The Open Catalysis Journal, 2011, 4, 83-87 83

Open Access
Selective Gas-Phase Conversion of Glycerol to Acetol Over Promoted
Zirconia Solid Acid Catalysts
Gangadhara Raju, Padigapati S. Reddy and Benjaram M. Reddy*

Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Uppal Road, Hyderabad - 500
607, India

Abstract: The vapour phase selective conversion of glycerol to acetol at normal atmospheric pressure in a fixed-bed
micro reactor was investigated over SO42
and WOx promoted ZrO2 and M-ZrO2 (M = Al2O3 or TiO2) solid acid catalysts.
The investigated sulfate and tungstate ion promoted zirconia-based catalysts were prepared by both coprecipitation and
impregnation methods and calcined at 923 K. The synthesized catalysts were characterized by means of X-ray powder
diffraction, X-ray photoelectron spectroscopy, BET surface area and ammonia temperature-programmed desorption
methods. Characterization results suggest that SO42
promoter strongly influences the physicochemical properties of the
support oxides than WOx. However, the WOx promoted catalysts exhibited better catalytic activity than SO42
promoted
catalysts. Among various catalysts investigated, the WOx/Al2O3-ZrO2 catalyst exhibited stable catalytic activity with the
highest glycerol conversion of 99% and acetol selectivity of 74%.
Keywords: Glycerol, acetol, acrolein, promoted zirconia.

INTRODUCTION The selective gas-phase conversion of glycerol to acetol

has received adequate attention. Acetol could be used in a
Presently, petroleum is the foremost energy source in the
wide range of applications, including as a raw material for
world, but its shortage has led to renewed interest in
cigarette filters, in packaging, plastics, agriculture,
alternative sources of chemical feedstock and fuel. Biomass pharmaceutical products and consumer goods. On the other
is a renewable and clean energy source, and its derived fuels
hand, 1,2-propanediol is produced by hydrogenation of
are attractive alternatives to the fossil fuels, as well as source
acetol [15]. However, there are only few studies on the
for variety of chemical intermediates [1]. Biomass also has
conversion of glycerol to acetol [16-18]. Chiu et al. reported
conventional applications in industrial area, primarily for
gas-phase conversion of glycerol to acetol in a semi-batch
production of biodiesel. In the biodiesel production glycerol
reactor at high pressures and temperature by reactive
is the principal byproduct; around 10 Kg of glycerol is distillation method [16, 18]. Therefore, there is tremendous
created for every 100 Kg of produced biodiesel.
interest to selectively convert glycerol to acetol under mild
Furthermore, with the growth of the biodiesel industry, there
and most economical conditions. The present investigation
is more glycerol than that current market can easily absorb.
was undertaken taking into account the aforesaid
Besides, glycerol has a multitude of uses in the food,
background, evaluating SO42- and WOx promoted ZrO2 and
pharmaceutical and chemical industries, among others [2].
M-ZrO2 (M = Al2O3 or TiO2) solid acid catalysts for the gas-
Therefore, the effective utilization of glycerol enlarges the phase conversion of glycerol to acetol at normal atmospheric
economy of the whole biodiesel production process, and the
pressure.
conversion of glycerol to value added chemicals could be in
agreement with the perception of green chemistry in terms of MATERIALS AND METHODOLOGY
exploitation of renewable resources [3-6]. Moreover,
Catalyst Preparation
glycerol is a biodegradable, recyclable and non-toxic liquid,
highly stable under typical storage conditions and amenable ZrO2 was obtained by coprecipitation technique in
to many chemicals [7, 8]. In this manner, glycerol from accordance to the described method elsewhere [19]. The
renewable resources is considered to be an attractive and ZrOCl2 aqueous solution was dropped into a flask with
highly functionalized molecule for sustainable upcoming constant stirring and the pH value was maintained at about 8
production of value-added chemicals like propanediols, with dilute NH4OH. The obtained precipitate was carefully
acrolein, polyglycerol and so on, which are employed in the washed with distilled water until free from chloride ions and
production of variety of compounds such as polymers, dried at 393 K for 48 h. The M-ZrO2 (M = Al2O3 or TiO2)
cosmetics, plastics and detergents [9-14]. mixed oxide (1:1 mole ratio based on oxides) was prepared
by coprecipitation method. For the preparation of Al2O3-
ZrO2, an aqueous solution containing the requisite quantities
*Address correspondence to this author at the Inorganic and Physical of Zr(NO3)4·xH2O and Al(NO3)3·xH2O were prepared
Chemistry Division, Indian Institute of Chemical Technology, Uppal Road, separately and mixed together (pH 2). This solution was
Hyderabad - 500 607, India; Tel: +91-40-27191714; Fax: +91-40-27160921; hydrolyzed with dilute ammonium hydroxide with vigorous
E-mails: bmreddy@iict.res.in; mreddyb@yahoo.com stirring until the pH of the solution reached to 8-9. At this
pH, a white precipitate was formed and the precipitate was

