Synthesis of 5-hydroxymethylfurfural from monosaccharides catalyzed by superacid VNU-11-SO4in 1-ethyl-3-methylimidazolium chloride ionic liquid

Article abstract of DOI:10.1039/d0ra08261a

Superacid VNU-11-SO4, a modified metal-organic framework by post-synthetic treatment with a sulfuric acid solution, has been considered as a promising heterogeneous catalyst in the isomerization of glucose to fructose and further dehydration to form 5-hydroxymethylfurfural (HMF) due to its possession of both Lewis and Br?nsted acid sites. In this work, we focused on using VNU-11-SO4 for the optimization of the conversion of fructose and glucose into HMF using an ionic liquid as a green solvent. The highest yields of HMF from glucose and fructose could be obtained in 28% (140 °C, 8 h) and 86% (110 °C, 3 h), respectively, with the use of VNU-11-SO4 catalyst in 1-ethyl-3-methylimidazolium chloride ionic liquid. Recycling examination of the catalyst showed only a slight decrease in the HMF yield, implying its potential industrial application in biomass transformation.

Full text of DOI:10.1039/d0ra08261a

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PAPER
Synthesis of 5-hydroxymethylfurfural from
monosaccharides catalyzed by superacid VNU-11–
SO4 in 1-ethyl-3-methylimidazolium chloride ionic
liquid†
Cite this: RSC Adv., 2020, 10, 39687
Linh Ho Thuy Nguyen,‡abc Huong Thi Vo,‡ac Ha Bich Phan,‡abd Minh Huy Dinh
bc
ac
Dang,abc Tan Le Hoang Doan
and Phuong Hoang Tran
*
*
Superacid VNU-11–SO4, a modified metal–organic framework by post-synthetic treatment with a sulfuric
acid solution, has been considered as a promising heterogeneous catalyst in the isomerization of glucose to
fructose and further dehydration to form 5-hydroxymethylfurfural (HMF) due to its possession of both Lewis
and Brønsted acid sites. In this work, we focused on using VNU-11–SO4 for the optimization of the
conversion of fructose and glucose into HMF using an ionic liquid as a green solvent. The highest yields
of HMF from glucose and fructose could be obtained in 28% (140 ꢀC, 8 h) and 86% (110 ꢀC, 3 h),
respectively, with the use of VNU-11–SO4 catalyst in 1-ethyl-3-methylimidazolium chloride ionic liquid.
Recycling examination of the catalyst showed only a slight decrease in the HMF yield, implying its
potential industrial application in biomass transformation.
Received 27th September 2020
Accepted 19th October 2020
DOI: 10.1039/d0ra08261a
rsc.li/rsc-advances
dissolution of sugar.16,17 Among these, ILs and DES are
becoming increasingly important due to the unique properties
related to design exible structure and reusability.16,18–20
1. Introduction
5-Hydroxymethylfurfural is a useful furan ring that can produce
an important intermediate to biofuels and commodity chem-
icals.1–3 In recent years, the preparation of HMF from carbohy-
drates has been extensively studied. Generally, HMF is mainly
produced via dehydration reactions of monosaccharides using
homogeneous (e.g., H2SO4, HCl, AlCl3, and CrCl3) or heteroge-
neous catalysts (e.g., zirconium oxide, zeolites, metal–organic
frameworks) in a biphasic system.3–10 Although the homoge-
neous acidic catalysts are efficient in the process,11 some
methods suffer from intrinsic drawbacks, e.g., an expensive
catalyst with high loading, long reaction time, low yield, diffi-
culty in the recovery of catalyst, and toxic reactants. The
heterogeneous catalysts prove prominent advantages of stability
and reusability promising as potential alternatives.12–15 Besides,
water, dimethylsulfoxide (DMSO), N,N-dimethylformamide
(DMF), N,N-dimethylacetamide (DMA), N-methyl pyrrolidone
(NMP), acetonitrile, ionic liquids (ILs), deep eutectic (DES) and
biphasic systems have proven as suitable solvents for the
Metal–organic frameworks (MOFs) are attracted consider-
able interest in porous crystalline materials composed of
organic ligands and inorganic metal clusters. These materials
have been received with widespread attention for several elds,
including gas storage and separation,21,22 catalysis,23,24
sensing,25,26 drug delivery,27,28 proton, and ion conduction.29,30
With the prominent features such as low density, the large pore
sizes, and thermal stability, MOFs have recently appeared as
ability heterogeneous catalytic for organic transformations.31,32
In HMF production, the materials had multi-utility catalytic
simultaneously shown better activity and selectivity for the
isomerization/dehydration of glucose, in particular, Lewis
acidity, Brønsted acidity, and uniform structured nanoscale
cavities in MOF could be readily introduced for biomass
conversion.33–37 Sulfated MOF-808 and VNU-11 were known as
the rst superacid MOF on Zr- and Hf-MOF by anchoring sulfate
groups onto the metal clusters of secondary building units. The
coexisting Brønsted and Lewis acidities in superacid MOF were
also capable of catalyzing reaction, including Friedel–Cras
acylation, esterication, isomerization, and heterocycliza-
tion.38,39 The reaction proceeded smoothly and afforded the
expected product in high yield in the presence of superacid
MOF and ionic liquid under mild condition.
