Preparation, reactions, and application of glycidyltrimethylammonium salts: a review

The present review aims to generalize and analyze the scientific data published over the past 50 years about the methods of synthesis, chemical transformations, and practical application of glycidyltrimethylammonium salts, which are promising cationic surfactants. The article discusses in detail the two main methods for the preparation of glycidyltrimethylammonium salts: reaction of trimethylamine with epichlorohydrin or epibromohydrin and treatment of 3-chloro-2-hydroxypropyl trimethylammonium with alkali. Although the most common first method provides the high yield and purity of the product, low temperatures are required for minimizing side processes. The main attention is paid to the reactivity of the epoxy cycle, which is easily revealed by the action of various nucleophiles: alcohols, carboxylic acids, thiols, and amines. Thus, a wide range of functionalized compounds can be synthesized, in particular esters with fatty acids, modified carbohydrates (starch, cellulose), and other derivatives. Products based on glycidyltrimethylammonium salts find a wide utility due to the introduction of a cationic fragment that imparts surfactant properties. These products are used as coordinators of metal nanoparticles in antimicrobial coatings, effective components in detergents and cosmetics, as well as environmentally friendly stabilizers of drilling fluids in the petrochemical industry. Thus, glycidyltrimethylammonium salts are versatile, high-reactive intermediates for the production of functional materials in various industries.