Encapsulating mesoporous metal nanoparticles: Towards a highly active and stable nanoreactor for oxidative coupling reactions in water

Article abstract of DOI:10.1039/c9cc02704a

We design and prepare a highly active and stable nanoreactor via encapsulating various mesoporous metal nanoparticles with an amphiphilic hollow shell, which presents excellent performance in oxidative coupling reactions in water for efficient production of α,β-unsaturated ketones.

Full text of DOI:10.1039/c9cc02704a

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DOI: 10.1039/C9CC02704A
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Encapsulating mesoporous metal nanoparticles: Towards a
highly active and stable nanoreactor for oxidative coupling
reactions in water
Received 00th January 20xx,
Accepted 00th January 20xx
Houbing Zou,*a, b Jinyu Daib and Runwei Wang*b
DOI: 10.1039/x0xx00000x
www.rsc.org/
We design and prepare a highly active and stable nanoreactor via
Recently, mesoporous metal nanoparticles (MMNs) have
encapsulating various mesoporous metal nanoparticles with received extensive research interest and have been viewed as
amphiphilic hollow shell, which presents excellent performances in one new generation of promising nanocatalysts.18-19 Because of
oxidative coupling reactions in water for efficient production of α, the ultrathin subunits and highly open structures, MMNs can
β-unsaturated ketones.
provide high-density of active sites inside the particles and fast
mass transports for reactants, thereby exhibiting unexpected
catalytic performances.20-23 Interestingly, it seems that the
activities of MMNs don’t have a distinct relationship with their
particle size, because the bulky particles can also offer high-
density of accessible active sites.24 Moreover, owing to the
structural robustness, MMNs often possess superior catalytic
stabilities even under harsh reaction conditions. Obviously,
incorporating MMNs into a hollow porous shell can result in a
perfect nanoreactor. When varying the particle sizes of MMNs
can accurately adjust the metal loading amount, the hollow
porous shell can provide a unique reaction microenvironment
for MMNs to further enhance the catalytic activities and
stabilities. However, such a perfect nanoreactor has been never
reported so far, due to the great difficulty in implanting MMNs.
Encapsulating metal nanoparticles (NPs) with hollow structured
materials have been widely used to construct nanoreactors for
various catalysis applications.1-5 Owing to the fascinating
confinement effect, the catalytic activities and stabilities of the
metal NPs can not only be significantly enhanced,1-7 but also
their selectivities can be precisely tuned via adjusting the
interior reaction microenvironment.8-10 While numerous of
nanoreactors are continuously developed for different
reactions such as hydrogenation,11-12 oxidation13-14 and even
cascade reactions,15-17 they can be generally classified into the
single-site nanoreactors or the multi-sites nanoreactors
(Scheme 1). Because one hollow shell encapsulates one metal
NP, the single-site nanoreactors often present high catalytic
stabilities yet low metal loading amount that is very important
for practical applications. The relatively large particle sizes also
lead to low catalytic activities. In contrast, since one hollow shell
encapsulates many tiny metal NPs, the multi-sites nanoreactors
usually display high catalytic activities and high metal loading
amount. However, due to the aggregation and sintering of the
tiny metal NPs under harsh reaction conditions, low catalytic
stabilities are always accompanied with the multi-sites
nanoreactors. Therefore, it is still desirable to develop perfect
nanoreactors comprising controllable metal loading amount,
high catalytic activities and stabilities for exploring their
practical applications.
a. School of Chemistry and Chemical Engineering, Shanxi University, 92 Wucheng
Road, Taiyuan, 030006, P. R. China, E-mail: zouhb@sxu.edu.cn
b. State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of
Chemistry, Jilin University, 2699 Qianjin Street, Changchun, 130012, P. R. China,
E-mail: rwwang@jlu.edu.cn
† Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
Scheme 1 Schematic illustration for previously reported single-
site nanoreactor and multi-sites nanoreactor as well as
assembled-multisites nanoreactor developed in this work.
