Supported Pt-Ni bimetallic nanoparticles catalyzed hydrodeoxygenation of dibenzofuran with high selectivity to bicyclohexane

Article abstract of DOI:10.1016/j.cclet.2021.05.059

Catalytic hydrodeoxygenation (HDO) is one of the most effective methods to upgrade the oxygen-containing compounds derived from coal tar to valuable hydrocarbons. Herein, an efficient bimetallic catalyst Pt₁Ni₄/MgO was prepared and applied in the HDO of dibenzofuran (DBF). High yield (95%) of the desired product bicyclohexane (BCH) was achieved at 240 °C and 1.2 MPa of H₂. Superior catalytic performance could be ascribed to the “relay catalysis” of Pt sites and Ni sites, and the reaction pathway is proposed as well. Scale-up experiment and recyclability test were also performed, which demonstrated the recyclability and promising potential application of Pt₁Ni₄/MgO.

Full text of DOI:10.1016/j.cclet.2021.05.059

Journal Pre-proof
Supported Pt-Ni bimetallic nanoparticles catalyzed
hydrodeoxygenation of dibenzofuran with high selectivity to
bicyclohexane
Pengyu Wu , Chun Cai
PII:
DOI:
Reference:
S1001-8417(21)00372-7
https://doi.org/10.1016/j.cclet.2021.05.059
CCLET 6402
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Chinese Chemical Letters
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Accepted date:
25 March 2021
25 May 2021
26 May 2021
Please cite this article as: Pengyu Wu , Chun Cai , Supported Pt-Ni bimetallic nanoparticles catalyzed
hydrodeoxygenation of dibenzofuran with high selectivity to bicyclohexane, Chinese Chemical Letters
(2021), doi: https://doi.org/10.1016/j.cclet.2021.05.059
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Chinese Chemical Letters
journal homepage: www.elsevier.com
Communication
Supported Pt-Ni bimetallic nanoparticles catalyzed hydrodeoxygenation of
dibenzofuran with high selectivity to bicyclohexane
Pengyu Wu, Chun Cai 
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, China
ARTICLE INFO
ABSTRACT
Catalytic hydrodeoxygenation (HDO) is one of the most effective methods to upgrade the
oxygen-containing compounds derived from coal tar to valuable hydrocarbons. Herein, an
efficient bimetallic catalyst Pt1Ni4/MgO was prepared and applied in the HDO of dibenzofuran
(DBF). High yield (95%) of the desired product bicyclohexane (BCH) was achieved at 240 °C
and 1.2 MPa of H2. Superior catalytic performance could be ascribed to the “relay catalysis” of
Pt sites and Ni sites, and the reaction pathway is proposed as well. Scale-up experiment and
recyclability test were also performed, which demonstrated the recyclability and promising
potential application of Pt1Ni4/MgO.
Article history:
Received
Received in revised form
Accepted
Available online
Keywords:
Hydrodeoxygenation;
Dibenzofuran;
Bicyclohexane;
Bimetallic catalyst;
Relay catalysis;
The continuous depletion of fossil fuels and demands for the
cleaner earth has led to an imperative requirement in efficient
utilization of traditional fossil resources like coal and raw oil.
Coal tar is a common by-product of the coal processing industry,
without suitable processing, it may cause wastes of energy
resources and serious environmental pollution [1]. The high
oxygen content in the composition of coal tar usually lead to high
viscosity and low heating value [2], which prevent the wide
utilization of it. Therefore, catalytic hydrodeoxygenation (HDO)
was recognized as a promising method for upgrading of the O-
containing compounds and tuning the waste to high heating value
hydrocarbons [3-6]. For example, dibenzofuran (DBF) which is a
representative O-containing compound of coal tar and an
important intermediate in biomass gasification [7], could be
upgrading to value-added hydrocarbon fuel like bicyclohexane
(BCH) by HDO reaction.
The HDO reaction usually include hydrogenation,
hydrogenolysis and deoxygenation, accordingly, the catalyst
must be able to activate H2 while activating C-O bonds also.
