Supramolecular Catalysts for the Radical Destruction of Hydroperoxides Based on Choline Derivatives

The effect of natural quaternary ammonium compounds (QAC) of choline (Ch) and its derivatives, acetylcholine (AСh) and L-carnitine (LCh), containing the tetraalkylammonium cation (CH 3 ) 3 RN + , on the radical decomposition of hydroperoxides (ROOH) was studied. In mixtures of ACh and Ch with ROOH i...

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Bibliographic Details
Published in:Kinetics and catalysis 2023-02, Vol.64 (1), p.67-73
Main Authors: Potapova, N. V., Kasaikina, O. T., Berezin, M. P., Plashchina, I. G., Gulin, A. A.
Format: Article
Language:English
Subjects:
Ammonium compounds
Carnitine
Catalysis
Cations
Cellulose
Chemistry
Chemistry and Materials Science
Chlorobenzene
Choline
Crystalline cellulose
Decomposition
Phosphatidylcholine
Physical Chemistry
Polymerization
Quaternary ammonium salts
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Summary:The effect of natural quaternary ammonium compounds (QAC) of choline (Ch) and its derivatives, acetylcholine (AСh) and L-carnitine (LCh), containing the tetraalkylammonium cation (CH 3 ) 3 RN + , on the radical decomposition of hydroperoxides (ROOH) was studied. In mixtures of ACh and Ch with ROOH in chlorobenzene, mixed nanoaggregates are formed, and accelerated decomposition of ROOH into radicals occurs; the rates of radical formation measured by the inhibitor method decrease in the series ACh > Ch LCh. ACh and Ch immobilized on microcrystalline cellulose retain the ability to catalyze the radical decomposition of ROOH and initiate the polymerization of styrene containing ROOH from the surface. LСh adsorbed on cellulose does not affect the decomposition of ROOH and the rate of polymerization. Scanning electron microscopy (SEM) showed that ACh and Ch adsorbed on a silicon plate accelerate the radical decomposition of ROOH and initiate oxidative condensation of egg phosphatidylcholine on the surface of the plate, while adsorbed LCh does not affect the decomposition of ROOH. LCh, unlike ACh and Ch, is an internal salt in which the R 4 N + cation is neutralized by its own carboxy anion, i.e., LCh has no external counterion and, probably, for this reason, it differs from ACh and Ch in the mechanism of adsorption and interaction with ROOH.
ISSN:0023-1584
1608-3210
DOI:10.1134/S0023158423010056