1876-214X/11 2011 Bentham Open

84 The Open Catalysis Journal, 2011, Volume 4 Raju et al.

allowed to settle for 2 days. The resulting precipitate was the catalyst samples was corrected by setting the binding
filtered off and washed several times with deionized water energy of the adventitious carbon (C 1s) at 284.6 eV. The
and dried at 393 K for 12 h. For the preparation of TiO2 - XPS analysis was done at room temperature and at pressures
ZrO2, an aqueous solution containing the requisite quantities typically in the order of less than 10
6 Pa. Catalysts were
of TiCl4, ZrOCl2, and urea were heated together to 368 K outgassed in a vacuum oven overnight before XPS
with vigorous stirring. In about 6 h of heating, as measurements.
decomposition of urea progressed to a certain extent, the pH
of the solution increased from 2 to more than 7 and the Activity Measurements
formation of precipitate gradually occurred. The precipitate The gas-phase conversion of glycerol to acetol was
was heated for 6 h more to facilitate aging. The resulting conducted at 588 K under normal atmospheric pressure in a
precipitate was filtered off, washed several times with down-flow fixed-bed glass reactor (9 mm i.d.) using 0.5 g of
deionized water until free from chloride ions, and dried at catalyst. Before the reaction, the catalyst was pretreated at
393 K for 12 h. A portion of the oven-dried material was 673 K for 2 h in a flowing dry N2 (30 mL/min). The reactant
calcined at 1073 K for 5 h in air atmosphere and stored in containing an aqueous solution of 20 wt.% glycerol in water
dry nitrogen atmosphere. The WOx/ZrO2 catalyst was was first evaporated in a preheater and then entered the
prepared by a wet impregnation method. To impregnate reactor in down flow mode at a flow rate of 1 ml/hr. The
tungsten-oxide promoter (15 wt.%), the desired quantity of reaction products were condensed in a dry ice trap and
ammonium metatungstate was dissolved in excess water collected hourly for analysis by GC equipped with ZB Wax
separately and to which the powdered Zr(OH)4 was added. capillary column and a flame ionization detector.
The WOx/M-ZrO2 (M = Al2O3 or TiO2) catalyst containing
15 wt.% WOx was prepared by a suspension impregnation RESULTS AND DISCUSSION
method. To incorporate tungsten oxide, the requisite Catalyst Characterization
quantities of ammonium metatungstate was dissolved in
excess water and the finely powdered oven-dried anhydrous Fig. (1A) shows the XRD patterns of WTZ, WAZ and
M-ZrO2 support was added to this solution and refluxed at WZ catalysts. In the XRD patterns of the WTZ catalyst, the
383 K for 2 h. To prepare SO42
/ZrO2, a 0.5 M sulfuric acid characteristic peaks (#) corresponding to crystalline ZrTiO4
solution (30 ml) was poured into the finely powdered [21] are observed. The XRD lines only due to tetragonal
Zr(OH)4. To prepare SO42
/M-ZrO2 (M = Al2O3 or TiO2), the zirconia phase are observed in the case of WAZ catalyst,
oven-dried anhydrous M-ZrO2 was immersed in 1 M H2SO 4 while both tetragonal and monoclinic zirconia phases were
solution (30 ml) for 30 min to incorporate sulfate ions. The observed in the case of WZ catalyst [19, 20]. Fig. (1B)
excess water was evaporated on a water bath. The resulting shows the XRD patterns of STZ, SAZ and SZ catalysts. The
