−1 is assigned to C–H stretching vibration in Fig. 3b–e, which could
1 3

Magnetic nanoparticles supported Cu2+ and Ce3+
…
Fig. 4 The XRD patterns of Cu@Fe3O4 (a) and Ce@Fe3O4 (b)
due to functionalization of Fe3O4 with 3-choloropropyl) trimethoxysilane. Also, the
connection of aspartic ligand of the surface of Fe3O4 was confrmed by the presence
of the C=O strong absorption at approximately 1600 cm−1.
The structure of cubic inverted spinal of the immobilized chloro-functionalized
Fe3O4 with Cu and Ce complexes was confrmed by XRD patterns (Fig. 4) and the
presence of difraction peaks of (2 2 0), (3 1 1), (4 0 0), (4 2 2), (5 1 1), and (4 4 0)
in the mentioned catalysts is due to green degredation of Fe3O4 nanoparticles [23].
Catalytic studies
In order to test catalytic activity of prepared catalysts, we decided to examine the
catalyst in the oxidation reactions such as oxidation of sulfde and alcohol deriva-
tives (Scheme 2). Firstly, the amount of catalyst is optimized for the oxidation of
methyl phenyl sulfde (Table 1). We selected the Cu@Fe3O4 catalyst for the synthe-
sis of methyl phenyl sulfoxide in the presence of 0.5 mL of H2O2 in the solvent-free
conditions. It should be noted that solvent-free conditions were usually selected as
optimization conditions in the synthesis of sulfoxide derivatives. Also, in order to
extend the scope of this work, we synthesized many sulfde derivatives in the pres-
ence of the obtained optimization conditions (Table 2).
In order to have optimization of conditions for the oxidation of alcohol deriv-
atives, various amounts of Cu@Fe3O4 catalyst were optimized for the oxidation
of 1 mmol benzyl alcohol in the presence of H2O2 (0.7 mL) as green oxidant in
1 3

T. Tamoradi et al.
Scheme 2 Oxidation of sulfde
and alcohol in the presence of
M@Fe3O4 (M=Cu and Ce)
Table 1 Optimization of reaction conditions for the synthesis of methyl phenyl sulfoxide in the presence
of Cu@Fe3O4
Entry
Solvent
Type of catalyst
Amount of cata- Time (min)
lyst (mg)
Yielda (%)
1
2
3
4
5
6
Solvent-free
Solvent-free
Solvent-free
Solvent-free
Solvent-free
Solvent-free
Fe3O4
7
7
3
5
7
9
120
120
100
80
45
40
Trace
Trace
74
80
97
Aspartic@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
97
aIsolated yield
acetonitrile. Then, various solvents were tested on the reaction results. Finally,
observation results are summarized in Table 3. It should be noted that many
aldehyde derivatives were also synthesized in the presence of the obtained opti-
mization conditions (Table 4).
After the investigation of catalytic activity of M@Fe3O4 (M = Cu and Ce),
the reusability of mentioned nanoparticles was tested in the synthesis of methyl
phenyl sulfoxide and benzaldehyde in which the results of this study are shown
in Figs. 5 and 6.
1 3

Magnetic nanoparticles supported Cu2+ and Ce3+
…
Table 2 Oxidation of sulfde using H2O2 in presence of M@Fe3O4 (M=Cu and Ce)
Entry
1
Substrate
Product
Time (min)
Yield (%)a
Cu
45
Ce
Cu
Ce
95
2a
S
40
97
2b
2c
2d
S
S
75
65
85
89
91
93
2
3
75
92
60
50
75
60
88
90
85
92
S
4
S
2e
5
aIsolated yield
Table 3 Optimization of reaction conditions for the synthesis of benzaldehyde in the presence of Cu@
Fe3O4
Entry
Solvent
Type of ctalyst
Amount of
Time (min)
Yielda (%)
catalyst (mg)
1
2
3
4
5
6
7
8
9
Acetonitrile
Acetonitrile
Acetonitrile
Acetonitrile
Acetonitrile
Acetonitrile
Solvent-Free
H2O
Fe3O4
15
15
15
18
13
11
15
15
15
110
110
110
110
110
110
110
110
110
26
29
67
69
52
33
Trace
21
18
Aspartic@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Cu@Fe3O4
Dichloromethane
aIsolated yield
Electrocatalytic studies
As mentioned above, electrochemical conversions of chemical compounds at hetero-
geneous catalysts into desired materials can be a good candidate on the way to low-
coast and rapid synthesis approaches, where it not required to have the additional
1 3

