Uzbek Chemical Journal

VOLUME NR5

PHYSICAL CHEMISTRY

 

UDK 541.13; 547.551.5; 661.728.892;544.72

L. M. Kurbanova, N. B. Eshmamatova, X. I. Akbarov, E. T. Berdimurodov

PHYSICAL AND CHEMICAL PROPERTIES OF CARBON STEEL CORROSION INHIBITORS BASED ON SODIUM CARBOXYMETHYL CELLULOSE AND PHOSPHORUS COMPOUNDS

National University of Uzbekistan named after MirzoUlugbek, E- mail: Eshmamatova79@mail.ru

Abstract. Background. The creation of new effective corrosion inhibitors for structural grades of carbon steel is an urgent problem. In the area of achieving import substitution of this type of metal protection products, certain results have been achieved.

Purpose. Creation and study of the properties of new inhibitors based on sodium carboxymethylcellulose and phosphorus-containing compounds.

Methodology. Electrochemical (Corrtest: Potentiostat/Galvanostat), gravimetric, IR spectroscopic (IR spectrometer EN 1407) and X-ray phase (DRON-05) methods were used.

Originality. For the first time, phosphorus-containing derivatives of sodium carboxymethylcellulose, diethylamine and aniline were used to create inhibitors, and a mechanism for their protective action was proposed.

Findings. Sodium carboxymethylcellulose and phosphorus-containing corrosion inhibitors were synthesized and their properties were studied by physicochemical methods.

Key words: corrosion, carbon steel, inhibitor, sodium carboxymethylcellulose, aniline, diethylamine, phosphoric acid, sodium tripolyphosphate.

Highlights:

- synthesis of carbon steel corrosion inhibitors;

- synthesis component: sodium carboxymethylcellulose and amines,

- synthesis component: phosphorus-containing compounds;

- the structure of the products was revealed by physical chemistry methods;

- a mechanism for their inhibition of the steel surface is proposed.

References

1. Semikhina L.P., Moskvina E.N., Kolchevskaya I.V. The phenomenon of synergism in mixtures of surface substances // Bulletin of Tyumen State University. Socio-economic and legal research. - Tyumen. –Vol. 5. -2012. –P.90-91. (in Russian)

2. Zhao Y. Scale inhibition performance of sodium carboxymethyl cellulose on heat transfer surface at various temperatures: Experiments and molecular dynamics simulation // International Journal of Heat and Mass Transfer. –2019. -T.141. – pp. 457-463.

3. KholikovA.Zh. Protection of carbon steel by various inhibitors in simulated formation water // Current problems of the humanities and natural sciences. -2013. – No.11-1. – P. 52-53. (in Russian)

4. Khaidarova G.R. Corrosion inhibitors for the protection of oilfield equipment // Modern problems of science and education: electron. scientific journal.-2014.-No.6.-URL:http://www.scienceeducation.ru/pdf/2014/6/1460.pdf.  (in Russian)

5. Eshmamatova N.B., AkbarovKh.I. Metal corrosion inhibitors based on hexamethylenediamine monophosphate // Composite materials. -2013.–No. 2. – pp. 41-43. (in Russian)

6. Eshmamatova N.B., AkbarovKh.I. Study of the effectiveness of oligomeric metal corrosion inhibitors based on various nitrogen-containing organic compounds and phosphoric acid // Reports of the Academy of Sciences of the Republic of Uzbekistan. -2014. –No. 2. – P. 47-51. (in Russian)

7. Eshmamatova N.B., Kurbanova L.M., Akbarov H.I., Azimov L.A. Physicist-chemical properties of inhibitors based on organic amines and chrome compounds // Monograph. Publishing house "Lesson press". -2022. -142 p. (in Uzbek)

8. Fakhretdinov P.S., Borisov D.N., Romanov G.V., KhodyrevYu.P., Galiakberov R.M. Corrosion inhibitors from a number of ammonium compounds based on α-olefins // Kazan Scientific Center of the Russian Academy of Sciences. Oil and gas business. – 2008. –P. 1-18. (in Russian)

