Efficient and stable Ru(III)-choline chloride catalyst system with low Ru content for non-mercury acetylene hydrochlorination

doi:10.1016/S1872-2067(18)63121-3

Abstract

Abstract:

Herein, we report an excellent, supported Ru(Ⅲ)-ChCl/AC catalyst with lower Ru content, where the ionic complex ChRuCl₄ serves as the active component for acetylene hydrochlorination. The prepared heterogeneous Ru-10%ChCl/AC catalyst shows excellent activity and long-term stability. In this system, ChCl provides an environment for the ChRuCl₄ to be stabilized as Ru(Ⅲ), thus suppressing the reduction of the active species and the aggregation of ruthenium species during the reaction. The interaction between reactants and catalyst species was investigated by catalyst characterizations in combination with DFT calculations to disclose the effect of the ChRuCl₄ complex and ChCl on the catalytic performance. This inexpensive, efficient, and long-term catalyst is a competitive candidate for application in the hydrochlorination industry.

Key words: Acetylene hydrochlorination, Catalytic activity, Heterogeneous catalysis, Ionic complex, Ruthenium

Hang Li, Botao Wu, Jianhui Wang, Fumin Wang, Xubin Zhang, Gang Wang, Haichao Li. Efficient and stable Ru(III)-choline chloride catalyst system with low Ru content for non-mercury acetylene hydrochlorination[J]. Chinese Journal of Catalysis, 2018, 39(11): 1770-1781.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(18)63121-3

