MoO 3 nanoparticles synthesis via hydro-solvothermal technique and its application as catalyst for efficient ring opening of epoxides with amines under solvent-free conditions

Article abstract of DOI:10.1080/15533174.2013.809740

Molybdenum trioxide nanoparticles were synthesized using ammonium heptamolybdate tetrahydrate (AHM) through a facile hydro-solvothermal technique. The materials were characterized via X-ray diffraction (XRD), scanning electron microscopy (SEM), and transm

Full text of DOI:10.1080/15533174.2013.809740

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MoO3 Nanoparticles Synthesis via Hydro-Solvothermal
Technique and Its Application as Catalyst for Efficient
Ring Opening of Epoxides With Amines Under Solvent-
Free Conditions
Reihaneh Malakootia, Soheila Shafiea, Rahele Hosseinabadia, Majid M. Heravib, Masoumeh
Zakerib & Narges Mohammadib
a Department of Chemistry, Nanochemistry Research Laboratory, University of Birjand,
Birjand, Iran
b Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
Accepted author version posted online: 17 Dec 2013.Published online: 02 Jun 2014.
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To cite this article: Reihaneh Malakooti, Soheila Shafie, Rahele Hosseinabadi, Majid M. Heravi, Masoumeh Zakeri & Narges
Mohammadi (2014) MoO3 Nanoparticles Synthesis via Hydro-Solvothermal Technique and Its Application as Catalyst for
Efficient Ring Opening of Epoxides With Amines Under Solvent-Free Conditions, Synthesis and Reactivity in Inorganic, Metal-
Organic, and Nano-Metal Chemistry, 44:10, 1401-1406, DOI: 10.1080/15533174.2013.809740
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:1401–1406, 2014
Copyright ꢀ Taylor & Francis Group, LLC
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ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.809740
MoO3 Nanoparticles Synthesis via Hydro-Solvothermal
Technique and Its Application as Catalyst for Efficient Ring
Opening of Epoxides With Amines Under Solvent-Free
Conditions
Reihaneh Malakooti,1 Soheila Shafie,1 Rahele Hosseinabadi,1 Majid M. Heravi,2
Masoumeh Zakeri,2 and Narges Mohammadi2
1Department of Chemistry, Nanochemistry Research Laboratory, University of Birjand, Birjand, Iran
2Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran
oclinic (β-MoO3) phases, and hexagonal (h-MoO3) phase. It
was shown that β-MoO3 can be converted into α-MoO3 at tem-
Molybdenum trioxide nanoparticles were synthesized using am-
monium heptamolybdate tetrahydrate (AHM) through a facile
hydro-solvothermal technique. The materials were characterized
via X-ray diffraction (XRD), scanning electron microscopy (SEM),
and transmission electron microscopy (TEM). The mean diameter
of semispherical α-MoO3 nanoparticles was determined to be 20
5 nm. The catalytic performance of obtained products was ex-
amined in the ring opening of epoxides with diverse amines under
solvent-free conditions in excellent yields and short period of times.
perature around 400◦C.[10]
Previously, crystalline MoO3 nanoparticles were prepared
through various routes such as microplasma process,[11] ultra-
sonic,[12] electrospinning,[13] electrodeposition,[14] template,[15]
chemical vapor deposition (CVD),[16] aerosol-assisted CVD,[17]
thermal evaporation,[18] hot plate,[19] solvothermal,[20] and hy-
drothermal techniques,[21–26] incorporation with all citations
therein.[27,28]
Keywords β-aminoalcohol, metal oxide nanoparticles, molybdenum
On the other hand, β-amino alcohols are an important class
of organic compounds.[29] They are found in a wide variety
of biologically active alkaloids and peptides.[30] Amino alco-
hols are also useful as chiral auxiliaries and as ligands for
transition metals for asymmetric synthesis and catalysis.[31]
They are easily converted into many other molecules, includ-
ing amino acids and amino sugars.[32] The transformation of
an epoxy ring to the respective β-amino alcohol is also a cru-
cial step in the synthesis of anti-HIV agents,[33] the protein
kinase C inhibitor,[34] and antimalarial agents.[35] Several meth-
ods have been reported in the literature for the synthesis of
β-amino alcohols using several catalysts including sulfamic
acid,[36] amberlist-15,[37] metal triflates,[38] metal alkoxides,[39]
transition metal salts,[40] heteropolymolybdate or tungstate,[41]
monodispersed silica nanoparticles,[42] zeolites,[43] montmoril-
lonite clay,[44] and MCM-41.[45] In many of these cases, the ring
opening of epoxides is carried out in a solvent, and normally re-
quires many hours at reflux temperature under environmentally
unfriendly conditions.
trioxide, solvent-free
INTRODUCTION
Research on metal oxide nanoparticles has become more
intense due to their interesting physicochemical properties in
comparison with their bulk counterparts.[1] These functional ma-
terials are in use as adsorbents, sensors, photo devices, catalysts,
etc.[2] One of the most important metal oxides is molybdenum
trioxide (MoO3) that is a wide band-gap n-type semiconductor.
This material has received many attentions such as investigation
of its photo- and electrochromic properties,[3] catalytic behav-
ior,[4] sensor,[5] lubricant,[6] using in smart windows,[3] lithium
battery,[7] etc. Also molybdenum trioxide is used as a good pre-
cursor for synthesizing other significant compounds, such as
MoS2[8] and MoO2.[9]
Molybdenum trioxides can be found in three polymorphisms,
one stable orthorhombic (α-MoO3) phase, two metastable mon-
Accordingly, here we report the synthesis of MoO3 nanopar-
ticles through a simple solvo-hydrothermal approach via acid-
ification of ammonium heptamolybdate tetrahydrate (AHM),
(NH4)6Mo7O24·4H2O, in ethanol and subsequently adding 1-
octadecene, oleic acid, and oleylamine as surfactants. The
products were characterized by X-ray diffraction (XRD),
scanning electron microscopy (SEM), and transmission elec-
tron microscopy (TEM) techniques. To the best of our
Received 21 January 2013; accepted 27 May 2013.
We are thankful to Professor G. Christou and Dr. K. A. Abboud of
the University of Florida for their helps and consults.
Address correspondence to Reihaneh Malakooti, Department of
Chemistry, Nanochemistry Research Laboratory, University of Bir-
jand, Birjand, Iran. E-mail: rmalakooti@birjand.ac.ir; reihaneh.mala
kooti@gmail.com
1401