aDepartment of Organic Chemistry, Faculty of Chemistry, University of Science, Ho Chi
Minh City, 721337, Vietnam. E-mail: thphuong@hcmus.edu.vn
bCenter for Innovative Materials and Architectures (INOMAR), Ho Chi Minh City,
721337, Vietnam
cVietnam National University-Ho Chi Minh City, Ho Chi Minh City, 721337, Vietnam
dInstitute of Public Health, Ho Chi Minh City, 700000, Vietnam
† Electronic supplementary information (ESI) available. See DOI:
10.1039/d0ra08261a
Herein, we demonstrate a strategy using superacid VNU-11–
SO4 for the preparation of HMF from monosaccharides in ILs
(Scheme 1). The VNU-11–SO4 was proved to be an efficient
‡ These authors contributed equally.
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2.4. Catalytic study
In a typical experiment, glucose or fructose (1 mmol) was dis-
solved in [Emim]Cl (6 mmol), and then the VNU-11–SO4 catalyst
(20 mg) was added. The reaction mixture was heated in
a magnetic stirrer with an oil bath for 24 h. Samples were taken
from the reaction mixture at a period of time for HPLC analysis
to study the effect of catalyst, reaction times, and reaction
temperatures on the yield of the product. The isolation of HMF
from [Emim]Cl was performed by liquid–liquid extraction with
a mixture of ethyl acetate/diethyl ether. The structure of HMF
Scheme 1 The glucose conversion into HMF using superacid MOF in
ionic liquids.
catalyst for dehydration of glucose and fructose into HMF in 1-
ethyl-3-methylimidazolium chloride ([Emim]Cl). To the best of
our knowledge, this is the rst report of utilizing VNU-11–SO4 in
the conversion of monosaccharides to HMF in ionic liquids.
1
was characterized by H NMR and MS.
3. Results and discussion
3.1. Catalysts characterization of VNU-11–SO4
2. Experimental
2.1. Materials and instrumentations
The VNU-11 and VNU-11–SO4 were synthesized with a modi-
cation of the previous method and the detailed procedure re-
ported in ESI.†38 The Hf-MOFs were prepared via the reaction
between hafnium salt and H3BTC in N,N-dimethylformamide as
a solvent, and formic acid as a modulator. Aer the removal of
the guest molecules by evacuation at 150 ꢀC for 24 h, the
structure of the material was determined by PXRD patterns and
N2 sorption isotherms to conrm the successful activation and
phase purity of the materials (Fig. 1a and d). TGA measure-
ments were carried out for the VNU-11 pristine and VNU-11–SO4
sample under airow (Fig. 1b).
All chemicals were purchased commercial suppliers and used
without further purication. HPLC analyses were recorded on
Agilent Technologies 1260 Innity high-performance liquid
chromatography InertSustain C18 (4.6 ꢁ 150 mm) column, the
size of particles is 5 mm, equipped with a UV photodiode array
detector. For more details about chemicals and instruments,
please see in ESI.†
2.2. Preparation of VNU-11–SO4
The TGA curve of VNU-11 and VNU-11–SO4 showed two
distinct weight loss steps, corresponding to the evaporation of
organic solvents and water adsorbed on the surface (ꢂ3% and
10% for VNU-11 and VNU-11–SO4, respectively) and to the
decomposition of the framework (29.2% and 24.9% at 250–
VNU-11 and VNU-11–SO4 were synthesized from reported liter-
ature.34 A mixture of HfOCl2$8H2O (7.5 mmol, 3.10 g) and the
tricarboxylic acid H3BTC (2.5 mmol, 537 mg) in 320 mL solvent
mixture of DMF and formic acid (v/v ¼ 1 : 1) were added in
500 mL capped bottle and heated in an oven at 120 ꢀC for 3 days
under static conditions. Aer cooling the bottle to room
temperature, the precipitates were collected by centrifugation.
