Preparation of magnetically recyclable ZnFe2O4 nanoparticles by easy single-step co-precipitation method and their catalytic performance in the synthesis of 2-aminothiophenes

Article abstract of DOI:10.1002/aoc.4047

In this work, a new synthetic route for the preparation of ZnFe₂O₄ nanoparticles through the chemical co-precipitation using Fe²⁺ and Fe³⁺ ions in an alkaline solution was developed. The synthesized nanoparticles were characterized by XRD, FTIR, SEM, ICP-MS, DRS, TGA, VSM and elemental analysis. Characterization results confirmed the formation of single ZnFe₂O₄ phase, with an average particle size of 40?nm and a high saturation magnetization of 34?emu g^?1. The prepared material was employed as a catalyst for the synthesis of 2-aminotiophene derivatives through the Gewald reaction. This thermally and chemically stable nanocatalyst is environmentally benign, economical and reusable which can be easily recovered using an external magnet. Therefore, it appears that this methodology can be simply extended for industrial purposes.

Full text of DOI:10.1002/aoc.4047

Received: 22 June 2017
DOI: 10.1002/aoc.4047
Revised: 24 July 2017
Accepted: 24 July 2017
F U L L P A P E R
Preparation of magnetically recyclable ZnFe2O4
nanoparticles by easy single‐step co‐precipitation method
and their catalytic performance in the synthesis of
2‐aminothiophenes
N. Erfaninia1 | R. Tayebee1
| E.L. Foletto2 | M.M. Amini3 | M. Dusek4 | F.M. Zonoz1
1 Department of Chemistry, Hakim
Sabzevari University, Sabzevar
96179‐76487, Iran
2 Department of Chemical Engineering,
Federal University of Santa Maria, Santa
Maria 97105‐900, Brazil
In this work, a new synthetic route for the preparation of ZnFe2O4 nanoparticles
through the chemical co‐precipitation using Fe2+ and Fe3+ ions in an alkaline
solution was developed. The synthesized nanoparticles were characterized by
XRD, FTIR, SEM, ICP‐MS, DRS, TGA, VSM and elemental analysis. Character-
ization results confirmed the formation of single ZnFe2O4 phase, with an
average particle size of 40 nm and a high saturation magnetization of 34 emu
3 Department of Chemistry, Shahid
Beheshti University, G. C., Tehran, Iran
4 Institute of Physics of the Czech
Academy of Sciences, Na Slovance 2,
18221 Prague 8, Czech Republic
g
−1. The prepared material was employed as a catalyst for the synthesis of
2‐aminotiophene derivatives through the Gewald reaction. This thermally and
chemically stable nanocatalyst is environmentally benign, economical and
reusable which can be easily recovered using an external magnet. Therefore, it
appears that this methodology can be simply extended for industrial purposes.
Correspondence
R. Tayebee, Department of Chemistry,
Hakim Sabzevari University, Sabzevar,
96179‐76487, Iran.
KEYWORDS
Email: rtayebee@hsu.ac.ir
2‐aminothiophenes, Gewald reaction, magnetic nanoparticles, single‐step co‐precipitation, ZnFe2O4
1 | INTRODUCTION
agent,[12] high energy ball‐milling,[13] phase chemical
reaction,[14] polyethylene glycol‐assisted route,[15] thermal
Synthesis and application of ferrite nanoparticles of the
type MFe2O4, where M stands for divalent metal ions such
as Zn, Co, Mn, Mg, Ni, etc. have attracted extensive
consideration in the last decades.[1,2] Ferrites are ceramic
materials possessing interesting magnetic properties,
excellent chemical stability and mechanical strengths,
and offering widespread applications in several industrial
segments.[2] Among them, ZnFe2O4 has received much
attention due to its potential uses in optical and
electrical devices,[3] as adsorbent material for hot‐gas
desulfurization,[4] in catalytic transformations,[5] and in
biomedicine.[6] ZnFe2O4 has been fabricated using differ-
ent procedures, such as co‐precipitation,[7] solid‐state
reaction,[8] sol–gel,[9] glycine combustion method,[10]
microwave‐assisted solvothermal and solvothermal syn-
thesis,[11] combustion reaction using urea as reducing
plasma synthesis,[16] one‐step solid microwave combus-
tion method,[17] and synthesis in supercritical fluids.[18]
Zinc ferrite can be separated from reaction mixtures by
applying an external magnet and could be reused in
further reactions.[19,20]
The improvement of new methodologies for the direct
synthesis of significant complex molecules is a focal task
for current organic chemists.[21] In this unique situation,
improvement of multi‐component reactions is of funda-
mental significance.[22] 2‐Aminothiophenes have been
increasingly used as antitumor and antibacterial agents,
antioxidants, dyes, pharmaceutical and agrochemical
compounds.[23] Additionally, the thiophene ring is like-
wise found in numerous natural and synthetic biologically
active compounds.[24] In this context, 2‐aminothiophene
synthesis has attracted considerable attention, and many
Appl Organometal Chem. 2017;e4047.
