DOI: 10.1002/cssc.

201500178 Communications

One-step Conversion of Furfural into 2-Methyl-

tetrahydrofuran under Mild Conditions
Fang Dong,[a, b] Yulei Zhu,*[a, c] Guoqiang Ding,[c] Jinglei Cui,[a, b] Xianqing Li,[c] and
Yongwang Li[a, c]

One-step direct conversion of biomass-derived furfural to 2- and the process was commercialized.[8, 12–14] However, the fol-
methyltetrahydrofuran was realized under atmospheric pres- lowing two steps faced several problems, that is, limited large-
sure over a dual solid catalyst based on two-stage-packed Cu– scale production of 2-MTHF [including the direct conversion of
Pd in a reactor; this is the first report that one-step conversion furfural to 2-MTHF necessitating a high H2 pressure
of furfural resulted in high yield of 2-methyltetrahydrofuran (> 8.0 MPa)] and the multi-step conversion requiring multi-
(97.1 %) under atmospheric pressure. This strategy provided component catalysts, at least two different reactors, and the
a successive hydrogenation process, which avoids high H2 isolation systems for the intermediates.[15, 16] In a patent, it was
pressure, uses the reactor efficiently, and eliminates the prod- reported that the conversion could also be realized by a two
uct-separation step. Therefore, it could enhance the overall ef- step conversion of furfural, for which two reactors and two cat-
ficiency as a result of low cost and high yield. alysts are required.[7] In the first reactor, furfural was converted
into 2-MF, then the crude product 2-MF was isolated and puri-
fied through a separation system. Following the second step,
Currently, the development and utilization of the biomass- hydrogenation was performed in another reactor with the puri-
based carbon resources is vitally critical for the sustainable pro- fied intermediate 2-MF as feed (reactant). Although this pro-
duction of transportation fuels and chemical substan-
ces.[1–3] Biomass-based synthesis of 2-methyltetrahy-
drofuran (2-MTHF) has gained significant attention as
an approved gasoline additive with excellent com-
bustion properties, as a versatile new-style solvent
with broad application in organic chemistry and in
the commercial resin industry, and also as an impor-
tant medical intermediate.[4, 5] Generally, 2-MTHF is de-
rived from lignocellulose, which is a promising bio-
mass-based alternative in the search for environmen-
tally benign synthesis strategies.[6, 7] The conversion of
lignocellulose into 2-MTHF is achieved by a multistep
conversion, including an acid-catalyzed hydrolysis of
lignocellulose (pentose) to furfural, followed by hy-
drogenation–deoxygenation of furfural to 2-methyl-
furan (2-MF) and further hydrogenation of 2-MF to 2-
MTHF in several separated reaction systems
(Scheme 1).[8–11] For the conversion of lignocellulose
into furfural (the first step reaction for the conversion
Scheme 1. Synthesis pathways of 2-methyltetrahydrofuran through the conversion of
of lignocellulose to 2-methyltetrahydrofuran), a high lignocellulose.
yield of furfural was achieved over various catalysts,
cess could avoid high H2 pressures, it would consume a great
[a] Dr. F. Dong, Prof. Y. Zhu, Dr. J. Cui, Prof. Y. Li deal of energy and material and reduce the yield of the overall
State Key Laboratory of Coal Conversion
process. Thus, it would produce some negative effects on the
Institute of Coal Chemistry, Chinese Academy of Sciences
Taiyuan 030001 (PR China) economy of the 2-MTHF industry.
E-mail: [email protected] To the best our knowledge, there are only few reports on
[b] Dr. F. Dong, Dr. J. Cui the one-step conversion of furfural to 2-MTHF in a reactor
Graduate University of Chinese Academy of Sciences under atmospheric pressure. Especially high H2 pressure and
Beijing 100039 (PR China)
the multiple reaction systems are the reasons limiting the
[c] Prof. Y. Zhu, Dr. G. Ding, X. Li, Prof. Y. Li
large-scale production of 2-MTHF via biomass conversion be-
Synfuels China Co. Ltd.
Taiyuan 030032 (PR China) cause the whole process is difficult to control and requires
Supporting Information for this article is available on the WWW under a great deal of energy to complete, thus reducing the overall
http://dx.doi.org/10.1002/cssc.201500178. efficiency and yield of hydrogenation reaction.

