Advances in development and industrial applications of ethylbenzene processes

doi:10.1016/S1872-2067(15)60965-2

Abstract

Abstract:

The benzene alkylation process for the production of ethylbenzene has undergone significant improvements during recent decades. Various environmentally benign zeolite-catalyzed ethylbenzene processes, including ZSM-5-zeolite-based vapor-phase ethylbenzene processes and Y-, β-, and MCM-22-zeolite-based liquid-phase processes, have been developed and commercialized. Pure ethylene, ethanol, and dilute ethylene have been used as ethylation agents. Here, the development and industrial application of alkylation catalysts and benzene ethylation techniques are summarized, and some other promising innovations are discussed. Recent advances in benzene alkylation over hierarchical zeolites with improved access to active sites and molecular transport are also covered. Zeolites with short diffusion lengths are promising candidates as better alkylation catalysts. The key point is how to obtain such materials easily and economically. The structure-activity relationships of commercial zeolites in these processes are discussed. Liquid-phase processes catalyzed by β and MCM-22 are more profitable than vapor-phase processes catalyzed by ZSM-5.

Key words: Ethylbenzene, Alkylation, Transalkylation, ZSM-5 zeolite, MCM-22 zeolite, Beta zeolite, Y zeolite

Weimin Yang, Zhendong Wang, Hongmin Sun, Bin Zhang. Advances in development and industrial applications of ethylbenzene processes[J]. Chinese Journal of Catalysis, 2016, 37(1): 16-26.

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https://www.cjcatal.com/EN/Y2016/V37/I1/16

