Synthesis of a new diphenylcarbazide derivative based N1',N1' — di (2-chloro-5-oxohexene-2) chlorazone ester and a study as a corrosion ecologically effective inhibitor | Статья в журнале «Молодой ученый»

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Библиографическое описание:

Гаджиева С. Р., Байрамов Г. И., Гусейнов Ф. Э., Алиева Т. И., Велиева З. Т., Рустамова У. Н., Джафарова Н. М., Гасымлы Ф. Э. Synthesis of a new diphenylcarbazide derivative based N1',N1' — di (2-chloro-5-oxohexene-2) chlorazone ester and a study as a corrosion ecologically effective inhibitor // Молодой ученый. — 2020. — №1. — С. 1-6. — URL https://moluch.ru/archive/291/65909/ (дата обращения: 22.02.2020).



Using the main waste product of the production of synthetic rubber 1,3-dichlorobutene-2 as the main raw material, its alcohol CH3-CCl=CH-CH2OH and its α-chloroether CH3-CCl=CH-CH2OCH2Cl were obtained. As a result of the interaction of this ester with chlorazone, N1',N1'-di (2-chloro-5-oxohexene-2)chlorazone ether was obtained, on the basis of which a new diophenylcarbazide derivative, conditionally designated as compound B-4, was synthesized. Studies have been conducted to identify the inhibitory efficiency of a new diphenylcarbazide derivative (compound B-4), which was first synthesized and unknown from the literature. As our studies have shown, compound B-4 with respect to existing inhibitors used has highly effective properties even at the lowest concentrations of 0.10; 0.15; 0.25 mg /l in highly aggressive environments [3 % NaCl + oil (10:1) + H2S 500 mg / l; 0.3 N HCl + gasoline (1:7) + H2S 1000 mg/l]. Considering that this compound has a high boiling point and meets modern ecological requirements, it can be considered scientifically valid for its use in the oil and gas and petrochemical industries for corrosion protection of steel processing equipment in highly aggressive environments.

Thus, in addition to the fact that the new synthesized diphenylcarbazide derivative (compound B-4) is of great importance from an ecological and economic point of view, it can also be characterized as an ecologically effective inhibitor that prevents ecological problems in these industries.

Key words: synthetic rubber, industrial waste, 1,3-dichlorobutene-2, α-chloroether, chlorozone ether, diphenylcarbazide derivative, inhibitor, corrosion, oil and gas industry, petrochemistry, steel, technological, ecological.

Recently, in connection with the emergence of ecological problems and the need for complete protection of steel processing equipment in the oil and gas and petrochemical industries from high temperatures and a strong aggressive environment, a need has arisen for the use of highly ecologically effective inhibitors. That is why the synthesis and use of new nitrogen, nitrogen-sulfur containing organic compounds with high inhibitory efficiency at low concentrations and in highly aggressive environments, using cheap raw materials and industrial waste, is one of the urgent issues of petrochemistry and organic chemistry.

As can be seen from the technical literature [3] and the results of our studies [2,4–11], organic compounds containing nitrogen, -CH2OR, -C6H5 and other functional groups, as well as a large number of double bonds, even in the smallest concentrations and in a highly aggressive environment, have highly effective inhibitory properties.

For this purpose, we synthesized and studied the nitrogen-containing organic compound B-4, which is of great ecological and economic importance for the oil and gas and petrochemical industries and has highly effective inhibitory properties.

High inhibitory ability B-4 can be explained based on the results of our previous studies [2,4–11], as well as on literature data [12–24]. The new synthesized diphenylcarbazide derivative (compound B-4) contains 16 nitrogen atoms, 6 CH3-CCl=CH-CH2OCH2 groups, 6 С6Н5 groups, 34 double bonds, which increases the electron density, as well as internal Van der Waals forces, which causes coordination on the metal surface with this compound.

Based on this, it is very likely that the metal surface in the presence of compound B-4 is passivated, the corrosion rate approaches zero, and this, in turn, determines the 100 % inhibitory efficiency of the compound.

In the process of research in the most aggressive environments prepared under laboratory conditions [3 % NaCl + oil (10:1) + H2S 500 mg/l; 0.3 N HCl + gasoline (1:7) + H2S 1000 mg /l] 99.92–100 % inhibitory efficiency of compound B-4 was established at its concentrations of 0.10; 0.15; 0.25 mg/l.

The results of the study to determine the inhibitory characteristics of compound B-4 are given in Table 2.

This compound, in terms of its inhibitory efficiency and high boiling point, is several times (even 10 times) superior (from economic and environmental point of view) to the inhibitors currently used in the oil and gas and petrochemical industries. At the same time, the synthesized new diphenylcarbazide derivative, compound B-4, is evaluated as an ecologically friendly, effective inhibitor that highly meets all the requirements of modern ecological safety.

Therefore, the use of compound B-4 as an ecologically effective inhibitor of the corrosion that causes major ecological problems in the oil and gas and petrochemical industries, can be considered scientifically valid.

