Uamerica 23 118752
Uamerica 23 118752
Uamerica 23 118752
A R T I C L E I N F O A B S T R A C T
Keywords: Metal-dopant modification is a promising approach to enhance the catalytic performance of titanium silicate
Oxidative hydration of ethylene molecular sieve. Herein, titanium silicalite-1 (TS-1) with different titanium contents and a series of metal-doping
Metal-doping modification modified TS-1 are prepared, to enhance the synthesis of ethylene glycol (EG) through oxidative hydration of
Titanium silicalite-1
ethylene. The EG selectivity show a volcano relationship along with the increase of Ni addition, and reach
Ethylene glycol
Promoter mechanism
maximum in 80.63 % at 0.13 wt % Ni loading. The Ni promoter mechanism is revealed that NiO species enhances
the electropositivity of skeleton Ti and neutralizes the surface acidity of TS-1, which improves the efficient
utilization of H2O2 and selectivity of EG. Furthermore, Ni-modified TS-1 shows superior stability to TS-1, as well
as satisfactory reusability since the deactivation of catalyst is reversible through high-temperature calcination.
This work demonstrates the feasibility and mechanism of Ni promoter and provides a promising strategy for the
development of TS-1 catalysts.
* Corresponding authors.
E-mail addresses: [email protected] (J. Zhu), [email protected] (H. Xu).
https://doi.org/10.1016/j.apcata.2022.118752
Received 8 April 2022; Received in revised form 21 June 2022; Accepted 24 June 2022
Available online 28 June 2022
0926-860X/© 2022 Elsevier B.V. All rights reserved.
F. Cheng et al. Applied Catalysis A, General 643 (2022) 118752
with Ti active sites of titanium silicalite. For example, when fluorine [23, existence forms of Ti were observed by UV–visible spectroscopy on a UV-
24], SiO3/2F units was introduced into the zeolite framework to increase 3600i Plus spectrophotometer with a wavelength range of 185–800 nm.
the electropositivity of the tetrahedral Ti active sites, it significantly The Fourier transform infrared spectroscopy (FTIR) was recorded on a
enhanced the catalytic activity in the epoxidation of ethylene with H2O2. Perkin Elmer Frontier spectrometer with the frequency range of
In addition, the numbers and strength of acid sites of TS-1 were 4000–400 cm− 1. The intensity and amounts of acid on the catalyst
enhanced by the incorporation of trivalent ions (Al3+, B3+, or Fe3+) [25]. sample surface were analyzed through NH3-Temperature Programed
Unfortunately, the increase of acid amount greatly reduces the selec Desorption (NH3-TPD) on a AutoChem1 II 2920 temperature-
tivity of EG. In recent years, transition metals, such as Ni, Cu, Cr, Co, programmed chemisorption instrument. The specific surface area and
etc., have been demonstrated to effectively improve the performance of pore structure of the TS-1 were analyzed by adsorption-desorption iso
TS-1 catalysts in the reaction of epoxidation of propylene, epoxidation of therms collected at a Quadrasorb SI automatic specific surface and
butadiene, et al. [26–30]. Therefore, as for direct synthesis of EG from porosity analyzer. The calculation of the specific surface area and pore
ethylene and H2O2 over titanosilicates, metal-doping modification may size distribution models was obtained by the Brunauer-Emmett-Teller
be a desirable strategy to improve catalytic performance. (BET) equation and the Density functional theory (DFT) model,
In this work, with the optimal titanium content, we prepared a series respectively. The accurate content of each metal element in each sample
of metal-doping modified TS-1 molecular sieves by excess impregnation was obtained by ICP-OES on Agilent 5110. The bonding structures and
method. By fixing Ti/Si and adjusting the loading of Ni to regulate the surface electronic states of samples were obtained with X-ray photo
surface acidity of TS-1 zeolite and electropositivity of framework tita electron spectroscopic (XPS) experiments performed on a Thermo K-
nium, the Ni-amount-dependent-EG selectivity in the oxidative hydra Alpha with Al Kα radiation.
tion of ethylene was explored. The crystal phase, microstructure and
pore structure distribution of TS-1 molecular sieves catalysts were 2.3. Catalytic performance evaluation
characterized by X-ray diffraction (XRD), scanning electron microscope
(SEM), N2 physical adsorption, etc. Combined with temperature pro The ethylene oxidation hydration reaction was carried out in a
grammed desorption of NH3 (NH3-TPD) and X-ray photoelectron spec stainless steel autoclave lined with PTFE which volume was 100 mL.
