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Coordinatively Unsaturated Al3+ Sites Anchored Subnanometric Ruthenium Catalyst for Hydrogenation of Aromatics Nanfang Tang, Yu Cong, Qinghao Shang, Chuntian Wu, Guoliang Xu, and Xiaodong Wang ACS Catal., Just Accepted Manuscript • DOI: 10.1021/acscatal.7b01816 • Publication Date (Web): 07 Aug 2017 Downloaded from http://pubs.acs.org on August 7, 2017
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Figure 1. A, B) HR-TEM images of Ru/rp-Al2O3. C) XRD pat-terns of rp-Al2O3 and Ru/rp-Al2O3. D, E, F) HAADF-STEM images of Ru/rp-Al2O3. The circles and squares in the figures represent the single Ru atoms and subnanometric Ru clus-ters, respectively. 123x190mm (150 x 150 DPI)
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Figure 2. A) 27Al MAS NMR spectra (solid line) and their deconvolution results (short dot) of rp-Al2O3, Ru/rp-Al2O3, comm-Al2O3, and Ru/comm-Al2O3, B) Raman spectra (solid line) and their deconvolution results (short dot) of Ru/rp-Al2O3(c) and Ru/comm-Al2O3(c), C) H2-TPR profiles of the catalysts of Ru/rpAl2O3(c) and Ru/comm-Al2O3(c). 188x401mm (150 x 150 DPI)
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Figure 3. A) Ru 3d XPS spectra of Ru/rp-Al2O3 and Ru/comm-Al2O3, B) CO-DRIFT spectra of the catalysts of Ru/rp-Al2O3 and Ru/comm-Al2O3. 187x258mm (150 x 150 DPI)
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Subnanometric Ru catalyst has been prepared through Ru atoms and clusters anchored on Al2O3 rich in coordinatively unsaturated Al3+penta centers, which exhibits special electronic features and high activity for hydrogenation of aromat-ics without side products under mild reaction conditions. 187x173mm (150 x 150 DPI)
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Coordinatively Unsaturated Al3+ Sites Anchored Subnanometric Ruthenium Catalyst for Hydrogenation of Aromatics Nanfang Tang,† Yu Cong,*† Qinghao Shang,†‡ Chuntian Wu,† Guoliang Xu,† and Xiaodong Wang† †Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China ‡University of Chinese Academy of Sciences, Beijing 100049, China ABSTRACT: Single metal atoms and metal clusters have attracted much attention because of their high dispersity, special electronic structures and uniformity of active sites as heterogeneous catalysts, but it is still challenging to generate stable single atoms and clusters with high metal loadings. Supports play a crucial role in determining particle morphology and maintaining dispersion. Herein we synthesize an amorphous alumina with 29 % coordinatively unsaturated pentacoordinate Al3+ (Al3+penta) sites, which can anchor atomically dispersed Ru species with 1 wt% loading. Strong interactions between Ru and Al3+penta centers were detected, resulting in distinct Ru geometric and electronic features. When used in benzene hydrogenation reaction, fairly high specific activity (TOF = 5180 h-1) were obtained. The high catalytic performance is considered closely correlated with the high utilization of special Ru active sites.
KEYWORDS: aromatics hydrogenation, alumina, atomically dispersed catalysts, ruthenium, heterogeneous catalysis The complete hydrogenation of aromatics without side products is an important transformation in the synthesis of fine chemicals and intermediates.1 Supported metal catalysts, especially Ru based catalysts are very promising and have been widely investigated.2 Whereas it is still challenging to improve the catalytic activity to a higher level of about the currently used homogeneous catalysts and stabilize the active metal species.3 In recent years, atomically dispersed metal catalysts have attracted great attention due to their excellent catalytic performance and high atom efficiency.4 In 2011, Zhang et al. reported a single-atom catalyst of only isolated single Pt atoms anchored onto the surfaces of iron oxide nanocrystallites, exhibiting extremely high activity and stability for both CO oxidation and preferential oxidation of CO in H2, and first proposed the concept of single-atom catalysis (SAC).5 Following that, single-atom or cluster catalysts with Pd, Ir, Rh, Au, etc. as the active species were extensively fabricated and showed super high activity in selective hydrogenation, water gas shift and many other reactions.6 Therefore, it would be an effective way to prepare atomically dispersed Ru catalysts with the aim of pursuing high catalytic performance for aromatics hydrogenation. Preparation technique is of crucial importance for atomically dispersed catalysts. Jones et al. developed a single Pt atom catalyst with strong sinter-resistant ability through an atom-trapping approach.7 Liu et al. produced a stable atomically dispersed Pd/TiO2 catalyst via a photochemical route.8 Liu et al. reported a new strategy for the generation of single Pt atoms and Pt clusters with
