Citation: Hailong Liu, Zhiwei Huang, Haixiao Kang, Chungu Xia, Jing Chen. Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2-and 1,5-pentanediol over highly dispersed Cu-Al₂O₃ catalysts[J]. Chinese Journal of Catalysis, ;2016, 37(5): 700-710. doi: 10.1016/S1872-2067(15)61080-4 shu

Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2-and 1,5-pentanediol over highly dispersed Cu-Al₂O₃ catalysts

1.
a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, Gansu, China;
2.
b University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Zhiwei Huang,
Received Date: 30 January 2016
Available Online: 7 March 2016
Fund Project: 国家自然科学基金(21133011,21203221,21473224) (21133011,21203221,21473224)甘肃省自然科学基金(1308RJZA281). (1308RJZA281)

Cu nanoparticles supported on a variety of oxide supports, including SiO₂, TiO₂, ZrO₂, Al₂O₃, MgO and ZnO, were investigated for the hydrogenolysis of biomass-derived furfuryl alcohol to 1,2-pentanediol and 1,5-pentanediol. A Cu-Al₂O₃ catalyst with 10 wt% Cu loading prepared by a co-precipitation method exhibited the best performance in terms of producing pentanediols compared with the other materials. This catalyst generated an 85.8% conversion and a 70.3% combined selectivity for the target pentanediols at 413 K and 8 MPa H₂ over an 8-h reaction. The catalyst could also be recycled over repeated reaction trials without any significant decrease in productivity. Characterizations with X-ray diffraction, NH₃/CO₂-temperature programmed desorption, N₂ adsorption, transmission electron microscopy and N₂O chemisorption demonstrated that intimate and effective interactions between Cu particles and the acidic Al₂O₃ support in this material greatly enhanced its activity and selectivity. The promotion of the hydrogenolysis reaction was found to be especially sensitive to the Cu particle size, and the catalyst with Cu particles 1.9 to 2.4 nm in size showed the highest turnover frequency during the synthesis of pentanediols.
- Furfuryl alcohol,
- 1,2-Pentanediol,
- 1,5-Pentanediol,
- Selective hydrogenolysis,
- Cu-Al catalyst
1. [1]
  [1] A. Corma, S. Iborra, A. Velty, Chem. Rev., 2007, 107, 2411-2502.
2. [2]
  [2] P. Gallezot, Chem. Soc. Rev., 2012, 41, 1538-1558.
3. [3]
  [3] C. Z. Li, X. C. Zhao, A. Q. Wang, G. W. Huber, T. Zhang, Chem. Rev., 2015, 115, 11559-11624.
4. [4]
  [4] R. Karinen, K. Vilonen, M. Niemelä, ChemSusChem, 2011, 4, 1002-1016.
5. [5]
  [5] I. Agirrezabal-Telleria, F. Hemmann, C. Jäger, P. L. Arias, E. Kemnitz, J. Catal., 2013, 305, 81-91.
6. [6]
  [6] K. Yan, G. S. Wu, T. Lafleur, C. Jarvis, Renew. Sust. Energ. Rev., 2014, 38, 663-676.
7. [7]
  [7] M. Besson, P. Gallezot, C. Pinel, Chem. Rev., 2014, 114, 1827-1870.
8. [8]
  [8] Y. Nakagawa, M. Tamura, K. Tomishige, ACS Catal., 2013, 3, 2655-2668.
9. [9]
  [9] M. Chia, Y. J. Pagán-Torres, D. Hibbitts, Q. H. Tan, H. N. Pham, A. K. Datye, M. Neurock, R. J. Davis, J. A. Dumesic, J. Am. Chem. Soc., 2011, 133, 12675-12689.
10. [10]
  [10] T. Mizugaki, T. Yamakawa, Y. Nagatsu, Z. Maeno, T. Mitsudome, K. Jitsukawa, K. Kaneda, ACS Sust. Chem. Eng., 2014, 2, 2243-2247.
11. [11]
  [11] S. Bhogeswararao, D. Srinivas, J. Catal., 2015, 327, 65-77.
12. [12]
  [12] S. S. Li, N. Li, G. Y. Li, L. Li, A. Q. Wang, Y. Cong, X. D. Wang, T. Zhang, Green Chem., 2015, 17, 3644-3652.
13. [13]
  [13] M. J. Climent, A. Corma, S. Iborra, Green Chem., 2014, 16, 516-547.
14. [14]
  [14] J. Lee, S. P. Burt, C. A. Carrero, A. C. Alba-Rubio, I. Ro, B. J. O'Neill, H. J. Kim, D. H. K. Jackson, T. F. Kuech, I. Hermans, J. A. Dumesic, G. W. Huber, J. Catal., 2015, 330, 19-27.
15. [15]
  [15] S. Koso, I. Furikado, A. Shimao, T. Miyazawa, K. Kunimori, K. Tomishige, Chem. Commun., 2009, 2035-2037.
