Silicon Carbide Supported Palladium-Iridium Bimetallic Catalysts for Efficient Selective Hydrogenation of Cinnamaldehyde

Article abstract of DOI:10.1002/cjoc.201900299

Selective hydrogenation of α,β-unsaturated carbonyls into saturated carbonyls is important to obtain remunerative products. However, it is still a challenge to achieve high activity and selectivity under mild conditions. Herein, Pd, Ir and bimetallic Pd-Ir nanoparticles were uniformly deposited with high dispersity on the surface of SiC by a facile impregnation method, respectively. The as-prepared Pd/SiC catalysts efficiently hydrogenate cinnamaldehyde to hydrocinnamaldehyde at room temperature and atmospheric pressure, and the activity of Pd/SiC is observed further enhanced by adding Ir component (conversion of 100%). In addition, the dependence of Pd-Ir catalyst activity on Pd/Ir molar ratio confirms a synergistic effect between Ir and Pd, which originates from the electron transfer between Pd and Ir.

Full text of DOI:10.1002/cjoc.201900299

Chinese Journal
of Chemistry
CJC 中 国 化 学 - An International Journal
Accepted Article
Title: Silicon Carbide Supported Palladium-Iridium Bimetallic Catalysts for Efficient
Selective Hydrogenation of Cinnamaldehyde
Authors: Penghui Li, Yingyong Wang, Yunwei Wang, Guoqiang Jin, Xiang-Yun Guo,
and Xili Tong*
This manuscript has been accepted and appears as an Accepted Article online.
This work may now be cited as: Chin. J. Chem. 2020, 38, 10.1002/cjoc.201900299.
The final Version of Record (VoR) of it with formal page numbers will soon be
published online in Early View: http://dx.doi.org/10.1002/cjoc.201900299.
ISSN 1001-604X • CN 31-1547/O6
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Chinese Journal
of Chemistry
中 国 化 学 - An International Journal
Catalytic transfer hydrogenation, Silicon carbide, Alloyed
Palladium-Iridium nanoparticles, Synergistic effect
Concise Report
CJC
Silicon Carbide Supported Palladium-Iridium Bimetallic Catalysts for
Efficient Selective Hydrogenation of Cinnamaldehyde
Penghui Li,a,b Yingyong Wang, Yunwei Wang, Guoqiang Jin, Xiang-Yun Guo, and Xili Tong*,a
a
a
a
a,c
a
State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, Shanxi, China
b
Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
c
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, China
Cite this paper: Chin. J. Chem.2019,37, XXX—XXX.DOI: 10.1002/cjoc.201900XXX
Summary of main observation and conclusion Selective hydrogenation of α, β-unsaturated carbonyls into saturated carbonyls is important to obtain
the remunerative products. However, it is still a challenge to achieve the high activity and selectivity under mild conditions. Herein, Pd, Ir and bimetallic
Pd-Ir nanoparticles were uniformly deposited with high dispersity on the surface of SiC by a facile impregnation method, respectively. The as-prepared
Pd/SiC catalysts efficiently hydrogenates cinnamaldehyde to hydrocinnamaldehyde at room temperature and pressure, and the activity of Pd/SiC are
observed further enhanced by adding Ir component (conversion of 100%). In addition, the dependence of Pd-Ir catalyst activity on Pd/Ir molar ratio
confirms a synergistic effect between Ir and Pd, which originates from the electron transfer between Pd and Ir.
Background and Originality Content
Selective hydrogenations of α, β-unsaturated carbonyls are
very important processes because they can produce a large
number of fine chemicals, pharmaceuticals and food ingredients
Scheme 1 Reaction pathways for the hydrogenation of cinnamaldehyde
(CAL)
[1–3]
.
Cinnamaldehyde (CAL), one of the representative α,
β-unsaturated aldehydes, is widely studied in the
semi-hydrogenation to produce cinnamyl alcohol (COL) and
hydrocinnamaldehyde (HALD) (Scheme 1). HALD has attracted
extensive attentions in the manufacture of perfumes and
pharmacies. For example, HALD is an important intermediate in
H2
O
OH
Cinnamaldehyde
Cinnamyl alcohol (COL)
(CAL)
H2
2
[4]
the synthesis of pharmaceuticals for the treatment of HIV
.
