Production of liquid hydrocarbon fuels with 3-pentanone and platform molecules derived from lignocellulose

Article abstract of DOI:10.1039/c6ra14789e

Diesel or jet fuel range C₁₀-C₁₇ branched and cyclic alkanes were produced by reaction of 3-pentanone derived from lactic acid with bio-based aldehydes through aldol condensation followed by hydrodeoxygenation. DBU (1,8-diazabicycloundec-7-ene) was identified as an efficient catalyst for the aldol reaction of 3-pentanone with furan based aldehydes, and the selectivity of single or double aldol condensation product could be easily controlled by adjusting the reaction temperature. For the reaction with aromatic aldehydes, aluminium phosphate demonstrated a higher catalytic activity than DBU and mechanisms were proposed for the difference in the catalytic activity. The final hydrodeoxygenation step could be achieved by using a simple Pd/C + H-beta zeolite system, excellent selectivity was observed under the present system, the clean formation of hydrocarbons with a narrow distribution of alkanes occurred in most cases.

Full text of DOI:10.1039/c6ra14789e

RSC Advances
View Article Online
View Journal | View Issue
PAPER
Production of liquid hydrocarbon fuels with 3-
pentanone and platform molecules derived from
lignocellulose†
Cite this: RSC Adv., 2016, 6, 62974
abc
Tao Shen,ab Chenjie Zhu,
Chenglun Tang,ab Zhi Cao,ab Linfeng Wang,d Kai Guoa
*
abc
*
and Hanjie Ying
Diesel or jet fuel range C10–C17 branched and cyclic alkanes were produced by reaction of 3-pentanone
derived from lactic acid with bio-based aldehydes through aldol condensation followed by
hydrodeoxygenation. DBU (1,8-diazabicycloundec-7-ene) was identified as an efficient catalyst for the
aldol reaction of 3-pentanone with furan based aldehydes, and the selectivity of single or double aldol
condensation product could be easily controlled by adjusting the reaction temperature. For the reaction
with aromatic aldehydes, aluminium phosphate demonstrated a higher catalytic activity than DBU and
mechanisms were proposed for the difference in the catalytic activity. The final hydrodeoxygenation step
could be achieved by using a simple Pd/C + H-beta zeolite system, excellent selectivity was observed
under the present system, the clean formation of hydrocarbons with a narrow distribution of alkanes
occurred in most cases.
Received 7th June 2016
Accepted 27th June 2016
DOI: 10.1039/c6ra14789e
www.rsc.org/advances
important and meaningful when the synthon is derived from
biomass. Recently, we reported the use of acetoin as a novel C4
1 Introduction
building block for the production of C9–C14 liquid hydrocarbon
fuels.19 However, this method suffers from that only straight
alkanes can be obtained aer the reaction with lignocellulose
derived aldehydes. Compared to branched alkanes, these
straight alkanes have lower octane numbers and higher freezing
points, and cannot be directly used as jet fuel without hydro-
isomerization. Furthermore, the production capacity of acetoin
is relatively small compared to the other bulk chemicals.
