Catalytic study of the copper-based magnetic nanocatalyst on the aerobic oxidation of alcohols in water

Article abstract of DOI:10.1007/s11164-021-04422-w

A copper-based magnetic nanocatalyst has been prepared by co-precipitation method and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET analysis. This new nanocatalyst displays a good activity toward the aerobic oxidation of a wide range of alcohols in water. Moreover, it is recyclable up to five following runs by simple filtration without any significant loss of its catalytic activity.

Full text of DOI:10.1007/s11164-021-04422-w

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-021-04422-w
Catalytic study of the copper‑based magnetic nanocatalyst
on the aerobic oxidation of alcohols in water
S. Saeid Saei Dehkordi · Jalal Albadi · Abbas Ali Jafari1 ·
1
2
Heshmat Allah Samimi2
Received: 5 December 2020 / Accepted: 27 February 2021
©
The Author(s), under exclusive licence to Springer Nature B.V. 2021, corrected publication 2021
Abstract
A copper-based magnetic nanocatalyst has been prepared by co-precipitation method
and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET
analysis. This new nanocatalyst displays a good activity toward the aerobic oxida-
tion of a wide range of alcohols in water. Moreover, it is recyclable up to ꢀve follow-
ing runs by simple ꢀltration without any signiꢀcant loss of its catalytic activity.
Keywords Magnetic nanocatalyst · Fe O @SiO · Aerobic oxidation · Alcohols ·
3
4
2
Carbonyl compounds
Introduction
The oxidation of alcohols into the corresponding aldehydes and ketones is a signiꢀ-
cant conversion in organic chemistry that has both academic and industrial impor-
tance [1, 2]. To achieve this conversion, a variety of procedures have been reported.
Conventionally, alcohol oxidation was accomplished by using stoichiometric oxi-
dants, such as manganese oxides, chromium salts, and the Dess–Martin reagent,
which produced large amounts of inorganic and organic wastes [3]. From the view-
point of economy and environmental protection, aerobic oxidation of alcohols with
molecular oxygen or air as the oxidant illustrated superior consideration in organic
chemical synthesis. The main reason for this methodology is attributed to the point
that oxygen is a green oxidant leading to water as the by-product [4].
*
*
Jalal Albadi
Albadi@sku.ac.ir; Jalal.albadi@gmail.com
Abbas Ali Jafari
Jafari@yazd.ac.ir
1
2
Department of Chemistry, Faculty of Sciences, Yazd University, Yazd, Iran
Department of Chemistry, Faculty of Science, Shahrekord University, Shahrekord, Iran
Vol.:(012
1
3456789)
3