H
Although ethenyl groups (C=C) are easier to be hydrogenated
than carbonyl groups (C=O) in thermodynamics, the conjugation
effect between the benzene ring, vinyl groups and carbonyl
groups usually results in the production of a mixture containing
H2
O
OH
[5–8]
HALD, COL and hydrocinnamyl alcohol (HALC)
. Additionally,
Hydrocinnamaldehyde (HALD)
Hydrocinnamyl
alcohol (HALC)
high temperature and pressure could improve the activity of
hydrogenation toward C=C, but simultaneously increase the
possibility of mixed product. Therefore, it’s still highly desired
but a challenge to achieve efficient and selective hydrogenation
of CAL to HALD at mild condition.
Pd is well known to be active for C=C hydrogenation but inert
for C=O hydrogenation, thus it is usually employed as the main
active metal for the hydrogenation of CAL to HALD
[9–11]
. To
further improve the performance of Pd-based catalysts, different
additives are usually applied. For example, Fu’s group reported
that the addition of tungsten nitridecan obviously improve the
activity and selectivity of Pd/SBA-15 for CAL hydrogenation to
[12]
HALD . Besides, addition of a secondary metal component has
also exhibited a promising potential to optimize the catalytic
performance via potential synergistic effects between two
[13, 14]
metals
. On the other hand, the catalytic hydrogenation of
CAL to HALD often employs hydrogen-donor molecules (such as
isopropanol, formate and et al) as the hydrogen source through
catalytic transfer hydrogenation mechanism. As Katho et al.
This article has been accepted for publication and undergone full peer review but has not been
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10.1002/cjoc.201900299
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Concise Report
Li et al.
reported, the hydrogenation of CAL to HALD took place on the
surface of rhodium-sulfonated triphenylphosphine catalysts
using formate as hydrogen source at 70 °C with high turnover
electron-transfer between Pd and Ir can increase the catalytic
performance.
[15]
frequency . In the case of Pd-based catalysts, this reaction can
directly employ H as the hydrogen source, which is more
Results and Discussion
Enhanced activity of Pd/SiC for transfer hydrogenation of
CAL by Ir addition
2
attractive for commercial applications due to huge reserve of
hydrogen gas. For example, Pham-Huuet al. identified the
hydrogenation of CAL to HALD occurred on the surface of
Pd/carbon nanofiber and Pd/charcoal catalysts with hydrogen
For the selective hydrogenation of α, β-unsaturated carbonyls at
C=C bonds, Pd is always considered as the suitable parent active
metal. Isopropanol was the hydrogen source and solvent, and
the presence of KOH is helpful to the release of hydrogen from
[9]
stream continuously feeding
.
The design of supports is another issue to strengthen the
catalytic performance of Pd-based catalysts. Carbon supports
were applied to anchor or disperse Pd-based catalysts, however
carbon supported nano-metallic catalyst have a tendency of
self-ignition and even explosion in the reaction. Recently, high
specific surface area β-SiC has been supposed as a potential
support alternatives to carbon materials due to its stable
chemical property, high mechanical strength and good thermal
[24]
isopropyl alcohol to promote the hydrogenation reaction
.
Under our experimental conditions, Pd/SiC showed the
conversion of 34.7% for CAL hydrogenation to HALD after 1.5 h
at 298 K, whereas Ir/SiC only converted 0.6% under the same
conditions (Table 1, entries 2 and 1). Thus, the catalytic activity
of monometallic Ir for the reaction is poor. It is somewhat
surprising that the bimetallic catalysts after incorporated Ir into
Pd/SiC showed markedly enhanced activity for CAL
hydrogenation to HALD (entries 3-5). Especially, the PdIr/SiC
catalyst with the molar ratio between Pd and Ir of 1:1 exhibited
the highest conversion of 100% (entry 4). Thus, it is obvious that
metallic Ir plays an important role in enhancing the activity of Pd
catalysts, indicating a synergistic effect occurred between Ir and
Pd in the bimetallic catalysts. Since the PdIr/SiC catalyst
displayed the best performance among the Pd-Ir alloy with
different ratios, it was rational selected out to further evaluate in
detail.
[16, 17]
conductivity
. In the previous researches, we found that the
electron transfer occurred between metals and SiC caused by
Mott-Schottky effect, which can significantly tune the activity
[18-23]
and selectivity of SiC-supported metallic catalysts
.
