MIL-101 metal-organic framework: A highly efficient heterogeneous catalyst for oxidative cleavage of alkenes with H2O2

Article abstract of DOI:10.1016/j.catcom.2011.10.005

In the present work, a new and efficient method for direct oxidation of alkenes to carboxylic acids with H₂O₂ catalyzed by metal-organic framework MIL-101 is reported. In this transformation, the MIL-101 catalyzes the oxidation reactions by framework nodes and acts as a heterogeneous and reusable catalyst. The structure of MIL-101 was stable after three catalytic cycles.

Full text of DOI:10.1016/j.catcom.2011.10.005

Catalysis Communications 17 (2012) 18–22
Contents lists available at SciVerse ScienceDirect
Catalysis Communications
journal homepage: www.elsevier.com/locate/catcom
Short Communication
MIL-101 metal–organic framework: A highly efficient heterogeneous catalyst for
oxidative cleavage of alkenes with H2O2
⁎
⁎
Zahra Saedi, Shahram Tangestaninejad , Majid Moghadam ,
Valiollah Mirkhani, Iraj Mohammadpoor-Baltork
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 12 June 2011
Received in revised form 30 September 2011
Accepted 4 October 2011
Available online 12 October 2011
In the present work, a new and efficient method for direct oxidation of alkenes to carboxylic acids with H2O2
catalyzed by metal–organic framework MIL-101 is reported. In this transformation, the MIL-101 catalyzes the
oxidation reactions by framework nodes and acts as a heterogeneous and reusable catalyst. The structure of
MIL-101 was stable after three catalytic cycles.
© 2011 Elsevier B.V. All rights reserved.
Keywords:
Metal–organic framework
MIL-101
Hydrogen peroxide
Oxidation
Carboxylic acid
1. Introduction
[21] (Fig. 1). Due to the large pores and high surface area of the MIL-101,
this compound is a good candidate in catalysis. Kaskel et al. reported the
Metal–organic frameworks (MOFs), as a new class of porous solids,
have received considerable attention because of their potential applica-
tions in gas adsorption and separation processes [1,2], catalysis [3–6],
ion exchange [7], optoelectronics [8,9], and sensor technology [10].
Three decades before the birth of metal–organic frameworks (MOFs),
Tomic reported the materials which nowadays are known as MOFs,
metal–organic polymers or supramolecular structures [11]. The interest
in this field was developed by the Yaghi's group, which reported the
MOF-5 as an exceptionally stable and highly porous metal–organic
framework in 1999 [12]. Some structural properties of MOF such as
their high internal surface area and microporosity are comparable
to zeolites and for the most new MOF structures are higher than zeo-
lites [13]. So, based on these similarities, these frameworks can be
used as solid catalysts Pd-MOF [14], Al2 (BDC)3[15], Cu3(BTC)2[16],
[Zn2(bdc)(l-lac)(dmf)]·(DMF) [17], Cu(bpy)(H2O)2(BF4)2(bpy) [18],
Mn3(atpa)3(dmf)2and Mn2(tpa)2(dmf)2[19], and Cu(2-pymo)2 and
Co(PhIM)2[20]. First time in 2005, Ferey and co-workers reported the
synthesis and characterization of the metal–organic framework MIL-
101 [(Cr3X(H2O)2O(bdc)3; X=F, OH; bdc=benzene-1,4-dicarboxylate)]
catalytic activity of MIL-101 in the efficient cyanosilylation of aldehydes
[22]. Recently, the catalytic activity of MIL-101 has been reported in the
oxidation of tetralin [23,24].
Catalytic oxidation of alkenes to carboxylic acids and ketones is a
valuable reaction in organic synthesis [25] and several oxidation
pathways have been reported in the literatures [25–33]. During the
last few decades, numerous efforts have been made to devise safer al-
ternatives for these useful reactions. Therefore, in order to develop a
mild oxidative method, we decided to investigate the catalytic activ-
ity of MIL-101 in the direct oxidation of alkenes to carboxylic acids
(Scheme 1).
2. Experimental
2.1. Synthesis of MIL-101
MIL-101 was synthesized based on procedure reported by Férey et
al. [21]. In a typical procedure, a mixture of Cr(NO3)3·9H2O (1.2 g,
3 mmol), terephthalic acid (H2bdc, 500 mg, 3 mmol), and HF (5 M,
0.6 mL, 3 mmol) in H2O (15 mL) was heated in a Teflon-lined stain-
less steel autoclave at 220 οC for 8 h. The resulting green solid was
passed through a coarse glass filter to remove the unreacted colorless
crystals of H2bdc and then, the green solid materials were filtered on
a dense paper filter. The green raw product was washed with hot
DMF (100 °C, 8 h, 2 times) and with hot EtOH (80 °C, 8 h, 2 times), fil-
tered off, and dried overnight in an oven at 75 °C.
⁎
Corresponding author. Tel.:+98 311 7932710; fax: +98 311 6689732.
E-mail addresses: stanges@sci.ui.ac.ir (S. Tangestaninejad),
moghadamm@sci.ui.ac.ir (M. Moghadam).
1566-7367/$ – see front matter © 2011 Elsevier B.V. All rights reserved.
doi:10.1016/j.catcom.2011.10.005

