Aluminum impregnated silica catalyst for Friedel-Crafts reaction:Influence of ordering mesostructure

doi:10.1016/j.cjche.2016.11.005

摘要/Abstract

摘要： Friedel-Crafts alkylation of benzene with linear chain olefin (C₁₀-C₁₄), which is an important reaction of synthetic detergent, was studied via different catalysts of aluminum impregnated silica molecular sieves. AlCl3 was immobilized on silica molecular sieves with different channel structures, hexagonal packing channels network (SBA-15, MCM-41), and disordered channel network (SiO₂, SiO₂-Gel) by impregnation. XRD and N₂ adsorption-desorption isotherms confirmed that the specific mesoporous structures were maintained for order channel network catalyst after impregnation. Catalytic activities were investigated under different conditions. The influences of channel structure were discussed. The results showed that catalyst based on mesoporous like SBA-15 had the highest catalytic activities and 2-LAB selectivity compared with other catalysts in this work. The highest 2-LAB selectivity was nearly 50% when 1-dodecene conversion was nearly 100%. At low 1-dodecene conversion or higher benzene/1-dodecene molar ratio, 2-LAB selectivity was nearly 60%.

关键词: Friedel-Crafts, Alkylation, Aluminum, Catalyst, Molecular sieves

Abstract: Friedel-Crafts alkylation of benzene with linear chain olefin (C₁₀-C₁₄), which is an important reaction of synthetic detergent, was studied via different catalysts of aluminum impregnated silica molecular sieves. AlCl3 was immobilized on silica molecular sieves with different channel structures, hexagonal packing channels network (SBA-15, MCM-41), and disordered channel network (SiO₂, SiO₂-Gel) by impregnation. XRD and N₂ adsorption-desorption isotherms confirmed that the specific mesoporous structures were maintained for order channel network catalyst after impregnation. Catalytic activities were investigated under different conditions. The influences of channel structure were discussed. The results showed that catalyst based on mesoporous like SBA-15 had the highest catalytic activities and 2-LAB selectivity compared with other catalysts in this work. The highest 2-LAB selectivity was nearly 50% when 1-dodecene conversion was nearly 100%. At low 1-dodecene conversion or higher benzene/1-dodecene molar ratio, 2-LAB selectivity was nearly 60%.

Key words: Friedel-Crafts, Alkylation, Aluminum, Catalyst, Molecular sieves

Yibo He, Qinghua Zhang, Xiaoli Zhan, Dangguo Cheng, Fengqiu Chen. Aluminum impregnated silica catalyst for Friedel-Crafts reaction:Influence of ordering mesostructure[J]. , 2017, 25(10): 1533-1538.

