Citation: Fang Xiaolong, Duan Ning, Zhang Min, Li Bin. Advances for Ruthenium Catalysts with Metal-Ligand Cooperation for Hydrogenation of Oxalates into Ethylene Glycol[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2692-2701. doi: 10.6023/cjoc202004017 shu

Advances for Ruthenium Catalysts with Metal-Ligand Cooperation for Hydrogenation of Oxalates into Ethylene Glycol

Fang Xiaolong ^a,b,, ,
Duan Ning ^a ,
Zhang Min ^a ,
Li Bin ^b,,

a.
Key Laboratory of Functional Molecule Design and Interface Process, College of Materials and Chemical Engineering, Anhui Jianzhu University, Hefei 230601
b.
State Key Laboratory of Physical Chemistry of Solid Surfaces, National Engineering Laboratory for Green Chemical Productions of Alcohols-Ethers-Esters, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005

Corresponding author: Fang Xiaolong, xlfang@stu.xmu.edu.cn Li Bin, binlee@stu.xmu.edu.cn
Received Date: 12 April 2020
Revised Date: 9 May 2020
Available Online: 27 May 2020
Fund Project: the Natural Science Foundation of Anhui Province 1808085QB48Project supported by the National Natural Science Foundation of China (No. 21802010) and the Natural Science Foundation of Anhui Province (No. 1808085QB48)the National Natural Science Foundation of China 21802010

Figures(8)

