A Divergent Paired Electrochemical Process for the Conversion of Furfural Using a Divided-Cell Flow Microreactor

Article abstract of DOI:10.1002/cssc.202002833

Furfural is a prominent, non-petroleum-based chemical feedstock material, derived from abundantly available hemicellulose. Hence, its derivatization into other useful biobased chemicals is a subject of high interest in contemporary academic and industrial research activities. While most strategies to convert furfural require energy-intensive reaction routes, the use of electrochemical activation allows to provide a sustainable and green alternative. Herein, a disparate approach for the conversion of furfural is reported based on a divergent paired electrochemical conversion, enabling the simultaneous production of 2(5H)-furanone via an anodic oxidation, and the generation of furfuryl alcohol and/or hydrofuroin via a cathodic reduction. Using water as solvent and NaBr as supporting electrolyte and electron-mediator, a green and sustainable process was developed, which maximizes productive use of electricity and minimizes byproduct formation.

Full text of DOI:10.1002/cssc.202002833

Chemistry–Sustainability–Energy–Materials
Accepted Article
Title: A Divergent Paired Electrochemical Process for the Conversion
of Furfural Using a Divided-Cell Flow Microreactor
Authors: Yiran Cao, Jasper Knijff, Amin Delparish, Maria Fernanda
Neira d'Angelo, and Timothy Noel
This manuscript has been accepted after peer review and appears as an
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of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
published online in Early View as soon as possible and may be different
to this Accepted Article as a result of editing. Readers should obtain
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: ChemSusChem 10.1002/cssc.202002833
Link to VoR: https://doi.org/10.1002/cssc.202002833
01/2020

10.1002/cssc.202002833
ChemSusChem
COMMUNICATION
A Divergent Paired Electrochemical Process for the Conversion
of Furfural Using a Divided-Cell Flow Microreactor
Yiran Cao[a], Jasper Knijff[a], Amin Delparish[a], Maria Fernanda Neira d'Angelo[a], Timothy Noёl[a,b,*]
Abstract: Furfural is a prominent, non-petroleum-based chemical
feedstock material, derived from abundantly available hemicellulose.
Hence, its derivatisation into other useful biobased chemicals is a
subject of high interest in contemporary academic and industrial
research activities. While most strategies to convert furfural require
energy-intensive reaction routes, the use of electrochemical activation
allows to provide a sustainable and green alternative. Herein, we
report a disparate approach for the conversion of furfural based on a
divergent paired electrochemical conversion, enabling the
simultaneous production of 2(5H)-furanone via an anodic oxidation,
and the generation of furfuryl alcohol and/or hydrofuroin via a cathodic
reduction. Using water as solvent and NaBr as supporting electrolyte
While several useful electrochemical strategies for the conversion
of furfural have been developed, the focus so far was almost
exclusively on the optimization of a single electrode reaction.
However, when both electrode reactions are harmonized to
produce value-added products,
a green and sustainable
synthesis can be obtained which maximizes productive use of
electricity, minimizes waste generation and reduces energy
consumption.[17–20] Such a coupled process, also called “paired
electrolysis”, would be of great added value for the conversion of
furfural, where the economical margins are often low.
Herein, we describe such a divergent paired electrochemical
conversion of furfural where the cathodic and anodic reactions are
separated by a membrane and are productively used to generate
valuable derivatives (Figure 1A). To further increase the utility and
scalability of the process,[21] the reactions are carried out in a
continuous-flow electrochemical reactor with a narrow inter-
electrode gap (Figure 1B).[22–26] The selectivity can be increased
in such reactors due to the large electrode surface-to-volume ratio
and due to a meticulous control over the residence time and the
cell potential. Using such intensified reaction conditions, the
reaction time is typically reduced significantly compared to batch
cells and, thus, the products are only briefly exposed to the
electrochemical conditions, efficiently avoiding undesired follow-
up reactions.[27–29] In this work, we show that a divergent paired
electrochemical flow strategy enables the simultaneous
production of 2(5H)-furanone via an anodic oxidation, and the
generation of furfuryl alcohol and/or hydrofuroin via a cathodic
reduction (Figure 1A). It should be noted that these three
biobased compounds derived from furfural have great synthetic
and practical value. 2(5H)-furanone can readily be reduced to
and electron-mediator,
a green and sustainable process was
developed which maximizes productive use of electricity and
minimizes byproduct formation.
