Selective Hydrogenation of 2-Methylfuran and 2,5-Dimethylfuran over Atomic Layer Deposited Platinum Catalysts on Multiwalled Carbon Nanotube and Alumina Supports

Article abstract of DOI:10.1002/cctc.201601215

2-Methylfuran (2MF) and 2,5-dimethylfuran (DMF) were hydrogenated in the vapor phase to the corresponding tetrahydrofurans, linear 2-ketones, and alcohols over Pt nanoparticles supported on multiwalled carbon nanotubes (MWCNTs) and alumina by atomic layer deposition. The hydrogenation behavior of sub-nanometer Pt deposited on alumina was influenced by the acidity of the support. Relative to a commercial Pt/C catalyst, the Pt/MWCNT catalyst was found to contain similarly sized Pt nanoparticles that display a broader size distribution and significantly more n-alkanes than oxygenates during hydrogenation of these alkyl-substituted furans.

Full text of DOI:10.1002/cctc.201601215

Accepted Article
Title: Selective Hydrogenation of 2-Methylfuran and 2,5-Dimethylfuran
over Atomic Layer Deposited Pt Catalysts on Multi-Walled
Carbon Nanotube and Alumina Supports
Authors: Jungshik Kang, Xinhua Liang, and Vadim Guliants
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the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: ChemCatChem 10.1002/cctc.201601215
Link to VoR: http://dx.doi.org/10.1002/cctc.201601215
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Selective Hydrogenation of 2-Methylfuran and 2,5-Dimethylfuran
over Atomic Layer Deposited Pt Catalysts on Multi-Walled Carbon
Nanotube and Alumina Supports
Jungshik Kang[a], Xinhua Liang[b] and Vadim V. Guliants*[a]
2-Methylfuran and 2,5-dimethylfuran were hydrogenated in the
vapor phase to corresponding tetrahydrofurans, linear 2-ketones and
alcohols over Pt nanoparticles supported on multi-walled carbon
nanotubes (MWCNTs) and alumina by atomic layer deposition. The
hydrogenation behavior of sub-nm Pt deposited on alumina was
influenced by the support acidity. As compared to a commercial Pt/C
catalyst, the Pt/MWCNT catalyst contained similarly sized Pt
nanoparticles that displayed
a broader size distribution and
significantly more n-alkanes than oxygenates during hydrogenation
of these alkyl-substituted furans.
Figure 1. Bright-field TEM images of (left) Pt ALD/MWCNT and (right) Pt
ALD/Al2O3.
2-Methylfuran (2MF) and 2,5-dimethylfuran (DMF) are
important biomass-derived intermediates in the fine chemical
processing, which are mainly used for the synthesis of
HAADF-STEM imaging of the ALD and commercial Pt
catalysts (Figure 2) revealed significant differences in the size
and shape of Pt nanoparticles in these catalysts that were
evaluated with the help of ImageJ software.[7]
crysanthemate
pesticides,
perfume
intermediates
and
chloroquinine lateral chains in pharmaceutical intermediates.[1]
Upgrading these substituted furans to valuable chemicals often
involves hydrogenation of the aromatic furan ring and its
opening via hydrogenolysis, which typically result in mixtures of
substituted tetrahydrofurans (THFs), ketones and alcohols.[2]
Although highly selective hydrogenation of 5-hydroxymethyl
furfural to DMF and furfural to 2-MF has been reported,[3] further
improving the selectivity of DMF and 2-MF hydrogenation and
hydrogenolysis reactions is crucial for producing desired
products in high yield. Moreover, while many studies reported Pt
(and Pd) to be highly promising catalysts for these reactions,[4]
the current understanding of the molecular structure-reactivity
relationships for supported Pt catalysts for 2-MF and DMF
hydrogenation reactions is still rather limited.
Highly dispersed carbon-supported Pt nanoparticle used as
catalysts in selective hydrogenation reactions have been
traditionally prepared by liquid-phase processing.[4] Although
these methods can produce very small Pt nanoparticles, they
lack the ability to precisely control their size distributions, which
has significant implications for their catalytic properties. On the
other hand, atomic layer deposition (ALD) has emerged in
recent years as a promising novel method of growing very small
Pt and other noble metal nanoparticles with improved size
control layer by layer via alternating exposure of the catalytic
support
to
trimethyl(methylcyclopentadienyl)
platinum
{Me3(MeCp)Pt} and O2.[5] This study probes the nanostructures,
surface characteristics and catalytic behaviors of Pt ALD
catalysts grown on multi-walled carbon nanotubes[6] and alumina
and compares these characteristics with those of a commercial
Pt/C catalyst obtained by conventional liquid-phase processing.
