A mesoporous SnO-γ-Al2O3nanocomposite prepared by a seeding-crystallization method and its catalytic esterification performances

Article abstract of DOI:10.1039/d1nj02585f

A mesoporous SnO-γ-Al2O3 nanocomposite was synthesized by a seeding-crystallization method and investigated in catalytic esterification of pentaerythritol and stearic acid to produce pentaerythrityl tetrastearate. SnO-γ-Al2O3 prepared by conventional hydrothermal synthesis was also examined for comparison. The catalysts were studied using XRD, N2 adsorption, NH3-TPD, SEM, 27Al MAS NMR, pyridine-FTIR and CHNS analysis. According to the results of characterization, the seeding-crystallization method was helpful in reducing the size of the crystal particles, and improving the crystallinity and dispersity of crystal particles. The surface area, especially the external surface area, pore volume and size were increased, and the total acidity was increased. The strong acid sites were transformed into medium strong acid sites, and the strength of the medium strong and strong acid was weakened. Therefore, the formation of coke was retarded, and the pentaerythritol conversion, the pentaerythrityl tetrastearate selectivity and the catalytic stability were obviously improved.

Full text of DOI:10.1039/d1nj02585f

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A mesoporous SnO–c-Al2O3 nanocomposite
prepared by a seeding-crystallization method and
its catalytic esterification performances
Cite this: New J. Chem., 2021,
45, 14797
Wei Ding,†a Mingyu Cui,†a Lizhi Wang,b Wei Xu,a Yuan Wang,c Yidong Zhang,*a
a
Rong Shao*a and Jianfei Ding
*
A mesoporous SnO–g-Al2O3 nanocomposite was synthesized by a seeding-crystallization method and
investigated in catalytic esterification of pentaerythritol and stearic acid to produce pentaerythrityl
tetrastearate. SnO–g-Al2O3 prepared by conventional hydrothermal synthesis was also examined for
comparison. The catalysts were studied using XRD, N2 adsorption, NH3-TPD, SEM, 27Al MAS NMR,
pyridine-FTIR and CHNS analysis. According to the results of characterization, the seeding-crystallization
method was helpful in reducing the size of the crystal particles, and improving the crystallinity and
dispersity of crystal particles. The surface area, especially the external surface area, pore volume and size
were increased, and the total acidity was increased. The strong acid sites were transformed into medium
strong acid sites, and the strength of the medium strong and strong acid was weakened. Therefore, the
formation of coke was retarded, and the pentaerythritol conversion, the pentaerythrityl tetrastearate
selectivity and the catalytic stability were obviously improved.
Received 27th May 2021,
Accepted 13th July 2021
DOI: 10.1039/d1nj02585f
rsc.li/njc
stability, high catalytic activity, good reaction selectivity, no corro-
sion to equipment, water resistance, heat resistance and no waste
Introduction
Pentaerythrityl tetrastearate (PETS) is an important chemical water in the reaction process.4–13
material, which can be used as the raw material for producing
Among them, the metal oxide g-Al2O3 has drawn attention
compatibilizers, surfactants, rubber additives, and so on. PETS for the esterification due to its excellent catalytic activity and
is commonly used as a lubricant and release agent in engineer- outstanding stability, acting as the active component or the
ing plastics. It can greatly improve the surface gloss of the support of catalysts. Liu8 et al. reported that continuous ester-
products and is beneficial to the demoulding of the products. It ification of oleic acid and ethanol to ethyl oleate under sub/
can also be used as a dispersant for material products, which supercritical conditions over g-Al2O3 catalysts achieved a yield
can accelerate the dispersion of fillers and pigments.
over 98% at 325 1C, 200 bar and 1 min residence time. Yuan10
PETS is mainly produced by the catalytic esterification of et al. prepared a SO42À/TiO2/g-Al2O3 solid acid catalyst by
pentaerythritol and stearic acid. However, to the best of our an impregnation method during the esterification of n-butyl
knowledge, there are very few studies reported on this work. alcohol and lauric acid.
