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

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.

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:)

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 — CH_{2 —} 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 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

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