Selective Oxidation of Hydrocarbons and Alcohols Using Phen-MCM-41 as an Efficient Co-Catalyst in Combination with NHPI-Based Nano-Magnetic Catalyst

Full text of DOI:10.1080/00304948.2020.1716434

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
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Selective Oxidation of Hydrocarbons and Alcohols
Using Phen-MCM-41 as an Efficient Co-Catalyst
in Combination with NHPI-Based Nano-Magnetic
Catalyst
Rahman Hosseinzadeh, Mohammad Mavvaji, Mahmood Tajbakhsh, Zahra
Lasemi & Nora Aghili
To cite this article: Rahman Hosseinzadeh, Mohammad Mavvaji, Mahmood Tajbakhsh, Zahra
Lasemi & Nora Aghili (2020): Selective Oxidation of Hydrocarbons and Alcohols Using Phen-
MCM-41 as an Efficient Co-Catalyst in Combination with NHPI-Based Nano-Magnetic Catalyst,
Organic Preparations and Procedures International, DOI: 10.1080/00304948.2020.1716434
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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
https://doi.org/10.1080/00304948.2020.1716434
EXPERIMENTAL PAPER
Selective Oxidation of Hydrocarbons and Alcohols Using
Phen-MCM-41 as an Efficient Co-Catalyst in Combination
with NHPI-Based Nano-Magnetic Catalyst
a
a
a
Rahman Hosseinzadeh , Mohammad Mavvaji , Mahmood Tajbakhsh , Zahra
b
a
Lasemi , and Nora Aghili
a
Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran;
Department of Chemistry, Firoozkooh Branch, Islamic Azad University, Firoozkooh, Iran
b
ARTICLE HISTORY Received 6 February 2019; Accepted 11 September 2019
1–2
Oxidation reactions are essential processes in organic transformations. Thus, utilization
of practical and effective methods, especially for catalytic oxidation, has attracted great
attention during recent decades. In this regard, N-hydroxy imides (NHIs), and particularly
N-hydroxyphthalimide (NHPI), have been widely applied as promising and suitable cata-
3
–4
lysts for the oxidation of organic substrates.
Since initial reports by Ishii and his co-
5–6
workers, NHPI-mediated oxidative systems have developed to become powerful catalytic
methods. Conceptually, this fosters the catalytic oxidation process through the production
of its active free-radical form, which is known as the phthalimide N-oxyl (PINO) radical.
7
Traditionally, generation of PINO radicals involves the use of co-catalysts, mainly including
8
9
10
11
such transition metal salts as Co(II), Cu(II), Mn(IV) and V(V) salts. However, in spite
of satisfactory results, employing these transition-metal complexes is not very favorable
from economic and environmental standpoints. Accordingly, metal-free catalytic systems
12
have been significantly explored over the last two decades and several effective initiators
13
or co-catalysts have been utilized such as 2, 2ꢀ- azobisisobutyronitrile (AIBN), 1,4-diamino-
14
15
2
,3-dichloro-anthraquinone, and o-phenanthroline and its analogs.
Undoubtedly, the ability to recover and reuse the catalyst is an essential topic in the
1
6–17
design of any catalytic system.
Hence, during the last years several methods have
18–24
been reported about immobilization of NHPI on solid surfaces and polymers,
well as into ionic liquids. We have recently reported the immobilization of NHPI
onto functionalized SiO coated Fe O nanoparticles, and also on NaY nano-zeolite
as
2
5–26
27
28
2
3 4
as efficient recoverable catalysts for the oxidation of benzyl alcohols and hydrocarbons.
In an innovative and useful strategy, Karimi and co-workers reported simultaneous
use of silica-immobilized NHPI together with a supported cobalt complex, in order to
29
achieve selective oxidation of methylaromatic compounds. It is obvious that applying
a similar catalytic system through a metal-free approach would be highly favorable,
especially from the viewpoint of green chemistry.
1
4–15
Accordingly, inspired by the efforts of Xu and his co-workers
and in continu-
2
7–28
ation of our attempts to extend NHPI-based heterogeneous catalytic oxidation,
in
CONTACT Rahman Hosseinzadeh
r.hosseinzadeh@umz.ac.ir
Department of Organic Chemistry, Faculty of
Chemistry, University of Mazandaran, Babolsar, Iran
ß 2020 Taylor & Francis Group, LLC

