Supported Molybdenum Catalysts for the Deoxydehydration of 1,4-Anhydroerythritol into 2,5-Dihydrofuran

Article abstract of DOI:10.1002/cssc.201700010

Efficient deoxygenation strategies are crucial for the valorization of renewable feedstocks. Deoxydehydration (DODH) enables the direct transformation of two adjacent hydroxyl groups into a double bond. Supported molybdenum-based catalysts were utilized for the first time in DODH. MoO_x/TiO₂ showed superior catalytic activity compared to common molybdenum salts. The catalyst efficiently converted 1,4-anhydroerythritol into 2,5-dihydrofuran in the presence of 3-octanol as reducing agent, showing high reproducibility and stability.

Full text of DOI:10.1002/cssc.201700010

Accepted Article
Title: Supported molybdenum catalysts for the deoxydehydration of
1,4-anhydroerythritol into 2,5 dihydrofuran
Authors: Lennart Sandbrink, Klaus Beckerle, Isabell Meiners, Rebecca
Liffmann, Khosrow Rahimi, Jun Okuda, and Regina Palkovits
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To be cited as: ChemSusChem 10.1002/cssc.201700010
Link to VoR: http://dx.doi.org/10.1002/cssc.201700010
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10.1002/cssc.201700010
ChemSusChem
COMMUNICATION
Supported molybdenum catalysts for the deoxydehydration of
1,4-anhydroerythritol into 2,5-dihydrofuran
Lennart Sandbrink,[a][d] Klaus Beckerle,[b][d] Isabell Meiners,[a] Rebecca Liffmann,[b] Khosrow Rahimi,[c]
Jun Okuda[b]* and Regina Palkovits[a]*
Abstract: Efficient deoxygenation strategies are crucial for the
valorization of renewable feedstocks. Deoxydehydration (DODH)
enables the direct transformation of two adjacent hydroxyl groups
into a double bond. Supported molybdenum-based catalysts were
utilized for the first time in DODH. MoOx/TiO2 possesses superior
catalytic activity compared to common molybdenum salts. The
(Scheme 1). 1,4-AE can be easily derived from erythritol,9 which
is a fermentation product of sugars.10 Previous studies already
showed that 1,4-AE is a promising bio-based intermediate for
the production of C4 chemicals.6d,,8a,11
catalyst
efficiently
converted
1,4-anhydroerythritol
into
2,5-dihydrofuran in the presence of 3-octanol as reducing agent
showing high reproducibility and stability.
Scheme 1.Scheme of the model reaction: DODH of 1,4-AE into 2,5-DHF.
Introduction
Results and Discussion
In contrast to petrochemical value chains, deoxygenation
reactions are the major pathway to valorize renewable feedstock
molecules into bio-based products.1 The deoxydehydration
(DODH) has evolved to be an efficient alternative to established
deoxygenation routes. It offers direct access to olefins from diols,
which are abundant functional groups in biomass-related
feedstocks.2 The first catalytic deoxydehydration was described
by Cook and Andrews in 1996.2 Starting from 2008 several
researchers expanded the reaction class to the high potential
that it offers today.3 The reaction can be carried out with
molecular rhenium-,3 molybdenum-4 or vanadium-based5
catalysts, which in combination with a stoichiometric reductant
enable the transformation of various diols into olefins. During the
past years, the reductant, catalyst and substrate scope has been
expanded drastically.6 To develop DODH further, supported
In the current study, commercially available molybdenum
compounds including Mo(CO)6 [1], MoCl3 [2], MoO2Cl2 [3],
Na2MoO4∙2H2O [4], Na2MoO4 [5], (NH4)2MoO4 [6], MoO3 [7],
(NH4)6Mo7O24∙4H2O [8], and were initially examined in the DODH
of 1,4-anhydroerythritol to 2,5-dihydrofuran using 3-octanol as
reducing agent and solvent (Table 1). During the reaction, 3-
octanol is oxidized to 3-octanone. Under standard reaction
conditions (5 mol.% Mo, 10 equiv. 3-octanol relative to substrate,
200 °C, 18 h), most of the compounds were found to be active in
the test reaction. Although the highest yields of 2,5-dihydrofuran
were observed for compounds with an oxidation state (OS) of
+VI for molybdenum, the oxidation states 0 and +III were found
to be active as well. (NH4)6Mo7O24∙4H2O [8] facilitated the
highest overall conversion and yield of the DODH-product. The
reaction mechanism of the Molybdenum-catalyzed DODH was
proposed to be based on the condensation of MoO3 with the diol.
