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RSC Advances
Page 5 of 7
DOI: 10.1039/C5RA24319J
Journal Name
ARTICLE
OH
OC2H5
-C2H5OH
+
O
5
J. Hegner, K. C. Pereira, B. DeBoef and B. L. Lucht,
+
O
O
O
C2H5OH
C2H5OH
C2H5O
Tetrahedron Lett., 2010, 51, 2356-2358.
- H2O
1,4-addition
6
J. J. Bozell and G. R. Petersen, Green Chem., 2010, 12,
FA
1
2
3
539-554.
O
OH
+
O
+
O
7
C. Chang, G. Xu and X. Jiang, Bioresour. Technol., 2012,
121, 93-99.
H shift
C2H5
O
- H+
+ H2
O
O
C2H5
C2H5
5
EL
O
4
OH
8
J. Zhang, S. Wu, B. Li and H. Zhang, ChemCatChem,
Scheme 2. A possible pathway of the alcoholysis process of FA
to EL.
2012, 4, 1230-1237.
9
M. Chia and J. A. Dumesic, Chem. Commun., 2011, 47,
Based on the observation above, a plausible mechanism of
the alcoholysis process of FA to EL is presumably similar to the
previous reports 15, 32. As is illustrated in Scheme 2, FA first
12233-12235.
10
11
12
H. J. Bart, J. Reidetschlager, K. Schatka and A. Lehmann,
Ind. Eng. Chem. Res., 1994, 33, 21-25.
reacted with ethanol to produce intermediate
subsequent loss of ethanol to give . Next, the obtained cation
underwent nucleophilic conjugate 1,4-addition of ethanol to
give species . Species was formed by a hydrogen shift from
. Finally, H2O as nucleophile attacked species to produce
1, and
Y. Yang, C. Hu and M. M. Abu-Omar, Bioresour.
Technol., 2012, 116, 190-194.
2
2
WO8002423-A1;
BE883067-A;
WO8002423-A;
3
4
US4236021-A; BR8008666-A; EP28234-A; JP56500451-
A; CA1140579-A; IT1141938-B, 1980.
3
4
5,
and then isomerization to obtain desired EL.
13
14
15
16
Y.-B. Huang, T. Yang, M.-C. Zhou, H. Pan and Y. Fu,
Green Chem., 2015, DOI: 10.1039/c5gc01581b.
J. P. Lange, W. D. van de Graaf and R. J. Haan,
Conclusions
ChemSusChem, 2009,
Z. Zhang, K. Dong and Z. K. Zhao, ChemSusChem, 2011,
, 112-118.
16. P. Neves, S. Lima, M. Pillinger, S. M. Rocha, J.
2, 437-441.
We explored an efficient method for the production of
levulinate esters by the alcoholysis process of biomss-derived
furfuryl alcohol over commercial α-Fe2O3. Among the alcohol
substrates test, the highest yield of 73%, 83% and 86% of
corresponding methyl levulinate, ethyl levulinate and n-butyl
levulinate were achieved, respectively under optimal reaction
conditions. On the basis of the investigation of intermediates
and the role of water and its amount, a plausible mechanism
was proposed. The present study provides a fast, efficient and
environmentally friendly method for the conversion of
biomass-based compounds to value-added chemicals.
4
Rocha and A. A. Valente, Catal. Today, 2013, 218-219
,
76-84.
17
18
P. Neves, M. M. Antunes, P. A. Russo, J. P. Abrantes, S.
Lima, A. Fernandes, M. Pillinger, S. M. Rocha, M. F.
Ribeiro and A. A. Valente, Green Chem., 2013, 15
,
3367-3376.
P. A. Russo, M. M. Antunes, P. Neves, P. V. Wiper, E.
Fazio, F. Neri, F. Barreca, L. Mafra, M. Pillinger, N. Pinna
and A. A. Valente, J. Mater. Chem. A, 2014, 2, 11813-
11824.
19
20
21
22
23
24
25
26
27
28
29
S. Zhu, C. Chen, Y. Xue, J. Wu, J. Wang and W. Fan,
ChemCatChem, 2014, , 3080-3083.
Acknowledgements
6
The authors gratefully acknowledge the financial support from
the State Key Program of National Natural Science Foundation
of China (No. 21436007). Key Basic Research Projects of
Science and Technology Commission of Shanghai
(14JC1403100). The Program for Professor of Special
Appointment (Eastern Scholar) at Shanghai Institutions of
Higher Learning (ZXDF160002). We thank the all reviewers and
editors for reviewing the manuscript and providing valuable
comments.
B. Lu, S. An, D. Song, F. Su, X. Yang and Y. Guo, Green
Chem., 2015, 17, 1767-1778.
A. M. Hengne, S. B. Kamble and C. V. Rode, Green
Chem., 2013, 15, 2540-2547.
G. Wang, Z. Zhang and L. Song, Green Chem., 2014, 16
,
1436-1443.
T. P. Pham, C. W. Cho and Y. S. Yun, Water Res., 2010,
44, 352-372.
L. Xu, Z. Huo, J. Fu and F. Jin, Chem. Commun., 2014,
50, 6009-6012.
Y. S. Adam, Y. Fang, Z. Huo, X. Zeng, Z. Jing and F. Jin,
Res. Chem. Intermediat., 2015, 41, 3201-3211.
F. Wang, Y. Wang, F. Jin, G. Yao, Z. Huo, X. Zeng and Z.
Jing, Ind. Eng. Chem. Res., 2014, 53, 7939-7946.
M. Besson, P. Gallezot and C. Pinel, Chem. Rev., 2014,
114, 1827-1870.
Notes and references
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This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
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