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Liquid phase bromination of aromatics over zeolite H-beta catalyst

1999; Elsevier BV; Volume: 150; Issue: 1-2 Linguagem: Inglês

10.1016/s1381-1169(99)00206-x

1873-314X

A.P. Singh, S.P. Mirajkar, S. Sharma,

Environmental remediation with nanomaterials

The liquid phase bromination of chlorobenzene, toluene and xylenes (o-, m-, p-) is catalyzed using zeolite as catalyst and N-bromosuccinimide (NBS) as the brominating agent. In addition, the bromination of toluene has been investigated over various zeolites using both NBS and liquid Br2 as brominating agents. A comparison under similar reaction conditions with H2SO4, in the absence of catalyst and FeCl3 (in the case of toluene) is also investigated for each reaction. Zeolite H-beta is found to be selective compared to the conventional catalysts and other zeolites in the bromination of chlorobenzene and toluene whereas selectivity for 4-bromo-o-xylene (4-BOX/3-BOX) over H-beta and H2SO4 was found nearly comparable in the bromination of o-xylene. In the bromination of toluene, acidic H-beta favours the formation of nuclear products whereas in the absence of any catalyst, in the presence of weakly acidic H–Y and potassium exchanged zeolites K-beta and K–L, the concentration of side-chain product, œ-bromotoluene, is enhanced. The conversion of NBS, rate of NBS conversion (mmol g−1 h−1) and selectivity for products are strongly influenced by the reaction parameters. As the reaction time, catalyst amount, reaction temperature and molar ratios of NBS/toluene are increased, an increase in the conversion of NBS is noticed. Presumably, the catalytic bromination of aromatics proceeds by an electrophile (Br+) which is generated by the heterolytic cleavage of NBS/Br2 by an acidic zeolite. Thus, the generated Br+ attacks the aromatic ring resulting in the formation of brominated nuclear products.