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Continuous Flow Synthesis of Methanofullerenes in Microstructured Reactors: A Kinetic Study
Author(s) -
Silvestrini Simone,
Dalle Nogare Daniela,
Carofiglio Tommaso,
Menna Enzo,
Canu Paolo,
Maggini Michele
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100993
Subject(s) - chemistry , diethyl malonate , selectivity , flow chemistry , cyclopropanation , kinetics , continuous flow , reaction rate constant , volumetric flow rate , malonate , kinetic energy , fullerene , analytical chemistry (journal) , organic chemistry , thermodynamics , catalysis , mechanics , physics , quantum mechanics
The kinetics of the cyclopropanation reaction of diethyl malonate with [60]fullerene were assayed to optimize the continuous flow synthesis of the methanofullerene monoadduct. Experiments were carried out under both batch and flow conditions, by sampling the reaction mixture at different times and separating the components by means of HPLC in a way that resembles a stop/quenched flow system with the addition of a chromatographic step before analysis. The observed concentration profiles of the fullerene species in the reaction mixture were used to calculate the pertinent rate constants and to optimize the selectivity towards the monoaddition product.