Ethylene glycol (EG) is an important fundamental chemical material, which has been widely used in the production of industrial chemicals such as polyester. Catalytic hydrogenation of oxalate into EG is a key step in the "coal-to-EG" industrial route. Design of efficient catalysts for catalyzing the hydrogenation of oxalate esters is a research hotspot. The research progress of ruthenium catalysts with metal-ligand cooperation in the homogeneous catalytic hydrogenation of oxalate esters in the past decade is reviewed. Based on the relationship between the catalyst structures and properties, the catalytic hydrogenation mechanism is discussed, which provides a reference for the further design and development of new catalysts with excellent performance.
- hydrogenation of oxalate,
- ethylene glycol,
- metal-ligand cooperation,
- ruthenium catalyst
1. [1]
  Chen, L.; Guo, P.; Qiao, M.; Yan, S.; Li, H.; Wei, S.; Xu, H.; Fan, K. J. Catal. 2008, 257, 172. doi: 10.1016/j.jcat.2008.04.021
2. [2]
  Yin, G. Sino-Global Energy 2012, 17, 62 (in Chinese).
3. [3]
4. [4]
  (a) Zheng, J.; Lin, H.; Wang, Y.; Zheng, X.; Duan, X.; Yuan, Y. J. Catal. 2013, 297, 110.
  (b) He, Z.; Lin, H.; He, P.; Yuan, Y. J. Catal. 2011, 277, 54.
  (c) Xu, C.; Chen, G.; Zhao, Y.; Liu, P.; Duan, X.; Gu, L.; Fu, G.; Yuan, Y.; Zheng, N. Nat. Commun. 2018, 9, 3367.
5. [5]
  Grey, R. A.; Pez, G. P.; Wallo, A. J. Am. Chem. Soc. 1981, 103, 7536. doi: 10.1021/ja00415a022
6. [6]
  (a) Turek, T.; Trimm, D. L.; Cant, N. W. Catal. Rev.: Sci. Eng. 1994, 36, 645.
  (b) Pouilloux, Y.; Autin, F.; Barrault, J. Catal. Today 2000, 63, 87.
  (c) Wang, H.; Zhang, T.; Zhou, X. J. Phys.: Condens. Matter 2019, 31, 473001.
7. [7]
  Grey, R. A.; Pez, G. P.; Wallo, A.; Corsi, J. J. Chem. Soc., Chem. Commun. 1980, 783.
8. [8]
  Matteoli, U.; Blanchi, M.; Menchi, G.; Prediani, P.; Piacenti, F. J. Mol. Catal. 1984, 22, 353. doi: 10.1016/0304-5102(84)80075-9
9. [9]
  (a) Matteoli, U.; Bianchi, M.; Menchi, G.; Frediani, P.; Piacenti, F. J. Mol. Catal. 1985, 29, 269.
  (b) Matteoli, U.; Menchi, G.; Bianchi, M.; Piacenti, F. J. Organomet. Chem. 1986, 299, 233.
10. [10]
  Teunissen, H. T.; J. Elsevier, C. Chem. Commun. 1997, 667.
11. [11]
  (a) Teunissen, H. T. Chem. Commun. 1998, 1367.
  (b) van Engelen, M. C.; Teunissen, H. T.; de Vries, J. G.; Elsevier, C. J. J. Mol. Catal. A: Chem. 2003, 206, 185.
12. [12]
  Boardman, B.; Hanton, M. J.; Rensburg, H. V.; Tooze, R. P. Chem. Commun. 2006, 2289.
13. [13]
  Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. doi: 10.1021/ja00146a041
14. [14]
  (a) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
  (b) Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104.
  (c) Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490.
  (d) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
  (e) Dub, P. A.; Gordon, J. C. Nat. Rev. Chem. 2018, 2, 396.
15. [15]
  (a) Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201.
  (b) vom Stein, T.; Meuresch, M.; Limper, D.; Schmitz, M.; Hölscher, M.; Coetzee, J.; Cole-Hamilton, D. J.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2014, 136, 13217.
  (c) Liu, Y.; Yue, X.; Luo, C.; Zhang, L.; Lei, M. Energy Environ. Mater. 2019, 2, 292.
16. [16]
  (a) Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718.
  (b) Zhao, B.; Han, Z.; Ding, K. Angew. Chem., Int. Ed. 2013, 52, 4744.
  (c) Werkmeister, S.; Junge, K.; Beller, M. Org. Process Res. Dev. 2014, 18, 289.
  (d) Pritchard, J.; Filonenko, G. A.; van Putten, R.; Hensen, E. J. M.; Pidko, E. A. Chem. Soc. Rev. 2015, 44, 3808.
  (e) Zhou, Y.; Khan, R.; Fan, B.; Xu, L. Synthesis 2019, 51, 2491.
  (f) Dub, P. A.; Batrice, R. J.; Gordon, J. C.; Scott, B. L.; Minko, Y.; Schmidt, J. G.; Williams, R. F. Org. Process Res. Dev. 2020, 24, 415.
17. [17]
  Saudan, L. A.; Saudan, C. M.; Debieux, C.; Wyss, P. Angew. Chem., Int. Ed. 2007, 46, 7473. doi: 10.1002/anie.200701015
18. [18]
  (a) Kuriyama, W.; Matsumoto, T.; Ogata, O.; Ino, Y.; Aoki, K.; Tanaka, S.; Ishida, K.; Kobayashi, T.; Sayo, N.; Saito, T. Org. Process Res. Dev. 2012, 16, 166.
  (b) Han, Z.; Rong, L.; Wu, J.; Zhang, L.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 13041.
19. [19]
  Ziebart, C.; Jackstell, R.; Beller, M. ChemCatChem 2013, 5.
20. [20]
  Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2012, 51, 2772. doi: 10.1002/anie.201108956
21. [21]
22. [22]
  (a) Abdur-Rashid, K.; Faatz, M.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2001, 123, 7473.
  (b) Hartmann, R.; Chen, P. Angew. Chem., Int. Ed. 2001, 40, 3581.
23. [23]
  Li, W.; Xie, J. H.; Yuan, M. L.; Zhou, Q. L. Green Chem. 2014, 16, 4081. doi: 10.1039/C4GC00835A
24. [24]
25. [25]
  Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40. doi: 10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO;2-5
26. [26]
  (a) Abdur-Rashid, K.; Guo, R.; Lough, A. J.; Morris, R. H.; Song, D. Adv. Synth. Catal. 2005, 347, 571.
  (b) Jia, W.; Chen, X.; Guo, R.; Sui-Seng, C.; Amoroso, D.; Lough, A. J.; Abdur-Rashid, K. Dalton Trans. 2009, 39, 8301.
27. [27]
  (a) Drake, J. L.; Manna, C. M.; Byers, J. A. Organometallics 2013, 32, 6891.
  (b) Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2013, 52, 2538.
  (c) Moore, C. M.; Bark, B.; Szymczak, N. K. ACS Catal. 2016, 6, 1981.
28. [28]
  John, J. M.; Takebayashi, S.; Dabral, N.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2013, 135, 8578. doi: 10.1021/ja401294q
29. [29]
  Dub, P. A.; Henson, N. J.; Martin, R. L.; Gordon, J. C. J. Am. Chem. Soc. 2014, 136, 3505. doi: 10.1021/ja411374j
30. [30]
  Ogata, O.; Nakayama, Y.; Nara, H.; Fujiwhara, M.; Kayaki, Y. Org. Lett. 2016, 18, 3894. doi: 10.1021/acs.orglett.6b01900
31. [31]
  (a) Ohkuma, T.; Koizumi, M.; Muñiz, K.; Hilt, G.; Kabuto, C.; Noyori, R. J. Am. Chem. Soc. 2002, 124, 6508.
  (b) Guo, R.; Chen, X.; Elpelt, C.; Song, D.; Morris, R. H. Org. Lett. 2005, 7, 1757.
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