Afterwards coordination and transfer hydrogenation of the
reducing agent and the final extrusion of the DODH-product take
place.12 Next to the DODH-product 2,5-DHF, high amounts of
the ketal, formed by condensation of 3-octanone and
1,4-anhydroerythritol, were obtained as the major side product.
The dehydration of 3-octanol to 2- and 3-octene occurred as
side reaction (see supporting information (SI), Scheme S1 and
S2). The gap in the mass balance is assumed to be based on
condensation reactions producing high boiling products. These
products were not detectable with the applied GC-MS-analysis
due to lack of volatility (compare NMR-analysis in SI, Figure S8
and S9).
rhenium catalysts were presented to obtain heterogeneous
7
systems.
With ReOx/TiO2 we recently reported a stable
heterogeneous DODH-catalyst.7b Further heterogeneous
systems were published by Nakagawa and Tomishige. They
applied ceria supported Rhenium catalysts promoted with Au or
Pd for the selective deoxydehydration or hydrodeoxygenation of
various diols and polyols in the presence of hydrogen gas as
reducing agent.8 However, an economic process with such
rhenium catalysts remains certainly challanging. In order to
facilitate a broader application of the reaction class, we report
here the first supported molybdenum catalysts for DODH. In the
following studies the DODH of 1,4-anhydroerythritol (1,4-AE) to
2,5-dihydrofuran (2,5-DHF) was used as model reaction
[a]
Dr. L. Sandbrink, I. Meiners, Prof. R. Palkovits
Institut für Technische und Makromolekulare Chemie (ITMC), RWTH
Aachen University, Aachen 52074, Germany
E-mail: Palkovits@itmc.rwth-aachen.de
Dr. K. Beckerle, R. Liffmann, Prof. J. Okuda
Institut für Anorganische Chemie, RWTH Aachen University,
Aachen 52074, Germany
As already described by the group of Fristrup in 2014 for the
DODH of 1,2-tetradecanediol in dodecane using 3-octanol as
reductant, the Mo(+IV) compound sodium molybdate [4] was
inactive in DODH.4 The use of anhydrous sodium molybdate [5]
showed no increase in catalyst activity. Although the authors
explained the inactivity of Na2MoO4 by the lack of solubility in the
dodecane solvent,4 we assume that also the type of active
molybdate species can play a key role as discussed for Table 2.
[b]
[c]
[d]
Dr. K. Rahimi
DWI-Leibniz-Institute for Interactive Materials, Aachen 52074, North
Rhine-Westphalia, Germany
L.S. and K.B. contributed equally.
Supporting information for this article is given via a link at the end of
the document
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10.1002/cssc.201700010
ChemSusChem
COMMUNICATION
[4b, 8b] showed a characteristic band between 890 and
960 cm-1, which is attributed to the stretching modes of the
terminal Mo=O bond (Figure 1). The wavenumber of the band
increases with the degree of polymerization. Therefore, the
lower wavenumber for the sodium molybdate based catalysts
Table 1. Product distribution of homogeneous reference catalysts in the test
reaction 1,4 anhydroerythritol (1,4-AE) to 2,5 dihydrofuran (2,5-DHF).[a]
X
Y
Y
Y
Catalyst (OS)
(1,4-AE) (2,5-DHF)
[%]
(ketal)
[%]
(octenes)[b]
[%]
[%]
2-
[4a,b] is explained by the formation of isolated MoO4 species
-
9
0
2
0
on the surface. The use of ammonium heptamolybdate as a
Mo(CO)6 [1] (0)
MoCl3 [2] (+III)
MoO2Cl2 [3] (+IV)
36
75
60
9
21
22
28
0
6
6
precursor [8a,b] results in polymerized clusters on the catalyst
surface,13 associated with
a higher activity for DODH in
15
10
2
16
11
0
comparison to isolated molybdate species.
The influence of reduction on the product yield was rather low,
but octene formation increased, indicating more pronounced
acidic properties of the reduced catalysts. Raman spectra of the
reduced materials showed an increase of the wavenumber of
the bands.