9. Kurbanov F.K. Research and development of high-temperature corrosion inhibitors based on acetylene compounds: Author's abstract. doc. chem. Sci. –M.: MoscowStateUniversity. –1989. -21 p.(in Russian)

10. Damaskin B.B., Petriy O.A. and others. Workshop on electrochemistry. -M.: Higher School, 1991.-288 pp. (in Russian)

11. Savenkov L.G., Sotskaya N.V., Kravchenko T.A., Surova L.N., Sleptsova O.V., Kichigin V.P. Corrosion of carbon steel in recycled water with a high content and selection of inhibitory compositions // Zhur. Prik. chem. -1991. – No. 2. –P. 313-317. (in Russian)

12. Afanasyev A.V. Increasing the effectiveness of inhibitor protection of field pipelines by updating system processes. Experience in the use of corrosion inhibitors // Engineering practice: production-technical. oil and gas magazine -2012. –No. 5. –P.34-42. URL: http://glavteh.ru/files/IP-5_Afanasiev.pdf. (in Russian)

To cite this article:L. M. Kurbanova, N. B. Eshmamatova, X. I. Akbarov, E. T. Berdimurodov. Physical and chemical properties of carbon steel corrosion inhibitors based on sodium carboxymethyl cellulose and phosphorus compounds // Uzbek chemical journal. -2023. – Nr5. - Pp.3-10. 

Received: 28.10.2023; Accepted:06.11.2023; Published: 26.12.2023

 

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UDK 661.876.7

U. R. Ernazarov, A. I. Asadov, S. N. Rasulova, V. P. Guro, M. A. Ibragimova, Z. A. Nabiyeva

CLEANING OF PRODUCT RHENIUM-CONTAINING SOLUTION FROM ORGANIC IMPURITIES BY MEAN OF OZONATION (Part 1)

Institute of General and Inorganic Chemistry of the Academy of Sciences of the Republic of Uzbekistan

Abstract.Background. At Almalyk MMC JSC, during the production of industrial molybdenum cinder (MPC), rhenium is captured on SIM 202 Purolite resin. The regulations for its operation provide for the cleaning of organic matter with a technological solution.

Purpose: to develop a method for purifying a rhenium-containing production solution from organic impurities by ozonizing it.

Methodology. Process solutions were monitored by elemental analysis (Agilent 7500 IСP-MS), X-ray fluorescence (RigakuNEXCGEDXRFAnalyzer), IR spectroscopic (PYE NiCAM and IR-Fourier Nicolet iS50, ThermoScientific, 700-3600 cm-1).

Originality. The applicability, without harm to the SIM 202 Purolite sorbent, of ozonation when cleaning a process solution from organic contaminants, instead of the potassium permanganate reagent, is substantiated.

Findings. Data on the elemental composition and IR characteristics of solutions of sorption concentration of rhenium ions were obtained.

Key words: ozone, oxidation, organic impurities, rhenium, adsorbent SIM 202 Purolite.

Highlights:

- sorption of Re(VII) ions on SIM 202 Purolite resin;

- oxidation of process solution components with ozone.

References

1. Akhmanov M. The water we drink. -St. Petersburg: NevskyProspekt, 2002. -152 p.(in Russian)

2. Koganovsky A.M., Klimenko N.A. et al. Treatment and use of waste water in industrial water supply. – M.: Chemistry, 1983. -288 p.(in Russian)

3. Meshalkin A.V., Dmitrieva T.V., Strizhko L.S. Ecochemical workshop. Ed. A.P. Korzhavoy. – M.: SCIENCE-PRESS, 2002. – 240 p.(in Russian)

4. Frog B.N., Levchenko A.P. Water treatment. -M.: IMGU, 1996. -198 p.(in Russian)

5. FrolovYu.G. Colloid chemistry course. -M.: Alliance, 2004. -221 p.(in Russian)

6. Shchukin E.D., Pertsov A.V., Amelina E.A. Colloidal chemistry.-M.: Higher School, 2004.-356 p.(in Russian)

7. Instructions for monitoring the disinfection of drinking water and disinfection of water supply facilities with chlorine for centralized and local water supply. - M.: Ministry of Health of the USSR, 1969.(in Russian)

8. Rules for the technical operation of water supply and sanitation systems in populated areas. - M.: Stroyizdat, 1979. -39 p.(in Russian)

9. Miro S. AAlejandre, A Fortuny, S Bengoa, J Font, A Fabregat Aqueous phase catalytic oxidation of phenol in a trickle bed reactor: effect of the pH / C. Miro, A.

