Collect. Czech. Chem. Commun.
1997, 62, 1342-1354
https://doi.org/10.1135/cccc19971342
Metallomicellar Hydrolytic Catalysts Containing Ligand Surfactants Derived from Alkyl Pyridin-2-yl Ketoxime
Radek Cibulka, David Dvořák, František Hampl and František Liška
Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
Abstract
N-Hexyl- (2a), N-octyl- (2b), N-decyl- (2c) and N-dodecyl-N-[2-(hydroxyimino)-2-(pyridin-2-yl)ethyl]dimethylammonium (2d) nitrates were synthesized as water-soluble cationic ligand surfactants. Three types of micellar catalytic systems employing salts 2 were prepared: homomicellar water solutions of salts 2, comicellar solutions of salts 2 with an inert cationic tenside hexadecyltrimethylammonium bromide (CTAB) and comicellar systems consisting of complexes of ligand surfactants 2 with transition metal ions (Co(II), Ni(II), Cu(II) and Zn(II)) and CTAB. Hydrolytic efficiency of all micellar and metallomicellar systems was tested by measuring the kinetics of the model substrate cleavage under pseudo-first-order reaction conditions. Of the above-mentioned catalysts, comicellar systems of salts 2 comicellized with CTAB were most efficient. In all cases, with the exception of Zn(II), coordination of a metal ion decreased the hydrolytic efficiency of salts 2.
Keywords: Ester hydrolysis; Ligand surfactant; Micellar catalysis; Pyridine derivatives.