Inspired by the above-mentioned demonstration, β-SiC with
large surface area supported Pd-Ir bimetallic catalyst was
constructed by a facile impregnation method. Compared with
Pd/SiC and Ir/SiC catalysts, bimetallic PdIr/SiC exhibited an
obviously enhanced catalytic performance for the hydrogenation
of CAL to HALD. Besides, the molar ratio between Pd and Ir took
an important role on the catalytic performance, identifying the
Table 1 Catalytic transfer hydrogenation (CTH) of cinnamaldehyde (CAL) a
Total metal Conv. of CAL
Select. of
HALD (%)
86.9
Entry
Catalyst
loading (w %)
3
(%)
0.6
1
2
3
4
5
Ir/SiC
Pd/SiC
3
34.7
89.7
100
99.4
98.1
99.2
99.5
Pd
PdIr/SiC
PdIr /SiC
3
Ir/SiC
5.5
5.5
5.5
3
80.5
a
Reaction conditions: cinnamaldehyde (0.8 mmol), isopropanol (10 ml), KOH isopropyl alcohol solution(0.01 mol/L, 2 mL), catalyst (30 mg), 298 K, 1.5 h.
of COL is produced under identical conditions (entry 2). The
temperature of Pd-Au/C catalyst is slightly lower (entry 13),
though, the selectivity to HALD is just 65% when CAL is
Comparison with other Pd-based catalysts
The outstanding performance of the PdIr/SiC catalyst is
highlighted by the comparison with the reported Pd-based
catalyst in hydrogenation of CAL to HALD (Table 2). Noted that
the reaction conditions are different in every case listed in table 2.
Obviously, the catalyst of PdIr/SiC shows a prominent advantage
in selective hydrogenation of CAL to HALD under mild conditions.
Compared with the transfer hydrogenation, the conversion of
2 3
completely converted. The catalyst of Pd/ƴ-Al O has a high
selectivity (entry 14), however, the reaction conditions are
harsher. Above all, the PdIr/SiC catalyst is one of the best
candidates in efficiently selective hydrogenation of CAL toward
HALD at room temperature and pressure.
2
direct hydrogenation employed H is lower and a small quantity
Table 2 Comparison of the catalytic performance of supported Pd-based catalysts for cinnamaldehyde hydrogenation
Time
Conv. of
CAL (%)
Select. of HALD
(%)
Entry
Catalyst
T (°C)
P(H
2
)/MPa
Reference
Year
(h)
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Chin. J. Chem. 2019,37, XXX－XXX
This article is protected by copyright. All rights reserved.

Selective Hydrogenation of Cinnamaldehyde
Chin. J. Chem.
1
2
3
4
5
6
7
8
9
PdIr/SiC
PdIr/SiC
25
25
isopropanol
1.5
1.5
2
100
70
99.2
91.2
84.5
81
This work
2019
2019
2018
2018
2016
2016
2016
2015
2015
2014
2014
2014
2014
2013
2010
2005
0.3
1
This work
Pd/MCM-41
110
100
40
61.2
56
25
14
12
26
27
28
29
30
31
4
Au50Pd50/TiO
Pd-WN/SBA-15
Pd/La CO -NRs
Pd-Au/CeO
2
-300
0.1
1
1.5
2
99.5
100
93
97.6
86
O
2 2
3
80
0.1
1
3
2
50
18
2
85
Pd-CNT/AC
Pd@TNT
70
1.5
0.5
4
87
82
30
1.6
1
50
80
1
0
1
2
3
4
5
6
Pd/Al O
2 3
50
40
88
1
1
1
1
1
1
Pd/ZIF
Pd/C
40
2
6
>99.9
62
90.4
72
60
0.2
0.1
2
1
Pd-Au/C
Pd/γ-Al
22
1
100
99
65
4
2
O
3
100
40
3
94
32
11
33
AuPd-OMC
Pd/MWNTs
1
11
25
97
88
80
0.1
100
81
Catalyst characterization
SiC (111)
The phase composition of catalysts was investigated by X-ray
diffraction (XRD), and the results are showed in Fig. 1 (XRD
patterns of other Pd-Ir bimetallic catalysts seen in Fig. S1). In the
XRD patterns of Ir/SiC, all the prominent diffraction peaks are
SiC (220)
SiC (311)
SiC (222)
Stacking
fault
SiC (200)
Ir/SiC
[20]
assigned to cubic SiC , and no observable peaks corresponding
to Ir metal are detected. This could be ascribed to the small
particle size and high dispersion of Ir on the SiC surface. The
diffraction peaks at 40.06° and 46.58° in the patterns of
Pd/SiC are identified to Pd (111) and (200), respectively. For
PdIr/SiC catalyst, the diffraction peaks of Pd (111) and (200) shift
to 40.13° and 46.66°, indicating that there is some interaction
40.13
46.66
PdIr/SiC
[34]
between Ir and Pd
.