exceptionally high thermal stability, formed within purely siliceous MCM-22 during the growth of a twodimensional zeolite into three dimensions.9 The above successes mainly lied in the strong metal-support interactions (SMSI), which significantly stabilized the metal species and prevented the aggregation. Nevertheless, the generation of highly stable single atoms and clusters is still a challenging task. The synthesis and application of atomically dispersed Ru catalysts have not been attached enough importance, and alumina, the most popular industrial catalyst and catalyst support which has been widely applied in petroleum refinement, automobile emission control, etc., has rarely been reported as support for the atomically dispersed catalysts. Hence, developing a facile and sustainable method for synthesis of atomically dispersed Ru/Al2O3 catalyst is of great significance. It was reported by Kwak et al. that coordinatively unsaturated pentacoordinate Al3+ (Al3+penta) centers present on the (100) facets of commercial γ-Al2O3 can serve as anchor sites to anchor atomically dispersed Pt.10 Thus, synthesis of alumina with large amount of pentacoordinate Al3+ sites plays an essential role in the preparation of atomically dispersed Ru catalyst. Herein, we synthesized an Al2O3 rich in Al3+penta centers (named as rp-Al2O3), which provided enough “defect sites” to anchor atomically dispersed Ru species and to modulate the geometric and electronic features of Ru species. With the strong interactions between Ru species and pentacoordinate Al3+ sites, the Ru/rp-Al2O3 catalyst exhibits extremely high catalytic activities and stabilities in complete hydrogenation of aromatics without side reaction under mild reaction conditions.
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the brightness variations of the clusters and by comparing intensities with single atoms, we found that most of the subnanometric Ru clusters possessed a two-dimensional (2D) raft-like morphology. This high dispersion and special morphology of Ru species are considered to be resulted from Ru atoms anchoring preferentially on the coordinatively unsaturated pentacoordinate Al3+ sites, owing to the SMSI between Ru species and rp-Al2O3.12 In order to clarify the nature of SMSI, 27Al solid state MAS-NMR spectra were recorded. As shown in Figure 2A,
Figure 1. A, B) HR-TEM images of Ru/rp-Al2O3. C) XRD patterns of rp-Al2O3 and Ru/rp-Al2O3. D, E, F) HAADF-STEM images of Ru/rp-Al2O3. The circles and squares in the figures represent the single Ru atoms and subnanometric Ru clusters, respectively.
Al2O3 rich in Al3+penta centers was prepared by evaporation induced self-assembly (EISA) method (denoted as rpAl2O3), and the catalyst was prepared by incipient wetness impregnation, followed by calcination (labeled as Ru/rpAl2O3(c)) and reduction (labeled as Ru/rp-Al2O3) with the Ru loading of 1 wt%. As shown in Figure 1A, 1B, no Ru nano particles but only amorphous alumina can be observed in the high resolution transmission electron microscopy (HR-TEM) images of Ru/rp-Al2O3. This is consistent with the result of XRD diffraction peaks, which are sensitive to the Al3+ distribution, namely (440), (400), (331), are absent on the rp-Al2O3, indicating a high degree of Al3+ disorder and amorphous phase of rp-Al2O3.11 After loading Ru species, there are no diffraction peaks at 2θ of 44.0o assigned to metallic Ru phase, indicating the high dispersion of Ru species. Ru clusters and individual atoms with fine dispersion are distinguished in the high-angle annular dark-filed scanning transmission electron microscopy (HAADF-STEM) images (Figure 1D, 1E, 1F). The Ru clusters composed loose and random ensembles of several of atoms, with dimensions ＜0.7 nm. According to
27
Figure 2. A) Al MAS NMR spectra (solid line) and their deconvolution results (short dot) of rp-Al2O3, Ru/rp-Al2O3, comm-Al2O3, and Ru/comm-Al2O3, B) Raman spectra (solid line) and their deconvolution results (short dot) of Ru/rpAl2O3(c) and Ru/comm-Al2O3(c), C) H2-TPR profiles of the catalysts of Ru/rp-Al2O3(c) and Ru/comm-Al2O3(c).
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three peaks centered at 5, 35 and 65 ppm chemical shift are observed for the rp-Al2O3 and Ru/rp-Al2O3 samples. The two characteristic peaks at 5 and 65 ppm represent Al3+ cations in octahedral (Al3+octa) and tetrahedral (Al3+tetra) coordination, and that at 35 ppm represents coordinatively unsaturated Al3+ cations with pentahedral coordination (Al3+penta).13 We can see from the figure that the rp-Al2O3 synthesized in this work contains a great number of Al3+penta site, which accounts for about 29 %, and the Al3+octa site and Al3+tetra site account for 50 % and 21 % respectively. These plenty of Al3+penta site are probably formed in thermal decomposition and dehydroxylation of crown-ether-type complexes at elevated temperatures, derived from the hydrophilic poly(ethyleneoxide) of P123 coordinating with aluminum ions in hydrolysis and condensation.14 Whereas after loading Ru species, the Al3+penta site of Ru/rp-Al2O3 decreases to 13 %, and the Al3+octa site and Al3+tetra site increase to 61 % and 26 % separately. This indicates that Ru is selectively anchored onto the coordinatively unsaturated Al3+penta site. The effect of water in the impregnation process was also examined (Figure S1). Part of Al3+penta site (21 % for the remaining) is destroyed but transformed mainly to Al3+tetra site (26 %) and little to Al3+octa site (53 %). The enormous decrease in Al3+penta site and preferential increase in Al3+octa site on the Ru/rp-Al2O3 could explain that the coordinative saturation of these pentacoordinated Al3+ is responsible for the strong interactions between Ru species and alumina support.
