Synthesis of complexes of norborn-5-en-2-carboxylic acid amide with hexylchloride and studying of their bactericidal properties in biocorrosion process

Issue 24(4) 2019
Pages 41-50

V.H. Babayeva, Institute of Petrochemical Processes named after Y.H. Mamedaliyev of National Academy of Sciences, Baku, Azerbaijan

E.H. Mamedbeyli, Institute of Petrochemical Processes named after Y.H. Mamedaliyev of National Academy of Sciences, Baku, Azerbaijan

D.B. Agamaliyeva, Institute of Petrochemical Processes named after Y.H. Mamedaliyev of National Academy of Sciences, Baku, Azerbaijan

A.R. Azizbeyli, Institute of Petrochemical Processes named after Y.H. Mamedaliyev of National Academy of Sciences, Baku, Azerbaijan

N.M. Mamedova, Institute of Petrochemical Processes named after Y.H. Mamedaliyev of National Academy of Sciences, Baku, Azerbaijan


Keywords: microbiological corrosion, amide, norborn-5-en-2-carboxylic acid, triethylene tetraamine, sulphatereducing bacteria, inhibitor

http://www.doi.org/10.31615/j.corros.prot.2019.94.4-5

 

The synthesis of norborn-5-en-2-carboxylic acid by the reaction of cyclopentadiene with acrylic acid with 97% yield was carried out. Based on norborn-5-en-2-carboxylic acid and triethylenetetraamine, its amide was synthesized with 83% yield at a temperature of 130…140 °C during 2 h with escape of 1 mole of water. To obtain inorganic anionic complexes of amide of norborn-5-en-2-carboxylic acid at different ratios (1:1, 1:2, 1:3), alkyl halides, in particular hexylchloride, were used. Considering that the boiling point of hexylchloride is 135 °C, the reaction is mainly carried out in the temperature range of 50…60 °C for three hours with stirring. The physicchemical parameters of the compounds obtained and their complexes were determined. The structure and composition of the obtained substances were confirmed using IR- and 1H NMR spectroscopy. In order to study the antimicrobial activity of the obtained complexes, their aqueous solutions were prepared at three different concentrations (25; 50; 100 mg/l) and their effect on the vital activity of sulfate-reducing bacteria (SRB) was studied at a temperature of 30…32 °C for 7…14 days. It was established that complexes with hexylchloride at ratios of 1:1 and 1:2 at a concentration of 100 mg/l (A-25; A-26) exhibit a bactericide-inhibitory effect of 97…98%, and the complex at a ratio of 1:3 almost completely inhibits the growth of SRB (99.3%). It was revealed that the obtained complexes have a relatively higher antimicrobial activity against SRB than industrial bactericide inhibitors AMDOR-IR-7 (standard) and AMDOR-IR-10 (standard). On the basis of the conducted studies, it was established that the complexes synthesized on the basis of alkylamides completely inhibit the growth of SRB at much lower concentrations compared to the industrially used bactericide inhibitors AMDORIR-7 and AMDOR-IR-10 (at a concentration of 25 mg/l 92…96% opposite 40%).