vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/achb.1025QCZKPNvuzbiochemi-1632Research ArticleХИМИЧЕСКИЕ НАУКИCHEMICAL SCIENCESПолучение, реакции и применение солей глицидилтриметиламмония (обзор)Preparation, reactions, and application of glycidyltrimethylammonium salts: a reviewhttps://orcid.org/0000-0002-0639-0455СоковС. А.SokovS. A.

Соков Сергей Александрович, к.х.н., младший научный сотрудник

450064, г. Уфа, ул. Космонавтов, 1

Sergey A. Sokov, Cand. Sci. (Chemistry), Junior Researcher

1, Kosmonavtov St., Ufa, 450064

s.a.sokov.tltsu@gmail.comhttps://orcid.org/0000-0002-8592-3984ГоловановА. А.GolovanovA. A.

Голованов Александр Александрович, д.х.н., главный научный сотрудник

450064, г. Уфа, ул. Космонавтов, 1

Alexander A. Golovanov, Dr. Sci. (Chemistry), Chief Researcher

1, Kosmonavtov St., Ufa, 450064

aleksandgolovanov@yandex.ruhttps://orcid.org/0000-0001-6452-9454БорисоваЮ. Г.BorisovaYu. G.

Борисова Юлианна Геннадьевна, к.х.н., доцент

450064, г. Уфа, ул. Космонавтов, 1

Yulianna G. Borisova, Cand. Sci. (Chemistry), Associate Professor

1, Kosmonavtov St., Ufa, 450064

yulianna_borisova@mail.ruhttps://orcid.org/0000-0001-9770-5434РаскильдинаГ. З.RaskildinaG. Z.

Раскильдина Гульнара Зинуровна, д.х.н., профессор

450064, г. Уфа, ул. Космонавтов, 1

Gulnara Z. Raskildina, Dr. Sci. (Chemistry), Professor

1, Kosmonavtov St., Ufa, 450064

graskildina444@mail.ruhttps://orcid.org/0000-0001-6719-2359СултановаР. М.SultanovaR. M.

Султанова Римма Марсельевна, д.х.н., профессор

450064, г. Уфа, ул. Космонавтов, 1

Rimma M. Sultanova, Dr. Sci. (Chemistry), Professor

1, Kosmonavtov St., Ufa, 450064

rimmams@yandex.ruhttps://orcid.org/0000-0001-6365-5010ЗлотскийС. А.ZlotskyS. S.

Злотский Семен Соломонович, д.х.н., профессор, заведующий кафедрой

450064, г. Уфа, ул. Космонавтов, 1

Semon S. Zlotsky, Dr. Sci. (Chemistry), Professor, Head of the Department

1, Kosmonavtov St., Ufa, 450064

nocturne@mail.ruУфимский государственный нефтяной технический университетРоссияUfa State Petroleum Technological UniversityRussian Federation202602042026161615Copyright © Соков С.А., Голованов А.А., Борисова Ю.Г., Раскильдина Г.З., Султанова Р.М., Злотский С.А., 20262026Соков С.А., Голованов А.А., Борисова Ю.Г., Раскильдина Г.З., Султанова Р.М., Злотский С.А.Sokov S.A., Golovanov A.A., Borisova Y.G., Raskildina G.Z., Sultanova R.M., Zlotsky S.S.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vuzbiochemi.elpub.ru/jour/article/view/1632

Настоящий обзор ставит целью систематизацию и анализ научных данных, опубликованных за последние 50 лет, касающихся методов синтеза, химических превращений и практического применения солей глицидилтриметиламмония, которые являются перспективными катионными поверхностно-активными веществами. В статье детально рассмотрены два основных способа получения солей глицидилтриметиламмония: реакция триметиламина с эпихлоргидрином или эпибромгидрином и обработка 3-хлоро-2-гидроксипропилтриметиламмония щелочью. Наиболее распространенным является первый метод, обеспечивающий высокие выход и чистоту продукта, но требующий низких температур для минимизации побочных процессов. Основное внимание уделено реакционной способности эпоксидного цикла, который легко раскрывается под действием различных нуклеофилов: спиртов, карбоновых кислот, тиолов и аминов. Это позволяет синтезировать широкий спектр функционализированных соединений, в частности сложные эфиры с жирными кислотами, модифицированные углеводы (крахмал, целлюлозу) и другие производные. Продукты на основе солей глицидилтриметиламмония находят широкое применение благодаря введению катионного фрагмента, придающего поверхностно-активные свойства. Они добавляются в качестве эффективных компонентов в моющие средствах и косметику, применяются для создания антимикробных покрытий за счет координации наночастиц металлов, а также используются в нефтехимической отрасли в качестве экологичных стабилизаторов буровых растворов. Таким образом, соли глицидилтриметиламмония представляют собой универсальные и высокореакционноспособные промежуточные соединения для получения функциональных материалов в различных отраслях промышленности.

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.

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The authors declare that there are no conflicts of interest present.