Figure 2. HAADF-STEM images and particle size distributions of (top) Pt/C
(BASF), (center) Pt ALD/MWCNT, and (bottom) Pt ALD/Al2O3 (average
particles size; 2.39, 2.23 and 0.97 nm, respectively).
[a]
[b]
Prof. V.V. Guliants and Dr. J. Kang
Department of Biomedical, Chemical and Environmental
Engineering, University of Cincinnati
Cincinnati, OH 45221 (USA)
E-mail: vadim.guliants@uc.edu
Prof. Xinhua Liang
The bright-field TEM images of the Pt ALD catalysts (Figure
1) revealed the presence small Pt nanoparticles supported on
MWCNTs, whereas only few Pt nanoparticles could be
discerned in the alumina supported catalysts due to lower
contrast difference between Pt and alumina, smaller Pt loadings
and smaller Pt particle sizes in this catalyst. Therefore, HAADF-
SEM imaging was employed to characterize these catalysts due
to higher Z-contrast differences in this method.
Department of Chemical and Biochemical Engineering,
Missouri University of Science and Technology
Rolla, MO 65409 (USA)
E-mail: liangxin@mst.edu
Supporting information for this article is given via a link at the end of
the document.
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10.1002/cctc.201601215
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Visual observation revealed
a
significantly broader size
not accompanied by CO desorption suggesting that the
Boudouard reaction may be responsible for its formation at
higher temperatures.[9] A similar reaction behavior during CO
TPD was reported recently by Gould et al.[9] for Pt ALD catalysts
supported on alumina.
distribution of Pt nanoparticles in the commercial Pt/C catalyst
as compared to the Pt ALD/MWCNT, which displayed greater
particle size uniformity. The Pt ALD/Al2O3 catalyst showed the
presence of significantly smaller Pt particles than in the other
two catalysts due to lower Pt loading and stronger Pt-support
interactions in this catalyst. However, these differences were not
apparent when the average Pt particle size was evaluated by the
ImageJ software, e.g., 2.32±1.50 nm for Pt ALD/MWCNT vs.
2.39±1.22 nm for Pt/C (BASF) shown in Figure 2. It should be
noted that ImageJ overestimated the average size of Pt
nanoparticles in the commercial Pt/C catalyst due to reduced
contrast differences for the small Pt nanoparticles (ca. 1 nm and
smaller) present in this catalyst. In the case of the Pt ALD/Al2O3
catalyst, ImageJ was unable to recognize smaller Pt
nanoparticles present in this catalyst due to reduced contrast
differences with alumina. Therefore, the Pt particle sizes were
measured manually from STEM images, which also
overestimated the average particle size (0.97±0.37 nm) in this
catalyst (Figure 2).
The CO desorption/reaction spectra of the two carbon-
supported Pt catalysts (Figures 3S and 4S) exhibited complex
behavior that was dominated by CO desorption from and
reactions on the carbon-based surfaces. Both catalysts exhibited
two CO desorption peaks centered at ca. 350 and 660K.
According to Marchon et al.[10] and Li et al.[11], these peaks are
likely due to desorption of CO from weakly bound surface
species, such as carbonyl and/or cyclic ethers present on the
surface of polycrystalline carbon and
carbon nanotubes,
respectively. Some CO2 was also observed during CO TPD from
the 5 wt. % Pt/C catalyst (BASF) with peaks at ca. 360, 430 and
680K. The lowest temperature peak at 360K corresponded to a
similar feature observed for the 0.47 wt. % Pt ALD/Al2O3 catalyst
suggesting that the WGS reaction may be responsible for its
formation, whereas the CO2 evolution at higher temperatures
agreed well with CO2 peaks observed during CO TPD from
polycrystalline graphite by Marchon et al.[10] Marchon et al.[10]
observed CO2 desorption at 443 and 673K and explained it by
thermal decarboxylation of lactone groups in the surface of
polycrystalline graphite, whereas Li et al.[11] assigned the high
temperature CO2 peak (693K) to decomposition of carboxylic
anhydrides. On the other hand, the Pt ALD/MWCNT catalyst
exhibited two distinct CO2 loss features, i.e., a peak at ca. 390K
likely associated with the WGS reaction, and a shallow peak at
460K with a long tail extending to ca. 550K suggesting that the
MWCNTs in this catalyst contained significantly fewer surface
defects and of a different kind, such as carboxylates,[11] as
compared to the carbon support in the commercial Pt/C catalyst.
