Preparation of a highly efficient Pt/USY catalyst for hydrogenation and selective ring-opening reaction of tetralin
Preparation of a highly efficient Pt/USY catalyst for hydrogenation and selective ring-opening reaction of tetralin
Qi Wang 0
Zhang-Gui Hou 0
Bo Zhang 0
Jian Liu 0
Wei-Yu Song 0
De-Sheng Xue 0
Li-Zhi Liu 0
Dong Wang 0
Xin-Guo Chen 0
0 CNOOC Research Institute of Oil and Petrochemicals , Beijing 102249 , China
Ultrastable Y zeolite (USY)-supported Pt catalyst was prepared by gas-bubbling-assisted membrane reduction. The influence of reaction conditions and the metal and acid sites of catalysts on the catalytic performance of catalyst in hydrogenation and selective ring opening of tetralin, 1,2,3,4-tetrahydronaphthalene (THN), was studied. It was found that the optimal reaction conditions were at a temperature of 280 C, hydrogen pressure of 4 MPa, liquid hourly space velocity of 2 h-1 and H2/THN ratio of 750. Under these optimal conditions, a high conversion of almost 100% was achieved on the 0.3Pt/USY catalyst. XRD patterns and TEM images revealed that Pt particles were highly dispersed on the USY, favorable to the hydrogenation reaction of tetralin. Ammonia temperature-programmed desorption and Py-IR results indicated that the introduction of Pt can reduce the acid sites of USY, particularly the strong acid sites of USY. Thus, the hydrocracking reaction can be suppressed. Edited by Xiu-Qin Zhu
Hydrogenation and selective ring opening; Reaction conditions; Supported Pt catalyst; Tetralin
Diesel fuel is an important part of the worldwide energy
mix. Nowadays, vast amounts of diesel fuel are produced
from fluid catalytic cracking (FCC) technology
et al. 2013a)
. However, FCC diesel exhibits low cetane
number (CN) and high aromatic content (Arribas and
Mart´ınez 2002). The unqualified diesel can cause
incomplete combustion and the formation of undesirable
(Calemma et al. 2013)
. For the aim of environment
protection, production of clean diesel fuel is needed.
Hydrogenation and selective ring-opening (SRO)
technology is a promising way to improve the CN of diesel fuel
while minimizing the loss of diesel fraction (D’Ippolito
State Key Laboratory of Heavy Oil Processing and Beijing
Key Laboratory of Oil and Gas Pollution Control, China
University of Petroleum, Beijing 102249, China
et al. 2017). Through the hydrogenation reaction, the
aromatics are saturated. Then the rings of saturated aromatics
are further selectively opened to form products with high
CN. Meanwhile, carbon losses are very little
et al. 2002)
. And the development of catalysts with high
selectivity for ring opening has received increasing
(Piccolo et al. 2012)
Ring opening of aromatics can be completed on either
acid or noble metal catalysts, while a combination of the
two functions is much more valid than just one
(Rabl et al.
2011; Calemma et al. 2013)
. The existence of noble metals
can increase the reactivity of aromatics hydrogenation.
Hydrogenolysis of aromatics on metal catalysts is a
favorable way for accomplishing SRO reaction
et al. 2017)
. Recent research proved that hydrogenation of
aromatics should be accomplished ahead of ring opening
(Do et al. 2006; Mouli et al. 2007; Ziaei-Azad and Sayari
. Pt catalysts have been widely studied in many
(Mouli et al. 2012; Wang et al. 2017a; Luo et al.