References

[1] N. Mimura, M. Saito, Catal. Today, 2000, 55, 173.
[2] C. Perego, P. Ingallina, Catal. Today, 2002, 73, 3.
[3] K. Tanabe, W. F. Hölderich, Appl. Catal. A, 1999, 181, 399.
[4] A. A. O'Kelly, J. III Kellett, J. Plucker, Ind. Eng. Chem., 1947, 39, 154.
[5] W. M. Yang, H. M. Sun, S. J. Yang, H. F. Zhu, Shanghai Chem. Ind., 2002, (9-10), 16.
[6] J. R. Argauer, R. G. Landolt, US Patent 3 702 886, 1972.
[7] G. T. Kokotailo, S. L. Lawton, D. H. Olson, W. M. Meier, Nature, 1978, 272, 437.
[8] Z. K. Xie, Porous Catalytic Materials with New Structure and Improved Performance, China Petrochem. Press, Beijing, 2010, 4.
[9] N. Y. Chen, W. E. Garwood, Catal. Rev.-Sci. Eng., 1986, 28, 185.
[10] W. M. Yang, H. M. Sun, Q. L. Chen, Adv. Fine Petrochem., 2002, 3(4), 12.
[11] H. M. Sun, W. M. Yang, Q. L. Chen, Z. L. Xu, M. Jin, X. F. Shi, Ind. Catal., 2001, 9(5), 23.
[12] H. M. Sun, W. M. Yang, B. X. Liao, J. C. Zheng, Chem. React. Eng. Technol., 2006, 22, 206.
[13] M. Ni, D. Y. C. Leung, M. K. H. Leung, Int. J. Hydrogen Energy, 2007, 32, 3238.
[14] K. H. Chandawar, S. B. Kulkarni, P. Ratnasamy, Appl. Catal., 1982, 4, 287.
[15] X. W. Nie, X. Liu, C. S. Song, X. W. Guo, Chin. J. Catal., 2009, 30, 453.
[16] W. M. Yang, H. M. Sun, W. J. Liu, B. Zhang, Z. H. Shen, M. Y. Huan, H. Y. Zhang, US Patent 8 519 208, 2013.
[17] Y. J. Zhao, X. Zhang, C. L. Zhou, X. J. Jin, Contemp. Chem. Ind., 2011, 40, 1149.
[18] T. F. Degnan Jr, C. M. Smith, C. R. Venkat, Appl. Catal. A, 2001, 221, 283.
[19] F. C. Chen, X. X. Zhu, S. J. Xie, P. Zeng, Z. J. Guo, J. An, Q. X. Wang, S. L. Liu, L. Y. Xu, Chin. J. Catal., 2009, 30, 817.
[20] Y. Q. Wang, Petrochem. Technol., 2001, 30, 479.
[21] Q. X. Wang, S. R. Zhang, G. Y. Cai, F. Li, L. Y. Xu, Z. X. Huang, Y. Y. Li. US Patent 5 869 021, 1999.
[22] J. W. Li, J. Wang, X. L. Liu, G. Chen, C. L. Guo, J. Cong, L. Wang, L. Chen, Y. B. Wang, Chem. Ind. Eng. Progr., 2010, 29, 1790.
[23] S. Q. Gao, Nat. Gas Chem. Ind., 2010, 35(4), 55.
[24] Y. Zhang, Q. J. Tian, X. B .Ma, Petrol. Refinery Eng., 2012, 42(10), 59.
[25] J. L. Gou, Ind. Catal., 2014, 22, 397.
[26] C. G. Wight, US Patent 4 169 111, 1979.
[27] M. Rasouli, N. Yaghobi, S. Chitsazan, M. H. Sayyar, Microporous Mesoporous Mater., 2012, 152, 141.
[28] J. B. Higgins, R. B. LaPierre, J. L. Schlenker, A. C. Rohrman, J. D. Wood, G. T. Kerr, W. J. Rohrbaugh, Zeolites, 1988, 8, 446.
[29] R. L. Wadlinger, G. T. Kerr, E. J. Rosinski, US Patent 3 308 069, 1967.
[30] J. Aguado, D. P. Serrano, J. M. Rodríguez, Microporous Mesoporous Mater., 2008, 115, 504.
[31] G. Bellussi, G. Pazzuconi, C. Perego, G. Girotti, G. Terzoni, J. Catal., 1995, 157, 227.
[32] L. Forni, G. Gremona, F. Missineo, G. Bellussi, C. Perego, G. Pazzuconi, Appl. Catal. A, 1995, 121, 261.
[33] J. C. Cheng, A. S. Fung, D. J. Klocke, S. L. Lawton, D. N. Lissy, W. J. Roth, C. M. Smith, D. E. Walsh, US Patent 5 557 024, 1996.
[34] J. N. Armor, Appl. Catal. A, 2001, 222, 407.
[35] G. J. Gajda, R. T. Gajek, US Patent 5 522 984, 1996.
[36] J. Wang, F. M. Zhang, M. L. Li, C. Zhang, Petrol. Process Petrochem., 2002, 33(9), 13.
[37] Z. Y. Huang, S. X. Tian, Y. L. Xu, B. Zhu, W. D. Wang, F. M. Zhang, X. Wang, US Patent 5 600 050, 1997.
[38] H. L. Dai, Aromatic Technology, China Petrochem Press, Beijing, 2014, 524.
[39] Y. Wang, Y. M. Liu, L. L. Wang, H. H. Wu, X. H. Li, M. Y. He, P. Wu, J. Phys. Chem. C, 2009, 113, 18753.
[40] L. M. Rohde, G. J. Lewis, M. A. Miller, J. G. Moscoso, J. L. Gisselquist, R. L. Patton, S. T. Wilson, D. Y. Jan, US Patent 6 756 030, 2004.
[41] W. J. Roth, T. Yorke, D. L. Dorset, M. Kalyanaraman, M. C. Kerby, S. C. Weston, US Patent 8 110 176, 2012.
[42] W. J. Roth, D. L. Dorset, G. J. Kennedy, T. Yorke, T. E. Helton, US Patent 8 704 025, 2014.
[43] W. J. Roth, D. L. Dorset, G. J. Kennedy, T. Yorke, T. E. Helton, P. Ghosh, Y. V. Joshi, US Patent 8 704 023, 2014.