S. S. S. Dehkordi et al.
Various metal-catalyzed systems have been reported for the aerobic oxidation of
alcohols that among them, copper-based catalysts have received signiꢀcant atten-
tion because of their low cost compared to conventional expensive metals [5–20].
Moreover, it is found that the copper nanoparticles supported exhibit suitable activ-
ity and selectivity, because of their high surface area, catalyst loading capacity, and
good dispersion [21, 22].
Cu is a 3d transition metal and has some exciting physical and chemical proper-
ties. Cu-based compounds can promote and undergo a variety of reactions due to
having diꢁerent oxidation states. Because of their unique characteristics and prop-
erties, Cu-based nanocatalysts have found many applications in nanotechnology,
including catalytic organic transformations, electrocatalysis, and photocatalysis [23].
2
+
Under oxidizing conditions, copper exists as Cu , while reducing conditions favor
+
the Cu form. Diꢁerent performances of the two states may be traced to variances
2
+
in their hardness: Whereas the Cu ion is classiꢀed as a borderline Lewis acid, the
+
reduced complement, the Cu ion, is an model soft acid. Hard N- and O-donors lead
+
the coordination chemistry of divalent state, whereas the Cu ion favors ligands with
soft donor atoms, such as phosphorus, sulfur, or iodine [24].
Therefore, copper nanoparticles supported on various supports such as cellulose,
SiO , carbon-based materials, or polymers were developed as reactive and selective
2
catalytic systems [23].
The highly oxygenated supports such as Fe O @SiO as the O-donor support pro-
3
4
2
vide good dispersions of active sites, mainly of metal nanoparticles, leading to better
reactivity. These supports have great potential as stable inorganic ligands for coordi-
nation with metal such as copper nanoparticles, opposing from organic ligands [25].
Fe O @SiO contains multiple hydroxyl groups that perform as nucleation sites for
3
4
2
the metals such as copper nanoparticles and provide necessary support for the stabi-
lization of the nanoparticles. The catalysts obtained in this approach display distinc-
tive properties and ꢀnd their application in varied areas [26]. Moreover, the nano-
magnetic core–shell structure has attracted support because of the easy preparation,
good stability, high surface area, and low toxicity. The hydroxyl functional groups of
SiO provide a chemically modiꢀable surface which facilitates the immobilizing of
2
other diꢁerent metal catalysts [27].
Due to the fact that Fe O @SiO can act as a suitable support for the metal nano-
3
4
2
particles, in continuation of our researches on the improvement of new nanocatalysts
[
28–34], herein, we wish to report the use of Fe O @SiO to prepare an eꢂcient
3 4 2
copper-based magnetic nanocatalyst (Fe O @SiO /CuO nanocatalyst) for the chem-
3
4
2
oselective aerobic oxidation of alcohols in water (Scheme 1).
Experimental
All chemical materials were purchased from Sigma-Aldrich or Merck Chemical
Companies. Products were characterized by comparison of their spectroscopic data
1
(
H NMR, IR) and physical properties with those reported in the literature. X-ray dif-
fraction (XRD) patterns were obtained using a diꢁractometer APD2000 using Cu K
α
(
λ=1.5406 Å) radiation. The ICP–OES analysis was achieved by a Varian Vista-Pro
1
3

Catalytic study of the copper-based magnetic nanocatalyst…
O
Fe O @SiO /CuO
OH
3
4
2
nanocatalyst
Na CO , O
2
R1
R2
R1
R2
2
3
Water, Relux
1
2
R , R = H, Alkyl, Aryl
Scheme 1 Aerobic oxidation of alcohols catalyzed by Fe O @SiO –CuO nanocatalyst
3
4
2
7
410 device. Field emission scanning electron microscopy (FESEM) analysis was
performed using a MIRA 3 TESCAN instrument equipped with an EDS analytical
system. Transmission electron microscope (TEM) images were recorded on a TEM
microscope Zeiss EM10C at an accelerating voltage 80 kV. Magnetic saturation was
carried out using a vibrating sample magnetometer (VSM/model LBKFB, Kavir
Magnet Co., Kashan, Iran) at room temperature. The Brunauer–Emmett–Teller
(
BET) analysis was obtained using a gas adsorption–desorption analyzer (BEL-
SORP-mini 2). The XRF study was done by a Philips Venus 100 minilab instrument.
Preparation of Fe O magnetic nanoparticles
3
4
A mixture of FeCl ·6H O (5.2 g), FeCl ·4H O (2.0 g), and HCl 12 M (0.85 mL) was
3
2
2
2
dissolved in 25 mL of deionized water under N atmosphere with vigorous stirring.
2
The obtained solution was added dropwise into NaOH 1.5 M (250 mL) under a con-
tinuous N ꢃow for 15 min, while the reaction media were being stirred vigorously.
2
The precipitated black Fe O MNPs were separated by an external magnet, washed
3
4
with deionized water, and then dried in the oven [35].
Synthesis of silica‑coated Fe O magnetic nanoparticles (Fe O @SiO )
3
4
3
4
2
1
.2 g of Fe O MNPs was dispersed in 20 mL ethanol and sonicated for 15 min,
3 4
followed by the addition of 1 mL triethylamine. Then, 0.8 mL tetramethyl orthosili-
cate (TMOS) was added dropwise into the reaction solution under violent stirring.
The resulting dispersion was stirred for 30 min and sonicated again for 15 min. The
precipitate was removed by an external magnet, washed with deionized water and
EtOH, and dried at 80 °C.
Preparation of Fe O @SiO /CuO nanocatalyst
3
4
2
At ꢀrst, Na CO solution (50 mL, 0.05 M) was added dropwise into a mixture of
2
3
Cu(NO ) ·3H O (50 mL, 0.025 M) and Fe O @SiO (0.1 g) under vigorous stirring
3
2
2
3
4
2
for 24 h at 50–60 °C. Then, the precipitate was separated by an external magnet,
1
3

