Deactivation mechanism of beta-zeolite catalyst for synthesis of cumene by benzene alkylation with isopropanol

doi:10.1016/j.cjche.2016.11.001

›› 2017, Vol. 25 ›› Issue (9): 1195-1201.DOI: 10.1016/j.cjche.2016.11.001

• Catalysis, kinetics and reaction engineering • Previous Articles Next Articles

Deactivation mechanism of beta-zeolite catalyst for synthesis of cumene by benzene alkylation with isopropanol

Yefei Liu¹, Yang Zou¹, Hong Jiang¹, Huanxin Gao², Rizhi Chen¹

1 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 SINOPEC Shanghai Research Institute of Petrochemical Technology, Shanghai 201208, China

Received:2016-07-21 Revised:2016-11-09 Online:2017-10-11 Published:2017-09-28
Supported by:
Supports by the National Key Research and Development Plan (2016YFB0301503), the Jiangsu Natural Science Foundation for Distinguished Young Scholars (BK20150044), the National Natural Science Foundation of China (91534110, 21606124), the Natural Science Foundation of the Higher Education Institutions of Jiangsu Province (14KJB530004), the Foundation from State Key Laboratory of Materials-Oriented Chemical Engineering (ZK201402, ZK201407), and the Technology Innovation Foundation for Science and Technology Enterprises in Jiangsu Province (BC2015008).

Deactivation mechanism of beta-zeolite catalyst for synthesis of cumene by benzene alkylation with isopropanol

Yefei Liu¹, Yang Zou¹, Hong Jiang¹, Huanxin Gao², Rizhi Chen¹

1 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 SINOPEC Shanghai Research Institute of Petrochemical Technology, Shanghai 201208, China

通讯作者: Rizhi Chen,E-mail:rizhichen@njtech.edu.cn
基金资助:
Supports by the National Key Research and Development Plan (2016YFB0301503), the Jiangsu Natural Science Foundation for Distinguished Young Scholars (BK20150044), the National Natural Science Foundation of China (91534110, 21606124), the Natural Science Foundation of the Higher Education Institutions of Jiangsu Province (14KJB530004), the Foundation from State Key Laboratory of Materials-Oriented Chemical Engineering (ZK201402, ZK201407), and the Technology Innovation Foundation for Science and Technology Enterprises in Jiangsu Province (BC2015008).

Abstract

Abstract: The alkylation of benzene with isopropanol over beta-zeolite is a more cost-effective solution to cumene production. During the benzene alkylation cycles, the cumene selectivity slowly increased, while the benzene conversion presented the sharp decrease due to catalyst deactivation. The deactivation mechanism of betazeolite catalyst was investigated by characterizing the fresh and used catalysts. The XRD, SEM and TEM results show that the crystalline and particle size of the beta-zeolite catalyst almost remained stable during the alkylation cycles. The drop in catalytic activity and benzene conversion could be explained by the TG, BET, NH₃-TPD and GC-MS results. The organic matters mainly consisted of ethylbenzene, p-xylene and 1-ethyl-3-(1-methyl) benzene produced in the benzene alkylation deposited in the catalyst, which strongly reduced the specific surface area of beta-zeolite catalyst. Moreover, during the reaction cycles, the amount of acidity also significantly decreased. As a result, the catalyst deactivation occurred. To maintain the catalytic performance, the catalyst regeneration was carried out by using ethanol rinse and calcination. The deactivated catalyst could be effectively regenerated by the calcination method and the good catalytic performance was obtained.

Key words: Cumene, Benzene, Isopropanol, Alkylation, Beta-zeolite, Catalyst deactivation

摘要： The alkylation of benzene with isopropanol over beta-zeolite is a more cost-effective solution to cumene production. During the benzene alkylation cycles, the cumene selectivity slowly increased, while the benzene conversion presented the sharp decrease due to catalyst deactivation. The deactivation mechanism of betazeolite catalyst was investigated by characterizing the fresh and used catalysts. The XRD, SEM and TEM results show that the crystalline and particle size of the beta-zeolite catalyst almost remained stable during the alkylation cycles. The drop in catalytic activity and benzene conversion could be explained by the TG, BET, NH₃-TPD and GC-MS results. The organic matters mainly consisted of ethylbenzene, p-xylene and 1-ethyl-3-(1-methyl) benzene produced in the benzene alkylation deposited in the catalyst, which strongly reduced the specific surface area of beta-zeolite catalyst. Moreover, during the reaction cycles, the amount of acidity also significantly decreased. As a result, the catalyst deactivation occurred. To maintain the catalytic performance, the catalyst regeneration was carried out by using ethanol rinse and calcination. The deactivated catalyst could be effectively regenerated by the calcination method and the good catalytic performance was obtained.