Cobalt molybdenum sulfide (Co-MoS2) and nickel molybdenum
sulfide (Ni-MoS2) supported catalysts have been frequently used
for deoxygenation of DBF due to the direct scission of the C-O
bond over the MoS2 active phase and the sulfuric vacancy sites [8,
9]. Nevertheless, using these metal sulfide catalysts needs
cofeeding of extra sulfide such as CS2 or H2S to maintain the
activity of the catalyst [10, 11], and this may introduce sulfur into
the products and results in contamination. Besides sulfide
catalysts, Mo2C was recently reported as catalyst for the HDO of
DBF at 350 °C, and 4.1 MPa H2 pressure [12], HDO products
including both cyclohexylbenzene (CHB) and bicyclohexane
(BCH) were generated with about 50% yield. Owing to the good
capability to activate H2, noble metals like Ru, Pd, Rh and Pt
were reported to be efficient for the HDO of oxygen containing
aromatics under milder conditions [13-15]. Liang et al. [16, 17]
reported the HDO of DBF at 280-300 °C and 3 MPa H2 over
supported noble metal catalysts and acquired high efficiency.
Although these seminal works reported, a high selectivity to the
complete HDO product BCH seldom is focused on. Therefore, it
is still in demand that an efficient catalyst which shows high
selectivity to BCH in the HDO reaction of DBF.
Bimetallic nanoparticle (BMNP) catalysts, which combine two
different metals, usually show performance superior to the
monometallic counterparts due to the “synergistic effects” [18,
19]. Incorporation of Mo into Pt or Pd has been reported by
Infantes-Molina and co-workers [20], the bimetallic catalyst was
applied in the HDO of DBF and the performance was improved,
however, the selectivity to BCH was still afforded lowly. Due to
the high dissociation energy, the cleavage of C-O bonds is one of
the most challenging steps in HDO reactions [21], and a series of
reports have mentioned that Ni-based catalysts show good
performance in the cleavage of C-O bonds [22-24]. The previous
works of our group have demonstrated that the combination of Ni
and noble metals could significantly enhance the activity in
catalytic cleavage of C-O bonds [25, 26]. On the basic of the
 Corresponding author.
E-mail address: c.cai@njust.edu.cn

Table 1
above reports, BMNPs combining Ni and noble metal, which
may inherit the advantages of both metals while upgrading the
catalytic performance, were expected to be promising catalysts in
the HDO reactions. Herein, a series of BMNPs based on Ni and
noble metals were prepared and tested for the HDO of DBF, and
MgO was chosen as the catalyst support for the BMNPs to make
the catalyst heterogeneous and recyclable. Pleasantly,
Pt1Ni4/MgO shows good activity and the yield of desired product
BCH which was up to 95% at 240 °C in 3 h. Alloying of those
two metals inherits both great hydrogenation performance from
Pt sites and good activity to C-O bonds cleavage from Ni sites. In
addition, scale-up experiment proved that the catalyst has
prospect for industrial application, and no significant loss in
catalytic performance was observed when Pt1Ni4/MgO was
recycled six times.
As a representative example, the HDO of DBF was carried out
to evaluate the performance of the catalysts. Decalin was chosen
to be the solvent in the reactions considering it has an inert
chemical structure, a high boiling point and a low vapor pressure
which limit the total pressure of reactor in safe range after
heating. The products were identified by GC-MS analysis, and
there were seven main products detected in this work. As shown
in Scheme 1, compounds 1-3 retained the O-containing ring, and
these products were generated from the hydrogenation of DBF
without any catalytic cleavage of the C-O bond. Hydrogenolysis
of the C-O bond occurred and give the compounds 4-5, which
kept one of the C-O bonds in molecule. Compounds 6-7 were
observed from the HDO reaction, and BCH 7 was the target
product in our study.
HDO of DBF over different catalysts.a
Sel%
1-3
83
77
7
Entry Catalyst
Conb %
4+5
5
12
20
9
3
10
8
4
5
3
15
10
4
6
12
4
32
4
1
4
4
3
11
34
22
4
7
< 1
7
1
Pd/MgO
Pt/MgO
Ni/MgO
Pd1Ni4/MgO
Pt1Ni4/MgO
78
84
23
90
100
2
3c
4
41
67
95
21
86
91
83
53
55
69
93
20
1
5
6d
7
Pt/MgO + Ni/MgO 86
65
2
2
1
10
8
Pt1Ni1/MgO
Pt1Ni2/MgO
Pt1Ni6/MgO
Pt1Ni4/SiO2
Pt1Ni4/AC
92
98
96
60
47
51
98
8
9
10
11
12
13f
Pt1Ni4/Al2O3
Pt1Ni4/MgO
17
1
2
a Reaction conditions: 1 mmol DBF, 15 mg catalyst (0.3 mol% Pd or
Pt), 3 mL decalin, 1.2 MPa H2, 240 °C, 3 h.
b Conversion of DBF.
c 15 mg Ni/MgO (1.2 mol% Ni).
d 15 mg Pt/MgO and 15 mg Ni/MgO.
f 5 g DBF, 450 mg Pt1Ni4/MgO, 80 mL decalin.