. The existence of Pt active sites can facilitate the
adsorption of hydrogen and the efficient activation of
(Haas et al. 2012)
. Compared with
other catalysts, zeolite-supported Pt catalysts have
displayed higher activity for the hydrogenation reaction
(Schmitz et al. 1996; Song et al. 2004)
. In addition,
zeolitesupported Pt catalysts can promote the complete
hydrogenation of naphthalene at low temperature (Song and
The performance of a zeolite in SRO reaction is related
to its acidic property
(Alzaid and Smith 2013; Vicerich
et al. 2015)
. USY (ultrastable Y molecular sieve) shows
excellent catalytic performance in SRO reactions
(Galadima and Muraza 2016) due to its appropriate acidic
(Corma et al. 2001; Ding et al. 2006; Wang
et al. 2013b)
. USY possesses a high surface area, suitably
acidic sites and unique pore structure. USY has received a
great attention due to its special physicochemical
(Park et al. 2011; Zhou et al. 2013)
. Here we report the
synthesis of USY-supported Pt catalyst for the
hydrogenation and SRO reaction of tetralin. The effect of
reaction conditions, acidity and metal active sites of Pt/USY on
the ring-opening reaction of THN was studied, and the
synergy effect between hydrogenation active sites and acid
sites in Pt/USY was investigated.
2.1 Catalyst preparation
USY was synthesized by ammonium exchange from NaY.
Then, the sample was hydrothermally treated at 550 C for
2 h. USY-supported Pt catalysts were prepared by the
gasbubbling-assisted membrane reduction method which was
developed in our group
(Wei et al. 2011)
. In a typical
synthesis process, 2 mL poly-(N-vinyl-2-pyrrolidone)
(PVP) solution (PVP-to-deionized water ratio: 1/10) as a
stabilizer was added into 50 mL H2PtCl6 solution
(0.3 mmol/L). Then 1 g of USY zeolite support was
dissolved into the solution. The obtained solution was stored
in a precursor tank and driven by a peristaltic pump to keep
circulation flow. After that, NaBH4 was added into the
mixed solution. Then the solid was separated by a
centrifuge. At last, the obtained solid was washed with
deionized water three times, dried at 80 C for a night and
calcined in air at 350 C for 180 min. The amount of Pt
loading was 0.3 wt%, so the final catalyst is denoted as
2.2 Catalyst characterization
Powder X-ray diffraction (XRD) profiles were determined
using a Bruker D8 Advance X-ray diffractometer with Cu
Ka1 (k = 0.15406 nm) radiation, in a 2h range of 5 –50 .
N2 adsorption–desorption isotherms and pore size
distribution of the catalysts were obtained using a Micromeritics
TriStar II 3020 apparatus. The samples were pre-degassed
at 300 C for 5 h before N2 adsorption–desorption.
Transmission electron microscopy (TEM) images were
obtained with a JEOL JEM 2100 TEM. NH3-TPD signals
were collected on a DAS-7000. Prior to each test, the
samples of 0.1 g were pre-treated at 350 C in a NH3 flow
(35 mL/min) for 90 min, and then the sample was cooled
down to 100 C. Subsequently, ammonia was adsorbed at
this temperature for 30 min to ensure the sufficient
adsorption of NH3. Before desorption, the sample was
purged by a flowing N2 stream at 100 C for 1 h to remove
excessive and physically adsorbed NH3. Finally, the
catalysts were heated by a flow (35 mL/min) of pure N2 from
100 to 650 C at a heating rate of 10 C/min. The infrared
spectroscopy of chemisorbed pyridine experiments was
conducted on a Bruker EQUINOX 55 Fourier transform
infrared spectroscopy (Py-IR) spectrometer. A 20-mg
sample was fixed in an infrared cell. The catalysts were
pre-degassed at 400 C for 5 h before the adsorption of
pyridine. Py-IR spectra were recorded in the temperature
range between 200 and 350 C.
2.3 Catalytic activity test
Hydrogenation and selective ring opening of tetralin were
carried out in a fixed bed reactor (internal diameter 20 mm;
length 450 mm). All the catalysts were sieved to 40–60
mesh. For hydrogenation and selective ring opening of
tetralin reaction, 1 g catalyst was placed in the constant
temperature zone of the reactor and hydrogen was led to
the system at the rate of 15 mL/min. The catalyst was
reduced with hydrogen (15 mL/min) for 4 h at 300 C.
And then the model feed of THN was introduced by a
micro-pump. The reaction conditions of the hydrogenation
reaction were as follows: the temperature range of
200–350 C, under H2 atmosphere (pressure range of
2–6 MPa), a LHSV range of 1–4 h-1 and a H2/THN
volume ratio of 500–850. The steady reaction state was
maintained for 4 h. Then, the products were collected and
analyzed. Reaction products were detected on a gas
chromatograph (GC) with FID detector and analyzed by gas
chromatography–mass spectrometry (GC–MS). All the
reaction products detected on the GC were grouped
according to the number of carbon atoms of the products.