Na2MoO4∙2H2O [4]
(+IV)
Na2MoO4 [5] (+IV)
(NH4)2MoO4 [6] (+IV)
MoO3 [7] (+VI)
11
55
91
83
1
1
0
27
29
38
10
20
19
3
5
(NH4)6Mo7O24∙4H20 [8]
(+VI)
892 918 943 973
3
[a] Conditions: 0.4 mmol 1,4-anhydroerythritol, 5 mol% Mo and 10 eq.
3-octanol relative to substrate, 200 °C, 18 h. Conversion and yields
determined by NMR spectroscopy. [b] Based on 3-octanol.
Na2MoO4•H2O/TiO2 [4a]
MoOx/TiO2 (Na2MoO4•H2O) [4b]
(NH4)6Mo7O24•4H2O/TiO2 [8a]
MoOx/TiO2 ((NH4)6Mo7O24•4H2O) [8b]
Table 2. Product distribution of supported Mo-catalysts and mixtures in the
test reaction 1,4 anhydroerythritol (1,4-AE) to 2,5 dihydrofuran (2,5-DHF).[a]
X
Y
Y
Y
Catalyst
(1,4-AE) (2,5-DHF)
[%]
(ketals)
[%]
(octenes)[c]
[%]
(Mo content [%])[b]
[%]
Na2MoO4∙2H2O/TiO2 [4a]
(4.8)
27
1
0
1
3
˂1
˂1
15
MoOx/TiO2 (Na2MoO4∙2H2O)[d]
[4b] (5.1)
39
5
800
900
1000
1100
(NH4)6Mo7O24∙4H20/TiO2 [8a]
(4.9)
100
48
Wavenumber [cm-1]
MoOx/TiO2
((NH4)6Mo7O24∙4H20)[e]
[8b] (4.7)
94
55
9
48
Figure 1. Raman spectra of impregnated [4a, 8a] and reduced [4b, 8b]
molybdate catalysts in the region of characteristic Mo-oxo bonds (anatase
background subtracted).
In-situ mixture [4c]:
Na2MoO4+TiO2
In-situ mixture [8c]:
(NH4)6Mo7O24∙4H20+TiO2
19
4
0
3
100
14
76
2
10
1
16
1
Pure titanium dioxide [9] is inactive in DODH. However, an in-
situ mixture of titanium dioxide and ammonium heptamolybdate
[8c] resulted in higher yields of 2,5-dihydrofuran than the
supported catalysts formed prior to reaction [8a,b]. Similar to the
unreduced catalyst [8a], the mixture [8c] resulted in lower octene
formation compared to the reduced one [8b].
The most active catalysts MoOx/TiO2 ((NH4)6Mo7O24∙4H2O) [8b]
and in-situ mixture [8c] (NH4)6Mo7O24∙4H2O+TiO2 were further
examined in terms of reproducibility and recyclability (Figure 3
and 4). For each of the systems three independent test reactions
were performed, showing good reproducibility for both of them
(see SI, Figure S1 and S2).
TiO2 [9]
[a] Conditions: 0.4 mmol 1,4-anhydroerythritol, 5 mol% Mo and 10 equiv.
3-octanol relative to substrate, 200 °C, 18 h. Conversion and yields
determined by NMR spectroscopy. [b] Determined by ICP-OES. [c] Based on
3-octanol. [d] Mo-precursor: Na2MoO4∙2H2O, reduction conditions: 3 h, 300 °C,
2 °C/min. [e] Mo-precursor: (NH4)6Mo7O24∙4H20, reduction conditions: 3 h,
300 °C, 2 °C/min.
In the presence of MoCl3 [2] and MoO2Cl2 [3], the yield of
octenes increased due to hydrochloric acid formation during the
reaction catalyzing the dehydration of 3-octanol.
Ammonium heptamolybdate [8] and sodium molybdate [4] were
selected as precursors for the impregnation on a support
material. Titanium dioxide enabled already high activity of
supported rhenium catalysts in DODH7b and was selected as
support. A fraction of the impregnated catalysts was directly
tested in the DODH of 1,4-anhydroerythritol. The other fraction
was reduced to lower oxidation state of molybdenum oxides
(MoOx) in H2-atmosphere at 300 °C prior to reaction. Generally,
the use of ammonium heptamolybdate [8a-c] increased the
conversion and yield of the DODH-product compared to the
other commercially available molybdenum salts (Table 2).