16. [16]
  [16] W. J. Xu, H. F. Wang, X. H. Liu, J. W. Ren, Y. Q. Wang, G. Z. Lu, Chem. Commun., 2011, 47, 3924-3926.
17. [17]
  [17] B. Zhang, Y. L. Zhu, G. Q. Ding, H. Y. Zheng, Y. W. Li, Green Chem., 2012, 14, 3402-3409.
18. [18]
  [18] B. Pholjaroen, N. Li, Y. Huang, L. Li, A. Wang, T. Zhang, Catal. Today, 2015, 245, 93-99.
19. [19]
  [19] S. B. Liu, Y. Amada, M. Tamura, Y. Nakagawa, K. Tomishige, Green Chem., 2014, 16, 617-626.
20. [20]
  [20] S. B. Liu, Y. Amada, M. Tamura, Y. Nakagawa, K. Tomishige, Catal. Sci. Technol., 2014, 4, 2535-2549.
21. [21]
  [21] S. Koso, N. Ueda, Y. Shinmi, K. Okumura, T. Kizuka, K. Tomishige, J. Catal., 2009, 267, 89-92.
22. [22]
  [22] O. Koch, A. Köckritz, M. Kant, A. Martin, A. Schöning, U. Armbruster, M. Bartoszek, S. Evert, B. Lange, R. Bienert, US Patent 20 140 066 666, 2012.
23. [23]
  [23] K. Y. Chen, S. Koso, T. Kubota, Y. Nakagawa, K. Tomishige, ChemCatChem, 2010, 2, 547-555.
24. [24]
  [24] K. Y. Chen, K. Mori, H. Watanabe, Y. Nakagawa, K. Tomishige, J. Catal., 2012, 294, 171-183.
25. [25]
  [25] H. Adkins, R. Connor, J. Am. Chem. Soc., 1931, 53, 1091-1095.
26. [26]
  [26] Z. W. Huang, J. Chen, Y. Q. Jia, H. L. Liu, C. G. Xia, H. C. Liu, Appl. Catal. B, 2014, 147, 377-386.
27. [27]
  [27] H. L. Liu, Z. W. Huang, C. G. Xia, Y. Q. Jia, J. Chen, H. C. Liu, ChemCatChem, 2014, 6, 2918-2928.
28. [28]
  [28] Z. W. Huang, F. Cui, H. X. Kang, J. Chen, X. Z. Zhang, C. G. Xia, Chem. Mater., 2008, 20, 5090-5099.
29. [29]
  [29] H. L. Liu, Z. W. Huang, Z. B. Han, K. L. Ding, H. C. Liu, C. G. Xia, J. Chen, Green Chem., 2015, 17, 4281-4290.
30. [30]
  [30] H. L. Liu, Z. W. Huang, F. Zhao, F. Cui, X. M. Li, C. G. Xia, J. Chen, Catal. Sci. Technol., 2016, 6, 668-671.
31. [31]
  [31] J. Tuteja, H. Choudhary, S. Nishimura, K. Ebitani, ChemSusChem, 2014, 7, 96-100.
32. [32]
  [32] C. J. G. Van Der Grift, A. F. H. Wielers, B. P. J. Jogh, J. Van Beunum, M. De Boer, M. Versluijs-Helder, J. W. Geus, J. Catal., 1991, 131, 178-189.
33. [33]
  [33] Y. F. Zhu, X. Kong, X. Q. Li, G. Q. Ding, Y. L. Zhu, Y. W. Li, ACS Catal., 2014, 4, 3612-3620.
34. [34]
  [34] X. H. He, H. C. Liu, Catal. Today, 2014, 233, 133-139.
35. [35]
  [35] R. A. Van Santen, Acc. Chem. Res., 2009, 42, 57-66.
36. [36]
  [36] S. Wang, K. H. Yin, Y. C. Zhang, H. C. Liu, ACS Catal., 2013, 3, 2112-2121.
37. [37]
  [37] S. Sitthisa, T. Sooknoi, Y. G. Ma, P. B. Balbuena, D. E. Resasco, J. Catal., 2011, 277, 1-13.
38. [38]
  [38] R. S. Rao, A. B. Walters, M. A. Vannice, J. Phys. Chem. B, 2005, 109, 2086-2092.
39. [39]
  [39] Y. F. Zhu, X. Kong, X. Q. Li, G. Q. Ding, Y. L. Zhu, Y. W. Li, ACS Catal., 2014, 4, 3612-3620.
40. [40]
  [40] M. A. Mellmer, J. M. R. Gallo, D. M. Alonso, J. A. Dumesic, ACS Catal., 2015, 5, 3354-3359.
41. [41]
  [41] J. Yang, H. Y. Zheng, Y. L. Zhu, G. W. Zhao, C. H. Zhang, B. T. Teng, H. W. Xiang, Y. W. Li, Catal. Commun., 2004, 5, 505-510.
42. [42]
  [42] J. Lessard, J. F. Morin, J. F. Wehrung, D. Magnin, E. Chornet, Top. Catal., 2010, 53, 1231-1234.
43. [43]
  [43] S. Sitthisa, W. An, D.E. Resasco, J. Catal., 2011, 284, 90-101.
44. [44]
  [44] S. G. Wang, V. Vorotnikov, D. G. Vlachos, Green Chem., 2014, 16, 736-747.
45. [45]
  [45] M. J. Gilkey, P. Panagiotopoulou, A. V. Mironenko, G. R. Jenness, D. G. Vlachos, B. J. Xu, ACS Catal., 2015, 5, 3988-3994.
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2-and 1,5-pentanediol over highly dispersed Cu-Al2O3 catalysts

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通讯作者: 陈斌, bchen63@163.com

Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2-and 1,5-pentanediol over highly dispersed Cu-Al₂O₃ catalysts