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22
ISSN 2522-1841 (Online) AZERBAIJAN CHEMICAL JOURNAL № 2 2022 ISSN 0005-2531 (Print)
UDC 547.56.563.364
SYNTHESIS OF AMINOMETHOXY DERIVATIVES OF CYCLOHEXANOL AND STUDYING THEM AS BACTERICIDE INHIBITORS
1 12 1 S.V.Ismayilova1, E.G.Mammadbeyli1, K.A.Kochetkov2, G.E.Hajiyeva1,
3 1
L.M.Maharramova3, D.B.Agamalieva1
1Yu.Mamedaliyev Institute of Petrochemical Processes, NAS of Azerbaijan A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences 3Azerbaijan State Oil and Industry University
ismayilova_s_ch@mail.ru
Received 17.12.2021 Accepted 25.01.2022
Based on cyclohexanol, cyclic amines (piperidine, morpholine, hexamethyleneimine), and formaldehyde, new Mannich bases have been synthesized. The reaction was carried out at a temperature of 78-800C for 4-5 h in a benzene solution at an equimolar ratio of the starting components. The yield of compounds was 69-75%. The physicochemical data of the synthesized compounds were determined. The composition and structure of the target products were confirmed by elemental analysis, IR, 1H and 13C NMR spectroscopy, and mass spectrometry. Their effect on the vital activity of sulfate-reducing bacteria of the "Desulfovibrio desulfuricans" type at three concentrations (25; 50; 100 mg/l) was studied. The obtained compounds showed high bactericidal properties, 1% solutions of these compounds in isopropyl alcohol at a concentration of 100 mg/l showed 100% bactericidal effect. A 1% solution of the compound with a fragment of morpholine already at a concentration of 50 mg/l exhibits a 100% bactericidal effect. Compounds with a fragment of piperidine and hexamethyleneimine at a concentration of 50 mg/l showed 96.2 and 98% bactericidal effects, respectively. And at a concentration of 25 mg/l, the bactericidal effect of all three compounds was 16.4%, 36.4%, and 58.2%, respectively. The results obtained show that the synthesized compounds showed more bactericidal properties compared to the industrially used bactericide-inhibitors AM^OP HK-7 and AM^OP HK-10 taken as a standard. Established, that these aminomethoxy derivatives of cyclohexanol affect bacteria at very low concentrations, they can be proposed as effective inhibitors against sulfate-reducing bacteria.
Keywords: cyclohexanol, secondary amines, Mannich bases, sulfate-reducing bacteria, inhibitor-bactericides, biocorrosion.
doi.org/10.32737/0005-2531-2022-2-11-17 Introduction
A significant part of the corrosion damage of oilfield equipment is due to the vital activity of a number of microorganisms and, first of all, sul-fate-reducing bacteria (SRB) [1, 2]. Sulfate-redu-cing bacteria, a group of anaerobic prokaryotes, are widely distributed in various anoxic habitats such as lakes, swamps, rice fields, oil fields, underground pipelines, and some industrial wastewater. Oil companies are showing an increased interest in inhibitors, which, along with slowing down hydrogen sulfide and carbon dioxide corrosion of metal equipment, have a bactericidal effect on SRBs [3, 4].
Organic compounds containing various functional groups and heteroatoms, such as sulfur and nitrogen, along with biological activity, are characterized by antimicrobial activity [5].
Among the biologically active compounds of the cyclohexane series, their amine-containing derivatives stand out, the value of which is associated with the presence of two pharmaco-phore fragments in their molecules - a nitrogen-containing group and a cyclohexane ring [6, 7].
One of the convenient methods for the synthesis of new generations of functionally substituted aminomethoxy derivatives is the three-component Mannich reaction, since the use of various starting compounds with an active hydrogen atom, as well as amine and aldehyde components, makes it possible to obtain a wide range of polyfunctional derivatives of this class of compounds [8-11]. Mannich bases with a cyclohexane fragment, which have a wide range of properties, also exhibit bactericidal properties [12-16], but their effect on the
growth of sulfate-reducing bacteria (SRBs) has been little studied [17].
Discussion of the results
This paper presents the results of the synthesis and study of the properties of ami-nomethoxy derivatives of cyclohexanol. For
+ CH2=0 + HN
X
I II III-V
X= CH2 (III, VI), O (IV, VII), CH2-CH2 (V, VIII).
The reaction was carried out at a temperature of 78-800C for 4-5 h in a benzene solution at an equimolar ratio of the starting components. The yield of the compounds was 69-75%, with the maximum yield obtained using hexamethyleneimine. Target compounds are liquids with a characteristic odor, insoluble in water, and readily soluble in organic solvents. The composition and structure of compounds VI-VIII were established based on elemental
1 13
analysis, IR, H, and C NMR spectroscopy, and mass spectroscopy.
