Journal of Natural Gas Chemistry 18(2009)

Production of propene from 1-butene metathesis reaction on

tungsten based heterogeneous catalysts
Huijuan Liu1,2 , Ling Zhang1,2 , Xiujie Li1 , Shengjun Huang1 , Shenglin Liu1 ,
Wenjie Xin1 , Sujuan Xie1 , Longya Xu1
1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
2. Graduate University of Chinese Academy Sciences, Beijing 100049, China
[ Received February 20, 2009; Revised March 24, 2009; Available online August 14, 2009 ]

Abstract
A new propene production route from 1-butene metathesis has been developed on heterogeneous 10WO3 /Al2 O3 -HY catalysts with different HY
contents. It is found that the catalysts play bi-functionally first for the isomerization of 1-butene to 2-butene and then for the cross-metathesis
between 1-butene and 2-butene to propene and 2-pentene. The combination of HY zeolite and Al2 O3 is prerequisite for the production of
propene. The propene yield keeps increasing with the HY content in the range of 1070 wt%, where 10WO3 /Al2 O3 -70HY exhibits the highest
propene yield. The MS-H2 -TPR and MS-O2 -TPO characterizations indicate that the increase of HY content in the catalysts weakens the
interaction between W species and supports, in contrast to the probability of coking on the metal species and acid sites.
Key words
propene; 1-butene; metathesis; 10WO3 /Al2 O3 -xHY; bifunction

1. Introduction zeolite composite can be a candidate for the production of

Demand for propene due to the increasing demand of
propene derivatives is growing rapidly in worldwide chem-
istry. The technology of propene production from olefin
metathesis has become a major focus research in recent years,
such as the Lummus ABB process, which converts ethene into
propene through cross-metathesis with 2-butenes over a het-
erogeneous metathesis catalyst [14].
According to reaction equations based on widely accepted
carbene mechanism, propene can be obtained only between
the terminal and internal alkenes, i.e. 1-butene and 2-butene.
For the recent published results [5], propene can not be ob-
tained by pure 1-butene feed over homogeneous Grubbs first
generation-type ruthenium catalysts. As a result, the commer-
cial application of Phillips Triolefin Process (now licensed as
ABB OCT) and Shell Higher Olefin (SHOP) used isomeriza-
tion catalysts system to get 2-butene from 1-butene or ethene
before the metathesis reaction [4].
An alternative way to produce propene is the auto-
metathesis of 1-butene over bifunctional catalysts with both
isomerization as well as metathesis activity. In this light,
metal oxide (MoO3 or WO3 ) supported on acidic alumina-
propene from pure 1-butene.
The aim of the present work is to report a heterogeneous
catalyst, i.e. 10WO3 /Al2 O3 -HY, as well as its catalytic perfor-
mance in the 1-butene metathesis reaction. A series of cata-
lysts with different HY contents in support are evaluated. The
results indicate that the catalytic performances are remarkably
influenced by HY content in 10WO3 /Al2 O3 -HY catalysts.
The propene molar yield can achieve 21% and 19% on
10WO3 /30%Al2 O3 -70%HY and 10WO3 /50%Al2 O3 -50%HY
respectively. The initial catalytic activity can be correlated
with the state of tungsten oxide species as a function of HY
content. Furthermore, the coking behavior evidenced by TPO
profiles is closely associated with the transformation of tung-
sten oxides and acidity of the catalysts, which will lead to
remarkably different stability in the metathesis reaction.
2. Experimental
2.1. Catalyst preparation and its evaluation
Al2 O3 -HY support was prepared by extruding a mixture
of -Al2 O3 powder and HY zeolite (Wenzhou Zeolite Manu-

Corresponding author. Tel: +86-411-84693292; Fax: +86-411-84693292; E-mail: lyxu@dicp.ac.cn

This work was supported by the National Natural Science Foundation of China (No.20773120) and National 973 Project of China (No. 2005CB221403)

