Open AccessPLANT OIL VALORIZATION BY CROSS-METATHESIS REACTIONS: SYNTHESIS OF FINE CHEMICALS FROM METHYL OLEATE
Author(s) -
Andrés Fernando Trasarti,
E R Gonzalez,
Pablo Daniel Nieres,
C.R. Apesteguı́a
Publication year - 2020
Publication title -
latin american applied research
Language(s) - English
Resource type - Journals
eISSN - 1851-8796
pISSN - 0327-0793
DOI - 10.52292/j.laar.2020.477
Subject(s) - metathesis , catalysis , salt metathesis reaction , chemistry , ethylene , toluene , organic chemistry , yield (engineering) , cinnamaldehyde , methyl oleate , materials science , polymerization , metallurgy , polymer
This work studies the production of high-value compounds by the cross-metathesis of methyl oleate (MO) with ethylene, cinnamonitrile and cinnamaldehyde using the 2nd generation Hoveyda-Grubbs complex (HG) as catalyst, either dissolved in toluene or supported on silica. Reactions were carried out in batch reactors between 313 and 343 K. The yield to cross-metathesis products (YC-M) for the MO cross-metathesis with cinnamonitrile and cinnamaldehyde increased with the initial molar reactant ratio (RCN/MO, RCA/MO), reaching YC-M values of 82% and 95%, respectively, at R = 7. No catalyst deactivation took place during the 400-min catalytic runs. The liquid-phase cross-metathesis of MO with ethylene (ethenolysis) was performed over HG(10%)/SiO2 catalysts, producing 1-decene and methyl 9-decenoate, a valuable intermediate for the synthesis of pheromones. At RC2/MO = 2.5, the selectivity to ethenolysis products was 77% at 82% MO conversion. The MO self-metathesis was the only side reaction observed in all the catalytic tests.