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Hydrodenitrogenation of quinoline and its intermediates over sulfided NiW-Al2O3 in the absence and presence of H2S.

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ASIA-PACIFIC JOURNAL OF CHEMICAL ENGINEERING
Asia-Pac. J. Chem. Eng. 2009; 4: 704–710
Published online 7 July 2009 in Wiley InterScience
(www.interscience.wiley.com) DOI:10.1002/apj.322
Research Article
Hydrodenitrogenation of quinoline and its intermediates
over sulfided NiW/γ -Al2O3 in the absence and presence
of H2S
YeZhi Luan, Qiumin Zhang,* Demin He, Jun Guan and Changhai Liang
State Key Laboratory of Fine Chemicals, Institute of Coal Chemical Engineering, Dalian University of Technology, Dalian, China
Received 30 October 2008; Revised 5 March 2009; Accepted 8 March 2009
ABSTRACT: Hydrodenitrogenation (HDN) reactions of quinoline and its intermediates were carried out at 300–420 ◦ C
and 2–6 MPa over sulfided NiW/γ -Al2 O3 in the absence and presence of H2 S. The results show that temperature
and pressure have a drastic effect on nitrogen removal and production distribution in the HDN of quinoline.
1,2,3,4-tetrahydroquinoline THQ1 mainly underwent dehydrogenation to quinoline and then hydrogenated to 5,6,7,8tetrahydroquinoline (THQ5), and decahydroquinoline (DHQ) following by ring opening elimination to give 2propylcyclohexylamine (PCHA) and hydrocarbons. The HDN of THQ5 mainly proceeded the path of DHQ–PCHA, the
reactions between THQ5, DHQ, THQ1 and quinoline are so fast that a quasi equilibrium between the four compounds
is established quickly at a very low space time. The addition of H2 S promotes the reaction of DHQ, but retards the
pathway of OPA. The promoting effect of H2 S is dominant at low concentration of H2 S. However, its inhibiting
effect prevails at high concentrations. The HDN via the pathway of DHQ is much easier than OPA over the sulfided
NiW/γ -Al2 O3 . The HDN of OPA was suppressed by the presence of Q, THQ1, THQ5, and DHQ, maybe due to their
stronger adsorption on the catalyst.  2009 Curtin University of Technology and John Wiley & Sons, Ltd.
KEYWORDS: hydrodenitrogenation; quinoline; intermediates; sulfided NiW/γ -Al2 O3
INTRODUCTION
Oil shale has been identified as an alternative source for
production of crude oil substitutes owing to its availability as large large reserves in the world. Oil shale
can convert into shale oils which contain up to 60% of
middle distillates, 0.6 ∼ 0.9% of sulfur, 0.8 ∼ 3% of
nitrogen, and 1 ∼ 5% of oxygen, by retortion or pyrolysis. Upgrading of shale oil to clean fuel by hydrotreating requires simultaneous desulfurization, denitrogenation, and deoxygenation. The hydrotrerating process is
a significantly different operation from that of crude
oil, and is limited primarily by removal of nitrogencontaining compounds. The nitrogen-containing compounds in shale oil exist mainly in the form of basic
nitrogen compounds. Quinoline is one of the representative basic nitrogen compounds found in shale oil.
Therefore, quinoline is used as model compound for
denitrogenation of shale oil in this work.
The hydrodenitrogenation HDN of quinoline has
widely been studied by a few research groups[1 – 6] . The
*Correspondence to: Qiumin Zhang, State Key Laboratory of Fine
Chemicals, Institute of Coal Chemical Engineering, Dalian University of Technology, Dalian 116012, China.
E-mail: qmzhang@chem.dlut.edu.cn
 2009 Curtin University of Technology and John Wiley & Sons, Ltd.
HDN pathway of quinoline is accepted as shown in
Scheme 1. Since the C–N bond in the aromatic heterocycle is much stronger than that in the aliphatic
heterocycle, the first step for the HDN of quinoline is
the hydrogenation of aromatic heterocycle. The hydrogenation products include 1,2,3,4-tetrahydroquinoline
THQ1, 5,6,7,8-tetrahydroquinoline (THQ5) and decahydroquinoline (DHQ); all the reactions between them are
potentially reversible. One pathway to removing nitrogen is via o-phthaldialdehyde (OPA) and the other is
via DHQ.