参考文献

[1] A. Aitani, J. Wang, I. Wang, S. Al-Khattaf, T. Tsai, Environmental benign catalysis for linear alkylbenzene synthesis:A review, Catal. Surv. Jpn. 18(1) (2014) 1-12.
[2] G.D. Yadav, M.I.N.I. Siddiqui, UDCaT-5:a novel mesoporous superacid catalyst in the selective synthesis of linear phenyldodecanes by the alkylation of benzene with 1-dodecene, Ind. Eng. Chem. Res. 48(24) (2009) 10803-10809.
[3] D.P. Fogliatti, S.A. Kemppainen, T.N. Kalnes, J. Fan, D.R. Shonnard, Life cycle carbon footprint of linear alkylbenzenesulfonate from coconut oil, palm kernel oil, and petroleum-based paraffins, ACS Sustain. Chem. Eng. 2(7) (2014) 1828-1834.
[4] B. Wang, C.W. Lee, T.X. Cai, S.E. Park, Benzene alkylation with 1-dodecene over Y zeolite, Bull. Kor. Chem. Soc. 22(9) (2001) 1056-1058.
[5] R.J. Larson, T.M. Rothgeb, R.J. Shimp, T.E. Ward, R.M. Ventullo, Kinetics and practical significance of biodegradation of linear alkylbenzene sulfonate in the environment, J. Am. Oil Chem. Soc. 70(7) (1993) 645-657.
[6] A.M. Nielsen, L.N. Britton, C.E. Beall, T.P. McCormick, G.L. Russell, Biodegradation of coproducts of commercial linear alkylbenzene sulfonate, Environ. Sci. Technol. 31(12) (1997) 3397-3404.
[7] J. Lin, J. Wang, J. Wang, I. Wang, R.J. Balasamy, A. Aitani, S. Al-Khattaf, T. Tsai, Catalysis of alkaline-modified Mordenite for benzene alkylation of diolefincontaining dodecene for linear alkylbenzene synthesis, J. Catal. 300(2013) 81-90.
[8] R. Kumar, A. Kumar, A. Khanna, Synthesis, characterization and kinetics of AlCl₃ supported on silica superacid catalysts for the formation of linear alkylbenzenes, React. Kinet. Mech. Catal. 106(1) (2012) 141-155.
[9] J. Kang, Y. Rao, M. Trudeau, D. Antonelli, Sulfated mesoporous tantalum oxides in the shape selective synthesis of linear alkyl benzene, Angew. Chem. Int. Ed. 47(26) (2008) 4896-4899.
[10] N. Pal, A. Bhaumik, Mesoporous materials:Versatile supports in heterogeneous catalysis for liquid phase catalytic transformations, RSC Adv. 5(31) (2015) 24363-24391.
[11] M.S. Holm, E. Taarning, K. Egeblad, C.H. Christensen, Catalysis with hierarchical zeolites, Catal. Today 168(1) (2011) 3-16.
[12] M. Horňáček, P. Hudec, K. Velebná, P. Lovás, Positive effect of secondary structure creation in mordenites on alkylation of benzene with 1-tetradecene, Catal. Commun. 64(2015) 1-5.
[13] X. Hu, M.L. Foo, G.K. Chuah, S. Jaenicke, Pore size engineering on MCM-41:Selectivity tuning of heterogenized AlCl₃ for the synthesis of linear alkyl benzenes, J. Catal. 195(2) (2000) 412-415.
[14] D. Sengupta, J. Saha, G. De, B. Basu, Pd/Cu bimetallic nanoparticles embedded in macroporous ion-exchange resins:An excellent heterogeneous catalyst for the Sonogashira reaction, J. Mater. Chem. A 2(11) (2014) 3986.
[15] C.M.A. Parlett, K. Wilson, A.F. Lee, Hierarchical porous materials:Catalytic applications, Chem. Soc. Rev. 42(9) (2013) 3876-3893.
[16] D. Dubé, S. Royer, D. Trong On, F. Béland, S. Kaliaguine, Aluminum chloride grafted mesoporous molecular sieves as alkylation catalysts, Microporous Mesoporous Mater. 79(1-3) (2005) 137-144.
[17] A. Bordoloi, B.M. Devassy, P.S. Niphadkar, P.N. Joshi, S.B. Halligudi, Shape selective synthesis of long-chain linear alkyl benzene (LAB) with AlMCM-41/beta zeolite composite catalyst, J. Mol. Catal. A Chem. 253(1-2) (2006) 239-244.
[18] Y. Cao, R. Kessas, C. Naccache, Y. Ben Taarit, Alkylation of benzene with dodecene. The activity and selectivity of zeolite type catalysts as a function of the porous structure, Appl. Catal. A Gen. 184(2) (1999) 231-238.
[19] J. Wang, H.O. Zhu, Alkylation of 1-dodecene with benzene over H₃PW₁₂O₄₀ supported on mesoporous silica SBA-15, Catal. Lett. 93(3-4) (2004) 209-212.
[20] C. Anand, B. Sathyaseelan, L. Samie, A. Beitollahi, R. Pradeep Kumar, M. Palanichamy, V. Murugesan, E. Kenawy, S.S. Al-Deyab, A. Vinu, Friedel-Crafts benzylation of benzene and other aromatics using 3D mesoporous gallosilicate with cage type porous structure, Microporous Mesoporous Mater. 134(1-3) (2010) 87-92.
[21] S. Selvakumar, A.P. Singh, Benzoylation of anisole over silicotungstic acid modified mesoporous alumina, Catal. Lett. 128(3-4) (2009) 363-372.
[22] J. Dou, H.C. Zeng, Preparation of Mo-embedded mesoporous carbon microspheres for Friedel-Crafts alkylation, J. Phys. Chem. C 116(14) (2012) 7767-7775.
[23] Y. Rao, M. Trudeau, D. Antonelli, Sulfated and phosphated mesoporous Nb oxide in the benzylation of anisole and toluene by benzyl alcohol, J. Am. Chem. Soc. 128(43) (2006) 13996-13997.