troscopy (XPS), we analyzed the promotion mechanism of Ni species on When evaluated the catalytic performance of TS-1 or M-TS-1 in the
the catalytic selectivity and service life of Ni-TS-1. Further, the deacti oxidation hydration reaction of ethylene, a mixture of catalyst (0.25 g)
vation reasons and regeneration methods of catalysts were explored in and deionized water (10 mL) was fed into the reactor. Afterwards, ni
detail. trogen was charged into the reactor to check the air tightness of the
device and then ethylene was charged into the reactor to replace the
2. Experimental nitrogen inside three times and kept the C2H4 pressure constant at 2.0
MPa at room temperature⋅H2O2 (4 wt %) was added to the airtight
2.1. Catalyst preparation reactor through a metering pump at the rate of 0.4 mL/min for 1 h,
continued to react for 1 h, the temperature of the whole process was 353
According to the method in the literature [31], TS-1 with different K. The reactions were terminated by circulating cold water bath, and
Ti/Si were synthesized by hydrothermal crystallization method, then opened the reactor after releasing the pressure slowly. The liquid
wherein tetraethyl orthosilicate and tetrabutyl titanate were used as raw products were separated from the reaction mixture by needle tube filter.
materials, and tetrapropyl ammonium hydroxide (TPAOH) was used as The content of unconverted H2O2 was determined by a potentiometric
structure directing agent. The titanium silica sol precursor solution with titration method using 0.03 M Ce(SO4)2 solution in an potentiometric
molar compositions of 1.0 SiO2: x TiO2 (x = 0.01–0.05): 0.18 TPAOH: titrator. Liquid products was qualitatively and quantitatively analyzed
18 H2O were crystallized at 448 K and autogenous pressure for 72 h in a by gas chromatography (Varian, FID detector) with the external stan
teflon-lined crystallization autoclave. The synthesized TS-1 zeolites dard method.
were centrifuged and fully washed with water and ethanol. Then dried The products contain ethylene oxide, ethylene glycol, diethylene
at 120 ℃ for 10 h, and roasted at 550 ℃ for 6 h to remove moisture and glycol and triethylene glycol, etc. The conversion of H2O2 and selectivity
TPAOH to obtain the resultant product (denoted as TS-1–0.01、0.02、 of ethylene glycol (EG) and diethylene glycol (DEG) were calculated as
0.03、0.04、0.05, respectively). follows:
The metal modified TS-1 were prepared through the impregnation
Nbegin of H2 O2 - Nend of H2 O2
method. The specific modification steps are as follows. Firstly, prepared H2 O2 Conversion = × 100%
Nbegin of H2 O2
0.05 M nitrate aqueous solution of each metal (Ni、Cr、Zn、W). Then,
metal modification of TS-1 was performed with a solid-to-liquid weight (1)
ratio of 1 (TS-1): 20 (modification solution) at 60 ℃ for 3 h, and stood
N of EG
aging at room temperature overnight. The solid-liquid mixture after EG Selectivity = × 100% (2)
Nbegin of H2 O2 - Nend of H2 O2
aging was filtered, then dried at 120 ℃ for 8 h, and roasted at 550 ℃ for
4 h to obtain the M-TS-1 (M is Ni, Cr, Zn, W). In addition, in order to 2 N of DEG
discuss the influence of the concentration of the Ni modified solution on DEG Selectivity =
Nbegin of H2 O2 - Nend of H2 O2
× 100%
the catalytic performance of TS-1, change the concentration of the
(3)
modified solution to 0.01, 0.05 and 0.10, other treatment conditions
remain unchanged, the synthesized catalysts were named as Ni-TS- N of EG
1–1、Ni-TS-1–5 and Ni-TS-1–10, respectively. EG Selectivity(L) = × 100% (4)
N of Liquid product
2
F. Cheng et al. Applied Catalysis A, General 643 (2022) 118752
210 nm and 260 nm were ascribed to the Ti(IV) species in the skeleton
3. Results and discussion and amorphous Ti(V/VI) species outside the skeleton, respectively[35,
36]. With the increase of titanium content, the peak of the skeleton ti
3.1. Ti content effect on TS-1 tanium has no significant change, while the absorption peak near the
330 nm ascribed to the anatase TiO2[36] become larger from TS-1–0.01
The TS-1 catalysts with various Ti contents were synthesized and to TS-1–0.05, which is consistent with XRD results. As shown in Fig. 2d,
their microstructure were monitored by SEM (Fig. 1). It can be observed only one NH3 desorption peak at about 398 K were observed for TS-1.
that TS-1 samples with different Ti/Si were all ellipsoidal and the sizes of Obviously, the introduction of Ti into the pure silica system does not
the TS-1 were in the range of 200–500 nm. With the addition of tita result in strong acid sites[37]. As the Ti increases, the intensity of the
nium, the lattice expansion leads to the increase of particle size from peak increase significantly, indicating the increasing acidity of the sur
257 nm of TS-1–0.01–471 nm of TS-1–0.05, and the non-skeleton tita face site of samples.
