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Solid Acid Catalysts for Coumarin Synthesis by the Pechmann Reaction: MOFs versus Zeolites
Author(s) -
Opanasenko Maksym,
Shamzhy Mariya,
Čejka Jiří
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200232
Subject(s) - resorcinol , pyrogallol , chemistry , catalysis , coumarin , benzene , phenols , naphthalene , organic chemistry , ethyl acetoacetate
The catalytic behavior of metal–organic frameworks Cu‐benzene‐1,3,5‐tricarboxylate (CuBTC) and Fe‐benzene‐1,3,5‐tricarboxylate (FeBTC) was investigated in the Pechmann condensation of different phenols (resorcinol, pyrogallol, and naphthol) with ethyl acetoacetate and compared with large‐pore zeolites beta (BEA) and ultrastable Y (USY). Zeolites BEA and USY exhibited high activity in transformations of the most active substrates (resorcinol and pyrogallol) but a low conversion of naphthol was observed. Almost total transformation of naphthol (94–98 % conversion) to the target product was achieved within 24 h of the reaction time over CuBTC and FeBTC. We assume that the regularity in the arrangement of active sites within the framework of CuBTC, which results in the existence of 2 active centers in close proximity, is of critical importance to the transformation of naphthol in the Pechmann reaction that leads to coumarin.