TY - JOUR

T1 - Self-Assembled Quaternary Ammonium-Containing Comb-Like Polyelectrolytes for the Hydrolysis of Organophosphorous Esters

T2 - Effect of Head Groups and Counter-Ions

AU - Pashirova, Tatiana N.

AU - Fetin, Petr A.

AU - Lezov, Alexey A.

AU - Kadnikov, Matvey V.

AU - Valeeva, Farida G.

AU - Burilova, Evgenia A.

AU - Bilibin, Alexander Yu

AU - Zorin, Ivan M.

PY - 2020/8/1

Y1 - 2020/8/1

N2 - The aim of this work was to increase the efficiency of catalytic systems for the hydrolytic cleavage of 4-nitrophenyl esters of phosphonic acids. Quaternary ammonium-containing comb-like polyelectrolytes («polymerized micelles») with ester cleavable fragments and a low aggregation threshold were used as catalysts. The synthesis of poly(11-acryloyloxyundecylammonium) surfactants with different counterions (Br−, NO3−, CH3C6H4SO3−) and head groups was realized by micellar free-radical polymerization. Molecular weight, critical association concentration, particle sizes and solubilization properties toward Orange OT were determined. Self-assemblies organized by poly(11-acryloyloxyundecyltrimethyl ammonium) bromide successfully catalyze the hydrolysis of 4-nitrophenyl butylchloromethylphosphonate up to two orders of magnitude compared to aqueous alkaline hydrolysis. The development of these catalysts is promising for industrial applications and organophosphorus compound detoxification.

AB - The aim of this work was to increase the efficiency of catalytic systems for the hydrolytic cleavage of 4-nitrophenyl esters of phosphonic acids. Quaternary ammonium-containing comb-like polyelectrolytes («polymerized micelles») with ester cleavable fragments and a low aggregation threshold were used as catalysts. The synthesis of poly(11-acryloyloxyundecylammonium) surfactants with different counterions (Br−, NO3−, CH3C6H4SO3−) and head groups was realized by micellar free-radical polymerization. Molecular weight, critical association concentration, particle sizes and solubilization properties toward Orange OT were determined. Self-assemblies organized by poly(11-acryloyloxyundecyltrimethyl ammonium) bromide successfully catalyze the hydrolysis of 4-nitrophenyl butylchloromethylphosphonate up to two orders of magnitude compared to aqueous alkaline hydrolysis. The development of these catalysts is promising for industrial applications and organophosphorus compound detoxification.

KW - hydrolysis

KW - phosphorous acid esters

KW - polyelectrolytes

KW - self-assembly

KW - surfactants

KW - AQUEOUS-SOLUTIONS

KW - CATIONIC SURFACTANTS

KW - SOLUBILIZATION

KW - PYRENE

KW - NANOREACTORS

KW - POLYMERIZED MICELLES

KW - ALKALINE-HYDROLYSIS

KW - FLUORESCENCE

KW - SYSTEMS

KW - AGGREGATION

UR - http://www.scopus.com/inward/record.url?scp=85089968997&partnerID=8YFLogxK

U2 - 10.1002/cplu.202000417

DO - 10.1002/cplu.202000417

M3 - Article

C2 - 32865345

AN - SCOPUS:85089968997

VL - 85

SP - 1939

EP - 1948

JO - ChemPlusChem

JF - ChemPlusChem

SN - 2192-6506

IS - 8

ER -