Recent Developments of Homogeneous Transition-Metal Catalysts for Low Temperature Dehydrogenation of Methanol

doi:10.6023/cjoc201902032

Abstract

It is extremely urgent to develop green energy and find alternatives to fossil fuels since the energy shortage and environmental pollution become the worldwide concern. Methanol has emerged as a promising carrier for hydrogen storage owing to its high hydrogen density, simple structure and environmental friendly substance. The methanol reforming has triggered great efforts on the development of homogeneous catalysts, and the aim is to decrease methanol dehydrogenation reaction temperature and improve the selectivity. This review summarizes the recent research progresses in the homogeneously transition-metal catalyzed thermal dehydrogenation of methanol and aqueous methanol reforming. It mainly focuses on the structural characteristics of Ru, Rh, Ir, Fe and Mn-based complexes, catalytic reaction conditions, the reaction yield, and the catalytic reaction mechanism. The differences in the reactivities of these catalysts are analyzed and compared. Not only a summary is given, but also some perspectives and inspiration for improving the performance of aqueous methanol reforming catalysts for future research are discussed.

Key words: methanol, C-H activation, dehydrogenation, homogeneous catalyst, Ru

Cite this article

Zhang Xiang, Guo Caihong, Wu Haishun. Recent Developments of Homogeneous Transition-Metal Catalysts for Low Temperature Dehydrogenation of Methanol[J]. Chin. J. Org. Chem., 2019, 39(9): 2458-2466.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Armaroli, N.; Balzani, V. Chem. Asian J. 2011, 6, 768.
[2] Behrendt, F.; Schüth, F. Chem. Ing. Tech. 2011, 83, 1984.
[3] Cook, T. R.; Dogutan, D. K.; Reece, S. Y.; Surendranath, Y.; Teets, T. S.; Nocera, D. G. Chem. Rev. 2010, 110, 6474.
[4] Armaroli, N.; Balzani, V. ChemSusChem 2011, 4, 21.
[5] Zheng, J. Y.; Liu, X. X.; Xu, P.; Liu, P. F.; Zhao, Y. Z.; Yang, J. Int. J. Hydrogen Energy 2012, 37, 1048.
[6] Xu, Y.; Tao, Z.-L.; Chen, J. Prog. Chem. 2006, 18, 200(in Chinese). (许炜, 陶占良, 陈军, 化学进展, 2006, 18, 200.)
[7] Dalebrook, A. F.; Gan, W.; Grasemann, M.; Moret, S.; Laurenczy, G. Chem. Commun. 2013, 49, 8735.
[8] Chen, J.; Chen, Q.-X.; Chen, Y.-W.; Fan, S.-S.; Wang, Y.-H.; Yang, L.; Lang, X.-M.; Zhang, W.-X.; Huang, Y.; Xiong, W.-T. Energy Storage Sci. Tech. 2015, 4, 131(in Chinese). (陈俊, 陈秋雄, 陈运文, 樊栓狮, 王燕鸿, 杨亮, 郎雪梅, 张雯翔, 黄怡, 熊文涛, 储能科学与技术, 2015, 4, 131.)
[9] Chen, Z.; Yang, Y.-Q.; Bao, J.-G.; Wang, W.-Y.; Jiang, X.-M., Chem. Ind. Eng. Prog. 2010, 29, 484(in Chinese). (陈卓, 杨运泉, 包建国, 王威燕; 蒋新民, 化工进展, 2010, 29, 484.)
[10] Li, L.-L.; Fan, S.-S.; Chen, Q.-X.; Yang, G.; Wen, Y.-G. Energy Storage Sci. Tech. 2018, 7, 586(in Chinese). (李璐伶; 樊栓狮; 陈秋雄; 杨光; 温永刚, 储能科学与技术, 2018, 7, 586.)
[11] Niaz, S.; Manzoor, T.; Pandith, A. H. Renew. Sust. Energ. Rev. 2015, 50, 457.
[12] Ares, J. R. Int. J. Hydrogen Energy 2014, 39, 9824.
[13] Sordakis, K.; Tang, C.; Vogt, L. K.; Junge, H.; Dyson, P. J.; Beller, M.; Laurenczy, G. Chem. Rev. 2018, 118, 372.