Z. Saedi et al. / Catalysis Communications 17 (2012) 18–22
19
separated from reaction mixture, washed with acetonitrile and
dried carefully before using in the next run. The same procedure
was repeated for other runs. The amount of Cr leached to the reaction
mixture was measured by inductively coupled plasma. After the reac-
tion was completed, the catalyst was filtered. The filtrate was dis-
solved in strong acidic solution (HNO3:HCl, 1:3). Then, the amount
of Cr leached was determined by ICP analysis.
2.5. Spectral data of the corresponding carboxylic acids
Heptanoic acid (C6H13COOH):
Mass (m/e): 130.1
FT-IR (KBr, υ (C m−1)): 3215.72 (O–H), 1711.51 (C=O),
1282.43 (C–O)
1H-NMR (CDCl3, 400 MHz): 0.85 (t, 2H, J=7.03 Hz), 1.28 (m,
6H), 1.53 (t, 2H, J=7.13 Hz),
2.16 (t, 2H, J=7.5 Hz)
Nonanoic acid (C8H17COOH):
Mass (m/e): 158.13
FT-IR (KBr, υ (C m−1)): 3419.17(O–H), 1719.23 (C=O), 1200.47
(C–O)
Fig. 1. Structure of MIL-101.
1H-NMR (CDCl3, 400 MHz): 0.85 (d, 1H, J=14 Hz), 1.28 (s, 10H),
1.53 (t, 1H, J=7.27 Hz),
2.2. Physico-chemial measurements
2.16 (t, 2H, J=7.4 Hz)
Undecanoic acid (C10H21COOH):
Specific surface area was measured by adsorption–desorption of
Mass (m/e): 186.16
N2 gas at 77 K with ASAP 2000 micromeritics instrument. FT-IR spec-
FT-IR (KBr, υ (C m−1)): 3501.13 (O–H), 1714.41 (C=O), 1277.61
(C–O).
tra were recorded using potassium bromide pellets (MOF: KBr, 5: 95)
in the range of 400–4000 cm−1 by a Jasco FT/IR-6300 instrument.
X-ray diffraction (XRD) analysis was carried on a D8 Advanced Bruker
anode X-ray Diffractometer with Cu Kα (λ=1.5406 Å) radiation. Ther-
mogravimetric analysis (TGA) was performed on a mettler TA 4000 in-
strument at a heating rate of 5 K min−1. The ICP analyses were carried
out by a Perkin-Elmer optima 7300 DV spectrometer. GC analyses
1H-NMR (CDCl3, 400 MHz): 0.85 (t, 3H, J=6.78 Hz), 1.28 (br s,
14H), 1.53 (t, 2H, J=7.08 Hz),
2.16 (t, 2H, J=7.48 Hz).
Glutaric acid (C5H8O4):
Mass (m/e): 132.97
FT-IR (KBr, υ (C m−1)): 3425.92 (O–H), 1731.76 (C=O),
1208.18 (C–O).
were performed using
a Shimadzu GC-16A gas chromatograph
equipped with a flame ionization detector and a 2 m column packed
with silicon DC-200 or Carbowax 20 m. In GC experiments, n-decane
was used as internal standard.
1H-NMR (CDCl3, 400 MHz): 2.37 (t, 4H, J=7.48 Hz), 1.88
(m(q), 2H, J=7.45 Hz).
Adipic acid (C6H10O4):
Mass (m/e): 146.75
2.3. Catalytic experiments
FT-IR (KBr, υ (C m−1)): 3425.92 (O–H), 1714.41 (C=O),
1220.72 (C–O).
All reactions were performed in a 25 mL round-bottom flask
equipped with a condenser and a magnetic stirrer bar. The MIL-101
(5 mg, 0.0066 mmol) was added to a solution of alkene (0.5 mmol)
in CH3CN (3 mL). Then, H2O2 (30%, 500 μL, 5 mmol) was added to
the mixture and refluxed. The progress of the reaction was monitored
by GC. At the end of the reaction, the catalyst was filtered and washed
with CH3CN (10 mL). The solvent was evaporated and the pure prod-
ucts were obtained by chromatography on a short column of silica gel.
The products were characterized by 1H NMR, FT-IR spectroscopy and
mass spectrometry.
1H-NMR (CDCl3, 400 MHz): 1.53 (m, 4H), 2.2 (m, 4H).
Suberic acid (C8H14O4):
Mass (m/e): 174.84
FT-IR (KBr, υ (C m−1)): 3440.39 (O–H), 1732.73 (C=O),
1211.07 (C–O).
1H-NMR (CDCl3, 400 MHz): 2.16 (t, 4H, J=7.51 Hz), 1.54
(t, 4H, J=7.14 Hz), 1.29 (m, 4H).
2-(Carboxymethyl)benzoic acid or Homophthalic acid (C9H8O4):
Mass (m/e): 180.93
FT-IR (KBr, υ (C m−1)): 3079.76(O–H), 1684.52(C=O), 1277
(C–O).
2.4. Recycling test
1H-NMR (CDCl3,400 MHz) : 3.4 (s, 2H), 7.15 (m, 2H), 7.25
(t, 1H, J=7.4 Hz), 7.9 (d, 1H, J=7.11 Hz).
The oxidation of indene was chosen as a model substrate for
checking the reusability of MIL-101. After each run the catalyst was
3. Results and discussion
MIL-101 was synthesized by hydrothermal method. Figs. 2B and
3B show the X-ray diffraction patterns and FT-IR spectra of the
resulted green powder which are as same as reported previously
[34]. These observations confirmed the synthesis of MIL-101. The spe-
cific surface area of the obtained porous materials was determined
using nitrogen physisorption measurements at low temperature and
was obtained about 2125 m2 g−1 (Fig. 4A).
Thermal stability of the MIL-101 was measured by TGA method
(Fig. 5). Analysis of these thermograms strongly proposed that MIL-
Scheme. 1. Oxidative cleavage of alkenes with MIL-101.

