DEVELOPMENT OF TECHNOLOGY FOR THE PRODUCTION OF 4,4'-DIPROPARGYL DIETHER AZOPHENOL

РАЗРАБОТКА ТЕХНОЛОГИИ ПОЛУЧЕНИЯ 4,4' - ДИПРОПАРГИЛОВОГО ДИЭФИРА АЗОФЕНОЛА
Цитировать:
Ismailov B., Makhsumov A., Azamatov U. DEVELOPMENT OF TECHNOLOGY FOR THE PRODUCTION OF 4,4'-DIPROPARGYL DIETHER AZOPHENOL // Universum: технические науки : электрон. научн. журн. 2022. 1(94). URL: https://7universum.com/ru/tech/archive/item/12946 (дата обращения: 24.05.2024).
Прочитать статью:
DOI - 10.32743/UniTech.2022.94.1.12946

 

ABSTRACT

This article discusses a new technology for obtaining 4,4' - dipropargyl diether of azophenol and studies its physico-chemical parameters.

АННОТАЦИЯ

В данной статье рассматривается новая технология получения 4,4' - дипропаргилового диэфира азофенола и изучаются его физико-химические параметры.

 

Keywords: 4,4' - dipropargyl diether azophenol, technology, physico-chemical parameters, elemental analysis.

Ключевые слова: 4,4' - дипропаргиловый диэфир азофенола, технология, физико-химические параметры, элементный анализ.

 

The global demand for azo dyes is growing day by day. In order to expand the range of dyes used in almost all sectors of the national economy, primarily in chemical, agriculture, engineering, as well as in pharmacy and medicine, azonaphthol and azophenol derivatives are used. They are considered an important component for coloring synthetic, natural fibers, plastics, paper, film, leather wood materials and many other items [1-2, 9].

The presence of nitrogen atoms in the molecules of azophenol compounds, triple (-C≡C-H) bonds, increases physiological, pharmacological, biological activity, simultaneously reducing toxicity, and also exhibits antimicrobial, anti-ulcer, antifungal, antiviral and many other properties [4, 7].

Currently, they are necessary for dyeing natural and synthetic fibers, plastics, paper, and much more [5-6].

Therefore, the synthesis and development of a new technology for producing azo dye is an urgent task today.

The literature describes [3] the synthesis of various -N-S-acetylenic compounds with a terminal triple bond. However, we have not found information on the synthesis of dipropargyl compounds of azophenol; these little-known compounds are essentially a new type of compounds, the properties of which have not been studied. In this regard, we obtained derivatives of 4,4'-dipropargyl diether of azophenol by interaction with propargyl halide in the presence of an organic solvent acetone, potash and 4,4'-azobis(phenol) according to the following scheme:

The physico-chemical parameters of 4,4 '- dipropargyl diether of azophenol (I) are given in table.

Table

Physico-chemical parameters of 4,4 '- dipropargyl diether of azophenol (I)

Structural formula

Output, %

Melting temperature, 0С

Rf

Gross formula

MM

Elemental analysis, %

Calculated

Found

N

N

93,1

195-196

0,69

C18H14N2O2

290,32

9,64

9,49

 

Purification of 4,4' - dipropargyl ether of azo phenol was carried out using preparative thin - layer chromatography on  in the benzene:methanol=5:1 system.

Technology for the production of 4,4'-dipropargyl diether azophenol (I)

The technological process of obtaining 4,4' - dipropargyl diether of azophenol as a dye for polyethylene is carried out in the following way. 4,4'-azobis(phenol) and potash, freshly distilled propargyl bromide, acetone are placed in a reactor 6 equipped with a stirrer, condenser and separator, and the mixture is heated to a boil for 1 hour while stirring. The reaction mixture is kept at 90-100 0С for another 8 hours. After cooling, the reaction mixture is filtered and the resulting mixture is dried in a dryer, after evaporation of the solvent, the mass is put into a crusher and crystals are collected. (fig. 1)

 

Figure 1. Basic technological scheme for the production of 4,4' - dipropargyl diether of azophenol:

1-container for 4,4'-azobis(phenol); 2-container for propargyl halide; 3-container for acetone; 4-container for potash; 5-dispensers; 6-reactor; 7- condenser ; 8-separator; 9-container for filter; 10-container for waste; 11-dryer; 12-crusher; 13-container for finished product.

 

Thus, the resulting preparation [8] 4,4' - dipropargyl diether azophenol is recommended for use in the production of enamels and other paint and varnish materials intended for painting metal, wood and other indoor surfaces, as well as surfaces exposed to atmospheric exposure.