wileyonlinelibrary.com/journal/aoc
Copyright © 2017 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4047

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ERFANINIA ET AL.
synthetic protocols have been developed.[24] However,
many of the reported methodologies require troublesome
preparation of the starting materials, multistep synthesis,
and resulting yields are low.
radiation (λ = 1.5418 Å) at 40 keV and 40 mA. The Fou-
rier transform infrared (FTIR) spectrum was recorded on
an 8700 Shimadzu spectrophotometer utilizing KBr
1
pellets. H‐ and 13C–NMR spectra were recorded on a
As a result of our current research and in continuation
of our previous works,[25] we are going to present an
eco‐friendly, novel, and low‐cost route for the synthesis
Bruker AVANCE 300 MHz spectrometer. Diffuse reflec-
tion/transmittance spectroscopy (DRS/DTS) was acquired
on an Avaspec‐2048‐TEC equipment. The chemical com-
position of the prepared material was obtained using an
inductively coupling plasma spectrometer (ICP‐MS;
model Vista‐pro). Thermal gravimetric analysis (TGA)
was done on a Bahr STA‐503 instrument on air atmo-
sphere at a heating rate of 10 °C min−1. Magnetic property
of the catalyst was attained via vibrating sample magne-
tometer/alternating gradient force magnetometer (VSM/
AGFM, MDK Co, Kashan, Iran, www.mdk magnetic.
com). A freeze dryer (Model FD‐10, Pishtaz Equipment
Engineering Co, Tehran, Iran) was utilized for drying of
the sample. Elemental analyses were accomplished with
a Thermo Finnigan Flash‐1112EA microanalyzer. The
progress of the reactions was shown by thin‐layer chroma-
tography (TLC). All the synthesized 2‐aminothiophenes
were distinguished by comparison of their physical and
spectral information with those already announced.[27–30]
of ZnFe2O4 nanoparticles using
a single‐step co‐
precipitation method under green and environmentally
friendly conditions. The obtained ZnFe2O4 nanoparticles
are then utilized as an efficient and reusable catalyst in
the synthesis of different 2‐aminothiophenes based on
the Gewald reaction in solvent‐less conditions at
100 °C.[26]
2 | EXPERIMENTAL
2.1 | Materials
All chemicals were purchased from Sigma‐Aldrich and
used without further purification: Ferrous chloride
tetrahydrate (FeCl2.4H2O), ferric chloride hexahydrate
(FeCl3.6H2O), zinc oxide (ZnO) and ammonium hydrox-
ide (NH4OH; 28%).
2.4 | Synthesis of 2‐aminothiophene
derivatives
2.2 | Preparation of ZnFe2O4
Zinc ferrite nanoparticles were obtained by the dispersion
of 0.2 g of ZnO nanoparticles in a 20 ml solution of
deionized water including FeCl3.6H2O (0.54 g; 2 mmol)
and FeCl2.4H2O (0.198 g; 1 mmol) at 50 °C under mag-
netic agitation and nitrogen atmosphere. After that, the
mixture was stirred for 10 min; then, an aqueous solution
of NH4OH (10 ml, 8 M) was slowly added to start the pre-
cipitation of ZnFe2O4. In order to accelerate the growth of
the particles, the reaction was performed at 50 °C for
10 min by magnetic stirring. Finally, the precipitate was
separated by a magnetic field and washed thoroughly
with deionized water for three times. Subsequently, the
produced solid was dried at 80 °C for 12 h. To study
impact the of drying conditions on the catalytic efficacy
of ZnFe2O4, we dried the prepared final material under
freeze conditions. Conclusions demonstrated no obvious
enhancement in the catalytic activity of this sample
compared with the one dried under conventional thermal
conditions as described above.