Copyright2009, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. All rights reserved.
doi:10.1016/S1003-9953(08)60113-9
2 Huijuan Liu et al./ Journal of Natural Gas Chemistry Vol. 18 No. 3 2009
facture of China, Si/Al2 = 10, Na2 O<0.2 wt%) at desirable
weight percent into strips with a diameter of about 2 mm. The
drawn extrudate was left at room temperature for a few hours
and placed in an oven at 393 K for 12 h. Subsequently, the
dried extrudate was calcined at 773 K for 2 h and then ground
into 1632 mesh.
Catalysts containing 10wt% tungsten were prepared by
impregnation of the Al2 O3 -HY support with ammonium
metatungstate solution according to the incipient wetness
method. The impregnated samples were dried at 393 K for
5 h, and then calcined at 873 K for 2 h. These prepared cat-
alysts are denoted as 10WO3 /Al2 O3 -xHY, where x indicates
the weight percent of HY zeolite in the Al2 O3 -HY support.
The catalysts were evaluated in a fixed-bed flow micro-
reactor of 10 mm inner diameter, and 3 g of catalyst with an
average particle size of 0.561.3 mm was loaded. An EU-2
type thermocouple was fixed in the middle of the catalyst
bed and taken as the reaction temperature. Before evalua-
tion, the catalysts were pretreated at 773 K in high purity
N2 (30 ml/min) for 1 h, then it was cooled down to the de-
sired reaction temperature. The typical reaction conditions are
as follows: temperature = 453 K, pressure = 0.1 MPa; WHSV
(1-C4 H8 ) = 1.5 h1 , and catalyst = 3.0 g. The reaction prod-
ucts are analyzed by a Varian 3800 gas chromatograph
equipped with an FID detector and a 50 m Al2 O3 -plot column.
2.2. Product analysis
Reaction of 1-butene on 10WO3 /Al2 O3 -xHY catalysts
W (C= n)
X
Y (C= ) =
W (C= = =
2 ) + W (C3 ) + W (C4 ) + W (C5 ) + W (C6 ) + W (C7 ) + W (C8 )
n
2 3 4 5
In the formula, Y (C=
n ) is the yield of olefin with carbon
number n, X is the 1-butene conversion, and W (C= n ) denotes
mass percent of alkene component with different carbon num-
ber n.
2.3. Catalyst characterization
X-ray diffraction (XRD) measurements were made with
an Xpert PRO/PANalytical Diffractometer using Cu-K ra-
diation and operated at 40 kV and 40 mA, with a scanning
speed of 5 o /min. Patterns were recorded from 5o to 70o (2).
Under 10% H2 /Ar flow (20 ml/min), H2 -TPR profiles
were obtained in the range of ambient to 1073 K at a pro-
grammed temperature rate of 14 K/min after the samples had
been pretreated in an Ar flow at 773 K for 30 min. The re-
duction was monitored by QMS (oministar) instrument, using
the fragments with m/e of 18 as the representative of water
which were formed from oxidation of H2 .
Coke deposition on spent 10WO3 /Al2 O3 -xHY catalysts
was determined by temperature programmed oxidation (O2 -
TPO). 0.08 g sample was loaded into a U-shaped quartz
micro-reactor. The catalyst was heated from 323 to 1123 K in
a 10% O2 /Ar stream. The heating rate was 10 C/min, and the
may include isomerization, self-metathesis, second metathesis
reaction and possible olefin oligomerization as shown below:
Scheme 1. Scheme of isomerization, self-metathesis, second metathesis re-
action and possible olefins oligomerization
It is hard to make a comprehensive list of all the reactions
and products due to the complicated side reactions and cross-
metathesis reactions. GC results indicate that cis, trans-2-
pentene and cis, trans-3-hexene are the major products for
C5 and C6 component. For a simple treatment, we denote
products with the same carbon number as C= n , where n repre-
sents carbon number. At the same time, all the heavy products
in C7 C10 range are denoted as C7+ .
The 1-butene conversion is determined by the mass per-
centage in the exhaust gas, and the molar yield of products is
calculated by the following equation:
n
= = = =
6 7 8
O2 /Ar flow rate was 50 ml/min. The carbon was monitored by
QMS (oministar) instrument, using the fragments with m/e of
28 and 44 as the representative of carbon monoxide and car-
bon dioxide.
3. Results and discussion
3.1. Catalytic performance of 10WO3 /Al2 O3 -xHY catalysts
Table 1 shows the activity and selectivity of 10WO3 /
Al2 O3 -xHY catalysts as a function of HY zeolite content. The
catalytic performance of catalysts depends on HY content in
the support. Although all the catalysts exhibit high 1-butene
conversion, the product distributions are quite different.
10WO3 /Al2 O3 proceeds metathesis reaction with 88.9%
1-butene conversion at 453 K, while the total metathesis activ-
ity is very poor with 0.5% molar yield. The primary products
are cis-2-butene and trans-2-butene, indicating the predomi-
nance of isomerization reaction. This is in fair agreement with
reference results, which always report poor low metathesis ac-
tivity for WO3 /-Al2 O3 under relatively mild conditions [1].
A remarkable change in distributions of products has been ob-
 Journal of Natural Gas Chemistry Vol. 18 No. 3 2009 3