10. Alejandre, A. Fortuny, C. Bengoa, J. Font, A. Fabregat. Water Research. - 1999. - V. 33.-No. 4.-P. 1005-1013.(in Russian)

11. Shevchenko M.A. Ozonation reactions in aqueous solutions / M.A. Shevchenko, V.V. Goncharuk. - M.: Nauka, 1987. - 322 p.(in Russian)

12. Cano Quiroz. Wastewater ozonation catalyzed by iron anaid / Cano Quiroz, Carlos Barrera-Diaz, Gabriela Roa-Morales, Patricia Balderas Hernandez, Rubi Romero, Reyna Natividad // Ind. Eng. Chem. Res. - 2011. - No50. - P. 2488-2494

To cite this article:U. R. Ernazarov, A. I. Asadov, S. N. Rasulova, V. P. Guro, M. A. Ibragimova, Z. A. Nabiyeva. Cleaning of product rhenium-containing solution from organic impurities by mean of ozonation (Part 1) // Uzbek chemical journal. -2023. – Nr5. - Pp.10-15. 

Received: 24.11.2023; Accepted:17.12.2023; Published: 26.12.2023

 

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INORGANIC CHEMISTRY

 

УДК 539.261+ 661.744.14

1S. М. Mukhammadiev, 1,2S. S. Muradov, 2S. B. Rajabov, 3J. M. Ashurov,1,2SH. SH. Daminova

SYNTHESIS, CRYSTAL STRUCTURE, HIRSHFELD SURFACE AND VOID ANALYSIS OF 2-AMINO-1H-BENZIMIDAZOLIUM 2-HYDROXYBENZOATE

1Uzbekistan Japan Innovation Center of Youth”, University Street 2B, Tashkent 100095, Uzbekistan, 2National University of Uzbekistan named after MirzoUlugbek, University Street 4, Tashkent 100174, Uzbekistan, 3Institute of Bioorganic Chemistry of the Academy of Sciences of the Republic of Uzbekistan, st. M. Ulugbek, 83, Tashkent 700125, Uzbekistan salmonmuxammadiyev97@gmail.com

Abstract. Background.  Data on the crystal structure of compounds do not yet provide insight into the relationship between structure and properties. However, the method of crystal chemical analysis, including the Hirschfeld surface and void analysis in the description of molecules, will help correct the situation.

Purpose. To test the applicability of the Hirschfeld surface and void analysis in the study of intermolecular interactions in a crystal structure, using the example of the compound 2-amino-1H-benzimidazolium 2-hydroxybenzoate.

Methodology. X-ray diffraction analysis, Hirschfeld surface analysis, fingerprint diagrams, void analysis.

Originality. A new compound was obtained and studied in the reaction of 2-aminobenzimidazole with hydroxybenzoic acid.

Findings.It was shown that the asymmetric unit of the molecule contains centrosymmetric benzimidazolium cations and salicylic anions that link imidazole fragments with the oxygen atoms of neighboring anions. In the structure of the benzimidazole molecule, the N-H groups form strong hydrogen bonds with the oxygen atoms of the carboxyl group of the hydroxybenzoate anion; in the structure, H∙∙∙H (46.7%) and H∙∙∙C/C∙∙∙H (19.6%) are significant; π–π stacking interactions are observed; the volume of voids in the package is 100.83 Å.

Key words: 2-aminobenzimidazole, 2-hydroxybenzoate, crystal structure, Hirschfeld surface, void analysis.