[14] Alberico, E.; Nielsen, M. Chem. Commun. (Camb.) 2015, 51, 6714.
[15] He, T.; Pachfule, P.; Wu, H.; Xu, Q.; Chen, P. Nat. Rev. Mater. 2016, 1, 16059.
[16] Li, H.-W.; Yan, Y.; Orimo, S.-I.; Züttel, A.; Jensen, C. M. Energies 2011, 4, 185.
[17] Peng, B.; Chen, J. Energ. Environ. Sci. 2008, 1, 479.
[18] Zhu, Q.-L.; Xu, Q. Energ. Environ. Sci. 2015, 8, 478.
[19] Klerke, A.; Christensen, C. H.; Nørskov, J. K.; Vegge, T. J. Mater. Chem. 2008, 18, 2304.
[20] Moury, R.; Moussa, G.; Demirci, U. B.; Hannauer, J.; Bernard, S.; Petit, E.; van der Lee, A.; Miele, P. Phys. Chem. Chem. Phys. 2012, 14, 1768.
[21] Zhao, H. Y.; Oyama, S. T.; Naeemi, E. D. Catal. Today 2010, 149, 172.
[22] (a) Grasemann, M.; Laurenczy, G. Energ. Environ. Sci. 2012, 5, 8171.
(b) Mellmann, D.; Sponholz, P.; Junge, H.; Beller, M. Chem. Soc. Rev. 2016, 45, 3954.
[23] Johnson, T. C.; Morris, D. J.; Wills, M. Chem. Soc. Rev. 2010, 39, 81.
[24] Asinger, F. Methanol——Chemie und Energierohstoff, Springer, Berlin, Heidelberg, 1986, pp. 1~9.
[25] Smith, T. A.; Maitlis, P. M. J. Organomet. Chem. 1984, 269, c7.
[26] Wang, W.-H.; Himeda, Y.; Muckerman, J. T.; Manbeck, G. F.; Fujita, E. Chem. Rev. 2015, 115, 12936.
[27] Sá, S.; Silva, H.; Brandão, L.; Sousa, J. M.; Mendes, A. Appl. Catal. B-Environ. 2010, 99, 43.
[28] Iulianelli, A.; Ribeirinha, P.; Mendes, A.; Basile, A. Renew. Sust. Energ. Rev. 2014, 29, 355.
[29] Cortright, R. D.; Davda, R. R.; Dumesic, J. A. Nature 2002, 418, 964.
[30] Lin, L.; Zhou, W.; Gao, R.; Yao, S.; Zhang, X.; Xu, W.; Zheng, S.; Jiang, Z.; Yu, Q.; Li, Y.-W.; Shi, C.; Wen, X.-D.; Ma, D. Nature 2017, 544, 80.
[31] Palo, D. R.; Dagle, R. A.; Holladay, J. D. Chem. Rev. 2007, 107, 3992.
[32] Navarro, R. M.; Peña, M. A.; Fierro, J. L. G. Chem. Rev. 2007, 107, 3952.
[33] Wu, S.; Xiong.X.-D.; Wang, S.-G. Rare Metals 2007, 31, 237(in Chinese). (吴松; 熊晓东; 王胜国, 稀有金属, 2007, 31, 237.)
[34] Smith, T. A.; Aplin, R. P.; Maitlis, P. M. J. Organomet. Chem. 1985, 291, c13.
[35] Shinoda, S.; Itagaki, H.; Saito, Y. J. Chem. Soc., Chem. Commun. 1985, 13, 860.
[36] Itagaki, H.; Shinoda, S.; Saito, Y., Bull. Chem. Soc. Jpn. 1988, 61, 2291.
[37] Morton, D.; Cole-Hamilton, D. J. J. Chem. Soc. Chem. Commun., 1988, 1154.
[38] Fujii, T.; Saito, Y. J. Mol. Catal. 1991, 67, 185.
[39] Sieffert, N.; Bühl, M. J. Am. Chem. Soc. 2010, 132, 8056.
[40] Rodríguezlugo, R. E.; Trincado, M.; Vogt, M.; Tewes, F.; Santisoquinones, G.; Grützmacher, H. Nat. Chem. 2013, 5, 342.
[41] Nielsen, M.; Alberico, E.; Baumann, W.; Drexler, H.-J.; Junge, H.; Gladiali, S.; Beller, M. Nature 2013, 495, 85.
[42] Li, H.; Hall, M. B. J. Am. Chem. Soc. 2015, 137, 12330.
[43] Jing, Y.; Chen, X.; Yang, X. J. Organomet. Chem. 2016, 820, 55.
[44] Sinha, V.; Trincado, M.; Grützmacher, H.; de Bruin, B., J. Am. Chem. Soc. 2018, 140, 13103.
[45] 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.
[46] (a) Bertoli, M.; Choualeb, A.; Lough, A. J.; Moore, B.; Spasyuk, D.; Gusev, D. G. Organometallics 2011, 30, 3479.
