Boron-doped carbon nanodots dispersed on graphitic carbon as high-performance catalysts for acetylene hydrochlorination

Article abstract of DOI:10.1039/c9cc09701e

Boron-doped carbon nanodot materials, comprising evenly distributed BC₃-nanodots in a layered carbon matrix, are prepared through a pre-assembly assisted carbonization synthetic strategy. The prepared materials are endowed with high electron affinity and distortion resistance, which provides a stable framework while generating affinity to substrates.

Full text of DOI:10.1039/c9cc09701e

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DOI: 10.1039/C9CC09701E
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Boron-doped carbon nanodots dispersed on graphitic carbon as
high-performance catalysts for acetylene hydrochlorination
Received 00th January 20xx,
Accepted 00th January 20xx
Yuxue Yue,a† Bolin Wang,a,b† Saisai Wang,a Chunxiao Jin,a Jinyue Lu,a Zheng Fang,a Shujuan Shao,a
Zhiyan Pan,b Jun Ni,a Jia Zhao*a and Xiaonian Li *a
DOI: 10.1039/x0xx00000x
Boron-doped carbon nanodot materials, comprising layered chemical affinity and especially ultrahigh exposed surface area,
carbon materials and evenly distributed BC3-nanodots in the layer which are important for a wide range of applications, such as
matrix of materials, prepared through a pre-assembly assisted energy conversion/storage, water/gas purification, or
carbonization synthetic strategy. The prepared materials are catalysis.4 For example, several 2D graphene-like carbon-based
endowed with high electron affinity and distortion resistance, catalysts, such as g-C3N4,4d&e and NP-C600,4f have been
which provides a stable framework while generating affinity to reported to show excellent catalytic performance in acetylene
substrates.
hydrochlorination. However, like most layered structured
materials, the applications are basically hampered by the
serious distortion, especially in thermochemical applications,
mainly due to their defective degree and uneven electrostatic
potential distribution resulting from doping over the
materials.5 In general, 2D carbon materials doped with B, N, O,
S and P show very attractive physical and chemical properties.6
Among them, boron is a neighboring element of carbon with
high similarity in atomic size and electronic properties and
with the ability to form stronger covalent bonds with carbon
than with N, O, S or P.7 This ability has attracted the attention
of researchers concerning the durable and advanced
graphene-like boron carbide 2D layered materials.
Herein, we report a facile carbonization approach to
fabricate a catalyst of B-doped carbon nanodots (B-CNDs) from
mixed ionic liquids for acetylene hydrochlorination. We found
that the structure of layered carbon materials can be
converted to enhance their distortion resistance and generate
advanced chemical properties via reducing the dimension of
graphene down to carbon nanodots (CNDs) accompanied with
B-doping. Inspired by this finding, we developed an
optimization strategy by combining fine tailoring of the
nanodots with modifications through insertion of B atoms,
leading to the formation of BC3-containing nanodots dispersed
on 2D carbon materials, which can rival the performance of
metal-based catalysts. This work offers a new design for the
Emissions of toxic mercury contaminants in the production of
vinyl
chloride
monomer
(VCM)
via
acetylene
hydrochlorination, have attracted broad attention from
academics, industries, and countries, with the enforcement of
related environmental policies.1 Over the last several decades,
a variety of catalysts have been developed for acetylene
hydrochlorination (such as Au,2a-2d Pd,
Currently, significant progress has been made in metal-based
hydrochlorination catalysts, especially Au-based catalysts;2a-b
however, such catalysts are derived from precious-metal
resources with the problems of limited availability and high
costs, susceptibility to impurities, and poor stability, thus
tremendously limiting the development and application of
such systems.2a,3 In this context, it is necessary to perform a
broader search of efficient catalysts beyond metals to expand
the research horizon and metal-free carbon-based catalysts
would be another highly appealing candidate, due to their
comparable activity and stability but negligible price versus
those of metal-based catalysts.