Catalysts based on sodium molybdate [4a-c] possessed low
catalytic activity. Raman spectra of the two reduced catalysts
After the reaction, two of the catalysts were recycled and
subjected to four consecutive runs. The impregnated and
reduced catalyst [8b] exhibited good reproducibility in the DODH
reaction.
Recycling
of
the
in-situ
formed
[8c]
(NH4)6Mo7O24∙4H2O+TiO2 features higher deviations in
conversion and yield of 2,5-dihydrofuran. However, excellent
recyclability emphasizes an efficient in-situ formation of a
supported molybdenum catalyst. The most noticeable difference
of the both recycling series could be observed in the formation of
octenes. While octene formation remained constantly low for the
recycling of the in-situ mixture [8c], the use of the impregnated
and reduced catalyst [8b] resulted in an initially high yield and a
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10.1002/cssc.201700010
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100
80
60
40
20
0
Y (2,5-DHF)
Y (octenes)
X (1,4-AE)
1
2
3
4
5
Run
Figure 3. Recycling of MoOx/TiO2 ((NH4)6Mo7O24∙4H2O) [8b]. Conditions:
0.4 mmol 1,4-anhydroerythritol, 5 mol% Mo in the starting catalyst and
10 equiv. 3-octanol relative to substrate, 200 °C, 18 h. Conversion and yields
determined by NMR spectroscopy. Octene-yield based on 3-octanol.
100
80
Y (2,5-DHF)
Y (octenes)
60
X (1,4-AE)
40
20
0
1
2
3
4
5
Run
Figure 5. SEM-EDX mapping: Distribution of Mo on the surface of freshly
prepared MoOx/TiO2 ((NH4)6Mo7O24∙4H2O) [8b] (above), as well as MoOx/TiO2
Figure
4.
Recycling
of
the
in-situ
formed
mixture
[8c]
(NH4)6Mo7O24∙4H2O+TiO2. Conditions: 0.4 mmol 1,4-anhydroerythritol, 5 mol%
Mo in the starting catalyst, and 10 equiv. 3-octanol relative to substrate,
200 °C, 18 h. Conversion and yields determined by NMR spectroscopy.
Octene-yield based on 3-octanol.
((NH4)6Mo7O24∙4H2O)
[8b]
(middle)
and
in-situ
mixture
[8c]
(NH4)6Mo7O24∙4H2O+TiO2 (below) after 5 runs (the corresponding spectra are
shown in SI).
subsequent decrease of the octene formation to
a level
MoOx/TiO2 ((NH4)6Mo7O24∙4H2O) [8b] and after 5 runs further
supporting a high stability upon recycling (SI, Figure S4-S7).
EDX mapping of catalysts after recycling reveals a slightly lower
Mo/Ti ratio and a more uniform Mo distribution in case of in-situ
mixture [8c] (NH4)6Mo7O24∙4H2O+TiO2 (Figure 5 and SI, S6 and
S7, Table S1). Consequently, the nature of Mo aggregation as
well as its uniform and high dispersion are potentially
responsible for the superior catalytic activity of this material
system.
comparable to the in-situ formed catalyst system [8c]. These
results suggest a higher acidity for the impregnated catalyst [8b]
than for the in-situ formed mixture [8c], dropping for every run in
the model reaction. Further studies will focus on the role of
acidity for supported Mo catalysts in DODH. Overall, the
recycling experiments indicate a high stability of the catalyst
material, which could be confirmed by ICP-MS measurement.
The leaching of Mo and Ti during every run was below 0.5 %
(see SI, Table S2 and S3). A hot filtration test supports that the
reaction does not proceed in homogeneous phase as no further
2,5-DHF is generated after filtration (see SI, Figure S10).
Furthermore, freshly prepared MoOx/TiO2 ((NH4)6Mo7O24∙4H2O)
[8b] and both catalysts after 5 runs were analyzed with SEM-
EDX confirming a comparable fine dispersion of Mo species on
the surface of the support (Figure 5). A closer look emphasizes
a slight decrease of the Mo/Ti ratio for freshly prepared
Conclusions
In conclusion, we have developed
a stable and efficient
supported molybdenum catalyst for the DODH of
1,4-anhydroerythritol to 2,5-dihydrofuran. The catalytic activity of
the best currently known molybdenum based DODH-catalyst,
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COMMUNICATION
with chloroform (2 times 2 mL), acetone (2 mL) and again chloroform
(2 mL). The solids were dried under air for 1 h at ambient temperature
and at least 3 h at 130 °C. The residues were weighed and the reaction
scales were recalculated accordingly before re-subjecting them to the
procedure.
