Synthesis of Quaternary Ammonium Salts with Novel Counterions

Abstract

The preparations of quaternary ammonium compounds from various tertiary amines and the (environmentally friendly) alkylation agent dimethyl carbonate were carried out. The effects of reaction temperature, reaction time, material mol ratio and solvent dosage on quaternization were examined, and the optimum reaction conditions were determined. Under the optimum conditions, the conversions of mono-alkyl tertiary amines could attain over 99%, while the conversions of di-alkyl tertiary amines reached over 95%. Moreover, a series of quaternary ammonium salts with new counterions (HCO 3 , CH 3 COO, CH 3 CH 2 COO, CH 3 CH(OH)COO) were synthesized by the hydrolysis of methyl carbonate quaternary ammonium salts or by ion exchange reaction of methyl carbonate quaternary ammonium salts with corresponding acids.

One‐Step Preparation of Tough and Self‐Healing Polyion Complex Hydrogels with Tunable Swelling Behaviors

“…[28] Moreover, the identity of the counter ion was further determined by FT-IR spectroscopy. The strong peak at 1261 cm −1 assigned to the C-O-C stretching of the methyl carbonate ions of the methyl carbonate monomer matched the description in the literature, [29] and the strong peaks at 1406, 1008, 833, 704 cm −1 in the MPTB spectrum indicate the presence of bicarbonate ions. [30] These peaks all disappeared after the addition of an equivalent amount of HCl, which transformed the bicarbonate to chloride ions.…”

Preparation, surface properties, and antibacterial activity of a poly(dimethyl siloxane) network containing a quaternary ammonium salt side chain

“…For all of the samples, the conversion was periodically measured every 2 h. The content of QAS was calculated by a twophase titration analysis, as described in the literature. 32 The quaternization conversion for the three samples reached 95% after 14 h of reaction at 120 C. As shown in Figure 3, we found that the quaternization reaction of the HT-PCPMS-ran-PDMS-4 sample was significantly faster than the others. The reason was that the content of chloropropyl in the polysiloxanes was higher than those in the other two samples, and the higher chance of molecular collisions caused the reaction to be quicker.…”

“…The conversion of the quaternization over time is shown in Figure . For all of the samples, the conversion was periodically measured every 2 h. The content of QAS was calculated by a two‐phase titration analysis, as described in the literature . The quaternization conversion for the three samples reached 95% after 14 h of reaction at 120°C.…”

Synthesis and Properties of Tetradecyltrimethylammonium Carboxylates

“…The effects of reaction temperature, reaction time, material mol ratio, and solvent dosage on quaternization were investigated in the literature. [7] Here, under the optimum quaternization conditions, the tetradecyltrimethylammonium mono-methyl carbonates (TTAMC) were synthesized, and then reacted with different carboxylic acids to prepare the tetradecyltrimethylammonium carboxylates, the detail as follows:…”

“…The quaternary ammonium salts methyl carbonates (QASMC) obtained by the process of tertiary amines and DMC are useful intermediate products, which can react with different acids to prepare QAS with new counterions. [6,7] By this way, many kinds of QAS could be synthesized and these novel QAS possessed special performances. [8] Obviously, the development of various novel QAS and their derivatives seem to be worth more attention.…”