Thus, in the IR spectra of all synthesized cyclohexanol derivatives (VI-VIII), there is no
this purpose, the Mannich condensation reaction of cyclohexanol (I), formaldehyde (II), and cyclic amines [piperidine (III), morpholine (IV), hexamethyleneimine (V)] was carried out. The reaction proceeds according to the following scheme:
-h2o
VI-VIII
absorption band in the region of 3334 cm1 (Figure 1), which is characteristic of the hydroxyl group, and absorption bands are observed in the regions of 1232 and 1024 cm-1, which are related to stretching vibrations R3N groups, absorption bands in the regions of 1150, 1134 and 1070 cm-1 refer to the stretching vibrations of the simple ether bond (C-O-C). The 1H NMR spectra of compounds VI-VIII fully confirm the structure of the synthesized compounds. The protons of the methyl group in the position of the amine fragment give a signal at approximately 5 = 0.86 ppm. in the form of a triplet (Figure 2).
Fig. 1. IR spectrum of morpholinomethoxycyclohexane (VII).
The protons of the methylene groups give signals in the ranges 5 = 1.2-1.86 ppm in the form of a multiplet, and the protons of the CH2-N-CH2 group, in the regions 5 = 2.4-2.78 ppm. The CHO proton of the cyclohexane ring gives signals approximately in the region of 5 = 4.07 ppm. in the form of a doublet of doublets. The protons of the OCH2N group give signals approximately in the regions 5 = 4.4 ppm in the form of a doublet of doublets (J = 2.5 Hz, J =
6.5 Hz). The 13C NMR spectra of compounds VI-VIII also confirm the structure of the synthesized compounds (Figure 3).
The bactericidal-inhibiting properties according to OST 39-234-89 were studied at three concentrations (25; 50; 100 mg/l), 1143 strains of Desulfovibrio desulfuricans were used as CBR, the nutrient medium was Postgate B, pH 7.0-7.5, the duration of incubation was thermostat at 30-320C - 15 days.
Fig 2. 1H NMR spectrum of hexamethyleneiminomethoxycyclohexane (VIII).
Fig. 3. C NMR spectrum of piperidinomethoxycyclohexane (VI).
For comparison, as standards in the same dilutions (25; 50; 100 mg/l), bactericide-inhibitors used in industry were studied: AMDOR IK-7 (10% solution of higher amines (C10-C16) in an aprotic solvent) and AMDOR IK-10 (a mixture of imidazolines and amidoamines obtained by the interaction of polyethylenepolyamine and oleic acid).
Experimental part
The IR spectra of the synthesized compounds were recorded on a BRUKER instrument (ALPHA IR FURYE) in the range of 4000-400 cm-1. 1H and 13C NMR spectra were recorded on a BRUKER AM-300 spectrometer at a frequency of 300 MHz in CDCl3 solvent, HMDS as the internal standard. Mass spectra were obtained on a VG-7070E mass spectrometer (ionizing voltage 70 eV). The purity of the reaction products was determined from the boiling point, elemental analysis, and gas-liquid chromatography. Elemental analysis was carried out on a CARLOERBA instrument, model EA 1108. GLC analysis was carried out on an LKhM-8 MD chromatograph (Russia), a steel column (300x3 mm) with 5% PEGS on Dinochrome P, carrier gas helium (40 cm3/min), detector - katharometer, column temperature 1500C, evaporator temperature - 230 C. The refractive index (n22 ) was measured with an
ABBEMAT 350/500 refractometer; the relative density (d ) was determined with a pycno-meter [18].
Cyclohexanol was used as the starting compound. boiling point 1610C. Secondary amines (chemically pure) were distilled before use. Paraform, a formaldehyde polymerization product that depolymerizes to formaldehyde when heated during the reaction, was used in the form of a reactive powder. Benzene was taken as a solvent, which was purified and dried according to a known method [19]. Ammonia water, which is a medical preparation, was used in the form of a 10% solution.
The synthesized compounds (VI-VIII) were studied as bactericide inhibitors against SRB according to the procedure [20]. For this purpose, 1% solutions of compounds VI-VIII in isopropanol was prepared. The bactericidal effect of the reagents is studied mainly by observing for 15 days and calculating the amount of H2S formed at the end of the experiment. The formation of H2S is determined by iodometric titration. For comparison, 2 samples without reagent were taken: control 1 and control 2. Control 1 - only Postgate B nutrient medium, control 2 - nutrient medium and SBR cultures. The results of the study are presented in the Table.