5 mmol of malonodinitrile, 5 mmol of sulfur powder and
5 mmol of ketone, were thoroughly mixed. Then, 0.03 g of
ZnFe2O4 nanoparticles was added, and the mixture was
warmed to 100 °C with constant stirring for 4 h. Eventu-
ally the reaction was stopped, ZnFe2O4 was separated
with a simple magnet, and the final product was dissolved
in 10 ml of hot ethanol. After that, the reaction mixture
was cooled to room temperature and decanted into
100 ml of ice‐water. The precipitate was filtered, washed
with cold water (5 °C) and dried at room temperature
for 12 h. To continue refinement, we purified the crude
product via silica gel column chromatography with 10: 1
hexane: ethyl acetate as eluent. Scheme 1 displays a
reaction scheme employed in this work for the synthesis
of 2‐aminothiophenes.
R1
CN
O
R2
R1
S
R2
NH2
CN
ZnFe2O4 (2.5 mol%)
or
O
(NC)2CH2
S8
or
,
100 ºC 4h
2.3 | Characterization techniques
NH2
( )n
Field emission scanning electron microscopy (FESEM)
was performed with XL‐30 Phillips (1992). The purity of
the sample was assessed by X‐ray diffraction (XRD) anal-
ysis on a PW1800‐PHILIPS diffractometer with Cu‐Kα
S
( )n
SCHEME
2‐aminothiophenes
1
Reaction scheme for the synthesis of

ERFANINIA ET AL.
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2.5 | Spectral data of some selected
600
500
400
300
200
100
0
compounds[30]
2.5.1 | 2‐Amino‐5‐ethylthiophene‐3‐
carbonitrile
FT‐IR (KBr) (νmax/cm−1): 3440, 3360, 3220, 2960, 2220,
1
1650, 1560, 1460, 1380, 1080, 840. H–NMR (300 MHz,
CDCl3): δH(ppm) 6.34 (s, 1H), 4.73 (brs, 2H), 2.60
(q, J.7.2 Hz, 2H), 1.20 (t, J.7.2 Hz, 3H); 13C–NMR(CDCl3):
δ 161.0, 132.0, 120.2, 115.9, 86.7, 23.0, 15.2 ppm.
2.5.2 | 2‐Amino‐4,5,6,7‐tetrahydro‐1‐
benzothiophene‐3‐carbonitrile
10
20
30
40
50
60
2
FT‐IR (KBr) (νmax/cm−1): 3440, 3340, 3200, 2910, 2840,
2200, 1650, 1640, 1520,1320, 1120, 680; 1H–NMR
(300 MHz, CDCl3): δH(ppm) 1.78 (t, 4H,2CH2), 4.64
(s, 2H, NH2), 2.49 (m, 4H, 2CH2); 13C–NMR(CDCl3):
δ 22.10, 23.34, 23.72, 24.10, 88.45, 115.59, 120.50,
132.27,160.15 ppm.
FIGURE 1 XRD pattern of ZnFe2O4
formation of ZnFe2O4 structure.[31] Moreover, no impu-
rity peaks were observed, confirming the high purity of
the sample.
The FTIR spectrum of ZnFe2O4 is shown in Figure 2.