On the other hand, lactic acid is the most widely occurring
carboxylic acid in nature. Annual production reaches 120 000
tons per year, and 90% of which is produced by bacterial
fermentation of biomass sugars.20 It possesses a rich chemistry
due to its two functional groups (adjacent hydroxyl and
carboxylic groups), numerous transformations of lactic acid into
valuable chemicals such as acetaldehyde via decarbonylation,
acrylic acid via dehydration, 2,3-pentanedione via condensa-
tion, polylactic acid via self-esterication-polymerization,
propanoic acid via reduction, and 3-pentanone via reduction-
ketonization has been reported.21 Among them, 3-pentanone
is a potential bio-based C5 building block for the synthesis of
renewable liquid hydrocarbon fuels due to it possesses ideal
carbon number and a-hydrogen atoms. In the recent work of
Zhang's group,22 it was suggested that single condensation
product C10 fuel precursor 1-(furan-2-yl)-2-methylpent-1-en-3-
one 1a (generated by the condensation of one furfural mole-
cule and one 3-pentanone molecule) could be obtained through
the aldol condensation of furfural and 3-pentanone using CaO
as a solid base catalyst (Scheme 1). However, this method still
Due to the depleting fossil fuel reserves and increasing green-
house gas emission, the exploration of feasible pathways for the
conversion of abundant and renewable biomass into clean fuels
has drawn considerable attention.1–3 In this sense, lignocellu-
losic biomass is a promising candidate due to it being an
abundant and carbon-neutral energy resource.4,5 Catalytic
transformation of platform molecules through an oxygen
removal process (e.g. dehydration, hydrogenation, hydro-
genolysis, decarbonylation) or in some cases along with an
increase in the length of the carbon chain via C–C coupling
reactions (e.g. aldol condensation, hydroxyalkylation, ketoni-
zation, oligomerization) is an important route to convert
lignocellulose into liquid hydrocarbon fuels.6,7 To meet the
number of carbon atoms for the target fuel range, such as diesel
and jet fuels, various reactive intermediates such as acetone,8–11
hydroxyacetone or dihydroxyacetone,12,13 mesityl oxide,14 methyl
isobutyl ketone,15 and butanal16–18 have been employed as syn-
thons for the carbon chain elongation. This route is especially
aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University,
Nanjing, China. E-mail: zhucj@njtech.edu.cn; yinghanjie@njtech.edu.cn; Tel: +86 25
58139389
bNational Engineering Technique Research Center for Biotechnology, Nanjing, China
cJiangsu National Synergetic Innovation Center for Advanced Materials (SICAM),
China
dState Key Laboratory of Motor Vehicle Biofuel Technology, Nanyang, China
† Electronic supplementary information (ESI) available. See DOI:
10.1039/c6ra14789e
62974 | RSC Adv., 2016, 6, 62974–62980
This journal is © The Royal Society of Chemistry 2016

View Article Online
Paper
RSC Advances
Scheme 1 (a) Previous work versus (b) our new protocol for the synthesis of liquid alkanes using 3-pentanone as a bio-based synthon.
has some shortcomings: (i) double condensation product C15 evaporated and puried by column chromatography to provide
precursor 1,5-di(furan-2-yl)-2,4-dimethylpenta-1,4-dien-3-one 2a the analytically pure product for further HDO.
(generated by the condensation of two furfural molecules and
one 3-pentanone molecule) cannot be synthesized through this
method; (ii) low yield of C10 precursor (60%) was achieved due to
the adsorption of furfural on the surface of CaO and other side
reactions; (iii) harsh reaction condition, the reaction need to
carried out at high temperature (443 K). The poor catalytic
efficiency of CaO as well as recent advances in C–C coupling
reactions23 prompted us to reconsider the solid base catalyst
and provided an opportunity of nding a more reactive catalyst.
Herein, we report the highly efficient synthesis of C10–C17
branched and cyclic alkanes from the reaction of 3-pentanone
with lignocellulose derived platform molecules (Scheme 1).
Aldol condensation of 3-pentanone with vanillin
To a solution of 3-pentanone (20 mmol) and vanillin (20 mmol)
was added amorphous aluminium phosphate (0.4 g). The
ꢀ
mixture was stirred at 120 C under solvent-free condition for
12 h. Aer completion, the mixture was diluted with EtOAc and
ALPO was removed by ltration. The obtained organic layer was
evaporated and puried by column chromatography to provide
the analytically pure product for further HDO.