The products were washed with DMF, deionized water, and
anhydrous acetone separately 3 times for three days. Then, the
material was dried under reduced pressure at room tempera-
ture for 24 h and at 150 ꢀC for 24 h to collect activated VNU-11.
To obtain VNU-11–SO4, activated VNU-11 (200 mg, 0.109
mmol) was treated with 20 mL of H2SO4 0.1 M and for 24 h. Aer
24 h, the solid was centrifuged and washed with 60 mL deion-
ized water in 3 times per day for three days. Then, the sample
was washed quickly, exchanged with 100 mL anhydrous acetone
and immersed in 20 mL anhydrous chloroform for 3 days (3
times per day). Finally, VNU-11–SO4 was dried under reduced
pressure at room temperature for 24 h and at 150 ꢀC for 24 h to
collect activated VNU-11–SO4.
ꢀ
600 C for VNU-11 and VNU-11–SO4, respectively). The temper-
ature range of 600–800 ꢀC of the VNU-11–SO4 sample was shown
the decomposition of the anhydrous compound Hf(SO4)2 to give
the end product HfO2 of decomposition.41 In the range
2.3. Preparation of DESs
The deep eutectic solvents (DESs), a new type of ionic liquids,
including choline chloride/phenol (DES 1), choline chloride/
ethylene glycol (DES 2) were prepared through the procedure
reported in our previous literature.13,40 DESs were synthesized
easily by the formation of hydrogen bonding between phenol or
ethylene glycol with choline chloride (please see in Section 3,
ESI†).
Fig. 1 (a) PXRD patterns, (b) TGA curves, (c) FT-IR and (d) N2 isotherms
of VNU-11 (blue) and VNU-11–SO4 (red) samples. The filled and
opened symbols represent the adsorption and desorption processes,
respectively.
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ꢀ
temperature 600–700 C, the mass loss was 4.8%, which corre- 10). As seen in Table 1, the HMF was not detected in the absence
sponded to a release of SO2. This value was consistent with the of the catalyst (Table 1, entry 1). This can be seen that the strong
percentage of theoretical mass SO2 lost from VNU-11–(SO4)2.5 acidity of the SO3H group in superacid VNU-11–SO4 could
(4.2%).
promote for dehydration of fructose to achieve the high HMF
Fig. 1c shows the FT-IR spectra of the H3BTC, VNU-11, and yield and the catalytic system between [Emim]Cl and Hf-clusters
VNU-11–SO4 samples. The characteristic peaks in the range of could further an isomerization of glucose to fructose.
1610–552 cmꢃ1 in the VNU-11 spectrum were ascribed to C]O
Next, the inuence solvents on the HMF production were
vibrations (1610 cmꢃ1), C–O stretching (1400 cmꢃ1), and Zr–O tested, and the results were shown in Table 1. The investigation
modes (760 cmꢃ1). The presence of sulfonic groups in the VNU- indicated the highest HMF yield was obtained in [Emim]Cl
11–SO4 structure resulted in identical signals at approximately (Table 1, entries 4 and 7), which was higher than the results
1000 and 1050 cmꢃ1. The acidities of VNU-11–SO4 were char- achieved in DMSO (Table 1, entries 5 and 12). Deep eutectic
acterized by using the Hammett indicator test. The color change solvents, a new type of ionic liquids, were also tested as the
observed of VNU-11–SO4 in 2,4-dinitrouorobenzene as with solvents in the present method, but the low yields of HMF were
a value of Ho # ꢃ14.5 indicated a higher acidity than the observed by using DES 1 and DES 2 (Table 1, entries 13 and 14).
original VNU-11 as well as sulfuric acid (Ho ¼ ꢃ12).
The reaction did not proceed in the absence of a solvent (Table
1, entry 11). The high yield of HMF in [Emim]Cl could be
explained by the high concentration of chloride anion in the
reaction mixture to assist with the isomerization of glucose to
fructose of Lewis acid sites on VNU-11–SO4.42 Therefore, [Emim]
Cl was used as the solvent for glucose conversion to HMF.