20
Z. Saedi et al. / Catalysis Communications 17 (2012) 18–22
Fig. 4. N2 isotherms of: (A) fresh MIL-101, (B) recovered catalyst (■ Adsorption,
□ Desorption).
the glutaric acid (75%), adipic acid (90%) and suberic acid (98%),
respectively (Table 1, entries 1–3). Both adipic and suberic acids are
industrially very important. Even-numbered acyclic α-olefins such
as 1-octene, 1-decene, and 1-dodecene were easily converted into
their corresponding odd-numbered alkanoic acids of one less carbon
in 80–90% yields (Table 1, entries 5–7). The substituted cyclic olefin,
indene (Table 1, entry 4) was converted to 2-(carboxymethyl)benzoic
acid (homophthalic acid) in 100% yield. The catalytic activity of CrCl3
was investigated in the oxidation of indene under the same conditions
for MIL–101. The results showed that the product was epoxide and
the yield was about 17%. In the absence of catalyst only 15% of its corre-
sponding epoxide was produced in the oxidation of indene and no diac-
id was detected.
For a more complete study, the reusability of MIL-101 was also
investigated in the oxidation of indene. As mentioned before, the
product yield was 100% in the first run after 3 h. In the second and
third runs, the product yields decrease to 94% and 81%, respectively
(Table 2). In addition, a decrease in the reaction rate is observed
from the first to the third run as can be seen from Fig. 6. This is due
to the some catalyst leaching during the catalytic experiments. De-
spite decreasing in the reaction rate and yield, the catalyst reserve
Fig. 2. XRD patterns of MIL-101: (A) calculated one; (B) synthesized MIL-101 and
(C) recovered catalyst.
101 structure was stable and no further weight loss occurs below
350 °C. At temperatures higher than 350 °C, the framework structure
was decomposed.
The catalytic activity of the MIL-101 was evaluated in the oxida-
tion of alkenes with H2O2, in acetonitrile, under reflux conditions.
Table 1 presents the results of the oxidation of alkenes by MIL-101.
Cyclic alkenes such as cyclopentene, cyclohexene, and cyclooctene
were cleaved readily under the reaction conditions and generated
Fig. 3. FT-IR spectrum of MIL-101: (A) reported in 34; (B) before catalytic activity; (C)
Fig. 5. Thermogram of MIL-101.
recovered catalyst and (D) treatment with H2O2.

