Synthesis of 1,10-decanediol diacetate and 1-decanol acetate from furfural

Article abstract of DOI:10.1039/d1gc00227a

A green and efficient method was developed for upgrading furfural to 1,10-decanediol diacetate and 1-decanol acetate. 92% yield of the acetates was obtained through the tandem benzoin condensation and hydrodeoxygenation reaction. During the benzoin condensation, furfural was catalyzed into furoin in a quantitative yield by the immobilized NHC catalyst under solvent-free conditions. After dissolving the furoin intermediate in acetic acid, the Sc(OTf)₃and Pd/C catalytic system was introduced for hydrodeoxygenation. The effects of reaction factors have been investigated in detail and the hydrodeoxygenation process has been explored by¹H-NMR and GC-MS.

Full text of DOI:10.1039/d1gc00227a

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Synthesis of 1,10-decanediol diacetate and
1-decanol acetate from furfural†
Cite this: Green Chem., 2021, 23,
2169
Chen-Qiang Deng, Qin-Zhu Jiang, Jin Deng * and Yao Fu
*
A green and efficient method was developed for upgrading furfural to 1,10-decanediol diacetate and
1-decanol acetate. 92% yield of the acetates was obtained through the tandem benzoin condensation
and hydrodeoxygenation reaction. During the benzoin condensation, furfural was catalyzed into furoin in
a quantitative yield by the immobilized NHC catalyst under solvent-free conditions. After dissolving the
furoin intermediate in acetic acid, the Sc(OTf)3 and Pd/C catalytic system was introduced for hydrodeoxy-
genation. The effects of reaction factors have been investigated in detail and the hydrodeoxygenation
process has been explored by 1H-NMR and GC-MS.
Received 20th January 2021,
Accepted 19th February 2021
DOI: 10.1039/d1gc00227a
rsc.li/greenchem
adiene to obtain alkyl aluminum intermediates through the
hydrogen transfer and hydroalumination reaction. Then, 1,10-
Introduction
The greenhouse effect and air pollution caused by the exces- decanediol and 1-decanol were obtained in NaOH under an
sive consumption of fossil resources have led researchers to oxygen atmosphere. In 2013, Peng et al.17 reported the use of
explore various forms of renewable resources.1 As a promising 5-bromo-1-pentanol to synthesize 1,10-decanediol by the
alternative to traditional fossil resources, the abundant ligno- nickel-catalyzed reductive coupling reaction. However, these
cellulosic biomass resource is the only renewable organic methods have many disadvantages, such as the limitation of
carbon source.2 Furfural, mainly produced from hemicellulose raw materials, a large number of catalysts, and environmental
in lignocellulose, is one of the most valuable biomass platform pollution, and could not meet the requirements of green
molecules with an annual global production of 100 kton.3 So chemistry. Herein, we describe the synthesis of 1,10-decane-
far, furfural has been developed to convert into many impor- diol diacetate and 1-decanol acetate from biomass-derived fur-
tant chemicals, such as furfuryl alcohol,4 levulinic acid,5 cyclo- fural through a tandem reaction (Scheme 1).
pentanone,6 pentanediol,7 and 2-methyl tetrahydrofuran.8
Therefore, it is of great significance to explore the conversion fural and 1,10-decanediol diacetate, we designed a new syn-
To establish the tandem reaction relationship between fur-
of furfural into high value-added chemicals.
thetic route based on retrosynthetic analysis (Scheme 2). 1,10-
As an important raw material, 1,10-decanediol is used for
the synthesis of surfactants9 and ester lubricants10 in the fine
chemicals industry, as well as the production of diiododecane,
an important pharmaceutical intermediate.11 Moreover, 1,10-
decanediol can be used for the synthesis of membrane
materials,12 heat storage materials,13 and various polymer
materials.14 The current industrial production of 1,10-decane-
diol is obtained by the reduction of sebacic acid (obtained
from the oxidation of castor oil) or its esters by using lithium
aluminum hydride, sodium borohydride, or other metal-redu-
cing agents.15 In 2001, Gagneur et al.16 reported the use of dec-
Hefei National Laboratory for Physical Sciences at the Microscale, iChEM, CAS Key
laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass
Clean Energy, Department of Chemistry, University of Science and Technology of
China, Hefei, Anhui 230026, China. E-mail: dengjin@ustc.edu.cn,
fuyao@ustc.edu.cn
†Electronic supplementary information (ESI) available. See DOI: 10.1039/
d1gc00227a
Scheme 1 Synthesis of 1,10-decanediol/1-decanol and their acetates.