The HDN mechanism of OPA and DHQ as intermediates over sulfided NiMo/Al2 O3 catalysts has been
studied[7 – 9] . However, few reports were found on
HDN of THQ as intermediate, especially on THQ1.
Simultaneously, it is generally accepted that sulfided
NiW catalysts are superior to sulfided Co(Ni)Mo
catalysts for HDN, because of their high activity
in hydrogenation reaction[10,11] . Differences in catalysts, reaction conditions, and experimental procedures were said to determine reaction mechanism and
kinetics[5,10] . Therefore, it is necessary and very interesting to understand the HDN mechanism of quinoline and its intermediates over sulfided NiW/γ -Al2 O3
catalyst.
Asia-Pacific Journal of Chemical Engineering
HDN OF QUINOLINE AND ITS INTERMEDIATES
Scheme 1. Reaction network of the hydrodenitrogenation of quinoline.
To gain further insight into the HDN of quinoline,
we studied the HDN of quinoline at 340 ◦ C and at
3.0 MPa in the absence and presence of H2 S over
sulfided NiW/γ -Al2 O3 . We also used the reaction
intermediates of the HDN network, such as THQ1
and THQ5, as reactants. The effects of temperature,
pressure, and H2 S on the HDN of quinoline were also
investigated.
EXPERIMENT
The NiW/γ -Al2 O3 catalyst employed in this study was
prepared by incipient wetness impregnation of γ -Al2 O3
(specific surface area 260 m2 /g, pore volume 0.5 cm3 /g)
and contained 25 wt% WO3 and 3 wt% NiO. The
catalyst was crushed and sieved to an 80–100 mesh
particle size.
The catalytic reactions were carried out in a continuous fixed-bed reactor, filled with 0.1 g catalyst that
was diluted with 1.4 g SiC. The catalyst was sulfided
in situ with a mixture of 10% H2 S in H2 (120 ml/min)
at 400 ◦ C and 1.0 MPa for 20 h. After sulfidation, the
pressure was increased to 3.0 MPa, the temperature
was changed to reaction temperature, and the liquid
reactant was fed to the reactor by means of a highpressure pump. The activity of the sulfided NiW/γ Al2 O3 catalyst arrived in steady state after HDN reaction was run for about 24 h. Most of experiments
were performed with the liquid reactant composed of
1.2 mol% decane (as internal standard for GC analysis), 3.1 mol% quinoline or its intermediate as reactant,
0.5 ∼ 3.6 mol% CS2 as a H2 S precursor, and decalin
(as solvent for the nitrogen-containing compounds).
Some experiments were performed with quinoline and
its intermediate as reactant. The reaction product was
analyzed with a 7890-gas chromatography with OV-101
capillary column and a flame ionization detector. Identification of product was performed with an Agilent 6890
gas chromatograph equipped with an HP-5MS capillary
column and an Agilent 5973 mass selective detector.
The selectivity was defined as selectivity = n /n, where
n denotes the molar of each product and n, the total
molar of products.
 2009 Curtin University of Technology and John Wiley & Sons, Ltd.
RESULTS
HDN of quinoline
The HDN of quinoline was carried out at 340 ◦ C and
3.0 MPa in the presence of 1.0 mol% H2 S over sulfided
NiW/γ -Al2 O3 . Typical reaction profiles and production
selectivities are presented in Fig. 1. THQ1, THQ5,
DHQ, OPA, propylbenzene (PB), propylcyclohexene
(PCHE) and propylcyclohexane (PCH) (with the later
three designated C9 products) were observed in the
reaction products. There are two ways in which the
nitrogen atom can be removed: One path is via aromatic
intermediates THQ1 and OPA, and the other is via the
saturated intermediates DHQ and PCHA. The yields of
THQ1, THQ5, and DHQ passed through a maximum,
indicating that their rates of further reaction were much
greater than their rates of formation. No PCHA was
detected in the products, revealing that removal of
NH3 from PCHA to product PCHE is much faster
than the cracking of DHQ and the hydrogenation
of OPA to PCHA. The denitrogenated C9 products
showed continuously increasing yields and were the
final products of the quinoline reaction network.