Therefore, we mainly referred to the literature of other esterifica-
SnO catalysts have also attracted the attention of many research
tion reactions and the catalysts used. Traditionally, esterification teams. Ma et al. used SnO as the catalyst during the esterification of
is catalyzed by mineral acids. However, these homogeneous acid pentaerythritol and heptanoic acid to produce pentaerythritol tetra-
catalysts are corrosive, and result in significant drawbacks on the heptanoate.14 Qian et al.15 synthesized naphthenic acid esters using
process and environmental aspects.1–3 To overcome these draw- SnO catalysts, and Jin et al.16 used SnO as the catalyst to synthesize
backs, too many kinds of solid acid catalysts are used in the trimethylolpropane palm kernel acid esters. Wang et al. used SnO as
esterification, because solid acid has the advantages of good the catalyst for the esterification of naphthenic acid and methanol.17
In these studies, SnO catalysts exhibited superior catalytic esterifica-
tion properties, however, because SnO is a powder, it is difficult for
SnO catalysts to be used directly in a fixed bed, and a long stirring
reaction can easily cause the SnO powder to become flocculent and
separation is very difficult in a continuous stirred-tank reactor.
Combining the respective advantages of SnO and g-Al2O3
catalysts, the SnO–g-Al2O3 composite may exhibit superior
a School of Chemistry and Chemical Engineering, Yancheng Institute of Technology,
Yancheng, Jiangsu, 224051, P. R. China. E-mail: ycitjfding@sina.com
b Tianjin Dagang Oilfield Natural Gas Company, Tianjin 300280, P. R. China
c School of Chemistry and Environmental Engineering, Yancheng Teachers
University, Yancheng 224002, Jiangsu, P. R. China
† These authors contributed equally to this work.
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catalytic esterification properties. Wang et al.18 prepared a SnO–g- seeding-crystallization method is conducive to the formation
Al2O3 catalyst for the esterification of naphthenic acid and methanol. of a large number of nuclei during the preparation process.
However, the SnO–g-Al2O3 catalyst was prepared by simply mixing
A NH3-TPD experiment was carried out to characterize the
SnO, g-Al2O3, Al(OH)3 and water, and then baked at 500 1C in a acidic properties of the samples, and the results are shown in
nitrogen atmosphere. The BET surface area and pore volume were Fig. 3 and Table 1. The acid strength is usually determined
small, and the interaction between SnO and g-Al2O3 was weak, which by the temperature of the ammonia desorption: weak
are important factors affecting the performance of the catalyst.
(100–200 1C), medium (200–400 1C) and strong (4400 1C).28–32
In this work, the SnO–g-Al2O3 composite is prepared by a It is obvious that there are two peaks at 200–300 1C and
seeding-crystallization method. This method is beneficial to the 500–600 1C on the C-1 and C-2 samples, which reveals the
preparation of mesoporous SnO–g-Al2O3 nanocomposite, which presence of medium and strong acid sites. The amount of strong
has the advantages of high surface area, pore volume, crystal- acid sites on C-1 are less than those on C-2, however, the amount
linity, dispersity and total acidity. The pentaerythritol conver- of medium acid sites and the total amount of acid sites on C-1 are
sion, the pentaerythrityl tetrastearate selectivity and the more than those of C-2. The temperatures of NH3-TPD on C-1 are
catalytic stability are obviously improved.
evidently lower than those of C-2, indicating the acid strength of
C-1 is weaker than that of C-2. Furthermore, the total amount of
acidity on C-1 is more than that of C-2. The key reason may be as
follows: The addition of crystal seed provides a rich induction
point for the formation of crystal nuclei in the raw material
system, leading to an increase in the number of crystal nuclei.
However, the amount of raw material in the system is a certain
value, unable to provide the raw liquid needed for the crystal
nucleus growth, so the crystal particle size becomes smaller. The
smaller particles have a larger specific surface area, which exposes
more acid sites. Combined with the characterization results of the
SEM, the crystal seed method favors the dispersion of the crystal
particles, thus affecting the acidity distribution.
Fig. 4 exhibits the pyridine-FTIR spectra of C-1 and C-2. The
characteristic vibration bands at 1538 cmÀ1 and 1445 cmÀ1 are
attributed to Brønsted acid sites and Lewis acid sites,
respectively.33 From the results of Pyridine-FTIR, we can see
that there is only Lewis acid sites on C-1 and C-2. The con-
centrations of Lewis acid sites are shown in Table 1. The
amount of Lewis acid sites on C-1 is more than that of C-2,
which is the same as the results of NH3-TPD.