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Scheme 2 The retrosynthetic analysis of 1,10-decanediol diacetate obtained from furfural.
Decanediol diacetate can be obtained by ring-opening and on the product distribution were investigated by using furoin as
selective hydrogenolysis of 1,2-bis(2-tetrahydrofuryl)ethane, a substrate in an acetic acid system (Table 1). The Lewis acidity
which can be easily obtained by hydrogenation saturation of of the metal triflate was positively correlated with the charge
1,2-bis(furan-2-yl)ethane. Obviously, the skeleton structure of density on the metal ionic radius.20 Considering that stronger
1,2-bis(2-tetrahydrofuryl)ethane is highly similar to furoin. Lewis acidity was beneficial to promote the ring-opening of the
Furoin can be readily prepared from biomass-derived furfural cyclic ether, Hf(OTf)4 and Al(OTf)3 were preferentially used for
through a benzoin condensation reaction. As a powerful cata- the hydrodeoxygenation reaction (entries 1 and 2). Compound 1
lyst for benzoin condensation, the NHC catalyst was intro- was obtained with a yield of 65% and 62%, respectively. On
duced for the first step.18 On the other hand, because metal using the medium Lewis acidity of Sc(OTf)3, 66% yield of 1 was
triflates can promote the ring-opening of the cyclic ether and obtained and the total yield was up to 98%. It was demonstrated
Pd/C can achieve the hydrogenation of unsaturated double that Sc(OTf)3 could effectively activate the ester group and
bonds,19 the Lewis acids and hydrogenation catalytic system promote the ring-opening of the cyclic ether. However, when the
were introduced for the second step. Therefore, the challenges Lewis acidity was further reduced, such as Cu(OTf)2, the total
of establishing this method are: (a) controlling the selectivity yield was drastically decreased to 46% (entry 5). Inspired by
and sequentiality of hydrodeoxygenation (step 2) and (b) Chen et al.21 who reported the preparation of C10–C12 alkanes
achieving the compatibility of benzoin condensation (step 1) with the Pd/C and La(OTf)3 catalytic system, we also investigated
with the reaction pathway of step 2, to realize the synthesis of lanthanide metal triflates for this reaction (entries 6–16).
C
10 alcohol esters from biomass-derived furfural.
Unfortunately, none of the lanthanide triflates showed better
catalytic activity than Sc(OTf)3. The relationship between the
product distribution and the charge density was not clear. This
may be due to the fact that the hydrodeoxygenation reaction is a
multi-step series coupling reaction (including the ring-opening
of cyclic ethers and the cleavage of esters), which might be
affected by many factors simultaneously.
Results and discussion
Initially, in response to the challenge of selectivity and sequenti-
ality of hydrodeoxygenation (step 2), the effects of metal triflates
Table 1 The screening of metal triflates in hydrodeoxygenation of furoin
Yield/%
Entry
Metal triflate
Ionic radius
Charge density
Conversion/%
1
2
3
Others
1
2
3
4
5
6
7
8
Hf(OTf)4
Al(OTf)3
Sc(OTf)3
Ni(OTf)2
Cu(OTf)2
Sm(OTf)3
Ce(OTf)3
La(OTf)3
Yb(OTf)3
Y(OTf)3
Lu(OTf)3
Pr(OTf)3
Gd(OTf)3
Ho(OTf)3
Er(OTf)3
Dy(OTf)3
0.71
5.63
5.61
4.03
2.90
2.74
3.13
2.97
2.91
3.46
3.33
3.48
3.03
3.20
3.33
3.37
3.29
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
65
62
66
55
36
58
60
52
50
44
61
54
50
43
40
44
28
30
29
16
10
22
21
19
24
17
22
18
13
18
15
15
2
3
3
1
0
1
1
1
2
0
0
1
1
1
0
0
5
5
2
0.535
0.745
0.69
0.73
0.958
1.01
1.032
0.868
0.900
0.861
0.99
0.938
0.901
0.89
28
54
19
18
28
24
39
17
27
36
38
45
41
9
10
11
12
13
14
15
16
0.912
Reaction conditions: furoin (0.5 mmol), metal triflate (4 mol%), 10% Pd/C (3 mol%), H2 (3 MPa), acetic acid (10 mL), 180 °C and 6 h. 1: 1,10-
decanediol diacetate; 2: 1-decanol acetate; 3: decane; others: including the intermediate product and the product that cannot be detected.