As shown in Fig. 1, the selectivities of THQ1 and
THQ5 extrapolated nonzero values at space time zero,
suggesting that they were primary products. The selectivity of THQ1 is about 9 times that of THQ5 at
τ = 0.56, indicating that hydrogenation of quinoline
to THQ1 proceeds much easier than its hydrogenation
to THQ5, since the heterocyclic ring is more easily
hydrogenated than the benzenoid ring[12] . The selectivity of THQ1 decreased dramatically with increasing
space time, indicating that it converted further into
OPA and DHQ which were reaction intermediates. It
is noted that the selectivity of THQ5 increased from
about 8.0 to 19% when the space time increased from
0.56 to 3.75 min. This is partly because hydrogenation of quinoline is faster than further hydrogenation
of THQ5 at present conditions. This is well consistent
with the results reported by Prins et al .,[9] although the
reaction conditions were different. The selectivities to
OPA, DHQ, and C9 increase with the increase of space
time. The increases of C9 and OPA were more than
Asia-Pac. J. Chem. Eng. 2009; 4: 704–710
DOI: 10.1002/apj
705
Y. LUAN ET AL.
Asia-Pacific Journal of Chemical Engineering
80
80
Selectivity, %
(b) 100
Relative content, %
(a) 100
60
40
THQ1
THQ5
20
0
C9
OPA
Q
DHQ
0
1
2
3
4
5
6
60
40
THQ1
20
THQ5
C9
OPA
DHQ
0
7
0
1
2
Space time, min
3
4
5
6
7
Space time, min
Relative concentration of reactant and products (a) and product selectivities (b) of HDN of
quinoline as a function of space time at 340 ◦ C and 3.0 MPa. This figure is available in colour online at
www.apjChemEng.com.
Figure 1.
(a) 100
(b) 100
80
80
XQ
XN
40
60
XQ
X, %
60
X, %
706
XN
40
P=5.0 MPa
t=1.12 min
20
0
T=380°C
t=1.12 min
20
300
320
340
360
T, °C
380
400
420
0
2
4
P, MPa
6
Figure 2. The influence of temperature (a) and pressure (b) on hydrogenation and denitrogenation of
quinoline. This figure is available in colour online at www.apjChemEng.com.
that of DHQ. Meantime, further conversion of OPA was
inhibited by quinoline-type compounds because of their
stronger adsorption than that of OPA[13] .
The influences of temperature and pressure also on
the HDN of quinoline were investigated at a temperature between 300 and 420 ◦ C (Fig. 2a) and pressure between 2 and 6 MPa (Fig. 2b). The conversion
of quinoline increased slightly from 96.4 to 99.4%,
while HDN of quinoline increased drastically from 6.25
to 94.6% as the temperature increased from 300 to
420 ◦ C. The results show that the hydrogenation of
quinoline is much easier than the denitrogenation of its
intermediates, and the reaction temperature had a slight
effect on hydrogenation, but a drastic effect on nitrogen
 2009 Curtin University of Technology and John Wiley & Sons, Ltd.
removal. When the hydrogen partial pressure increased
from 2 to 6 MPa, the conversion of quinoline increased
from 57.5 to 99.4% and the denitrogenation of quinoline
increased from 8.5 to 96.8%, which demonstrated that
hydrogen pressure has a drastic effect not only on nitrogen removal, but also on hydrogenation of quinoline.
HDN of THQ1
The THQ1 is a key intermediate in the HDN network
of quinoline. In order to further understand the HDN
mechanism of quinoline, the HDN of THQ1 was also
studied at 340 ◦ C and 3 MPa in the presence of 1 mol%
Asia-Pac. J. Chem. Eng. 2009; 4: 704–710
DOI: 10.1002/apj
Asia-Pacific Journal of Chemical Engineering
HDN OF QUINOLINE AND ITS INTERMEDIATES
H2 S. As shown in Fig. 3a, the yield of quinoline reached
a maximum with the increase of space time, then
decreased slightly, while the yield of THQ5 increased
continuously with the increase of space time, indicating
that the formation of THQ5 mainly proceeds through
the pathway of THQ1–Q–THQ5. The yields of OPA,
DHQ, and C9 increased with the increase of space
time, but are lower than the sum of quinoline and
THQ5, indicating that dehydrogenation rate of THQ1
is much faster than the sum of hydrogenation rate and
hydrogenolysis rate of THQ1.
The sum of selectivities to quinoline and THQ5 is
about 8 times as high as the sum of selectivities to
OPA and DHQ at τ = 0.56 min (Fig. 2b), suggesting
that the dehydrogenation of THQ1 is much easier than
hydrogenolysis to OPA and hydrogenation to DHQ.
