Citation: Xu Zhanwei, Yan Peifang, Zhang Zongconrad. Advance in the Hydrogenation of 5-Hydroxymethylfurfural to Produce 1-Hydroxyhexane-2, 5-dione[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 40-46. doi: 10.6023/cjoc201607026 shu

Advance in the Hydrogenation of 5-Hydroxymethylfurfural to Produce 1-Hydroxyhexane-2, 5-dione

Dalian National Laboratory for Clean Energy, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023

Corresponding author: Zhang Zongconrad, zczhang@yahoo.com
Received Date: 18 July 2016
Revised Date: 22 August 2016

Fund Project: the China Postdoctoral Science Foundation 2013M540236

Figures(12)

Recently, catalytic transformation of biobased 5-hydroxymethylfurfural (5-HMF) has been paid much more attentions.1-Hydroxyhexane-2, 5-dione (HHD) is a potential feedstock to synthesize valuable chemicals.The recent remarkable progress of HHD preparation, which utilized 5-HMF as a starting material, is a green and atom economic method.In this review, the approaches of HHD preparation from 5-HMF are summarized based on the homogeneous and heterogeneous catalysis.
- biomass,
- furan,
- hydrogenation,
- ketones
1. [1]
  Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411. doi: 10.1021/cr050989d
2. [2]
  Lynd, L. R.; Wyman, C. E.; Gerngross, T. U. Biotechnol. Prog. 1999, 15, 777. doi: 10.1021/bp990109e
3. [3]
  Román-Leshkov, Y.; Chheda, J. N.; Dumesic, J. A. Science 2006, 312, 1933. doi: 10.1126/science.1126337
4. [4]
  Zhao, H.; Holladay, J. E.; Brown, H.; Zhang, Z. C. Science 2007, 316, 1597. doi: 10.1126/science.1141199
5. [5]
  Teong, S. P.; Yi, G.; Zhang, Y. Green Chem. 2014, 16, 2015. doi: 10.1039/c3gc42018c
6. [6]
  Wang, J.; Zhang, C.-P.; Ouyang, P.-K. Chem. Ind. Eng. Prog. 2008, 27, 702 (in Chinese).
7. [7]
  Sheldon, R. A. Green Chem. 2014, 16, 950. doi: 10.1039/C3GC41935E
8. [8]
  van Putten, R.-J.; van der Waal, J. C.; de Jong, E.; Rasrendra, C. B.; Heeres, H. J.; de Vries, J. G. Chem. Rev. 2013, 113, 1499. doi: 10.1021/cr300182k
9. [9]
  Zakrzewska, M. E.; Bogel-Łukasik, E.; Bogel-Łukasik, R. Chem.Rev. 2011, 111, 397. doi: 10.1021/cr100171a
10. [10]
  Bozell, J. J.; Petersen, G. R. Green Chem. 2010, 12, 539. doi: 10.1039/b922014c
11. [11]
  Nakagawa, Y.; Tamura, M.; Tomishige, K. ACS Catal. 2013, 3, 2655. doi: 10.1021/cs400616p
12. [12]
  Zhu, S.; Wang, J.; Fan, W. Catal. Sci. Technol. 2015, 5, 3845. doi: 10.1039/C5CY00339C
13. [13]
  Xu, Z.; Yan, P.; Liu, K.; Wan, L.; Xu, W.; Li, H.; Liu, X.; Zhang, Z. C. ChemSusChem 2016, 9, 1255. doi: 10.1002/cssc.201600122
14. [14]
  O'Reilly, E.; Iglesias, C.; Ghislieri, D.; Hopwood, J.; Galman, J. L.; Lloyd, R. C.; Turner, N. J. Angew. Chem., Int. Ed. 2014, 53, 2447. doi: 10.1002/anie.201309208
15. [15]
  Kotani, S.; Aoki, S.; Sugiura, M.; Ogasawara, M.; Nakajima, M. Org. Lett. 2014, 16, 4802. doi: 10.1021/ol502269w
16. [16]
  Sharma, G. V. M.; Srikanth, G.; Reddy, P. P. Org. Biomol. Chem. 2012, 10, 8119. doi: 10.1039/c2ob26396c
17. [17]