Results and discussion
Catalyst characterization
XRD, SEM, NH3-TPD, Pyridine-FTIR, 27Al MAS NMR and N2
adsorption–desorption. Fig. 1 displays the XRD patterns of the
samples. For the C-1 and C-2 samples, the diffraction planes of
(001), (101), (110), (200), (112), (211), (202) and (220) are present,
which matches the standard card (JCPDS #06-0395) of the
tetragonal tin oxide.19–23 This proves that the tetragonal tin oxide
is successfully prepared by both methods. At the same time,
peaks of 38.3, 43.5 and 64.11 are observed in Fig. 1, which is
in good agreement with the characteristic peaks of the
g-Al2O3 reported in the literature.24–27 This proves that g-Al2O3 is
also successfully prepared in the C-1 and C-2 samples. Therefore,
the main components of the sample C-1 and C-2 are the tin oxide
and g-alumina (SnO–g-Al2O3) complexes. Taking the crystallinity
of C-1 (100%) as the standard, the relative crystallinity of C-2 is
calculated by comparing the sum of the characteristic peak areas
with those of C-1. As shown in Table 1, the relative crystallinity of
C-2 is 47.2%, so the crystallinity of C-1 is higher than that of C-2.
The seeding-crystallization method may improve the crystallinity
of the samples.
Fig. 5 illustrates the 27Al MAS NMR spectra of C-1 and C-2. There
are two peaks at B60 ppm and B0 ppm in the 27Al MAS NMR
spectra for both C-1 and C-2, which are attributed to tetrahedral
and octahedral Al3+ ions, respectively.27,34 In both of the 27Al MAS
NMR spectra, the peak of the tetrahedral Al species are obviously
weaker than the peak of the octahedral Al species. The relative
intensity of the 27Al MAS NMR spectrum is obtained by the
deconvolution method. It is obvious that the relative intensity of
octahedral Al follows the order of C-1 (85.7%) 4 C-2 (79.2%), which
is consistent with the variation of relative crystallinity in Table 1.
Furthermore, the relative intensity of tetrahedral Al of C-1 (14.3%)
is weaker than that of C-2 (20.8%). The relative intensity differences
of these aluminum species with different configurations may have
very important effects on the acid properties of the samples. The
peaks of the 27Al MAS NMR spectrum of C-1 shift slightly to higher
frequencies than those of C-2, which may be due to the stronger
interaction between tin oxide and alumina in the C-1 sample
prepared by the seeding-crystallization method.
SEM images of C-1 and C-2 are shown in Fig. 2. C-1 shows
better crystal particle dispersion and more uniform crystal
particle size than those of C-2. Moreover, the particle size
of C-1 is smaller than that of C-2, and the number of crystals
in C-1 is more than that of C-2, and C-1 and C-2 show different
crystal morphologies. The reason for this may be that the
The nitrogen adsorption–desorption isotherms and corres-
ponding pore size distributions of the C-1 and C-2 samples are
shown in Fig. 6(a and b), and the related textural data are shown in
Table 1. The isotherms of the samples show typical type IV features
Fig. 1 XRD patterns of C-1 and C-2.
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Table 1 Physicochemical properties and acidities of C-1 and C-2 catalysts
Surface area
À1
Lewis acid-
Relative
crystallinity
(%)
Particle
size
(nm)
[m2 gÀ1
]
Acidity [mmol NH3 gcat ]
Pore
Pore
size
[nm]
volume
ity (mmol
[cm3 gÀ1
]
Total
Medium
Strong
gcat
)
À1
Catalyst
SBET
Sext
C-1
C-2
613.8
485.7
223.1
138.2
1.1
0.4
4.8
4.4
512
495
289
208
223
287
153.15
138.37
100
47.2
32
86
Fig. 2 SEM images of C-1 and C-2.
Fig. 5 27Al MAS NMR spectra of C-1 and C-2.
Fig. 3 NH3-TPD curves of C-1 and C-2.
Fig. 6 (a) N2 adsorption isotherms and (b) pore size distributions of C-1
and C-2.
pentaerythritol conversion on C-1 is higher than that of C-2.
After seven reaction cycles (21 h), the pentaerythritol conver-
sion decreased from 99.8% to 97.0% on C-1, however, the
pentaerythritol conversion decreased from 96.5% to 90.5% on
C-2. The stability of C-1 is obviously higher than that of C-2. The
reason for this may be that the total amount of acidity on C-1 is
more than that on C-2, which is good for improving the
pentaerythritol conversion. In Table 1, the surface area, pore
volume and size of the C-1 catalyst are larger than those of C-2,
Fig. 4 Pyridine-FTIR spectra of C-1 and C-2.
and have a combination of H2 and H4-type hysteresis loops,35 which
are typical characteristics of mesoporous materials.36–38 The pore
size and volume of C-1 are obviously higher than those of C-2.