The selectivity to THQ5 increased at low space time
and decreased slightly at high space time. This can be
explained by the fact that THQ5 was further converted
to DHQ at high space time, i.e. τ = 5.6 min. The
selectivities of OPA and DHQ are almost equal at low
space time, while the selectivity of OPA was a little
higher than that of DHQ with increase in space time,
and hydrogenation of THQ1 to DHQ is easier than
hydrogenolysis to OPA[14] . It can be concluded that the
consumption of DHQ through C–N bond cleavage to
PCHA and C9 is much easier than further conversion
of OPA.
Figure 3 also shows that there are two paths for the
HDN of THQ1: via OPA–PB and via DHQ–PCHA.
The dehydrogenation of PCHE to PB was inhibited
completely in the presence of NH3 , which was formed
from breaking of the C–N bond of PCHA and OPA, and
the PB can hardly be further hydrogenated to PCH in
the presence of quinoline-type compounds[8] . Therefore
PB is formed only by hydrogenolysis of OPA, and
PCH is formed only through PCHA. The contribution
of two paths can be estimated from the ratio of PCH/PB
during the HDN of THQ1. PB was not detected at the
space time of 0.56 min, indicating the hydrogenolysis
of OPA did not take place and the HDN of THQ1
proceeds exclusively via DHQ–PCHA. The PCH/PB
ratio increases from 1.22 to 2.30 with the increase
of space time from 1.12 to 5.61, suggesting that the
contribution of DHQ–PCHA increased from 55% at
the space time of 1.12 min to 70% at the space time
of 5.61 min. This is in good agreement with the results
reported by Jian et al .[13] .
HDN of THQ5
The foregoing results also demonstrate that THQ5 is
an important intermediate and primary product in the
HDN of quinoline, as well as in the HDN of THQ1. To
further understand the HDN mechanism of quinoline,
THQ5 was used and its HDN reaction was studied
under the same conditions. As shown in Fig. 4a, the
concentration of DHQ went through a maximum then
decreased slightly and C9 increased continuously with
the increasing space time, whereas the concentration of
quinoline and THQ1 were always quite low, especially
quinoline. Thus, the HDN of THQ5 mainly proceeds
the path of via DHQ–PCHA–C9.
Figure 4b shows that the selectivity of DHQ extrapolated to nonzero values at space time zero, suggesting
that DHQ was the primary product. The selectivity to
(a) 100
(b) 70
60
80
Selectivety, %
Relative content, %
50
60
40
THQ1
40
THQ5
30
C9
Q
20
Q
20
0
0
1
THQ5
C9
OPA
DHQ
2
3
4
5
6
OPA
DHQ
10
7
Space time, min
0
0
1
2
3
4
5
6
7
Space time, min
Figure 3. Relative concentration of reactant and products (a) and product selectivities (b) of the HDN of
THQ1 as a function of space time at 340 ◦ C and 3.0 MPa. This figure is available in colour online at
www.apjChemEng.com.
 2009 Curtin University of Technology and John Wiley & Sons, Ltd.
Asia-Pac. J. Chem. Eng. 2009; 4: 704–710
DOI: 10.1002/apj
707
Y. LUAN ET AL.
Asia-Pacific Journal of Chemical Engineering
(b) 70
(a) 100
60
C9
80
Selectivity, %
50
Relative content, %
708
60
THQ5
40
40
30
DHQ
C9
20
DHQ
10
20
0
THQ1
Q
0
1
2
3
4
5
6
THQ1
Q
7
0
0
1
2
3
4
5
6
7
Space time, min
Space time, min
Relative concentration of reactant and products (a) and product selectivities (b) of the HDN of
THQ5 as a function of space time at 340 ◦ C and 3.0 MPa. This figure is available in colour online at
www.apjChemEng.com.
Figure 4.
DHQ decreases with increasing space time, while that
to C9 increases at a similar trend, indicating that DHQ
further converts to C9 via PCHA. The selectivities to
THQ1 and quinoline were almost constant with the
increasing space time, and the selectivity of THQ1 is
about 3.5 times as high as that of quinoline. This can
be understood as hydrogenation of quinoline to THQ1
is easier than the HDN of THQ5 to quinoline under
reaction conditions.