T. Tamoradi et al.
Table 4 Oxidation of alcohol using H2O2 in presence of M@Fe3O4 (M=Cu and Ce)
Entry
Substrate
Product
Yield (%)a
Cu
Ce
OH
1
4a
67
62
OH
4b
4c
61
48
63
45
2
Cl
OH
3
H
3CO
aIsolated yield
Fig. 5 Reusability of Cu@Fe3O4 (a) and Ce@Fe3O4 (b) in the synthesis of methyl phenyl sulfoxide
homogenous reagent (such as H2O2 that we have used for chemical conversions of
sulfde and alcohols) in the progress of catalytic reaction. Herein, the usability of as-
prepared catalysts toward oxidation of sulfde and non-aliphatic alcohols via electro-
chemistry was also investigated. Figures 7 and 8 show the comparison of cyclic vol-
tammograms recorded by glassy carbon electrodes modifed by pristine Fe3O4 and
Cu/Ce-loaded on Fe3O4 nanoparticles in the absence (dark line) and presence (pink
line) of 50 µM benzyl alcohol (Fig. 7) or 50 µM sulfde (Fig. 8). In the case of benzyl
alcohol, it is oxidized by pristine Fe3O4 in acetonitrile (CAN) and a catalytic current
ca.~3 A per gram of catalyst (A g−1) can be seen. After modifcation of Fe3O4 by
1 3

Magnetic nanoparticles supported Cu2+ and Ce3+
…
Fig. 6 Reusability of Ce@Fe3O4 (a) and Ce@Fe3O4 (b) in the synthesis of benzaldehyde
15
10
5
15
10
5
15
10
5
Cu@Fe3O4
in ACN
Ce@Fe3O4
in ACN
Fe3O4
in ACN
0
0
0
-5
-5
-5
0
0.4
0.8
1.2
1.6
0
0.4
0.8
1.2
1.6
0
0.4
0.8
1.2
1.6
E / V (vs. Ag/AgCl)
E / V (vs. Ag/AgCl
E / V (vs. Ag/AgCl)
6
5
6
6
5
Ce@Fe3O4
in water
Fe3O4
in water
Cu@Fe3O4
in water
5
4
4
4
3
3
3
2
2
2
1
1
1
0
0
0
-1
-1
-1
0
0.2
0.4
0.6
0
0.2
0.4
0.6
0
0.2
0.4
0.6
E / V (vs. Ag/AgCl)
E / V (vs. Ag/AgCl)
E /V (vs. Ag/AgCl)
Fig. 7 Electrocatalytic (cyclic voltammogram with scan rate 0.05 V s−1) oxidation of benzyl alcohol by
Fe3O4 nanoparticles and after loading of Cu+2 and Ce+3 on it, in acetonitrile (containing 0.01 M ammo-
nium hexafuorophosphate as electrolyte) and water (1 M KOH) solvents
a complex containing Cu+2, the catalytic current is slightly increased. In the mean-
time, Ce+3 complex@Fe3O4 exhibits a higher current density rather than Cu+2 com-
plex@Fe3O4. On the contrary, Cu+2 complex@Fe3O4 displays the catalytic activ-
ity also in aqueous solution, while it cannot be seen for the Ce+3 complex@Fe3O4,
indicating that the higher activity of Ce+3 complex is in organic solvent rather than
aqueous solution, and it is completely vice versa in the case of Cu+2 complex.
1 3