Furfural is one of the most prominent biobased molecules,
registered as a top 30 biomass-derived platform molecule by the
US Department of Energy.[1] It is obtained by hydrolysis and
dehydration of xylan, which is abundantly available from
hemicellulose. Furfural is currently produced on a 300 kTon per
annum scale and about 70% of its production is carried out in
China.[2]
The establishment of furfural as a commodity chemical spurs
academic and industrial interest to develop new synthetic routes
for its further derivatisation into useful chemicals, materials and
biofuels.[3–5] Amongst the different strategies used to convert
furfural (e.g. pyrolysis, gasification, thermo-catalytic processes),
the use of electrochemical activation enables a green and
sustainable alternative to these often high-energy-demanding
processes.[6–10] Notably, electrochemistry allows to convert green
electricity, derived from wind and solar energy, directly into useful
chemicals and kinetic barriers are overcome by applying a
suitable potential over the electrodes. Hence, no additional
reagents are required to enable reduction[11–14] and oxidation
processes,[15] which can aid to further reduce fossil fuel
consumption (e.g. hydrogen is often derived from natural gas via
the water-gas shift reaction).[16]
generate γ-butyrolactone,[30,31]
a valuable biobased solvent,
synthetic intermediate and monomer for the synthesis of poly(γ-
butyrolactone).[32] Furfuryl alcohol is mainly used as a raw
material to produce furan-based foundry resins,[13] while
hydrofuroin can be utilized as a jet-fuel precursor.[33]
We commenced our investigations by repurposing our original
electrochemical flow reactor design (Figure 1B).[34] An ion
exchange membrane was used to separate the anodic and the
cathodic electrolysis half-cells.[35] Both cation- (Nafion XL) and
anion-exchange (Fumasep FAS-50) membranes[36] were
purchased and could be readily sandwiched between two Teflon
reaction channel spacers as shown in Figure 1 B. The reaction
solution was introduced into the two half-cells of the
electrochemical flow reactor using syringe pumps (Fusion 200,
Chemyx). The catholyte and anolyte were separately collected
and analysed by GC-FID.
[a]
Department of Chemical Engineering and Chemistry, Sustainable
Process Engineering, Eindhoven University of Technology (TU/e),
Het Kranenveld (Bldg 14 – Helix), 5600 MB Eindhoven, The
Netherlands.
[b]
[*]
Current address: Flow Chemistry Group, van ’t Hoff Institute for
Molecular Sciences (HIMS), University of Amsterdam (UvA),
Science Park 904, 1098 XH, Amsterdam, The Netherlands
E-mail: t.noel@uva.nl.
Electronic Supplementary Information (ESI) available: Materials and
methods as well as detailed information for the construction of the
reaction control system and the device source code. See DOI:
10.1002/x0xx00000x
This article is protected by copyright. All rights reserved.

10.1002/cssc.202002833
ChemSusChem
COMMUNICATION
extend the reaction times.[29,37,38] Extended reaction times,
observed with potentiostatic electrochemical transformations, is
an often encountered problem in batch electrolysis as the current
decreases with increasing conversions.[39] However, in flow, high
substrate concentrations are encountered at the entrance of the
reactor and low concentrations at the exit, leading to an average
current density over the entire reactor length. This phenomenon
in combination with the high electrode surface-to-volume ratio
results in significantly reduced reaction times in flow.[22] An
aqueous mixture of furfural and NaBr, as supporting electrolyte
and potentially as anodic electron mediator[40] facilitating the
oxidation process,[41,42] was infused into the reactor. The two half-
cells are separated by a Fumasep FAS-50 anion-exchange
membrane and graphite was initially selected as anode and lead
as the cathode, which has a high hydrogen overpotential (Table
1, Entry 1).[43] Suppression of the hydrogen evolution reaction is
important to ensure high Faradaic efficiencies[44,45] and to avoid
gas formation which leads to a higher Ohmic drop.[46] As can be
seen from Table 1, within 5 min residence/reaction time, good
yields are obtained for 2(5H)-furanone at the anodic half-cell and
furfuryl alcohol and hydrofuroin at the cathodic half-cell. At a cell
potential of 2.4 V, a higher selectivity is observed for furfuryl
alcohol at the cathode (Table 1, Entry 1). A higher yield for both
2(5H)-furanone and hydrofuroin are observed at a cell potential of
2.9 V, respectively 77% and 71% (Table 1, Entry 1). This result
demonstrates that small changes in cell potential allow to fine-
tune the selectivity of the electrochemical redox process. Other
electrode materials, such as Ni, 316 L stainless steel, Monel 400,
copper, showed a reduced efficacy to generate the targeted
compounds (Table 1, Entries 2-9).
Divergent paired electroconversion of furfural
A
O
O
O
O
2(5H)-furanone (2)
OH
H
O
O
H
O
furfural
+
H
1
(
)
H
divided-cell flow microreactor
O
HO
3
4
)
furfuryl alcohol (
)
hydrofuroin (
Divided-cell flow microreactor
B
500
400
300
200
100
Figure 1. (A) Processes based on a divergent paired electrolysis of furfural
allows to obtain useful derivatives of both cathodic and anodic processes
simultaneously. (B) Schematic representation of the divided-cell flow
microreactor design using an ion-exchange membrane to separate the anodic
and the cathodic electrolysis half-cells.
cation-exchange membrane
anion-exchange membrane
0
2.0
2.2
2.4
2.6
2.8
3.0
3.2
3.4
3.6
Potential (V)
Figure 2. Voltammogram of furfural in the divided-cell flow microreactor
design using an anion- or a cation-exchange membrane.