Conclusion

In conclusion, based on the studied research results, an effective technology for the production of 4,4' - dipropargyl diether of azophenol was developed and used as a dye for coloring high-density polyethylene at LLC Shurtan Gas Chemical Complex in Kashkadarya region of the Republic of Uzbekistan.

 

References:

  1. Alain Bekaert, Olivier Provot, Olimihamina Rasolojaona, Moua d Alami and Jean-Daniel Brion. N-Methylpyrrolidin-2-one hydrotribromide (MPHT) a mild reagent for selective bromination of carbonyl compounds: synthesis of substituted 2-bromo-1-naphtols // Tetrahedron Letters 46 (2005). – PP. 4187–4191.
  2. Michael J. S. Dewar, Tadao Nakaya. Oxidative Coupling of Phenols // J. Am. Chem. Soc. 1968, 90, 25, 7134–7135. https://doi.org/10.1021/ja01027a051
  3. Махсумов А.Г., Исмаилов Б.М., Абсалямова Г.М., Мирзаахмедова М.А. Ацетиленовые изотиоцианаты: синтез, свойства и их биологическая активность// Узбекский химический журнал. Ташкент-2019. -№6. - С.59-70.
  4. Махсумов А.Г., Хайдарова З.Г., Сулаймонов Б.И., Ибрагимов А.А. Разработка технологии получения нового производного бис–карбамата азокрасителя и его внедрение // Химический журнал Казахстана. –Алматы, 2007, Вып 16, –C.75-77.
  5. Махсумов А.Г., Исмаилов Б.М. Синтезы на основе 2,21-дипропаргилового диэфира азобензола, строение и его красящие свойства // Ж.: «Узбекского журнала нефти и газа» научно-технический журнал, Ташкент- 2020 г., №2 – С.72-77.
  6. B. Ismailov, A. Makhsumov, N. Valeeva - Synthesis of derivative pyrazols based on 2,21-diproparghyl ether azobenzene, structure and its coloring properties // “Proceedings of the International conference on integrated innovative development of Zarafshan region: Achievements, challenges and prospects” // Navoi-2019 y., 27-28 November. - PP.361-366.
  7. Makhsumov A.G., Valeeva N.G., Nabiev U.A., Ismailov B.M. Synthesis of new bromine acetylene dithiocarbamates derivatives and their growth-stimulating activity // http://www.jcreview.com/?mno=93870. J.: Journal of Critical Reviews, ISSN-2394-5125, Vol 7, Issue 4, 2020- PP.113-119.
  8. Махсумов А.Г., Исмаилов Б.М. Синтезы на основе 4,4’-дипропаргилового диэфира азобензола, строение и их свойства // Ж. Life Sciences and Agriculture электронный научно-практический журнал ISSN:2181-0761, DOI: 10.24411/2181-  0761/2020-10038. Выпуск: №2.2-2020.-С.15-19.
  9. Захариев, А.И., Иванова, В.В., Хидекель, М.Л. et al. Гидрирование ароматических нитросоединений в присутствии комплекса платины (II) C 1-Фенил-азо-2-нафтолом в диметилформамиде. React Kinet Catal Lett 8, 195–201 (1978). https://doi.org/10.1007/BF02061305.
Информация об авторах

Doctoral student of the department of Chemical technology of oil and gas refining, Tashkent chemical-technological Institute, Uzbekistan, Tashkent

докторант кафедры «Химическая технология переработки нефти и газа» Ташкентского химико-технологического института, Республика Узбекистан, г. Ташкент

Doctor of Chemical Sciences, professor of the department of Chemical technology of oil and gas refining, Tashkent chemical-technological Institute,  Uzbekistan, Tashkent

д-р хим. наук, проф., Ташкентский химико-технологический институт, кафедра “Химическая технология переработки нефти и газа”, Республика Узбекистан, г. Ташкент

Senior teacher of the department of Chemical technology of oil and gas refining, Tashkent chemical-technological Institute, Uzbekistan, Tashkent

старший преподаватель кафедры Химической технологии переработки нефти и газа Ташкентского химико-технологического института, Узбекистан, г. Ташкент

Журнал зарегистрирован Федеральной службой по надзору в сфере связи, информационных технологий и массовых коммуникаций (Роскомнадзор), регистрационный номер ЭЛ №ФС77-54434 от 17.06.2013
Учредитель журнала - ООО «МЦНО»
Главный редактор - Ахметов Сайранбек Махсутович.
Top