  Chen, J.; Lu, F.; Zhang, J.; Yu, W.; Wang, F.; Gao, J.; Xu, J. ChemCatChem 2013, 5, 2822. doi: 10.1002/cctc.v5.10
18. [18]
  Yang, Y.; Du, Z.; Ma, J.; Lu, F.; Zhang, J.; Xu, J. Chem Sus Chem 2014, 7, 1352. doi: 10.1002/cssc.201301270
19. [19]
  Shono, T.; Matsumura, Y.; Hamaguchi, H. J. Chem. Soc., Chem.Commun. 1977, 712.
20. [20]
  Chatterjee, M.; Ishizaka, T.; Kawanami, H. Green Chem. 2014, 16, 1543. doi: 10.1039/c3gc42145g
21. [21]
  Schiavo, V.; Descotes, G.; Mentech, J. Bull. Soc. Chim. Fr. 1991, 704.
22. [22]
  Rout, P. K.; Nannaware, A. D.; Prakash, O.; Kalra, A.; Raja-sekharan, R. Chem. Eng. Sci. 2016, 142, 318. doi: 10.1016/j.ces.2015.12.002
23. [23]
  Putro, J. N.; Soetaredjo, F. E.; Lin, S.-Y.; Ju, Y.-H.; Ismadji, S. RSC Adv. 2016, 6, 46834. doi: 10.1039/C6RA09851G
24. [24]
  Buntara, T.; Noel, S.; Phua, P. H.; Meliá-Cabrera, I.; de Vries, J. G.; Heeres, H. J. Angew. Chem., Int. Ed. 2011, 50, 7083. doi: 10.1002/anie.v50.31
25. [25]
  Liu, F.; Audemar, M.; De Oliveira Vigier, K.; Clacens, J.-M.; De Campo, F.; Jér me, F. ChemSusChem 2014, 7, 2089. doi: 10.1002/cssc.201402221
26. [26]
  Liu, F.; Audemar, M.; De Oliveira Vigier, K.; Clacens, J.-M.; De Campo, F.; Jér me, F. Green Chem. 2014, 16, 4110. doi: 10.1039/C4GC01158A
27. [27]
  Ohyama, J.; Kanao, R.; Esaki, A.; Satsuma, A. Chem. Commun. 2014, 50, 5633. doi: 10.1039/c3cc49591d
28. [28]
  Xu, Z.; Yan, P.; Xu, W.; Liu, X.; Xia, Z.; Chung, B.; Jia, S.; Zhang, Z. C. ACS Catal. 2015, 5, 788. doi: 10.1021/cs501874v
29. [29]
  Fujita, K.; Tanaka, Y.; Kobayashi, M.; Yamaguchi, R. J. Am.Chem. Soc. 2014, 136, 4829. doi: 10.1021/ja5001888
30. [30]
  Zeng, G.; Sakaki, S.; Fujita, K.; Sano, H.; Yamaguchi, R. ACS Catal. 2014, 4, 1010. doi: 10.1021/cs401101m
31. [31]
  Fujita, K.; Kawahara, R.; Aikawa, T.; Yamaguchi, R. Angew.Chem., Int. Ed. 2015, 54, 9057. doi: 10.1002/anie.201502194
32. [32]
  Wang, W.-H.; Himeda, Y.; Muckerman, J. T.; Manbeck, G. F.; Fu-jita, E. Chem. Rev. 2015, 115, 12936. doi: 10.1021/acs.chemrev.5b00197
33. [33]
  Wang, W.-H.; Ertem, M. Z.; Xu, S.; Onishi, N.; Manaka, Y.; Suna, Y.; Kambayashi, H.; Muckerman, J. T.; Fujita, E.; Himeda, Y.ACS Catal. 2015, 5, 5496. doi: 10.1021/acscatal.5b01090
34. [34]
  Onishi, N.; Xu, S.; Manaka, Y.; Suna, Y.; Wang, W.-H.; Mucker-man, J. T.; Fujita, E.; Himeda, Y. Inorg. Chem. 2015, 54, 5114. doi: 10.1021/ic502904q
35. [35]
  Wang, R.; Ma, J.; Li, F. J. Org. Chem. 2015, 80, 10769. doi: 10.1021/acs.joc.5b01975
36. [36]
  Ou, W. C.; Cundari, T. R. ACS Catal. 2015, 5, 225. doi: 10.1021/cs501222m
37. [37]
  Xu, Z.; Yan, P.; Li, H.; Liu, K.; Liu, X.; Jia, S.; Zhang, Z. C. ACS Catal. 2016, 6, 3784. doi: 10.1021/acscatal.6b00826
38. [38]
  Wu, W.-P.; Xu, Y.-J.; Zhu, R.; Cui, M.-S.; Li, X.-L.; Deng, J.; Fu, Y. Chem Sus Chem 2016, 9, 1209. doi: 10.1002/cssc.v9.10
39. [39]
  Gupta, K.; Tyagi, D.; Dwivedi, A. D.; Mobin, S. M.; Singh, S. K. Green Chem. 2015, 17, 4618. doi: 10.1039/C5GC01376C
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