PHASE-EQUILIBRIA WITH SUPERCRITICAL CARBON-DIOXIDE FOR THE ENZYMATIC PRODUCTION OF AN ENANTIOPURE PYRETHROID COMPONENT .2. TERNARY AND 5-COMPONENT SYSTEMS
Aa. Chrisochoou et al., PHASE-EQUILIBRIA WITH SUPERCRITICAL CARBON-DIOXIDE FOR THE ENZYMATIC PRODUCTION OF AN ENANTIOPURE PYRETHROID COMPONENT .2. TERNARY AND 5-COMPONENT SYSTEMS, Journal of chemical and engineering data, 42(3), 1997, pp. 558-561
(S)-alpha-Cyano-m-phenoxybenzyl alcohol is an important synthon for py
rethroid insecticides. It is obtained by the lipase-catalyzed kinetic
resolution of racemic alpha-cyano-m-phenoxybenzyl acetate, with 1-octa
nol acting as an acyl acceptor and thus being converted to 1-octyl ace
tate. Supercritical carbon dioxide is used as a unique solvent for the
reaction and the subsequent product recovery by extraction. Phase equ
ilibria of the ternary systems CO2 + alpha-cyano-m-phenoxybenzyl alcoh
ol + alpha-cyano-m-phenoxybenzyl acetate and CO2 + 1-octanol + 1-octyl
acetate were measured at 313.15 K and at respective pressures of 20 M
Pa and 8 MPa. The latter ternary exhibits alyotropic behavior. Phase e
quilibria of the ternary CO2 + 1-octanol + alpha-cyano-m-phenoxybenzyl
acetate and the five-component system CO2 + 1-octanol + 1-octyl aceta
te + alpha-cyano-m-phenoxybenzyl alcohol + alpha-cyano-m-phenoxybenzyl
acetate were determined at 313.15 K and at various pressures of up to
17 MPa. The Soave-Redlich-Kwong equation of state with the mixing rul
es due to Huron and Vidal was checked for its ability to reproduce the
measured equilibrium data. Whereas model predictions match experiment
al data of the ternary systems within the estimated accuracy of the me
asurements, larger deviations exist for the five-component systems.