vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/2227-2925-2020-10-4-556-563vuzbiochemi-470Research ArticleХИМИЧЕСКИЕ НАУКИCHEMICAL SCIENCESСинтез и использование 10-гидрокси-3,3,6,6-тетраметил-9-(4-гидрокси-3-метоксифенил)-1,2,3,4,5,6,7,8,9,10-декагидроакридин-1,8-диона в качестве индикатора кислотно-основного титрованияSynthesis and using of 10-hydroxy-3,3,6,6-tetramethyl-9-(4-hydroxy-3-methoxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dion as acid base titration indicatorПыркоА. Н.PyrkoA. N.

Пырко Анатолий Николаевич - кандидат химических наук, доцент кафедры экологической химии и биохимии.

220070, Минск, ул. Долгобродская, 23/1

Anatoliyi N. Pyrko - Cand. Sci. (Chemistry). Associate Professor, Environmental Chemistry and Biochemistry Department.

23, Dolgobrodskaya St., Minsk, 220070

pyrko@yandex.ruМеждународный государственный экологический институт им. А.Д. Сахарова, Белорусский государственный университетБеларусьInternational Sakharov Environmental Institute of Belarusian State UniversityBelarus202007012021104556563Copyright © Пырко А.Н., 20212021Пырко А.Н.Pyrko A.N.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/470

Целью данной работы являлся синтез нового производного 10-гидроксидекагидроакридин-1,8-диона, определение структуры и изучение возможности использования этого соединения в качестве индикатора кислотно-основного титрования. Синтез 10-гидрокси-3,3,6,6-тетраметил-9-(4-гидрокси-3-метоксифенил)-1,2,3,4,5,6,7,8,9,10-декагидроакридин-1,8-диона осуществлен с учетом принципов «зеленой химии» взаимодействием димедона, гидроксиламина и 4-гидрокси-3-метокси-бензойного альдегида в экологически безопасном водно-спиртовом или водном растворе. В качестве катализатора использовалась лимонная кислота либо додецил сульфат натрия соответственно. Очистку синтезированного соединения осуществляли кристаллизацией из этанола. Полученное соединение характеризовали с помощью спектров 1Н ЯМР, 13С ЯМР, поглощения и флуоресценции в УФ-видимой области. В водно-спиртовом растворе гидроксидекагидроакридиндиона наблюдается поглощение фиолетового света, максимум полосы поглощения которого смещается в область голубого света при добавлении к раствору щелочи. При облучении этанольного раствора УФ-излучением возникает двухполосная флуоресценция в видимой области. Одна полоса исчезает при добавлении основания в раствор. Структура полученного соединения подтверждена масс-спектрометрическим анализом высокого разрешения. В масс-спектре 10-гидрокси-3,3,6,6-тетра-метил-9-(4-гидрокси-3-метоксифенил)-1,2,3,4,5,6,7,8,9,10-декагидроакридин-1,8-диона имеется пик иона [M+1]+. Пик основного иона соответствует трициклическому фрагменту элиминирования ароматического цикла молекулярного иона. Это вещество бесцветно в кислых и нейтральных растворах, а в основных имеет розовый цвет. Кислотную константу диссоциации этого соединения в водно-спиртовом растворе определяли спектрофотометрическим методом в УФ-видимой области. Показано, что полученное соединение может быть использовано в качестве индикатора титрования сильных кислот и оснований.

The aim of this work is the synthesis of new 10-hydroxydecahydroacridine-1,8-dione derivative, determination of the structure and to study the possibility of using this compound as an indicator of acid-base titration. Environmentally friendly synthesis of 10-hydroxy-3,3,6,6-tetramethyl-9-(4-hydroxy-3-methoxyphe-nyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dion has been developed by one pot interaction of dimedone, hydroxylamine and 4-hydroxy-3-methoxybenzoic aldehyde in water-alcohol or water solution using citric acid or sodium dodecyl sulfate as catalysts, respectively. Purification of the synthesized compound was carried out by crystallization from ethanol. The obtained compound was characterised by 1H NMR ,13C NMR and UV-Vis spectroscopies. This substance in water-alcohol solution shows intense violet light absorption. Addition alkali induces red shift of absorption maximum to the blue region. UV irradiation of solution of this substance in alcohol induces two-band fluorescence in the visible region. One band disappears upon addition of a base in solution. The structure of the obtained compound was confirmed by high resolution massspectrometry analysis. In the mass-spectrum of 10-hydroxy-3,3,6,6-tetramethyl-9-(4-hydroxy-3-methoxyphe-nyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridin-1,8-dion observed [M+1]+ ion peak. The base peak corresponds to tricyclic fragment due to the elimination aromatic cycle from molecular ion. This substance is colorless in acidic and neutral and pink in base solutions. The acid dissociation constant of this compound in a water-alcohol solution was determined by the UV-Vis spectroscopic technique. It was shown that the obtained compound can be used as an indicator for the titration of strong acids and bases.

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