According to the results of SEM, the particle size of C-1 is remarkably
smaller than that of C-2, therefore, the surface area, especially the
external surface area of C-1 is higher than that of C-2, which may
offer highly effective active sites for the bulk reactant of pentaery-
thritol in our work.
Catalytic activity
The catalytic esterification performance comparison between
C-1 and C-2 is shown in Fig. 7. We can see that the
Fig. 7 Pentaerythritol conversion and PETS selectivity on C-1 and C-2.
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and the particle size of the C-1 catalyst is smaller than that of C-2, isopropoxide, TPAOH, ammonia water and deionized water was
and the length of pores is shorter than that of C-2, which would Al2O3:TPAOH:NH3:H2O = 1 : 0.5 : 10 : 200. A calculated amount
reduce the constraints to the mass transfer and usually improve the of aluminum isopropoxide, TPAOH, ammonia water and deio-
performance by facilitating both the access of the reactants to the nized water were mixed and stirred for 6 h at room tempera-
active sites and the diffusion of the reaction products. It is generally ture. Then the mixture was transferred into a PTFE lined
accepted that the strong acidity can easily lead to organic deep reactor, and was treated under autogenous pressure at 50 1C
cracking to carbon deposition. From the results of NH3-TPD, the for five days.
amount of strong acidity over C-1 is less than that of C-2, therefore,
Preparation of SnO–g-Al2O3: The preparation method for
the amount of coke on C-1 (1.8 wt%) is less than that of C-2 solution A was that a calculated amount of aluminum isoprop-
(3.1 wt%), and the deactivation of C-1 is slower than that of C-2. The oxide, TPAOH, ammonia water and deionized water were mixed
PETS selectivity on C-1 is remarkably higher than that of C-2. and stirred for 3 h at 30 1C. The molar ratio was the same as
Combined with the results of the NH3-TPD experiment, we spec- that of the crystal seed. The preparation method of solution B
ulate that the medium strong acid is beneficial to improve the PETS was that a calculated amount of ammonium stannate and
selectivity. The formation of carbon deposits is an important factor deionized water were mixed and stirred for 3 h at 30 1C. The
affecting selectivity. As the reaction proceeds, the resulting carbon molar ratio of ammonium Stannate and deionized water was
deposits cover some of the strong acid sites on the catalyst, there- SnO : H2O = 1 : 24. Then, solution B and crystal seed were
fore, the PETS selectivity is improved at the beginning of reaction. dripped simultaneously into solution A. The mass ratio of
The rate of selectivity increase of the C-2 catalyst is obviously higher solution A and B was 0.6, and the amount of crystal seed was
than that of C-1, and the reason for this may be that the rate of 10 wt% of the total mass of the A and B solution. The mixture
carbon production on C-2 is higher than that of C-1.
was stirred for 3 h at 60 1C, and the sol–gel was formed, which
was transferred into a PTFE lined reactor, and was treated
under autogenous pressure at 170 1C for 48 h. After hydro-
thermal treatment, the sample was separated by filtration,
washed with deionized water ten times, dried overnight at
120 1C, and calcined at 550 1C for 3 h in a nitrogen atmosphere.
The sample was represented by C-1. In this work, we also
prepared the C-2 sample, which was prepared by the same
method as that of C-1, except for the addition of the
crystal seed.
Reaction mechanism
According to the results of pyridine-FTIR, the catalytic activity
mainly relies on Lewis acid sites during the catalytic esterifica-
tion of pentaerythritol and stearic acid. According to the
literature,39–42 the reaction pathways of the catalytic esterifica-
tion of pentaerythritol and stearic acid should still follow the
well-established Fischer esterification mechanism. Therefore,
we propose the mechanism for the catalytic esterification of
pentaerythritol and stearic acid using SnO–g-Al2O3 catalysis to
be as follows: the stearic acid is adsorbed on the Lewis acid site
of the catalyst through its carbonyl carbon to form an activated
complex. Through a step involving the nucleophilic attack of
the pentaerythritol and subsequent loss of water, the formation
of the PETS finally takes place. On the C-1, the augmented
Lewis acid sites could facilitate a nucleophilic attack by pen-
taerythritol on the adsorbed stearic acid. Therefore, the cataly-
tic activity of C-1 is higher than that of C-2.
