ChemSusChem
10.1002/cssc.201601727
FULL PAPER
-
1
pumped into the reactor at 0.04 mL min from the bottom along with
[5]
a) H. Zhao, J. E. Holladay, H. Brown, Z. C. Zhang, Science 2007, 316,
1597-1600; b) R. Weingarten, A. Rodriguez-Beuerman, F. Cao, J. S.
Luterbacher, D. M. Alonso, J. A. Dumesic, G. W. Huber,
ChemCatChem 2014, 6, 2229-2234.
-
1
hydrogen at a flow rate of 120 mL min . After coming out from the tubular
reactor, the products became two phases in a gas-liquid separator. The
gaseous products flowed through a back pressure regulator to maintain
the system pressure at 6 MPa and were analyzed online by an Agilent
890N GC. The liquid products were drained periodically from the gas-
liquid separator and analyzed by an Agilent 7890A GC.
[6]
[7]
B. G. Harvey, H. A. Meylemans, J. Chem. Technol. Biotechnol. 2011,
86, 2-9.
6
H.-Y. Zheng, Y.-L. Zhu, B.-T. Teng, Z.-Q. Bai, C.-H. Zhang, H.-W.
Xiang, Y.-W. Li, J. Mol. Catal. A: Chem. 2006, 246, 18-23.
A. Corma, O. de la Torre, M. Renz, Energy Environ. Sci. 2012, 5, 6328-
[
[
8]
9]
6
344.
a) P. Wang, S. Bai, J. Zhao, P. Su, Q. Yang, C. Li, ChemSusChem
012, 5, 2390-2396; b) P. V. R. Rao, V. P. Kumar, G. S. Rao, K. V. R.
Chary, Catal. Sci. Tech. 2012, 2, 1665-1673.
Acknowledgements
2
This work was supported by the National Natural Science
Foundation of China (no. 21277140; 21476229; 21690082;
1690084, 21672210), Dalian Science Foundation for
Distinguished Young Scholars (no. 2015R005), the Strategic
Priority Research Program of the Chinese Academy of Sciences
XDB17020100), Department of Science and Technology of
[10] a) E. O'Reilly, C. Iglesias, D. Ghislieri, J. Hopwood, J. L. Galman, R. C.
Lloyd, N. J. Turner, Angew. Chem. Int. Ed. 2014, 53, 2447-2450; b) S.
Kotani, S. Aoki, M. Sugiura, M. Ogasawara, M. Nakajima, Org. Lett.
2
2014, 16, 4802-4805; c) T. A. Minard, C. T. Oswin, F. D. C. Waldie, J. K.
Howell, B. M. T. Scott, D. D. Mondo, R. J. Sullivan, B. Stein, M.
Jennings, M. Schlaf, J. Mol. Catal. A: Chem. 2016, 422, 175-187; d) P.
Li, J. Zhao, C. Xia, F. Li, Org. Lett. 2014, 16, 5992-5995.
(
Liaoning Province (under contract of 2015020086-101) and 100-
talent project of Dalian Institute of Chemical Physics (DICP).
[11] G. Li, N. Li, M. Zheng, S. Li, A. Wang, Y. Cong, X. Wang, T. Zhang,
Green Chem. 2016, 18, 3607-3613.
[
12] Y. L. Louie, J. Tang, A. M. L. Hell, A. T. Bell, Appl. Catal. B: Environ.
017, 202, 557-568.
Keywords: Aqueous phase hydrogenation • diketone • jet fuel •
lignocellulose • triketone
2
[
[
13] M. Haruta, M. Daté, Appl. Catal. A: Gen. 2001, 222, 427-437.
14] J. M. Poirier, G. Dujardin, Heterocycles 1987, 25, 399-407.
[
[
1]
2]
a) G. W. Huber, S. Iborra, A. Corma, Chem. Rev. 2006, 106, 4044-
[15] J. Mei, J. Mao, Z. Chen, S. Yuan, H. Li, H. Yin, Chem. Eng. Sci. 2015,
131, 213-218.
4098; b) D. M. Alonso, S. G. Wettstein, J. A. Dumesic, Chem. Soc. Rev.
2012, 41, 8075-8098; c) X. Wang, R. Rinaldi, Angew. Chem. Int. Ed.
2013, 52, 11499-11503; d) K. Barta, P. C. Ford, Acc. Chem. Res. 2014,
47, 1503-1512; e) M. Besson, P. Gallezot, C. Pinel, Chem. Rev. 2014,
114, 1827-1870.
[16] Y. Gong, L. Lin, B. X. Zhang, Chin. J. Chem. 2012, 30, 327-332.
[17] C. R. Waidmann, A. W. Pierpont, E. R. Batista, J. C. Gordon, R. L.
Martin, L. A. Silks, R. M. West, R. L. Wu, Catal. Sci. Tech. 2013, 3,
106-115.
a) G. W. Huber, J. N. Chheda, C. J. Barrett, J. A. Dumesic, Science
005, 308, 1446-1450; b) C. Zhao, Y. Kou, A. A. Lemonidou, X. B. Li, J.
[18] Z. Xu, P. Yan, W. Xu, X. Liu, Z. Xia, B. Chung, S. Jia, Z. C. Zhang, ACS
Catal. 2015, 5, 788-792.
