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Section 8. Chemistry
Islamova Yulduz Urolovna, The basic doktorant student of Tashkent Chemical Technological Institute Republic of Uzbekistan, Tashkent E-mail: [email protected] Maksumova Oytura Sitdikovna, doktor of Chemical Sciences, professor, Tashkent Institute of Chemistry and Technology epublic of Uzbekistan, Tashkent Tadjieva SHaxnoza Abduvalievna, senior lecturer of Tashkent Chemical Technological Institute
Republic of Uzbekistan, Tashkent
SYNTHESIS OF N-ACRYLOILOCARBAZOLE AND ITS MODIFICATION TO POLYPROPYLENE
Abstract: Interaction with carbazole and acrylic acid has been studied. Polypropylene modification of synthesized N-acryloylcarbazole has been carried out. The ratio of the initial reagents to the reaction was investigated and the optimum conditions of the reaction were determined. N-acryloylocarbazole and its structure were studied using IR, PMR-spectral analysis.
Keywords: carbazole, acrylic acid, hydroxynone, dimethyl formamide, decalene, N-acryloylcarbazole.
Introduction. Carbazole derivatives, such as polymer in the composition of the initial reagents
heterocyclic compounds, are used as medicaments was influenced by the reaction of Cl and NH group
in medicine, as diodes in electrotechnics, as well as and the yield of production was from 56% to 78%.
raw materials for the production of high molecular In another study, the photosophysical proper-
compounds. Also, carbazole-derived salts increase ties of indolo [3, 2-b] carbazole derivatives were
the activity ofpeptide bonds in the human body, and studied [3, 1629-1635]. Synthesized indolo [3,
carbazole-derivatives polymers serve as charge col- 2-b] carbazole compounds exhibit high levels of
lector in capacitors. Carbazole derivative polyepoxy- photoluminescence property. These obtained data
propylcarbazole polymer is a good conductor so, it allowed to use indolo carbazole compounds to be
is used as a light-emitting layer in photoconductor applied in electrolyumination devices. Indolo [3,
[1, 780-785]. Carbazole derivative homopolycy- 2-b] carbazole was used in transistors as an light
anurate was synthesized by the authors [2, 1731- sensitive electronic material. According to the
1740]. It was observed that the interphase con- data, the modification of polypropylene wastes
densation process goes in two steps based on the with basic chemical compounds was studied at the
Shotten-Bauman reaction. The reaction of the linear temperature of70-90 °C. Here polypropylene and
polyacrylic acid waste were used [4, 227-232]. Car-bazole and acrylic acid reactions were investigated by modifying the ratio of initial reagents based on the above mentioned data. Based on the results of the experiment, it was determined that the reaction carbazole with acrylic acid would proceed without catalysts and catalysts.
Experimental part. Carbazole(dibenzopyrrole) C12H9N - light yellowish crystalline with sharp odor. T = 245-246 °C, T,. .. = 245-246 °C dis-
boiling ' liquid
solves in acetone, alcohol, toluene. Acryl acid (propene acid) CH2 = CHCOOH. T = 141.6 °C,
d = 1.051l2,0, dissolves in acetone, ethanol, ether.
4
In the case of polypropylene colorless granules, the brand J = 150, d = 0.92-93g/sm3, Tliquid=185.2 r, Tliquid= 47.7g, is dissolved in the deethylath-er dekaline. DAA(dinitrile-azo-bisizooil acid) C8H12N4 colorless white crystalline substance. T, ,= 103-105°C. Solvent acetone, benzene, alcohol
liquid ' '
[5, 392]. IQ-Fure spectrophotometer SISTEM-200, PMR-spectrophotometer Varian UNITY - 400.
N-Acryloylcarbazole synthesis. Dina-Starta, a rectangular tube, a reverse refrigerator, an electric plug, a water separator were used for N-Acryloylcar-bazole synthesis. 0.1 ml of carbazole was dissolved in the solvent DMFA and 0.5 mol of acrylic acid with hydroxinone was added. The reaction was carried out at a temperature close to the solvent boil degree for 3 hours and the yield of the product was 72%. The purity of the synthesized compounds was determined by thin-layer chromatography using Silofol
+ CH2=CH-
plates. System: eluent-benzene-acetone, iodine vapors were used. Rf = 0.8 and Rf = 0.67.