关键词: Cumene, Benzene, Isopropanol, Alkylation, Beta-zeolite, Catalyst deactivation

Yefei Liu, Yang Zou, Hong Jiang, Huanxin Gao, Rizhi Chen. Deactivation mechanism of beta-zeolite catalyst for synthesis of cumene by benzene alkylation with isopropanol[J]. , 2017, 25(9): 1195-1201.

References

[1] Y.H. Bao, H. Jiang, W.H. Xing, R.Z. Chen, Y.Q. Fan, Liquid phase hydroxylation of benzene to phenol over vanadyl acetylacetonate supported on amine functionalized SBA-15, React. Kinet. Mech. Catal. 116(2) (2015) 535-547.
[2] H. Jiang, F. She, Y. Du, R.Z. Chen, W.H. Xing, One-step continuous phenol synthesis technology via selective hydroxylation of benzene over ultrafine TS-1 in a submerged ceramic membrane reactor, Chin. J. Chem. Eng. 22(11-12) (2014) 1199-1207.
[3] C.C. Huang, J.J. Peng, S.H. Wu, H.Y. Hou, M.L. You, C.M. Shu, Effects of cumene hydroperoxide on phenol and acetone manufacturing by DSC and VSP2, J. Therm. Anal. Calorim. 102(2) (2010) 579-585.
[4] G.D. Yadav, Z.S. Asthana, Selective decomposition of cumene hydroperoxide into phenol and acetone by a novel cesium substituted heteropolyacid on clay, Appl. Catal. A Gen. 244(2) (2003) 341-357.
[5] M.H. Han, S.X. Lin, E. Roduner, Study on the alkylation of benzene with propylene over Hβ zeolite, Appl. Catal. A Gen. 243(1) (2003) 175-184.
[6] Z.G. Lei, C.N. Dai, Y.L. Wang, B.H. Chen, Process optimization on alkylation of benzene with propylene, Energy Fuel 23(6) (2009) 3159-3166.
[7] W. Tecza, R. Brzozowski, Modern industrial processes for making ethylbenzene and cumene, Przem. Chem. 82(11) (2003) 1428-1434.
[8] J. Horsley, Producing bulk and fine chemicals using solid acids, ChemTech 27(10) (1997) 45-49.
[9] G.J. Gajda, R.L. Patton, S.T. Wilson, Discrete Molecular Sieve and Use in AromaticOlefin Alkylation, UOP Inc., 1995(US 5434326).
[10] S. Barman, N.C. Pradhan, J.K. Basu, Kinetics of alkylation of benzene with isopropyl alcohol over Ce-exchanged NaX zeolite, Ind. Eng. Chem. Res. 44(19) (2005) 7313-7319.
[11] V.V. Bokade, U.K. Kharul, Selective synthesis of cumene by isopropylation of benzene using catalytic membrane reactor, Chem. Eng. J. 147(2-3) (2009) 97-101.
[12] G. Girotti, F. Rivetti, S. Ramello, L. Carnelli, Alkylation of benzene with isopropanol on zeolite influence of physical state and water concentration on catalyst performances, J. Mol. Catal. A Chem. 204-205(2003) 571-579.
[13] C.A.A. Monteiro, D. Costa, J.L. Zotin, D. Cardoso, Effect of metal-acid site balance on hydroconversion of decalin over Pt Beta zeolite bifunctional catalysts, Fuel 160(2015) 71-79.
[14] Y. Sugi, A. Vinu, Alkylation of biphenyl over zeolites shape-selective catalysis in zeolite channels, Catal. Surv. Jpn. 19(3) (2015) 188-120.
[15] M.D. Argyle, C.H. Bartholomew, Heterogeneous catalyst deactivation and regeneration:A review, Catalysts 5(1) (2015) 145-269.
[16] Y.S. You, J.H. Kim, G. Seo, Liquid-phase catalytic degradation of polyethylene wax over silica-modified zeolite catalysts, Polym. Degrad. Stab. 72(2) (2001) 329-336.
[17] C.C. Wang, H. Jiang, C.L. Chen, R.Z. Chen, W.H. Xing, A submerged catalysis membrane filtration system for hydrogenolysis of glycerol to 1,2-propanediol over Cu-ZnO catalyst, J. Membr. Sci. 489(2015) 135-143.