2
A. Lercher, Angew. Chem. Int. Ed. 2009, 48, 3987-3990; c) J. Q. Bond,
D. M. Alonso, D. Wang, R. M. West, J. A. Dumesic, Science 2010, 327,
[19] J. He, C. Zhao, J. A. Lercher, J. Am. Chem. Soc. 2012, 134, 20768-
20775.
1
110-1114; d) N. Yan, Y. Yuan, R. Dykeman, Y. Kou, P. J. Dyson,
[20] a) G. Li, N. Li, X. Wang, X. Sheng, S. Li, A. Wang, Y. Cong, X. Wang, T.
Zhang, Energy Fuels 2014, 28, 5112-5118; b) X. Zhang, Q. Deng, P.
Han, J. Xu, L. Pan, L. Wang, J.-J. Zou, AIChE J. 2016, n/a-n/a; c) J.
Yang, S. Li, N. Li, W. Wang, A. Wang, T. Zhang, Y. Cong, X. Wang, G.
W. Huber, Ind. Eng. Chem. Res. 2015, 54, 11825-11837; d) Q. Deng, G.
Nie, L. Pan, J.-J. Zou, X. Zhang, L. Wang, Green Chem. 2015, 17,
4473-4481.
Angew. Chem. Int. Ed. 2010, 49, 5549-5553; e) B. G. Harvey, R. L.
Quintana, Energy Environ. Sci. 2010, 3, 352-357; f) A. Corma, O. de la
Torre, M. Renz, N. Villandier, Angew. Chem. Int. Ed. 2011, 50, 2375-
2378; g) A. D. Sutton, F. D. Waldie, R. L. Wu, M. Schlaf, L. A. Silks, J.
C. Gordon, Nature Chem. 2013, 5, 428-432; h) Q.-N. Xia, Q. Cuan, X.-
H. Liu, X.-Q. Gong, G.-Z. Lu, Y.-Q. Wang, Angew. Chem. Int. Ed. 2014,
5
3, 9755-9760; i) M. Mascal, S. Dutta, I. Gandarias, Angew. Chem. Int.
[21] J. Yang, N. Li, G. Li, W. Wang, A. Wang, X. Wang, Y. Cong, T. Zhang,
Chem. Commun. 2014, 50, 2572-2574.
Ed. 2014, 53, 1854-1857; j) S. Sankaranarayanapillai, S. Sreekumar, J.
Gomes, A. Grippo, G. E. Arab, M. Head-Gordon, F. D. Toste, A. T. Bell,
Angew. Chem. Int. Ed. 2015, 54, 4673-4677.
[22] a) X. Sheng, G. Li, W. Wang, Y. Cong, X. Wang, G. W. Huber, N. Li, A.
Wang, T. Zhang, AIChE J. 2016, 62, 2754-2761; b) X. Sheng, N. Li, G.
Li, W. Wang, A. Wang, Y. Cong, X. Wang, T. Zhang, Green Chem.
2016, 18, 3707-3711; c) S. S. Li, N. Li, W. T. Wang, L. Li, A. Q. Wang,
X. D. Wang, T. Zhang, Sci Rep 2016, 6, 7.
[
3]
a) A. Fukuoka, P. L. Dhepe, Angew. Chem. Int. Ed. 2006, 45, 5161-
5163; b) N. Ji, T. Zhang, M. Y. Zheng, A. Q. Wang, H. Wang, X. D.
Wang, J. G. G. Chen, Angew. Chem. Int. Ed. 2008, 47, 8510-8513; c) Y.
T. Cheng, J. Jae, J. Shi, W. Fan, G. W. Huber, Angew. Chem. Int. Ed.
[23] S. Ivanova, C. Petit, V. Pitchon, Appl. Catal. A: Gen. 2004, 267, 191-
201.
2012, 51, 1387-1390; d) Y. T. Cheng, Z. P. Wang, C. J. Gilbert, W. Fan,
G. W. Huber, Angew. Chem. Int. Ed. 2012, 51, 11097-11100; e) Y. L.
Wang, W. P. Deng, B. J. Wang, Q. H. Zhang, X. Y. Wan, Z. C. Tang, Y.
Wang, C. Zhu, Z. X. Cao, G. C. Wang, H. L. Wan, Nat. Commun. 2013,
4, 2141; f) F. Liu, M. Audemar, K. D. Vigier, D. Cartigny, J. M. Clacens,
M. F. C. Gomes, A. A. H. Padua, F. De Campo, F. Jerome, Green
Chem. 2013, 15, 3205-3213; g) F. Liu, M. Audemar, K. De Oliveira
Vigier, J.-M. Clacens, F. De Campo, F. Jerome, Green Chem. 2014, 16,
4110-4114; h) P. Sun, G. Gao, Z. Zhao, C. Xia, F. Li, ACS Catal. 2014,
4, 4136-4142; i) T. Prasomsri, M. Shetty, K. Murugappan, Y. Roman-
Leshkov, Energy Environ. Sci. 2014, 7, 2660-2669.
[
4]
R. W. Alder, N. P. Hyland, J. C. Jeffery, T. Riis-Johannessen, D. J.
Riley, Org. Biomol. Chem. 2009, 7, 2704-2715.
This article is protected by copyright. All rights reserved.