S. S. S. Dehkordi et al.
washed with deionized water, and dried for 2 h at 100 °C followed by calcination at
3
00 °C for 3 h to aꢁord the Fe O @SiO /CuO nanocatalyst.
3 4 2
General procedure
A mixture of alcohol (1 mmol), Na CO (2 mmol), and Fe O @SiO /CuO nano-
2
3
3
4
2
catalyst (0.04 g) in water was stirred under oxygen at reꢃux condition. After reac-
tion completion, the catalyst was separated from the reaction mixture by external
magnetic ꢀeld, washed with hot EtOAc (2×5 mL), and dried for consecutive reac-
tion runs. Then, the ꢀltrate was cooled to room temperature, quenched with 2 M
HCl aqueous solution, ꢀltered, and extracted with dichloromethane. The solvent was
evaporated and the organic layer dried over anhydrous Na SO . Evaporation of the
2
4
solvent followed by column chromatography on silica gel (n-hexane/ethyl acetate
9
:1 as v/v%) aꢁorded the pure products.
Results and Discussion
Catalyst characterization results
Figure 1 exhibits the XRD images of Fe O @SiO and Fe O @SiO /CuO nanocata-
3
4
2
3
4
2
lyst. From Fig. 1a, the diꢁraction peaks located at 30.28°, 35.54°, 43.48°, 53.44°,
5
7.20°, 62.92°, and 74.48° can be attributed to the crystal planes (220), (311),
(
400), (422), (511), (440), and (533) of cubic Fe O with inverse spinel structure,
3
4
respectively [36]. It can be seen from Fig. 3b that the diꢁraction peaks at 35.79°,
3
9.02°, 48.83°, 57.60°, 63.04°, 66.29°, and 75.43° are veriꢀed the CuO forming
Fig. 1 The XRD patterns of Fe O @SiO (a) and Fe O @SiO –CuO nanocatalyst (b)
3
4
2
3
4
2
1
3

Catalytic study of the copper-based magnetic nanocatalyst…
with monoclinic phase on the surface of Fe O @SiO support [37]. Furthermore,
3
4
2
after immobilization of the CuO and the next calcination, no phase change observed,
which revealed that the crystalline structure of the nanocatalyst has been retained.
The FESEM micrographs of Fe O @SiO and Fe O @SiO /CuO are shown in
3
4
2
3
4
2
Fig. 2. The FESEM images exhibit that nanoparticles are almost uniform in spheri-
cal shape and possess particle diameters less than 40 nm. The lower aggregation
of nanoparticles in the Fe O @SiO /CuO in comparison with Fe O @SiO can be
3
4
2
3
4
2
conꢀrmed by precipitation of CuO nanoparticles on the surface of Fe O @SiO .
3
4
2
The evaluation of the EDS analysis, as shown in Fig. 2c and d, presented the Cu
−1
content of about 13.2% ww in accordance with the obtained results by ICP–OES
−
1
−1
(
13.4% ww ) and XRF analysis (13.5% ww ). From the TEM images, CuO nan-
oparticles are spread on the surface of Fe O @SiO support. The nanoparticles
3
4
2
are almost uniformly in spherical shape with core–shell structure at about 13 nm
(
Fig. 3).
According to the IUPAC classiꢀcation, the N adsorption–desorption isotherms
2
showed typical IV isotherms with a type H1 hysteresis loop that is characteristic of
the highly ordered mesoporous material (Fig. 4).
The BET analysis showed that the speciꢀc surface area of Fe O @SiO and
3
4
2
2
−1
2
−1
Fe O @SiO /CuO was 106 m g and 122 m g , respectively (Table 1). Also,
3
4
2
mean pore diameter and total pore volume of Fe O @SiO were found to be
3
4
2
3
−1
7
.821 nm and 0.183 cm g , respectively.
Fig. 2 The FESEM images of Fe O @SiO (a) Fe O @SiO –CuO nanocatalyst (b), the EDS analysis of
3
4
2
3
4
2
Fe O @SiO (c), and Fe O @SiO –CuO nanocatalyst (d)
3
4
2
3
4
2
1
3