1402
R. MALAKOOTI ET AL.
SCH. 1.
knowledge, this catalyst has not been reported for the ring open- ture proceeded at 120◦C for corresponding time in Table 1.
ing of epoxides with aromatic amines (Scheme 1).
After completion of the reaction as indicated by thin layer chro-
matography (TLC), hot ethanol was added to the mixture, the
catalyst was filtered, and solvent was evaporated under reduced
pressure. The crude products were purified by re-crystallization
from ethanol.
EXPERIMENTAL
Oleylamine was purchased from Aldrich Company (Nether-
lands) and AHM, oleic acid and 1-octadecene were purchased
from Merck Company (Darmstadt, Germany). All materials
were used without further purification.
RESULTS AND DISCUSSION
A Bruker D8-advance X-ray diffractometer was used to
record XRD data with Cu Kα radiation (λ = 1.5406 Å). Data
were recorded with a speed of 2◦ min−1 and a step of 0.05º.
Using a CamScan MV2300 scanning electron microscope oper-
ating at 30 kV and a Philips CM10 transmission electron micro-
scope operating at 100 kV, SEM and TEM images were imaged,
respectively. Fourier transform infrared spectroscopy (FT-IR)
spectra of the samples were recorded on a Bruker Tensor 27
spectrometer. Melting points were measured using Barnstead
Electrothermal. GC Mass analysis was performed using Agilent
6890 GC system Hp-5 capillary 30 m × 530 μm × 1.5 μm
The expected reaction in acidic medium for isopolymolyb-
date anion is as follows[26]
:
Mo7O62−4 + 6H+ → 7MoO3 = 3H2O
In fact, increasing in the concentration of Mo7O624− or 6H+
leads to shift the equilibrium reaction to the right incorporated
with some halfway steps. In our synthesis, the intermediate com-
pounds including ammonium tetramolybdate, (NH4)2Mo4O13,
and ammonium octamolybdate, (NH4)4Mo8O26, were obtained.
Figure 1 shows the XRD of the intermediate compounds
(containing (NH4)2Mo4O13 and (NH4)4Mo8O26) and MoO3
1
nominal. H NMR spectra were recorded on a Bruker AQS-
AVANCE Spectrometer at 500 MHz, using tetramethylsilane
(TMS) as an internal standard.
Synthesis of MoO3 Nanoparticles
In a typical procedure, absolute ethanol (10 mL) was mixed
with 1-octadecene (20 mL), oleic acid (10 mL), and oleylamine
(1 mL) under magnetic stirring for a few minutes to form a
homogenous solution. Then, 0.1765 g of AHM was dissolved
in 4 mL of distilled water in a separate beaker, using 2M nitric
acid, the pH value of the solution was adjusted to 3, and this so-
lution was added slowly into the first solution under mechanical
stirring condition for 2 h. The obtained solution was transferred
into 90 mL teflon-lined stainless-steel autoclave and maintained
at 180◦C for 24 h. After cooling to room temperature, the precip-
itated solid was harvested by centrifugation, washed thoroughly
with distilled water, methanol, and toluene, and dried at vacuum
desiccator. Finally, this compound was annealed at 450◦C in air
for 2 h.
(b)
(a)
10
20
30
40
50
60
2θ°
Catalytic Reactions
Reaction of Epoxides With Amines: Typical Reaction
To a mixture of epoxide (1 mmol) and amine (1 mmol),
MoO3 nanoparticles (0.01 g) were added and the reaction mix-
FIG. 1. XRD patterns of (a) mixture of (NH4)2Mo4O13 and (NH4)4Mo8O26
and (b) α-MoO3 nanoparticles.
,