samples were oven-dried at 383 K for 12 h and calcined at STZ catalyst shows characteristic peaks corresponding to
923 K for 5 h in air atmosphere [19-21]. The investigated ZrTiO4 (#) and Ti2(SO4)3 () [21]. In the case of SAZ
WOx/ZrO2, WOx/TiO2-ZrO2, WOx/Al2O3-ZrO2, SO42
/ZrO2, catalyst only tetragonal zirconia phase is observed [20],
SO42
/TiO2-ZrO2 and SO42
/Al2O3-ZrO2 catalysts are referred while a combination of tetragonal and monoclinic zirconia
as WZ, WTZ, WAZ, SZ, STZ and SAZ, respectively. phases are observed in the case of SZ catalyst [19]. From
both Fig. (1A, B) it can be noted that there are no peaks due
Catalyst Characterization to the corresponding supports, alumina and titania. This
X-ray powder diffraction patterns have been recorded on observation suggests that alumina and titania are
a Siemens D-5000 instrument by using a Cu K radiation homogeneously mixed with the zirconia and are acting as
source and a scintillation counter detector. The specific structural stabilizers for zirconia [20, 21].
surface areas of the catalysts were determined on a Table 1 shows the BET surface area and ammonia-TPD
Micromeritics Gemini 2360 instrument by N2 physisorption results of various samples. It can be noted from this table
at liquid nitrogen temperature. Before measurements, all the that the specific surface area of SZ and STZ catalysts was
catalysts were dried in situ at 473 K for 2 h under vacuum. higher than WZ and WTZ catalysts, however the specific
The temperature-programmed desorption (TPD) measure- surface area of SAZ catalyst was less than WAZ catalyst (SZ
ments were performed on an AutoChem 2910 instrument > WZ, STZ > WTZ and SAZ < WAZ). This may be due to
(Micromeritics, USA). A thermal conductivity detector was the formation of nonporous sulfates of Al and Zr in the SAZ
used for continuous monitoring of the desorbed ammonia catalyst. The less specific surface area of WZ and WTZ
and the areas under the peaks were integrated. Prior to TPD catalysts may be due to the penetration of the W-oxide into
measurements, catalysts were pretreated at 473 K for 1 h in a the zirconia pores [19]. It can be observed from the
flow of ultra pure helium gas (50 ml min
1). After ammonia-TPD results that all the samples show two types of
pretreatment, the sample was saturated with 10% ultra pure acid sites in two different regions [19, 20, 22]. The SO42

anhydrous ammonia gas (balance He, 75 ml min
1) at 353 K promoted catalysts exhibit more number of strong acidic
for 2 h and subsequently flushed with He (60 ml min
1) at sites, less number of moderate and weak acidic sites when
383 K for 1 h to remove the physisorbed ammonia. The compared to that of WOx promoted catalysts [23]. The total
heating rate for the TPD measurements, from 383 to 1073 K, amount of ammonia desorbed in the case of SAZ and STZ
was 10 K min
1. The XPS measurements were made on a catalysts was found to be less than that of WAZ and WTZ
Shimadzu (ESCA 3400) spectrometer by using Mg K catalysts. Where as in the case of SZ and WZ catalysts, the
(1253.6 eV) radiation as the excitation source. Charging of amount of ammonia desorbed was higher for the SZ catalyst
than the WZ.
Selective Conversion of Glycerol to Acetol The Open Catalysis Journal, 2011, Volume 4 85