2
R. HOSSEINZADEH ET AL.
Scheme 1. Immobilization of functionalized phenanthroline onto MCM-41 (phen-MCM-41).
the present study Mobil Composition of Matter No. 41 (MCM-41) supported phenan-
throline (phen-MCM-41) was prepared as a reusable co-catalyst. In combination with
NHPI-immobilized on Fe O @SiO it constituted an effective heterogeneous system for
3
4
2
the metal-free catalytic oxidation of hydrocarbons and alcohols.
Immobilization of functionalized o-phenanthroline onto the MCM-41 was performed
according to the procedure summarized in Scheme 1. At first, to obtain the required 5-
amino-phenanthroline (3), the nitration reaction of o-phenanthroline monohydrate was
carried out by use of fuming nitric acid and sulfuric acid. Then, reduction of the corre-
sponding nitro compound (2) in the presence of 5% Pd/C and hydrazine monohydrate
led to the formation of 5-amino-1,10-phenanthroline. In the next step, 5-(N,N-bis-3-
(triethoxysilyl)propyl)ureyl-1,10-phenanthroline (phen-Si) was obtained through the
reaction of 5-amino-1,10-phenanthroline with 3-(triethoxysilyl)propyl isocyanate (4) in
ꢀ
CHCl at 80 C for 24 h. Finally, to prepare phen-MCM-41, the mesoporous MCM-41
3
reacted with phen-Si in toluene at reflux temperature for 24 h.
This co-catalyst was characterized by FT-IR, TGA, FESEM-EDX, XRD and BET tech-
niques. FT-IR spectra of the phen-MCM-41 showed characteristic peaks attributed to
the amide groups, C¼N and C¼C of phenanthroline and Si–O framework of MCM-41
30
which is in accordance with FT-IR data reported in the literature. An X-ray diffraction
(XRD) technique was utilized to survey the crystalline structure of pure MCM-41 and
phen-MCM-41 (Figure 1). In agreement with the XRD patterns of pure MCM-41, the
ꢀ
XRD pattern of the phen-MCM-41 demonstrated a strong peak at 2h of less than 3
together with some small peaks that are similar to the XRD pattern of the mesoporous
31
MCM-41 indicating the presence of MCM-41 in the co-catalyst structure. The negli-
gible shift of this peak for phen-MCM-41 may originate from the accommodation of

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
3
Figure 1. XRD patterns of the MCM-41 and phen-MCM-41.
the phenanthroline moiety inside MCM-41 channels which corresponds with the previ-
3
2–34
ous reports.
Assessment of the thermal stability, as well as the amount of immobilized organic moiety
on the surface of MCM-41 was accomplished by thermogravimetric analysis (TGA). As dis-
played in Figure 2, a weight loss of about 6% was observed at the temperature range of 50-
ꢀ
2
00 C, attributed to moisture and absorbed water. Additionally, another mass loss of ca.
ꢀ
1
8% at the range of 200-550 C arises from the degradation of the organic moiety attached
to the MCM-41. Based on this result, the amount of phen-Si immobilized on the MCM-41
surface (mmol of grafted phen-Si per 1 g MCM-41) was 0.49 mmol
Nitrogen adsorption-desorption isotherms of phen-MCM-41 at 77K are displayed in
35
Figure 3. According to the IUPAC classification, the attained isotherms of phen-MCM-41
are type IV, which refers to mesoporous materials. BET results of pure MCM-41 and
phen-MCM-41 have been summarized in Table 1. As can be seen in the table, a notable
decrease took place in the specific surface area and total pore volume for phen-MCM-41 in
comparison with the initial state, which can be accounted for by the blockage and narrow-
ing of some pores of mesoporous MCM-41 during the immobilization process.
Figure 4 shows the field emission scanning electron microscopy (FESEM) micro-
graphs of mesoporous phen-MCM-41. The average size of the phen-MCM-41 is in the
range of 50-70 nm. Furthermore, agglomeration and accumulation of the particles seems
to occur after immobilization of the organic fragment on the surface of MCM-41.
The energy dispersive X-ray (EDX) spectrum was employed for elemental analysis of
phen-MCM-41. According to the EDX pattern of phen-MCM-41 (Figure 5), the evident
Si peak confirms the presence of MCM-41 solid support in the obtained co-catalyst.
The efficiency of the catalytic system including Fe O @NHPI and phen-MCM-41 was
3
4
investigated in the oxidation reactions of hydrocarbons and alcohols (Scheme 2).
27
Considering the obtained optimum results for Fe O @NHPI, we examined the optimal
3
4
amount of phen-MCM-41 as co-catalyst. The oxidation reaction of ethylbenzene was
chosen as a model reaction (Table 2). The oxidation of ethylbenzene was carried out