Effect of H2 S on HDN of quinoline
To further study the effect of H2 S on the HDN of
quinoline, we performed the HDN of quinoline at a
temperature of 340◦ and a pressure of 3 MPa, varying
from the absence of H2 S to a high percent of H2 S over
the sulfided NiW/γ -Al2 O3 (Table 1).
As shown in Table 1, the relative concentrations of
THQ5 and DHQ are lower in the presence than in the
absence of H2 S, while those of THQ1 and OPA are
considerably higher. The PCH/PB ratio increased from
1 to 2.15 with the increasing H2 S concentration, indicating that H2 S inhibits the pathway of OPA hydrogenolysis and promotes C–N bond cleavage to PCHA in
the THQ5–DHQ pathway. The results are in agreement with those reported in references [15–17]. This
can be indicated that H2 S retards the rate determining
of THQ1–OPA and promotes the rate determining reaction of DHQ–PCHA[9] . When the promoting effect was
superior to its inhibiting effect, C9 products would be
increased. At a high concentration of H2 S, the pathway
of OPA was severely blocked, causing a decrease in C9
yields.
 2009 Curtin University of Technology and John Wiley & Sons, Ltd.
DISCUSSION
The primary products in the HDN of quinoline were
THQ1 and THQ5, demonstrating that quinoline underwent only hydrogenation. In the HDN of THQ1, the primary products were quinoline, DHQ, and OPA, indicating that THQ1 underwent dehydrogenation, hydrogenation, and denitrogenation. In the HDN of THQ5, the primary products were quinoline and DHQ, demonstrating
that THQ5 underwent both dehydrogenation and hydrogenation. In the HDN of quinoline, THQ1, and THQ5,
the yield and selectivity of the denitrogenated hydrocarbons PB, PCHE, and PCH (C9 products) increased
continuously as a function of space time, demonstrating that they are the final products of the HDN reaction. There are two possible paths for the formation
of C9 products: via THQ1–OPA and via DHQ–PCHA.
Simultaneous HDN of o-ethyl aniline or DHQ and HDS
of thiophene showed that DHQ adsorbs much stronger
than o-ethyl aniline[18] . In the presence of DHQ, quinoline, and THQ, the rate of HDN of OPA is considerably
suppressed[19,20] . However, the THQ1–OPA reaction
path cannot be negligible and amounts to about 40%
of quinoline HDN[13] .
In the HDN of quinoline, the denitrogenation activity
increased drastically with increasing reaction temperature, while hydrogenation activity increased slightly,
indicating that the denitrogenation reaction has a higher
activation energy than hydrogenation reaction. This
finding is similar to that reported by Bunch et al .[21]
and Wang et al .[22] . Hydrogenation and dehydrogenation reactions increased and decreased, respectively,
with hydrogen partial pressure. The increasing hydrogen partial pressure has resulted to the drastic increase
Asia-Pac. J. Chem. Eng. 2009; 4: 704–710
DOI: 10.1002/apj
Asia-Pacific Journal of Chemical Engineering
HDN OF QUINOLINE AND ITS INTERMEDIATES
Table 1. Influence of H2 S on the HDN of quinoline.
Product composition (selectivity) (mol%)
H2 S (mol%)
0
1.0
1.8
3.6
7.2
C9
THQ5
OPA
THQI
DHQ
Q
PCH/PB ratio
5.0(5.7)
8.4(9.7)
5.8(6.8)
5.3(6.2)
5.1(6.0)
20.1(23.1)
14.9(17.2)
13.3(15.5)
11.7(13.7)
11.1(13.0)
1.8(2.1)
5.2(6.0)
7.3(8.5)
8.4(9.8)
10.1(11.9)
51.3(58.8)
52.5(60.7)
54.8(63.9)
56.4(66.0)
56.7(66.6)
9.0(10.3)
5.5(6.4)
4.8(5.6)
3.7(4.3)
2.5(2.9)
12.8
13.5
14.2
14.5
14.8
1
1.33
1.57
1.75
2.15
of hydrogenation and denitrogenation of quinoline. At
constant H2 S pressure, the increase of hydrogen partial pressure would increase the availability of spillover
hydrogen when weakly adsorbed THQ1 and OPA were
the main hydrogenated intermediates[23] . At the same
time, the contribution to the overall HDN of the
DHQ–PCHA pathway will also increase with increasing hydrogen partial pressure.