https://www.cjcatal.com/EN/Y2018/V39/I11/1770

References

[1] X. Wei, H. Shi, W. Qian, G. Luo, Y. Jin, F. Wei, Ind. Eng. Chem. Res., 2008, 48, 128-133.
[2] K. Zhou, W. Wang, Z. Zhao, G. Luo, J. T. Miller, M. S. Wong, F. Wei, ACS Catal., 2014, 4, 3112-3116.
[3] H. Zhang, B. Dai, X. Wang, W. Li, Y. Han, J. Gu, J. Zhang, Green Chem., 2013, 15, 829-836.
[4] M. Conte, A. F. Carley, C. Heirene, D. J. Willock, P. Johnston, A. A. Herzing, C. J. Kiely, G. J. Hutchings, J. Catal., 2007, 250, 231-239.
[5] K. Zhou, J. Jia, C. Li, H. Xu, J. Zhou, G. Luo, F. Wei, Green Chem., 2015, 17, 356-364.
[6] X. Li, X. Pan, X. Bao, J. Energy Chem., 2014, 23, 131-135.
[7] T. V. Krasnyakova, I. V. Zhikharev, R. S. Mitchenko, V. I. Burkhovetski, А. M. Korduban, T. V. Kryshchuk, S. A. Mitchenko, J. Catal., 2012, 288, 33-43.
[8] S. A. Mitchenko, T. V. Krasnyakova, R. S. Mitchenko, A. N. Korduban, J. Mol. Catal. A, 2007, 275, 101-108.
[9] H. Zhang, B. Dai, W. Li, X. Wang, J. Zhang, M. Zhu, J. Gu, J. Catal., 2014, 316, 141-148.
[10] Y. Pu, J. Zhang, L. Yu, Y. Jin, W. Li, Appl. Catal. A, 2014, 488, 28-36.
[11] H. Li, F. Wang, W. Cai, J. Zhang, X. Zhang, Catal. Sci. Technol., 2015, 5, 5174-5184.
[12] K. Zhou, J. Jia, X. Li, X. Pang, C. Li, J. Zhou, G. Luo, F. Wei, Fuel Process. Technol., 2013, 108, 12-18.
[13] S. A. Panova, G. K. Shestakov, O. N. Temkin, J. Chem. Soc., Chem. Commun., 1994, 977-977.
[14] P. Johnston, N. Carthey, G. J. Hutchings, J. Am. Chem. Soc., 2015, 137, 14548-14557.
[15] J. Zhao, B. Wang, X. Xu, Y. Yu, S. Di, H. Xu, Y. Zhai, H. He, L. Guo, Z. Pan, X. Li, J. Catal., 2017, 350, 149-158.
[16] J. Zhao, S. Gu, X. Xu, T. Zhang, Y. Yu, X. Di, J. Ni, Z. Pan, X. Li, Catal. Sci. Technol., 2016, 6, 3263-3270.
[17] K. C. O'Connell, J. R. Monnier, J. Regalbuto, Appl. Catal. B, 2018, 225, 264-272.
[18] J. Zhang, W. Sheng, C. Guo, W. Li, RSC Adv., 2013, 3, 21062-21068.
[19] G. Li, W. Li, H. Zhang, Y. Pu, M. Sun, J. Zhang, RSC Adv., 2015, 5, 9002-9008.
[20] L. Hou, J. Zhang, Y. Pu, W. Li, RSC Adv., 2016, 6, 18026-18032.
[21] H. Zhang, W. Li, Y. Jin, W. Sheng, M. Hu, X. Wang, J. Zhang, Appl. Catal. B, 2016, 189, 56-64.
[22] M. Conte, A. F. Carley, G. J. Hutchings, Catal. Lett., 2008, 124, 165-167.
[23] M. Conte, C. J. Davies, D. J. Morgan, T. E. Davies, D. J. Elias, A. F. Carley, P. Johnston, G. J. Hutchings, J. Catal., 2013, 297, 128-136.
[24] M. Conte, A. F. Carley, G. Attard, A. A. Herzing, C. J. Kiely, G. J. Hutchings, J. Catal., 2008, 257, 190-198.
[25] S. Shang, W. Zhao, Y. Wang, X. Li, J. Zhang, Y. Han, W. Li, ACS Catal., 2017, 7, 3510-3520.
[26] H. Xu, K. Zhou, J. Si, C. Li, G. Luo, Catal. Sci. Technol., 2016, 6, 1357-1366.
[27] B. Nkosi, N. J. Coville, G. J. Hutchings, M. D. Adams, J. Friedl, F. E. Wagner, J. Catal., 1991, 128, 366-377.
[28] J. Hu, Q. Yang, L. Yang, Z. Zhang, B. Su, Z. Bao, Q. Ren, H. Xing, S. Dai, ACS Catal., 2015, 5, 6724-6731.
[29] J. Zhao, Y. Yu, X. Xu, S. Di, B. Wang, H. Xu, J. Ni, L. Guo, Z. Pan, X. Li, Appl. Catal. B, 2017, 206, 175-183.
[30] A. Romero, A. Santos, J. Tojo, A. Rodriguez, J. Hazard. Mater., 2008, 151, 268-273.
[31] A. P. Abbott, G. Capper, D. L. Davies, R. K. Rasheed, V. Tambyrajah, Green Chem., 2002, 4, 24-26.
[32] R. Calderon Morales, V. Tambyrajah, P. R. Jenkins, D. L. Davies, A. P. Abbott, Chem. Commun., 2004, 158-159.
[33] A. Zhu, T. Jiang, B. Han, J. Zhang, Y. Xie, X. Ma, Green Chem., 2007, 9, 169-172.