Highlights:

- procedure for the synthesis of 2-amino-1H-benzimidazolium 2-hydroxybenzoate;

- structure of 2-amino-1H-benzimidazolium 2-hydroxybenzoate;

- Hirschfeld surface analysis.

References

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4.   Dvornikova, I. A., Buravlev, E. V., Fedorova, I. V., Shevchenko, O. G., Chukicheva, I. Y., &Kutchin, A. V. Synthesis and antioxidant properties of benzimidazole derivatives with isobornylphenol fragments //Russian Chemical Bulletin. – 2019. – V. 68. – N 5. – P. 1000-1005. doi.org/10.1007/s11172-019-2510-7.

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28. Low, J. N., Cobo, J., Abonia, R., Insuasty, B., &Glidewell, C. 2-Aminobenzimidazolium O-ethyl malonate: eight independent N—H⋯ O hydrogen bonds generate sheets //ActaCrystallographica Section C: Crystal Structure Communications. – 2003. – V. 59. – N. 12. – P. 669-671. doi.org/10.1107/S0108270103023333

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33. Ashfaq, M., Tahir, M. N., Muhammad, S., Munawar, K. S., Ali, A., Bogdanov, G., &Alarfaji, S. S. Single-crystal investigation, Hirshfeld surface analysis, and DFT study of third-order NLO properties of unsymmetrical acyl thiourea derivatives //ACS omega. – 2021. – V. 6. – N. 46. – P. 31211-31225. doi.org/10.1021/acsomega.1c04884

34. Spackman M. A. et al. Fingerprinting intermolecular interactions in molecular crystals //CrystEngComm. – 2002. – V. 4. – N. 66. – P. 378-392.

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36. Kargar, H., Fallah-Mehrjardi, M., Behjatmanesh-Ardakani, R., Munawar, K. S., Ashfaq, M., & Tahir, M. N. Diverse coordination of isoniazid hydrazone Schiff base ligand towards iron (III): Synthesis, characterization, SC-XRD, HSA, QTAIM, MEP, NCI, NBO and DFT study //Journal of Molecular Structure. – 2022. – V. 1250. – P. 131691. doi.org/10.1016/j.molstruc.2021.131691

To cite this article:S. М. Mukhammadiev, S. S. Muradov, S. B. Rajabov, J. M. Ashurov, SH. SH. Daminova. Synthesis, crystal structure, hirshfeld surface and void analysis of 2-amino-1h-benzimidazolium 2-hydroxybenzoate// Uzbek chemical journal. -2023. – Nr5. - Pp.15-24. 

Received: 23.10.2023; Accepted:24.11.2023; Published: 26.12.2023

 

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UDC 544.123

ZH. S. Shukurov

STUDY OF THE INTERACTION OF CALCIUM AND MAGNESIUM CHLORIDE, AMMONIA AND WATER COMPONENTS IN SOLUTION

Institute of General and Inorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170 Uzbekistan *Е-mail:jamshidshukurov84@gmail.com

Abstract.Background. The interaction of calcium and magnesium chlorides with ammonia solution during the isolation of salts from a solution of calcium and magnesium chlorides by the polythermal method in a wide range of temperatures and concentrations has not been previously considered.

Purpose. Study of the polythermal solubility of CaCl2∙2H2O–[25%NH3+75%H2O]-H2O andMgCl2∙6H2O–[25%NH3+75%H2O]-H2Osystems in a wide range of temperatures and concentrations.

Methodology. The visual-polythermal method was used, ammonia was determined by the Keldahl method, chloride ions - by the Mohr method.

Originality. A polythermal solubility diagram has been constructed for the systems CaCl2∙2H2O–[25%NH3+75%H2O]-H2O andMgCl2∙6H2O–[25%NH3+75%H2O]-H2O over a wide range of temperatures and concentrations.

Findings. The diagram of the CaCl2∙2H2O–[25%NH3+75%H2O]-H2O system was constructed by drawing six internal sections in the temperature range from -49.7 to 45.2oC, and MgCl2∙6H2O–[25%NH3+75%H2O]-H2O - by making seven internal cuts in the temperature range from -36.0 to 40.0°C. The boundaries of the crystallization fields of ice, 6 aqueous magnesium chloride, 12 aqueous magnesium chloride and the double salt of magnesium hydroxychloride and ammonium chloride were determined.