The HAADF-STEM images were further examined in order to
gain insights into the structure of small Pt nanoparticles in these
catalysts. While Pt particles smaller than ~2 nm were not
ordered, only few ~2.3 nm Pt particles present in the Pt/C
catalyst (BASF) were oriented appropriately to show the
presence of atomic planes (Figure 1Sa). The contrast profile
analysis in the direction normal to these planes indicated regular
d-spacings of 2.27±0.03 Å that agreed well with d(111) = 2.27 Å
in the bulk Pt structure. Although significant Pt lattice contraction
(5-10%) has been reported for very small Pt nanoparticles (<2
nm),[8] it is expected to be negligible for larger Pt particles, such
as the ~2.3 nm particle shown in Figure 1Sa. The Pt
ALD/MWCNT catalyst showed the presence of similarly sized
hexagonal Pt particles showing regular arrays of Pt atomic
columns (Figures 1Sb and c) as well as Pt nanoparticles
displaying a series of the (111) planes (Figure 1Sd) and (100)
planes (Figure 1Se). The distances between the nearest-
neighbor atomic columns in Figures 1Sb and c were determined
by the contrast profile analysis indicating that these particles
possessed essentially the bulk structure of Pt viewed along the
[110] crystallographic direction. The high-resolution STEM
images of the Pt ALD/Al2O3 catalyst were also examined, but
revealed no atomic level details due to the presence of smaller
Pt nanoparticles in this catalyst and reduced elemental contrast
between Pt and the alumina support material.
CO TPD spectra also revealed evolution of hydrogen from
these supported Pt catalysts. The majority of this hydrogen was
chemisorbed by the Pt nanoparticles during their reduction in
hydrogen. The two carbon-supported catalysts displayed a low
temperature peak at ca. 420K, which was assigned to hydrogen
chemisorbed at Pt atoms located in bulk-like lattice sites.[12]
However, the largest H2 peaks were observed at ca. 600 and
680K for the 5 wt. % Pt/C (BASF) and 5.48 wt. % Pt
ALD/MWCNT catalysts, respectively. The peaks above 673K
were previously assigned to hydrogen strongly bonded to defect
sites in Pt nanoparticles or ultradispersed Pt nanoparticles.[12]
Some other H2 evolution features were also observed in the TPD
spectra of these two catalysts at 500-720K suggesting marked
differences in relative abundance of these ultradispersed Pt
nanoparticles. The 0.47 wt. % Pt ALD/Al2O3 catalyst displayed
the highest concentration of hydrogen desorbed at high
temperature, followed by the 5 wt. % Pt/C (BASF) and 5.48
wt. % Pt ALD/MWCNT catalysts, respectively. Moreover, the
0.47 wt. % Pt ALD/Al2O3 catalyst desorbed hydrogen at the
The surface sites present in these catalysts were further
probed by the temperature-programmed desorption/reaction of
CO (Figures 2S-4S). The TPD spectra shown in Figure 2S
indicated simultaneous evolution of CO and CO2 that peaked at
ca. 360K for the 0.47 wt. % Pt ALD/Al2O3 catalyst. The
observation of CO2 in this temperature range suggested the
occurrence of the water-gas shift (WGS) reaction with the
participation of surface hydroxyls present on the alumina surface. lowest temperature (580K) followed by the commercial 5 wt. %
However, H2 formed in this reaction was adsorbed strongly on
the Pt surface at these temperatures, which delayed the onset of
H2 desorption to higher temperatures (>450K). The second,
smaller peak of CO2 was also observed at ca. 530K, which was
Pt/C (600K) and 5.48 wt. % Pt ALD/MWCNT catalysts (660K).
Similar differences in H2 desorption behavior were recently
reported by Li et al.[11] for supported Pt and Pt-Ru catalysts used
in selective hydrogenation of phenylacetylene, where the highest
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10.1002/cctc.201601215
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reactivity was observed for the Pt/CNT catalyst that displayed
the lowest H2 desorption temperature. Therefore, hydrogen
desorption behavior of supported Pt catalysts is expected to
have important consequences for their reactivity in other
selective hydrogenation reactions, such as those of 2-MF and
2,5-DMF, which is discussed below.
100
80
60
40
20
0
100
80
(a)
60
Conv.
Butane
Pentane
2MTHF
2-Pentanone
2-Pentanol
1-Pentanol
The surface acidity of these catalysts was probed by ammonia
TPD, which is an established method of determining the acid
characteristics of heterogeneous catalysts due to the small size,
stability, and strong basicity (pKa = 9.2) of the ammonia
molecule.[13] The types of surface acid sites distinguished by the
temperature ranges of ammonia desorption are typically
categorized as weak (423-573K), moderate (573-723K), and
strong (723-923K). The ammonia TPD profiles of the three
catalysts investigated in this study are shown in Figures 5S-7S.