Physical mixtures of Pt/MgO and Ni/MgO do not lead to an
apparent promotion in catalytic selectivity (Table1, entry 6),
demonstrating that it is the cooperativity inside Pt1Ni4 BMNPs,
not the simple mixture of Pt and Ni, accounts for the elevation of
the catalytic performance. Compositions of the BMNPs were
reported to be vital for the catalytic efficiency of bimetallic
catalysts, and catalysts with different Ni/Pt molar ratios were
prepared and tested in the reaction (Table 1, entries 7-9). Keeping
the Pt loading in the reaction constant (0.3 mol% Pt), catalysts
with higher Ni contents show better selectivity to BCH. However,
when the Ni/Pt molar ratio was higher than 4, selectivity to 6
increased, and a Ni/Pt ratio of 4 could be emerged as the
optimized ratio. Next, Pt1Ni4 BMNPs were immobilized on
different supports including SiO2, activated carbon (AC) and
Al2O3, and the obtained catalysts were applied in the reaction
(Table 1, entries 10-12). Lower conversions were afforded by
these reference catalysts, and the superior activity of Pt1Ni4/MgO
could be owing to the better dispersity of MgO in decalin. Scale-
up experiment was also performed (Table 1, entry 13),
Pt1Ni4/MgO showed good performance with 5 g of DBF loaded,
which signified the promising application of the catalyst in
industry.
Scheme 1 Main products in the HDO reaction of DBF.
At the initial stage, monometallic nanoparticles (NPs) were
supported on MgO and tested in the HDO of DBF. Monometallic
noble metal catalysts showed good activity in conversion of DBF
(Table 1, entries 1 and 2), which could be attributed to their
excellent hydrogen activity, however the main products in these
reactions were hydrogenation products (compounds 1-3), almost
no target product BCH was detected in the solution catalyzed by
Pd/MgO, and only 7% selectivity to BCH was achieved by
Pt/MgO. The Ni monometallic catalyst afforded higher
selectivity towards deoxidation products 6 and 7 (Table 1, entry
3), although the reaction had a low conversion of 23%. Since no
ideal result achieved by monometallic catalysts, bimetallic
catalysts alloying Ni and noble metals were prepared and used in
the HDO reaction. As expected, noteworthy enhancement in
catalytic performance was observed when the bimetallic catalysts
were employed (Table 1, entries 4 and 5), both conversion and
selectivity increased significantly. Between these two,
Pt1Ni4/MgO showed a better performance, which could convert
DBF completely and the selectivity towards BCH was up to 95%.
Effects of reaction temperature and initial H2 pressure were
investigated and the results are presented in Fig. 1. Variations in
reaction temperature had
a significant influence on the
conversion and selectivity for the HDO of DBF (Fig. 1a and
Table S1 in Supporting information). With the reaction
temperature increased, both the conversion of DBF and
selectivity to BCH enhanced. When the temperature went up to
240 °C, all DBF was converted and the selectivity to BCH
reached 95 %, and no improvement in the reaction selectivity was
observed with further increasement in temperature. Initial H2
pressure had a lower effect on the selectivity to BCH, the raising
pressure increase the conversion of DBF and afforded 100%
conversion under 1.2 MPa (Fig. 1b).
With the optimized reaction conditions established, a model
reaction was conducted and tracked by GC and GC-MS to gain
preliminary insights into the reaction pathway. As displayed in
Fig. 2, the yields of hydrogenation products 2 and 3 increased at
first and then decreased with the increase in the reaction time.