4
R. HOSSEINZADEH ET AL.
Figure 2. TGA curve of the phen-MCM-41.
using different amounts of phen-MCM-41 (Table 2, entries 1-3) and Br with an aque-
2
ous solution of H O in the presence of Fe O @NHPI as catalyst, in refluxing aceto-
2
2
3 4
ꢀ
nitrile (80 C). As shown in Table 2, 15 mg of the co-catalyst seems to be sufficient to
promote the oxidation process (Table 2, entry 2, see Experimental section and reference
2
7 for scale of the reaction). Under these conditions, acetophenone was obtained as
exclusive product after 4.5 h. Additionally, utilizing a higher amount of co-catalyst
Table 2, entry 3) did not considerably change the conversion of ethylbenzene. It is
(
noteworthy that the oxidation reaction in the absence of phen-MCM-41 led to a very
low amount of conversion (Table 2, entry 4).
After that, the obtained optimal conditions were employed to oxidize a number of
organic compounds (Table 3). As shown in Table 3, under optimum conditions differ-
ent hydrocarbons were converted into the corresponding carbonyl products. As men-
tioned above, oxidation of ethylbenzene exclusively led to the formation of
acetophenone with 97% conversion (entry 1). Tetralin and indane were strikingly con-
verted to 1-tetralone and 1-indanone, respectively (entries 2-3). In these two cases, low
amounts of 1-tetralol and 1-indanol were detected as minor products. Oxidation of tolu-
ene was performed with 40% conversion and 97% selectivity toward benzoic acid (entry
4). Moreover, p-xylene was oxidized to the corresponding carbonyl compounds, com-
prising mainly terephthalic acid in conjunction with terephthaldehyde (entry 5).
Cyclohexane showed only 30% conversion with 55% selectivity in respect of cyclohexa-
none after 8 h (entry 6), along with the formation of adipic acid as the other product.
Furthermore, in order to evaluate the effectiveness of these catalytic systems for other
organic substrates, oxidations of alcohols were also investigated under these conditions.
Despite the low conversion of cyclohexanol (35% conversion with 70% selectivity for
adipic acid, entry 7), benzyl alcohol and diphenyl methanol exhibited desirable conver-
sion and selectivity (entries 8-9). Oxidation of benzyl alcohol (entry 8) resulted in 77%
conversion with 98% selectivity toward benzaldehyde, as well as slight formation of ben-
zoic acid. Diphenyl methanol successfully converted to benzophenone as the only prod-
uct (entry 9).