Inhibitor-bactericidal properties of 1% solutions of compounds (VI-VIII) in isopropyl alcohol
Reagent Concentration, c, Number of bacteria (num- Amount ofH2S, Bactericidal
mg/l ber of cells/ml) mg/l effect, Z-%
25 10' 213 16.4
VI 50 101 9.6 96.2
100 - - 100
25 106 162 36.4
VII 50 - - 100
100 - - 100
25 104 105 52.7
VIII 50 101 8.4 98
100 - - 100
AM^OP-HK-7 (etalon) 25 stimul. stimul. stimul.
50 104 88.8 60
100 103 55.5 75
AM^OP-HK-10 (etalon) 25 stimul. stimul. stimul.
50 104 77.7 65
100 102 44.4 80
Control 1 - 14.0 -
Control 2 108 222.0 -
The table shows that all three samples showed high bactericidal properties. Moreover, 1% solutions of compounds (VI-VIII) at a concentration of 100 mg/l showed a 100% bactericidal effect. A 1% solution of compound (VII) already at a concentration of 50 mg/l exhibits a 100% bactericidal effect. Compounds (VI and VIII) at a concentration of 50 mg/l showed 96.2 and 98% bactericidal effects, respectively. And at a concentration of 25 mg/l, the bactericidal effect of compounds (VI-VIII) was 16.4%, 36.4%, and 58.2%, respectively.
Synthesis of aminomethoxy derivatives of cyclohexanol (VI-VIII). General synthesis method. To a mixture of 0.1 mol of formaldehyde (II) and 0.1 mol of cyclohexanol (I) in benzene, add 0.1 mol of secondary amine (III-V) dropwise at 20-220C with stirring. Stirring was continued for 4-5 h at a temperature of 78-800C. After cooling, the mixture was washed with 10% ammonia solution, then with distilled water until neutral and dried over anhydrous MgSO4. After distilling off benzene, the residue was distilled in vacuo.
Piperidinomethoxycyclohexane (VI) was obtained from 10 g (0.1 mol) of cyclohexanol, 3.0 g (0.1 mol) of formaldehyde, and 8.5 g (0.1 mol) of piperidine (III). The yield of the compound was 14.5 g (73%), b.p. 96-990C (3 mm Hg), n20 1.4774, df 0.9423 g/sm3. IR spectrum, v, cm-1: 776, 853 (C-H, CH2 mathematical vibrations), 1036, 1071, 1130, 1154 (C-O-C), 1023, 1232 (C-N), 1312, 1348, 1366, 1412, 1448, 2852, 2927 (5 C-H, CH, CH2, CH3). 1H NMR spectrum, 5, ppm: 1.2-1.65 m (16H, 8CH2), 2.5-2.63 m (4H, CH2-N-CH2), 4.05 d.d (1H, OCH), 4.20 d (2H, OCH2N, J 10.5 Hz). 13C NMR spectrum, 5, ppm: 24.15, 24.18, 25.47, 25.85, 32.52, 35.55, 50.60, 53.03, 69.89, 74.91 (2C), 88.31. Mass spectrum, m/z (Ire., %): 198(10) [M+H]+, 197(9) [M]+, 180(8) [M-OH]+, 165(11) [M-H2O-CH2]+, 114(100) [M-C5H9NK 96(13) [M-C5H9N-H2O]+, 81(5), 70(20), 42(6). Found, %: C 74.03; H 11.04; No. 6.94. C12H23NO. Calculated, %: C 73.04; H 11.75; N 7.10. M 197.18.
Morpholinomethoxycyclohexane (VII) was obtained from 10 g (0.1 mol) of cyc-
lohexanol, 3.0 g (0.1 mol) of formaldehyde, and 8.7 g (0.1 mol) of morpholine (IV). The yield of the compound was 13.8 g (69%), b.p. 1120C (6 mm Hg), n 201.479, d f 1.0061 g/sm3. IR spectrum, v, cm-1: 864, 902 (C-H, CH2 mathematical vibrations), 1016, 1070, 1150 (C-O-C), 1016, 1232 (C-N), 1257, 1281 (C- O-C cycle), 1313, 1360, 1411, 1450, 2851, 2927 (5 C-H, CH, CH2, CH3). 1H NMR spectrum, 5, ppm: 1.2-1.66 m (10H, 5CH2), 2.45-2.66 m (4H, CH2-N-CH2), 3.55-3.80 m (4H, CH2OCH2 cycle), 4.01 d. d (1H, OCH), 4.7 d.d (2H, OCH2N, J 2.5, J 6.4 Hz). 13C NMR spectrum, 5, ppm: 24.15, 26.4, 28.80, 30.50, 32.3, 52.4, 55.6 (2C), 66.7, 76.0, 84.10. Mass-spectrum, m/z (ire/., %): 200(8) [M+H]+, 199(7) [M]+, 182(13)
[M-OH]+, 168(20) [ M-OH-CH2]+, 131(21)
[M-C4H8N]+, 100(10) [M-C5HNO]+, 74(100) [M-C7H7O-H2O] , 95(25), 75( 54). Found, %: C 67.03; H 10.14; N 7.34. C11H21NO2. Calculated, %: C 66.29; H 10.62; N 7.03.M 199.16.
