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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2658 - 2668

DOI: https://doi.org/10.6023/cjoc202003060

Research Progress of Homogeneous Catalyst for the Dehydrogenation of Formic Acid

  • Liu Jiahao ,
  • Han Jingjie ,
  • Yi Xiaoyi ,
  • Liu Chao ,
  • He Piao
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  • College of Chemistry and Chemical Engineering, Central South University, Changsha 410083

Received date: 2020-03-27

  Revised date: 2020-05-09

  Online published: 2020-06-13

Supported by

Project supported by the Research Start-Up Fund of Central South University (No. 201810).

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Abstract

Formic acid (HCOOH) has great potential as liquid hydrogen storage materials and for clean hydrogen production. In the past decade, researchers have not only made significant progress in developing more active, stable, and selective catalysts, but also proposed the concept of the reversible system of hydrogen release and storage. This review covers the latest progress of homogeneous catalysts in this field, focusing on the noble metal based catalysts represented by ruthenium, rhodium, and iridium, as well as the non-noble metal based catalysts such as iron, cobalt, nickel, copper, aluminum and so on. It is hoped that this review will provide some insights and idea for developing better catalytic systems for the dehydrogenation of formic acid in the future.

Key words： hydrogen energy; formic acid dehydrogenation; homogeneous catalysis; metal catalyst

Cite this article

Liu Jiahao , Han Jingjie , Yi Xiaoyi , Liu Chao , He Piao . Research Progress of Homogeneous Catalyst for the Dehydrogenation of Formic Acid[J]. Chinese Journal of Organic Chemistry, 2020 , 40(9) : 2658 -2668 . DOI: 10.6023/cjoc202003060