It can be seen from Figure 5S that the 0.47 wt. % Pt ALD/Al2O3
catalyst is distinguished from both the 5 wt. % Pt/C (BASF) and
5.48 wt. % Pt ALD/MWCNT catalysts (Figures 6S and 7S,
respectively) by the presence of moderately strong acid sites.
The 5 wt. % Pt/C (BASF) and 5.48 wt. % Pt ALD/MWCNT
catalysts displayed similar acidity characteristics, with the Pt
ALD/MWCNT having considerably less weak surface acidity.
40
20
0
350
400
450
500
550
Reaction temperature, K
100
80
60
40
20
0
100
80
60
40
20
0
(b)
Conv.
Butane
Pentane
2MTHF
2-Pentanone
2-Pentanol
1-Pentanol
others
100
80
60
40
20
0
100
80
60
40
20
0
(a)
Conversion
Hexane
2,5 DMTHF
2-Hexanone
2-Hexanol
others
400
450
500
550
Reaction temperature, K
Figure 4. 2-MF hydrogenation (H2/2-MF = 10, GHSV = 2,500 h-1) over (a)
5.48 wt. % Pt ALD catalyst supported on MWCNTs and (b) commercial 5
wt. % Pt/C catalyst.
are shown in Figures 3-5, where these catalysts are compared
to the commercial 5 wt. % Pt catalyst supported on carbon
(BASF). As expected, these results indicated that 2,5-DMF is
more reactive than 2-MF due its greater activation by the two
methyl group substituents on the furan ring. 2,5-DMF was
completely converted over both the Pt ALD/MWCNT and
commercial catalysts over the entire temperature range
investigated (353-573K) and H2/2,5-DMF ratios of 3 and 10.
However, the Pt ALD/MWCNT catalyst was much more active in
deep 2,5-DMF hydrogenation to hexane over the entire
temperature range investigated than the commercial 5 wt. %
Pt/C catalyst, while the latter catalyst exhibited a yield of 2-
hexanol (ca. 80 mol. %) at low temperatures (Figure 3). We
believe that the presence of moderately strong acid sites in the
Pt ALD/MWCNT catalyst (Figure 5S) may be responsible for the
observed deep 2,5-DMF hydrogenation to hexane over this
catalyst. The yield of 2-hexanol over the commercial catalyst
declined at higher temperatures, which was accompanied by the
concomitant rise of 2-hexanone yield because the formation of
the latter molecule becomes more thermodynamically favorable
at elevated temperatures.
400
420
440
460
480
500
520
540
560
Reaction Temperature, K
100
80
60
40
20
0
100
(b)
80
60
40
20
0
Conversion
Hexane
2,5 DMTHF
2-Hexanone
2-hexanol
Others
350
400
450
500
550
600
Reaction Temperature, K
Figure 3. 2,5-DMF hydrogenation (H2/2,5-DMF = 10, GHSV = 2,500 h-1)
over (a) 5.48 wt. % Pt ALD catalyst supported on MWCNTs and (b)
commercial 5 wt. % Pt/C catalyst.
Both the Pt ALD/MWCNT and commercial catalyst exhibited
similar behavior in 2-MF hydrogenation, while the Pt ALD/Al2O3
catalyst was slightly less active below 473K (Figure 4). Both
catalysts resulted in a ca. 80 mol. % yield of 2-pentanone at
The results of 2,5-DMF and 2-MF hydrogenation over atomic
layer deposited Pt catalysts on MWCNT and alumina supports
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573K and 100 % 2-MF conversion, the balance being a mixture
of butane and some pentane.
detected over this catalyst over the entire temperature range
investigated at H2/2,5-DMF
= 3. Under H2-rich conditions
(H2/2,5-DMF = 10), the yield of of 2-hexanone reached ca. 60
mol. % at 393K, while 2,5-DMTHF was present in trace amounts.
Some 2-hexanol (ca. 10 mol. %) was also detected at low
temperatures (423K). However, these products disappeared
when the reaction temperature reached 473K, which was
accompanied by a rapid rise in hexane formation (100 mol. %).
The yield of hexane declined above 523K due to hexane
cracking, but the extent of cracking was less at H2/2,5-DMF = 10
as compared to H2/2,5-DMF = 3: ca. 15 mol. % vs. 30 mol. % at
573K. It is interesting to observe the absence of cracking
reactions over the Pt ALD/MWCNT catalyst, which suggests the
role of moderately strong acidity of the alumina support (Figure
5S) in these reactions. The role of alumina support acidity was
also manifested in the case of 2-MF hydrogenation (Figure 5c),
where its conversion remained relatively constant at ca. 40
mol. % at 353-473K and declined to ca. 20 mol. % at 548K
probably due to surface coking with carbonaceous deposits.