The products were grouped as follows: (a) C10-:
molecules containing less than 10 carbons. (b) C10 fractions:
selective ring-opening products (ROP) with 10 carbons,
C10 compounds with one or two C5 rings, both isomers of
decalin (decahydronaphthalene): trans-decalin
(transDHN) and cis-decalin (cis-DHN), and naphthalene.
(c) C10?: molecules containing more than 10 carbons.
3 Results and discussion
3.1 Structural and textural analyses
N2 adsorption–desorption isotherms and pore size
distributions of USY and 0.3Pt/USY were obtained. The
physical properties of all the samples are shown in Table 1.
BET surface areas (SBET) and pore volumes (Vp) of all the
samples were determined according to BET and BJH
methods, respectively. The pore diameters (dBJH) were
obtained by the BJH method. The pore size distribution
was centered at 6.3 nm for USY and at 6.2 nm for 0.3Pt/
USY, and this can be ascribed to the inter-granular porosity
of the samples. The pore diameter, surface area and pore
volume of 0.3Pt/USY were not significantly reduced,
indicating that most of Pt nanoparticles were dispersed on
The XRD patterns of USY and 0.3Pt/USY samples are
exhibited in Fig. 1. The diffraction peaks of USY and
0.3Pt/USY samples all showed the characteristics of USY
(Wang et al. 2017b)
, indicating that the loading of
Pt particles did not damage the initial framework of USY.
TEM examination showed the dispersion of Pt particles
on the surface of USY. Figure 2 presents TEM images of
0.3Pt/USY samples. Pt particles can offer active sites for
the hydrogenation reaction of THN. To obtain the particle
size distribution of Pt particles of 0.3Pt/USY, a statistical
analysis was performed to study the size distribution of 300
Pt particles on the surface of 0.3Pt/USY sample, and the
results are shown in Fig. 3. It is shown that the mean
diameter of Pt particles was 3.9 nm.
3.2 NH3-TPD results
To further study the effect of acidity on the catalytic
hydrogenation of THN, NH3-TPD experiments were
carried out. Figure 4 shows NH3-TPD patterns of USY and
0.3Pt/USY. It can be found that there existed three types of
acid sites. The desorption peak centered at 100–250 C
corresponded to the weak acid sites of the samples. The
desorption peak of the medium acid sites of the samples
centered in the range between 250 and 350 C, and the
desorption peak at 350–550 C corresponded to the strong
acid sites of the catalysts
(Ma et al. 2007)
. It can be seen
that the total acid content of 0.3Pt/USY catalyst decreased
remarkably compared to that of USY. The peak intensities
of the weak acid and medium acid sites of 0.3Pt/USY
slightly decreased, while the peak intensity of strong acid
sites of 0.3Pt/USY decreased greatly. It can be concluded
that part of acid sites of USY was covered by the dispersed
3.3 Py-IR results
Acid type distribution of the catalysts is tested by Py-IR.
The amounts of Bro¨nsted (B) and Lewis (L) acid sites of
samples are shown in Table 2. The results show that all the
catalysts contain both B and L acid sites. It is generally
believed that the desorption peak of pyridine at 200 C is
due to weak acid sites of samples. The desorption peak at
350 C can be ascribed to strong acid sites
(Wang et al.
. It can be seen that B and L acidity of 0.3Pt/USY
catalyst is significantly decreased. From the results of
Table 2, the number of weak B and L acid sites of 0.3Pt/
USY is slightly less than that of USY. Meanwhile, the
strong B and L acid sites of 0.3Pt/USY decrease
remarkably from USY. It is in keeping with the results of
3.4 Catalytic performance
3.4.1 Influence of the space velocity
The effect of LHSV on catalytic performance was studied
at T = 260 C, H2/THN = 500 and hydrogen pressure of
4 MPa. Table 3 lists the hydrogenation and selective
ringopening reaction results of THN at different LHSVs.
