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Influence of nanoparticles oxidation state in gold based catalysts on the

product selectivity in liquid phase oxidation of cyclohexene

Article  in  Journal of Molecular Catalysis A Chemical · August 2013

DOI: 10.1016/j.molcata.2013.03.008

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 Journal of Molecular Catalysis A: Chemical 374–375 (2013) 1–6

Contents lists available at SciVerse ScienceDirect

Journal of Molecular Catalysis A: Chemical

journal homepage: www.elsevier.com/locate/molcata

Influence of nanoparticles oxidation state in gold based catalysts on the product

selectivity in liquid phase oxidation of cyclohexene
N. Ameur, S. Bedrane, R. Bachir ∗ , A. Choukchou-Braham
Laboratory of Catalysis and Synthesis in Organic Chemistry, Université de Tlemcen, BP 119 Imama, 13000 Tlemcen, Algeria

a r t i c l e i n f o a b s t r a c t

Article history: Supported gold catalysts Au/TiO2 and Au/ZrO2 were prepared and used for oxidation of cyclohexene with
Received 17 May 2012 TBHP. These catalysts were characterized by ICP, TEM and diffuse-reflectance UV–vis. The catalytic tests
Received in revised form 28 February 2013 were carried out in liquid phase, at 80 ◦ C and at atmospheric pressure.
Accepted 3 March 2013
The effects of support and thermal treatment (oxidation state of Au nanoparticles) on catalytic perfor-
Available online xxx
mance were studied. Gold in the catalysts that have been dried is deposited as Au␦+ . These catalysts have a
high selectivity towards alkene oxides, 81% of 2-cyclohexene-1-ol for Au/TiO2 and 85% of 2-cyclohexene-
Keywords:
1-one for Au/ZrO2 .
Gold
Nanoparticles © 2013 Elsevier B.V. All rights reserved.
Oxidation
Cyclohexene
Selectivity

1. Introduction The objective of this work is to study the influence of gold

Catalytic oxidation of olefins into value added oxygenated
derivative is very important in chemical industry [1]. The oxi-
dation of cyclohexene can give rise to a number of products
(Scheme 1) depending on the catalysts and reaction conditions.
The 2-cyclohexene-1-ol and 2-cyclohexene-1-one are used in the
manufacture of high value pharmaceutical chemicals [2]
In the past decades, an increasing interest has been directed to
the catalytic potential of gold catalysts. Gold-based catalysts are
used in different reactions of carbone oxidation, such as oxidation
of CO [3–14], oxidation of sugar [15], oxidation of benzylaco-
hol [17–20], oxidation of aliphatic alcohols [21–23], oxidation of
polyols [16,24,25], oxidation of glycerol [26,27] epoxidation of
trans-stilbene [28,29], epoxidation of styrene [30,31] oxidation of
cyclohexane [32–34,37].
However, the literature reports few studies on the use of gold
catalysts for the oxidation of cyclohexene, except those of Zhen-
Cai et al. about Au/OMS-2(La-OMS-2) [38] and Au/HNTs [39]. They
report that conversion does not exceed 50% and selectivity to 2-
cyclohexene-1-ol and 2-cyclohexene-2-one is between 30 and 49%.
In addition, supported gold nanoparticles on C [1] and CNTs [40]
showed a remarkable catalytic activity for this reaction.
nanoparticles oxidation state, on the oxidation of cyclohexene by
TBHP. TiO2 and ZrO2 oxides are used as supports because they have
comparable acidities but different reducibility features.
2. Experimental
2.1. Catalysts preparation
A suspension of support (TiO2 or ZrO2 ) in distilled water is
introduced into a three-necked flask and heated to 80 ◦ C. Then,
a solution of gold salt, HAuCl4 ·3H2 O, (10 g/L) is mixed with urea
(0.9 g). All is closed and stirred for 16 h at the same temperature in
the dark. At the end, the solid is separated by centrifugation and
washed with distilled water many times.
After each washing, a test with (AgNO3 ) is carried out to verify
the presence of chlorides. Generally, after the first wash, no trace of
chloride is found. A second qualitative test was also carried out on
the wash solution by NaBH4 . No changes in the wash solution color
indicate that the total amount of the introduced gold is deposited
on oxides. The resulting solids are dried at 120 ◦ C overnight (dried
catalyst). A part of the dried samples are then reduced by hydrogen
at 300 ◦ C (reduced catalyst), and are stored in a vacuum desiccator,
protected from light [34,38,41,42].