exhibits a TPR peak at 210 oC. This peak can be attributed to the reduction of RuO2 to Ru0 with larger particle size. Whereas, the Ru/rp-Al2O3(c) exhibits a fairly low and narrow TPR peak at 170 oC, reflecting the fine and uniform dispersion of ruthenium species on rp-Al2O3.17 By comparing the H2 consumption, we know that ruthenium species on Ru/rp-Al2O3(c) are not completely reduced as Ru/comm-Al2O3(c), but in the state of partial oxidation, just similar to other single atom catalyst reported in the literature.12a These further indicate that the strong interactions between Ru species and coordinative unsaturated Al3+penta sites do exist on Ru/rp-Al2O3 catalyst. As we all know, the electronic structures of active phases are closely correlated with its morphology and coordination environment, which further influence the catalytic behavior. Therefore, the XPS and CO-DRIFT spectra were collected to study the electronic structures of Ru species supported on alumina. In the XPS spectra of Figure 3A, a strong C1s standard peak of graphite at 284.4 eV and a weak C1s peak at 288.3 eV ascribed to the adsorbed hydrocarbons or carbonates, presumably picked up during exposed to the air or produced during the drying process, are shown. After deconvolution, the Ru/comm-Al2O3 shows the binding energy at 280.4 eV (Ru 3d5/2) and 284.7 eV (Ru 3d3/2), indicating the presence of Ru0.18 Whereas the Ru/rp-Al2O3 exhibits higher binding energy at 280.9 eV and 285.0 eV, which may be assigned to partially oxidized Ru species.19 These results clearly reveal the special
To further elaborate the role of coordinative unsaturation Al3+penta centers, commercial γ-Al2O3 (denoted as comm-Al2O3, the physical properties can be found in Supporting Information) without Al3+penta sites and the resulted Ru/comm-Al2O3 catalyst were studied for comparison. Instead of complete dispersion of Ru on the rpAl2O3, diffraction peak at 2θ = 44.0o attributed to (101) of hexagonal metallic Ru can be observed in the XRD patterns of Ru/comm-Al2O3 (Figure S2).15 3D Ru nanoparticles with average size of 2.4±1.0 nm can also be clearly observed from the HAADF-STEM images (Figure S3). These provide additional information that the dispersion state and the morphology of the Ru species are closely correlated to the coordinative unsaturation Al3+penta sites. Raman spectroscopy is a powerful means of studying the interactions of surface species. On the spectra of calcined catalysts (Figure 2B), three Raman bands, namely Eg, A1g, and B2g modes of RuO2 are detected at 504 cm-1, 618 cm-1, and 686 cm-1, respectively.16 The intensity ratios of Eg, A1g and B2g bands (IEg/IA1g, IEg/IB2g) are often used to diagnose the change of coordination between Ru and O. For Ru/rp-Al2O3(c), the calculated IEg/IA1g ratio (4.05) is much higher than that for Ru/comm-Al2O3(c) (0.65), and the calculated IEg/IB2g ratio (1.21) is obviously lower than that for Ru/comm-Al2O3(c) (2.61). These results indicate the great difference in Ru-O coordination, which may be induced by the strong interactions between Ru and coordinative unsaturation Al3+penta sites on Ru/rp-Al2O3(c). Such difference can also be verified by the H2-TPR results. It can be found in Figure 2C that the Ru/comm-Al2O3(c)
Figure 3. A) Ru 3d XPS spectra of Ru/rp-Al2O3 and Ru/comm-Al2O3, B) CO-DRIFT spectra of the catalysts of Ru/rp-Al2O3 and Ru/comm-Al2O3.
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Table 1. Catalytic performance of various catalysts for benzene hydrogenation to cyclohexane Ref.