Hydrodeoxygenation (HDO)
Typically, 2a (1,5-di(furan-2-yl)-2,4-dimethylpenta-1,4-dien-3-
one, 2.5 mmol) was dissolved in 25 mL distilled water and
transferred to a 100 mL Parr pressure reactor. To this reactor
was added Pd/C (5 wt%, 0.25 g) and H-beta zeolite (0.25 g). The
reactor was purged thrice with nitrogen and charged to 4 MPa
2 Experimental
Aldol condensation of 3-pentanone with furan aldehyde
For single condensation product: to a solution of 3-pentanone H2. Aer that, the reactor was heated to 200 ꢀC under vigorous
(10 mmol) and furan aldehyde (10 mmol) was added DBU stirring for 8 h. Aer the system reached to room temperature,
(1 mmol), the mixture was stirred at room temperature under the gas was collected in a gas cylinder of known volume and the
solvent-free condition; for double condensation product: to pressure of the gas cylinder was adjusted to 1 atm using high
a solution of 3-pentanone (10 mmol) and furan aldehyde purity nitrogen as a makeup gas. The gaseous products were
(25 mmol) was added DBU (3 mmol), the mixture was stirred at analyzed by GC using methanizer (for CO and CO2) and TCD
80 ꢀC under solvent-free condition. Aer completion, the analyzer (for other gaseous hydrocarbons), and the gas overall
mixture was diluted with EtOAc, the obtained organic layer was yield was determined. Then, the catalysts were removed by
This journal is © The Royal Society of Chemistry 2016
RSC Adv., 2016, 6, 62974–62980 | 62975

View Article Online
RSC Advances
Paper
centrifugation, and the liquid solution was extracted with EtOAc aldol condensation reaction between furfural with acetone,8–11
and analyzed by GC-MS. Alkane selectivity was reported based which probably due to the lower reactivity of a-carbon atoms in
on the percentage of peak areas measured by GC. Total organic 3-pentanone molecule (caused by the steric hindrance and
carbon (TOC) analysis was performed on nal concentrated electron donating properties of the methyl groups attached to a-
liquid organic products to quantify the total carbon present and carbon atoms of 3-pentanone). Under such strong basic
calibrate the GC for reaction products.
condition, other side reactions such as Cannizzaro reaction,
radical polymerization, resinication of furfural, and Michael
addition to the formed enone may also happened during the
reaction,24,25 resulting in generation of some unfavorable poly-
mers. The use of other inorganic base such as Na2CO3 also did
not show any improvement for the present reaction.26
3 Results and discussion
Aldol condensation of 3-pentanone with furfural
Inspired by the pioneering work of Dumesic and Huber
group,8–10 initial experiments for the aldol condensation of
furfural and 3-pentanone was rst carried out using NaOH as
a catalyst, and the molar ratio of furfural to 3-pentanone was
kept constant at 2. According to the NMR and GC-MS spectrum
(Fig. S1 and S8†), the single condensation product 1a was
identied as the main product, only a small quantity of double
condensation product C15 oxygenate 2a (<5%) was detected in
the reaction mixture. Unfortunately, further optimization about
the amount of NaOH, reaction temperature, time, or using
biphasic system did not shown any improvement for the yield of
2a. This result is quite different from previously report about
In order to solve the selectivity issue and improve the yield of
the double condensation product 2a, catalysts including orga-
nocatalysts, and task-specic ionic liquids were tested for the
reaction (Fig. 1). Amine-based organocatalysts such as iPr2NEt,
L-proline, tryptophan, and 1,4-diazabicyclo[2.2.2]octane
(DABCO), failed to catalyze this reaction. The task-specic ionic
liquid catalysts [H3N+–CH2–CH2–OH][CH3COOꢁ] (EAIL) and
[H3N+–CH2–CH2–OH][CH3CH(OH)COOꢁ] (LAIL), which were
previously efficient catalysts for the aldol reaction,19 were also
only able to get the single condensation product 1a. To our
delight, DBU (1,8-diazabicycloundec-7-ene) exhibited excellent
selectivity towards to double condensation product 2a
(Fig. S9†). Encouraged by this result, further optimization of
reaction using DBU as a catalyst were performed (Table 1). The
results show that the yield of 2a increases from 76% to 91% as
the furfural/3-pentanone molar ratio increases from 2 to 3
(Table 1, entries 1–3), which may be caused by the partial of
furfural was consumed from negative side reactions during the
process. With regard to the catalyst dosage, it was possible to
decrease the amount of DBU to as low as 10 mol%, albeit
a longer reaction time was required (Table 1, entry 5). It is
noteworthy that a strong effect of temperature was observed on
the product distribution. The yield of 2a increases up to 90%
when the reaction was performed at room temperature even at
the molar ratio of furfural/3-pentanone is 2.5 (Table 1, entry 6),
which means the selectivity of this reaction is thermodynamic
control versus kinetic control. This nding is very meaningful
due to it offers a useful method to tune the ultimate desired
composition of single or double condensation product. To
check this point, conrmatory experiment was carried out at the
molar ratio of furfural/3-pentanone is 1 at room temperature, as
Fig. 1 Results of the aldol condensation between of 3-pentanone
with furfural over different catalysts (for detailed experimental proto-
cols, see the ESI†).