2e-2f
Ru2g, and Cu2h).
Layered carbon materials or heteroatoms-doped carbon
materials are a multiple and largely unexploited source of two-
dimensional (2D) systems with the features of excellent
physical, electrical and transport properties, electro and
development
of
durable
catalysts
for
acetylene
a. Industrial Catalysis Institute of Zhejiang University of Technology, State Key
Laboratory Breeding Bas e of Green Chemistry-Synthesis Technology, Hangzhou,
310014, People’s Republic of China. E-mail: jiazhao@zjut.edu.cn; xnli@
zjut.edu.cn;
hydrochloriantion and has shed light on the structure-catalytic
activity relationship for layered carbon materials.
To achieve in-situ boron doping and simultaneous control
over the morphology and pore structure, we synthesized B-
CNDs through preassembly and then carbonized of ionic
liquids precursors (Scheme S1).4f,8 Briefly, an homogeneous
colloidal mixture was generated by performing a preassembly
b. Department of Environmental Engineering, Zhejiang University of Technology,
Hangzhou, 310014, People’s Republic of China
† These authors contributed equally to this work.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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a)
b)
peaks centered at 283.4, 284.2, 285.5, 286.4, and 291.3eV,
View Article Online
corresponding respectively to B-C, C-C (DspO2I: 1b0o.1n03d9in/Cg9)C, CC0-N97,0C1E-
O/C-B-O, and π-π* bonds,7c-e indicating the formation of
bonding between carbon and heteroatoms in B-CNDs.
Additionally, the C 1s peak slightly shifted in bonding energy
from 285.1 eV in p-G to 284.2 eV in B-CNDs, probably due to
the lowered Fermi level by the formation of a chemical bond
between carbon and electron deficient boron.9 The total B
content in B-CNDs is 5.27 at. %, which is predominantly
composed of -BC3 (190.8 eV) with a content of 60.2 at. %, -
BC2O (192 eV, 21.7 at. %), and -BCO2 (192.8 eV, 18.1 at. %)
(Figure S4, Table S1).7c-d Meanwhile, the HRTEM image (Figure
1c, insert), reveals the high crystallinity of the nanodots with a
lattice-spacing distance of approximately 0.26 nm, which is
close to that of the (200) lattice spacing of the BC3 sheet (Table
S2).10 The O 1s XPS and FT-IR spectral results (Figure S3e&f)
further supported the formation of B-C species and B-O groups
via carbonization.7d,11 The above results confirmed the
formation of -BC3 nanodots and their impregnation all over the
framework of the layered carbon materials.
Nanodots
100 nm
5 μm
c)
d)
B-CNDs
p-G
24.6
0.2603nm
43.4
Nanodots
50 nm
10 20 30 40 50 60 70 80
o
2 Theta (
)
IG
e)
ID
B-CNDs f)
B-1s
p-G-C
p-G
-BC2O
-BCO2
BC3
ID/IG=1.21
ID/IG=0.99
ID/IG=0.97
500
1000
1500
2000
)
2500
198 196 194 192 190 188 186 184
B.E. (eV)
Raman shift (cm-1
Figure 1 Morphology and structure characterization of B-CNDs: a) SEM, b) and c)
HRTEM images. d) XRD. e) Raman. f) XPS of B-1s.
