A green and highly efficient synthesis of 5-hydroxymethylfurfural from monosaccharides using a novel binary ionic liquid mixture

Article abstract of DOI:10.1016/j.mcat.2021.111428

We reported the development of 5-hydroxymethylfurfural (HMF) synthesis from monosaccharides using a binary ionic liquid as a reaction medium. Br?nsted–Lewis acidic ionic liquid (BLAIL) was synthesized from DABCO, 1,4-butane sultone, and AlCl₃ under mild conditions. The BLAIL was found to be a suitable catalyst for the synthesis of HMF from monosaccharides in [Emim]Cl as a solvent. Under the optimized conditions, the yields of the HMF from glucose and fructose were 30.5 % and 96.5 %, respectively. The in?uence of time, temperature, catalytic loading, and substrate on the reaction was systematically investigated. The binary ionic liquid mixture could be reused three times without a noticeable drop in the activity. The isolation of HMF was easily performed through a liquid-liquid extraction method, which could be applied to the industrial process.

Full text of DOI:10.1016/j.mcat.2021.111428

Molecular Catalysis 503 (2021) 111428
Contents lists available at ScienceDirect
Molecular Catalysis
journal homepage: www.journals.elsevier.com/molecular-catalysis
A green and highly efficient synthesis of 5-hydroxymethylfurfural from
monosaccharides using a novel binary ionic liquid mixture
a
,
b
,
c
a,
b
a,
b
a,b
Ha Bich Phan
, Quyen Bich Thi Nguyen , Cam Manh Luong , Kim Nguyen Tran
,
a,b,
Phuong Hoang Tran
*
a
Department of Organic Chemistry, Faculty of Chemistry, University of Science, Ho Chi Minh City, Viet Nam
Vietnam National University, Ho Chi Minh City, Viet Nam
b
c
Institute of Public Health, Ho Chi Minh City, Viet Nam
A R T I C L E I N F O
A B S T R A C T
Keywords:
We reported the development of 5-hydroxymethylfurfural (HMF) synthesis from monosaccharides using a binary
Monosaccharides
ionic liquid as a reaction medium. Brønsted–Lewis acidic ionic liquid (BLAIL) was synthesized from DABCO, 1,4-
5
-Hydroxymethylfurfural
3
butane sultone, and AlCl under mild conditions. The BLAIL was found to be a suitable catalyst for the synthesis
Binary ionic liquids
Fructose
of HMF from monosaccharides in [Emim]Cl as a solvent. Under the optimized conditions, the yields of the HMF
from glucose and fructose were 30.5 % and 96.5 %, respectively. The influence of time, temperature, catalytic
loading, and substrate on the reaction was systematically investigated. The binary ionic liquid mixture could be
reused three times without a noticeable drop in the activity. The isolation of HMF was easily performed through a
liquid-liquid extraction method, which could be applied to the industrial process.
Glucose
1
. Introduction
The use of renewable feedstock for biofuel and chemical production
Recently, ionic liquids have attracted much attention due to signif-
icant advantages including solvents for separation processes [25–32]
and media for chemical and biochemical reactions [33,34]. For biomass
conversion, ionic liquids (ILs) have been introduced as green, active, and
tunable reaction media in organic synthesis to substitute expensive
catalysts and hazardous volatile organic solvents [35–37]. ILs demon-
strate the remarkable ability of solubilizing carbohydrates [38–40]. ILs
have also been employed extensively as a useful solvent in the dehy-
dration of hexoses into HMF [41–43]. Li and coworkers reported the use
of acidic ion-exchange resin in [Bmim]Cl ionic liquid for dehydration of
fructose [44]. Chinnappan et al. developed a new method for synthesis
HMF from fructose using metal complexes in pyridinium dibromide
ionic liquid with satisfactory yields [45]. Recently, ILs possessing dual
roles as solvents/catalysts in the synthesis of HMF have also been re-
ported by Liu et al. [46] and Zhang et al. [43]. There have been some
issues, including the high temperature, low yield, or long reaction time
using ionic liquids [22,46,47]. Besides, studies on the ILs-promoted
synthesis of HMF at room temperature have not been reported. Thus,
various types of ILs have been prepared and tested for their catalytic
activity at room temperature.
