269199 Shape-Selective Alkylation of Biphenyl with Propylene by Using Zeolite Catalysts

Thursday, November 1, 2012: 12:50 PM
321 (Convention Center )
Venkat Ramana Rao Pendyala, Wilson D. Shafer, Gary Jacobs, Dennis E. Sparks and Burtron H. Davis, Center for Applied Energy Research, University of Kentucky, Lexington, KY

The alkylation of biphenyl with propylene is a reaction of practical interest since it produces the 4, 4΄-diisopropylbiphenyl (4, 4΄-DIPB) [1].  4, 4΄-DIPB is a promising precursors for biphenyl-4, 4΄-dicarboxylic acid, which is an intermediate for polyester fibers, engineering plastics, and liquid crystalline polymers for electronic and mechanical devices and films with high heat resistance and strength [2]. Selective synthesis of 4, 4΄-DIPB is not possible on traditional Friedel–Crafts [3], since catalysts such as Lewis acids or silica/alumina [4] are generally produce products large amount of undesired products with low para-selectivity. In contrast, zeolites, being micro porous and crystalline, may be shape-selectively and yield the less bulky para-isomers.

The present work aims to study the influence of zeolite structure for alkylation of biphenyl with propylene over various zeolites such as HY, HZSM-5, HMOR-40 and amorphous SiO2-Al2O3 in a stirred tank reactor. Biphenyl conversion was found to be increased with reaction time for HZSM-5 and HMOR-40 zeolites, whereas for HY and amorphous SiO2-Al2O3 catalysts conversion increased up to certain time and then reached a steady state conversion. The selectivities for 4, 4ʹ-DIPB for HY, HZSM-5 and amorphous SiO2-Al2O3 was in the range of 10-35%: they are much lower than that of HMOR-40. These differences in selectivity might be due to the zeolite structure, pore channel and SiO2/Al2O3 ratio. HMOR-40 was found to be an active catalyst in the alkylation of biphenyl with propylene. The selectivity for 4-isopropylbiphenyl (4-IPBP) and (4, 4ʹ-DIPB) was high among IPB and DIPB isomers, respectively, indicating HMOR-40 shows shape-selective catalysis.

References:

  1. Y. Sugi, X.-L. Tu, T. Matsuzaki, T. Hanaoka, Y. Kubota, J.H. Kim, M. Matsumoto, K. Nakajima, A. Igarashi, Catal. Today 31 (1996) 3.
  2. J.D. Fellman, R.J. Saxton, P.R. Weatrock, E.G. Derouane, P. Massini, US Patent 5,026,942 (1991).
  3. D.B. Priddy, Ind. Eng. Chem. Prod. Res. Dev. 8 (1969) 239.
  4. T. Matsuda, E. Kikuchi, Res. Chem. Interm. 19 (1993) 319.

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