References

[1] Sordakis, K.; Tang, C.; Vogt, L. K.; Junge, H.; Dyson, P. J.; Beller, M.; Laurenczy, G. Chem. Rev. 2018, 118, 372.
[2] Coffey, R. S. Chem. Commun. 1967, 923.
[3] Gao, Y.; Kuncheria, J.; Puddephatt, R. J.; Yap, G. P. A. Chem. Commun. 1998, 2365.
[4] Gao, Y.; Kuncheria, J. K.; Jenkins, H. A.; Puddephatt, R. J.; Yap, G. P. A. J. Chem. Soc., Dalton Trans. 2000, 3212.
[5] Hannedouche, J. M.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986.
[6] Hayes, A. M.; Morris, D. J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2005, 127, 7318.
[7] Matharu, D. S.; Morris, D. J.; Clarkson, G. J.; Wills, M. Chem. Commun. 2006, 3232.
[8] Morris, D. J.; Clarkson, G. J.; Wills, M. Organometallics 2009, 28, 4133.
[9] Majewski, A.; Morris, D. J.; Kendall, K.; Wills, M. ChemSusChem 2010, 3, 431.
[10] Fellay, C.; Paul; nbsp; Dyson, J.; Laurenczy, G. Angew. Chem., Int. Ed. 2008, 120, 4030.
[11] Fellay, C.; Yan, N.; Dyson, P. J.; Laurenczy, G. Chem.-Eur. J. 2009, 15, 3752.
[12] Thevenon, A.; Frost-Pennington, E.; Weijia, G.; Dalebrook, A. F.; Laurenczy, G. ChemCatChem 2014, 6, 3146.
[13] Gan, W.; Fellay, C.; Dyson, P. J.; Laurenczy, G. J. Coord. Chem. 2010, 63, 2685.
[14] Gan, W.; Snelders, D. J. M.; Dyson, P. J.; Laurenczy, G. B. ChemCatChem 2013, 5, 1126.
[15] Loges, B.; Boddien, A.; Junge, H.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3962.
[16] Boddien, A.; Loges, B. R.; Junge, H.; Beller, M. ChemSusChem 2008, 1, 751.
[17] Boddien, A.; Loges, B.; Junge, H.; Gärtner, F.; Beller, M. Adv. Synth. Catal. 2009, 351, 2517.
[18] Boddien, A.; Loges, B.; Junge, H.; Noyes, J. R.; Beller, M. Tetrahedron Lett. 2009, 50, 1603.
[19] Loges, B.; Boddien, A.; Junge, H.; Noyes, J. R.; Baumann, W.; Beller, M. Chem. Commun. 2009, 4185.
[20] Boddien, A.; Federsel, C.; Sponholz, P.; Mellmann, D.; Jackstell, R.; Junge, H.; Laurenczy, G.; Beller, M. Energy Environ. Sci. 2012, 5, 8907.
[21] Sordakis, K.; Beller, M.; Laurenczy, G. ChemCatChem 2014, 6, 96.
[22] Sponholz, P.; Mellmann, D. r.; Junge, H.; Beller, M. ChemSusChem 2013, 6, 1172.
[23] Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114.
[24] Kawasaki, I.; Tsunoda, K.; Tsuji, T.; Yamaguchi, T.; Shibuta, H.; Uchida, N.; Yamashita, M.; Ohta, S. Chem. Commun. 2005, 2134.
[25] Li, X.; Ma, X.; Shi, F.; Deng, Y. ChemSusChem 2010, 3, 71.
[26] Scholten, J. D.; Prechtl, M. H. G.; Dupont, P. Â. J. ChemCatChem 2010, 2, 1265.
[27] Berger, M. E. M.; Assenbaum, D.; Taccardi, N.; Spiecker, E.; Wasserscheid, P. Green Chem. 2011, 13, 1411.
[28] Schuster, O.; Yang, L.; Raubenheimer, H. G.; Albrecht, M. Chem. Rev. 2009, 109, 3445.
[29] Czaun, M.; Goeppert, D. A.; May, R.; Haiges, D. R.; Prakash, P. D. G. K. S.; Olah, P. D. G. A. ChemSusChem 2011, 4, 1241.
[30] Czaun, M.; Goeppert, A.; Kothandaraman, J.; May, R. B.; Olah, G. A. ACS Catal. 2013, 4, 311.
[31] Kothandaraman, J.; Czaun, M.; Goeppert, A.; Haiges, R.; Jones, J.-P.; May, R. B.; Prakash, G. K. S.; Olah, G. A. ChemSusChem 2015, 8, 1442.
[32] Zell, T.; Butschke, B.; Ben-David, Y.; Milstein, D. Chem.-Eur. J. 2013, 19, 8068.
[33] Vogt, M.; Nerush, A.; Diskin-Posner, Y.; Ben-David, Y.; Milstein, D. Chem. Sci. 2014, 5, 2043.
[34] Filonenko, G. A.; van Putten, R.; Schulpen, E. N.; Hensen, E. J. M.; Pidko, E. A. ChemCatChem 2014, 6, 1526.
[35] Pan, Y.; Pan, C.-L.; Zhang, Y.; Li, H.; Min, S.; Guo, X.; Zheng, B.; Chen, H.; Anders, A.; Lai, Z.; Zheng, J.; Huang, K.-W. Chem. Asian J. 2016, 11, 1357.