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Herein, a new continuous process is realized for the synthe- duction temperature of Cu and Ni metals is discordant, so Cu-
sis of 2-MTHF via the direct conversion of furfural under mild and Pd-based catalysts would be the better choice for the suc-
conditions that avoids the use of multiple reactors. We de- cessive hydrogenation of furfural to 2-MTHF. Our previous
signed a successive process for the synthesis of 2-MTHF under work suggested that Cu/SiO2 catalyst performs excellently in
atmospheric pressure, in which the conversion of intermedi- the hydrogenation–deoxygenation of the C=O bonds in furfu-
ates can be controlled efficiently on the basis of the nature of ral (Figure S2).[22] Herein, we investigated the operation of Cu-
the functional groups in furfural and especially through the based (copper phyllosilicate = Cu2Si2O5(OH)2) and Pd-based
method of packing the reactor with the catalyst. Interestingly, (Pd/SiO2) catalysts; the results indicated that both
when the continuous fixed-bed reactor was fed with pure fur- Cu2Si2O5(OH)2 and Pd/SiO2 had a poor selectivity towards the
fural, the yield of desired product 2-MTHF was high (up to desired product 2-MTHF (Table 1, entries 1 and 2). For
97.1 %) for an optimized packing of the dual solid catalysts Cu2Si2O5(OH)2, the main product was 2-MF (yield = 84.6 %)
Cu–Pd under atmospheric pressure. From the perspective of above 170 8C, which derived from the hydrogenation–deoxyge-
energy consumption, this technology is also economical and nation of the CH=O bonds in furfural and exhibited an out-
greatly reduces the cost of product separation as the products standing hydrogenation ability of the CH=O bonds (Fig-
are automatically isolated in the two-phase oil–water-based ure S3). However, on Pd/SiO2, the major products were tetrahy-
system (low solubility of 2-MTHF in water; Figure S1 in the drofurfuryl alcohol at low temperature and furan at high tem-
Supporting Information). Furthermore, we also performed a de- perature, which derived from the hydrogenation of the C=C
tailed investigation of the performance of various catalysts and bonds and the breaking of C C bands in furfural (the breaking
the influence of reaction conditions on the synthesis of 2- of furan ring and CH=O; Figure S4). To verify the outstanding
MTHF. hydrogenation performance of Pd/SiO2 for the C=C bonds, 2-
The hydrogenation process from furfural to 2-MTHF was in- MF was used as a reactant on Pd/SiO2 as only C=C bonds exist
vestigated in a continuous fixed-bed reactor over various cata- in 2-MF, which could be efficiently converted into 2-MTHF with
lysts (Figure S2 and Table 1). Furfural possesses both C=C and a 98.6 % selectivity (Table 1, entry 3). These results verified that
C=O bonds and is a type of a,b-unsaturated compound, which the Cu-based catalyst performed well in the hydrogenation–
was treated as a good model compound for studying the se- deoxygenation of the CH=O bonds whereas the Pd-based
lective hydrogenation of C=C and C=O bonds. Therefore, the catalyst efficiently hydrogenated the C=C bonds. Afterwards,