nium adheres to the surface of the molecular sieve, resulting in the The results of ICP-OES for the TS-1 catalysts are shown in Table 1,
decrease of crystallinity and uneven grain size. and the actual Ti/Si of the prepared samples account for about 90 % of
Fig. 2a shows the XRD spectra of TS-1 with different titanium con the feed Ti/Si during the synthesis process. Table 1 and Fig. S1 show the
tents. The results indicate that all samples have characteristic diffraction BET surface area, pore volume, N2 adsorption-desorption isotherms and
peaks at 2θ = 7.8◦ (011), 8.8◦ (020), 23.2◦ (332), 23.8◦ (511), and 24.3◦ pore size distribution of TS-1 with different Ti contents. With the in
(313) [32], representing that the topological structure of TS-1 is MFI crease of Ti/Si, the specific surface area and pore volume of the zeolite
configuration and multidirectional growth trend. With the increasing of decrease. This may be due to the aggregation of non-skeleton titanium
Ti/Si during the synthesis process, the relative crystallinity of molecular blocking the pores. In addition, hysteresis loop belonging to slit-like
sieve sample decreases. The single diffraction peak at 29.3◦ confirms pore structure appears in the high pressure region of the N2
that Ti4+ successfully replaces Si4+ and inserted into the MFI skeleton. adsorption-desorption isotherms of TS-1–0.04, 0.05, representing the
Furthermore, no diffraction peaks emerges at 25.3◦ when titanium formation of a few mesopores.
content is low, suggesting that the anatase TiO2 does not exist in the TS-1 TS-1 catalysts with different Ti contents were evaluated in the
with low Ti-content. However, diffraction peak of anatase TiO2 en oxidative hydration of ethylene with H2O2, and the results are displayed
hances gradually as the titanium content increases. in Fig. 3. Pure-silica zeolite has no catalytic effect on the oxidative hy
The FTIR spectra of TS-1 are exhibited in Fig. 2b. The absorption dration of ethylene, where the conversion of H2O2 is only 5.6 %, and no
peak of 960 cm− 1 is the asymmetric vibration absorption peak caused by EG is found in the product, indicating that H2O2 consumption only
the interaction between titanium atoms entering the framework and the proceed in thermal decomposition reaction. The increase skeleton tita
adjacent Si-O bond[33]. The peak strength represents the relative con nium in TS-1 leads to the increase of active sites and accordingly the rise
tent of titanium in the skeleton. The peak strength of 960 cm− 1 reaches of reactivity. So the conversion rate of H2O2 improves from 83.11 % on
its peak when the Ti/Si is above 0.03, which can be demonstrated by the TS-1–0.01–96.79 % on TS-1–0.05. However, with an increase of Ti
I960/I550[34] in Table S1. However, the existence form of titanium in the content, the selectivity of EG decreases from 72.98 % on TS-
molecular sieve framework can not be accurately obtained from the 1–0.01–60.79 % on TS-1–0.05, while the selectivity of by-product DEG
FTIR or XRD spectra. In order to further characterize the existence form increases. According to the characterization results, this is mainly
of Ti in the molecular sieve sample, the samples were characterized by because excessive titanium elements formed amorphous non-framework
DRUV–vis. In the UV–visible spectra (Fig. 2c), the absorption peaks at
Fig. 1. SEM images of and particle size distribution TS-1–0.01 (a), TS-1–0.02 (b), TS-1–0.03 (c,f), TS-1–0.04 (d) and TS-1–0.05 (e). *The scale of (a-e) is 400 nm and
that of (f) is 100 nm.
3
F. Cheng et al. Applied Catalysis A, General 643 (2022) 118752
Fig. 2. The XRD patterns (a), FTIR spectra (b), UV–visible spectra (c) and NH3-TPD curves (d) of TS-1 with different titanium content.
4
F. Cheng et al. Applied Catalysis A, General 643 (2022) 118752
Fig. 3. Catalytic performance for oxidative hydration of ethylene over TS-1 molecular sieves with different titanium contents. *Reaction conditions of TS-1 with
different Ti content: 353 K, 20 bar, 2 h, H2O2 1.6 M, cat. 0.25 g.
Fig. 4. (a, b) Catalytic performance of oxidative hydration of ethylene over TS-1 and M-TS-1. (c, d) Catalytic performance of oxidative hydration of ethylene over Ni-
TS-1-x (Ti/Si=0.03, x = 1, 5, 10), Blank 1 (Ti/Si=0.01, Ni-loading is consistent with Ni-TS-1–5) and Blank 2 (Ti/Si=0.00, Ni-loading is consistent with Ni-TS-1–5).