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the hydrogenation catalyst.22 However, the 5% Ru/C and 5%
Rh/C catalysts exhibited relatively weak hydrogenation catalytic
activity. Because Ru and Rh had a wide metal d band, the
repulsion between the metal surface electron and the CvC
bond went against the adsorption of the Ru/C or Rh/C
catalyst.23
After studying the effect of the hydrogenation catalyst on
the reaction, we investigated the effect of the hydrogen
pressure on the reaction process (Fig. 3). At low hydrogen
pressure (1 MPa H2), 66% yield of 1 and 2 was obtained. With
the increase of the hydrogen pressure, the yield of 1 and 2
increased significantly. When the hydrogen pressure reached 3
MPa, 1 and 2 were obtained in 95% yield. However, when the
hydrogen pressure further increased from 3 MPa to 4 MPa, the
yield of 1 decreased gradually from 66% to 56% and the yield
of 2 increased from 28% to 35%. This indicated that high
pressure negatively affected the selectivity of compound 1.
Marks and co-workers20 reported that the cracking ability of
acetate was related to the stability of the carbocation in the
reaction process. The trend for the cleavage of acetate was: ter-
tiary > second > primary. The secondary ester was easier to
cleave than the primary ester, so 1 was mainly obtained in the
catalytic system. When the hydrogen pressure was too high,
the C–O bond of the terminal ester was cleaved. Hence, the
optimal hydrogen pressure was 3 MPa.
Next, the effect of the reaction time on the product distri-
bution was explored (Fig. 4). Initially, the reaction mixture was
heated to 180 °C for 30 min. Then, it was maintained at 180 °C
for a certain time until the reaction was complete. When the
reaction mixture was maintained at 180 °C for 30 min, the
yields of 1 and 2 were 58% and 20%, respectively. Meanwhile,
a small amount of 3 was also detected. This showed that the
conversion of the raw material was very fast and Sc(OTf)3 was
an excellent catalyst for the ring-opening of the cyclic ether.
With the extension of the reaction time, reaction intermediates
gradually decreased, and the total yield of 1 and 2 increased
smoothly. When the reaction time was 6 h, the reaction inter-
mediate was almost converted and 95% yield of 1 and 2 was
obtained. When the reaction time was extended to 8 h, the
yield of 1 decreased slightly, while the yield of 2 and 3
increased further. Overall, the optimal reaction time was 6 h.
Fig. 1 Effect of the reaction temperature. Reaction conditions: furoin
(0.5 mmol), metal triflate (4 mol%), 10% Pd/C (3 mol%), H2 (3 MPa),
acetic acid (10 mL) and 6 h. 1: 1,10-decanediol diacetate; 2: 1-decanol
acetate; 3: decane; and 4: including the intermediate product and the
product that cannot be detected.
The reaction temperature was an important factor that
affected the ring-opening of cyclic ethers and the cleavage of
ester groups. Therefore, the effect of the reaction temperature
on the product distribution was investigated (Fig. 1). When the
reaction temperature was 120 °C, a lot of hydrogenated inter-
mediates were formed. 13% yield of 1 and 2 was obtained,
while 3 was not formed. When the reaction temperature was
increased to 160 °C, the hydrogenated intermediate sharply
decreased. The yield of 1 and 2 significantly increased to 80%.
Meanwhile, a small amount of 3 was detected. The activity of
the catalyst increased with the increase of the reaction temp-
erature. When the reaction temperature was 180 °C, a total
yield of 98% was obtained. The yield of 1 and 2 increased to
95%. However, when the reaction temperature further
increased to 200 °C, the yield of 1 decreased from 66% to 52%,
and the yield of 2 increased to 41%. Such results indicated
that an excessively high reaction temperature could cause the
cleavage of the C–O bonds of 1. Therefore, the appropriate
reaction temperature had an important influence on the selec-
tive cleavage of the C–O bonds.
On the other hand, the influence of the hydrogenation cata-
lyst on the hydrodeoxygenation reaction was also investigated
(Fig. 2). The 10% Pd/C and 5% Pt/C catalysts had high hydro-
genation catalytic activity. Metal triflates could activate the
ester group to form a CvC bond which was then saturated by
Fig. 2 Effect of the hydrogenation catalyst. Reaction conditions: furoin
(0.5 mmol), Sc(OTf)3 (4 mol%), hydrogenation catalyst (3 mol%), acetic
acid (10 mL), H2 (3 MPa), 180 °C and 6 h. 1: 1,10-decanediol diacetate, 2:
1-decanol acetate, and 3: decane.