Key words: two-aqueous calcium chloride, six-aqueous magnesium chloride, solubility diagram, crystallization temperature.

Highlights:

- system CaCl2∙2H2O–[25%NH3+75%H2O]-H2O, solubility diagram;

- system MgCl2∙6H2O–[25%NH3+75%H2O]-H2O, at temperature: 36.0-40.0°C.

References

1.Decision No. PQ-4992 dated February 13, 2021 "On further reform and financial consolidation of chemical industry enterprises, and measures to develop the production of chemical products with high added value." (in Uzbek)

2.   Method for producing magnesium oxide from natural brines. Russian patent 2003 RU 2211803 C2. Invention according to MCP C01F5/06 (in Russian)

3.   Wu. Lan’er, Han. Fenglan, Liu. Guiqun (2021), "Magnesium Smelting via the Pidgeon Process",Comprehensive Utilization of Magnesium Slag by Pidgeon Process, Singapore: Springer Singapore, pp.45–68, doi:10.1007/978-981-16-2171-0_2, ISBN978-981-16-2173-4, S2CID  235872413,  retrieved 2023-04-16

4. Wu. Lan'er (2021). Comprehensive utilization of magnesium slag by pidgeon process. Fenglan Han, Guiqun Liu. Singapore. ISBN 978-981-16-2171-0. OCLC 1249509843.

5.Brooks Geoffrey, Trang Simon, Witt Peter, Khan M. N. H., Nagle Michael (May 2006). "The carbothermic route to magnesium". JOM. 58 (5): 51–55. doi:10.1007/s11837-006-0024-x. ISSN 1047-4838.

6.Khamrakulov Z.A., Askarova M.K., Tukhtaev S. Prepation of calcium-magnesium chlorate defoliant from dolomite.// Journal of Chemical Technology and Metallurgy. - Sofia, - 2015. – Vol. 50, ISSN 1. - P. 65-70.

7.Khamrakulov Z.A. Study of the mutual influence of components in systems that justify the process of obtaining a new defoliant. // Uzbek Chemical Journal. - Tashkent, 2015. - No. 3. – P. 24-30. (in Russian)

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10. GOST 4209-77. Magnesium chloride 6-water. Technical conditions. // -M.: Standards Publishing House, 1977. N 2079. (in Russian)

11. Trunin A.S. Petrova D.G. Visual-polythermic method / Kuibyshev Polytechnic. Ins. - Kuibyshev. 1977.-94s./ Dep. in VINITI No. 584-78. (in Russian)

12. Kreshkov A.P. Fundamentals of analytical chemistry. In 2 volumes. M.: Chemistry.1965. T. 2. 376 p. (in Russian)

13. Schwarzenbach G., Flashka G. Complexometrictitration.// M.: Khimiya, 1970. (in Russian)

14. Vinnik M.M. and others. Methods for analyzing phosphate raw materials, phosphorus and complex fertilizers, feed phosphates. – M., 1975. – 218 p. (in Russian)

To cite this article:ZH. S. Shukurov. Study of the interaction of calcium and magnesium chloride, ammonia and water components in solution// Uzbek chemical journal. -2023. – Nr5. - Pp.24-29. 

Received: 25.10.2023; Accepted: 22.11.2023; Published: 26.12.2023

 

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UDK 669.712.2-669.76;  543.872

1Z. B. Rakhimdzhonov, 1A. I. Asadov, 1U. N. Ruziev, 2S. N. Rasulova, 2V. P. Guro, 2M. A. Ibragimova

TECHNOGENIC RAW MATERIALS FOR MOLYBDENUM PRODUCTION OF ALMALYK MMC

1JSC "Almalyk MMC", 2Institute of General and Inorganic Chemistry of the Academy of Sciences of the Republic of Uzbekistan

Abstract. Background. Previously, in the production of molybdenum NPO PRMiTS JSC "Almalyk MMC" nitrate opening of molybdenite concentrate was used, later replaced by roasting and ammonia-soda leaching of molybdenum middling product cinder. Therefore, sludge accumulation cards, where non-returnable cakes are stored, contain Mo, Re, Cu, Au. Involving this technogenic raw material in the production, in addition to expanding the raw material base, will solve the problem of the category of land occupied by sludge.