served with increasing HY contents. As shown in Table 1, and C=5 yields are around 20% and 15%, whereas C2 and
=

1-butene conversion on 10WO3 /Al2 O3 -10HY slightly in-
creases to 93.3%, while propene yield achieves 9.8%. In the
range of 10wt%70wt% HY content, the propene yield keeps
increasing with higher HY content. The maximum propene
yield of 21.4% belongs to 10WO3 /Al2 O3 -70HY. However,
further higher HY content will lead to a decreased yield as
18.6% on 10WO3 /Al2 O3 -90HY. As another extreme exam-
ple, the propene yield on 10WO3 /HY dramatically decreases
to 1.4%. Upon the active 10WO3 /Al2 O3 -xHY catalysts, C= 3
C=6 yields are just around 1% and 5%, respectively. This
suggests 1-butene metathesis does not proceed through self-
metathesis reaction but through cross-metathesis route be-
tween 1-butene and 2-butene. Such low ethene yield also sug-
gests consumption of this product by successive secondary
cross-metathesis reactions. As a comparison, the yield of
propene is quite higher than that of associated C= 5 prod-
ucts, which is supportive for the contribution from cross
metathesis reactions.

Table 1. Reaction performance of 10WO3 /Al2 O3 -xHY with different HY contents

1-C=
4 conversion Metathesis yield (%) Polymerization Isomerization yield (%)
Catalyst
(%) C=2 C=
3 C= 5 C=6 yield (%) cis-2-C=
4 trans-2-C=4
10WO3 /Al2 O3 88.9 0 0 0.3 0.2 4.2 30.3 53.1
10WO3 /Al2 O3 -10HY 93.3 0.3 9.8 9.1 2.3 13.8 19.9 37.2
10WO3 /Al2 O3 -30HY 93.9 0.6 14.0 12.6 3.9 11.6 17.4 32.2
10WO3 /Al2 O3 -50HY 94.9 1.0 19.6 14.7 4.7 10.7 14.8 27.9
10WO3 /Al2 O3 -70HY 95.4 1.1 21.4 15.8 4.6 5.7 16.0 30.1
10WO3 /Al2 O3 -90HY 92.9 1.1 18.6 15.1 3.1 2.2 20.7 31.5
10WO3 /HY 80.5 0.1 1.4 1.4 0.3 0.5 34.1 41.9
Reaction conditions: T = 453 K; P = 0.1 MPa; WHSV = 1.5 h1 ; time on stream = 1 h