selective conversion of functional groups from furfural plays an the bimetallic CuPd (supported on SiO2) catalyst was synthe-
important role in the field of biomass conversion.[17] Crucially, tized and tested for the direct conversion of furfural into 2-
the conversion of furfural to 2-MTHF demands the hydrogena- MTHF. Unfortunately, CuPd/SiO2 had a high selectivity for 2-MF
tion–deoxygenation of the CH=O bonds and the hydrogena- and furfuryl alcohol due to the conversion of the CH=O
tion of the C=C bonds in the furan ring (Scheme 1). Generally, bonds (Table 1, entry 4), suggesting that the hydrogenation of
Cu-based catalysts are superior to some conventional hydroge- the CH=O bonds is superior to that of the C=C bonds of the
nation catalysts in the hydrogenation–deoxygenation of the furan ring in furfural. Based on the above results, we designed
CH=O bonds,[18, 19] and Ni/Pd-based catalysts play a significant an integral process using two-stage packing of Cu2Si2O5(OH)2
role in the selective hydrogenation of C=C bonds.[20, 21] There- and Pd/SiO2 as catalysts (dual solid Cu–Pd catalysts) in a reactor,
fore, Cu/Ni/Pd-based catalysts might be excellent catalysts for which depends mainly on the good catalytic performance of
the direct conversion of furfural to 2-MTHF. However, the re- the Cu-based catalyst in the synthesis of 2-MF and the subse-
quent C=C bond hydrogenation
of 2-MF to 2-MTHF on Pd/SiO2
(Scheme S1).
Table 1. The hydrogenation of furfural over various catalysts.[a]
Notably, the method of pack-
Catalysts Conv. Selectivity [%] ing of the dual solid Cu–Pd cata-
lyst significantly affected the hy-
[%] THF + FU others drogenation sequence of the
CH=O and C=C bonds and fur-
Cu2Si2O5(OH)2 94.4 0.8 84.6 0.1 5.4 0 9.1 ther influences product selectivi-
Pd/SiO2 99.3 0.4 0.1 1.3 12.9 84.8 0.5
Pd/SiO2[b] 88.9 98.6 0 0 0 0 1.4 ty. It was discovered that when
CuPd/SiO2[c] 88.7 1.6 66.1 20.9 4.7 0.1 6.6 the upper of reactor was packed
Cu2Si2O5(OH)2 + Pd/SiO2[d] 97.5 85.5 4.1 0.3 9.8 0 0.3 with Cu2Si2O5(OH)2 and catalyst
Pd/SiO2 + Cu2Si2O5(OH)2[e] 99.5 1.6 43.4 0 21 28.9 5.1 and Pd/SiO2 was at the bottom
[f]
Cu2Si2O5(OH)2 + Pd/SiO2 99.1 14.9 65.6 0.8 12.9 1.2 4.6
of the reactor, a 85.5 % selectivi-
[a] Reaction conditions: atmospheric pressure, 170 8C, H2/furfural (molar ratio) = 29, weight hourly space veloci- ty to 2-MTHF was obtained
ty (WHSV) = 0.19 h 1, Cu2Si2O5(OH)2 = 1.5 g, Pd/SiO2 = 1.5 g, FU: furan, THF: tetrahydrofuran, others: 2-potanone
(Table 1, entry 5). Contrarily,
(2-PO), 2-pentanol (2-PL), 1-pentanol (1-PL), tetrahydrofurfural, furfural polymers. [b] Reactant is 2-MF. [c] CuPd
bimetal catalyst: palladium was impregnated on Cu phyllosilicate precursor. [d] The upper reactor was packed when Pd/SiO2 catalyst was in the
with Cu phyllosilicate as catalyst, and the bottom reactor was packed with Pd/SiO2 as catalyst. [e] The upper re- upper part of the reactor, tetra-
actor was packed with Pd/SiO2 as catalyst, and the bottom reactor was packed with Cu phyllosilicate as cata- hydrofurfuryl alcohol and tetra-
lyst. [f] Cu phyllosilicate and Pd/SiO2 catalysts were mechanically mixed.
hydrofuran were selectively ob-