2.2. Catalysts characterization

∗ Corresponding author. Tel.: +213 43 213198; fax: +213 43 213198.
E-mail addresses: redouane bachir@hotmail.com, The effective contents of Au and Cl in the catalysts were deter-
redouane.bachir@mail.univ-tlemcen.dz (R. Bachir). mined by ICP chemical analysis. TEM photographs were obtained

1381-1169/$ – see front matter © 2013 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.molcata.2013.03.008
2 N. Ameur et al. / Journal of Molecular Catalysis A: Chemical 374–375 (2013) 1–6

Scheme 1. Products resulting from the cyclohexene oxidation.

Table 1
Analysis of the catalysts.

Sample Nominal content (wt%) d (nm)

Au Cl

Au/TiO2 0.9 0.02 3.4

Au/ZrO2 0.8 <0.02 6.0

from a JOEL JEM-100CXII instrument, operating at 120 KV with

a resolution of 0.35 nm. Diffuse reflectance UV–vis spectroscopy
measurements were carried out at room temperature with Lambda
800 UV/Vis spectrometer in the range of 200–800 nm. This setup
was equipped with a diffuse reflectance accessory set to collect the
diffuse reflected light only.

2.3. Catalytic tests

Catalytic tests were performed using 0.1 g of catalyst, 4 mL of

cyclohexene and 5.5 mL of tert-butyl hydroperoxide [TBHP (70%) in
water]. The oxidation of cyclohexene was carried out at 70 ◦ C for
6 h under atmospheric pressure.
The consumption of TBHP was determinate by iodometric titra-
tion, and the products were analyzed by gas chromatography (GC
SCHIMADZU 14-B) with a capillary column “HP-FFAP” and an FID
detector.
The oxidation activity is expressed in TON (turnover number),
calculated at the end of the reaction (6 h) as follows:

n0 .C%
TON =
mcat .%AuD

n0 : initial mole number of cyclohexene, C%: cyclohexene con-

version, mcat : amount of catalyst, %Au: gold loading, D: gold
accessibility is calculated considering the hypothesis according to
which the particles are regarded as cubes with one face in contact
with the support and the five others are accessible [43].