*Reaction conditions of TS-1 and M-TS-1: 353 K, 20 bar, 2 h, H2O2 1.6 M, cat. 0.25 g.
with other metal, Ni species is more conducive to reducing the surface reactions, so Ni-TS-1 has a higher EG selectivity. As shown in XPS energy
acidity of TS-1 (Fig. 5b and Fig. S3). The decrease of acidity can effec spectrum Fig. 5c, Ni addition in TS-1 existed in the form of NiO. As for
tively avoid excessive polymerization, oxidation and other side Fig. 5d, the binding energy peak of Ti 2p3/2 in TS-1 could be
5
F. Cheng et al. Applied Catalysis A, General 643 (2022) 118752
Fig. 5. (a) XRD patterns and (b) NH3-TPD curves of Ni-TS-1-x (x = 1, 5, 10), (c) XPS Ni 2p spectra of Ni-TS-1–5 and (d) Ti 2p spectra of TS-1 and M-TS-1–5 (M=Ni,
Cr, Zn, W), (e-g) EDS mapping images (O red, Si green, Ti yellow and Ni purple) and HAADF-STEM of Ni-TS-1–5.
decomposed into two components[39], including 459.09 eV and The morphology and distribution of Ni species of the Ni-TS-1–5 were
460.39 eV assigned to anatase TiO2 and framework Ti(Ⅳ) species, examined with TEM (Fig. 5e-g) and SEM (Fig. S4). Obviously, the shape
respectively. Compared with other metal doped TS-1, the binding en of Ni-TS-1–5 samples had no obvious change after treatment with Ni
ergy of framework Ti(Ⅳ) at Ni-TS-1–5 possesses a more obviously loading, which were uniform elliptical particles. Only a little nano-scale
decrease (0.52 eV), from 460.39 eV to 459.87 eV. It suggests Ni dopant thin film was dotted on the surface of Ni-TS-1–5 molecular sieve. TEM
makes more electron cloud migration away from Ti 2p orbital, and analysis found that the Ni species in the Ni-TS-1–5 sample are anchored
accordingly reduces the density of the electron cloud around the evenly over the TS-1 hosts[41]. The statistical measurements on NiO
framework Ti[28,39,40], which enhances the electropositivity of Ti nanoparticles displayed that size distribution of these NiO nanoparticles
center and may restrain the conversion of electrophilic oxidant H2O2. are in the range of 2–14 nm with average diameter of 7 nm.
The decrease of catalytic activity in H2O2 conversion on some of Ti The specific surface area, pore volume and pore size of the Ni-TS-1-x
center (Fig. 4c, Blank1) is beneficial to reduce the local concentration of samples were measured by the nitrogen adsorption test, as shown in
EG, which hinders the occurrence of side reactions to improve the effi Fig. S5 and Table 2. The N2 adsorption isotherm showed that all samples
cient utilization of H2O2 and selectivity of EG over TS-1. still exhibit a similar type I adsorption desorption curve. As the Ni
6
F. Cheng et al. Applied Catalysis A, General 643 (2022) 118752
Table 2 Table 3
Physicochemical properties of Ni-TS-1-x (x = 1, 5, 10). Physicochemical properties of fresh TS-1(F-TS-1), reactive TS-1(R-TS-1) and
No. Catalysts W (Ni) BET surface External Pore
regenerate TS-1(R*-TS-1).
(wt %) area (m2/g) surface area volume No. Samples BET surface area Total pore volume W (Ni)
(m2/g) (cm3/g) (m2/g) (cm3/g) (wt %)
1 TS-1 0 480 99 0.29 1 F-TS-1 480 0.29 ——
2 Ni-TS-1–1 0.02 475 84 0.28 2 R-TS-1 75 0.11 ——
3 Ni-TS-1–5 0.13 463 74 0.26 3 R* -TS-1 408 0.26 ——
4 Ni-TS- 0.22 433 70 0.25 4 F-Ni-TS-1 463 0.26 0.13
1–10 5 R-Ni-TS-1 137 0.14 0.11
6 R* -Ni-TS-1 423 0.24 0.14
Fig. 6. Fluctuation of H2O2 conversion (a) and EG selectivity (b) with the reusability for TS-1 and Ni-TS-1 in the oxidative hydration of ethylene reaction. * In the
first five reactions, the catalyst was only dried under low temperature (30 ℃), and the treatment condition of “calcinate” was roasted for 2 h at 550 ℃. *Reaction
conditions of TS-1 and Ni-TS-1: 353 K, 20 bar, 2 h, H2O2 1.6 M, cat. 0.25 g.
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F. Cheng et al. Applied Catalysis A, General 643 (2022) 118752
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