T. Tamoradi et al.
380
280
180
80
380
280
180
80
380
280
180
80
Fe3O4
in ACN
Cu@Fe3O4
in ACN
Ce@Fe3O4
in ACN
-20
-20
-20
0
0.4 0.8 1.2 1.6
0
0.4 0.8 1.2 1.6
E / V (vs. Ag/AgCl)
0
0.4 0.8 1.2 1.6
E / V (vs. Ag/AgCl)
E / V (vs. Ag/AgCl)
5
4
5
4
5
Fe3O4
in water
Cu@Fe3O4
in water
Ce@Fe3O4
in water
4
3
3
3
2
2
2
1
1
1
0
0
0
-1
-1
-1
0
0.2
0.4
0.6
0
0.2
0.4
0.6
0
0.2
0.4
0.6
E / V vs. Ag/AgCl
E / V (vs. Ag/AgCl)
E / V (vs. Ag/AgCl)
Fig. 8 Electrocatalytic (cyclic voltammogram with scan rate 0.05 V s−1) oxidation of sulfde by Fe3O4
nanoparticles and after loading of Cu+2 and Ce+3 on it, in acetonitrile (containing 0.01 M ammonium
hexafuorophosphateas electrolyte) and water (1 M KOH) solvents
Table 5 Comparison of Cu@Fe3O4 and Ce@Fe3O4 in the oxidation of methylphenylsulfde and benzal-
dehyde with previously reported procedure
Entry
Substrate
Catalyst
Time (min)
Yield (%)a
1
2
3
4
7
8
9
10
11
14
15
Methylphenylsulfde
Methylphenylsulfde
Methylphenylsulfde
Methylphenylsulfde
Methylphenylsulfde
Methylphenylsulfde
Benzaldehyde
Benzaldehyde
Benzaldehyde
Benzaldehyde
Benzaldehyde
O(IV)–MCM-41
VO-salen-MCM-41
Ni–salen–MCM-41
VO2F(dmpz)2
Cu@Fe3O4
Ce@Fe3O4
MOF-253-Ru7
AuCl
240
120
156
300
45
95 [24]
95 [25]
90 [26]
95 [27]
97 [This work]
95 [This work]
90 [2]
100 [28]
79.8 [19]
40
180
600
480
110
110
FS-4
Cu@Fe3O4
Ce@Fe3O4
69 [This work]
67 [This work]
aIsolated yields
The above explanations are also seen in electrocatalytic oxidation reaction of
sulfde. As can be seen in Fig. 8, in ACN solvent Cu+2 complex@Fe3O4 display
about 2.2 and 2.9 times higher catalytic activity rather than Cu+2 complex@Fe3O4
and pristine Fe3O4, respectively. Whereas, in KOH aqueous solution, Cu+2 com-
plex@Fe3O4 has displayed two fold higher catalytic current than Cu+2 complex@
Fe3O4 and Cu+2 Fe3O4. One reason for these observations may be referred to
1 3

Magnetic nanoparticles supported Cu2+ and Ce3+
…
soft and hardness of metal ions. Ce+3 and OH− are classifed as hard ions, while
Cu+2 ions have a borderline soft and hardness properties. Consequently, Ce+3 ions
strongly interact with OH¯ in aqueous solution, and its catalytic activity is decreased.
On the contrary, organic or aqueous solution may have a similar solvation efect on
the prepared Cu+2 complex, and consequently, the catalytic activity is just slightly
changed in KOH aqueous or ACN solutions.
Comparison of the catalyst
In order to show the high efciency of prepared catalyst, catalytic activity of Cu@
Fe3O4 and Ce@Fe3O4 in the synthesis of methyl phenyl sulfoxide and benzalde-
hyde compared with other catalysts in the literature in which this comparison shows
advantages such as easy separation of catalyst from mixed reaction, high yield, high
thermal and mechanical stability, short reaction time, easy operation, the use of
green and available materials, etc (Table 5).
Conclusion
In summary, two nanocatalysts were designed by anchoring of Cu2+ and Ce3+ com-
plexes on the surface of Fe3O4 as a magnetic support. The oxidation of alcohol and
sulfde derivatives was tested in the presence of designed catalysts in which high
catalytic activity was shown for the mentioned catalysts. The perspective of electro-
chemical oxidation of these substances can be solvent-free in a two electrode system.
Also, the use of non-toxic and available materials, the use of short procedure and
high yield, recoverable catalyst and simple operation are outstanding benefts of the
proposed protocol.
Acknowledgements The authors are deeply grateful to University of Kurdistan University for fnancial
support of this research project.
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Afliations
Taiebeh Tamoradi1,3 · Aso Navaee1 · Abdollah Salimi1 ·
Seyedeh Masoumeh Mousavi2 · Mohammad Ghadermazi1 · Hojat Veisi3
* Taiebeh Tamoradi
t.tabss@yahoo.com
* Aso Navaee
aso.navaee@gmail.com
1
Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran
2
Department of Environmental Planning, Tehran University, Tehran, Iran
3
Department of Chemistry, Payame Noor University, Tehran, Iran
1 3