(b) Nielsen, M.; Kammer, A.; Cozzula, D.; Junge, H.; Gladiali, S.; Beller, M. Angew. Chem., Int. Ed. Engl. 2011, 50, 9593.
[47] Lei, M.; Pan, Y.; Ma, X. Eur. J. Inorg. Chem. 2015, 2015, 794.
[48] Alberico, E.; Lennox, A. J.; Vogt, L. K.; Jiao, H.; Baumann, W.; Drexler, H. J.; Nielsen, M.; Spannenberg, A.; Checinski, M. P.; Junge, H.; Beller, M. J. Am. Chem. Soc. 2016, 138, 14890.
[49] Yang, X. ACS Catal. 2014, 4, 1129.
[50] Monney, A.; Barsch, E.; Sponholz, P.; Junge, H.; Ludwig, R.; Beller, M. Chem. Commun. 2014, 50, 707.
[51] Hu, P.; Diskin-Posner, Y.; Ben-David, Y.; Milstein, D. ACS Catal. 2014, 4, 2649.
[52] Heim, L. E.; Schlörer, N. E.; Choi, J. H.; Prechtl, M. H. Nat. Commun. 2014, 5, 3621.
[53] Crabtree, R. H. New J. Chem. 2011, 35, 18.
[54] (a) Crabtree, R. H. Chem. Rev. 2017, 117, 9228.
(b) Grützmacher, H., Angew. Chem., Int. Ed. 2008, 47, 1814.
[55] Kothandaraman, J.; Kar, S.; Goeppert, A.; Sen, R.; Prakash, G. K. S. Top. Catal. 2018, 61, 542.
[56] Heim, L. E.; Thiel, D.; Gedig, C.; Deska, J.; Prechtl, M. H. G. Angew. Chem., Int. Ed. 2015, 54, 10308.
[57] Kothandaraman, J.; Goeppert, A.; Czaun, M.; Olah, G. A.; Prakash, G. K. S. J. Am. Chem. Soc. 2016, 138, 778.
[58] Van de Watering, F. F.; Lutz, M.; Dzik, W. I.; de Bruin, B.; Reek, J. N. H. ChemCatChem 2016, 8, 2752.
[59] Shinoda, S.; Yamakawa, T. J. Chem. Soc., Chem. Commun. 1990, 1511.
[60] Shinoda, S.; Ohnishi, T.; Yamakawa, T. Catal. Sur. Asia 1997, 1, 25.
[61] Robles-Dutenhefnera, P. A.; Mourab, E. M.; Gamac, G. J. J. Mol. Catal. A Chem. 2000, 164, 39.
[62] Campos, J.; Sharninghausen, L. S.; Manas, M. G.; Crabtree, R. H. Inorg. Chem. 2015, 54, 5079.
[63] Manas, M. G.; Campos, J.; Sharninghausen, L. S.; Lin, E.; Crabtree, R. H. Green Chemistry 2015, 17, 594.
[64] Fujita, K.; Kawahara, R.; Aikawa, T.; Yamaguchi, R. Angew. Chem. 2015, 127, 9185.
[65] Prichatz, C.; Alberico, E.; Baumann, W.; Junge, H.; Beller, M. ChemCatChem 2017, 9, 1891.
[66] Shen, Y.; Zhan, Y.; Li, S.; Ning, F.; Du, Y.; Huang, Y.; He, T.; Zhou, X. Chem. Sci. 2017, 8, 7498.
[67] Morton, D.; Cole-Hamilton, D. J. J. Chem. Soc. Chem. Commun. 1987, 0, 248.
[68] Zhan, Y. L.; Shen, Y. B.; Li, S. P.; Yue, B. H.; Zhou, X. C. Chin. Chem. Lett. 2017, 28, 1353.
[69] Chai, H.-N.; Liu,B.; Liu, A.-Q.; Yu, K. J. Mol. Catal 2018, 32, 481(in Chinese). (柴会宁, 刘波, 刘爱芹, 喻琨, 分子催化, 2018, 32, 481.)
[70] Alberico, E.; Sponholz, P.; Cordes, C.; Nielsen, M.; Drexler, H. J.; Baumann, W.; Junge, H.; Beller, M. Angew. Chem., Int. Ed. Engl. 2013, 52, 14162.
[71] Bielinski, E. A.; Förster, M.; Zhang, Y.; Bernskoetter, W. H.; Hazari, N.; Holthausen, M. C. ACS Catal. 2015, 5, 2404.
[72] Wakizaka, M.; Matsumoto, T.; Tanaka, R.; Chang, H.-C. Nat. Commun. 2016, 7, 12333.
[73] Eisenstein, O.; Crabtree, R. H. New J. Chem. 2013, 37, 21.
[74] Andérez-Fernández.M; Vogt, L. K.; Fischer, S.; Zhou, W.; Jiao, H.; Garbe, M.; Elangovan, S.; Junge, K.; Junge, H.; Ludwig, R.; Beller, M. Angew. Chem., Int. Ed. Engl. 2017, 56, 559.
[75] Wei, Z.; de Aguirre, A.; Junge, K.; Beller, M.; Jiao, H. J. Catal. Sci. Technol. 2018, 8, 3649.

甲醇低温脱氢均相过渡金属催化剂研究进展