This catalyst also displayed a complex distribution of furan ring
hydrogenation and C-O bond hydrogenolysis products
suggesting a generally greater role played by the acidic alumina
support during 2-MF hydrogenation over the 0.47 wt. % Pt
ALD/alumina catalyst.
100
80
60
40
20
0
100
80
60
40
20
0
(a)
Conversion
Hexane
2,5 DMTHF
2-Hexanone
2-Hexanol
others
400
420
440
460
480
500
520
540
560
Reaction temperature, K
100
80
60
40
20
0
100
80
60
40
20
0
(b)
Conversion
Hexane
2,5 DMTHF
2-Hexanone
2-Hexanol
others
We attempted to explain the catalytic behavior of the Pt ALD
and commercial Pt/C catalysts on the basis of their structural
differences. The Pt ALD/Al2O3 catalyst was considerably less
selective to oxygenates during 2,5-DMF hydrogenation than the
commercial Pt/C and Pt ALD/MWCNT catalysts producing
instead n-hexane in a 100 mol. % yield. The significantly smaller
Pt nanoparticle size in the Pt ALD/Al2O3 catalyst coupled with a
high concentration of relatively low-temperature H2 desorption
sites (580K) probably contributed to greater activity and resulting
deep hydrogenation behavior of this catalyst towards 2,5-DMF.
On the other hand, these surface sites apparently possessed
insufficient activity towards 2-MF, as its conversion did not
400
420
440
460
480
500
520
540
560
Reaction temperature, K
100
80
60
40
20
0
100
(c)
Conv.
Butane
Pentane
2MTHF
2-Pentanone
2-Pentanol
Others
80
60
40
20
0
exceed 50 mol.
% over the entire temperature range
investigated. The lower catalytic activity of the Pt ALD/Al2O3
catalyst in 2-MF hydrogenation coupled with the surface acidity
of the alumina support contributed to a complex product
distribution observed for this catalyst.
The Pt ALD/MWCNT catalyst displayed a similar catalytic
activity during 2,5-DMF hydrogenation as compared to the
commercial Pt/C catalyst but lower selectivity to oxygenates and
higher selectivity to n-hexane, most likely due to the presence of
defect sites in Pt nanoparticles or ultradispersed Pt
nanoparticles manifested in high desorption temperature of H2
(680K). On the other hand, this ALD catalyst displayed very
similar catalytic behavior to that of the commercial Pt/C catalyst
during 2-MF hydrogenation.
350
400
450
500
550
Reaction temperature, K
Figure 5. Hydrogenation of substituted furans over 0.47 wt. % Pt ALD
catalyst supported on alumina: (a) H2/2,5-DMF = 3, (b) H2/2,5-DMF = 10,
and (c) H2/2-MF = 10. GHSV = 2,500 h-1.
The 0.47 wt. % Pt ALD catalyst supported on alumina was
highly active in 2,5-DMF hydrogenation over the entire
temperature range investigated (100 % conversion). Under
relatively H2-lean conditions (H2/2,5-DMF = 3) this catalyst
exhibited ca. 50 mol. % yield of 2-hexanone and 40 mol. % yield
of 2,5-DMTHF at 393K, which rapidly declined with temperature,
whereas the yield of hexane reached 100 mol. % at 473-523K
and then decreased above 523K to 70 mol. % yield likely due to
occurrence of cracking reactions (Figure 5b). No 2-hexanol was
Experimental Section
Experimental details are available in the Supporting Information.
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Acknowledgements
This research was supported by the National Science
Foundation under Grant no. CBET-1236210.
Keywords: Hydrogenation • Hydrogenolysis • Atomic layer
deposition • Platinum • Nanoparticle
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Entry for the Table of Contents
Layout 1:
COMMUNICATION
2-MFand 2,5-DMF were
hydrogenated over
Jungshik Kang, Xinhua
Liang, Vadim V. Guliants*
nanoparticulate Pt catalyst
supported on multi-walled
carbon nanotubes by
atomic layer deposition
(ALD). ALD resulted in a
broader Pt nanoparticle
dispersion and
significantly more n-
alkanes than oxygenates
as compared to
Page No. – Page No.
Title
Selective Hydrogenation
of 2-Methylfuran and 2,5-
Dimethylfuran over
Atomic Layer Deposited
Pt Catalysts on Multi-
Walled Carbon Nanotube
and Alumina Supports
commercial Pt/C catalyst.
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