Abstract
ABSTRACT The epoxide ring opening reaction (ROR) can be considered the
most important side reaction occurring in the epoxidation of soybean oil
reaction network. This reaction consistently reduces the selectivity to
epoxidized soybean oil (ESBO). In this work, this reaction has been
studied in different operative conditions to evaluate the effect on ROR
rate of respectively: (i) the Bronsted acidity of the mineral acid
(H2SO4 or H3PO4), used as catalyst for promoting the oxidation with
hydrogen peroxide of formic to performic acid, that is, the reactant in
the epoxide formation; (ii) the concentration of the nucleophilic
agents, normally present during the ESBO synthesis like HCOOH, HCOOOH,
H2O, H2O2; (iii) the stirring rate that changes the oil-water interface
area; (iv) the adopted temperature. Many different kinetic runs have
been made, in different operative conditions, starting from an already
epoxidized soybean oil. On the basis of these runs two different
reaction mechanisms have been hypothesized, one promoted by the Bronsted
acidity mainly occurring at the oil-water interface and one promoted by
the nucleophilic agents, in particular by formic acid. As it will be
seen, the kinetic laws corresponding to the two mentioned mechanisms are
quite different and this explain the divergent data reported in the
literature on this subject. All the kinetic runs have been correctly
interpreted with a new developed biphasic kinetic model.