3.2.2. Optimization of temperature and reaction time.
Aer nding the positive role of [Emim]Cl for these reactions,
3.2. Catalytic study
3.2.1. Optimization of solvent and catalyst loading. As re-
ported in the literature, fructose or glucose is oen used in the
synthesis of HMF. Glucose molecules need to undergo the
isomerization and nish with the dehydration to form HMF. In
addition, organic solvents such as DMSO, IL 1-butyl-3-methyl-
imidazolium chloride [Bmim]Cl, IL 1-ethyl-3-methyl-
imidazolium chloride [Emim]Cl, were effective solvents for
this reaction. To evaluate the role of catalytic active sites in each
conversion, the reactions were investigated by heating fructose
or glucose at reux with the screening solvents and amount of
VNU-11–SO4 (Table 1).
ꢀ
the optimization of the effects of temperature (80–140 C) and
reaction times (0.5–24 h) was screened in both cases of fructose
and glucose. For the dehydration of fructose, when the
temperature was raised from 80–140 ꢀC, the yield of 5-HMF
increased signicantly and reached an 82% yield of 5-HMF at
140 ꢀC. The results in Fig. 2 demonstrated that the highest yield
of HMF was found at 80 ꢀC and 24 h. At the higher temperature
110 ꢀC, the yield of 83% HMF stead increased aer 3 h, uphold
magnitude in 2 h, and then slipped from 80% to 70% at the
time reaction prolong from 6 h to 24 h. The same phenomenon
almost occurred at ꢀ140 ꢀC, but the magnitude of a stronger
decline than at 110 C. Reduce the HMF yield could be caused
by the decomposition of 5-HMF at the high temperature. The
synthesis of HMF from fructose was also carried out on
The catalytic activity of the VNU-11–SO4 catalyst was inves-
tigated for dehydration of fructose under screening the amount
of catalyst from 0–30 mg in [Emim]Cl and DMSO. A high HMF
yield of 90% could be achieved under 1 mmol fructose, 6 mmol
ꢀ
[Emim]Cl as solvent at 80 C for 24 h when using 0.025 mmol
(30 mg) of VNU-11–SO4 (Table 1, entry 4), but the conversion of
glucose was not more than 30% at 140 ꢀC for 3 h (Table 1, entry
Table 1 Optimization of solvent and catalytic loading in the synthesis of 5-HMFa
Entry
Monosaccharides
Fructoseb
Solvents
VNU-11–SO4 (mg)
HMF yield (%)
1
2
3
4
5
6
7
8
[Emim]Cl
[Emim]Cl
[Emim]Cl
[Emim]Cl
DMSO
0
0
10
20
30
30
0
10
20
25
30
10
10
10
10
51.0
86.5
90.5
18.5
0
14.5
14.8
23.7
28.5
0
Glucosec
[Emim]Cl
[Emim]Cl
[Emim]Cl
[Emim]Cl
[Emim]Cl
No solvent
DMSO
9
10
11
12
13
14
7.6
5.9
3.5
DES 1d
DES 2e
a
Reaction condition: 1 mmol of fructose or glucose, 6 mmol solvent. b At 80 ꢀC for 24 h. c At 140 ꢀC for 3 h. d Deep eutectic solvent between choline
chloride and phenol was prepared at a 1 : 4 molar ratio. e Deep eutectic solvent between choline chloride and ethylene glycol was prepared at a 1 : 2
molar ratio.
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time resulted in a noticeable decrease in HMF yield, presumably
due to the decomposition of HMF (Fig. 2). At the lower
temperature (110 ꢀC), the yield of HMF increased slowly to 14%
when extending the reaction time up to overnight, and the
ꢀ
reaction did not proceed at 80 C.
It is essential to compare our work with previous literature
using MOFs as catalysts. The HMF yield from fructose was
demonstrated in Table 2 (entries 1–7). The efficiency of the
VNU-11–SO4 catalyst showed better activity than other MOFs,
ꢀ
HMF yield of 86% could be achieved at 110 C for only 3 h. In
[Emim]Cl solvent, the activity of Brønsted acid MOF as PTA(3.0)/
MIL-101 and VNU-11–SO4 were efficient for this reaction at the
low temperature. The tolerable increase of HMF yields with
longer reaction may be due to the sparing decomposition of
HMF.
The summary for the progression of glucose conversion over
a variety of catalysts and solvent was shown in Table 2, entries
ꢀ
8–12. At the high temperature of 160 C, UiO-66 provided the
desired product in a moderate yield (37%) of HMF in a mixture
of DMSO and water. MIL-101(Cr)–SO3H gave a much higher
ꢀ
yield of HMF for 7 h at 150 C, compared with the yield using
ꢀ
VNU-11–SO4 at 140 C for 8 h.