Subsequently, yield of 5 increased and peaked while yield of 7

continuing growth and reaching up to 95% after 3 h. According
to the above results, a plausible reaction pathway for the HDO of
DBF under the current conditions is proposed in Scheme 2. DBF
was hydrogenated to 1 and 2 at the initial step, then both further
hydrogenation and ring-opening of 2 occurred. Considering the
deoxygenation barrier is higher than that of hydrogenation for 4
[21] and the content of 6 in the products kept at a low level
during the whole process (Fig. 2), it can be derived that most 4
was hydrogenated to 5 and 7 was mostly formed by the cleavage
of C-O bond in 5. Moreover, because of the higher bond
dissociation energy, Csp2-O bonds are more difficult to be
cleaved than Csp3-O bonds [27, 28], therefore, hydrogenation of
the intermediates could effectively promote the deoxygenation
step. Based on the tandem pathway, it can be inferred that the
Pt1Ni4/MgO should be a multifunctional catalyst which could
continuously catalyze the hydrogenation and the deoxygenation.
Because the Pt monometallic catalyst showed a preference for the
hydrogenation reaction and the Ni monometallic catalyst showed
a high selectivity to deoxygenated products (Table 1, entries 2-3),
there might be a “relay catalysis” between Pt sites and Ni sites
over the Pt1Ni4/MgO: at first, DBF was hydrogenated over the Pt
sites, then, the hydrogenated intermediates were “relayed to” the
Ni sites and deoxygenated.
Fig. 1. Effect of the reaction conditions: 1 mmol DBF, 15 mg Pt1Ni4/MgO (0.3 mol% Pt), 3 mL decalin, 3 h, (a) effect of the reaction
temperature under 1.2 MPa H2, (b) effect of the initial H2 pressure at 240 °C.
Scheme 2 Proposed reaction pathway for the HDO of DBF over Pt1Ni4/MgO catalyst.
the as-prepared Pt1Ni4 BMNPs have a homogeneous distribution
throughout the surface of MgO. The Pt1Ni4 BMNPs are well
proportioned spherical with an average diameter of 4 nm,
compared with the Pt1Ni1 BMNPs (Fig. S1 in Supporting
information), the smaller size could mean more contact
opportunities between the active sites and substrates. More
information about the structure of the BMNPs is displayed by the
high resolution TEM (HRTEM) image (Fig. 3b), and a well-
resolved lattice spacing of 0.216 nm was revealed, which
corresponds to the (111) plane of the Pt-Ni alloy [29]. The
crystallite phases of the BMNPs were also revealed by the
selected area electron diffraction (SAED) image (Fig. 3c), the
Fig. 2. Time-course monitoring of the reaction. Reaction conditions:
1 mmol DBF, 15 mg Pt1Ni4/MgO (0.3 mol% Pt), 3 mL decalin, 1.2
diffraction pattern verified the formation of Pt-Ni alloy (JCPDS
No. 65-2797). The EDS elemental maps (Figs. 3d-f) profile
obviously manifested the distribution of Pt and Ni in Pt1Ni4/MgO,
the distributions of Pt and Ni match well with the distribution of
NPs, which further confirmed the alloy form of Pt1Ni4 BMNPs.
In the XRD patterns (Fig. S3 in Supporting information) no
obvious peaks for the Pt1Ni4 BMNPs, which might be attributed
to the low content and small size of the Pt1Ni4 BMNPs in catalyst.
MPa H2, 240 °C.
To explore the applicability of the catalytic system, substrates
including diphenyl ether, phenol and benzofuran were tested.
Gratifyingly, high yield of HDO products were achieved under
the optimized reaction conditions (Table S4 in Supporting
information), which verified the applicability of Pt1Ni4/MgO in
various HDO reactions.
The morphologies of Pt1Ni4/MgO were directly observed by
transmission electron microscopy (TEM). As presented in Fig. 3a,

Supporting information). In the spectra of Pt 4f region (Fig S4b
in Supporting information), the peaks sit at 70.8 eV and 74.2 eV
which can be assigned to metallic Pt0, in contrast to that of
Pt/MgO (Fig. S4d in Supporting information), a negative shift by
about 0.25 eV can be observed. The shift came from the different
electronegativities of Pt (2.28) and Ni (1.91) [30], and suggesting
the electron-transfer effect from Ni to Pt inside the Pt1Ni4
BMNPs. The spectra of Ni 2p region (Fig. S4c in Supporting
information) shows the presence of metallic Ni as well as Ni
oxide, which could be the result of the fact that nickel can be
easily oxidized to oxide and hydroxide when exposed to oxygen
and moisture in air [25]. Besides, the Ni/Pt atomic ratio on the
surface of Pt1Ni4/MgO determined by XPS was 4.8, which is
close to the result of ICP-MS (Table S2 in Supporting
information). It can be concluded from the characterizations
results that the Pt1Ni4 alloy BMNPs are formed and have a
homogeneous distribution on the surface of MgO. The formation
of the Pt1Ni4 alloy BMNPs minimized the distance between Pt
sites and Ni sites and increased opportunities for “relay catalysis”
between the two metals sites.
