Green Chemistry
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carbocation whose subsequent dehydration followed by
hydrogenation in the presence of H gave 2-MTF under the
acidulation of the reaction system by the autoprotolysis of
ethanol/H O. (c) The formed 2-MTF on the Ni-Sn alloy surface
then was partially hydrogenated to form 2-methyl-4,5-
dihydrofuran (2M4,5DHF) that either was further
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hydrogenated to 2MTHF under rich H gas or hydrolysed to 2. (a) P. Werle, M. Morawietz, S. Lundmark, K. Sörensen, E.
2
H2MTHF; the latter product equilibrated through ring-chain
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tautomerism with hydroxyketone (5H2PeO), which was easily
hydrogenated to 1,4-PeD. Bulk Ni-Sn alloy catalysts consisting
of Ni Sn or Ni Sn alloy phases are responsible for the
3 3 2
enhanced yield of 1,4-PeD. The outstanding yields of 1,4-PeD
up to 92% (from FFald), 67% (from FFalc), and 48% (from 2-
MTF) were achieved in ethanol/H
with 433 K, 3.0 MPa H and 12 h as the optimised reaction
conditions. As the reaction temperature increased to 453 K, 4. W. Xu, H. Wang, X. Liu, J. Ren, Y. Wang, G. Lu, Chem. Commun.,
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2
O (1.5: 2.0 volume ratio) 3. (a) H. Adkins, R. Connor, J. Am. Chem. Soc., 1931, 53, 1091. (b)
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L. E. Schniepp, H. H. Geller, J. Am. Chem. Soc., 1946, 68, 1646.
activity and selectivity after regeneration by H
73 K.
2
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Abbreviations
FFald
FFalc
Furfuraldehyde
Furfuryl alcohol
THFalc
Tetrahydrofurfuryl alcohol
2-Methylfuran
2-Methyltetrahydrofuran
2-Hydroxy-2-methyltetrahydrofuran
2-Methyl-4,5-dihydrofuran
5-Hydroxy-2-pentanone
1,2-Pentanediol
2
2
2
2
5
1
1
1
-MTF
-MTHF
H2MTHF
M4,5DHF
H2PeO
,2-PeD
,4-PeD
,5-PeD
8
9
. G. J. Leuck, J. Pokorny, and F.N. Peters, U.S. Patent 2,097,493.
Nov 2, 1937.
. (a) L. E. Schniepp, H. H. Geller, R. W. Von Korff, J. Am. Chem.
Soc., 1947, 69, 672. (b) K. Topchiev, Compt. Rend. Acad. Sci.
U. R. S. S. 1938, 19, 497. [C. A., 82, 8411 (1938)].
1,4-Pentanediol
1,5-Pentanediol
1
0. F. Liu, Q. Liu, J. Xu, L. Li, Y.-T. Cui, R. Lang, L. Li, Y. Su, S. Miao, H.
Sun, B. Qiao, A. Wang, F. Jerome, and T. Zhang, Green Chem.,
PeOH
Pentanol
2
018, 20, 1770.
1
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Conflicts of interest
This manuscript was written through contributions of all
authors. All authors have given approval to the final version of
the manuscript. There are no conflicts to declare.
2
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Acknowledgements
1
6, 531.
The authors acknowledge the JSPS-DGHE through the Joint Bilateral
Research Project FY 2014-2017, KLN and the International
Publication Project of DGHE FY 2015-2017, the Insentif Riset
Nasional (Insinas) FY 2016-2017, and Hibah Penelitian Berbasis
Kompetensi FY 2018 from the Ministry of Research, Technology,
and Higher Education, which all financially supported this work.
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