has attracted much attention for future applications due to the dimin-
ishing fossil fuel and the growing global warming [1–4]. Biomass is vital
renewable energy and can be used as raw materials to synthesize bio-
fuels and value-added chemicals [5–7]. Recently, 5-hydroxymethylfur-
fural (HMF), recognized as a building block for synthesizing chemicals
and fuels, can be obtained from carbohydrates [2,8,9]. Carbohydrates,
including cellulose, glucose, and fructose, have been employed as
starting materials to produce HMF [10–12]. Traditionally, polar organic
solvents, including dimethyl sulfoxide, N,N-dimethylacetamide, and N,
N-dimethylformamide were employed as the solvents for the synthesis of
HMF from the carbohydrates using an acidic catalyst [13–17]. These
reactions can proceed in these solvents under medium to
high-temperature conditions [18,19]. However, the process suffered
from the high boiling point of these solvents, making the separation of
HMF difficult [20]. The extraction of HMF using nonpolar solvents gets a
problem because DMSO can be miscible with various solvents easily
[
21]. In recent years, the process in a two- or three-phase system was
also employed for HMF synthesis, but HMF was obtained in low to
Production of HMF from fructose with high yields under mild con-
ditions is a challenging topic of great importance. Here, we synthesized a
moderate yields in some reported literature [22–24].
*
Corresponding author at: Department of Organic Chemistry, Faculty of Chemistry, University of Science, Ho Chi Minh City, Viet Nam.
E-mail address: thphuong@hcmus.edu.vn (P.H. Tran).
https://doi.org/10.1016/j.mcat.2021.111428
Received 13 October 2020; Received in revised form 18 January 2021; Accepted 20 January 2021
Available online 9 February 2021
2
468-8231/© 2021 Elsevier B.V. All rights reserved.

H.B. Phan et al.
Molecular Catalysis 503 (2021) 111428
4 8 3 2 x y
Scheme 1. Synthesis of [DABCO(C H SO H) ][Al Cl ].
+
6 7 3
HRMS (ESI) m/z calcd for [M] C H O 127.0395, found 127.0379.
new BLAIL from DABCO and employed it as a catalyst for the dehy-
dration of monosaccharides into HMF. Brønsted-Lewis acidic ionic liq-
uids have been attracted much attention due to the simultaneous
possessing characteristic properties of ILs with strong Brønsted and
Lewis acidity [48]. Thus, these ILs can prompt the conversion of
monosaccharides into HMF under mild conditions.
2
.3. Recycling of catalytic system
The experiments to test the reusability of [DABCO(C
4 8 3 2
H SO H) ]
[
Al
x
y
Cl ]/[Emim]Cl were carried out as follows. After completion of the
reaction, the HMF was extracted using the mixture of ethyl acetate/
diethyl ether = 9/1 (5 × 10 mL). The catalytic system was dried under
vacuum for 10 h and was reused for the consecutive runs.
2
. Experimental
2
.1. Synthesis of ILs
3
. Results and discussion
x y
DABCO(C SO H) ][Al Cl ] was synthesized following the pro-
1
,4-bis(4-sulfobutyl)-DABCO-1,4-diium
[DABCO(C SO H) ][Al Cl ]) was prepared by a modified procedure
as in a previous literature [48]. [DABCO(C SO H) ][Al Cl ] was
prepared through a one-pot synthesis (Scheme 1). A mixture of DABCO
1 mmol), 1,4-butane sultone (2 mmol), and toluene (10 mL) was heated
tetrachloroaluminate
(
4
H
8
3
2
x
y
[
4
H
8
3
2
4
H
8
3
2
x
y
cedure described in Scheme 1. First, commercially available DABCO
reacted with 1,4-butane sultone to afford the zwitterion (A). Next, the
zwitterion (A) was treated with HCl to form chloride ionic liquid (B) as a
white liquid. Afterward, the chloride ionic liquid (B) was further treated
(
for 12 h under reflux to provide the zwitterion. HCl (3 M, 3 mL) was then
added to the resulting zwitterion, followed by stirring at room temper-
with AlCl
3 4 8 3 2 x y
in toluene to obtain [DABCO(C H SO H) ][Al Cl ]. The
ature in 2 h. Next, AlCl
mixture was stirred for 24 h under reflux. After synthesis of [DABCO
SO H) ][AlCl , the residual toluene was removed by rotary
evaporator at 50 C. The crude [DABCO(C SO H) ][Al Cl ] was
washed with acetone (3 × 15 mL) to eliminate non-ionic residues.