Fig. 3 Effect of the hydrogen pressure. Reaction conditions: furoin
(0.5 mmol), Sc(OTf)3 (4 mol%), 10% Pd/C (3 mol%), acetic acid (10 mL),
180 °C and 6 h. 1: 1,10-decanediol diacetate, 2: 1-decanol acetate, and
3: decane.
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Because the catalytic system consisted of the Lewis acid
catalyst and the hydrogenation catalyst, the ratio of Sc(OTf)3
and Pd/C was investigated (Fig. 5). When Sc(OTf)3 or Pd/C was
used alone, the target product was not obtained. These results
indicated that the reaction can only be carried out with both
Lewis acid and hydrogenation catalyst. When the catalyst ratio
was 4 : 1 (mol%), 79% total yield was obtained. This result
revealed that there was a synergistic effect between Pd/C and
Sc(OTf)3. When the catalyst ratio was changed from 4 : 1 to 4 : 3
(mol%), the yield of 1 and 2 significantly increased to 95%.
When the catalyst ratio was 4 : 4 (mol%), the yield of 1
decreased slightly, while the yield of 2 and 3 increased further.
This indicated that excessive Pd/C would cause over-hydroge-
nolysis of the C–O bonds of 1. Therefore, the optimal catalyst
ratio (Sc(OTf)3/Pd/C) was 4 : 3 (mol%).
Fig. 4 Effect of the reaction time. Reaction conditions: furoin (0.5 mmol),
Sc(OTf)3 (4 mol%), 10% Pd/C (3 mol%), acetic acid (10 mL), H2 (3 MPa) and
180 °C. 1: 1,10-decanediol diacetate, 2: 1-decanol acetate, 3: decane, and 4:
including the intermediate product and the product that cannot be detected.
1
To further understand the reaction process, H-NMR spec-
troscopy was performed to monitor the reaction (Fig. 6). The
reaction solution with different heating times was character-
1
ized by H-NMR. The characteristic peaks of the intermediate
1,2-bis(tetrahydrofuran-2-yl)ethane (δ 3.7 ppm) and the
product (δ 4.1 ppm, 2.1 ppm, and 0.9 ppm) were observed
when heating for 10 min. Meanwhile, the characteristic peaks
of the raw material disappeared completely. This indicated
that the furan ring was easily hydrogenated during the reac-
tion. With the extension of the heating time, the reaction inter-
mediates gradually decreased. When the reaction solution was
heated for 30 min and maintained for 30 min, the character-
Fig. 5 Effect of the catalyst ratio. Reaction conditions: furoin
(0.5 mmol), acetic acid (10 mL), H2 (3 MPa), 180 °C and 6 h. 1: 1,10-
decanediol diacetate, 2: 1-decanol acetate, and 3: decane.
Fig. 6 1H NMR spectra of the reaction solution at different reaction times.
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Scheme 3 Proposed reaction mechanism.
istic peak of 1,2-bis(tetrahydrofuran-2-yl)ethane disappeared. CvO bond of intermediate b preceded the ring-opening of the
Because the characteristic peaks of other intermediates over- cyclic ether. Subsequently, the ester group of intermediate c
lapped with those of the product, they could not be distin- was cleaved by Pd/C. Then, intermediate d underwent ring-
1
guished by H-NMR. To solve this problem, we used GC-MS to opening via metal triflates to obtain intermediate e. Finally,
detect the reaction solution heated for 10 min (see the ESI† for the target product was obtained by the ring-opening of the
details). The GC-MS result showed that the reaction solution cyclic ether and hydrogenolysis.
had three intermediates: 1,2-bis(tetrahydrofuran-2-yl)ethyl
According to Scheme 3, intermediate e could generate f and
acetate, 1,2-bis(tetrahydrofuran-2-yl)ethane, and 6-(tetrahydro- 1 simultaneously. The ring-opening of intermediate f was pro-
furan-2-yl)hexyl acetate. Based on the above investigation, we moted by metal triflates to obtain 2. However, 1 could also be
proposed a possible reaction mechanism (Scheme 3). To over-hydrogenated to form 2. An attempt was made to optimize
further verify the reaction pathway, we designed several poss- the reaction conditions to improve the selectivity of the reac-
ible intermediates for the experiment. The results are shown tion, but the result was unsatisfactory. The ratio of products 1
in Table 2. On using 1,2-bis(furan-2-yl)ethane-1,2-diol as the to 2 was about 2 : 1 under the optimal reaction conditions. It
substrate, the target product could not be obtained under stan- may be that the formation of f and 1 was a parallel reaction,
dard reaction conditions (Table 2, entry 2). The reason might resulting in low selectivity. Although the selectivity of the reac-
be that two adjacent hydroxyl groups would coordinate with Sc tion was not high, the physical properties of products 1 and 2
(OTf)3, which could not promote the ring-opening of the cyclic were quite different. The boiling point difference between 1 (b.