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 Communications
tained through the hydrogenation of the C=C bonds and the
breaking of C C bonds (Table 1, entry 6). To further illustrate
the importance of the packing method of the catalysts,
Cu2Si2O5(OH)2 and Pd/SiO2 catalysts were mechanically mixed,
and it was found that the selectivity reaction to 2-MTHF was
much lower than for two-stage packing of the dual solid Cu–
Pd catalyst (Table 1, entry 7). The molar ratio of H2/furfural
(mol/mol) was also investigated in our system. When the molar
ratio of H2/furfural was 29, the selective formation of 2-MTHF
was the highest (Figure S5), which might be ascribed to the
number of activated hydrogen atoms on the catalyst surface.
Sitthisa et al.[23] and Zhang et al.[24] reported that Pd-based
catalysts could hydrogenate the C=C and C=O bonds at low
temperature but would eliminate the C=O bonds (through the
breaking of C C bonds) from furfural at high temperature. In
this work, we also investigated in detail the catalytic per-
Figure 1. Influence of reaction temperature on catalytic performance of Cu–
formance of copper phyllosilicate and Pd/SiO2 at different reac-
Pd dual solid catalysts. Reaction conditions: atmospheric pressure, H2/Furfu-
tion temperatures using furfural as feed (Figures S3 and S4), ral = 29, WHSV = 0.19 h 1, the upper of reactor: Cu2Si2O5(OH)2 = 1.5 g, the
and the result is in accordance with the former reports. There- bottom of reactor: Pd/SiO2 = 1.5 g, THFA: tetrahydrofurfuryl alcohol.
fore, it was considered that the reaction temperature is vitally
important for the hydrogenation–deoxygenation of the CH=
O bonds and the hydrogenation of the C=C bonds on the dif- 2.0 g Pd/SiO2 at the bottom of the reactor. This is related to
ferent metals. At low temperature, the Cu-based catalyst was the number of active sites and the different selectivities of the
responsible for the hydrogenation of the CH=O bonds, but different metals for the conversion of functional groups in fur-
was hardly active for the breaking (deoxygenation) of the fural. Furfural was first converted to 2-MF over Cu2Si2O5(OH)2 in
CH=O bonds. Similarly, Pd/SiO2 performed well in the hydro- the upper part of the reactor and then further converted to 2-
genation of the C=C and CH=O bonds at low temperature, MTHF over Pd/SiO2 catalyst at the bottom of reactor. When the
with the main product being tetrahydrofurfuryl alcohol. Naka- number of Pd sites is too small for the complete hydrogena-
gawa and Tomishige[25] also reported that the yield of 2,5-bis tion of the C=C bonds, the intermediate 2-MF could not be
(hydroxymethyl) tetrahydrofuran obtained from the hydroge- completely converted into 2-MTHF. It was found that 2-MF se-
nation of the CH=O and C=C bonds in 5-hydroxymethyl-2-fur- lectivity was roughly 23.4 % at 0.5 g packing of Pd/SiO2
aldehyde reached 96 % over a co-impregnation of Ni/Pd cata- (Table 2, entry 1). On the other hand, when there are not
lyst. Contrarily, at high temperature, Cu-based catalysts pro- enough Cu sites (0.5 g Cu2Si2O5(OH)2 + 2.5 g Pd/SiO2), furfural
moted the breaking (deoxygenation) of the CH=O bonds, could be not completely converted to 2-MF, which is then fur-
which is advantageous for the selective conversion of furfural ther transformed to other products, such as furan and tetrahy-
into 2-MF.[18, 23] However, the high reaction temperature is un- drofuran, by the breaking of the C C bonds in furfural in
favorable for the hydrogenation of C=C bonds over the Pd- (Table 2, entry 4). Therefore, a suitable packing mass of the
based catalyst as a result of side reactions occurring, such as two-stage catalyst is extremely important for improving the se-
the formation of furan and tetrahydrofuran, which stemmed lectivity of desired product 2-MTHF.
from the breaking of C C bonds (Figure 1). It was discovered In summary, a highly efficiency process for the synthesis of
that the best reaction temperature was 180 8C, at which the se- 2-methyltetrahydrofuran (2-MTHF) from biomass-derived furfu-
lectivity towards 2-MTHF formation reached up to 93.3 %. ral was achieved by means of a two-stage packing of a dual
Moreover, a decrease in selectivity at a higher temperature solid Cu–Pd catalyst under atmospheric pressure. Compared
(200 8C) was related to the for-
mation of undesired by-prod-
ucts, such as pentanol and pen- Table 2. The effect of packing mass on product selectivity over dual solid catalysts based on two-stage-packed
tanone, which were formed Cu–Pd.[a]
through the hydrogenolysis of 2-
Packing mass [g + g] Conv. Selectivity [%]
MF and 2-MTHF.[26]
Furthermore, the packing (Cu2Si2O5(OH)2 + Pd/SiO2) [%] THF + FU others
mass of the two-stage catalysts
was investigated (Table 2 by 2.5 + 0.5 99.1 68.6 23.4 6.5 0.6 0.1 0.8
varying the catalyst mass, and 1.5 + 1.5 98.4 93.3 4.7 0 0.4 0 1.6
the yield of 2-MTHF was as high 1.0 + 2.0 100 97.1 1.4 0 0 0.6 0.9
0.5 + 2.5 100 76.1 21.2 0.5 0 1.2 1.0
as 97.1 % over 1.0 g
Cu2Si2O5(OH)2 catalyst in the [a] Reaction conditions: atmospheric pressure, T = 180 8C, H2/furfural = 29, WHSV = 0.19 h 1, the upper reactor
was packed with Cu2Si2O5(OH)2 as catalyst, the bottom reactor was packed with Pd/SiO2 as catalyst.
upper part of the reactor and

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 Communications
with the single reaction process, this strategy provided a suc-
Keywords: biomass conversion · copper · deoxygenation ·
cessive hydrogenation process by avoiding a high H2 pressure,
hydrogenation · palladium
by using the reactor efficiently, and by eliminating the prod-
uct-separation step. Therefore, it could enhance the overall ef-
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5266.
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This work was supported by the Major State Basic Research De- Received: February 3, 2015
velopment Program of China (973 Program) (No.2012CB215305). Published online on && &&, 0000

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COMMUNICATIONS
Furfural in bed with two catalysts: F. Dong, Y. Zhu,* G. Ding, J. Cui, X. Li, Y. Li
One-step conversion of biomass-derived
&& – &&
furfural to 2-methyltetrahydrofuran (2-
MTHF) is realized over dual solid cata- One-step Conversion of Furfural into
lysts based on two-stage-packed Cu–Pd 2-Methyl-
in a reactor. 2-MTHF yield is as high as tetrahydrofuran under Mild
97.1 % at atmospheric pressure and Conditions
180 8C, which is the highest value re-
ported so far. This strategy provides
a successive hydrogenation by avoiding
high H2 pressure, using the reactor effi-
ciently, and eliminating the product-sep-
aration step.

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