2012 AIChE Annual Meeting

(683b) Shape-Selective Alkylation of Biphenyl with Propylene by Using Zeolite Catalysts

Author

Sparks, D. E., University of Kentucky


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.
See more of this Session: Catalysis with Microporous and Mesoporous Materials III

See more of this Group/Topical: Catalysis and Reaction Engineering Division