This journal is © The Royal Society of Chemistry 20xx
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In this work, we report a novel assembled-multisites nanoreactor YS-mesoPd@PMO was obtained. ForVcieowmArtpicalerOisnolinne,
nanoreactor composed of a MMN and an amphiphilic hollow we also prepared the single-site nanorDeOaIc:t1o0r.10Y3S9-/sCs9PCdC@02P7M04OA
porous shell (Scheme 1), prepared via a simple “ship in bottle” and the multi-sites nanoreactor YS-ssPd@PMO via previous
growth strategy. Using different metal precursors and reports.
structure-directing agents (SDA), we can obtain a series of such
According to the sanning/transmission electron microscopy
nanoreactors containing different MMNs (Pd, Pt, Rh). Although (SEM/TEM) images (Fig.1b-c), the sample YS-mesoPd@PMO
this nanoreactor contains only one metal NP, robust MMNs can shows a similar particle size and a shell thickness with that of
still provide abundant and stable enough accessible active sites YS-Au@PMO, indicating that the process of introducing MMNs
inside the particle, leading to an integration of high activities has very little impact on the yolk-shell structures. It is also clear
and high stabilities as well as controllable metal loading amount. from these images that one hollow shell exactly encapsulates
Using the oxidative coupling reaction as a model reaction, we one metal nanoparticle and any extra Pd species can not be
find that this assembled-multisites nanoreactor, as expected, observed in the sample. The high-magnification TEM image
exhibited much higher activity than that of previous single-site (Fig.1d) distinctly displays that the Pd species are grown on the
nanoreactor and much higher stability than that of previous surface of Au NPs, forming a core-shell structure. This suggests
multi-sites nanoreactor.
that the Au NPs play an important role in our “ship in bottle”
strategy. From the high-resolution TEM (HRTEM) and high-angle
annular dark-fileld scanning TEM (HAADF-STEM) image (Fig.1e-
f), we can clearly observe that there are numerous of
mesochannels in every Pd shell. The EDX elemental mapping
reveals a core-shell structure of metal NPs, further confirming
that the mesoporous Pd is indeed grown on the surface of Au
NPs. The X-ray diffraction (XRD) pattern exhibits two sets of
diffusion peaks (Fig.S2b), which can be attributed to the fcc Au
and fcc Pd, respectively. The Pd 3d X-ray photoelectron
spectroscopy (XPS) spectrum (Fig.S2c) shows two visible peaks
at 336.9 eV and 341.8 eV assigned to Pd 3d5/2 and Pd 3d3/2
,
proving that the surface Pd is mainly in the metallic state. The
small-angle XRD (Fig.S2a) and nitrogen sorption analysis
(Fig.S2d) suggest a uniform mesoporous structure in the PMO
shell that can provide an efficient passageway for the mass
transfer of reactants and products. Based-on the inductively
coupled plasma (ICP) analysis, the loading amount of metal Pd
is calculated to be about 5.0 wt%.
Next, we attempted to tune the metal loading amount by
adjusting the particle size of MMNs. Combined the ICP analysis
with the TEM images (Fig.S3), the Pd loading is gradually
increased from 5.0 wt% to 9.6 wt% and 14.5 wt% along with an
increase of particle diameter from 40 nm to 50 nm and 60 nm.
Additionally, the current synthetic method is extended to
introduce other MMNs into the hollow shell. As shown in the
Fig.S4, when we use the RhCl3/H2PtCl6 as the metal precursor
and the surfactant cetyltrimethylammonium bromide (CTAB) as
the SDA, the similar assembled-multisites nanoreactor YS-
mesoPt@PMO and YS-mesoRh@PMO can be obtained. All
above results clearly demonstrate that we can successfully
implant various MMNs into hollow nanoreactors via this facile
“ship in bottle” strategy.
Aerobic oxidative coupling reaction is gradually recognized as
an efficient and economic route for production of fine
chemicals.28 Diverse imines and amides have been synthesized
from alcohols and amines using various homogeneous and
heterogeneous catalysts via a typical oxidation-condensation
cascade reaction.29-30 While some achievements are realized,
sustainable aerobic oxidative coupling process under green
conditions has been still rarely reported for producing α, β-
unsaturated ketones from alcohols and ketones. In present
study, the catalytic performance of the designed nanoreactor
Fig.1 (a) Illustration for the fabrication of the assembled-
multisites nanoreactor YS-MMNs@PMO. (b) SEM image, (c-d)
TEM images, (e) HRTEM image, (f) HAADF-STEM image and (g-j)
EDX elemental mapping of the sample YS-mesoPd@PMO.
The assembled-multisites nanoreactor was prepared via a
general “ship in bottle” growth strategy, illustrated in Fig.1a.