40.06
46.58
Pd/SiC
0
Pd (111)
40
Pd (200)
2
30
50
60
70
80
2
theta (°)
Figure 1 XRD patterns of Ir/SiC, PdIr/SiC and Pd/SiC.
Chin. J. Chem. 2019,37, XXX－XXX
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Concise Report
Li et al.
2+
and the peaks at 336.39 and 341.88 eV correspond to Pd species
[
12]
.
For PdIr/SiC catalyst, however, all of these peaks shift toward
0
higher binding energies, 335.84 and 341.14 eV for Pd , 336.68 and
3
donation of Pd. From Fig. 3B, the binding energies of Ir in Ir/SiC
2+
42.17 eV for Pd , respectively. These results indicate an electron
0
[35]
are 61.31 and 64.28 eV for Ir 4f7/2 and 4f5/2 respectively
whereas these values in PdIr/SiC have decreased to 61.04 and
4.03 eV respectively. The decrease of the binding energies
,
6
suggests an increase in the electron density of Ir. Also, the binding
energy values of iridium oxide are listed in Fig. 3B. The XPS results
confirm the electron transfer from Pd to Ir. The decrease of Pd
electron density is helpful to the adsorption of C=C on Pd active
sites due to the lower repulsion interaction between Pd and C=C
[36]
bond
.
Figure 2 TEM images of Ir/SiC (A), Pd/SiC (B), PdIr/SiC: The inset is HRTEM
image (C); HAADF-STEM of PdIr/SiC for elemental mapping (D).
To investigate the morphology of the catalysts, the HRTEM
analysis was conducted and the results are shown in the Fig. 2. Ir
nanoparticles with the average size of 2.1 nm (Fig. 2A) and Pd
nanoparticle with the average size of 3 nm (Fig. 2B) were
uniformly deposited on the surface of SiC, no aggregation were
found. From Fig. 2C, metallic nanoparticles are uniformly
dispersed on the SiC surface with an average size of 4.6 nm, and
the interplanar spacing of 0.223 nm in the inset probably
corresponds to the (111) crystal face of PdIr alloy nanoparticle.
The microstructure of PdIr/SiC was further examined by
HAADF-STEM. The typical STEM image within a randomly selected
area and the element mapping of Ir and Pd (Fig. 2D) show that the
metal Ir and Pd are homogeneously distributed in each
nanoparticles. Thus, combined with above results, the two metals
could have formed alloyed nanoparticles; however, the mixture of
two different monometallic phase cannot be ruled out.
Figure 3 XPS spectra of Pd in Pd/SiC and PdIr/SiC (A); Ir in Ir/SiC and
PdIr/SiC (B).
General applicability
To investigate the versatility of PdIr/SiC catalyst, various α,
β-unsaturated carbonyls were tested, and the reaction results are
summarized in Table 3. From entries 1 and 2, PdIr/SiC exhibits
high activity and selectivity toward the hydrogenation of
unsaturated aldehydes with methoxy and amino groups. In
addition, the catalyst also shows effective hydrogenation
capability for the vinyl group in unsaturated ketones and esters
(entries 3 and 4). For the hydrogenation of 2-furyl acrolein (entry
5), both the activity and selectivity of the catalyst decrease slightly,
and this might be influenced by different conjugation interactions.
Fig. 3 displays the XPS results of Pd/SiC, Ir/SiC and PdIr/SiC
(
XPS spectra of other Pd-Ir bimetallic catalysts seen in Fig. S2). For
0
Pd/SiC, the peaks at 335.64 and 340.96 eV are ascribed to Pd ,
Table 3 Selective hydrogenation of various unsaturated aldehydes over the PdIr/SiC a
Entry
Substrate
Product
Conv. /%
83.6
Select. /%
97.8
O
N
O
N
1
O
O
O
O
2
95.0
98.9
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Chin. J. Chem. 2019,37, XXX－XXX
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Selective Hydrogenation of Cinnamaldehyde
Chin. J. Chem.
O
O
3
4
99.9
99.9
O
O
O
O
98.5
82.6
99.7
76.6
O
O
5
O
O
a
Reaction conditions: substrate (0.8 mmol), isopropanol (10 ml), KOH isopropyl alcohol solution (0.01 mol/L, 2 mL), catalyst (30 mg), 298 K, 1.5 h.
Stability
The stability of PdIr/SiC catalyst was investigated for the Experimental
reaction of selective hydrogenation of CAL to HALD under
conditions of approximately half conversion. From Fig. 4, there is
no evident loss in the catalytic activity and selectivity. After the
fifth run, the conversion and selectivity was maintained at 52%
and 96.6% respectively. In a word, the stability of PdIr/SiC catalyst
is reliable in the reaction of selective hydrogenation of CAL to
HALD.