S. S. S. Dehkordi et al.
Fig. 3 The TEM images of the Fe O @SiO –CuO nanocatalyst
3
4
2
Fig. 4 The N adsorption–desorption isotherms of Fe O @SiO and Fe O @SiO /CuO nanocatalyst
2
3
4
2
3
4
2
Table 1 Structural properties of
Sample
BET surface
Average pore Pore vol-
3
the Fe O @SiO and Fe O @
2
−1
3
4
2
3
4
area (m g
)
size (nm)
ume (cm
SiO /CuO nanocatalyst (BET
−1
2
g
)
analysis)
Fe O @SiO
2
106
122
7.821
6.907
0.183
0.239
3
4
Fe O @SiO /CuO
3
4
2
1
3

Catalytic study of the copper-based magnetic nanocatalyst…
Fig. 5 The pore diameter size distribution of Fe O @SiO and Fe O @SiO /CuO nanocatalyst
3
4
2
3
4
2
The mean pore diameter and total pore volume of the Fe O @SiO /CuO were
3
4
2
3
−1
found to be 6.907 nm and 0.239 cm g , respectively (Fig. 5). All of the results
indicated that the incorporation of CuO on the surface of Fe O @SiO and calcina-
3
4
2
tion leads to surface area increasing as well as pore volume increasing.
The magnetic property of nanoparticles was evaluated by vibrating a sample
magnetometer using model 7410 series, LBKFE at ambient temperature with ꢀeld
sweeping from−15,000 to+15,000 Oe. The magnetic saturation was measured
to be 47.51 emu/g− and 23.25 emu/g for Fe O @SiO and Fe O @SiO /CuO
1
−1
3
4
2
3
4
2
Fig. 6 The magnetic hysteresis loops of (a) Fe O @SiO and (b) Fe O @SiO /CuO nanocatalyst
3
4
2
3
4
2
1
3