Fig. 3. (a) TEM image and size distribution of Pt1Ni4/MgO, (b)
HRTEM image of Pt1Ni4/MgO, (c) SAED image of Pt1Ni4 BMNPs,
(d) STEM image of Pt1Ni4/MgO, EDS elemental maps for (e) Pt and
(f) Ni.
X-ray photoelectron spectrum (XPS) was employed to
ascertain the detailed electronic structure and chemical states of
Pt1Ni4/MgO. Well-defined peaks corresponding to both Pt and Ni
species can be detected in the survey spectrum (Fig. S4a in
Fig. 4. (a) Recyclability of Pt1Ni4/MgO. (b) Hot filtration experiments of Pt1Ni4/MgO for the HDO of DBF.
Recyclability is a key issue for a heterogeneous catalyst, and the recyclability of Pt1Ni4/MgO was tested under the scale-up
experiment conditions (Table 1, entry 13). Upon the completion of the reaction, the catalyst was separated by filtration, washed by
ethyl acetate and then dried under vacuum for reuse in the next cycle. As shown in Fig. 4a, the catalyst could be reused up to six
times with only a minor loss in its activity, which may due to the mechanical loss of the catalyst during the recycle process. The
heterogeneous nature of Pt1Ni4/MgO was demonstrated by a hot filtration experiment under the optimized conditions (Table 1, entry
5). When the reaction proceeded for 1 h, the reactor was cooled down to room temperature and the catalyst was filtered off, the
isolated solution was added into the reactor which was then purged with H2 and heated for further reaction. As shown in Fig. 4b, no
further increase in conversion was observed after the removal of the catalyst, and addition of the removed catalyst led to the
resumption of the reaction. The TEM image of the recovered Pt1Ni4/MgO after 6 cycles (Fig. S2 in Supporting information) shows
no obvious change in the morphology and the Pt1Ni4 BMNPs did not agglomerate. The XRD (Fig. S3 in Supporting information)
and XPS spectra (Fig. S5 in Supporting information) of the recovered catalyst are not obviously different from the fresh samples.
Moreover, ICP-MS analysis of the catalyst after 6 cycles (Table S2) and the reaction solution (Table S3 in Supporting information)
revealed that the metal leaching of the catalyst is negligible during the reaction process. These results confirmed that Pt1Ni4/MgO is
highly stable for the HDO of DBF.
In summary, a novel Pt-Ni bimetallic catalyst Pt1Ni4/MgO has been successfully prepared, which showed excellent selectivity to
BCH in the HDO reaction of DBF. The reaction could play an important role in upgrading and utilization of the by-products from
coal processing industry. With Pt1Ni4/MgO catalyzed, all DBF could be converted and the selectivity to BCH was up to 95% at 240
°C and 1.2 MPa of H2. The efficient catalytic performance may originate from the “relay catalysis” effect of Pt sites and Ni sites: Pt
sites activate H2 and hydrogenate DBF to hydrogenated intermediates, Ni sites were believed to accelerate the cleave process of C-
O bonds and finally result in desired product BCH. Characterizations of Pt1Ni4/MgO indicated the alloy form and ultrasmall size of
Pt1Ni4 BMNPs on the surface of MgO. Besides, outstanding performance in scale-up experiment and recyclability test highlights the
promising potential of this bimetallic catalyst in sustainable industry.
Conflicts of interest
There are no conflicts to declare.

Acknowledgments
We gratefully acknowledge Key Laboratory of Biomass Energy and Material, Jiangsu Province (No. JSBEM201912) and
Chinese Postdoctoral Science Foundation (Nos. 2015M571761 and 2016T90465) for financial support. This work was funded by
the Priority Academic Program Development of Jiangsu Higher Education Institution and Instrument and Equipment Foundation of
Nanjing University of Science & Technology.
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Graphical Abstract
Efficient bimetallic catalyst Pt1Ni4/MgO was prepared and applied in the hydrodeoxygenation of dibenzofuran. High yield of
bicyclohexane was afforded, which could be ascribed to the “relay catalysis” effect inside the catalyst.