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THEORETICAL FOUNDATIONS OF THE HOMOGENEOUS CATALYTIC
VINYLATION REACTION OF CYANURIC ACID
Ziyadullayev Anvar Egamberdiyevich
Associate Professor, Tashkent Institute of Chemical Technology
Nuriddinov Jonibek Fozil o'g'li
Master's student at the Tashkent Institute of Chemical Technology
To'rayeva Dilrabo Fakhriddinovna
PhD student at Tashkent Institute of Chemical Technology
Nigmatova Komila Kholiq qizi
Senior lecturer at the Tashkent Institute of Chemical Technology
Abstract: The paper information of the synthesis vinyl ester of cyanuric acid,
by catalytic vinylation involving acetylene under the influence of various catalysts at
atmospheric pressures, the use of highly basic systems, alternative conditions for the
process and reaction mechanisms of formation of vinyl compounds of cyanuric acid
is presented.
Key words: acetylene, vinylation, esters of cyanuric acid, mono,- di- and
three vinyl cyanurates.
Introduction
At present, vinyl ethers are widely used in various industries, including: as
biologically active substances in medicine; as monomers for the production of
polymers and plastic materials; as inhibitors in the oil and gas industry; as
crosslinking agents in the production of rubber and synthetic rubber; as adhesives in
microelectronics; and as various solvents in the textile industry [1,2].
Vinyl compounds of cyanuric acid have been synthesized through catalytic vinylation
involving acetylene, utilizing the active hydrogen atoms of cyanuric acid [3,4].
Scientific Novelty.
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The influence of the nature of the solvent and catalyst, temperature, and the
rate of acetylene feed on the formation of vinyl compounds based on cyanuric acid
has been studied.
Research Results and Discussion:
DMSO and DMF were used as solvents, while LiOH, NaOH, and KOH were
used as catalysts. As a result, the formation of mono-, di-, and trivinyl ethers of
cyanuric acid was established. The formation of vinyl ethers of cyanuric acid is
explained as follows: Initially, due to the interaction of KOH with DMSO, a highly
basic system is formed:
Which, under the influence of a cyanuric acid molecule, forms a potassium
compound through the active hydrogen atom of the hydroxyl group:
Under the influence of acetylene, the potassium compound of cyanuric acid
undergoes nucleophilic addition:
After this, as a result of the hydrolysis of the intermediate compound, a mono-
vinyl ether of cyanuric acid is formed:
During the process, due to the involvement of the second and third hydroxyl
groups, di- and tri-vinyl ethers are formed:
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The reactions were carried out at 120 °C in the presence of various solvents
(DMSO and DMFA) for a duration of 4–8 hours. The starting compounds were used
in equimolar ratios.
As a result, when using DMSO, the product yield was significantly higher
than when using DMFA. Additionally, the yield of vinyl ethers increased
considerably with an increase in reaction time from 4 to 6 hours; however, a sharp
decrease in the formation of vinyl ethers was observed at 8 hours.
Table 1
Effect of Solvent and Reaction Duration on the Yield of Vinyl Ethers of
Cyanuric Acid (Temperature 120 °C)
Synthesized Vinyl Ethers Product Yield, %
In DMFA
In DMSO
Reaction Time: 4 hours
I
10.2
16.0
II
11.8
18.0
III
12.2
18.5
Reaction Time: 6 hours
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Synthesized Vinyl Ethers Product Yield, %
I
12.6
18.2
II
14.5
21.8
III
12.6
22.6
Reaction Time: 8 hours
I
10.6
12.0
II
11.2
12.7
III
13.4
13.2
The influence of temperature, as well as the nature of the solvent and catalyst,
on the product yield was studied and analyzed. The results showed that when the
reaction was carried out using DMSO for 6 hours, the yield of vinyl ethers reached a
maximum: I – 18.2%; II – 21.8%; III – 22.6%.
The reaction of cyanuric acid with acetylene was carried out for 4, 6, and 8
hours at temperatures ranging from 80 to 140 °C. When the reaction was conducted
in the presence of KOH in DMFA and DMSO at 80 °C, the yield of vinyl ether was
26.9% and 39.2%, respectively. At 120 °C, the yields increased to 39.7% and 62.6%,
respectively.
However, when the temperature was raised to 140 °C, the yield of vinyl ethers
sharply decreased due to the partial decomposition of dimethyl sulfoxide.
THE INFLUENCE OF TEMPERATURE, CATALYST TYPE, AND
SOLVENT NATURE ON PRODUCT YIELD (REACTION DURATION: 6
HOURS, CATALYST AMOUNT: 10% OF THE MASS OF CYANURIC ACID)
Catalyst
Temperature, °C I
II
III Total %
Solvent: DMFA
KOH
80
6.5 8.4 12.0 26.9
NaOH
LiOH
100
8.2 10.2 10.8 29.2
KOH
120
12.6 14.5 12.6 39.7
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Catalyst
Temperature, °C I
II
III Total %
NaOH
140
10.4 10.2 6.8 27.4
It should be emphasized that the yields of vinyl ethers of cyanuric acid using
KOH as the catalyst and DMSO as the solvent are the highest.