Hexamethyleneiminomethoxycyclohex ane (VIII) was obtained from 10 g (0.1 mol) of cyclohexanol, 3.0 g (0.1 mol) of formaldehyde, and 9.9 g (0.1 mol) of hexamethyleneimine (V). The yield of the compound was 15.9 g (75%), b.p. 1090C (2 mm Hg), n 2° 1.485, d f 0.9478 g/sm3. IR spectrum, v, cm-1: 887, 944, 984 (CH, CH2 mathematical vibrations), 1035, 1070, 1134 (C-O-C), 1023, 1183, 1236 (C-N), 1341, 1357, 1411, 1451, 2850, 2920 (5 C-H, CH, CH2, CH3). 1H NMR spectrum, 5, ppm: 1.151.78 m (18H, 9CH2), 2.63-2.78 m (4H, CH2-N-CH2), 4.14 d.d (1H, OCH), 4.7 d.d ( 2H, OCH2N, J 2.5, J 6.4 Hz). 13C NMR spectrum, 5, ppm: 24.4, 27.32, 27.54, 28.20, 28.75, 29.24, 29.45, 32.1, 52.41, 53.32 (2C), 76.0, 83.17. Mass-spectrum, m/z (Ire/, %): 211(11) [M]+, 194(12) [M-OH]+, 180(21) [M-OH-CH2]+, 128(17 ) [M-C5HN]+, 113(51) [M-C6H10O]+, 99(31) [C6HuO]+, 92(100) [CyHyO]+, 74(27) [M-C7H7O-H2O] , 81(6), 42(6). Found, %: C 73.03; H 12.14; N 7.04. C13H25NO. Calculated, %: C 73.88; H 11.92; No. 6.63.M211.19.
Conclusions
Three-component Mannich reaction of cyclohexanol, formaldehyde and cyclic amines
was used to obtain aminomethoxy derivatives of cyclohexanol. The reaction was carried out at a temperature of 78-800C for 4-5 h in a benzene solution at an equimolar ratio of the starting components. The yield of compounds was 6975%. Their physicochemical properties were determined, and the composition and structure of the obtained compounds were confirmed using the data of elemental analysis, IR, 1Н, 13С NMR spectroscopy and mass spectrometry.
The effect of the synthesized compounds on SRBs of the "Desulfovibrio desulfuricans" type was tested at three concentrations (25, 50, 100 mg/l). Based on the amount of hydrogen sulfide formed, the bactericidal effect of the presented samples was calculated. It has been established that 1% solutions of aminomethoxy derivatives of cyclohexanol exhibit high bactericidal activity, and they act on bacteria at very low concentrations compared to the industrially used bactericide-inhibitors AMDOR IK-7 and AMDOR IK-10 taken as a standard.
Acknowledgments
The work was performed based on agreement No 1/18 dated April 12, 2018 on scientific and technical cooperation between the Institute of Organoelement Compounds named after academician A.N.Nesmeyanov RAS and the Institute of Petrochemical Processes named after academician Yu.H.Mammadaliyev National Academy of Sciences of Azerbaijan. The work was financed by the state budget.