Modification of N-acryloylcarbazole to polypropylene. The modification of acryloylocarbazole to polypropylene was carried out at DMFA and dekaline at room temperature and at 80 oC. DAA was used as aa initiator. The process was carried out for 3 hours in a water bath.
Analysis of results obtained. The reaction of Carbazole and acrylic acid was performed without the use of catalysts in this study. The concentration of the initial reagents without the addition of the catalyst was adjusted to the reaction.
In this study, there was observed the formation of quaternary ammonium (bases) when the ratio of carbazole and acrylic acid to 1: 3 in the reaction. When the same reaction reagent ratio was changed to 1:5 N-(vinylcarbinol) carbazole product was obtained. In this reaction, demethylformamide was used as a solvent. In the experiment, the reaction mechanism can go through the SN2 mechanism because the reaction can be carried out without catalysts and catalysts. When the catalyst is present in the reaction, the catalyst is the aprotone catalyst and allows the reaction to proceed with the SN1 mechanism. The solvents make it easier for the reaction to undergo in the Sn2 mechanism. As a result of the experimental results, it can be said that the electrophilic reaction goes according to the SN1 mechanism. The total appearance of carbazole and acrylic acid reaction can be summarized as follows:
N I
H
The synthesized N-acryloylcarbazole (AC) and quaternary ammonium salt can be found in the following table.
The structure of the synthesized N-aryloylocar-bazole was determined using the IQand YMR1N spectra. The initial reagents and the IQ-spectrum of the obtained product were obtained (fig. 1).
Table 1.
Carbazole: Ac The yield of products,% Liquefaction Temperature, °C Thin Layer Chromatography, Rf
AC Ammonium salt AC Nitric ammonium salt AC Clastic ammonium salt
1:1 22 - - - - -
1:3 25 52 200 220 0.32 0.67
1:5 72 22 200 220 0.80 0.28
In the IQ-spectrum of N-acryloylcarbazole obtained by comparison with them, the formation of carbazole primary structures has been observed to have a new absorption potential in the field of
double and single bonds. Valence vibrations of the C = O group in 1717 cm-1 and corresponding absorption areas of the valley vibration of the N-C bond in 1282-1306 cm-1 were observed.
90.CI
35.0.
4000.0 3600
1800 1600 cm-1
%T
1717.14
400.0
Figure 1. IQ-spectral analysis of N-acryloylocarbazolyl
Additionally, valence vibrations of the CH2 group were observed in the 1403-1446 cm-1, de-formational vibrations of 716 cm-1.
In the PMR1N spectrum of the N-Acryloyl carbazole, doublet-doublet signals of protons in the first and eighth carbon atoms of the aromatic nucleus in 8.22 m.u.field, double-triplet-triplep sig-
nals of protons in the second and seventh carbon atoms in 7.43 m.u. field, doublet-doublet-doublet signals of protons in the fourth and fifth carbon atoms in 8.05, and singlet signals of CH group in 3.52 m.u., doublet signals of CH2 in 4.3 m.u. were determined (fig. 2). PMR spectra were obtained by Varian UNITY - 400.
Fig. 2. PMR-spectral analysis of N-acryloylocarbazolyl
Polypropylene is thermoplastic polymer that possesses the density of0.92-0.93 g/cm3 and softening temperature of 185 °C, does not dissolve in any solvent at room temperature. Polypropylene is resistant to concentrated acids and alkalis. Polypropylene is used as a variety of electrostatic material and as a coating for various purposes. Linear polymers are obtained on the base of polypropylene, and we
have studied the modification of acryloylcarbazole to polypropylene. Polypropylene and acryloylcarbazole modification reaction is shown as below:
CH CH2 CH CH2
CH3 n CH3
N
C=O CH CH2
N
C=O CH CH2
Conclusion PMR-spectral analyses methods. The modification
N-acryloylcarbazole has been synthesized by the reaction of polypropylene and N-acryloylcarbazole
interaction of carbazole and acryl acid. The structure has been conducted. The optimal condition of reac-
of N-acryloylcarbazole has been tested through IR-, tion has been determined.
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