Table 1. BET Surface Area, Total Acidity and Zr Electron

Binding Energies (eV) of Various Promoted Zirconia
Catalysts

BET Total NH3 Binding Energies (eV)

S. No. Catalyst Surface Desorbed
Area (mmol/g) Zr 3d5/2 Zr 3d3/2
(m2 /g)

1 WZ 64 0.39 182.9 185.2

2 WTZ 14 0.71 183.1 185.4
3 WAZ 114 0.83 182.9 185.2
4 SZ 100 0.69 182.9 185.2
5 STZ 28 0.64 183.1 185.5
6 SAZ 33 0.65 183.0 185.3

of ZrTiO4 compound in the case of WTZ catalyst as

observed from XRD results. Fig. (2B) shows the Zr 3d
photoelectron peaks of SO42
promoted catalysts. It can be
observed that the XPS peaks at 183.0 and 185.3 eV are
corresponding to Zr 3d5/2 and Zr 3d3/2, respectively [24]. A
slight shift towards higher binding energy is observed in the
case of STZ catalyst, which is mainly due to the formation of
ZrTiO4 compound as noted from XRD analysis. However, a
slight broadening and decrease in the intensity of the lines is
noted in the case of SAZ catalyst. Interestingly, a slight shift
towards higher binding energy and a significant broadening
is noted in the case of SO42
promoted catalyst. These results
reveal that the sulfate ion has exhibited a strong influence on
the intensity and binding energy of the Zr 3d lines.
Catalytic Experiments
The gas phase conversion of glycerol reaction is shown
in Scheme 1. The possible major products in this reaction are
acetol and acrolein. Acetol can be produced by the mono
dehydration of glycerol, where as acrolein is produced by
double dehydration of glycerol. Fig. (3) shows the glycerol
conversion and the selectivity towards acrolein and acetol
over promoted zirconia catalysts at 588 K during 3 h of
catalytic run. It was noted that all catalysts exhibit excellent
catalytic activity. The glycerol conversion and selectivity
towards acetol in the case of WOx promoted catalysts is
higher than that of the SO42
promoted catalysts. This may be
due to the formation of strong acidic sites in the case of
SO42
promoted catalysts which are prone to fast
deactivation. But the selectivity towards acrolein is slightly
higher in the case of SO42
promoted catalysts, because these
catalysts possessed large number of strong acidic sites as
Fig. (1). X-ray powder diffraction patterns of (1A) WZ, WTZ and confirmed from the ammonia-TPD results which favour
WAZ, and (1B) SZ, STZ and SAZ catalysts. (#) ZrTiO4; (O) increase in the selectivity of acrolein [25]. Among all
tetragonal ZrO2; (*) monoclinic ZrO2. ()Ti2 (SO4)3. catalysts, the WAZ catalyst exhibited the highest glycerol
Fig. (2A) shows the Zr 3d photoelectron peaks of conversion of ~99% and the selectivity towards acetol of
tungsten-oxide promoted catalysts. It can be observed that ~74%.
the Zr 3d lines are reasonably well resolved with good Fig. (4) shows the time-on-stream activity studies over
intensity. The XPS peaks at 182.9 and 185.2 eV are various catalysts at a reaction temperature of 588 K. The
corresponding to Zr 3d5/2 and Zr 3d3/2, respectively [24]. It is WOx promoted catalysts exhibited better activity than the
observed that a slight shift towards higher binding energy is SO42
promoted catalysts. It is interesting to note that
noted in the case of WTZ catalyst when compared to that of initially the glycerol conversion was high over all catalysts.
WAZ and WZ catalysts. This is mainly due to the formation However, the glycerol conversion was observed to decrease
86 The Open Catalysis Journal, 2011, Volume 4 Raju et al.