process with stirring and ultrasonic treatment for an original
precursor solution containing boron-incorporated ionic liquids
(1-entyl-3-methylimidazolium tetraphenylborate, termed as
The structural strengths of B-CNDs in enhancing the
distortion resistance and chemical properties were further
explored by evaluating their catalytic activity toward acetylene
hydrochlorination at a different temperature and space
velocity. In Figure 2a, the hydrochlorination of acetylene
catalyzed by B-CNDs under 30 h-1 is shown to be initiated at
∼120 °C, and the conversion of acetylene normally increases
with the increase of temperature, reaching the values of over
98% at 220 °C. With the increase in the space velocity beyond
30 h-1, the acetylene conversion rapidly decreases to 32 % at
1480 h-1, in contrast to a relatively high acetylene conversion
and durability for B-CNDs at 1000 h-1 (Figure 2a&2b). However,
the p-G materials, with a similar morphology to that of B-
CNDs, contain only C and O elements and exhibit negligible
activity toward acetylene hydrochlorination (Figure 2a). To
investigate the origin of the activity in B-CNDs, we eliminated
the possibility of metal contaminations. In Figure S3a, only B,
C, N and O elements could be detected in B-CNDs from the
full-scan spectrum of XPS. Inductively Coupled Plasma (ICP)
[EMim][TPB])
and
pore
generator
(1-entyl-3-
methylimidazolium bis(trifluoromethylsulfonyl)imide, termed
as [EMim][NTf2]). The gelatinoids were then induced under
nitrogen at 150 °C to further promote the assembly between
two ionic liquids, followed by carbonization of the gelatinoids
into the materials of B-CNDs. As a result, these B-CNDs
predominantly contain multilayers, as shown in Figure 1a and
1b, while these nanodots possess a mean size of 10.5 nm, as
determined by HRTEM images in Figure 1c and Figure S1.
In our design, [EMim] cations were used as the comonomers
to form the main framework of graphene-like carbon
material.4f Meanwhile, a large number of [NTf2] anions were
partially decomposed into gas at elevated temperature,
leading to the formation of pore structures,8d as confirmed by
BET results in Figure S2. The B doping and carbonization
occurred simultaneously, with tetraphenylborate anion acting
as a boron source in polymerization at high temperature,
resulting in the formation of nanodots.7e When compared to
pristine graphene (p-G), the B-CNDs materials have an
enhanced density of exposed defect sites, with an amorphous
structure (Figure 1d &e), thus contributing to the
incorporation of heteroatoms.7c,9 Moreover, a positive shift
can be observed in the 2θ value of (002) and (101) reflections
for B-CNDs versus p-G.10 A comparison of the Raman spectra
of B-CNDs, p-G and p-G-C, demonstrates the defect levels of
materials (Figure 1e). The intensity was apparently higher in B-
CNDs (IG/ID, 1.21) than in p-G (IG/ID, 0.97) and p-G-C (IG/ID,
0.99), suggesting that the more abundant defect sites in B-
CNDs are mainly produced by B-doping, thus endowing the
materials with better catalytic ability during catalytic process.
To carefully examine the chemical environment of dispersed
nanodots, the contents and species of heteroatoms in B-CNDs
were analyzed by X-ray photoelectron spectroscopy (XPS)
(Figure 1f & Figure S3). The full scan spectra of XPS reveal that
B-CNDs consists of B, C, N and O elements. Figure S3c shows
the C1s spectra of B-CNDs, with five individual component
100
80
60
40
20
0
80
60
40
20
a)
b)
B-CNDs
B-CNDs
50 nm
p-G
0
120 160 200 240 30 740 1000 1480
Temperature (oC)
0
2
4
6
8
10
12
GHSV (h-1
)
TOS (h)
8
6
4
2
0
100
80
60
40
20
0
2.0
c)
d)
-BCO2
23
-BC2
-BC3
O
1.5
1.0
0.5
0.0
This work
29
30
24
25
8
12
13
18
20
16
15
26 28
27
9
22
11
19
17
21
10
14
1
g
2
3
g
s
g
-
-
s
-
s
0
5
10
15
20
25
D
s
N
D
N
D
D
N
C
N
-
C
C
C
-
B
-
-
B
B
B
References
Figure
2
Conversion of acetylene over B-CNDs a) at different reaction
temperatures and GHSV, b) at total GHSVs of 1000 h-1 and reaction temperature
of 220 °C. Insertion: TEM image of used B-CNDs. c) Specific B content estimated
from XPS. d) The calculated STY values of various metal-free catalysts.