DABCO(C SO H) ][Al Cl ] was then dried under vacuum for 10 h to
3
(2 mmol) in toluene was added, and the reaction
characterization of [DABCO(C
4
H
8
SO
3
H)
2
][Al
x
Cl
y
] was confirmed by FT-
ꢀ 1
–
–
O
IR, and the peaks at 1160 and 1210 cm can be assigned to S
(
C
4
H
8
3
2
4
◦
]
2
ꢀ 1
ꢀ 1
stretching vibration. Additional peaks at 3452 cm and 2964 cm
4
H
8
3
2
x
y
were attributed to O
the successful preparation of [DABCO(C
ing Information, SI, Fig. S1) [48]. The formation of [DABCO
–
H and aliphatic CH
–
vibration, which confirmed
4
8
H SO H) ][Al Cl ] (Support-
3
2
x
y
[
4
H
8
3
2
x
y
obtain the pure product. The structure of [DABCO(C
4
H
8
SO
3
H)
2
][Al
x
Cl
y
]
] was demonstrated by 1H and 13C NMR with the
(
C
4
H
8
SO H) ][Al Cl
3
2
x
y
was then authenticated by FT-IR, Raman, TGA, 1H & C-NMR, and
13
presence of chemical shifts in the upfield region (SI, Fig. S2). HRMS (ESI)
was recorded in positive-ion mode showing the presence of main
HRMS.
[
DABCO(C
was recorded in negative-ion mode showing the presence of main AlCl
Al Cl -, and Al Cl - (m/z 168.8519, 228.0743, 302.8713) (SI, Fig. S4).
Furthermore, as can be seen in the Raman spectrum of [DABCO
4
H
8
SO
3
H)
2
] cation (m/z 385.1421) (SI, Fig. S3). HRMS (ESI)
2
.2. The typical procedure for the preparation of HMF
4
-,
2
5
2
7
In a typical experiment, carbohydrate (1 mmol) was placed in a 10
ꢀ 1
ꢀ 1
mL round-bottomed vessel, and a mixture of [Emim]Cl (6 mmol) -
DABCO(C SO H) ][Al Cl ] (0.1 mmol) was added. The vessel was
(C
4
H SO
8 3
2
H) ][Al
x
Cl
y
], the signals appeared at 245 cm and 500 cm
[
4
H
8
3
2
x
y
can be assigned to Al-Cl stretching modes of the Al
x
Cl
y
anion (SI, Fig. S5)
fitted with a Teflon cap, and the reaction mixture was heated for a period
of time at a selected temperature. The progress of the reaction was
checked by TLC and monitored by HPLC to determine the amount of
HMF remaining in the reaction mixture. Upon the completion of the
reaction, the pure HMF was obtained from the reaction mixture by
solvent liquid-liquid extraction with diethyl ether/ethyl acetate. All
experiments were carried out in triplicate, and the average values
showed that standard deviations of triplicates were less than 2.5 %. The
HMF was characterized by FT-IR, HRMS, and NMR.
[49].
The TGA curve of [DABCO(C
4
H
8
SO
3
H)
2
][Al
x
Cl ] showed a weight
y
◦
loss at 100 C due to the presence of moisture. Next, a sharp decrease in
◦
◦
weight loss observed at about 218 C – 350 C was mainly assigned to
the decomposition of [DABCO(C SO H) ]. The next weight loss at
351 ◦C – 500 ◦C was attributed to chloroaluminate counteranions (SI,
Fig. S6).
4
H
8
3
2
The acidity of Brønsted–Lewis acidic ionic liquids was determined by
FT-IR spectroscopy. Pyridine is used to consider Lewis and Brønsted
acidities because Brønsted and Lewis acids can be reacted with pyridine
to provide the [Pyridine-H] cation and the Pyridine–Lewis acid com-
plex [48,50]. As seen in the FTIR spectrum, the cation of [PyridineH]
FT-IR (KBr, cm 1): 3421, 2920, 2851, 1716, 1457, 1022.
ꢀ
1
+
H NMR (500 MHz, CDCl
3
) δ 9.58 (s, 1 H), 7.21 (d, J =3.2 Hz, 1 H),
+
6
.51 (d, J =3.2 Hz, 1 H), 4.71 (s, 2 H).
2

H.B. Phan et al.
Molecular Catalysis 503 (2021) 111428
Fig. 3. Effect of deep eutectic solvents on HMF yield under the present method.