The large amount of strong acidic sites on the catalyst

2A surface facilitate acrolein product through the formation of
Zr 3d5/2
an intermediate, 3-hydroxypropanal, which is unstable at
Zr 3d3/2 reaction conditions [25, 27]. Thus, for higher selectivity of
acetol moderate strength acidic sites are required.
Intensity (a.u)

WAZ
100

Conversion/Selectivity (%)
80
WTZ

60
WZ
40

178 180 182 184 186 188 190

Binding energy (eV) 20

0
WZ WTZ WAZ SZ STZ SAZ
Catalyst

Fig. (3). Gas-phase conversion of glycerol to acetol over WZ,

2B WTZ, WAZ, SZ, STZ and SAZ catalysts. Reaction conditions:
Zr 3d5/2 catalyst amount = 0.5 g; reaction temperature = 588 K; reaction
Zr 3d3/2
time = 3 h. ( ) glycerol conversion; ( ) selectivity to acetol;
SAZ ( ) selectivity to acrolein; ( ) other byproducts#. #
acetaldehyde, acetic acid, acetone, propanal, ethanol, methanol, and
some unidentified products.
Intensity (a.u)

100
STZ
90
Glycerol Conversion (%)

80
SZ
70 WAZ
WTZ
60 WZ
178 180 182 184 186 188 190 SZ
Binding energy (eV) 50 STZ
SAZ

Fig. (2). The Zr 3d XPS spectra of (2A) WZ, WTZ andd WAZ, and 40
(2B) SZ, STZ and SAZ catalysts.
30
with time in the case of SO42
promoted catalysts, while in
the case of WOx promoted catalysts a slight decrease is 1 2 3 4 5 6
noted. This is probably due to deactivation of SO42

promoted catalysts. Reason for the deactivation of SO42
Time (h)
promoted catalysts could be due to catalyst coking and/or
formation of sulfuric acid at the reaction temperature (since Fig. (4). The conversion of glycerol over WZ, WTZ, WAZ, SZ,
reactant contains water), which lead to downstream STZ and SAZ catalysts is shown as a function of time-on-stream.
contamination also [26]. Fig. (5) shows the results of time- Reaction conditions: catalyst amount = 0.5 g; reaction temperature
on-stream selectivity of acetol over various catalysts at 588 = 588 K.
K for 6 h. The selectivity of acetol increased with the CONCLUSION
reaction time up to 3 h reaction. After 3 h of reaction the
selectivity is slightly decreased. Among all catalysts, the SO42
and WOx promoted ZrO2 and M-ZrO2 (M = Al2O3
WAZ catalyst showed high selectivity and decreased in the or TiO2) solid acid catalysts were successfully prepared by
order of WAZ > WZ > WTZ > SZ > SAZ > STZ. These coprecipitation and impregnation methods for vapour phase
results reveal that the WOx promoted catalysts exhibit high conversion of glycerol to acetol. It was found that the SO42

selectivity towards acetol probably due to optimum acidity. promoter strongly influences the physicochemical properties
Selective Conversion of Glycerol to Acetol The Open Catalysis Journal, 2011, Volume 4 87

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the WAZ catalyst exhibited high surface area and more NH3 Dehydration of glycerol to acetol via catalytic reactive distillation.
desorbed amount (mmol/g). The WAZ catalyst showed stable AIChE J., 2006, 52, 3543-3548.
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Enhancement of glycerol conversion to acetol in high-temperature
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ACKNOWLEDGMENTS acetol. AIChE J., 2008, 54, 2456-2463.
[19] Reddy, B.M.; Sreekanth, P.M.; Reddy, V.R. Modified zirconia
G.R. and P.S.R. thank Council of Scientific and solid acid catalysts for organic synthesis and transformations. J.
Industrial Research, New Delhi, for the award of Senior Mol. Catal. A Chem., 2005, 225, 71-78.
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Received: October 13, 2010 Revised: November 11, 2010 Accepted: December 29, 2010

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