The propene yield of 10WO3 /Al2 O3 -xHY catalysts as a
function of time is compared in Figure 1(a). Low yields
(<10%) are still observed on 10WO3 /HY, 10WO3 /Al2 O3 , and
10WO3 /Al2 O3 -10HY with extended reaction time of 10 h.
Whereas for the active 10WO3 /Al2 O3 -xHY (30 wt%90 wt%
HY) catalysts, propene yield increased in the initial 5 h on
each sample, indicating the presence of induction period.
The induction time was also observed on WO3 /SiO2 , in-
dicating a period was needed to form active metal-carbene
species [1]. But such phenomena were not observed in
metathesis of ethene and 2-butene with the same WO3 /Al2 O3 -
xHY catalysts [6]. Although the reason is not clear, this may
suggest the difference in the interaction between substrate
alkenes and tungsten oxide species for the initial formation
of active metal-carbene species.
Figure 1(a) displays that the maximum propene yield of
25% belongs to 10WO3 /Al2 O3 -70HY after the initial in-
duction period. However, the propene yield on the cata-
lyst sharply decreases after 17 h running time, and only 5%
yield can be obtained at 30 h time on stream. As a com-
parison, catalysts with lower HY content show better stabil-
ity despite their slightly lower initial metathesis activity. For
example, the propene yield on 10WO3 /Al2 O3 -50HY can still
achieve 17% after 30 h time on stream. While on the same
WO3 /Al2 O3 -xHY catalysts for the metathesis between ethene
and butene to propene, the stability of catalyst increases with
propene selectivity [6], indicating the other different reaction
behavior of 1-butene on WO3 /Al2 O3 -xHY catalysts.
Since propene is from cross-metathesis between 1-butene
and 2-butene, the variation of 2-butene yield and 1-butene
conversion were also compared.
2-butene yield on 10WO3 /Al2 O3 and 10WO3 /Al2 O3 -
10HY are high and stable, indicating the two catalysts are ac-
tive for 1-butene isomerization reaction. The 2-butene yield
on 10WO3 /Al2 O3 -30HY and 10WO3 /Al2 O3 -50HY shows al-
most the same tendency, on which 2-butene yield increases