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
5
Figure 3. Nitrogen adsorption-desorption isotherms of the phen-MCM-41.
Table 1. BET results of MCM-41 and phen-MCM-41.
BET surface area
BJH pore
diameter (nm)
Total pore
volume (cm g
2
ꢁ1
3
ꢁ1
Sample
(m g
)
)
MCM-41
phen-MCM-41
771.43
145.58
2.34
3.62
0.46
0.36
15
From the mechanistic view, considering the work of Xu and our own previous
2
7–28
reports,
we can describe a possible route for this catalytic process (Scheme 3). At
first, interaction of phen-MCM-41 with Br results in the formation of a cation-radical
2
species which is accompanied by the subsequent proton and electron transfer between
this cation-radical and Fe O @NHPI to produce PINO radicals. The next stage involves
3
4
the abstraction of hydrogen from the substrate by PINO to convert it into a radical.
This radical readily reacts with oxygen, provided from in situ decomposition of hydro-
gen peroxide in the presence of Br , thereby leading to peroxy radicals. Eventually,
2
hydrogen abstraction by these radicals from the NHPI-based catalyst affords PINO rad-
ical and hydroperoxide which is then followed by an elimination process to achieve the
desired product.
Critical parameters in the evaluation of heterogeneous catalysis efficiency are recover-
ability and reusability. After completion of the reaction the nano magnetic catalyst was
27
readily separated by use of an external supermagnet and the separation of co-catalyst

6
R. HOSSEINZADEH ET AL.
Figure 4. FESEM images of phen-MCM-41.
Figure 5. EDX pattern of phen-MCM-41.
was then achieved via centrifugation. After several washings with ethanol and distilled
ꢀ
water, the isolated phen-MCM-41 was dried in a vacuum oven at 80 C. Subsequently,
it was ready to be employed for the next reaction. On the basis of our experimental
results, this co-catalyst could be successfully recovered and reused up to 5 times with
negligible loss of activity in respect of fresh co-catalyst (Figure 6).
In conclusion, immobilized phen-Si on MCM-41 (phen-MCM-41) together with
Fe O @NHPI was utilized as an efficient heterogeneous catalytic system to oxidize
3
4
organic substrates. The prepared phen-MCM-41 was fully characterized by FT-IR, XRD,

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
7
Scheme 2. Oxidation of ethylbenzene as model reaction for optimizing the amount of phen-MCM-41.
Table 2. Optimizing the amount of co-catalyst using oxidation reaction
of ethylbenzene.
Amount of
co-catalyst (mg)
a
b
Entry
Conv (%)
Sel (%)
1
2
3
4
a
10
15
20
–
78
97
98
5
76
100
100
62
After completion of the reaction (4.5 h), amounts of conversion and selectivity were
measured by GC-MS analysis.
b
Selectivity toward the acetophenone.
TGA, FESEM, BET and EDX analyses and exhibited considerable activity as a co-cata-
lyst in oxidation reactions of hydrocarbons and alcohols. These starting materials were
selectively converted to the corresponding carbonyl-containing products with moderate
to excellent yields. Moreover, reusability and recoverability of this heterogeneous co-
catalyst was studied. The recovered phen-MCM-41 was effectively reusable for next
runs up to 5 times with no significant effect on its co-catalytic feature.
Experimental section
1,10-Phenanthroline monohydrate, fuming sulfuric acid, 5% Pd/C catalyst and 3-(trie-
thoxysilyl)propyl isocyanate were supplied from Merck Company. Other commercially
available chemicals and solvents were purchased from local suppliers. All chemicals
were applied without further purification. MCM-41 was synthesized according to a
3
6
reported procedure.
Melting points were determined on an Electrothermal IA 9100 apparatus. H and
1
13
C
NMR spectra were determined in CDCl by means of a Bruker Avance III 400 MHz
3
spectrometer. Thermogravimetric analysis (TGA) was carried out using a Rheometric
Scientific STA-1500 instrument. Fourier transform infrared spectroscopy (FT-IR) was
accomplished on a Bruker Vector 22 spectrometer using KBr pellets. X-ray powder dif-
fraction (XRD) analyses were conducted on a Philips PW 1830 X-ray diffractometer
ꢀ
within a range of Bragg’s angle (0.8-80 ) at room temperature. Nitrogen adsorption/
desorption isotherms were recorded using a NOVA 2200e analyzer, after out-gassing
ꢀ
the samples for 14 h at 60 C under vacuum. Field emission scanning electron micros-
copy (FESEM) was performed by use of a JEOL JSM6390 instrument, equipped with an
energy-dispersive X-ray (EDX) analyzer (acceleration voltage 10 kV). Finally, products
of oxidation reactions were identified by an Agilent Technologies 7890A/5975C gas
chromatography (GC), coupled with DB-5 MS capillary column.