Table 1 Optimization of aldol condensation of furfural with 3-pentanone catalyzed by DBU
Yielda (%)
Furfural/3-pentanone
(molar ratio)
Entry
DBU loadinga (mol%)
T (ꢀC)
Time (h)
1a
2a
1
2
3
4
5
6
7
2.0
2.5
3.0
2.5
2.5
2.5
1
30
30
30
20
10
10
10
80
80
80
80
80
r.t.
r.t.
12
10
10
14
22
16
48
16
8
7
10
9
90
92
76
88
91
86
84
7
3
a
With respect to the limiting reactant 3-pentanone.
62976 | RSC Adv., 2016, 6, 62974–62980
This journal is © The Royal Society of Chemistry 2016

View Article Online
Paper
RSC Advances
Scheme 2 Proposed pathway for the formation of 2a catalyzed by DBU.
expected, an excellent selectivity was achieved using this similar reaction process to afford the double condensation
method even in the condition of prolonging the reaction time product 2a. As can be seen, DUB plays an important role in the
up to 48 h, and the desired single condensation product 1a can reaction, which not only facilitates the departure of a-H of 3-
be obtained in 92% yield (Fig. S2 and S9†).
pentanone to form the enolate intermediate, but also activates
A plausible mechanism for the formation of 2a is depicted in the furfural through forming hydrogen-bonding network.
Scheme 2. The reaction begins with generation of enolate I by
DBU induced the deprotonation of 3-pentanone, which behaves
Aldol condensation of 3-pentanone with other aldehydes
derived from lignocellulose
as a carbonyl donor to attack furfural, whereby providing the
single condensation product 1a via dehydration of 1a0. The
protonated DBU-H derived from the formation of enolate I can
activate the furfural by increasing the positive charge on the
corresponding carbon atom through hydrogen-bonding
network to promote the above process. The regenerated DBU
then react with 1a to produce enolate II, which undergoes
With the aim to develop and dene the scope and limitation of
the present catalytic system, this procedure was then extended
for the reaction of 3-pentanone with other aldehydes, which
including 5-methylfurfural (5-MF), 5-hydroxymethylfurfural
(HMF) derived from cellulose,27,28 and vanillin derived from
Table 2 The reaction of 3-pentanone with bio-based aldehydes
Entry
Substrate
Product
T (ꢀC)
Time (h)
24
Yield (%)
90
1a
r.t.
2b
3a
4b
80
r.t.
80
8
85
87
73
24
10
5c
120
12
64
a
b
c
Molar ratio of aldehyde/3-pentanone is 1. Molar ratio of aldehyde/3-pentanone is 2.5. Reaction were catalyzed by ALPO under solvent-free
condition.
This journal is © The Royal Society of Chemistry 2016
RSC Adv., 2016, 6, 62974–62980 | 62977

View Article Online
RSC Advances
Paper
ꢀ
ALPO aer reacting at 120 C for 12 h under solvent free condi-
tion (Table 2, entry 5). Unfortunately, further optimization in
order to obtain the C21 double condensation product was
unsuccessful. Although, so far, we cannot be certain of the actual
role of ALPO in this reaction, on the basis of the previous study,30
we believe that the superior behavior of ALPO over DBU catalyst is
due to a combined acid–base synergistic catalysis effect, espe-
cially for the Bronsted acid sites on the surface of ALPO (–POH
group), which could interact with the carbonyl group of vanillin
to produce the corresponding carbocation III (Scheme 3).
Furthermore, the Bronsted acid sites could also enhance the
acidity of a-H by interacting with the carbonyl group of 3-pen-
tanone, which makes it more easier to react with the Lewis basic
sites of ALPO to generate a carbanion species. This should favor
the attack of III derived from the activated vanillin. To check this
point, verication experiment were performed using Na-
exchanged ALPO, in which the acidity was neutralized by treat-
ing ALPO with sodium acetate, and the result showed that no
aldol reaction was occurred using Na-exchanged ALPO, which
provided a strong support towards this mechanism.