Catalyst
t (h)
P (H2) (MPa)
T o ( C)
Yield a (%)
TOF -1 b (h )
This work
Ru/rp-Al2O3
1
3.0
80
100
5180
This work
Ru/commAl2O3
1
3.0
80
18.5
417
2.5
6.0
90
100
364
2.5
8.0
110
100
4000
1
0.28
22
100
1040
6
23a
[H4Ru4(h C6H6)4][BF4]2
23b
Ru/MMT
23c
Ru/Zeolite-Y
23d
Ru/CNTs
0.5
4.0
80
99.97
6983
23e
Ru/SBA-15
-
1.0
20
100
85.3
23f
Ru/MOF
1.5
6.0
60
96
3200
23g
Ir NPs
0.8
4.0
20
100
375
23h
Ir NPs@zeolite
8
0.3
25
100
3190
23i
G1-HMDIg Ru
0.5
3.0
85
97.5
4675
23j
Rh/HEA-C16
6.6
0.1
20
100
91
23k
Rh/MWNTs
3
1
20
80
1038
23l
Rh(cod)-Pd/ j SiO2
2
3
40
52
1241
23m
Rh0.5Ni0.5
7
4.0
25
50.8
290
23n
PtRh/MWNTs
3
1
20
100
1953
a
c
d
e
f
i
h
b
Yield to cyclohexane, determined by GC. Turnover frequency defined as mole of benzene converted per mole of total metal loading per hour at a conversion lower than c d 30 %. MMT = montmorillonite. CNTs = Carbon nanotubes. e f g MOF = metal–organic frameworks. NPs = nanoparticles. a catalyst based on the first-generation dendrimer DAB(NH2)4 (G1) crosslinked by hexamethylene diisocyanate (HMDI). h i HEA = N-alkyl-N-(2-hydroxyethyl) ammonium salts. Mj WNTs = multiwalled carbon nanotubes. cod = cycloocta1,5-diene.
electronic state of Ru on rp-Al2O3. Similar phenomena have also been reported by other groups. 20 This can also explain the comparatively lower H2 consumption of Ru/rp-Al2O3 (c) in H2-TPR relative to Ru/comm-Al2O3 (c). Meanwhile, as shown in the CO-DRIFT spectra in Figure 3B, the adsorption of CO on the Ru/comm-Al2O3 produces a vibration at 2049 cm-1 and a visible shoulder at 2002 cm-1. The former band can be attributed to linearly adsorbed CO on Ru0 and the latter is symmetric stretching vibration of Ru0(CO)2.21 While in the case of Ru/rp-Al2O3, two new strong bands at 2066 cm-1 and 1988 cm-1 appear,
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which can be assigned to two different types of dicarbonyl species on partially oxidized Ru sites (Ruδ+(CO)2).22 It should be noteworthy that, more intense bands of CO adsorption on Ru/rp-Al2O3 are displayed, due to the high dispersion of the supported ruthenium. In a word, the geometric and electronic features of Ru are significantly changed through SMSI, and it must affect the catalytic performance seriously. Catalytic performance of Ru/rp-Al2O3 in hydrogenation of benzene was tested and compared with Ru/commAl2O3 and also with those reported previously. We can see in Table 1 that the Ru/rp-Al2O3 shows a fairly high catalytic activity in benzene hydrogenation, with TOF of 5180 h-1 within 1 hour at 80 oC under 3 MPa H2. In contrast, the Ru/comm-Al2O3 catalyst shows a low catalytic activity, with TOF of 417 h-1 under the same reaction conditions. This performance is also comparable or superior to other catalysts reported in the literatures.23 Notably, Ru/rpAl2O3 can be recovered simply by filtration and reused five times without activity decay at conversions of 100 % and 60 % (Figure S4). Other arenes hydrogenation were also investigated (Table S1). Ru/rp-Al2O3 was active for various monosubstituted and disubstituted arenes such as toluene, p-xylene, m-xylene and o-xylene, and it showed high selectivity to decalin in hydrogenation of naphthalene. In summary, we prepared a Ru catalyst with subnanometric Ru species anchored on the coordinative unsaturation Al3+penta centers of amorphous alumina. Strong interactions between Ru species and coordinative unsaturation Al3+penta centers were detected, which leads to special geometric and electronic features of Ru species. When used in benzene hydrogenation reaction, the catalyst displayed high specific activity (TOF ≈ 5180 h-1). Our work provides a possibility for the generation of atomically dispersed metal catalysts with practical applications.
ASSOCIATED CONTENT Supporting Information. The Supporting Information is available free of charge on the ACS Publication website at http://pubs.acs.org. The details about activity tests, the characterizations such as HAADF-STEM, 27 Al MAS NMR, XPS, and CO-DRIFT, and the preparation of catalysts are given in the text (PDF).
AUTHOR INFORMATION Corresponding Author * E-mail:
[email protected].
Author Contributions This manuscript was written through contributions of all authors and they have given their approval to the final version of the manuscript.
Notes The authors declare no competing financial interest.
ACKNOWLEDGMENT
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This work is supported by National Nature Science Foundation of China (NSFC) under granted No. 21476229 and 21376236.
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