2 | J. Name., 2012, 00, 1-3
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results reveal a trace level of Fe, Cu, Al and Ca elements in B- heteroatom dopants (e.g., B, N, O, S, and P) caVniewinAdrtuiccleeOntlhinee
CNDs (Table S3). The concentrations of N and above detected modulation of charge-density and eDleOcIt:r1o0n.1i0c3-s9t/rCu9cCtCu0r9e701inE
metals (< 50 ppm) are too low to be involved in catalysis.9 carbon materials, giving rise to serious structural distortions as
Therefore, the sharp contrast between B-CNDs and p-G in well.3-7 The distortion degree of the graphene-like material
catalytic activity can be ascribed to B-incorporation in the structure is closely related to the polarization and the
carbon materials.
distribution of electrostatic potential, or depends on the
The significance of B doping for the catalytic performance of atomic charge distribution of the materials. Increasing the
B-CNDs was further investigated via a control experiment for distortion degree of a material does not linearly increase the
fabricating boron doped graphene materials (B-CNDs-g) with exposure of edge defective sites, due to a lower utilization of
various contents of B species as catalysts for acetylene these sites resulting from aggregation induced by distortion in
hydrochlorination. The B-CNDs-g series materials were a 2D material.9-14 The aggregation and collapse of 2D carbon
prepared via a substitution reaction through carbonization of materials during application have attracted wide concern,
mixed graphene and B2O3 (Figure S5, Table S4).12 In B-CNDs-g1 especially the advanced heteroatoms-doped defective
materials, the total -BC3 content decreases to 53.5 at. %, which materials (e.g. g-C3N4, C2N). Interestingly, B-CNDs exhibit a
is still the dominant B configuration (Figures 2c), while -BC2O high defective level and uneven atomic charge distribution,
increases to 33.8% and -BCO2 decreases to 12.7%. The -BC3 but a relatively low dipole moment and thus a low-level
content is further reduced to 36.7 at. %, while -BC2O and -BCO2 distortion, which may ascribe to the special distribution of
increase to 42.5 at. % and 20.8 at. %, respectively in B-CNDs- electrostatic potential over the surface of B-CNDs. Compared
g2. In B-CNDs-g3, -BC2O (44.6 at. %) is the dominant B with most edge doping 2D carbon materials, the nanodots in
configuration, while -BC3 and -BCO2 are calculated by the curve B-CNDs were dispersed in a graphene layered matrix, enabling
fitted areas as 30.2 at. % and 25.2 at. %, respectively. These an inhomogeneous distribution of local electrostatic potential
materials exhibit analogous substitutional B contents and over nanodots, but a symmetrical distribution of electrostatic
defect levels (Figure S6, Table S5), minimizing the quantity potential over the entire material surface. This achieved the
changes in of defect sites on catalytic performance. The effective combination of overall physical structure stability and
activity of B-CNDs toward acetylene hydrochlorination is local electronic structure defect of graphite-like catalysts.
strongly correlated with the contents of different
B
Moreover, the inhomogeneous distribution of local
configurations, with a more linear relationship of acetylene electrostatic potential over B-CNDs leads to enhanced surface
conversion with -BC3 content (Figure 2c) than with -BC2O or - adsorption and activation toward substrates relative to the
BCO2, suggesting that -BC3 is the most active B site, albeit the pure carbon surface, which can be well supported by the
influence from the C-B-O species cannot be entirely ruled out.
electron affinity and substrate adsorption energy results
We calculated the space time yield (STY) of B-CNDs and (Figure S9). Affinity to substrates can be generated in the
normalized it to the unit loading (kg) of catalyst, for it can provide
the original catalytic property and production capacity of catalysts.
