M. R. Bairamov

Investigation of the Molecular Dynamics of Some Phenols and Their Acetyl Isomers in Solutions by NMR Relaxation

The dynamics of relaxations and Fries rearrangements in phenol acetates and their acetyl isomers was studied by the NMR relaxation technique in acetone-d6. The results of 13C and 1H spin-lattice nuclear relaxation measurements show that these experiments can be used for determining the mobility and activation energies of the molecular motions of compounds in different systems.

Synthesis of hydrogen sulfide corrosion inhibitors for oil production

Pyridinium salts have been synthesized by reacting 2-allyl- and 4-propenylphenoxy(C2–C4)bromoalkanes with pyridine and further examined as inhibitors of hydrogen sulfide corrosion of St3 steel in water-salt systems containing H2S. The dependence of the protective properties of the test compounds on their structure has been revealed. It has been found that N-(2-propenylphenoxytetamethylene)pyridinium bromide exhibits the best inhibitory properties (degree of corrosion protection at a concentration of 100 mg L−1 is 96.0%).

The molecular mobility of 2-propenylphenols capable of hydrogen bonding

Hydrogen bonding and molecular mobility of 2-propenylphenols containing an aminomethyl fragment in the ortho position were studied by NMR. The results confirmed the importance of using relaxation times as a sensitive test for molecular dynamics studies.

Synthesis of co-oligomers of 2-propenylphenol with maleic anhydride and study of products of their transformations with amines as steel corrosion inhibitors

Modification with diethylamine and diethanolamine of co-oligomers of 2-propenylphenol with maleic anhydride yielded water-soluble nitrogen-containing derivatives inhibiting the corrosion of St.3 steel in watersalt solutions.

Study of Radical Copolymerization of Aminomethylated Derivatives of Alkenylphenols with Styrene

Aminomethylated derivatives 2-propenyl-, 2-allyl-, and 4-isopropenylphenols are studied as comonomers in free-radical copolymerization with styrene in bulk. As evidenced by NMR studies, in o-aminomethyl derivatives of alkenylphenols, stable intramolecular hydrogen bonds form between nitrogen atom of the aminomethyl fragment and hydrogen atom of the hydroxyl group; these bonds are not destroyed up to 80°C Therefore, these compounds may be involved in free-radical copolymerization with styrene in which the inhibiting effect of OH groups is avoided at a temperature of 60°C. The values of r 1 and r 2 are determined for two pairs of comonomers: 6-morpholinomethyl-2-propenylphenol and styrene (r 1 = 0.20 ± 0.01 and r 2 = 2.40 ± 0.04) and 2-allyl-6-morpholinomethylphenol and styrene (r 1 = 0.090 ± 0.009 and r 2 = 2.40 ± 0.04).

Synthesis of 1-(4-isopropenylphenoxy)-bromo-C2-C4-alkanes and application of their transformation products

Reaction of 4-isopropenylphenol with α,ω-dibromo-C2-C4-alkanes by the Willamson reaction in the presence of potassium iodide as promoter, aiming to synthesize the corresponding monobromosubstituted derivatives and to study their some chemical transformation. Optimal conditions to obtain 1-(4-isopropenylphenoxy)-2-bromoethane, 1-(4-isopropenylphenoxy)-3-bromopropane and 1-(4-isopropenylphenoxy)-4-bromobutane were found. The nitrogen-containing derivatives, inhibitors of a hydrosulfuric corrosion in the water-salt solutions, were obtained on the basis of the first two compounds. The derivatives involving multiple bond and ester-group were synthesized from the third compound. Their incorporation into the polystyrene chains in the process synthesis gives them plasticize properties.

Synthesis of aminomethylated derivatives of allylphenols and study of their antimicrobial characteristics in motor oil

A series of nitrogen-containing compounds was synthesized by Mannich condensation of allylsubstituted derivatives of phenol and o-and p-cresols with formaldehyde and secondary amines. These compounds were studied as antimicrobial additives to motor oil (at a content of 1–2 wt %).

Alkenylphenol-based pyridinium salts as hydrogen sulfide corrosion inhibitors and agents for inhibiting the growth of sulfate-reducing bacteria in oil production

The results of gravimetric and potentiostatic studies of pyridinium salts, derived from alkenylphenols, as inhibitors of hydrogen sulfide corrosion of steel St 3 in aqueous saline and hydrocarbon systems and testing the salts for bactericidal activity against sulfate-reducing bacteria (SRB) are reported. It has been found that the test compounds with a concentration of 50–150 mg/L slow down the cathodic and anodic reactions and significantly increase the polarization resistance (Rp) of St 3. The best protective properties have been shown by 1-(2-propenylphenoxytetramethylene)-N-pyridinium bromide (III) and 1-(2-allylphenoxytetramethylene)-N-pyridinium bromide (VI): the corrosion protection by III and VI is respectively 87 and 83% at a concentration of 50 mg/L or 96 and 93% at a concentration of 150 mg/L. The pyridinium salts synthesized in this study also exhibit bactericidal activity in a concentration of 50–200 mg/L. High bactericidal properties have been found for 1-(2-propenylphenoxytetramethylene)-N-pyridinium bromide. The SRB growth inhibition at its concentration of 50 or 75 mg/L is 75 or 100%, respectively.

Aminomethylated derivatives of 2-propenyl- and 4-isopropenylphenols as antimicrobial additives for petroleum products

A number of aminomethylated derivatives of 2-propenyl-, 4-isopropenylphenols have been synthesized and their antimicrobial properties have been studied in M-12 engine oil and TS-1 jet fuel (at concentrations of 1–2% and 0.3–0.5%, respectively). They have been found to possess bactericidal and fungicidal properties and significantly improve the antimicrobial properties of both of the materials (as compared to the well-known antimicrobial additive, 8-hydroxyquinoline). The presence of an alkenyl substituent along with an aminomethyl group in the structure of the substances in question has been demonstrated to enhance the antimicrobial properties. The formation of an intermolecular and intramolecular hydrogen bond in the initial and synthesized phenolic compounds has been studied.

Di(4-isopropenylphenoxy)alkanes as cross-linking comonomers in three-dimensional copolymerization with styrene

Di(4-isopropenylphenoxy)alkanes were synthesized by condensation of 4-isopropenylphenol with symmetrical dihaloalkanes in the presence of KI promoter. Three-dimensional polymeric structures were prepared by compolymerization of these monomers with styrene.