MoO3 NANOPARTICLES IN EPOXIDE RING OPENING
1403
TABLE 1
MoO3 nanoparticles catalyzed ring opening of epoxides with amines
mp (◦C)
Entry
1
Epoxide
Amine
Product
Time (min)
45
Yield (%)
88
Found
(Lit.)
Ref.
[46c]
1a
69–72
73–74
[47]
2
1b
40
85
101–103
102–104
[46a,b]
[48]
3
4
1c
40
45
85
85
57–58
67–69
59
1d
68–70
[47]
[46a,b]
[45]
5
6
7
1e
1f
45
45
40
80
85
80
120–121
52–53
122–123
54–55
1g
103–105
104–106
[45]
8
1h
40
80
100–102
101–103
nanoparticles. It is shown that after calcinations at 450◦C, the dispersed semispherical particles with the average size of 20
intermediate compounds decompose into pure α-MoO3 which 5 nm without any aggregation, which is in agreement with XRD
is in good agreement to the data (JCPDS No. 05-0508). The data.
widths of MoO3 XRD peaks in comparison with their corre-
In continuation of our interest in the synthesis of organic com-
sponded ones in the intermediates are larger, which may orig- pounds under solvent-free condition[49] herein, we report a sim-
inate from ammonia and water releasing.[25] Scherrer formula ple, environment-friendly, and proficient method for the prepa-
also estimates the MoO3 particles with average size of 30 nm.
ration of β-amino alcohols in the presence of catalytic amounts
SEM and TEM images of MoO3 nanoparticles are depicted of MoO3 nanoparticles as a green, reusable, and efficient cat-
in Figure 2 respectively. TEM image reveals the presence of alyst. In a typical procedure, cyclohexene oxide (1 mmol) and

1404
R. MALAKOOTI ET AL.
epoxypropyl phenyl ether, and their corresponding results are
summarized in Table 1. Epoxide opening in entries 7 and 8 in
Table 1 took place exclusively at the less-hindered carbon. It
is worthwhile to mention that desired regioselective transfor-
mation of epoxides to corresponding β-amino alcohols in high
yields was achieved by MoO3 nanoparticles and product 2 was
not observed (Scheme 1).
1
All reaction products were known and characterized by H
NMR, IR, GC mass, and melting point as comparing with those
obtained from authentic samples.
CONCLUSION
We present a novel and facile synthesis of pure molybdenum
trioxide nanoparticles (20
5 nm) via a solvo-hydrothermal
method. Final products were characterized using XRD, SEM,
and TEM techniques. To our knowledge, compared with other
similar previous works, our products have smaller size. Also
the catalytic performance of nanoparticles for the first time
was examined in the ring opening of epoxides with aromatic
amines. These reactions offer several advantages in preparative
procedures such as environmental compatibility, simplification
of work-up, formation of cleaner products, enhanced selectivity,
reduction of by-products, reduction in waste produced, and low
catalyst loading.
FUNDING
The authors are indebted to University of Birjand and Alzahra
University Research Councils for partial financial support of this
work.
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