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

  • Fang Xiaolong ,
  • Duan Ning ,
  • Zhang Min ,
  • Li Bin
Expand
  • 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

Received date: 2020-04-12

  Revised date: 2020-05-09

  Online published: 2020-05-29

Supported by

Project supported by the National Natural Science Foundation of China (No. 21802010) and the Natural Science Foundation of Anhui Province (No. 1808085QB48).

Abstract

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.

Cite this article

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

References

[1] Chen, L.; Guo, P.; Qiao, M.; Yan, S.; Li, H.; Wei, S.; Xu, H.; Fan, K. J. Catal. 2008, 257, 172.
[2] Yin, G. Sino-Global Energy 2012, 17, 62(in Chinese). (尹国海, 中外能源, 2012, 17, 62.)
[3] (a) Liu, Z. Chem. Ind. Eng. Prog. 2013, 32, 1214(in Chinese). (刘宗语, 化工进展, 2013, 32, 1214.)
(b) Chen, W.; Sun, J.; Zhang, J.; Zhang, S.; Hua, W. Chem. Ind. Eng. Prog. 2014, 33, 1740(in Chinese). (成卫国, 孙剑, 张军平, 张锁江, 华炜, 化工进展, 2014, 33, 1740.)
[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] Grey, R. A.; Pez, G. P.; Wallo, A. J. Am. Chem. Soc. 1981, 103, 7536.
[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] Grey, R. A.; Pez, G. P.; Wallo, A.; Corsi, J. J. Chem. Soc., Chem. Commun. 1980, 783.
[8] Matteoli, U.; Blanchi, M.; Menchi, G.; Prediani, P.; Piacenti, F. J. Mol. Catal. 1984, 22, 353.
[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] Teunissen, H. T.; J. Elsevier, C. Chem. Commun. 1997, 667.
[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] Boardman, B.; Hanton, M. J.; Rensburg, H. V.; Tooze, R. P. Chem. Commun. 2006, 2289.
[13] Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.
[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] (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] (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] Saudan, L. A.; Saudan, C. M.; Debieux, C.; Wyss, P. Angew. Chem., Int. Ed. 2007, 46, 7473.
[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] Ziebart, C.; Jackstell, R.; Beller, M. ChemCatChem 2013, 5.
[20] Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2012, 51, 2772.
[21] (a) Van der Sluys, L. S.; Kubas, G. J.; Caulton, K. G. Organometallics 1991, 10, 1033.
(b) Chen, Y. Z.; Chan, W. C.; Lau, C. P.; Chu, H. S.; Lee, H. L.; Jia, G. Organometallics 1997, 16, 1241.
(c) Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2006, 128, 13700.
(d) Shen, Y.; Zhan, Y.; Li, S.; Ning, F.; Du, Y.; Huang, Y.; He, T.; Zhou, X. ChemSusChem 2018, 11, 864.
(e) Fang, X.; Duan, N.; Zhang, M.; Zhang, C.; Liu, R.; Zhu, H. P. Chin. J. Org. Chem. 2019, 39, 1450(in Chinese). (方霄龙, 段宁, 章敏, 张春燕, 刘睿, 朱红平, 有机化学, 2019, 39, 1450.)
[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] Li, W.; Xie, J. H.; Yuan, M. L.; Zhou, Q. L. Green Chem. 2014, 16, 4081.
[24] (a) Fang, X.; Zhang, C.; Chen, J.; Zhu, H.; Yuan, Y. RSC Adv. 2016, 6, 45512.
(b) Zhang, Y. W.; Chen, Y. L.; Fang, X. L.; Yuan, Y. Z.; Zhu, H. P. Chin. J. Org. Chem. 2017, 37, 2275(in Chinese). (张亦伟, 陈艺林, 方霄龙, 袁友珠, 朱红平, 有机化学, 2017, 37, 2275.)
(c) Fang, X.; Sun, M.; Zheng, J.; Li, B.; Ye, L.; Wang, X.; Cao, Z.; Zhu, H.; Yuan, Y. Sci. Rep. 2017, 7, 3961.
(d) Fang, X.; Li, B.; Zheng, J.; Wang, X.; Zhu, H.; Yuan, Y. Dalton Trans. 2019, 48, 2290.
(e) Fang, X.; Zhang, M.; Duan, N.; Wang, X.; Zhu, H. P. Chin. J. Org. Chem. 2020, 40, 226(in Chinese). (方霄龙, 章敏, 段宁, 汪新, 朱红平, 有机化学, 2020, 40, 226.)
[25] Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
[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] (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] John, J. M.; Takebayashi, S.; Dabral, N.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2013, 135, 8578.
[29] Dub, P. A.; Henson, N. J.; Martin, R. L.; Gordon, J. C. J. Am. Chem. Soc. 2014, 136, 3505.
[30] Ogata, O.; Nakayama, Y.; Nara, H.; Fujiwhara, M.; Kayaki, Y. Org. Lett. 2016, 18, 3894.
[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.
Outlines

/

〈 〉