Fig. 1. Effect of temperature and time.
temperature and time was not conducive to synthesize HMF under the
present condition due to the occurrence of the side reaction [21,51–53].
3
.2. The effect of catalytic amount on the conversion of glucose into HMF
After screening conditions, we found that the reaction temperature
◦
was good at 110 C, and the best yield was obtained for 1 h with 30.5 %
of HMF (Fig. 2). It was observed that the desired product was decreased
with prolonged reaction time. We then decided to consider the effect of
◦
the catalytic amount. The reaction was carried out at 110 C in the
presence of 10 mol%, 20 mol%, 30 mol%, 40 mol%, and 50 mol%
[
DABCO(C
that HMF was not obtained in the absence of the [DABCO(C
Al Cl ] catalyst. The use of 10 mol% catalyst afforded 12.8 % yield for 1
4
H
8
SO
3
H)
2
][Al
x
Cl
y
] catalyst, respectively. It should be noted
4
H
8
SO H) ]
3
2
[
x
y
h. An increasing catalyst concentration at 20 mol% afforded 15.2 %
HMF for 2 h. As mentioned earlier, the use of 30 mol% [DABCO
4 8 3 2 x y
(C H SO H) ][Al Cl ] catalyst provided the best yield of HMF with 30.5
%
%
for 1 h. Increasing the catalyst concentration from 40 mol% to 50 mol
led to a drop in the reaction yield. The possible explanation for this
Fig. 2. Effect of the catalytic amount.
phenomenon can arise from the facts that: (1) highly viscous [DABCO
SO H) ][Al Cl ] in high concentrations can prevent the diffusion
(
C
4
H
8
3
2
x
y
ꢀ
showed an absorption peak at 1547 cm 1 in the FT-IR spectra, and the
of reactants, and (2) the increasing pH of the reaction media can
unwantedly result in the generation of side products. [ref.].
absorption peak of the complex of Pyridine–Lewis is close to 1441 cm
SI, Fig. S7), which indicated that [DABCO(C H SO H) ][Al Cl ]
4 8 3 2 x y
(
3
.3. Effect of deep eutectic solvents on HMF yield
2 x y
The catalytic activity of [DABCO(C SO H) ][Al Cl ] on the con-
possessed both Brønsted and Lewis acidity types. Besides, acetonitrile is
a weak base and it is used to demonstrate the presence of a Lewis acid.
The CN group can react with Lewis acid to produce a CN–Lewis complex,
4
H
8
3
ꢀ 1
version of glucose was also compared with deep eutectic solvents (a new
type of ionic liquids) (Fig. 3). Deep eutectic solvents were prepared as
the procedure described in previous literature [54]. It was found that the
which shows absorption peaks at 2200–2400 cm in the FT-IR spectra,
and when the intensity of Lewis acid is increasing, these absorption
peaks can move to higher wavenumbers (SI, Fig. S8).
reaction using deep eutectic solvents ([choline chloride][FeCl
choline chloride][SnCl ) proceeded with cumbersome, affording less
than 1% yield. CrCl was reported as a suitable catalyst for glucose
conversion into HMF [55]. The deep eutectic solvent between choline
chloride and CrCl was found to be the best candidate in the reaction
condition. However, the HMF yields dropped quickly under prolonged
reaction time when compared with [DABCO(C SO H) ][Al Cl
3 2
] and
[
2 2
]
3
.1. The effect of temperature and time on the conversion of glucose into
3
HMF
3
4 8 3 2 x y
The as-synthesized [DABCO(C H SO H) ][Al Cl ] was used as a
homogeneous catalyst for the conversion of glucose into HMF. Reaction
time and temperature were initially investigated systematically to
obtain the optimal conditions in the procedure (Fig. 1). The reaction was
carried out with [Emim]Cl (6 mmol), glucose (1 mmol) in the presence
4
H
8
3
2
x
y
]
catalyst. Our result may not be comparable to the previous work
◦
wherein tin phosphate catalyst [56] (58.3 % yield) at 120 C for 180 min
◦
or CrCl
3
/HCl catalyst [55] (35 % yield) at 150 C for 180 min to convert
4 8 3 2 x y
of 30 mol% of [DABCO(C H SO H) ][Al Cl ] catalyst at various tem-
glucose into HMF. Nonetheless, our method is still acceptable from the
environmental viewpoint due to the absence of metal salts and/or
organic solvents.
peratures for different times. It was observed that the reaction harshly
◦
proceeded at 60 C to give less than 1% HMF yield. The yield could be
improved at higher temperatures. The good yield of HMF was obtained
◦
at 110 C for 2 h. However, the HMF is not stable in acidic conditions at
high temperatures for a long reaction time. Thus, the increase of
3

H.B. Phan et al.