Catalyst preparation
β-SiC support with a specific surface area of ~50 m /g was
2
[
37]
prepared by a sol-gel and carbothermal reduction process
.
Catalysts were prepared by conventional co-impregnation
method. The metal content of all PdIr bimetallic catalysts with
different molar ratios of Pd to Ir was fixed at around 5.5 w%. For
preparing PdIr/SiC, 1.7 ml of PdCl
2
aqueous solution (10 mg/ml)
and 14.2 ml of IrCl (2 mg/ml) ethanol solution were dissolved in
3
ethanol, then 472 mg of SiC support was dispersed in the above
solution under sonication. The suspension was vaporized in air at
3
33 K for 10 h under magnetically stirring, and then the dried
catalyst was put into vacuum oven at 318 K overnight. After that,
the catalyst was calcined at 623 K for 3 h in muffle furnace. Before
reactions, the catalyst was reduced in flowing H
vol.% Ar) for 90 minutes at 573 K. For comparison, Pd/SiC (Pd w%
3), Ir/SiC (Ir w% = 3), PdIr /SiC, Pd Ir/SiC were also prepared in
2 2
(5 vol.% H , 95
=
3
3
the same method.
Catalyst test
Catalyst test experiments were carried in a 50 ml stainless
steel autoclave under Ar atmosphere. The autoclave was fed with
isopropyl alcohol (Sinopharm, 10 ml), CAL (Aladdin, ≥99.5%, 0.8
mmol), KOH isopropyl alcohol solution (2 ml, 0.01 mol/L) and
catalyst (30 mg). Then the reactant suspension was stirred at 600
rpm and kept at 298 K for 1.5 h. After reactions, the filtrate was
collected for analysis by GC-MS (Bruker SCION SQ 456GC-MS,
Germany).
Figure 4 Recycling stability of PdIr/SiC catalyst in five cycles. Reaction
conditions: 30 mg PdIr/SiC, 0.8 mmol CAL, 10 mL isopropanol, 2 ml KOH
isopropyl alcohol solution (0.01 mol/L), 298 K, 45 min.
Catalyst characterization
X-ray diffraction (XRD) patterns were recorded in the range of
2θ from 20° to 80° by a Rigaku D-Max/RB X-ray diffractometer
with Cu Kα radiation (40 kV, 30 mA) at a scanning rate of 2°/min.
The microstructure of catalysts was investigated by TEM
equipped with high-angle annular dark-field (HAADF) attachment
on a JEOL-2100 transmission electron microscope with an
acceleration voltage of 200 kV. X-ray photoelectron spectroscopy
Conclusions
In summary, efficiently selective hydrogenation of
cinnamylaldehyde to hydrocinnamaldehyde has been achieved by
using SiC supported bimetallic Pd-Ir nanoparticles as the catalyst
at room temperature. The bimetallic PdIr nanoparticles can
remarkably enhance the catalyst activity due to the electron
transfer from Pd to Ir on the surface of SiC. The PdIr/SiC catalyst
exhibits general applicability for the transfer hydrogenation of
unsaturated carbonyls with different substituent groups.
(
XPS) measurements were performed by a Kratos XSAM800
spectrometer using an Al Kα (hk = 1486.6 eV) radiation source.
The binding energies of elements were referred to C 1s at 284.8
eV.
Chin. J. Chem. 2019,37, XXX－XXX
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Concise Report
Li et al.
Acknowledgement
This work is supported by the National Natural Science
Foundation of China (Nos. 21473232, 21673271 and U1710112).
hydrogenation of cinnamaldehyde. J. Catal 2013, 303, 110-116.
Cattaneo,S.; Freakely, S.J.; Morgan, D.J.; Sankar, M.; Dimitratos, N.;
Hutchings, G. Cinnamaldehyde hydrogenation using Au-Pd catalysts
prepared by sol immobilisation. J. Catal. Sci. Technol. 2018, 8,
1
677-1685.
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(
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Concise Report
Li et al.
Entry for the Table of Contents
Page No.6
Title Carbide Supported Palladium-Iridium
Bimetallic Catalysts for Efficient Selective
Hydrogenation of Cinnamaldehyde
Penghui Li, Yingyong Wang, Yunwei Wang,
Guoqiang Jin, Xiang-Yun Guo and Xili Tong*
Chin. J. Chem. 2018,template
© 2018 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
This article is protected by copyright. All rights reserved.