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

  • 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.
  • 加载中
    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.

  • 加载中
    1. [1]

      Shiyi Chen , Jialong Fu , Jianping Qiu , Guoju Chang , Shiyou Hao . Waste medical mask-derived carbon quantum dots enhance the photocatalytic degradation of polyethylene terephthalate (PET) over BiOBr/g-C3N4 S-scheme heterojunction. Acta Physico-Chimica Sinica, 2026, 42(1): 100135-0. doi: 10.1016/j.actphy.2025.100135

    2. [2]

      Jiayi Yang ,  Jianxiu Hao ,  Huacong Zhou ,  Quansheng Liu . “Gorgeous Transformation” of Carbon Dioxide into Cyclic Carbonates: Catalyst Types and Roles. University Chemistry, 2026, 41(2): 178-189. doi: 10.12461/PKU.DXHX202502105

    3. [3]

      Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Liu Fei . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-0. doi: 10.3866/PKU.WHXB202408004

    4. [4]

      Yuanyuan Ping ,  Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092

    5. [5]

      Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398

    6. [6]

      Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO2 over Au/Co3O4-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005

    7. [7]

      Yuanjun LIU , Jiayang JIANG , Rui WANG , Jiangnan HU , Chaoyi YUAN , Xingmei GUO , Junhao ZHANG , Guoxing ZHU . Crystallinity and oxidation degree tuning of Ru for alkaline hydrogen oxidation. Chinese Journal of Inorganic Chemistry, 2026, 42(9): 1933-1944. doi: 10.11862/CJIC.20250373

    8. [8]

      Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201

    9. [9]

      Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO2 hydrogenation over a Mg-doped In2O3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421

    10. [10]

      Jilei LIANG , Mengmeng WU , Lü QI , Yunqi LIU , Chenguang LIU . In-situ preparation of mesoporous carbon-encapsulated NiMoS hydrodesulfurization catalyst. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2127-2137. doi: 10.11862/CJIC.20260127

    11. [11]

      Wenruo NI , Hongpeng LI , Yun ZHANG , Yiran TIAN , Jiehui RUI , Yingcheng TONG , Xiaolin PI , Zhenyan TANG . Research progress of ruthenium alloy catalysts in hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 23-44. doi: 10.11862/CJIC.20250188

    12. [12]

      Qinhui Guan , Yuhao Guo , Na Li , Jing Li , Tingjiang Yan . Molecular sieve-mediated indium oxide catalysts for enhancing photocatalytic CO2 hydrogenation. Acta Physico-Chimica Sinica, 2025, 41(11): 100133-0. doi: 10.1016/j.actphy.2025.100133

    13. [13]

      Xinhao Yan ,  Guoliang Hu ,  Ruixi Chen ,  Hongyu Liu ,  Qizhi Yao ,  Jiao Li ,  Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073

    14. [14]

      Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317

    15. [15]

      Feifei Yang , Wei Zhou , Chaoran Yang , Tianyu Zhang , Yanqiang Huang . Enhanced Methanol Selectivity in CO2 Hydrogenation by Decoration of K on MoS2 Catalyst. Acta Physico-Chimica Sinica, 2024, 40(7): 2308017-0. doi: 10.3866/PKU.WHXB202308017

    16. [16]

      Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-0. doi: 10.3866/PKU.WHXB202312024

    17. [17]

      Huiwei Ding , Bo Peng , Zhihao Wang , Qiaofeng Han . Advances in Metal or Nonmetal Modification of Bismuth-Based Photocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2305048-0. doi: 10.3866/PKU.WHXB202305048

    18. [18]

      Hailang JIA , Yujie LU , Pengcheng JI . Preparation and properties of nitrogen and phosphorus co-doped graphene carbon aerogel supported ruthenium electrocatalyst for hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2327-2336. doi: 10.11862/CJIC.20250021

    19. [19]

      Jiali Lei , Juan Wang , Wenhui Zhang , Guohong Wang , Zihui Liang , Jinmao Li . TiO2/CdIn2S4 S-scheme heterojunction photocatalyst promotes photocatalytic hydrogen evolution coupled vanillyl alcohol oxidation. Acta Physico-Chimica Sinica, 2025, 41(12): 100174-0. doi: 10.1016/j.actphy.2025.100174

    20. [20]

      Ying Chen ,  Ronghua Yan ,  Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066

Metrics
  • PDF Downloads(17)
  • Abstract views(2915)
  • HTML views(599)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return