Due to the interactions between oxygens and cations in
the octahedral and tetrahedral environment; three
vibrational frequencies were shown in the spinel structure
of zinc ferrite (666 cm−1, 543 cm−1, 450 cm−1). The major
frequency bands 666 and 543 cm−1 correspond to vibra-
tions of the metal at the tetrahedral site (tetrahedral
Zn2+ stretching), and the low‐frequency band 453 cm−1
is proven with Fe3+ vibration frequencies in the
octahedral sites.[32] The weak band close to 1590 cm−1 is
assigned to H–O–H bending vibration mode due to the
absorption of humidity, because the FT‐IR sample disks
were prepared in an open‐air atmosphere. The band at
3400 cm−1 corresponds to the attendance of hydroxyl
groups.[33]
2.5.3 | 2‐Amino‐5, 6, 7, 8‐tetrahydro‐4H‐
cyclohepta[b]thiophene‐3‐carbonitrile
FT‐IR (KBr) (νmax/cm−1): 3440, 3309, 3207, 2921, 2842,
2200, 1622, 1569, 1514, 1438, 1400, 1344, 1128, 829, 493.
1H–NMR (300 MHz, CDCl3): δH(ppm) 4.58 (s, 2H),
2.56–2.63 (m, 4H), 1.80–1.82 (m, 2H), 1.64–1.65 ppm
(m, 4H); 13C–NMR(CDCl3): δ 158.2, 136.8, 123.7, 116.0,
91.7, 31.9, 29.4, 29.1, 28.1, 27.2 ppm.
2.5.4 | 2‐Amino‐4‐phenylthiophene‐3‐
carbonitrile
FT‐IR (KBr) (νmax/cm−1): 3420, 3320, 3200, 2220, 1630,
1570, 1430, 1300, 1190,940, 768, 715; 1H–NMR
(300 MHz, CDCl3): δH(ppm) 7.60 (m, 2H), 7.44 (m, 2H),
7.38 (m, 1H), 6.32 (s, 1H), 5.02 (brs, 2H);
13C–NMR(CDCl3): δ 164.1, 139.9, 134.2, 128.8, 128.2,
127.2, 116.2, 105.9, 88.0 ppm.
3 | RESULTS AND DISCUSSION
3.1 | Characterization
XRD was used to investigate the phase of produced
binary, ZnFe2O4, oxide. As shown in Figure 1, the
XRD pattern displayed diffraction lines of a high crys-
talline nature at 2θ = 30.0, 35.2, 42.9, 53.2 and 56.5o,
which corresponds to (220), (311), (400), (422), and
(511) crystal planes, respectively. This pattern matched
well with the JCPDS of 22–1012 confirming the
FIGURE 2 FTIR spectrum of ZnFe2O4 nanoparticles

4 of 7
ERFANINIA ET AL.
Optical properties of ZnFe2O4 were investigated by
UV–Vis diffuse spread reflectance (DRS) measurement
at room temperature (Figure 3). It is explicit that the
obtained sample shows excellent visible‐light absorption,
which is consistent with the black color of ZnFe2O4. The
high visible light absorbance demonstrates that the
obtained ZnFe2O4 may have high visible‐light utilization
efficiency. Besides, the absorption band of ZnFe2O4 shows
a relatively steep edge without a shoulder, illustrating that
the absorption of the visible light range can be assigned
to a characteristic band transition instead of surface
states.[34]
Distribution and morphology of ZnFe2O4 particles was
investigated by FESEM (Figure 4). Qualitative analysis via
FESEM revealed a homogeneous and uniform distribu-
tion of spherical ZnFe2O4 particles, with an average size
of 40 nm. Chemical composition (mol%) of the ZnFe2O4
sample was obtained from ICP analysis, being Zn and
Fe of 14.20 and 28.49, respectively, resulting in the atom
ratio of 1:2. This finding is in fair agreement with the
atomic composition of ZnFe2O4, thus confirming the for-
mation of single‐phase ZnFe2O4.