3.2.3. Recyclability of VNU-11–SO4. The recyclability of the
catalyst VNU-11–SO4 was investigated in the reaction for the
Fig. 2 The effect of temperature and time reaction of fructose (a) and
glucose (b) conversion to HMF. Reaction condition: 1 mmol mono-
saccharides, 6 mmol [Emim]Cl and 30 mg VNU-11–SO4.
a 10 mmol scale, and the HMF yield was almost the same as that
on the 1 mmol scale (84.2% vs. 90.5%).
In a previous study, high temperatures were essential for the
dehydration of glucose. Fig. 2 shows the effect of time (110–140
ꢀC) and temperature (0.5 –24 h) on the yield of HMF from the
conversion of glucose in [Emim]Cl.
The best result of glucose conversion was obtained in 140 ꢀC
with 28.5% HMF yield for 8 h. A further increase in reaction
Fig. 3 PXRD analysis of VNU-11–SO4 fresh (black) and after (red) the
glucose conversion.
Table 2 The comparison of catalysts for the conversion of monosaccharides to HMF
Temperature
(ꢀC)
Entry
React
Catalyst
Solvent
Time (h)
HMF yield (%)
Ref.
1
2
3
4
5
6
7
8
Fructose
VNU-11–SO4
VNU-11–SO4
PTA (3.0)/MIL-101
NUS-6 (Hf)
VNU-11–SO4
VNU-11–SO4
MIL-101(Cr)–SO3H
VNU-11–SO4
PO4/Nu-1000
MIL-101(Cr)–SO3H
UiO-66
[Emim]Cl
DMSO
[Emim]Cl
DMSO
[Emim]Cl
DMSO
DMSO
[Emim]Cl
Water/THF
GVC : water
DMSO
24
24
1
3.5
3
3
1
8
5
80
80
80
90.5
18.5
63
98
86
31.2
90
28.5
25
39.7
28
37
This work
This work
43
34
This work
This work
6
100
110
110
120
140
140
150
160
160
Glucose
This work
9
44
45
1
10
11
12
7
0.5
0.5
UiO-66
DMSO/water
1
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Scheme 2 Dehydration reaction between glucose under VNU-11(Hf) catalyst and [Emim]Cl solvent.
synthesis of HMF. Aer completion of the reaction, the mixture exhibited excellent performance in the 28% and 90% yield
was diluted with organic solvents and VNU-11–SO4 was towards HMF from large amount of glucose and fructose,
collected via centrifugation, washed with dichloromethane and respectively, at the low temperature. This is the rst example of
acetone, dried in reduced pressure. PXRD patterns of the fresh HMF synthesis catalyzed by superacid MOF in ionic liquids. The
and reused catalysts aer the three cycles indicated the struc- method is a promising route for the large-scale production of
ture of VNU-11–SO4 has remained mostly unchanged (Fig. 3). HMF from biomass.
The S]O coordination in the structure aer the reaction was
conrmed by FT-IR (Fig. S2, ESI†) to deny the possibility of the
Conflicts of interest
leaching SO4 from the catalyst in the reaction mixture.
The leaching test was examined by ICP-OES and the hafnium
content in the reaction mixture was less than 2 ppm, indicating
There are no conicts to declare.
negligibly slight leaching occurred from the catalyst. The
recovered VNU-11–SO4 was reused three times with a slight
decrease in the HMF yield. The recyclability of VNU-11–SO4
Acknowledgements
promises the potential application in industrial processes.
Based on the previous reports13,46 and our work, the isom-
erization of glucose and dehydration of fructose into HMF in
the presence of [Emim]Cl solvent were demonstrated the
sample evidence of VNU-11–SO4 as both of Brønsted and Lewis
sites in the reaction mechanism (Scheme 2). In the rst step,
glucose was dissolved in [Emim]Cl solvent and isomerized to
fructose by Lewis sites of VNU-11–SO4. Then, SO3H groups of
superacid MOF acted as Brønsted acid for the dehydration
process to obtain HMF.
This research was funded by Vietnam National University, Ho
Chi Minh City (VNU-HCM) under grant number 562-2020-18-01.
Linh Ho Thuy Nguyen acknowledges TX-2020-50-01 for VNU-11–
SO4 catalytic synthesis and characterization.
Notes and references
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