Catalyst characterization
The crystalline structure was obtained by X-ray diffraction
(XRD) using a Bruker D8 Advance X-ray diffractometer with
Cu Ka radiation (k = 0.15406 nm), operated at 40 kV and 30 mA
and scanned from 101 to 901. The relative crystallinity of the
samples was calculated by comparing the sum of characteristic
peak areas at 2y = 101–901. To investigate the sample morphol-
ogies, scanning electron microscopy (SEM) was carried out on a
Quanta 250 instrument. The specific surface area, pore size and
pore volume of the samples were obtained by nitrogen adsorp-
tion–desorption isotherm using a Micromeritics ASAP 2020
instrument. The specific surface area was calculated by the
BET method. The total pore volume was determined by N2
adsorption at a relative pressure of 0.99, and the pore diameter
was obtained from the desorption isotherm by the BJH method.
Ammonia temperature-programmed desorption (NH3-TPD)
profiles were obtained by Builder PCA-1200, and the amount
of acid sites was calculated by quantifying the desorbed NH3
from NH3-TPD. IR spectra of adsorbed pyridine (pyridine-FTIR)
were carried on a Shimadzu FTIR-8700 spectrometer, and the
amount of acid sites was determined by quantifying the peak
area of adsorbed pyridine from pyridine-FTIR. 27Al MAS NMR
analysis was performed on an Advance III HD 600 MHz instru-
Experimental
Materials
In the present synthesis, all reagents were of reagent grade and
used without further purification: aluminum isopropoxide
[Al(iPrO)3, Sinopharm Chemical Reagent Co. Ltd], tetrapropyl
ammonium hydroxide (TPAOH, 25 wt% in water, Beijing Wokai
Biotechnology Co. Ltd), ammonia water (NH3ÁH2O, 25 wt% in
water, Beijing Wokai Biotechnology Co. Ltd), ammonium stan-
nate [(NH4)4SnO3, Jiangyan Chemical Reagent Co. Ltd] and
deionized water.
Preparation of catalysts
Preparation of crystal seed: Moles of aluminum isopropoxide, ment at a spectrometer frequency of 119.2 MHz, using a Bruker
ammonia water and ammonium stannate were measured by 4.0 mm double-resonance MAS detector to acquire 48 kHz MAS
Al2O3, NH3 and SnO, respectively. The molar ratio of aluminum spectra, and the chemical shifts were referenced to solid
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(NH4)Al(SO4)2. The carbon content in the used catalyst was Project administration: R. S. and J. D. Funding acquisition:
analyzed for elemental analysis by using a CHNS analyzer Y. Z., Y. W., M. C. and J. D. All authors have read and agreed to
(Vario EL III).
the published version of the manuscript.
Catalyst evaluation
Conflicts of interest
A 100 mL three-necked flask was placed in a high-temperature
oil bath, and the stirrer rod of a motor stirrer was fixed on the
middle neck of the three-necked flask. One peripheral neck was
sealed with a glass stopper. A condenser was placed in the third
neck and its other interface was connected to a vacuum pump
connection, and the vacuum degree is 0.02 MPa. One of the
purposes of vacuum operations is to remove water, and the
other purpose is to prevent SnO from being oxidized to SnO2.
The molar ratio of pentaerythritol and stearic acid was
1 : 4.5, and the amount of catalyst was 1.0 wt% of the total
mass of pentaerythritol and stearic acid. The esterification
reaction was conducted at 100 1C for 3 h during a reaction
cycle. After the reaction, heating was terminated and stirring
was continued until the system cooled to room temperature.
After breaking the vacuum, the reaction mixture was filtered.
The filtrate was stood for one hour, and then the upper liquid
layer was analyzed by a SP 6890 gas chromatograph equipped
with a flame ionization detector and stainless-steel column
(10%SE-30 + 102 silanized support, 3 m  3 mm). Pentaery-
thritol conversion and product selectivity were quantified as
follows:
There are no conflicts to declare.
Acknowledgements
We are grateful for the financial support from the Natural
Science Research of Jiangsu Higher Education Institutions of
China (No. 20KJB530007 and No. 20KJB530012), the Funding
for school-level research projects of Yancheng Institute of
Technology (xjr2019012), Jiangsu Hualun Chemical Co., Ltd.
and the project of scientific research innovation for graduate
students in Jiangsu Province.
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and compared the catalytic behavior with the SnO–g-Al2O3
prepared by conventional hydrothermal synthesis in the catalytic
esterification of pentaerythritol and stearic acid to produce pen-
taerythrityl tetrastearate. The seeding-crystallization method was
helpful in reducing the size of the crystal particles and improving
the crystallinity. The surface area, especially external surface area,
pore volume and size were increased, and the total acidity was
increased. The strong acid sites were transformed into the medium
strong acid sites. Therefore, the formation of coke was retarded,
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