Scheme 3 Tentative mechanism for the reaction of 3-pentanone with
vanillin catalyzed by ALPO.
lignin.29 As shown in Table 2, DBU works well for the reaction
with furan aldehydes, 5-MF and HMF underwent smooth trans-
formation to afford their corresponding C11 single condensation
product or C17 double condensation products in moderate to
excellent yields (Table 2, entries 1–4). However, when the
substrate changed to aromatic aldehyde, such as vanillin, and the
corresponding condensation product 7a that could be expected
in analogy with furan aldehyde and 3-pentanone was not detec-
ted aer the reaction, the low activity of vanillin was considered
to be originated from the electron rich property of aromatic ring,
and the activation of the carbonyl group in vanillin only through
hydrogen-bonding network induced by DBUH+ is not sufficient to
trigger the reaction. Aer further screening of catalysts and
optimizing the procedure, we found that replacing DBU with
amorphous aluminium phosphate (ALPO) and increasing the
reaction temperature signicantly promoted the reaction, C13
single condensation product could be obtained over 10 wt% of
Table 3 The structures of the fuel precursors and their theoretical
HDO products
Fuel precursors
Theoretical alkane product
Fig. 2 Carbon selectivity of different products from the HDO of 3a
over Pd/C and different solid acid catalysts. Reaction conditions: Pd/C
(5 wt%, 0.25 g) and solid acid (0.25 g), 200 ꢀC, 4 MPa H2, 8 h. The diesel
range alkanes, gasoline range alkanes and light alkanes account for
C9–C18, C5–C8 and C1–C4 alkanes, respectively.
62978 | RSC Adv., 2016, 6, 62974–62980
This journal is © The Royal Society of Chemistry 2016

View Article Online
Paper
RSC Advances
yield though this effective catalytic system (Fig. S15†), which is
the second most abundant component required in the
commercial and military jet fuels with the mass percent of
20–50 wt%.39,40 Compared to straight alkanes, cyclic alkanes
have higher densities and volumetric heating values due to the
strong ring strain.41,42
Hydrodeoxygenation
As the nal aim of this work, the direct hydrodeoxygenation of
these fuel precursors into alkanes were performed in batch
reactor. The aldol condensation product from 5-MF and
3-pentanone 3a was rst chosen as a model fuel precursor for
this study. In previous works, it was found that supported Pd
catalysts were efficient for the HDO of oxygenate,19,31 thus, this
catalyst was also tested for the present study. According to the
previous research, the dehydration over acid sites followed by
the hydrogenation over metal sites is the major pathway for the
C–O cleavage reaction,32,33 thus, several solid acid such as
NbOPO4, TaOPO4, and ZrP were selected for the purpose of
comparison.34–38 As shown in Fig. 2, NbOPO4, TaOPO4 and ZrP
system tend to have a more selectivity to produce oxygenated
compounds (Fig. S10†). Among them, H-b + Pd/C system
exhibited excellent catalytic performance and highest selectivity
to alkane. The almost clean formation of theoretical alkane
product C11H24 under mild conditions (200 ꢀC and 4 MP H2
pressure) is remarkable (Fig. S11†). Hence, this procedure was
further extended for the HDO of other fuel precursors to check
its applicability (Table 3). As shown in Fig. 3, most substrates
underwent smooth transformation to afford their correspond-
ing theoretical alkane products in moderate to excellent yields,
and the present catalytic system showed high selectivity for the
production of diesel range alkanes. In all cases, these fuel
precursors were completely converted to alkanes and no or
a negligible amount of oxygenates were detected based on GC-
MS analysis. The carbon balance was almost quantitative for
most of the HDO reactions, >90% of the carbon was in the
liquid organic products according to the TOC analysis. It is
noteworthy that excellent selectivity was observed under the
present system, the clean formation of hydrocarbons with
a narrow distribution of alkanes was occurred for most cases
(Fig. S11–S14†). Cyclic alkanes can also be obtained in high
4 Conclusions
In conclusion, a novel C5 building block 3-pentanone derived
from lactic acid has been used as a bio-based synthon for the
production of liquid hydrocarbon fuels. It was found that 1,8-
diazabicycloundec-7-ene and aluminium phosphate were effi-
cient catalysts for the aldol condensation of 3-pentanone with
furan based aldehyde and aromatic aldehyde, respectively. A
series of well-dened diesel or jet fuel range C10–C17 branched
or cyclic alkanes could be produced in excellent yields
under Pd/C
+ H-beta zeolite catalytic system through
hydrodeoxygenation.
