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Synthesis and hydrolysis of chemodegradable cationic surfactants containing the 1,3‐dioxolane moiety
Author(s) -
Wilk Kazimiera A.,
Bieniecki Albert,
Burczyk Bogdan,
Sokolowski Adam
Publication year - 1994
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02541476
Subject(s) - chemistry , bromide , reactivity (psychology) , hydrolysis , dimethylamine , medicinal chemistry , moiety , alkyl , reaction rate constant , organic chemistry , kinetics , medicine , physics , alternative medicine , pathology , quantum mechanics
In acid‐catalyzed reactions of long‐chain aliphatic aldehydes (Ia‐d where a = n ‐C 7 H 15 ; b = n ‐C 9 H 19 ; c = n ‐C 11 H 23 ; d= n ‐C 13 H 27 ), 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 [(2,2‐dihexyl‐1,3‐dioxolan‐4‐yl)methyl] 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 nuclear magnetic resonance spectroscopy. Additionally, [(2‐methyl‐1,3‐dioxolan‐4‐yl)methyl] trimethylammonium bromide and [(2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)‐methyl] 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°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.