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TSÍKLOHEKSANOLUN AMÍNOMETOKSÍ TOROMOLORÍNÍN SÍNTEZÍ УЭ ÍNHÍBÍTOR-BAKTERISÍD XASSЭLЭRlNiN ÖYRЭNiLMЭSi
S.V.ismayilova, E.H-Mammadbayli, K.A.Kofetkov, G.Э.Haclyeva, L.M.Maharramova, D.B.Agamaliyeva
Tsikloheksanol, tsiklik aminlar (piperidin, morfolin, heksametilenimin) va formaldehid asasinda yeni Mannix asaslari sintez olunmu§dur. Reaksiya 78-800С temperaturda 4-5 saat müddatinda, ilkin maddalarin ekvimolyar nisbatinda benzol mahlulunda apanlmi§dir. Birla§malarin giximi 69-75%-dir. Sintez olunmu§ birla§malarin fiziki-kimyavi gösta-ricilari tayin edilmi§dir. Maqsadli mahsullarin tarkib va qurulu§u element analizi, ÍQ, :Н va 13С NMR spektroskopiya, elaca da kütla spektrometriya üsullari ila tasdiqlanmi§dir. Onlarin üg qatiliqda (25; 50; 100 mq/l) "Desulfovibrio desulfuricans" tipli sulfatreduksiyaedici bakteriyalarin hayat faaliyyatina tasiri yoxlanilmi§dir. Alinmi§ birla§malar yüksak bakterisid xassa göstarmi§dir, bu birla§malarin izopropil spirtinda 1%-li mahlullari 100 mq/l qatiliqda 100% bakterisid tasir göstarmi§dilar. Morfolin fraqmentli birla§manin 1%-li mahlulu artiq 50 mq/l qatiliqda 100% bakterisid tasir göstarir. Piperidin va heksametilenimin fraqmenti saxlayan birla§malar50 mq/l qatiliqda müvafiq olaraq 96.2 va 98% bakterisid tasir göstarmi§dir. 25 mq/l qatiliqda isa har üg birla§manin bakterisid tasiri müvafiq olaraq 16.4%, 36.4% va 58.2% ta§kil etmi§dir. Alinmi§ naticalar göstarir ki, sintez edilmi§ birla§malar sanayeda istifada olunan standart olaraq qabul edilan АМДОР ИК-7 va АМДОР ИК-10 bakterisid inhibitorlari ila müqayisada daha gox bakterisid xüsusiyyatlar göstarmi§dir. Tsikloheksanolun aminometoksi töramalarinin gox a§agi qatiliqlarda bakteriyalara tasirini nazara alaraq, onlar sulfatreduksiyaedici bakteriyalara qar§i effektli inhibitor kimi taklif edila bilar.
Agar sözlar: tsikloheksanol, ikili aminlar, Mannix asaslari, sulfatreduksiyaedici bakteriyalar, inhibitor-bakterisidlik, biokorroziya.
СИНТЕЗ АМИНОМЕТОКСИПРОИЗВОДНЫХ ЦИКЛОГЕКСАНОЛА И ИЗУЧЕНИЕ ИХ В КАЧЕСТВЕ ИНГИБИТОР-БАКТЕРИЦИДОВ
С.В.Исмайылова, Э.Г.Мамедбейли, К.А.Кочетков, Г.Э.Гаджиева, Л.М.Магеррамова, Д.Б.Агамалиева
На основе циклогексанола, циклических аминов (пиперидин, морфолин, гексаметиленимин) и формальдегида синтезированы новые основания Манниха. Реакцию проводили при температуре 78-800С в течение 4-5 ч, в растворе бензола при эквимольном соотношении исходных компонентов. Выход соединений составил 69-75%. Определены физико-химические данные синтезированных соединений. Состав и строение целевых продуктов подтверждены методами элементного анализа, ИК, 1Н и 13С ЯМР спектроскопии, а также масс-спектрометрии. Исследовано влияние их на жизнедеятельность сульфатвосстанавливающих бактерий типа "Desulfovibrio desulfuricans" в трех концентрациях (25; 50; 100 мг/л). Полученные соединения проявили высокие бактерицидные свойства, 1%-ые растворы этих соединений в изопропиловом спирте при концентрации 100 мг/л проявили 100%-ный бактерицидный эффект. 1%-ный раствор соединения с фрагментом морфолина уже при концентрации 50 мг/л проявляет 100%-ный бактерицидный эффект. Соединения с фрагментом пиперидина и гексаметиленимина при концентрации 50 мг/л проявили 96.2 и 98%-ный бактерицидный эффект, соответственно. А при концентрации 25 мг/л бактерицидный эффект всех трех соединений составил 16.4%, 36.4% и 58.2%, соответственно. По полученным результатам видно, что синтезированные соединения проявили более бактерицидные свойства по сравнению с взятыми в качестве эталона промышленно используемыми бактерицид-ингибиторами АМДОР ИК-7 и АМДОР ИК-10. Учитывая то, что указанные аминометокси-производные циклогексанола влияют на бактерии при очень низких концентрациях, их можно предложить в качестве эффективных ингибиторов против сульфатвосстанавливающих бактерий.
Ключевые слова: циклогексанол, вторичные амины, основания Манниха, сульфатвосстанавливающие бактерии, ингибитор-бактерициды, биокоррозия.