There are two reaction paths in the HDN of THQ1:
via OPA–PB and via DHQ–PCHA. The dehydrogenation of PCHE to PB was inhibited completely in the
presence of NH3 , which was formed from breaking
of the C–N bond of PCHA and OPA, and PB can
hardly be further hydrogenated to PCH in the presence of quinoline-type compounds[8] . Therefore, PB is
formed only by hydrogenolysis of OPA, and PCH is
formed only through PCHA. The contribution of the
two paths can be estimated from the amount of PB
and PCH formed during the HDN of THQ1. PB was
not detected at the space time of 0.56 min, indicating
that hydrogenolysis of OPA did not take place and the
HDN of THQ1 proceeds exclusively via DHQ–PCHA.
The PCH/PB ratio increases from 1.22 to 2.30 with
the increase of space time from 1.12 to 5.61 min, suggesting that the contribution of DHQ–PCHA increased
from 55% at the space time of 1.12 min to 70% at the
space time of 5.61 min. This is in good agreement with
the results reported by Jian et al .[16] .
The HDN of THQ5 under present conditions resembles that of DHQ[7] . Dehydrogenation of THQ5 to
quinoline and dehydrogenation of DHQ to THQ1 are
not easy and only proceed to a limited extent. The
reactions between THQ5, DHQ, THQ1 and quinoline
can rapidly reach a quasi equilibrium at a very low
space time, so the selectivities of THQ1 and quinoline are almost unchanged with increasing space time.
The denitrogenation reaction mainly takes place through
the pathway of DHQ–PCHA–C9, as the increased
selectivity of C9 is equal to the decreased selectivity
of DHQ.
H2 S has a dual effect on the HDN reactions[1,2,24] .
It slightly inhibits hydrogenation and dehydrogenation
but drastically promotes C–N bond cleavage. In the
HDN of quinoline, the concentration of OPA was
considerably higher, and that of DHQ was slightly
lower, in the presence than in the absence of H2 S.
 2009 Curtin University of Technology and John Wiley & Sons, Ltd.
From the former, it is understood that the transformation
of THQ1 to OPA is enhanced and further conversion
of OPA is inhibited by the presence of H2 S, while
the latter is that the transformation of DHQ to PCHA
and hydrocarbons is promoted by the presence of
H2 S. The results are in good agreement with those in
the literature[1,2,15 – 17] . In the meanwhile, this suggests
the presence of two active sites, those responsible
for the hydrogenation and dehydrogenation and those
promoting C–N bond breaking. H2 S has a different
effect on the two reactions and active sites. At low
concentration of H2 S, the promoting effect on C–N
bond breaking was superior to its inhibiting effect on
the hydrogenation and dehydrogenation, resulting in the
increase of OPA and C9 products. At high concentration
of H2 S, the pathway of OPA was severely blocked,
causing a decrease of C9 products and an increase
of OPA. The effect of H2 S on HDN reaction is in
accordance with the results of Lee et al .[12] .
CONCLUSION
To study the reaction network and mechanism of
the HDN of quinoline, we investigated the HDN of
quinoline as well as THQ1 and THQ5, the reaction
intermediates of the HDN network. Based on our
experimental results, temperature and pressure have
a drastic effect on nitrogen removal in the HDN of
quinoline. THQ1 mainly underwent dehydrogenation to
quinoline and then hydrogenated to THQ5 and DHQ
following by ring opening elimination to give PCHA
and C9. The HDN of THQ5 mainly proceeded via
the path of DHQ–PCHA–C9; the reactions between
THQ5, DHQ, THQ1 and quinoline are so fast that
a quasi equilibrium between the four compounds is
established at a very low space time. The addition
of H2 S promotes the reaction of DHQ, but retards
the pathway of OPA. The promoting effect of H2 S is
dominant at low concentration of H2 S. However, its
inhibiting effect prevails at high concentrations. The
HDN via the pathway of DHQ is much easier than
that of OPA over the sulfided NiW/γ -Al2 O3 . The HDN
of OPA was suppressed by the presence of quinoline,
THQ1, THQ5, and DHQ, possibly due to their stronger
adsorption on the catalyst.
Asia-Pac. J. Chem. Eng. 2009; 4: 704–710
DOI: 10.1002/apj
709
710
Y. LUAN ET AL.
Asia-Pacific Journal of Chemical Engineering
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DOI: 10.1002/apj
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presence, sulfide, absence, niw, intermediate, al2o3, hydrodenitrogenation, quinolinic, h2s
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