[36] Fukuzumi, S.; Kobayashi, T.; Suenobu, T. J. Am. Chem. Soc. 2010, 132, 1496.
[37] Maenaka, Y.; Suenobu, T.; Fukuzumi, S. Energy Environ. Sci, 2012, 5, 7360.
[38] Himeda, Y. Green Chem. 2009, 11, 2018.
[39] Hull, J. F.; Himeda, Y.; Wang, W.-H.; Hashiguchi, B.; Periana, R.; Szalda, D. J.; Muckerman, J. T.; Fujita, E. Nat. Chem. 2012, 4, 383.
[40] Wang, W. H.; Xu, S.; Manaka, Y.; Suna, Y.; Kambayashi, H.; Muckerman, J. T.; Fujita, E.; Himeda, Y. ChemSusChem 2014, 7, 1976.
[41] Manaka, Y.; Wang, W. H.; Suna, Y.; Kambayashi, H.; Muckerman, J. T.; Fujita, E.; Himeda, Y. Catal. Sci. Technol. 2013, 4, 34.
[42] 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.
[43] Onishi, N.; Ertem, M. Z.; Xu, S.; Tsurusaki, A.; Manaka, Y.; Muckerman, J. T.; Fujita, E.; Himeda, Y. Catal. Sci. Technol. 2016, 6.
[44] Iguchi, M.; Himeda, Y.; Manaka, Y.; Kawanami, H. ChemSusChem 2016, 9, 2749.
[45] Guan, C.; Zhang, D.-D.; Pan, Y.; Iguchi, M.; Ajitha, M. J.; Hu, J.; Li, H.; Yao, C.; Huang, M.-H.; Min, S.; Zheng, J.; Himeda, Y.; Kawanami, H.; Huang, K.-W. Inorg. Chem. 2017, 56, 438.
[46] Iguchi, M.; Himeda, Y.; Manaka, Y.; Matsuoka, K.; Kawanami, H. ChemCatChem 2016, 8, 886.
[47] Barnard, J. H.; Wang, C.; Berry, N. G.; Xiao, J. Chem. Sci. 2013, 4, 1234.
[48] Tanaka, R.; Yamashita, M.; Chung, L. W.; Morokuma, K.; Nozaki, K. Organometallics 2011, 30, 6742.
[49] Fink, C.; Laurenczy, G. Dalton. Trans. 2017, 46, 1670.
[50] Onishi, N.; Kanega, R.; Fujita, E.; Himeda, Y. Adv. Synth. Catal. 2019, 361, 289.
[51] Lu, S.-M.; Wang, Z.; Wang, J.; Li, J.; Li, C. Green Chem. 2018, 20, 1835.
[52] Fukuzumi, S.; Kobayashi, T.; Suenobu, T. ChemSusChem 2008, 1, 827.
[53] Wang, Z.; Lu, S.-M.; Wu, J.; Li, C.; Xiao, J. Eur. J. Inorg. Chem. 2016, 2016, 490.
[54] Jongbloed, L.; Bruin, B. D.; Reek, J. N. H.; Lutz, M.; Vlugt, J. I. V. D. Catal. Sci. Technol. 2015, 6, 1320.
[55] Jantke, D.; Pardatscher, L.; Drees, M.; Cokoja, M.; Herrmann, W. A.; Kühn, F. E. ChemSusChem 2016, 9, 2849.
[56] Boddien, A.; Loges, B.; Gärtner, F.; Torborg, C.; Fumino, K.; Junge, H.; Ludwig, R.; Beller, M. J. Am. Chem. Soc. 2010, 132, 8924.
[57] Boddien, A.; Gärtner, F.; Jackstell, R.; Junge, H.; Spannenberg, A.; Baumann, W.; Ludwig, R.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 8993.
[58] Boddien, A.; Mellmann, D.; Gärtner, F.; Jackstell, R.; Junge, H.; Dyson, P. J.; Laurenczy, G.; Ludwig, R.; Beller, M. Science 2011, 333, 1733.
[59] Mellmann, D. R.; Barsch, E.; Bauer, M.; Grabow, K.; Boddien, A.; Kammer, A.; Sponholz, P.; Bentrup, U.; Jackstell, R.; Junge, H. Chem.-Eur. J. 2014, 20, 13589.
[60] Montandon-Clerc, M.; Dalebrook, A. F.; Laurenczy, G. J. Catal. 2016, 343, 62.
[61] Bielinski, E. A.; Lagaditis, P. O.; Zhang, Y.; Mercado, B. Q.; Würtele, C.; Bernskoetter, W. H.; Hazari, N.; Schneider, S. J. Am. Chem. Soc. 2014, 136, 10234.
[62] Bertini, F.; Mellone, I.; Ienco, A.; Peruzzini, M.; Gonsalvi, L. ACS Catal. 2015, 5, 1254.
[63] Mellone, I.; Gorgas, N.; Bertini, F.; Peruzzini, M.; Kirchner, K.; Gonsalvi, L. Organometallics 2016, 35, 3344.
[64] Myers, T. W.; Berben, L. A. Chem. Sci. 2014, 5, 2771.
[65] Enthaler, S.; Brück, A.; Kammer, A.; Junge, H.; Gülak, S. ChemCatChem 2014, 7, 65.
[66] Scotti, N.; Psaro, R.; Ravasio, N.; Zaccheria, F. RSC Adv. 2014, 4, 61514.
[67] Neary, M. C.; Parkin, G. Chem. Sci. 2015, 6, 1859.
[68] Neary, M. C.; Parkin, G. Dalton. Trans. 2016, 45, 14645.
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