Figure 1. Comparison of 10WO3 /Al2 O3 -xHY reaction performance. (a) Propylene yield, (b) 2-butene yield, (c) 1-butene conversion. () 10WO3 /Al2 O3 ,
() 10WO3 /Al2 O3 -10HY, () 10WO3 /Al2 O3 -30HY, () 10 WO3 /Al2 O3 -50HY, () 10WO3 /Al2 O3 -70HY, ()10WO3 /Al2 O3 -90HY, (N) 10WO3 /HY
4 Huijuan Liu et al./ Journal of Natural Gas Chemistry Vol. 18 No. 3 2009
with time on stream, indicating more 1-butene converts to
2-butene on these catalysts. For 10WO3 /Al2 O3 -70HY and
10WO3 /Al2 O3 -90HY 2-butene yield decreases first and then
increases. As for 10WO3 /HY catalysts, 2-butene yield de-
creases rapidly with time on stream, suggesting a fast deacti-
vation on the catalyst.
The initial 1-butene conversion on various catalysts was
close to 90% except a lower value of 80% on 10WO3 /HY.
The most distinct difference was observed in the variation
of 1-butene conversion as the function of time on stream.
1-butene conversions are quite stable on 10WO3 /Al2 O3 -xHY
with HY content lower than 50%. However, higher HY con-
tent will lead to a sharper decrease of 1-butene conversion.
Especially for 10WO3 /HY, the 1-butene conversion undergoes
a sharp decrease to 43% within 10 h. At the same time, the
2-butene yield on 10WO3 /HY decreases correspondingly to
40% in 10 h. From the sharp decrease of 1-butene conver-
sion and 2-butene yield, it is inferred that a significant reduc-
tion of accessible acid sites on 10WO3 /HY takes place in the
process of 1-butene conversion, these are the active sites for
double bond isomerization reaction [7,8].
As shown in Figure 1(b) and (c), the decrease of HY
content in support leads to improved performance for the
1-butene conversion and isomerization to 2-butene. The less
active metathesis catalysts of 10WO3 /Al2 O3 , 10WO3 /Al2 O3 -
10HY and 10WO3 /Al2 O3 -30HY give higher and more stable
2-butene yields. Whereas, such isomerization product yields
on 10WO3 /Al2 O3 -70HY and 10WO3 /Al2 O3 -90HY gradually
increase after the decrease in the initial reaction stage.
According to the results in Table 1 and Figure 1, com-
bination of Al2 O3 and HY in appreciable ratio is a prereq-
uisite for the high active catalysts in 1-butene metathesis,
which has also been observed in the metathesis reaction be-
tween ethene and 2-butene [6,9]. In preceding study, such
support effect has been related with acidity, interaction be-
tween metal species and support, and variation of tungsten ox-
ide species [6]. In the case of 1-butene substrate, the distinc-
tive differences in metathesis catalytic performance, isomer-
ization and 1-butene conversion suggest more understandings
of support effect apart from other viewpoints as a function of
HY content.
3.2. Characterization results and discussion
XRD patterns of WO3 species loaded on Al2 O3 -xHY sup-
ports with different HY contents are shown in Figure 2. The
X-ray diffraction patterns do not show any evidence of the
WO3 phase on 10WO3 /Al2 O3 -xHY with the HY contents
in the range of 070 wt%, indicating a good dispersion of
tungsten species on these supports, or small crystallite ag-
glomerates are outside the XRD crystallite size detection lim-
its. As for 10WO3 /Al2 O3 -90HY and 10 WO3 /HY, there are
obvious WO3 phase formed. The intensities of sharp HY
characteristic peaks increase with increase of HY content in
the Al2 O3 -HY support. The coexistence of broad -Al2 O3
(2 = 37.39o, 45.95o, and 67.06o) and sharp HY characteris-
tic peaks is shown in samples with HY content below 70 wt%.
Only HY characteristic peaks, except their difference in inten-
sity, appear as the HY content is higher than 70 wt%, due to
the decrease of Al2 O3 content as well as the lower sensitivity
of Al2 O3 to the X-ray compared with HY zeolite.
The poor performance of WO3 /Al2 O3 for 1-butene
metathesis reaction was partially attributed to the lower
Bronsted acidity [6]. However, the high 2-butene yield over
10WO3 /Al2 O3 in Figure 1(b) excludes the potential limita-
tion of acidity on the isomerization for the cross-metathesis
reaction between 1-butene and 2-butene. In our case, one
of the driving force for the zeolite-alumina composite is to
improve the Bronsted acidity of catalysts, which can interact
with metal species and results in the active sites precursors
[10]. According to previous characterization results by NH3 -
TPD and pyridine-IR adsorption [6], the increase of HY zeo-
lite content enhances the total acidity and Bronsted acidity of
catalysts proportionally. As shown in Figure 1 and Table 1,
the initial propene yield increases stepwise with higher HY
content within 70 wt% range. However, catalysts with further
higher HY content, especially 10WO3 /HY, undergo dramatic
decrease in metathesis activity despite the steadily enhanced
acidity. This suggests that the metathesis activity of 1-butene
is controlled not only by the catalyst Bronsted acidity and to-
tal acidity, but also by the other factors such as the oxidization
number of W species, the reducibility of catalyst and coordi-
nation geometry of W species etc.
Figure 2. XRD patterns of 10WO3 /Al2 O3 -xHY catalysts
Interaction between W species and the Al2 O3 -HY sup-
port was investigated by the H2 -TPR technique. In this pa-
per, typical comparisons of fresh and spent catalysts such as
10WO3 /HY and 10WO3 /Al2 O3 -70HY were made by MS-H2 -
TPR as shown in Figure 3. A higher-temperature peak de-
noted as h existed in all of the investigated samples, but for
 Journal of Natural Gas Chemistry Vol. 18 No. 3 2009
the spent 10WO3 /HY catalyst, it was almost vanished; as for
the fresh and spent 10WO3 /Al2 O3 -70HY catalysts, it shifted
to higher temperature, suggesting an enhancement of inter-