The main chemical compounds required for the synthesis are CH3-CCl=CH-CH2OH, CH3-CCl=CH-CH2OCH2Cl, were obtained by the appropriate methods indicated elsewhere [2,4–11]. Elemental analysis, IR and mass spectra of these compounds corresponded to those indicated in the literature [2,4–11].

As a result of the reaction of diphenylcarbazide with the obtained N1', N1'- di (2-chloro-5-oxohexene-2) chlorazone ether, a new derivative N1 — [N1', N1'- di (2-chloro-5-oxohexene-2)]azone — N2 — [N1', N1'-di (2-chloro-5-oxohexene-2)]azone — — N4 — [N1', N1'-di (2-chloro-5-oxohexene-2)]azone — N5 — [N1', N1'-di (2-chloro-5-oxohexene-2)]azondiphenylcarbazide, (compound B-4 was synthesized).

The yield, physicochemical constants and elemental analysis of this compound are shown in Table 1.

Experimental part

Synthesis of N1 — [N1', N1'-di (2-chloro-5-oxohexene-2)] azone — N2 — [N1', N1'-di (2-chloro-5-oxohexene-2)]azone — N4 — [N1',N1'-di (2-chloro-5-oxohexene-2)] azone — N5 — [N1',N1'-di (2-chloro-5-oxohexene-2)] azondiphenylcarbazide (compound B- 4:)

2 g of ZnCl2, 0.01 g-mole of diphenyl carbazide are placed in a reaction flask and 50 ml of ethanol are added. The mixture is stirred until diphenylcarbazide is completely dissolved in ethyl alcohol at 70°C and then 0.04 g mol N1',N1'-di (2-chloro-5-oxohexene-2)chloroazone ether is added to it through a dropping funnel. After the addition of chlorazone ether, the reaction mixture is stirred for 6 hours at a temperature of 76°C. After neutralizing the reaction mixture at room temperature with 50 ml of a 10 % NaOH solution and repeatedly washing with 200 ml of distilled water, 25 ml of diethyl ether is added to it. The resulting mixture, stirring, is transferred to a separatory funnel. After separation of the organic phase from the aqueous phase, the diethyl ether contained in it is stripped distilled using a water pump. After the reaction product was completely dried over CaCl2 and stripped in a vacuum unit, a new diphenylcarbazide derivative was obtained — compound B-4: N1 — [N1', N1'-di (2-chloro-5-oxohexene-2)] azone — N2– [N1',N1'- di(2-chloro-5-oxohexen-2)]azone-N4– [N1',N1'-di(2-chloro-5-oxohexene-2)]azone- N5- [N1',N1'-di(2-chloro-5-oxohexene-2)]azondiphenylcarbazide.

The composition and structure of this compound was studied by known methods — elemental analysis, as well as IR- and mass-spectroscopy.

The following absorption bands were observed in the IR-spectrum of compound B-4: C6H5 groups — at 700–780 cm-1; bonds C = C of the benzene ring at 1440, 1465, 1500, 1510, 1590–1600 cm-1; alcohol ether groups -CH2 — O — CH2 at 1050, 1080 cm-1; CH2 groups at 2950 cm-1; CH3 groups at 1380, 1460, 2960, 3030 cm-1; C-N bonds of the azone group at 1310–1350 cm-1; C = C bonds at 1680 cm-1, as well as the C-Cl bond of the 2-chloro-5-oxohexene-2 group at 680 cm-1, C = C bonds at 1640 cm-1.

In the magnetic mass-spectrum, the molecular weight of this compound corresponded to 1930 m/e of its molecular ion.

Elemental analysis, physico-chemical properties, yield of N1— [N1', N1'-di (2-chloro-5-oxohexene-2)]azone— N2–[N1',N1'- di(2-chloro-5-oxohexen-2)]azone-N4– [N1',N1'-di(2-chloro-5-oxohexene-2)]azone- N5- [N1',N1'-di(2-chloro-5-oxohexene-2)]azondiphenylcarbazide (compound B-4)


Table 1

The chemical formula of the compound, conditional number

Yield, %

Tboil, °С (Torr)

MRD found / calculated

Grossformula, mol. Mass

Elemental analysis,%

Calculated /found

C

H

N

Cl

Compound В-4

98,84

351–352 (2)

1,7926

1,9418

C93H98N16O13Cl8

1930


The results of the study of the inhibitory effectiveness of anew derivative of diphenylcarbazide (compound B-4) synthesized on the base of N1',N1'-di (2-chloro-5-oxohexen-2) chlorazone ether

Table 2

Conditional number of the compound

Inhibitorconcentration, mg /l

3% NaCl + oil (10:1) +

+ H2S 500 mg/l

0.1 NHCl + gasoline (1:7) +

+ H2S 1000 mg/l

Corrosion rate,

g/cm2hour

Effectivenessof the inhibitor, %

Corrosion rate, g/cm2hour

Inhibitoryefficiency,%

Without inhibitor

-

2,56

Compound

B-4

0,1

0,15

0,25

0,0018

0,0006

0,0001

99,92

99,97

100

0,0002

0,0001

99,99

100

A [11]

200

98,5

98

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