ether. However, on using 1,2-di(furan-2-yl)ethan-1-one as the p. 136 °C at 3 mmHg)24 and 2 (b.p. 87 °C at 3 mmHg)25 was
substrate, the target product was obtained in 89% yield about 50 °C. Thus, products 1 and 2 could be separated
(Table 2, entry 3). Such results indicated that the hydroxyl through vacuum distillation. The catalytic system has a high
group of furoin was preferentially removed instead of the CvO application value for the conversion of furfural into fine
bond being reduced. When intermediate d was used as the chemicals.
substrate, 92% yield of the target product was obtained
To test the stability of the Pd/C catalyst, a recycling experi-
(Table 2, entry 4). This indicated that the reduction of the ment was conducted. Biphenyl was added to the reaction solu-
tion for quantitative product analysis. The reaction mixture
was centrifuged to collect Pd/C, which was then dried and
used for the next cycle. Fig. 7 shows the results of the Pd/C re-
cycling experiment. The catalytic activity decreased slightly
Table 2 Possible intermediates as substrates used to verify the reaction
pathway
Yield/%
Entry
1
Substrate
1
2
3
Total
98
66
29
3
2
4
1
0
5
3
4
57
52
32
40
3
5
92
97
Reaction conditions: furoin (0.5 mmol), metal triflate (4 mol%), 10%
Pd/C (3 mol%), H2 (3 MPa), acetic acid (10 mL), 180 °C and 6 h. 1:
1,10-decanediol diacetate; 2: 1-decanol acetate; 3: decane; total: sum of
1, 2, and 3.
Fig. 7 Recycling study. Reaction conditions: furoin (0.5 mmol), Sc
(OTf)3 (4 mol%), acetic acid (10 mL), H2 (3 MPa), 180 °C and 6 h. 1: 1,10-
decanediol diacetate, 2: 1-decanol acetate, and 3: decane.
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after three cycles. The Pd/C catalyst certainly showed stability.
However, the catalytic activity of the Pd/C catalyst decreased
sharply at the fifth run. We analyzed the used Pd/C after 5
cycles by transmission electron microscopy (TEM) characteriz-
ation. The used Pd/C was partially agglomerated in contrast
with the fresh Pd/C (see the ESI† for details). This indicated
that the decrease of catalytic activity was connected with the
formation of Pd agglomerates on the Pd/C catalyst.19 Besides,
the loss and oxidation of the catalyst during the recovery
process in the air also contributed to a decrease in the yield.
After completing the optimization of step 2, for the benzoin
condensation (step 1), we decided to use a green NHC catalyst
with high catalytic activity. However, the NHC catalyst usually
needs to be converted into an active carbene form by alkaline
reagents, and the carbene form is unstable and easily destroyed
in the air. What was more difficult was that because the sub-
sequent hydrodeoxygenation (step 2) was carried out in acetic
acid, the reaction conditions of the sequential two steps were
incompatible. To achieve the compatibility of the two steps, the
strategies including solvent-free reaction conditions and catalyst
immobilization were applied in step 1. Consequently, at the end
of step 1, the furoin product could be dissolved in acetic acid to
obtain the reaction solution of step 2. Meanwhile, the NHC cata-
lyst could be recovered and transformed from unstable carbene
into stable acetate. Based on the above assumption, a one-pot,
two-step tandem method was established to prepare 1,10-decan-
ediol and 1-decanol acetates from furfural.
Fig. 8 Reused times of the imidazole-type immobilized NHC catalyst.
target product was not obtained. We speculated that the thia-
zole-type immobilized NHC catalyst containing the S element
may poison the Pd/C catalyst. To prove this speculation, we
used commercially available furoin as the substrate. 0.1 mol%
thiazole-type non-immobilized NHC catalyst was added to the
reaction system and the hydrodeoxygenation reaction was
carried out under standard conditions (Table 3, entry 2).