C10and C10? fraction yields were 6.7% and 12.0%,
respectively, when LHSV was 1 h-1. The ring-opening product
content is the highest for selective ring-opening reactions
Particle size (d), nm
Fig. 3 Pt particles size distribution of 0.3Pt/USY
of THN at different LHSVs (1, 2 and 3 h-1). It indicated
that a low space velocity could facilitate the conversion of
THN, while it promoted the cracking and condensation
reactions. When LHSV increased from 1 to 2 h-1, the ROP
(ring-opening products) yield significantly increased from
16.5% to 21.9%, whereas the conversion of tetralin
decreased from 91.6% to 89.7%. When LHSV increased to
3 h-1, the conversion of tetralin was only 65.3%. It is
shown that the conversion of tetralin decreased with the
increase in reaction space velocity. It was due to the short
Fig. 4 NH3-TPD profiles of (a) USY and (b) 0.3Pt/USY samples
contact time between tetralin and 0.3Pt/USY. A limited
reaction of THN occurred. At LHSV = 2 h-1, the results of
the conversion of THN and the selectivity of ROP were
suited. Considering the obtained results, the optimal LHSV
for hydrogenation and ring-opening reaction of tetralin is
SROP denotes the selectivity of all the ring-opening products in the
3.4.2 Influence of H2/THN ratio
The effect of H2/THN ratio was studied at T = 260 C,
LHSV = 2 h-1 and hydrogen pressure of 4 MPa. As
displayed in Fig. 5, the tetralin conversion and the yield of
DHN increased remarkably with an increase in the H2/THN
ratio from 500 to 750. The reaction rate of THN cracking
depended on the adsorption rate of the reactant molecules
on the surface of the catalyst
(Santikunaporn et al. 2004)
The H2/THN ratio is one of the important factors for the
adsorption rate of THN on the surface of 0.3Pt/USY. The
partial pressure of H2 increased regularly with the increase
in the H2/THN ratio. It was beneficial to the adsorption and
activation of H2 on the surface of Pt/USY, and the reaction
rate of THN hydrogenation conversion was also elevated.
When H2/THN ration was 500, the yield of C10? was
8.2%. It was the highest C10? content for the different H2/
THN ratios. The hydrogenation reaction is an exothermic
reaction. When the H2/THN ratio is low, the different
temperatures in the reactor will be very important. The
higher temperature and a lower partial pressure of H2 can
cause an increase in the dehydrogenation of THN. The
higher H2/THN ratio can prevent the formation of the
coking precursor. However, the energy consumption of the
device will increase with the increase in H2/THN ratio.
Taking into account all the factors, the optimal H2/THN
ratio was determined to be 750.
3.4.3 Influence of the hydrogen pressure
The effect of the hydrogen pressure on tetralin conversion
and yield of the main products was investigated at
T = 260 C, H2/THN = 750 and LHSV = 2 h-1. As shown
in Fig. 6, the tetralin conversion, ROP selectivity and
content of trans-DHN increased with an increase in the
hydrogen pressure from 2 to 4 MPa. It is noted that the
conversion of tetralin remained unchanged when the
hydrogen pressure rose from 4 to 6 MPa, whereas the
selectivity of ROP decreased from 30.1% to 25.4%. It was
indicated that the low hydrogen pressure was unfavorable
to the hydrogenation of THN. When the hydrogen pressure
was 2 MPa, the tetralin conversion was only 89%.
Meanwhile, an increase in H2 pressure would result in an
increase in trans-DHN. When the hydrogen pressure was
4 MPa, ROP selectivity was 30.1%. An increase in H2
pressure resulted in a decrease in the content of C10?. It
indicated that the high H2 pressure was beneficial to
suppressing the coking reaction. However, the high hydrogen
pressure might lead to an increase in cost and safety risks.
Taking into account the obtained results, the optimal
hydrogen pressure for hydrogenation and selective
ringopening reaction of THN was determined to be 4 MPa.