[34] K. Zhou, B. Li, Q. Zhang, J. Q. Huang, G. L. Tian, J. C. Jia, M. Q. Zhao, G. H. Luo, D. S. Su, F. Wei, ChemSusChem, 2014, 7, 723-728.
[35] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, M. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision C.01; Gaussian Inc.:Wallingford, CT, 2009.
[36] P. C. Hariharan, J. A. Pople, Theor. Chim. Acta., 1973, 28, 213-222.
[37] M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys., 1982, 77, 3654-3665.
[38] C. Lee, W. Yang, R. G. Parr, Phys. Rev. B, 1988, 37, 785-789.
[39] P. J. Hay, W. R. Wadt, J. Chem. Phys., 1985, 82, 299-310.
[40] T. H. Dunning Jr, P. J. Hay. Gaussian Basis Sets for Molecular Calculations, Springer, New York, 1977, 1-27.
[41] J. P. Merrick, D. Moran, L. Radom, J. Phys. Chem. A, 2007, 111, 11683-11700.
[42] A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys., 1985, 83, 735-746.
[43] A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B, 2009, 113, 6378-6396.
[44] F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys., 2005, 7, 3297-3305.
[45] S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys., 2010, 132, 154104.
[46] C. Y. C. b. Legault, Legault, C. Y, Université de Sherbrooke, Canada, 2009.
[47] T. Lu, F. Chen, J. Comput. Chem., 2012, 33, 580-592.
[48] W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graphics., 1996, 14, 33-38.
[49] A. P. Abbott, G. Capper, D. L. Davies, R. Rasheed, Inorg. Chem., 2004, 43, 3447-3452.
[50] C. Wagner, A. Naumkin, A. Kraut-Vass, J. Allison, C. Powell, J. Rumble Jr, National Institute of Standards and Technology:Gaithersburg, MD, 2003, 20899.
[51] A. S. Arico, P. CretI, P. L. Antonucci, J. Cho, H. Kim, V. Antonucci, Electrochim. Acta, 1998, 43, 3719-3729.
[52] R. Chetty, S. Kundu, W. Xia, M. Bron, W. Schuhmann, V. Chirila, W. Brandl, T. Reinecke, M. Muhler, Electrochim. Acta, 2009, 54, 4208-4215.
[53] S. Sharma, Z. Hu, P. Zhang, E. W. McFarland, H. Metiu, J. Catal., 2011, 278, 297-309.
[54] Y. Jin, G. Li, J. Zhang, Y. Pu, W. Li, RSC Adv., 2015, 5, 37774-37779.
[55] Y. Jia, R. Hu, Q. Zhou, H. Wang, X. Gao, J. Zhang, J. Catal., 2017, 348, 223-232.
[56] Q. Zhang, I. Lee, J. Ge, F. Zaera, Y. Yin, Adv. Funct. Mater., 2010, 20, 2201-2214.
[57] J. Zhao, Y. Yu, X. Xu, S. Di, B. Wang, H. Xu, J. Ni, L. L. Guo, Z. Pan, X. Li, Appl. Catal. B, 2017, 206, 175-183.
[58] X. Li, P. Li, X. Pan, H. Ma, X. Bao, Appl. Catal. B, 2017, 210, 116-120.
[59] D. He, X. Jiao, P. Jiang, J. Wang, B. Q. Xu, Green Chem., 2012, 14, 111-116.
[60] X. Li, M. Zhu, B. Dai, Appl. Catal. B, 2013, 142, 234-240.
[61] S. Chao, Q. Guan, W. Li, J. Catal., 2015, 330, 273-279.
[62] P. de Silva, C. Corminboeuf, J. Chem. Theory Comput., 2014, 10, 3745-3756.
[63] I. Mayer, Chem. Phys. Lett., 1983, 97, 270-274.
[64] A. D. Becke, K. E. Edgecombe, J. Chem. Phys., 1990, 92, 5397-5403.
[65] A. Savin, R. Nesper, S. Wengert, T. F. Fässler, Angew. Chem. Int. Ed., 1997, 36, 1808-1832.
[66] S. A. Mitchenko, T. V. Krasnyakova, R. S. Mitchenko, A. N. Korduban, J. Mol. Catal. A, 2007, 275, 101-108.
[67] Y. Han, M. Sun, W. Li, J. Zhang, Phys. Chem. Chem. Phys., 2015, 17, 7720-7730.
[68] S. Wang, B. Shen, Q. Song, Catal. Lett., 2010, 134, 102-109.
[69] B. d. B. Darwent, National Bureau of Standards, 1970.
[70] O. Eisenstein, R. Hoffmann, J. Am. Chem. Soc., 1980, 102, 6148-6149.
[71] B. Wang, J. L. Jiang, H. Z. Yu, Y. Fu, Organometallics, 2017, 36, 523-529.