Prior to the optimization studies, a voltammogram was recorded
to establish the operational windows for the electrolysis of furfural
(Figure 2). Two clear plateaus can be distinguished at 2.3–2.5 V
and 2.8–3.0 V for both the cation- and the anion-exchange
membrane. The current is higher at any given potential for the
cation exchange membrane, suggesting a lower resistance for ion
transport compared to the anion-exchange membrane.
Based on these results (Figure 2), we decided to use our flow cell
in a constant-potential or potentiostatic operation mode and set
the cell potential at either 2.4 V or 2.9 V (Table 2; see also
Supporting Information). In our experience, a potentiostatic mode
in combination with a continuous-flow operation allows to obtain
high selectivities for a targeted compound without the need to
An investigation of the yield and selectivity in function of the
residence/reaction time was carried out for both the cation- and
the anion-exchange membrane configuration (Figure 3). For the
anodic half-cell (Figure 3A), the highest yield for 2(5H)-furanone
(77% GC yield) is observed at 5 min for the anion-exchange
membrane after which it reaches
a plateau. At 5 min
residence/reaction time, the yield at the cation-exchange
membrane is only 62% for the targeted compound (Figure 3A).
Interestingly, at the cathodic half-cell, better results are obtained
with the cation-exchange membrane for the production of furfuryl
alcohol and hydrofuroin. However, the difference in performance
between the two membranes is less pronounced than for the
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10.1002/cssc.202002833
ChemSusChem
COMMUNICATION
selectivity (Figure 4). A higher concentration would result in a
higher throughput whilst keeping the residence time constant.
Indeed, the concentration could be increased up to 0.6 M furfural
without reducing the efficacy of the electrochemical process.
Higher concentrations were not possible due to the limited
solubility of furfural in water.
Based on the experimental observations, a plausible mechanism
is suggested in Figure 5. In the anodic half-cell, the C5 chemical
furfural is converted into the C4 building block 2(5H)-furanone in
excellent yield. Based on recent work from Song, Han and
coworkers,[51] we suggest that a hydroxyl-radical-induced C–C
bond cleavage generates the corresponding 2-hydroxyfuran and
formic acid. Subsequent isomerization of 2-hydroxyfuran
generates the observed 2(5H)-furanone. In the cathodic half-cell,
furfural is reduced to generate the corresponding radical.[44]
These radicals can dimerize to yield the C10 compound,
hydrofuroin. Competitively, the radical can consume another
electron to generate furfuryl alcohol.
A
80
70
60
50
40
30
20
cation-exchange membrane
anion-exchange membrane
1
2
3
4
5
6
7
8
Residence time (min)
B
80
70
60
50
40
30
20
10
(3) with cation-exchange membrane
(3) with anion-exchange membrane
(4) with cation-exchange membrane
(4) with anion-exchange membrane
1
2
3
4
5
6
7
8
Residence time (min)
Figure 3. Residence Time Screening for the (A) anodic half-cell yielding
2(5H)-furanone (2), and (B) cathodic half-cell yielding furfuryl alcohol (3) and
hydrofuroin (4). Reaction conditions: 0.1 M furfural, 0.1 M NaBr, H2O, graphite
anode|lead cathode, cell potential 2.9 V. Yields obtained with GC-FID and
internal standard calibration (toluene).
anodic half-cell; e.g. at 5 min 75% hydrofuroin and 14 % furfuryl
alcohol is obtained for the cation-exchange membrane versus
67% hydrofuroin and 26% furfuryl alcohol for the anion-exchange
membrane. Hence, we selected the anion-exchange membrane
for our further studies.
Figure 4. Concentration effect on the divergent paired electrolysis of furfural.
Reaction conditions: x M furfural, 0.1 M NaBr, H2O, 5 min residence time,
Fumasep FAS-50 as an anion exchange membrane. [b] GC-yield using GC-FID
with internal standard (toluene).