ammonium heptamolybdate, was increased noticeably by using
titanium dioxide as support material. The in-situ mixture of
ammonium heptamolybdate with titanium dioxide [8c] resulted in
good catalytic activity, but moderate reproducibility. A higher
reproducibility
was
observed
with
MoOx/TiO2
((NH4)6Mo7O24∙4H2O) [8b], which could be recycled five times
without significant decrease of activity. Additionally, Raman-
spectroscopic and SEM-EDX investigations provided a first
insight in the nature of active species with superior performance
of polynuclear molybdenum compounds compared to
mononuclear ones. Additionally, uniform Mo dispersion appears
to be key.
Acknowledgements
This work was performed as part of the Cluster of Excellence
"Tailor-Made Fuels from Biomass" (DFG EXC 236) funded by
the Excellence Initiative by the German federal and state
governments to promote science and research at German
universities. This work was also partially performed at the Center
for Chemical Polymer Technology CPT, which was supported by
the EU and the federal state of North Rhine-Westphalia (grant
EFRE 30 00 883 02). IM thanks the German Federal
Environmental Foundation for financial support.
Experimental Section
All experiments were performed under dry argon atmosphere using
Schlenk or glovebox techniques. NMR spectra were recorded on a
Bruker Avance II 400 MHz at 23 °C (1H: 400 MHz).
Keywords: molybdenum • heterogeneous • deoxydehydration •
Anhydroerythritol, 3-octanol and mesitylene were purchased from Sigma
Aldrich and used after drying over molecular sieve (4 Å) and degassing.
Molybdenum compounds were purchased from Sigma Aldrich and used
as received. TiO2 ST61120 was purchased from Saint-Gobain NorPro
and pestled before use.
biomass • diol
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The appropriate amount Mo-precursor was dissolved in water (20 mL per
gram support). The appropriate amount of the support was added slowly
and the mixture was stirred 24 h at rt. Afterwards the solvent was
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Half of the product was reduced under H2-flow for 3 h at 300 °C.
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General procedure for deoxydehydration reactions
A thick-walled glass tube with a screw cap was charged in the glovebox
sequentially with the catalyst (18 µmol of Mo), anhydroerythritol and
3-octanol in the given ratio. A magnetic stirring bar was added and the
mixture was stirred for 10 minutes at ambient temperature before it was
inserted into a preheated oil bath. After the given reaction time, the glass
tube was taken from the heating bath and cooled down with cold water.
Mesitylene (23 µL) was added as an internal standard and the mixture
was vigorously shaken. Upon homogenization, an aliquot (roughly
0.05 mL) of the mixture was taken and mixed with 0.5 mL CDCl3. The
mixture was analyzed by 1H-NMR spectroscopy.
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mixture of ammonium heptamolybdate (3.2 mg) and titanium dioxide
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(38 mg) under air and brought into
a glovebox after exchanging
atmosphere to argon. A stock solution of anhydroerythritol and 3-octanol
(560 mg: 20 equiv. of anhydroerythritol per molybdenum,
anhydroerythritol:3-octanol 1:10) and a magnetic stirring bar were added
and the cap was closed tightly. The tubes were placed into a preheated
oil bath at 200 °C and kept stirring for 18 h. Afterwards, the tubes were
taken out of the oil bath cooled down into an ice/water bath. 1 mL CDCl3
was added for dilution and 23 µL mesitylene was added as internal
standard. After filtration aliquots of the resulting solution were taken and
analyzed by 1H NMR spectroscopy. The retained solids were washed
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Entry for the Table of Contents (Please choose one layout)
Layout 1:
COMMUNICATION
More than the sum: We present the
first supported molybdenum catalyst
for deoxydehydration. Interestingly,
the titania supported Mo catalyst
outperforms the molecular
L. Sandbrink, K. Beckerle, I. Meiners,
R. Liffmann, K. Rahimi, J. Okuda* and
R. Palkovits*
Page No. – Page No.
counterparts.
Supported molybdenum catalysts
for the deoxydehydration of 1,4-
anhydroerythritol into 2,5-
dihydrofuran
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