Similarly, the target product was not obtained. The result was
consistent with our speculation. Therefore, we considered
using an imidazole-type immobilized NHC catalyst for step 1.
The preparation of the imidazole-type immobilized NHC cata-
lyst was performed by immobilizing 1-undecyl-1H-benzo[d]
imidazole on Merrifield resin. 0.5 mol% imidazole-type
immobilized NHC catalyst achieved almost full condensation
of furfural to furoin under solvent-free conditions. The hydro-
deoxygenation reaction was then carried out under standard
conditions (Table 3, entry 4). 92% yield of the target product
was obtained, which was consistent with commercially avail-
able furoin as the substrate (Table 3, entry 3). These results
confirmed that the S element in the thiazole-type immobilized
NHC catalyst could cause the deactivation of the Pd/C catalyst.
Finally, the reusability of the immobilized NHC catalyst was
tested. Both types of immobilized NHC catalysts had high cata-
lytic activity and stability. The activity of the catalyst did not
decrease after 10 cycles (Fig. 8 and Fig. S2†). In short, tandem
benzoin condensation (step 1) and hydrodeoxygenation (step
2) realized the synthesis of 1,10-decanediol diacetate and
1-decanol acetate from biomass-derived furfural.
Initially, inspired by the vitamin B1 catalyst, we prepared a
thiazole-type immobilized NHC catalyst by immobilizing 2-(4-
methylthiazol-5-yl)ethan-1-ol on Merrifield resin to catalyze
benzoin condensation. 0.5 mol% thiazole-type immobilized
NHC catalyzed furfural condensation to obtain furoin in 98%
yield under solvent-free conditions. Subsequently, acetic acid
was added to the product. The acetic acid solution was filtered
to remove the thiazole-type immobilized NHC catalyst, and
then the hydrodeoxygenation reaction was carried out under
standard conditions (Table 3, entry 1). Unfortunately, the
Table 3 Furoin from different sources for the hydrodeoxygenation
reactiona
Yield/%
Entry
1
NHC catalyst
Substrate
Furoinb
1
2
3
Total
3
Conclusions
3
0
0
In summary, the synthesis of 1,10-decanediol diacetate and
1-decanol acetate was achieved from biomass-derived furfural
through benzoin condensation to obtain furoin under solvent-
free conditions with the immobilized NHC catalyst followed by
selective hydrodeoxygenation with the Sc(OTf)3 and Pd/C co-
catalytic system in acetic acid. This method realized the con-
version of biomass-derived molecules into high value-added
chemicals. Up to 92% yield of 1,10-decanediol and 1-decanol
acetates was obtained by the tandem benzoin condensation
and hydrodeoxygenation reaction. The immobilized NHC cata-
lysts have high catalytic activity and stability. This tandem reac-
2
Furoinc
2
0
0
2
3
4
—
Furoinc
Furoinb
66
65
29
27
3
2
98
94
a 0.5 mol% NHC catalyst (entries 1 and 4) and 0.1 mol% NHC catalyst
(entry 2). b Furoin was prepared from furfural with the NHC catalyst.
c Commercially available furoin. 1: 1,10-decanediol diacetate; 2:
1-decanol acetate; 3: decane; total: sum of 1, 2, and 3.
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Author contributions
Chen-Qiang Deng: data curation, investigation, formal ana-
lysis, and writing – original draft; Qin-Zhu Jiang: investigation
and writing – original draft; Yao Fu: resources and supervision;
Jin Deng: conceptualization, methodology, project adminis-
tration, resources, supervision, and writing – review and
editing.
Conflicts of interest
8 (a) F. Dong, Y. L. Zhu, G. Q. Ding, J. L. Cui, X. Q. Li and
Y. W. Li, ChemSusChem, 2015, 8, 1534–1537;
(b) J. G. Stevens, R. A. Bourne, M. V. Twigg and
M. Poliakoff, Angew. Chem., Int. Ed., 2010, 49, 8856–8859;
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There are no conflicts to declare.
Acknowledgements
This work was financially supported by the National Key R&D
Program of China (2018YFB1501502), the National Natural
Science Foundation of China (21875239), and the
Fundamental Research Funds for the Central Universities
(WK3530000004). The authors thank Hefei Leaf Biotech Co.,
Ltd and Anhui Kemi Machinery Technology Co., Ltd for free
samples and equipment that benefited their ability to conduct
this study.
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