[24] X. Zhang, T. Lin, R. Li, T. Bai, G. Zhang, Properties and reactivity of Fe-P-O catalysts prepared by different methods for benzylation of benzene, Ind. Eng. Chem. Res. 51(9) (2012) 3541-3549.
[25] B. Wang, C.W. Lee, T. Cai, S. Park, Benzene alkylation with 1-dodecene over H-mordenite zeolite, Catal. Lett. 76(1) (2001) 99-103.
[26] Y. Sugi, H. Tamada, A. Kuriki, K. Komura, Y. Kubota, S. Joseph, A. Chokkalingam, M.E. Newehy, S.S. Al-Deyab, H. Jang, J. Kim, G. Seo, A. Vinu, Alkaline earth metal modified H-Mordenites. Their catalytic properties in the isopropylation of biphenyl, Ind. Eng. Chem. Res. 54(49) (2015) 12283-12292.
[27] S. Huang, S. Zhang, L. Yu, Z. Liu, W. Xin, S. Xie, L. Xu, Transalkylation of phenol with cumene on zeolite catalysts, Ind. Eng. Chem. Res. 52(32) (2013) 10996-11000.
[28] M. Osman, M.M. Hossain, S. Al-Khattaf, Kinetics study of ethylbenzene alkylation with ethanol over medium and large pore zeolites, Ind. Eng. Chem. Res. 52(38) (2013) 13613-13621.
[29] K. Raveendranath Reddy, D. Venkanna, M. Lakshmi Kantam, S.K. Bhargava, P. Srinivasu, SnO₂-SiO₂ mesoporous composite:A very active catalyst for regioselective synthesis of aromatic ketones with unusual catalytic behavior, Ind. Eng. Chem. Res. 54(28) (2015) 7005-7013.
[30] P.V. Naumkin, T.N. Nesterova, I.A. Nesterov, A.M. Toikka, V.A. Shakun, Theory and practice of alkyl aromatic hydrocarbon synthesis. 1. Branched alkylbenzenes, Ind. Eng. Chem. Res. 54(35) (2015) 8629-8639.
[31] S. Liu, F. Chen, S. Xie, P. Zeng, X. Du, L. Xu, Highly selective ethylbenzene production through alkylation of dilute ethylene with gas phase-liquid phase benzene and transalkylation feed, J. Nat. Gas Chem. 18(1) (2009) 21-24.
[32] H. Wu, M. Liu, W. Tan, K. Hou, A. Zhang, Y. Wang, X. Guo, Effect of ZSM-5 zeolite morphology on the catalytic performance of the alkylation of toluene with methanol, J. Energy Chem. 23(4) (2014) 491-497.
[33] H. Liu, H. Wei, W. Xin, C. Song, S. Xie, Z. Liu, S. Liu, L. Xu, Differences between Zn/HZSM-5 and Zn/HZSM-11 zeolite catalysts in alkylation of benzene with dimethyl ether, J. Energy Chem. 23(5) (2014) 617-624.
[34] Bokade, Deshpande, Patil, Jain, Yadav, Toluene alkylation with methanol to p-xylene over heteropoly acids supported by clay, J. Nat. Gas Chem. 16(1) (2007) 42-45.
[35] D.Y. Zhao, J.L. Feng, Q.S. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Triblock copolymer synthesesof mesoporoussilica with periodic 50 to 300 angstrom pores, Science 279(5350) (1998) 548-552.
[36] V.R. Choudhary, K. Mantri, AlCl₃-grafted Si-MCM-41:Influence of thermal treatment conditions on surface properties and incorporation of Al in the structure of MCM-41, J. Catal. 205(1) (2002) 221-225.
[37] D. Kim, D. Lim, D. Cho, J. Koh, D. Park, Production of dimethyl carbonate from ethylene carbonate and methanol using immobilized ionic liquids on MCM-41, Catal. Today 164(1) (2011) 556-560.
[38] W. Chen, S. Huang, Q. Zhao, H. Lin, C. Mou, S. Liu, On the confinement effect during catalytic reaction over Al-MCM-41, Top. Catal. 52(1-2) (2009) 2-11.
[39] D. Li, F. Shi, S. Guo, Y. Deng, One-pot synthesis of silica gel confined functional ionic liquids:Effective catalysts for deoximation under mild conditions, Tetrahedron Lett. 45(2) (2004) 265-268.
[40] D. Li, F. Shi, Y. Deng, One-step CN, CO bonds cleavage and CO, CN bonds formation over supported ionic liquid in water, Tetrahedron Lett. 45(36) (2004) 6791-6794.
[41] H. Xin,Q.Wu,M.Han, D.Wang,Y. Jin,Alkylation of benzene with 1-dodeceneinionic liquids[Rmim]⁺Al₂Cl₆X -(R=butyl, octylanddodecyl;X=chlorine, bromineand iodine), Appl. Catal. A Gen. 292(2005) 354-361.
[42] G. Qi, F. Jiang, X. Sun, S. Zhao, Alkylation mechanism of benzene with 1-dodecene catalyzed by Et₃NHCl-AlCl₃, Sci. China Chem. 53(5) (2010) 1102-1107.
[43] R.M. Grudzien, B.E. Grabicka, M. Jaroniec, Adsorption and structural properties of channel-like and cage-like organosilicas, Adsorption 12(5-6) (2006) 293-308.
[44] T. Kim, R. Ryoo, M. Kruk, K.P. Gierszal, M. Jaroniec, S. Kamiya, O. Terasaki, Tailoring the pore structure of SBA-16 silica molecular sieve through the use of copolymer blends and control of synthesis temperature and time, J. Phys. Chem. B 108(31) (2004) 11480-11489.
[45] G.Peterson, UOP Technology and More Newsletter, UOP LLC,Des Plaines,sept 2011.
[46] J.Carrazza, M.Cleveland, B.Vora, Presented at the Middle East Petrotech, May 2012.