Next, we investigated the effect of various halide sources on the
reaction outcome (Table 2). The best results were obtained with
bromide salts (Table 2, Entry 1 versus Entry 2). It is known that
bromide ions enable mild and indirect anodic oxidations via either
hypobromite (BrO-) or bromonium (Br+) intermediates.[47–50] Other
alkali bromide sources were also effective but the best results
were obtained with cheap and abundantly available NaBr (Table
2, Entries 1, 3-7). Addition of small quantities (10 vol %) of organic
solvents did not lead to any significant improvement and was even
less effective in the cases of methanol and THF (Table 2, Entries
8-10). Interestingly, in the absence of a membrane, a much
reduced reaction efficiency was noticed (Table 2, Entry 11); this
Anodic half-cell reaction
2 H2O
- 2 H+, - 2 e-
O
H
O
O
2 HO
O
O
O
rearrangement
- HCOOH
H
2
( )
2(5H)-furanone
furfural
Cathodic half-cell reaction
H+, + e-
O
O
H
O
OH
H
OH
O
dimerization
observation demonstrates that the presence of
a suitable
O
HO
hydrofuroin
furfural
membrane to separate the two half reactions is crucial to obtain
high yields and selectivities.
4
(
)
H+, + e-
O
H
O
In order to scale up this paired electrolysis of furfural, we
wondered if it was possible to increase the concentration of the
starting material without compromising the yield and the
H
H
3
)
furfuryl alcohol (
Figure 5. Proposed mechanism for the divergent paired electrolysis of furfural.
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10.1002/cssc.202002833
ChemSusChem
COMMUNICATION
Table 1. Screening of electrode materials for the paired electrolysis of furfural.[a]
O
O
H
O
O
2(5H)-furanone (2)
furfural
OH
O
1
)
(
O
H
O
NaBr, H2O
+
H
H
divided-cell flow microreactor
O
HO
FAS-50 (anion-exchange membrane)
furfuryl alcohol (3)
hydrofuroin (4)
Yield 2 [%][b]
2.4 V 2.9 V
46 77
Yield 3 [%][b]
2.4 V 2.9 V
Yield 4 [%][b]
2.4 V 2.9 V
Entry
Anode
Cathode
1
2
3
4
5
6
7
8
9
G
Ni
Pb
58
54
45
60
56
47
51
28
34
20
17
29
18
71
46
32
55
64
62
49
20
33
Pb
Trace 11
Trace 10
316L
Pb
Pb
10
9
Monel 400
14
40
36
32
32
27
23
73
70
65
69
49
26
12
G
G
G
G
G
Cu
24
25
Monel 400
Ni
9
23
17
17
G
Trace
Trace
20
316L
Trace
[a] Reaction conditions: 0.1 M furfural, 0.1 M NaBr, H2O, 5 min residence time, Fumasep FAS-50 as an anion exchange membrane. [b] GC-
yield using GC-FID with internal standard (toluene).
Table 2. Influence of halide sources, solvent and control experiment for the paired electrolysis of furfural.[a]
O
O
H
O
O
2
(
2(5H)-furanone
)
furfural
(1)
OH
O
O
H
O
MX, solvent
+
H
H
divided-cell flow microreactor
O
HO
FAS-50 (anion-exchange membrane)
furfuryl alcohol (3)
hydrofuroin (4)
tR = 5 min, 2.9 V cell potential
Entry
MX
NaBr
NaCl
LiBr
KBr
Solvent
H2O
Yield 2 [%][b]
Yield 3 [%][b]
Yield 4 [%][b]
1
2
77
Trace
64
20
Trace
10
71
Trace
32
H2O
3
H2O
4
H2O
59
26
55
5
CsBr
H2O
61
25
67
6
MnBr2
TBAB
NaBr
NaBr
NaBr
NaBr
H2O
15
7
27
7
H2O
38
24
29
8
H2O + CH3CN[c]
H2O + CH3OH[c]
H2O + THF[c]
H2O
77
27
66
9
58
33
41
10
11[d]
52
12
22
Trace
16
11
[a] Reaction conditions: 0.1 M furfural, 0.1 M MX, graphite anode|lead cathode, residence time 5 min, cell potential 2.9 V, full conversion
with anion exchange membrane [b] Yields obtained with GC-FID and internal standard calibration (toluene). [c] The solvent consists of 90
vol% H2O and 10 vol% organic solvent. [d] The reaction was done with the same conditions as Entry 1 but in an undivided electrochemical
flow cell.
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10.1002/cssc.202002833
ChemSusChem
COMMUNICATION
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10.1002/cssc.202002833
ChemSusChem
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Yiran Cao, Jasper Knijff, Amin Delparish, Maria Fernanda Neira d'Angelo and Timothy Noёl*
Page No. – Page No.
A Divergent Paired Electrochemical Process for the Conversion of Furfural Using a Divided-Cell
Flow Microreactor
Herein, we describe a divergent paired electrochemical conversion of furfural where the cathodic and anodic reactions are separated by a
membrane and are productively used to generate valuable derivatives. We show this strategy enables the simultaneous production of 2(5H)-
furanone via an anodic oxidation, and the generation of furfuryl alcohol and/or hydrofuroin via a cathodic reduction
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