S. S. S. Dehkordi et al.
(
Fig. 6). Almost any hysteresis loop was not seen for both samples. These results
indicated that both catalysts are super paramagnetic. A decrease in Fe O @SiO /
3
4
2
CuO is related to CuO grafting to the surface of Fe O @SiO .
3
4
2
Catalytic performance
Initially, to optimize the reaction conditions, we checked the aerobic oxidation of
-chloro-benzyl alcohol in the presence of Fe O @SiO /CuO nanocatalyst under O
4
3
4
2
2
at diꢁerent conditions. The performance of various Fe O @SiO /CuO nanocatalysts
3
4
2
containing 8, 13, and 20 wt. % CuO was studied on this reaction. The catalyst con-
taining about 13 wt. % of CuO showed the highest yield of reaction of about 95%, in
relatively lower reaction time. Moreover, the eꢁect of various catalyst amounts was
checked and found that using 0.04 g of the catalyst provided the best results. The
model reaction was studied in diꢁerent solvents and under solvent-free conditions.
Also, the eꢁect of various bases on the progress of the reaction has been examined.
It is found that the catalytic activity of Fe O @SiO /CuO nanocatalyst in the pres-
3
4
2
ence of Na CO in water under reꢃux conditions is signiꢀcantly higher than the
2
3
other solvents and the solvent-free conditions (Table 2).
Under optimized conditions, aerobic oxidation of a wide range of alcohols was
studied. The catalyst performance displayed a good activity on the aerobic oxida-
tion of benzylic alcohols having electron-donating and electron-withdrawing groups.
The oxidation of primary and secondary aliphatic alcohols was also investigated
under similar reaction conditions, which showed that desired carbonyl products are
obtained in high yields. Furthermore, aldehydes or ketones are the only products of
the all reactions and no other products were identiꢀed in these processes that sug-
gest the selectivity of the catalyst to these constituents. It is found that the oxidation
of the bulky aliphatic alcohols such as menthol is slower than other aliphatic ones
(
Table 3). Moreover, all the products could be easily separated and puriꢀed by col-
umn chromatography in high yields.
Table 2 Optimization of the
Yield (%)a
Entry
Conditions
Catalyst
Time (min)
reaction conditions
amounts (g)
1
2
3
4
5
6
7
8
9
EtOH/r.t
EtOH/r.t
EtOH/reꢃux
EtOH/reꢃux
0.02
0.04
0.02
0.04
0.02
0.04
0.06
0.02
0.04
0.02
0.04
180
180
180
180
180
180
180
90
–
–
30
50
H O/r.t
–
2
H O/r.t
Trace
Trace
70
93
Trace
2
H O/r.t
2
H O/reꢃux
2
H O/reꢃux
60
180
180
2
1
1
0
1
MeCN/reꢃux
MeCN/reꢃux
Trace
a
Isolated pure products
1
3

Catalytic study of the copper-based magnetic nanocatalyst…
Table 3 Aerobic oxidation of alcohols catalyzed by Fe O @SiO /CuO nanocatalyst
3
4
2
Entry
Alcohol
Product
Time
min)
Yield (%) a
(
1
2
3
4
5
6
7
8
9
C H CH OH
C H CHO
45
60
60
60
60
60
90
90
60
90
90
45
60
80
80
90
90
90
60
92
93
95
95
92
89
91
89
94
92
95
92
94
91
92
91
92
89
88
6
5
2
6
5
2-ClC H CH OH
2-ClC H CHO
6
4
2
6 4
4-Cl C H CH OH
4-ClC H CHO
6 4
2
6
3
2
2,4-ClC H CH OH
2,4-Cl C H CHO
6
4
2
2 6 3
4-(Me N)C H CH OH
4-(Me N)C H CHO
2 6 4
2
6
4
2
3-OHC H CH OH
3-OHC H CHO
6
4
2
6 4
4-Cl-3-NO C H CH OH
4-Cl-3-NO C H CHO
2 6 3
2
6
3
2
2-BrC H CH OH
2-BrC H CHO
6
4
2
6 4
4-BrC H CH OH
4-BrC H CHO
6 4
6
4
2
10
11
12
13
14
15
16
17
18
19
3-NO C H CH OH
3-NO C H CHO
2
6
4
2
2 6 4
4-NO C H CH OH
4-NO C H CHO
2 6 4
3,4,5-(MeO) C H CHO
4-MeOC H CHO
6 4
2
6
4
2
3,4,5-(MeO) C H CH OH
3
6
2
2
3 6 2
4-MeOC H CH OH
6
4
2
C H CH CH OH
C H CH CHO
6
5
2
2
6 5 2
C H CH CH CH OH
C H CH CH CHO
6 5 2 2
6
5
2
2
2
C H CH(Me)CH OH
C H CH(Me)CHO
6
4
2
6 4
CH CH CH CH OH
CH CH CH CHO
3 2 2
3
2
2
2
CH CH(OH)CH
CH COCH
3
3
3
3
H
O
O
O
OH
OH
H
O
H
2
2
0
1
90
89
87
HO
O
CH
2
OH
CHO
120
2
2
2
3
OH
O
120
160
88
89
O
HO
2
2
4
5
OH
O
90
91
87
OH
O
O
180
HO
O
H
H
O
O
O
OMe
OMe
OMe
OMe
a
Isolated yield. Products were characterized by comparison of their spectroscopic data and physical prop-
erties with those reported in the literature [4–11, 21, 26]
1
3