Acknowledgements
The authors thank the nancial support by the Program for
Changjiang Scholars and Innovative Research Team in Univer-
sity (Grant No.: IRT_14R28); The National Natural Science
Foundation of China (Grant No.: 21406110) and Jiangsu Prov-
ince Natural Science Foundation for Youths (Grant No.:
BK20140938); The State Key Laboratory of Motor Vehicle Biofuel
Technology (Grant No.: KFKT2013001); Jiangsu National
Synergetic Innovation Center for Advanced Materials (SICAM).
References
1 G. W. Huber, S. Iborra and A. Corma, Chem. Rev., 2006, 106,
4044–4098.
2 D. M. Alonso, J. Q. Bond and J. A. Dumesic, Green Chem.,
2010, 12, 1493–1513.
3 D. A. Simonetti and J. A. Dumesic, Catal. Rev.: Sci. Eng., 2009,
51, 441–484.
4 C. Somerville, H. Youngs, C. Taylor, S. C. Davis and
S. P. Long, Science, 2010, 329, 790–792.
5 C. Zhou, X. Xia, C. Lin, D. Tong and J. Beltramini, Chem. Soc.
Rev., 2011, 40, 5588–5617.
6 M. J. Climent, A. Corma and S. Iborra, Green Chem., 2014, 16,
516–547.
7 A. Bohre, S. Dutta, B. Saha and M. M. Abu-Omar, ACS
Sustainable Chem. Eng., 2015, 3, 1263–1277.
8 G. W. Huber, J. N. Chheda, C. J. Barrett and J. A. Dumesic,
Science, 2005, 308, 1446–1450.
¨
9 R. M. West, Z. Y. Liu, M. Peter, C. A. Gartner and
J. A. Dumesic, J. Mol. Catal. A: Chem., 2008, 296, 18–27.
10 R. Xing, A. V. Subrahmanyam, H. Olcay, W. Qi,
G. P. V. Walsum, H. Pendse and G. W. Huber, Green
Chem., 2010, 12, 1933–1946.
11 A. D. Sutton, F. D. Waldie, R. Wu, M. Schlaf, L. A. P. Silks and
J. C. Gordon, Nat. Chem., 2013, 5, 428–432.
Fig. 3 Carbon yield of different alkanes from the HDO of different
precursors over the Pd/C + H-b system. The diesel range alkanes,
gasoline range alkanes and light alkanes account for C9–C18, C5–C8
and C1–C4 alkanes, respectively.
This journal is © The Royal Society of Chemistry 2016
RSC Adv., 2016, 6, 62974–62980 | 62979

View Article Online
RSC Advances
Paper
12 A. V. Subrahmanyam, S. Thayumanavan and G. W. Huber, 27 W. Yang and A. Sen, ChemSusChem, 2011, 4, 349–352.
ChemSusChem, 2010, 3, 1158–1161.
13 G. Li, N. Li, S. Li, A. Wang, Y. Cong, X. Wang and T. Zhang,
Chem. Commun., 2013, 49, 5727–5729.
28 R. J. van Putten, J. C. van der Waal, E. de Jong,
C. B. Rasrendra, H. J. Heeres and J. G. de Vries, Chem.
Rev., 2013, 113, 1499–1597.
14 S. Li, N. Li, G. Li, A. Wang, Y. Cong, X. Wang and T. Zhang, 29 P. C. R. Pinto, C. E. Costa and A. E. Rodrigues, Ind. Eng.
Catal. Today, 2014, 234, 91–99. Chem. Res., 2013, 52, 4421–4428.
15 J. Yang, N. Li, W. Wang, A. Wang, X. Wang, Y. Cong and 30 M. J. Climent, A. Corma, H. Garcia, R. Guil-Lopez, S. Iborra
´
and V. Fornes, J. Catal., 2011, 197, 385–393.