3. Results and discussion

3.1. Catalysts characterization

The catalysts metal loading analysis shows that the majority of

the dissolved gold is deposited onto the oxides (Table 1).
The characterization by TEM of reduced Au/TiO2 (Fig. 1a) reveals Fig. 1. TEM characterization of reduced Au/TiO2 (a) TEM image (b) size distribution
the presence of gold nanoparticles, uniformly distributed on the histogram.
 N. Ameur et al. / Journal of Molecular Catalysis A: Chemical 374–375 (2013) 1–6
Fig. 2. TEM characterization of reduced Au/ZrO2 (a) TEM image (b) size distribution
histogram.
surface of TiO2 , with an average size of 3.4 nm. The histogram of
the particle size distribution has a Gaussian shape (Fig. 1b).
For reduced Au/ZrO2 (Fig. 2a), the gold nanoparticles are irreg-
ularly distributed on the surface of ZrO2 , with an average size of
about 6.0 nm. The histogram of size distribution is bimodal. It indi-
cates the presence of particle sizes of 2–3 nm and 7–8 nm (Fig. 2b).
Diffuse-reflectance UV–visible spectra of TiO2 oxide and
Au/TiO2 (dried and reduced catalysts) are shown in (Fig. 3). TiO2
spectrum (Fig. 3a) has a broadband between 210 nm and 340 nm.
This band is characteristic of the anatase phase [44]. It corresponds
to transitions of Ti4+ ions in a tetrahedral and an octahedral envi-
ronment [45–47].
The spectrum of dried Au/TiO2 catalyst (Fig. 3b) shows that the
introduction of gold leads to a decrease of the spectrum inten-
sity compared to TiO2 alone, particularly the characteristic bands
of anatase phase for TiO2 (200–350 nm). This is due to deposition
of gold particles. It seems that these particles cover the surface of
TiO2 , i.e. Ti4+ sites, and reduce the contact of UV radiation with the
support [35,36].
3
Fig. 3. Diffuse-reflectance UV–visible spectrum (a) TiO2 , (b) dried Au/TiO2 and (c)
reduced Au/TiO2 .
The comparison of the deconvoluted UV–vis spectra of TiO2 and
dried Au/TiO2 (Fig. 4) reveals the presence of three new bands at
213 nm, 231 nm and 328 nm in the case of dried Au/TiO2 . They are
characteristic of Au3+ , Au+ and Au␦+ , respectively [48]. However, no
change in the range (400–800 nm) of the dried Au/TiO2 spectrum
is shown. This indicates that this catalyst contains only oxidized
species (Au3+ , Au+ , Au␦+ ) and no reduced ones (Au0 ).
The Diffuse-reflectance UV–visible spectrum of the reduced
Au/TiO2 catalyst (Fig. 3c) shows a band between 200 and 350 nm
which is substantially identical to that of TiO2 . However, a new
large band appears with a maximum at 537 nm. This band is char-
acteristic of the reduced gold nanoparticles plasmon resonance. It
is influenced by the size, the shape of gold nanoparticles and their
environment (support) [49,50]. This result indicates that all gold
particles were reduced after treatment in H2 at 300 ◦ C.
Diffuse-reflectance UV–vis spectra of ZrO2 oxide and Au/ZrO2
(dried and reduced catalysts) are shown in (Fig. 5). The spectrum of
ZrO2 (Fig. 5a) shows a characteristic band of the tetragonal phase
at 235.32 nm. It is due to the electronic transition between Zr4+ and
oxygen [51,52]
On the Au/ZrO2 dried catalyst spectrum (Fig. 5b), the support
band disappears and a characteristic band of oxidized gold species
Au3+ appears at 257.24 nm [48].
On the reduced catalyst spectrum (Fig. 5c), it is clearly seen
that the characteristic band of the oxidized species Au3+ disap-
pears. The characteristic band of the support (ZrO2 ) reappears with
a slight shift from 235.32 nm to 227 nm. This shift is related to
metal-support interactions [53]. In addition, a characteristic band
of reduced gold nanoparticles plasmon resonance with spherical
shapes appears at 540.37 nm. Thus, just like Au/TiO2 , all the gold
particles were reduced after treatment in H2 at 300 ◦ C.
The characterization of the samples, dried and reduced by
Diffuse-reflectance UV–vis spectroscopy, shows that gold is
deposited in an oxidation state (Aun+ ); they remain with this oxi-
dation state even after drying. Their reduction to Au0 is done after
heat treatment in H2 at 300◦ C.
3.2. Cyclohexene oxidation
The reaction of cyclohexene oxidation can give six prod-
ucts (Scheme 1): 2-cyclohexene-1-ol (enol); 2-cyclohexene-1-one
(enone); cyclohexene epoxide (PO); cyclohexanol (ol); cyclohex-
anone (one) and cyclohexene-1,2-diol. It is worth mentioning that
in all the reactions conducted, the cyclohexene-1,2-diol was never
detected.
4 N. Ameur et al. / Journal of Molecular Catalysis A: Chemical 374–375 (2013) 1–6

Fig. 4. Deconvoluted bands of diffuse-reflectance UV–vis spectra of (a) TiO2 , and (b) dried Au/TiO2 .