Firstly, yolk-shell structured Au@mesoporous organosilica
nanospheres (YS-Au@PMO) with an amphiphilic shell (Fig.S1)
were prepared based on our previous reports.25-26 Then a
typical coassembly-reduction process was conducted to grow
MMNs inside the Au@PMO nanospheres. To load mesoporous
Pd, surfactant hexadecylpyridinium chloride (HDPC), Na2PdCl4
and ascorbic acid (AA) were used as the SDA, the metal
precursor and the reductant, respectively. Because of the
uniform mesochannels in PMO shell, the aforementioned
molecules could liberally diffuse into the hollow cavities and
assemble to micelle composites. Once introducing a weak
reductant (AA) into the synthetic system, mesoporous Pd NPs
were formed. Since the Au NPs offered a site for heterogeneous
nucleation that needs lower energy than homogeneous
nucleation,27 all mesoporous Pd were grown on their surfaces
via an epitaxial growth pattern. After removing the surfactant
via extracting in acid ethanol solution, the assembled-multisites
2 | J. Name., 2012, 00, 1-3
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Table 1 Results of the aerobic oxidative coupling reaction Table 2 Aerobic oxidative coupling of diffirent alcohols and
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catalyzed by different catalystsa
ketones catalyzed by the assembled-mulDtiOsiIt:e10s.1n0a3n9o/Cre9CaCct0o2r70Y4SA-
mesoPd@PMOa
O
O
O
OH
catalyst H2O
open air base 80 o
+
O
C
OH
MeO
R2
catalyst
open air
R2
MeO
H2O
R1
+
R1
℃
base
80
H3C
Entry
Catalyst
Conv. (%)b
Sel. (%)c
1
2
3
4
5
6
7
8
Pd/MCM-41
YS-Au@PMO
53.2
18.5
76.5
99.9
99.9
99.9
83.6
84.8
98.6
99.5
98.6
96.8
95.7
Entry Substrate
Product
Time Conv./Sel.(%)b
O
OH
YS-ssPd@PMO
1
2
3
4
5
10 h
10 h
10 h
12 h
12 h
99/96
99/98
99/97
98/92
95/96
YS-ssPd@PMOd
YS-msPd@PMO
88.3 (10.5e)
97.3
O
OH
OH
OH
YS-mesoPd@PMO (5 wt%)
mesoPd NPs
98.9
99.3
98.2
99.1
92.3
99.0
Me
Me
mesoPd NPs+HPMOf
YS-mesoPd@PMO-9.6 wt%
O
O
9
10
11
12
YS-mesoPd@PMO-14.5 wt% 95.6
MeO
MeO
YS-msPd@PMOg
56.9
95.9
YS-mesoPd@PMOg (5 wt%)
a
Cl
Reaction condition: 4-methoxybenzyl alcohol (0.5 mmol),
K2CO3 (1.5 mmol, 3 equi), 3.0 mL of H2O, 1.0 mL of acetone,
catalyst (Pd 1.5 mol%), open air, 10 h.
products were analyzed and identified by GC-MS. Reaction
time: 15 h. e Selectivity of the over-oxidation product. f Physical
mixture of the mesoPd NPs and hollow structurted PMO
(HPMO). g The fifth recycled catalyst.
Cl
O
OH
b, c
Catalytic reaction
d
F
F
O
OH
6
7
8
9
16 h
16 h
12h
92/99
98/97
96/98
83/95
O2N
O2N
O
OH
YS-mesoPd@PMO is evaluated in the oxidative coupling of 4-
methoxybenzyl alcohol and acetone using water as the solvent
and air as the oxidizing agent. The results are shown in Table 1.
Using the conventional MCM-41 supported Pd NPs as the
catalyst (Entry 1), a conversion of only 53.2 % is obtained in 10
h. In sharp contrast, our prepared nanoreactor YS-
mesoPd@PMO presents a conversion of ≥ 99% with a selectivity
of 97.3% under the same reaction conditions (Entry 6). This
excellent performance is comparable to the activity realized
using toluene as an organic solvent and oxygen as an oxidzing
agent.31-32 Considering that the sample YS-Au@PMO is unactive
(Entry 2), the superior activity of YS-mesoPd@PMO should be
mainly attributed to their mesoporous Pd species. Then we
examine the catalytic power of the sample mesoPd NPs
prepared by removing the PMO hollow shell using 2 M NaOH
solution. It is found that the activity of both mesoPd NPs and
physical mixture of mesoPd NPs and hollow structured PMO
(HPMO) is still lower than that of YS-mesoPd@PMO (Entry 7-8).