T. Zhang, ChemSusChem, 2013, 6, 1149–1152.
16 A. Corma, O. D. L. Torre, M. Renz and N. Villandier, Angew. 31 Z. Xue, X. Sun, Z. Li and T. Mu, Chem. Commun., 2015, 51,
Chem., Int. Ed., 2011, 50, 2375–2378. 10811–10814.
17 A. Corma, O. de la Torre and M. Renz, Energy Environ. Sci., 32 N. Li and G. W. Huber, J. Catal., 2010, 270, 48–59.
2012, 5, 6328–6344.
18 G. Li, N. Li, J. Yang, A. Wang, X. Wang, Y. Cong and T. Zhang,
Bioresour. Technol., 2013, 134, 66–72.
19 C. Zhu, T. Shen, D. Liu, J. Wu, Y. Chen, L. Wang, K. Guo,
H. Ying and P. Ouyang, Green Chem., 2016, 18, 2165–2174.
20 R. Datta and M. Henry, J. Chem. Technol. Biotechnol., 2006,
81, 1119–1129.
21 Y. Fan, C. Zhou and X. Zhu, Catal. Rev.: Sci. Eng., 2009, 51,
293–324.
33 S. De, B. Saha and R. Luque, Bioresour. Technol., 2015, 178,
108–118.
34 G. Li, N. Li, Z. Wang, C. Li, A. Wang, X. Wang, Y. Cong and
T. Zhang, ChemSusChem, 2012, 5, 1958–1966.
35 Y.-B. Huang, Z. Yang, J.-J. Dai, Q.-X. Guo and Y. Fu, RSC Adv.,
2012, 2, 11211–11214.
36 Q.-N. Xia, Q. Cuan, X.-H. Liu, X.-Q. Gong, G.-Z. Lu and
Y.-Q. Wang, Angew. Chem., Int. Ed., 2014, 53, 9755–9760.
37 Z. Xue, Y. Zhang, G. Li, J. Wang, W. Zhao and T. Mu, Catal.
Sci. Technol., 2016, 6, 1070–1076.
22 F. Chen, N. Li, S. Li, J. Yang, F. Liu, W. Wang, A. Wang,
Y. Cong, X. Wang and T. Zhang, Catal. Commun., 2015, 59, 38 Z. Xue, J. Jiang, G. Li, W. Zhao, J. Wang and T. Mu, Catal. Sci.
229–232.
Technol., 2016, DOI: 10.1039/c5cy02215k.
23 E. F. Iliopoulou, Curr. Org. Synth., 2010, 7, 587–598.
24 H. Olcay, A. V. Subrahmanyam, R. Xing, J. Lajoie,
J. A. Dumesic and G. W. Huber, Energy Environ. Sci., 2013,
6, 205–216.
39 E. Corporan, T. Edwards, L. Shafer, M. J. DeWitt,
C. Klingshirn, S. Zabarnick, Z. West, R. Striebich,
J. Graham and J. Klein, Energy Fuels, 2011, 25, 955–966.
40 P. Bi, J. Wang, Y. Zhang, P. Jiang, X. Wu, J. Liu, H. Xue,
T. Wang and Q. Li, Bioresour. Technol., 2015, 183, 10–17.
25 A. Gandini, The Behaviour of Furan Derivatives in
Polymerization Reaction in Advances in Polymer Science, 41 H. A. Meylemans, R. L. Quintana, B. R. Goldsmith and
Springer, Berlin, 1977, vol. 25, pp. 47–96. B. G. Harvey, ChemSusChem, 2011, 4, 465–469.
26 Y. Zhang, Z. Xue, J. Wang, X. Zhao, Y. Deng, W. Zhao and 42 J. Yang, N. Li, G. Li, W. Wang, A. Wang, X. Wang, Y. Cong
T. Mu, RSC Adv., 2016, 6, 51229–51237.
and T. Zhang, Chem. Commun., 2014, 50, 2572–2574.
62980 | RSC Adv., 2016, 6, 62974–62980
This journal is © The Royal Society of Chemistry 2016