Dried Au/ZrO2 is very selective towards 2-cyclohexen-1-one

Fig. 5. Diffuse-reflectance UV–vis spectrum (a) ZrO2 , (b) dried Au/ZrO2 and (c)
reduced Au/ZrO2 .
The results of activity and selectivity of the four catalysts are
summarized in Table 2. The TONs of the dried catalysts are respec-
tively 217 and 1090 for Au/TiO2 and Au/ZrO2 . Reduction induces an
increase of TON to 913 in the case of Au/TiO2 , and a decrease it in
the case of Au/ZrO2 .
Comparing the selectivities on dried and reduced catalysts, it
is clear that with dried Au/TiO2 , only cyclohexene-1-ol (81.1%)
and 2-cyclohexen-1-one (18%) are obtained, whereas with reduced
Au/TiO2 , the cyclohexene-1-ol disappears completely and the
other oxidized products are produced with comparable amounts:
2-cyclohexen-1-one (34.6%), cyclohexene epoxide (20.2%), cyclo-
hexanol (22%) and cyclohexanone (23.2%).
(85%), while reduced Au/ZrO2 induces (as in the case of reduced
Au/TiO2 ) selectivity toward all products with comparable amounts
[2-cyclohexen-1-one (30.4%), cyclohexene epoxide (18%), cyclo-
hexanol (30.9%) and cyclohexanone (20.7%)].
The results of activity show that gold particles behave differ-
ently, depending on the oxide used as support. Indeed, the TON
increased 3 times when switching from dried Au/TiO2 to reduced
Au/TiO2 , whereas Au/ZrO2 reduction induces a decrease of the TON.
It seems that a part of gold particles on TiO2 (probably very small
particles) need a reduction to be activated. However, on ZrO2 the
majority of gold particles are activated just after drying.
Moreover, the results let us say that selectivities depend more on
the oxidation states of gold nanoparticles than on the nature of the
oxide. Indeed, whatever the support is, dried catalysts, containing
Au3+ , Au+ and Au␦+ but not Au0 produce exclusively 2-cyclohexen-
1-one and/or cyclohexene-1-ol. However, for reduced catalysts,
which contain Au0 but not Au3+ , Au+ and Au␦+ , the reaction prod-
ucts are: 2-cyclohexen-1-one, cyclohexene epoxide, cyclohexanol
and cyclohexanone.
In order to explain how the major products are formed, we pro-
pose to see the different paths of cyclohexene oxidation according
to the literature [38,53–57].
Scheme 2 shows that the oxidation of cyclohexene begins first by
the formation of cyclohexene hydroperoxide. After the formation
of this hydroperoxide, the final oxidation may be carried out either:
(i) through the intervention of a second molecule of cyclohexene
(path I and II) or
(ii) by disintegration of the hydroperoxide (paths III and IV).
Cyclohexanol can be produced through the hydration of cyclo-
hexene (path V).

Table 2
Activity and selectivity of gold catalysts in cyclohexene oxidation. S: selectivity, C%: conversion of cyclohexene, TBHP%: conversion of TBHP.

Sample TON (10−3 ) C% TBHP % SPO % SONE % SOL % SENOL % SENONE %

Au/TiO2 dried 2.77 17.7 6.2 1 0 0 81.1 18

Au/TiO2 reduced 9.13 58.4 53.3 20.2 23.2 22 0 34.6
Au/ZrO2 dried 10.90 39.5 30.0 9 3.2 2.5 0 85.2
Au/ZrO2 reduced 7.90 28.6 34.7 18 20.7 30.9 0 30.4

Bold indicates the most important selectivities.

 N. Ameur et al. / Journal of Molecular Catalysis A: Chemical 374–375 (2013) 1–6
Scheme 2. Mechanism of cyclohexene oxidation.
Based on these reaction paths, we can say that whatever the
support is (TiO2 or ZrO2 ), Au3+ , Au+ and Au␦+ lead to the disinte-
gration of the hydroperoxide of cyclohexene (path III and IV) to
give predominantly either 2-cyclohexene-1-ol in the case of dried
Au/TiO2 or 2-cyclohexene-1-one in the case of dried Au/ZrO2 . On
the other hand, Au0 nanoparticles lead to the intervention of a
second molecule of cyclohexene (path I and II).
4. Conclusion
Au/TiO2 and Au/ZrO2 catalysts have shown high efficiency for
cyclohexene oxidation. The activity seems to depend both on
the oxidizing state of gold nanoparticles and on the nature of
the support. Au0 nanoparticles are not very selective, while Au␦+
nanoparticles are very selective towards the production of 2-
cyclohexene-1one and 2-cyclohexene-1-ol.
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