The magnetic property of ZnFe2O4 was characterized
by VSM (Figure 5). Detailed magnetic measurements, i.e.,
zero‐field cooling and magnetic hysteresis loops at several
temperatures, field cooling magnetization vs temperature,
relaxation under different applied fields at 5 K, have been
accomplished to check the magnetic property of the syn-
thesized ZnFe2O4 nanoparticles. The superparamagnetic
property of the catalyst, which accounts for its simple
recovery, was corroborated by VSM analysis. There was
no hysteresis loop, and the ratio of magnetic remanence/
magnetic saturation was 34.0 emu g_1.[35,36] The saturation
magnetization of spinel ferrites originates from the differ-
ence in the magnetic moments of the cations occupying
the octahedral and tetrahedral lattice sites positions. As
Zn2+ cation is not magnetic, its value for Zn‐based ferrites
FIGURE 4 SEM images of ZnFe2O4
200
100
0
-100
-200
-300
-400
FIGURE 5 Magnetization vs applied magnetic field for ZnFe2O4
nanoparticles
directly reflects the distribution of the Fe3+ ions among
two sub‐lattices.[37,38]
The thermal stability of the prepared ZnFe2O4 nano-
particles in air was investigated (Figure 6). According to
the TGA analysis, a distinct weight gain (~2.6%) was
250
300
350
400
450
500
Wavelength (nm)
FIGURE 3 DRS spectrum of ZnFe2O4

ERFANINIA ET AL.
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103
102
101
100
99
98
97
96
95
100
200
300
400
500
600
700
Temperature (oC)
FIGURE 6 Thermogravimetric (TGA) analysis for ZnFe2O4
FIGURE 7 Effect of reaction time on the condensation reaction
occurred due to absorption of oxygen atom. This finding
clearly confirmed zinc ferrite was started to decompose
at 400 °C with a distinct mass loss (around 4%). Further-
more, continues mass loss around 90–200 °C is attributed
to the loss of surface moisture. Notably, release of surface
moisture was masked with the mentioned weight gain. To
study the thermal stability of the prepared ZnFe2O4, it
was calcined in a muffle‐oven at 600 °C for 3 h. Color
change of zinc ferrite to brown was obvious. XRD analysis
of the final material showed that ZnO and Fe3O4 were
generated as minor phases; however, ZnFe2O4 was
observed as the major phase. This finding clearly
confirmed the TGA analysis.
amounts of ZnFe2O4. Thus, the reaction of elemental sul-
fur, cyclohexanone, malonodinitrile was investigated
under a solventless condition at 100 °C in the presence of
0–0.03 g of nanocatalyst. The screening results of the reac-
tion are summarized in Table 1. In the absence of the cat-
alyst, the reaction was rather non‐profitable, and just 6% of
the product was attained after 4 h (entry 1). On the other
hand, the addition of 0.01 g (0.85 mol%) and 0.03 g
(2.5 mol%) of the catalyst provided 57 and 80% yield,
respectively, during the same time (Entries 2 and 4). As
expected, the yield was growing with increasing the cata-
lyst concentration. However, excessive amounts of the cata-
lyst lowered the yield to 52% (Entry 6). Such lowering can
be explained by the decreasing concentration of reactants
3.2 | Catalytic activity of ZnFe2O4 in the
synthesis of 2‐aminothiopohene derivatives
TABLE 2 Synthesis of different 2‐aminothiophene derivatives
under the optimum reaction conditions.
The catalytic effectiveness of the heterogeneous catalytic
system was checked for the synthesis of 2‐amino‐4,5,6,7‐
tetrahydro‐1‐benzothiophene‐3‐carbonitrile with different
Entry Ketone/aldehyde Product
M.P.
Yield(%)
1
120–122 30a
144–145 55
146–147 80
TABLE 1 Effect of ZnFe2O4 amount on the condensation of
cyclohexanone, elemental sulfur and malonodinitrile.
2
3
Entry ZnFe2O4 (g) ZnFe2O4(mol%) Time (h) Yield (%)
1
2
3
4
5
6
0
0
4
4
4
4
4
4
6
57
60
80
60
52
0.01
0.02
0.03a
0.04
0.05
0.85
1.65
2.50
3.30
4.10
4
5
128–130 51
134–136 35
Reaction conditions: malonodinitrile (5 mmol), Cyclohexanone (5 mmol),
and sulfur powder (5 mmol) were mixed in the presence of nano‐ZnFe2O4
and the reaction mixture was warmed to 100 °C for 4 h.
6
148–150 25
aNo obvious enhancement on the yield was observed when the catalyst
treated under freeze drying was used.
aIn absolute ethanol (4 h reflux). General reaction condition is described in
the footnote of Table 1.

6 of 7
ERFANINIA ET AL.
