5421-12-5Relevant articles and documents
Synthesis and Hydrolysis of Chemodegradable Cationic Surfactants Containing the 1,3-Dioxolane Moiety
Wilk, Kazimiera A.,Bieniecki, Albert,Burczyk, Bogdan,Sokolowski, Adam
, p. 81 - 85 (2007/10/02)
In acid-catalyzed reactions of long-chain aliphatic aldehydes (Ia-d where a = n-C7H15; b = n-C9H19; c = n-C11H23; d = n-C13H27), and tridecan-7-on (Ie) with 3-chloro-1,2-propane-diol, 2-alkyl- and 2,2-dihexyl-4-chloromethyl-1,3-dioxolanes (IIa-e) were obtained.They were reacted with anhydrous dimethylamine to obtain, respectively, 2-alkyl- and dimethylamines (IIIa-e), which were quaternized with methyl bromide to obtain the desired ammonium bromides (IVa-e).The structure and purity of the compounds was proved by mass spectrometry and proton magnetic resonance spectroscopy.Additionally, trimethylammonium bromide and trimethylammonium bromide were synthesized as nonaggregating standards.Hydrolysis reactions of the synthesized ammonium bromides were performed by 0.1 M hydrochloric acid in 1:1 (vol/vol) 1,4-dioxane-water mixtures at 50, 60 and 70 deg C.Rate constants of hydrolysis reactions were determined by observing carbonyl group formation at 280 nm.The hydrolytic reactivity of the studied surfactants (IVa-c,e) was determined under unaggregated conditions.Compound IVd showed decreased reactivity.The length of the 2-alkyl group has a minor effect on rate constant values.The influence of various substituents at the C-4 atom of the 2-nonyl-1,3-dioxolan-4-yl derivatives on rate constants was also investigated. KKEY WORDS: trimethylammonium bromides, trimethylammonium bromide, chemodegradable acetal-type cationic surfactants, kinetic and thermodynamic parameters of 1,3-dioxolane ring hydrolysis.