S. S. S. Dehkordi et al.
Table 4 Recyclability study
Run
1
2
3
4
5
of the Fe O @SiO /CuO
3
4
2
nanocatalyst
Time (min)
Yield (%)
60
95
60
94
65
94
70
92
70
89
a
a
Isolated yields
Table 5 Comparison between Fe O @SiO /CuO nanocatalysts with some other catalysts employed for
3
4
2
the aerobic oxidation of benzyl alcohol
Entry
Solvent
Catalyst
Time (h)
Yield (%) a
Reference
1
2
3
4
5
6
MeCN
MeCN
Toluene
DMF
POM/ZrO2
4
6
3
2
24
0.75
81
50.8
97
90
99
9
12
16
17
CuBr /NHPI
2
Ru-DD3
Cu-AOOPs catalyst
[L2CuBr]/TEMPO/NMI
MeCN
18
H O
Fe O @SiO /CuO nanocatalyst
92
This work
2
3
4
2
a
Isolated yield
The recyclability of the catalyst was also investigated on the aerobic oxidation of
-chloro-benzyl alcohol under optimized reaction conditions. After reaction com-
4
pletion, the catalyst was recovered, was washed with hot ethanol, and after drying
was reused in the consecutive reaction runs. Results exhibited a constant activity
of the catalyst during the ꢀve runs without any signiꢀcant loss in catalytic activ-
ity (Table 4). Moreover, the leaching test of the Cu into the reaction mixture by
ICP–OES analysis was studied. It was observed that the diꢁerence between the Cu
contents of the fresh catalyst and the reused catalyst (ꢀfth run) was only 3.1%, which
showed the low leaching amount of copper oxide catalyst into the reaction mixture.
In order to conꢀrm the merit of this method, Table 5 shows the comparison of
the results found from the aerobic oxidation of benzyl alcohol in the presence of
Fe O @SiO /CuO nanocatalyst with some of the other reported catalysts. In com-
3
4
2
parison with other catalysts, Fe O @SiO /CuO nanocatalyst catalyzed the reaction
3
4
2
eꢁectively in water and provides the desired products at high yields in relatively short
reaction times. Moreover, it is safe, is easy to handle, and can be recovered more than
ꢀ
ve runs by simple ꢀltration. The reaction in the presence of some other catalysts
has been performed in organic solvents such as DMF and MeCN. Moreover, other
reported methods required longer reaction times and also performed in the presence
of additional amounts of the base or acid. Furthermore, in some reactions, additive
reagents such as 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) are needed.
1
3

Catalytic study of the copper-based magnetic nanocatalyst…
Conclusion
In summary, Fe O @SiO –CuO as an eꢂcient recyclable magnetic nanocatalyst
3
4
2
was prepared and studied on the aerobic oxidation of alcohols in water. The Fe O @
3
4
SiO –CuO nanocatalyst exhibits a high performance with a superior selectivity. This
2
nanocatalyst is safe, is easy to handle, and can be recovered more than ꢀve runs by
simple ꢀltration. Moreover, high yield of products, relatively short time of reactions,
ease of workup, and clean procedure can represent this method as a suitable and
applicable substitute to the common methods.
Supplementary Information The online version contains supplementary material available at https://doi.
org/10.1007/s11164-021-04422-w.
Acknowledgement We are thankful to the Shahrekord and Yazd University for the support of this work.
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