Molecular Catalysis 503 (2021) 111428
3
.4. The optimization of reaction condition on the synthesis of HMF from
fructose at room temperature (RT)
We then explore the substrate scope in our method, and fructose was
chosen for investigation. HMF from fructose was obtained in 46 % yield
4 8 3 2 x y
in the presence of 1 mol% of [DABCO(C H SO H) ][Al Cl ] at room
temperature. When 5 mol% of catalyst was used, the HMF yield could be
improved significantly, with 65 % for 24 h. An increase of catalytic
amount to 10 mol% did not provide a better yield (Fig. 4).
3
.5. The optimization of reaction temperature for HMF synthesis from
fructose
The HMF yield can be dramatically enhanced by increasing the re-
action temperature. In the present method, the temperature could
exhibit a significant effect on the reaction rate (Fig. 5). The reaction
proceeded slowly at room temperature to furnish 65 % of HMF yield for
◦
2
4 h. However, the HMF yield could be improved to 99 % at 80 C for 8 h
4 8 3 2
Fig. 4. Optimization of the reaction condition using [DABCO(C H SO H) ]
in the presence of 5 mol% of [DABCO(C
4
H
8
SO
3
H)
2
][Al
x
Cl
y
]. Increasing
[
Al
x
Cl
y
] catalyst on HMF synthesis from fructose.
◦
the reaction temperature to 120 C resulted in decreasing HMF yield due
to the side reaction [21].
3
4 8 3 2 x y
.6. Reusability of [DABCO(C H SO H) ][Al Cl ]/[Emim]Cl
Recoverability and reusability of the catalyst are highly preferable in
terms of green chemistry. To emphasize the significant point of the
catalytic system, the recycling experiments of [DABCO(C SO H)
]/Emim]Cl system were investigated in the synthesis of HMF at
4
H
8
3
2
]
[
Al
x
Cl
y
◦
1
10 C for 1 h using 1 mmol of glucose dissolved in 6 mmol of [Emim]Cl
4 8 3 2 x y
and 30 mol% of [DABCO(C H SO H) ][Al Cl ]. After completion, the
reaction mixture was extracted with ethyl acetate/diethyl ether (5 × 10
mL). Organic solvents were decanted, and the residue catalyst was dried
under vacuum for 10 h. Then, a new run was performed by adding the
fresh glucose (1 mmol) to the remaining [DABCO(C
Al Cl ]/[Emim]Cl and heated under optimized conditions. Experi-
mental results indicated that the [DABCO(C SO H) ][Al Cl ]/
Emim]Cl catalytic system could be recycled three times with a little loss
in catalytic performance (Fig. 6). The recovered [DABCO(C SO H)
Al Cl ]/[Emim]Cl catalytic system was confirmed by FTIR without
significant change in functionality as compared with the fresh [DABCO
SO H) ][Al Cl ]/[Emim]Cl (SI, Fig. S9).
4 8 3 2
H SO H) ]
[
x
y
4
H
8
3
2
x
y
[
4
H
8
3
2
]
[
x
y
Fig. 5. Effect of temperature on HMF synthesis from fructose in the presence of
mol% [DABCO(C SO H) ][Al Cl ].
(
C
4
H
8
3
2
x
y
5
4
H
8
3
2
x
y
4
. Conclusions
We developed a new catalytic system for the conversion of mono-
saccharides to HMF. The new DABCO-based dicationic ionic liquid
4 8 3 2 x y
Fig. 6. Extraction phase and recycling of the catalytic system [DABCO(C H SO H) ][Al Cl ]/[Emim]Cl.
4

H.B. Phan et al.
Molecular Catalysis 503 (2021) 111428
[
DABCO(C
three-step, one-pot procedure and characterized by FT-IR, H &
NMR, TGA, Raman, and HRMS (ESI). HMF yields were obtained in high
yields from fructose in the presence of the [DABCO(C SO H)
]/[Emim]Cl under a mild condition. The results showed that
DABCO(C SO H) ][Al Cl ]/[Emim]Cl efficiently facilitated HMF
4
H
8
SO
3
H)
2
][Al
x
Cl
y
] was easily synthesized from DABCO via a
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