3.4.4 Influence of the reaction temperature
The effect of the reaction temperature is studied at
LHSV = 2 h-1, H2/THN = 750 and hydrogen pressure of
4 MPa. The results are shown in Fig. 7. At the low
temperature of 220 C, the conversion of THN was almost
100% and the selectivity of ring-opening product was only
8.95%. It indicated that 0.3Pt/USY possessed a high
activity for the conversion of THN and an inferior
selectivity of ROP at 220 C. With a temperature increase, the
tetralin conversion could almost reach 100% in the range of
220–300 C. The selectivity to ROP regularly increased
with increasing temperature. It was concluded that the high
temperature could promote the THN ring-opening reaction.
After the temperature rose from 280 to 300 C, the
Fig. 7 Dependence of THN conversion on reaction temperature in the
presence of 0.3Pt/USY catalyst, and of ROP selectivity and yield of
main products on temperature at H2/THN = 750, LHSV = 2 h-1 and
hydrogen pressure of 4 MPa
conversion of THN was not significantly changed.
Meanwhile, the content of C10 decreased from 94.4% to 89.1%,
which was due to the growth of the hydrocracking reaction
of C10 and finally converting to C10-. These results
indicated that the high temperature was useful for the
hydrocracking reaction of C10. It was reported that the
hydrocracking reaction was a sequential reaction of the
(Ma et al. 2007)
. To obtain high yields of
ROP and C10 fractions, the hydrocracking reaction should
be avoided. Taking into account all the factors, the optimal
temperature was determined to be 280 C.
3.4.5 Role of the metal sites and acid sites
The hydrogenation reactions of tetralin can take place on
noble metal sites
(Du et al. 2005)
. To determine the role of
Pt in this reaction, the hydrogenation reactions of tetralin
were tested over USY and 0.3Pt/USY at the optimum
reaction conditions. The results of tetralin conversion, ROP
selectivity and main products in the presence of USY and
0.3Pt/USY samples are listed in Table 4. For USY sample,
the conversion of tetralin was only 29.4% and the yields of
trans-DHN and cis-DHN were only 2.4% and 0.4%.
However, after the addition of Pt, the conversion of THN
could reach to 99.6% and the yields of trans-DHN and
cisDHN were enhanced to 40.1% and 3.7%. It indicated that
the hydrogenation of THN could take place on USY, but
the rate was very low. However, the hydrogenation activity
of USY was enhanced sharply with the incorporation of Pt.
The low content of Pt and the dispersed Pt particles offer an
abundance of the metallic centers for the hydrogenation
reactions of THN. Based on the mechanism of bifunctional
(Christoffel and Paa´l 1982)
, the acidic function
acted as an important part in the SRO reaction. The acidic
site is an important factor for the SRO reactions. 0.3Pt/
USY can give the appropriate acidic property. The weak
acid sites can decrease the hydrocracking reactions. The
strong acid sites of USY can lead to the hydrocracking of
reactants. For the purpose of minimizing the loss of diesel
oil, the hydrocracking reactions should be avoided. From
Table 4, the yield of C10- was 6.4% on USY. On 0.3Pt/
USY, the introduction of 0.3% Pt reduced the total number
of the acid sites, especially the strong acid sites according
to the results of NH3-TPD and Py-IR. The yield of the
hydrocracking products reduced to 1.4% with the decrease
in the acid sites.
In this work, 0.3Pt/USY with low Pt content and highly
dispersed Pt particles were prepared by the
gas-bubblingassisted membrane reduction method. 0.3Pt/USY displayed
excellent performance for the hydrogenation and selective
ring opening of THN. The addition of Pt reduced the total
number of the acid sites, especially the strong acid sites of
USY. The optimal reaction conditions were a hydrogen
pressure of 4 MPa, temperature of 280 C, LHSV of 2 h-1
and H2/THN ratio of 750. The conversion of THN was
almost 100%, and the selectivity of ring-opening product
was 38.5%. The high conversion of THN and the good
selectivity of ROP were due to sufficient metal sites and
appropriate acid sites.
Acknowledgements The authors thank the National Natural Science
Foundation of China (U1662103 and 21673290); the National
HiTech Research and Development Program (863) of China
(2015AA034603); and the China National Offshore Oil Corporation
Fund (LHYJYKJSA20160002) for their funding.
Open Access This article is distributed under the terms of the Creative
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