This result indicates that the amphiphilic hollow shell also plays
a positive role in improving the catalytic activity via enriching
hydrophobic reactants.25 Moreover, our YS-mesoPd@PMO is
more active than the single-site nanoreactor YS-ssPd@PMO
(Fig.S5), which only gives a conversion of 76.5% (Entry 3) and
needs 15 h to completely transform the reactant (Entry 4). The
lower activity of YS-ssPd@PMO is possible due to the large
particles size of Pd NPs that offer limited surface active sites. On
the other hand, although the multi-sites nanoreactor YS-
msPd@PMO (Fig.S6) shows a high conversion of 99.9% (Entry 5),
the high surface activity of the tiny Pd NPs leads to the
formation of over-oxidation product,33 presenting a lower
selectivity towards oxidative coupling product. It is
O
O
OH
OH
Ph
12 h
a
Reaction condition: alcohol (0.5 mmol), K2CO3 (1.5 mmol, 3
equi), 3.0 mL of H2O, 1.0 mL of ketone, catalyst (Pd 1.5 mol%),
b
open air. Catalytic reaction products were analyzed and
identified by GC-MS.
worth noting that the YS-mesoPd@PMO with higher metal
loading also exhibit a similar catalytic activity (Entries 9-10), in
spite of the large particle size of their mesoPd NPs (Fig.S3).
Furthermore, we study the catalytic stabilities of both the
assembled-multisites nanoreactor YS-mesoPd@PMO and the
multi-sites nanoreactor YS-msPd@PMO. After being reused for
five times, the YS-mesoPd@PMO still exhibits an excellent
catalytic performance with a conversion of ≥ 95% and a
selectivity of ≥ 98% (Entry 12, Fig.S7). In sharp contrast, only
56.9% of the pristine activity can be remained for the catalyst
YS-msPd@PMO after five recycling runs (Entry 11, Fig.S7). We
use ICP to analyze the liquid phase of the reaction mixtures
collected after the fifth run, and find that only ppm Pd species
can be detected in both of the liquid phases. This result reveals
that the Pd leaching is negligible in both of catalysts, which is
often observed for nanoreactor catalysts. Then we characterize
the recovered catalysts after the fifth reaction. The TEM images
(Fig.S8a-b) clearly reveal that there is no distinct variation on
the yolk–shell nanostructure and the mesoporous structure of
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J. Liu, S. Qiao, J. Chen, X. Lou, X. Xing and G. Lu, Chem.
MMNs for the recovered YS-mesoPd@PMO. The Pd 3d XPS
spectrum also indicates that the Pd is still mainly in the metallic
state (Fig.S8c). This result strongly suggests that the robust
structural stability of mesoPd NPs is favorable for the superior
catalytic stability. However, for the recovered catalyst YS-
msPd@PMO, severe sintering of tiny Pd NPs is observed and the
particle size grows from 4 nm to 8 nm (Fig.S9), which should be
responsible for the significant activity loss. Combining all above
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5
6
7
8
9
results,
the
assembled-multisites
nanoreactor
YS-
mesoPd@PMO can integrate the high catalytic activity of the
multi-sites nanoreactor YS-msPd@PMO with the high catalytic
stability of the single-site nanoreactor YS-ssPd@PMO.
Finally, the substrate scope of current catalyst system is
investigated and the results are summarized in the Table 2. We
firstly examine the benzyl alcohols with different substituted
groups including electron-donating -CH3 and electron-
withdrawing -Cl, -F, -NO2. All these alcohols can be efficiently
coupled with acetone for producing the corresponding α, β-
unsaturated ketones with a yield of ≥ 91% (Entries 1-6) and it
seems that the substrate with an electron-withdrawing group
needs more time to completely convert the reactant (Entries 4-
6). Moreover, less active 1-naphthylmethanol is also tested for
oxidative coupling with acetone and a high yield of 95% is
obtained in 16 h (Entry 7). In addition, different ketones is
examined to couple with benzyl alcohol and it is found that the
butanone show a similar activity with acetone (Entry 8) while
only a considerable yield is obtained using acetophenone as the
coupling agent (Entry 9). All these catalytic results verify a high
versatility of our nanoreactor YS-mesoPd@PMO.
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To conclude, we design and prepare a new class of
assembled-multisites nanoreactor via encapsulating various
MMNs in an amphiphilic hollow shell. Because the MMNs not
only provide high-density of accessible active sites inside
particles but also possess robust structural stability, the
developed nanoreactor can integrate high catalytic activities
and high catalytic stabilities as well as controllable metal
loading. In the oxidative coupling of alcohols and ketones under
extremely sustainable reaction conditions, the catalyst exhibits
an excellent activity and stability, much higher than that of
previously reported nanoreactors. This work not only develops
a sustainable route for one-pot producing α, β-unsaturated
ketones but also provides a new platform for designing
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This work was supported by National Natural Science
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gratitude to the test platform provided by Shanxi University of
scientific Instrument Center.
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Conflicts of interest
There are no conflicts to declare.
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DOI: 10.1039/C9CC02704A
We design and prepare a highly active and stable nanoreactor by encapsulating mesoporous metal
nanoparticles for efficient production of α, β-unsaturated ketones via a one-pot oxidative coupling
reaction.