TABLE 3 Comparison of the catalytic activity of ZnFe2O4 with some reported catalysts in the synthesis of 2‐amino‐4,5,6,7‐tetrahydro‐1‐
benzothiophene‐3‐carbonitrile.
Condition/
solvent
Cat.
(g)
Entry
Catalyst
Time (h)
Temp. (°C)
Yield (%)
E‐Factor (g)
TON
Ref.
1
ZnFe2O4
4
100
80
free
0.03
0.05
0.04
0.04
0.02
0.05
0.2
0.24
2667
This work
[39]
2
3
4
5
6
7
ZnO34%/NCP
Bulk TiO2
Bulk ZnO
Nano ZnO
MgO/Al2O3
KF/Al2O3
4
100
100
100
100
60
76
74
65
70
91
91
free
6.30
6.52
1520
1850
1625
3500
1820
455
[27]
[27]
[39]
[40]
[41]
10
10
6
free
free
7.60
free
6.95
8
ethanol
ethanol
17.04
15.84
3.5
78
Turnover number (TON) was calculated as yield(%)/g of catalyst.
at the active sites. Hence, 0.03 g of catalyst was determined
as the optimal quantity for the reaction.
catalyst, generality, small amount of the additive, and
economical production.
Figure 7 demonstrates the effect of reaction time on
the yield under the standard reaction condition. It was
observed that the yield grows with augmenting the reac-
tion time.
4 | CONCLUSION
In this study, ZnFe2O4 nanoparticles have been success-
fully prepared using a rapid and facile method through
the chemical co‐precipitation route of Fe2+ and Fe3+ ions
in an alkaline medium. Then, the prepared ZnFe2O4 mag-
netic nanoparticles were used as an environmentally
friendly heterogeneous catalyst for the synthesis of 2‐
aminothiophene derivatives by Gewald reaction. We
showed that the high activity of zinc ferrite could origi-
nate from the dual Lewis acidic Fe3+ sites along with
oxide and Zn2+ ions, which can act as Lewis basic centers.
The present methodology is characterized by sufficient
generality, compatibility with different functional groups,
short reaction time, high yield, easy work‐up, and envi-
ronmentally benign conditions. Owing to the reusing
and recycling of the catalyst, the method might solve
many separation problems it could be easily scaled‐up in
organic synthesis as well as in industry.
To focus the universality of this catalyst, we examined
cyclopentanone, cyclohexanone and cycloheptanone, as
cyclic ketones, along with butyraldehyde, diethyl ketone
and acetophenone. All the examined carbonyl
compounds showed good reactivity towards the Gewald
condensation reaction and led successfully to the desired
products with good selectivity (Table 2). However,
findings revealed that linear carbonyl compounds were
less efficient than cyclic ketones. Moreover, cyclohexa-
none provided the best yield and behaved better than
cyclopentanone and cycloheptanone.
Several protocols have been accounted for the synthe-
sis of 2‐amino‐thiophenes. The reaction efficiency of the
present method was compared with those reported in
the literature, and the results are summarized in Table 3.
The comparison was performed regarding catalyst
amount, reaction time and yield. The obtained results
demonstrated that 0.03 g of ZnO prompted to 33% of the
desired product; while, Fe3O4 was ineffectual after 4 h.
Meanwhile, ZnFe2O4 showed a high activity and led to
80% yield. The oxide anions, as the basic parts of the
catalyst, would catalyze addition and cyclization of the
condensation reactions; whereas, the dehydration may
proceed by Fe3+ of Fe2O3 as the acidic parts of the cata-
lyst.[31] Except the commercial ZnO, all the solid bases
can produce the desired product in convenient yields
under moderate conditions. However, our methodology
offers a one pot single‐step preparation of the target prod-
ucts under aerobic, simple, and solvent‐free conditions
without utilizing the powerful Lewis bases. Moreover,
the present process allows some advantages such as mild
reaction condition, environmentally benign nature of the
ACKNOWLEDGMENTS
Partial financial support from the Research Councils of
Hakim Sabzevari University is greatly appreciated.
ORCID
R. Tayebee http://orcid.org/0000-0003-1211-1472
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