The isopropylation of biphenyl over H-mordenite: roles of 3- and 4-isopropylbiphenyls

Anand, Chokkalingam, Sugimura, Tomonori, Komura, Kenichi, Kubota, Yoshihiro, Kim, Jong-Ho, Seo, Gon, Vinu, Ajayan and Sugi, Yoshihiro (2013) The isopropylation of biphenyl over H-mordenite: roles of 3- and 4-isopropylbiphenyls. Korean Journal of Chemical Engineering, 30 5: 1043-1050. doi:10.1007/s11814-013-0011-1

Author Anand, Chokkalingam
Sugimura, Tomonori
Komura, Kenichi
Kubota, Yoshihiro
Kim, Jong-Ho
Seo, Gon
Vinu, Ajayan
Sugi, Yoshihiro
Title The isopropylation of biphenyl over H-mordenite: roles of 3- and 4-isopropylbiphenyls
Formatted title
The isopropylation of biphenyl over H-mordenite — roles of 3- and 4-isopropylbiphenyls
Journal name Korean Journal of Chemical Engineering   Check publisher's open access policy
ISSN 0256-1115
Publication date 2013-05
Sub-type Article (original research)
DOI 10.1007/s11814-013-0011-1
Volume 30
Issue 5
Start page 1043
End page 1050
Total pages 8
Place of publication United States
Publisher Springer New York
Collection year 2014
Language eng
Formatted abstract
The isopropylation of biphenyl (BP) and 3- and 4-isopropylbiphenyls (3- and 4-IPBPs) was examined over H-mordenites (MOR) to elucidate the mechanism of shape-selective formation of 4,4′-diisopropylbiphenyl (4,4′-DIPB). The isopropylation of BP occurred predominantly to form 4-isopropylbiphenyl (4-IPBP) from BP and 4,4′-DIPB from 4-IPBP. However, 3-IPBP, a minor isomer from BP, cannot participate effectively in the formation of 3,4′-DIPB due to steric restriction of its isopropyl moiety with MOR channels. Selective formation of 4,4′-DIPB was observed at low to moderate temperatures: 225–275 °C. However, the selectivities for 4,4′-DIPB were decreased at high temperatures, 300–350 °C under propene pressure, 0.8MPa, by the isomerization of 4,4′-DIPB at external acid sites. The isomerization of 4,4′-DIPB occurred under low propene pressure even at 250 °C. The roles of 3- and 4-IPBPs in the formation of DIPB isomers were examined in the isopropylation of their mixtures. 4-IPBP was consumed much faster than 3-IPBP in all cases examined. 4-IPBP was an exclusive precursor to DIPB isomers, particularly 4,4′-DIPB. 4,4′-DIPB was also found as a predominant isomer in encapsulated products at all conditions examined. These results show that 4-IPBP can preferentially establish active transition state with propene and acid site in MOR channels, resulting in selective formation of 4,4′-DIPB. It is concluded that the isopropylation of BP over MOR occurs through reactant selectivity mechanism and restricted transition state mechanism, but not through product selectivity mechanism.
Keyword MOR
4,4 '-diisopropylbiphenyl
4-and 3-sopropylbiphenyls
Shape-selective Catalysis
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes This article is dedicated to Prof. Gon Seo on the occasion of his retirement from Chonnam National University.

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
Australian Institute for Bioengineering and Nanotechnology Publications
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