8
R. HOSSEINZADEH ET AL.
a
Table 3. Oxidation of hydrocarbons and alcohols using phen-MCM-41 and Fe O @NHPI.
3
b
4
b,c
Entry
1
Starting material
Major product
Time (h)
4.5
Conversion (%)
97
Selectivity (%)
100
2
3
2
85
83
94
91
2.25
d
4
7.5
6
40
39
97
54
d
5
6
8
30
35
77
97
55
70
d
7
5.5
3.5
3
8
9
a
98
100
Reaction conditions: Fe
2 mmol) in 5 mL CH
3
O
4
@NHPI (10 mg), starting material (1 mmol), phen-MCM-41 (15 mg), Br
2
(3 mol%), oxidant
ꢀ
(
3
CN at 80 C.
b
Data about the conversion of starting materials and selectivity of corresponding products were obtained by GC-
MS analysis.
c
Selectivity toward the ketone derivatives and benzaldehyde.
d
Selectivity toward the corresponding acid product.
5-Nitro-1,10-phenanthroline (2), 5-amino-1, 10-phenanthroline (3), and 5-(N,N-bis-3-
(
triethoxysilyl) propyl) ureyl-1,10-phenanthroline (phen-Si) were prepared according to
3
7
the procedure reported in the literature and these known compounds were identified
on the basis of their H and C NMR spectra, which were submitted for review.
1
13
Functionalization of MCM-41 with phen-Si (phen-MCM-41)
3
0
According to the previous report, 0.5 g of MCM-41 was suspended in 80 mL of anhyd-
rous toluene. Then, phen-Si (0.344 g, 0.5 mmol), dissolved in 8 mL of anhydrous CHCl3,
was added and the reaction mixture was stirred for 24 h under an inert atmosphere
(argon gas) at reflux temperature. Afterwards, the resulting mixture was filtered and the
obtained solid was washed several times with toluene and dried overnight under vac-
ꢁ
1
uum. IR (KBr, cm ): 2928 and 2886 (C-H stretch), 1703 (C¼O stretch), 1650 (C¼N
phenyl), 1545 (C¼C phenyl), 1088 (Si–O–Si)

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
9
Scheme 3. A plausible mechanism for the catalytic oxidation by use of Fe O @NHPI and phen-MCM-
3
4
4
1 in the presence of H O .
2 2
Figure 6. Reusability study of phen-MCM-41 for oxidation of ethyl benzene under opti-
mized conditions.
General procedure for the catalytic oxidation of benzyl alcohols and
hydrocarbons in the presence of silica coated magnetic nanoparticle supported
NHPI (oxidation catalyst) and phen-MCM-41 (co-catalyst)
Oxidation of hydrocarbons and alcohols was accomplished in a 50 ml round bottomed
flask equipped with a condenser and a mechanical stirrer. In all cases, hydrogen perox-
ide (aqueous solution 30% (w/w) of H O ) was utilized as the oxidant. Typically, to an
2
2
acetonitrile (5.0 ml) solution of ethyl benzene (1 mmol, 0.107 g) was added the catalyst
0.010 g), phen-MCM-41 (0.015 g), Br2 (0.019 mmol, 0.001 mL) and H O2 (2 mmol,
(
2
0.2 mL). Next, the reaction mixture was heated under reflux and the progress of the
reaction was monitored via TLC (silica gel, ethyl acetate:hexane 1:3) and GC. After

1
0
R. HOSSEINZADEH ET AL.
completion of the reaction, the catalyst was magnetically isolated followed by several
washings with ethanol and water. After that, the residue was centrifuged to recover the
co-catalyst (phen-MCM-41). Finally, the products were analyzed by GC–MS measure-
ments. All of the products were known compounds, identified on the basis of their GC-
MS analyses. Data and details of these GC–MS analyses were submitted for review and
are available upon request from the corresponding author.
Acknowledgments
Financial support of this work from the Research Council of the University of Mazandaran is
gratefully acknowledged.
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