action between W species and the supports with increase of
HY contents. After 1 h time on stream, the curve of spent
10WO3 /Al2 O3 -70HY was similar to that of fresh catalyst, in-
dicating there was little variation of tungsten species from the
original state after 1 h introduction of alkene. The profile of
fresh 10WO3 /HY catalyst exhibited two reduction peaks, de-
noted as l and h, suggesting that the 10WO3 /HY was sub-
ject to the deep reduction by alkenes under reaction condition.
However, the reduction peak of h at higher temperature almost
disappeared after 1 h reaction under the 1-butene atmosphere
indicating a complete reduction of high-valence W species in
a short time on 10WO3 /HY catalyst. This might also reflect
the serious coking on 10WO3 /HY.
Figure 3. Comparison of reducibility between fresh and spent
10WO3 /Al2 O3 -xHY catalysts
O2 -TPO was used to characterize the coke species on
10WO3 /Al2 O3 -xHY catalysts after reaction. As shown in
Figure 4, all catalysts display coke burning peaks after re-
action, and the shape and maxima temperatures (Tmax ) of
the profiles strongly depend on the HY contents. The spent
10WO3 /Al2 O3 has two overlapping peaks centered at 673 and
783 K, respectively. With the increase of HY content in sup-
port, the intensities of both peaks increase, accompanied by
the shift to the higher temperature. When HY content reaches
50%, a small burning peak appears at 550 K. For 10WO3 /HY,
the profile undergoes a remarkable change. The former burn-
ing peak shifts oppositely to lower temperature of 660 K with
the presence of more intensive peak at 550 K. Sachtler et al.
[11] investigated typical TPO profiles of a bifunctional cat-
alyst and assigned the first peak at lower temperature to the
coke oxidation catalyzed by metal and the broad one at higher
temperature to coke oxidation from the covered acid sites. As
shown in Figure 4, coke species related with acid sites become
much more severe with increase of HY content, which agrees
well with the variation of acidity as the function of HY con-
tent in NH3 -TPD and Py-IR [6]. For coke species related with
5
metal species, similar trend can be observed on the catalysts
except 10WO3 /HY. This indicates the differences of tungsten
oxide species over HY, -Al2 O3 and -Al2 O3 -HY. As char-
acterized by H2 -TPR, the increase of HY zeolite weakens the
metal-support interaction, and leads to the increased lateral
interaction among tungsten oxide species on support. As a
result, the structure of tungsten oxide species will change ac-
cordingly.
Figure 4. O2 -TPO profiles of 10WO3 /Al2 O3 -xHY catalysts
It is well reported that tungsten oxide species will
be present as isolated tetrahedral species on low loading
WO3 /Al2 O3 [12,13]. By preceding Raman results [14], char-
acteristic band of W=O bonds (970 cm1 ) in distorted
tetrahedral state can be observed on 10WO3 /Al2 O3 . With
the increase of HY content, tungsten species will turn into
surface poly-tungsten oxide species with W-O-W linkages
(broad band in 840880 cm1 ). For 10WO3 /HY, the tung-
sten species will turn into small crystallites and WO3 -like
polytungstate (overlap bands around 805, 706 and 273 cm1
band). A positive correlation between tetrahedral tungsten ox-
ide species and metathesis activity has been displayed, sug-
gesting these species to be active sites precursors in reaction
between ethene and 2-butene [6,9,11]. Since the quite similar
reaction atmosphere, the active sites precursors in 1-butene
metathesis should also include these tetrahedral tungsten ox-
ide species. Combining the transformation of metathesis ac-
tivity and O2 -TPO profiles, the increase of HY zeolite content
will not only improve the amount of the active sites precur-
sors, but also promote the coking related with side reactions.
In the case of 10WO3 /HY, the most severe coking behavior
can be observed in the presence of poly-tungsten oxide and
WO3 -like polytungstate species. Instead of being active in
metathesis activity, these species can catalyze the coke forma-
tion related with side reactions of alkene substrates, leading to
6 Huijuan Liu et al./ Journal of Natural Gas Chemistry Vol. 18 No. 3 2009
further blockage of tungsten species and acid sites. This can
explain the poor metathesis activity and simultaneous quick
deactivation of 1-butene isomerization on 10WO3 /HY.
In summary, the incorporation of HY zeolite in 10WO3 /
Al2 O3 support affects the acidity of catalyst, metal-support in-
teraction and tungsten active sites, which are responsible for
the metathesis activity and catalyst stability.
4. Conclusions
The heterogeneous 10WO3 /Al2 O3 -xHY catalysts
presents a good performance on the metathesis of 1-butene for
the production of propene. The 1-butene metathesis catalyzed
by 10WO3 /Al2 O3 -xHY catalysts does not proceed through
the self-metathesis reaction but through the cross-metathesis
route between 1-butene and 2-butene which is obtained from
the isomerization of 1-butene. The metathesis activity is
influenced both by the Bronsted acidity of samples and the
state of tungsten oxide species. Especially, the increase of
HY zeolite content in the 10WO3 /Al2 O3 -xHY samples has
the conflicting effects: improves the amount of the active
sites precursors and promotes the coking from side reactions.
10WO3 /Al2 O3 -xHY catalysts with 50wt%70wt% HY con-
tent show good 1-butene conversion, as well as propene yield
due to their suitable Bronsted acidity and suitable interaction
between W species and supports for the formation of active
sites precursors.
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