DMFA and DMSO are aprotic solvents with high dielectric permittivity and
have
a
positive
effect
on
the
course
of
nucleophilic
reactions.
In all cases, when using DMSO, the yields...
(sentence incomplete — please send the
next part if you want the rest translated).
The yield of the products was higher when DMSO was used compared to
DMFA. This is due to the fact that DMSO, in combination with the catalyst, forms a
highly basic system, which increases the solubility of acetylene [5,6].
The effect of temperature, nature of the catalyst, and solvent on the synthesis
of vinyl ethers of cyanuric acid can be explained as follows:
Potassium hydroxide (KOH) exhibits higher catalytic activity than
NaOH and LiOH;
DMFA, as a solvent, acts as a weak protonic acid and undergoes
autoprotolysis due to the positive charge on the nitrogen atom. As a result, it does not
form active homogeneous conditions and slows down the rate of vinylation;
DMSO contains two nucleophilic centers – a hard oxygen atom and a
soft sulfur atom. The hydrogen atoms are highly prone to protonation, and in the
presence of alkali, catalytic active intermediate complexes are formed, creating
favorable conditions for acetylene addition [7].
The obtained results showed that with an increase in the amount of catalyst
(5–15%), the product yield increases. At a reaction duration of 6 hours, in the presence
of DMSO as solvent and 10% KOH, the monovinyl ether was synthesized with a yield
of 18.2%; the divinyl ether – 21.8%; and the trivinyl ether – 22.6%.
Further increase in the reaction time and catalyst amount negatively affects
the formation of products.
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The activation energy and reaction rate were calculated in order to determine
the kinetic parameters for the synthesis of mono-, di-, and tri-vinyl ethers of cyanuric
acid (Tables 4–6).
Table 4
Kinetic Parameters of the Synthesis Process of Monovinyl Ether of
Cyanuric Acid (Solvent: DMSO, Catalyst: KOH)
Reaction
Duration (h)
Temperature
(°C)
Product
Yield (%)
Product
Yield
(mol/L)
Average
Reaction Rate
(%/h)
Average
Reaction
Rate
(mol/L·h)
4
80
12.6
1.03
4.56
0.23
100
15.3
1.25
5.53
0.27
120
16.0
1.30
5.87
0.28
140
13.6
1.10
4.98
0.23
6
80
12.2
0.99
4.41
0.22
100
16.7
1.35
6.03
0.30
120
18.2
1.47
6.57
0.32
140
16.4
1.32
5.92
0.28
8
80
10.6
0.80
3.81
0.19
100
11.2
0.85
4.02
0.20
120
12.0
0.92
4.30
0.21
140
10.8
0.83
3.89
0.20
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Table 5
Kinetic Parameters of the Synthesis of Divinyl Ether of Cyanuric Acid
(Solvent: DMSO, Catalyst: KOH)
Reaction
Duration
(hours)
Temperature
(°C)
Product
Yield (%)
Product
Concentration
(mol/L)
Average
Reaction
Rate (%/h)
Average
Reaction Rate
(mol/L·h)
4
80
12.6
1.03
4.56
0.23
100
14.2
1.16
5.14
0.26
120
18.0
1.48
6.52
0.33
140
12.2
1.00
4.41
0.22
6
80
14.6
1.19
5.28
0.26
100
18.6
1.51
6.73
0.34
120
21.8
1.78
7.89
0.40
140
16.0
1.30
5.27
0.29
8
80
9.8
0.80
3.54
0.17
100
10.2
0.83
3.69
0.18
120
12.7
1.04
4.60
0.23
140
12.2
0.99
4.41
0.22
Table 6
Kinetic Parameters of the Synthesis of Trivinyl Ether of Cyanuric Acid
(Solvent: DMSO, Catalyst: KOH)
Reaction
Duration
(hours)
Temperature
(°C)
Product
Yield (%)
Concentration
(mol/L)
Yield
per
hour
(%/hour)
Reaction
Rate
(mol/L·hour)
4
80
12.4
1.01
4.48
0.22
100
14.6
1.19
5.28
0.26
120
18.5
1.50
6.69
0.32
140
16.2
1.66
5.85
0.28
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Reaction
Duration
(hours)
Temperature
(°C)
Product
Yield (%)
Concentration
(mol/L)
Yield
per
hour
(%/hour)
Reaction
Rate
(mol/L·hour)
6
80
12.4
1.01
4.48
0.22
100
14.8
1.20
5.33
0.26
120
22.6
1.86
8.15
0.42
140
10.8
0.88
3.89
0.20
8
80
10.2
0.83
3.69
0.18
100
11.8
0.96
4.27
0.21
120
13.2
1.07
4.77
0.23
140
12.6
1.03
4.56
0.22
Conclusion:
The kinetic parameters of the synthesis of vinyl esters of cyanuric acid were
analyzed. The average reaction rates were determined, and the activation energies
were calculated. It was established that at a reaction duration of 6 hours and a
temperature of 120 °C, the yields of the vinyl esters reach their maximum values:
1.
mono-vinyl ester
— 18.2%,
2.
di-vinyl ester
— 21.8%,
3.
tri-vinyl ester
— 22.6%
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