[44] M. E. Leonowicz, J. A. Lawton, S. L. Lawton, M. K. Rubin, Science, 1994, 264, 1910.
[45] D. Y. Jan, J. A. Johnson, R. J. Schmidt, G. B. Woodle, US Patent 7 268 267, 2007.
[46] D. Y. Jan, J. A. Johnson, R. J. Schmidt, M. P. Koljack, US Patent 8 518 847, 2013.
[47] D. B. Lukyanov, T. Vazhnova, J. Catal., 2008, 257, 382.
[48] S. Kato, K. Nakagawa, N. O. Ikenaga, T. Suzuki, Catal. Lett., 2001, 73, 175.
[49] T. Odedairo, S. Al-Khattaf, Appl. Catal. A, 2010, 385, 31.
[50] M. Raimondo, G. Perez, A. De Stefanis, A. A. G. Tomlinson, O. Ursini, Appl. Catal. A, 1997, 164, 119.
[51] M. Bevilacqua, D. Meloni, F. Sini, R. Monaci, T. Montanari, G. Busca, J. Phys. Chem. C, 2008, 112, 9023.
[52] J. C. Cheng, T. F. Degnan, J. S. Beck, Y. Y. Huang, M. Kalyanaraman, J. A. Kowalski, C. A. Loehr, D. N. Mazzone, Stud. Surf. Sci. Catal., 1999, 121, 53.
[53] Z. D. Wang, Y. X. Zhang, B. Zhang, H. M. Sun, W. M. Yang, Acta Petrol. Sin. (Petrol. Process Sect.), 2014, 30(1), 110.
[54] J. C. Kim, K. Cho, R. Ryoo, Appl. Catal. A, 2014, 470, 420.
[55] N. N. Gao, S. J. Xie, S. L. Liu, W. J. Xin, Y. Gao, X. J. Li, H. J. Wei, H. Liu, L. Y. Xu, Microporous Mesoporous Mater., 2015, 212, 1.
[56] J. Pérez-Ramírez, C. H. Christensen, K. Egeblad, C. H. Christensen, J. C. Groen, Chem. Soc. Rev., 2008, 37, 2530.
[57] K. F. Liu, S. J. Xie, G. L. Xu, Y. N. Li, S. L. Liu, L. Y. Xu, Appl. Catal. A, 2010, 383, 102.
[58] B. Zhang, Z. D. Wang, P. Ji, Y. M. Liu, H. M. Sun, W. M. Yang, P. Wu, Microporous Mesoporous Mater., 2013, 179, 63.
[59] M. Horňá?ek, P. Hudec, K. Velebná, P. Lovás, Catal. Commun., 2015, 64, 1.
[60] Y. Y. Sun, R. Prins, Appl. Catal. A, 2008, 336, 11.
[61] C. H. Christensen, K. Johannsen, I. Schmidt, C. H. Christensen, J. Am. Chem. Soc., 2003, 125, 13370.
[62] M. S. Holm, E. Taarning, K. Egeblad, C. H. Christensen, Catal. Today, 2011, 168, 3.
[63] R. C. Runnebaum, X. Ouyang, J. A. Edsinga, T. Rea, I. Arslan, S. J. Hwang, S. I. Zones, A. Katz, ACS Catal., 2014, 4, 2364.
[64] W. Kim, J. C. Kim, J. Kim, Y. Seo, R. Ryoo, ACS Catal., 2013, 3, 192.
[65] A. Corma, V. Fornés, J. Martínez-Triguero, S. B. C. Pergher, J. Catal., 1999, 186, 57.
[66] J. Aguilar, S. B. C. Pergher, C. Detoni, A. Corma, F. V. Melo, E. Sastre, Catal. Today, 2008, 133-135, 667.
[67] A. Corma, V. Martínez-Soria, E. Schnoeveld, J. Catal., 2000, 192, 163.
[68] H. W. Du, D. H. Olson, J. Phys. Chem. B, 2002, 106, 395.
[69] A. Corma, V. Fornés, J. M. Guil, S. Pergher, Th. L. M. Maesen, J. G. Buglass, Mircroporous Mesoporous Mater., 2000, 38, 301.
[70] C. T. Kresge, W. J. Roth, US Patent 5 278 115, 1994.
[71] X. B. Ma, F. C. Ruan, Ind. Catal., 2014, 22, 632.
[72] X. J. Meng, F. S. Xaio, Chem. Rev., 2014, 114, 1521.
[73] B. Xie, H. Y. Zhang, C. G. Yang, S. Y. Liu, L. M. Ren, L. Zhang, X. J. Meng, B. Yilmaz, U. Müller, F. S. Xiao, Chem. Commun., 2011, 47, 3945.
[74] B. Xie, J. W. Song, L. M. Ren, Y. Y. Ji, J. X. Li, F. S. Xiao, Chem. Mater., 2008, 20, 4533.
[75] L. M. Ren, Q. M. Wu, C. G. Yang, L. F. Zhu, C. J. Li, P. L. Zhang, H. Y. Zhang, X. J. Meng, F. S. Xiao, J. Am. Chem. Soc., 2012, 134, 15173.
[76] Y. Y. Jin, Q. Sun, G. D. Qi, C. G. Yang, J. Xu, F. Chen, X. J. Meng, F. Deng, F. S. Xiao, Angew. Chem. Int. Ed., 2013, 52, 9172.
[77] S. Q. Wei, F. F. Qu, CN Patent 102 092 740, 2011.
[78] Y. C. Shi, E. H. Xing, W. H. Xie, F. M. Zhang, X. H. Mu, X. T. Shu, RSC Adv., 2015, 5, 13420.
[79] E. H. Xing, Y. C. Shi, A. G. Zheng, J. Zhang, X. Z. Gao, D. Y. Liu, M. D. Xin, W. H. Xie, F. M. Zhang, X. H. Mu, X. T. Shu, Ind. Eng. Chem. Res., 2015, 54, 3123.
[80] A. Galadima, O. Muraza, Microporous Mesoporous Mater., 2015, 213, 169.
[81] M. C. Clark, B. S. Umansky, E. A. Nye, M. J. Reichensperger, W. C. Lewis, US Patent 8 395 006, 2013.
[82] A. A. Chin, N. A. Collins, M. N. Harandi, R. T. Thomson, R. A. Ware, US Patent 5 491 270, 1996.
[83] O. Graf P., L. Lefferts, Chem. Eng. Sci., 2009, 64, 2773.