Z. Saedi et al. / Catalysis Communications 17 (2012) 18–22
21
Table 1
Oxidation of alkenes with H2O2 catalyzed by MIL-101 refluxing in acetonitrile
a
.
Entry
Alkene
Product
O
Yield (%)b
75
Time (h)
8
TOF (h−1
7.10
)
O
1
HO
OH
O
HO
2
90
8
8.52
OH
OH
O
O
O
3
4
98
4
3
18.56
25.25
H
CH2CO2H
CO2H
100
5
6
7
1-octene
1-decene
1-dodecene
CH3(CH2)5COOH
CH3(CH2)7COOH
CH3(CH2)9COOH
90
80
85
8
8
5
8.52
7.57
12.88
a
Reaction conditions: alkene (0.5 mmol), H2O2 (5 mmol), MIL-101 (5 mg, 0.0066 mmol), acetonitrile (3 mL).
GC yield based on the starting alkene.
b
Table 2
C=O vibrations appeared at 1709 and 1686 cm−1. To check this
point, a sample of catalyst was stirred with H2O2 in the absence of
substrate and the same results were observed (Fig. 3D).
Recyclability of MIL-101 in the oxidation of indenea.
Cr leached (mmol)
TOF (h−1
)
Yield (%)b
Run
Also, the XRD pattern of the recovered catalyst is as same as the
fresh catalyst but the peaks intensity has been decreased (Fig. 2C).
The N2 isotherm of the recovered catalyst is shown in Fig. 4B. It is
0.002
0.001
0.0006
25.25
23.74
20.45
100
94
81
1
2
3
clear that the surface area of the MIL-101 decreased to 1790 m2 g−1
.
a
Reaction conditions: indene (0.5 mmol), H2O2 (5 mmol), MIL-101 (5 mg, 0.0066 mmol),
acetonitrile (3 mL).
To check the heterogeneity of MIL-101 catalyst in liquid phase ox-
idation indene, a hot filtering experiment (separation of catalyst at
the reaction temperature) and recycling runs over the spent catalysts
were carried out at a fixed temperature (70 °C). In this case, the cata-
lyst was filtered off after 30 min reaction and the filtrate mixture was
then stirred at 70 °C for duration of up to 360 min (Fig. 7). The results
showed that no further progress was observed than in the presence of
catalyst. The low catalytic activity of Cr leached (and also CrCl3)
shows that the catalyst active sites are the framework nodes not
metals nodes [6].
In order to investigate the reaction mechanism, a series of oxida-
tion reactions were carried out using cyclohexene, cyclohexene
oxide and trans-1,2-cyclohexanediol. The results showed that all
these compounds were efficiently converted to adipic acid. As can
be seen in Scheme 2, the reaction times for oxidation of cyclohexene,
b
GC yield based on the starting alkene.
81% of its initial activity. The amounts of Cr leached were measured
by ICP technique and are shown in Table 2. As can be seen in
Table 2, the amount of Cr leached in the three runs is about 18% of
the initial Cr, which is in accordance to the decreasing of the product
yield from 100% in the first run to 81% in the third run. The nature of
the recovered MIL-101 was studied by FT-IR spectroscopy and XRD
analysis. The presence of new bands in 1500–1800 cm−1 is due to
the oxidative degradation of the MIL-101 structure. The presence of
bands corresponding to the carboxylic groups of terephthalic acid in
the spectral region of 1500–1800 cm−1 is an evidence for this obser-
vation (Fig. 3C). Moreover, new bands corresponding to stretching
100
50
0
0
0.5
1
1.5
2
2.5
3
3.5
time (h)
Fig. 6. Product conversion for MIL-101 catalyzed oxidation of indene; ▲ run 1, ■ run 2,
□ run 3.
Fig. 7. Indene oxidation after 3 h: ● Filtration test, and ▲ MIL-101.

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Z. Saedi et al. / Catalysis Communications 17 (2012) 18–22
bond in alkenes, this catalytic system has the following advantages:
i) using H2O2 as a clean and green oxidant, ii) no need to phase
transfer catalyst, iii) high to excellent yield, and iv) MIL-101 is a
heterogeneous and reusable catalyst.
Acknowledgment
We are thankful to the Center of Excellence of Chemistry of the
University of Isfahan for financial support of this work.
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InCl3
OsO4
t-BuOOH (70%) 90 0.58
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rt
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In comparison with previously reported methods for oxidation of
alkenes to carboxylic acids, the presented method is more efficient
and more acceptable. For example, although ozonolysis is a very reli-
able method, ozone gas is highly toxic and damaging to human health
and its generation requires special instrumentation. On the other
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Summary, in this work, a new route for conversion of alkenes to
their corresponding carboxylic acids is reported based on catalytic
properties of MIL-101 metal–organic framework. Comparison with
other systems that reported for oxidative cleavage of C-C double