STY results for VCM calculated from experimental data are
a)
3
2
1
summarized in Figure 2d and Table S6. The ionic liquids-derived B-
CNDs catalyst shows a relatively high STY. The value is calculated to
0
푘푔푉퐶푀 푘푔 ―1
ℎ
―1
p-G
g-B
BC2O
BCO2
BC3
be 1.19
for B-CNDs (Figure 2d, Table S6), which is
퐶푎푡.
b) 0
comparable to that of the state-of-the-art metal-free catalysts, and
73.30
67.45
-20
-40
-60
-80
C2H2
adsorption
furnishes higher STY than the vast majority of Au- and Pd-based
45.60
36.10
2f,4f
catalysts for acetylene hydrochlorination
.
p-G
g-B
BC2O
BCO2
BC3
The electron properties and catalytic mechanism involved in
acetylene hydrochlorination over B-CNDs were investigated by
DFT calculations on different B-containing sites (Figure S7).
Similar B site models have been previously adopted to
demonstrate the effectiveness of heteroatom doped-carbon
materials.13 Figure 3a and Figure S8 show the electrostatic
potential mappings of various surface models. Notably, when
compared with the p-G surface, all the B-doped carbon
surfaces exhibit uneven electrostatic potentials, suggesting the
uneven surface atomic charge distribution might result from
doping, which has been reported by Sun et al.7c The increased
uneven distribution of surface atomic charge could cause
electronic structure defect, leading to enhanced surface
adsorption and activation toward substrates, due to
electrostatic potential difference and improved polarization
thereof, as evidenced by dipole moments and adsorption
energies to substrates (Figure 3a and 3b). However,
23.47
VCM
desorption
HCl
insertion
VCM
formation
Reaction progress
Figure 3 a) The dipole moments of p-G and four surfaces doped with g-B, BC3,
BC2O and BCO2 species, respectively. Insertion: Electrostatic potential
mappings of various surface models. b) The calculated energy profile of the
reaction pathways employing the five different active sites.
interaction of electron-deficient boron centers and bonded
carbon atoms, thus providing potential for adsorption and
activation toward substrates.4-7,9 Under the condition of
stronger binding energy of C2H2 than HCl, the reaction starts
with the adsorption of C2H2. Figure 3b and S10 displays the
calculated elementary steps of interest involved in the
acetylene hydrochlorination process. The C2H2 tends to
interact with electroneutral C atom in pure carbon surface
with an adsorption energy of -35.33 kJ mol-1. By contrast, B
atom incorporation into carbon plane with the -BC3 structure
leads to larger positive charges and stronger interaction with
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J. Name., 2013, 00, 1-3 | 3
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C2H2 (Eads = -46.7 kJ mol-1) than pure carbon surface, -BC2O
(Eads = -37.34 kJ mol-1) and -BCO2 (Eads = -37.56 kJ mol-1) sites.
Subsequently, the further insertion and adsorption of HCl
molecule on B sites with a similar adsorption energy of ~-70 kJ
mol-1, activates C2H2 on -BC3 sites coordinates with HCl to form
VCM with the lowest energy barrier of 23.47 kJ mol-1 among
the five surfaces, suggesting that the -BC3 site, without
coordination with O atoms, is active. The formation of VCM
should be the rate determining step. In the experiment, the
active site -BC3 did exhibit better catalytic performance,
demonstrating the qualitative agreement between experiment
and computational models.
In conclusion, we have synthesized 2D layered B-CNDs with
in-plane dispersed BC3-nanodots through preassembly of ionic
liquids precursors and carbonization. The obtained B-CNDs
possess an inhomogeneous distribution of local electrostatic
potential over nanodots but a symmetrical distribution over
the entire surface, thus facilitating high distortion resistance
while maintaining chemical activity. The synthesized B-CNDs
have been applied in acetylene hydrochlorination with
excellent catalytic performance and high durability. The
method presented herein provides a universal procedure for
generating 2D carbon materials with an advanced structure for
a wide range of applications.
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Conflicts of interest
There are no conflicts to declare.
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