[18] H. Jiang, Z.Y. Qu, Y. Li, J. Huang, R.Z. Chen, W.H. Xing, One-step semi-continuous cyclohexanone production via hydrogenation of phenol in a submerged ceramic membrane reactor, Chem. Eng. J. 284(2016) 724-732.
[19] A. van Miltenburg, J. Pawlesa, A.M. Bouzga, N. Žilková, J. Čejka, M. Stöcker, Alkaline modification of MCM-22 to a 3D interconnected pore system and its application in toluene disproportionation and alkylation, Top. Catal. 52(9) (2009) 1190-1202.
[20] J.M. Newsam, M.M.J. Treacy, W.T. Koetsier, C.B.D. Gruyter, Structural characterization of zeolite beta, Proc. R. Soc. A Math. Phys. 420(1859) (1988) 375-405.
[21] J.C. Kim, K. Cho, High catalytic performance of surfactant-directed nanocrystalline zeolites for liquid phase alkylation of benzene due to external surfaces, Appl. Catal. A Gen. 470(2014) 420-426.
[22] J.Q. Fu, T.B. Cao, Influence of coke-burning regeneration using steam-containing air flow on dealumination of beta zeolite catalyst, Chin. J. Catal. 24(11) (2003) 811-815.
[23] H.S. Cerqueira, P. Ayrault, J. Datka, M. Guisnet, Influence of coke on the acid properties of a USHY zeolite, Microporous Mesoporous Mater. 38(2-3) (2000) 197-205.
[24] C. Qin, Y. Chen, J.M. Cao, Manufacture and characterization of activated carbon from marigold straw (Tagetes erecta L) by H₃PO₄ chemical activation, Mater. Lett. 135(2014) 123-126.
[25] A.J. Duan, G.F. Wan, Y. Zhang, Z. Zhao, G.Y. Jiang, J. Liu, Optimal synthesis of micro mesoporous beta zeolite from kaolin clay and catalytic performance for hydrodesulfurization of diesel, Catal. Today 175(1) (2011) 485-493.
[26] C. Kalamaras, D. Palomas, R. Bos, A. Horton, M. Crimmin, K. Hellgardt, Selective oxidation of methane to methanol over Cu-and Fe-exchanged zeolites:The effect of Si/Al molar ratio, Catal. Lett. 146(2) (2016) 483-492.
[27] A.V. Tokarev, L.V. Malysheva, E.A. Paukshtis, Effect of thermal treatment conditions on the acid properties of zeolite beta, Kinet. Catal. 51(2) (2010) 318-324.
[28] W.L. Dai, X.M. Sun, B. Tang, G.J. Wu, L.D. Li, N.J. Guan, M. Hunger, Verifying the mechanism of the ethene-to-propene conversion on zeolite H-SSZ-13, J. Catal. 314(2014) 10-20.
[29] G.J. Wu, Y. Hao, N. Zhang, N.J. Guan, L.D. Li, W. Grünert, Oxidative dehydrogenation of propane with nitrous oxide over Fe-O-Al species occluded in ZSM-5:Reaction and deactivation mechanisms, Microporous Mesoporous Mater. 198(2014) 82-91.
[30] Z.Z. Wen, X.H. Yu, S.T. Tu, J.Y. Yan, E. Dahlquist, Biodiesel production from waste cooking oil catalyzed by TiO₂-MgO mixed oxides, Bioresour. Technol. 101(24) (2010) 9570-9576.
[31] Y.J.Liu,E.Lotero,J.G.Goodwin,X.H.Mo,Transesterificationofpoultryfatwithmethanol using Mg-Al hydrotalcite derived catalysts, Appl. Catal. A Gen. 331(1) (2007) 138-148.

Deactivation mechanism of beta-zeolite catalyst for synthesis of cumene by benzene alkylation with isopropanol

Deactivation mechanism of beta-zeolite catalyst for synthesis of cumene by benzene alkylation with isopropanol

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