Purpose: todevelop a technology for processing molybdenum production sludge.

Methodology. A plant for leaching Mo-containing cakes was used. Analysis of Mo(VI), Au(III), Cu(II) ions was performed on an Agilent 7500 IСP spectrometer. Active chlorine NaClO was determined according to GOST 18190-72.

Originality. The introduction of Mo(VI), Au(III), Cu(II) compounds during soda and hypochlorite leaching of Mocake is considered

Findings. The kinetics of leaching of Mo-cake components with soda ash and hypochlorite ions in acidic and alkaline environments has been studied.

Key words: molybdenum, rhenium, copper, waste, leaching, extraction.

Highlights:

- introduction of Mo(VI), Au(III), Cu(II) compounds in acidic and alkaline media;

- parameters of the Mocake leaching process were calculated;

- regulations for the processing of technogenic raw materials have been developed.

References

1. Zelikman A.N. Metallurgy of refractory rare metals.-M.: Metallurgy, 1986.- 439 p. (in Russian)

2. Blokhin A.A. Chemistry and technology of molybdenum, tungsten and rhenium. Text of lectures. – St. Petersburg: Publishing house. VKhTI, 1999. – 94 p. (in Russian)

3. Ts 00193950-074:2018. Cinder of molybdenum industrial product. Uzstandard. -2018. (in Russian)

4. Potashnikov Yu.M., Lutsik V.I., Chursanov Yu.V. Study of the interaction of molybdenite with nitric acid. // News of universities. Non-ferrous metallurgy. – 1984. – No. 1. – P. 57-61. (in Russian)

5. Nikitina JI.C. Decomposition of molybdenite products with nitric acid. //Non-ferrous metals.-1983. -No. 4.-S. 63-67(in Russian)

6. TI 00193950-71-04-013:2019 to replace TI 12810-5-1:2008 Technological instructions for the production of molybdenum salts (tetramolybdate and ammonium paramolybdate). (in Russian)

7. Milusheva M.A. and others. Extraction of molybdenum and rhenium from solutions of nitric sulfate leaching of molybdenum concentrates. // “Complex use of mineral raw materials.” -1986. -No. 11. -P.53-55. (in Russian)

8. Polant A.A., Troshkina I.D., Chekmarev A.M. Metallurgy of rhenium. -M.: Nauka, 2007. - 298 p. (in Russian)

9. RF Patent No. 2117709. Method of oxidative autoclave leaching of polymetallic ferrosulfide materials containing precious metals. Korsunsky V.I., Timoshenko E.M., Naftal M.N. and others. Appl. 1997-10-13; publ.: 08.20.1998. -P.1-11. (in Russian)

10. Extraction of molybdenum from sulfide ore with an alkaline solution of sodium hypochlorite / V.I. Lutsik, Yu.M. Potashnikov, V.A. Lutsik et al. // Izv. Sib. dept. Academy of Sciences of the USSR. Ser. chem. Sci. - T. 4. - 1985. - No. 11. – P. 49-54. (in Russian)

11. Dauletbakov T.S., Smagulov M.O., Amirkhan A.A. Extraction of gold from cakes from leaching of gold-arsenic concentrate. //Bulletin of the Kazakh National Technical University named after. K. I. Satpayeva, ISSN 1680-9211.-2011. -Almaty. Abstract database of scientific journals. MRNTI: 01/53/05. -P. 5270. (in Russian)

12. Roman D. Allabergenov, Vitaliy P. Guro, Sitorabonu N. Rasulova, Edgor T. Safarov, Khayitali F. Adinayev. Regulations of oxidation of rhenium heptasulphide at rhenium concentrate processing // Journal of Chemical Technology and Metallurgy. -56, 6. -2021.-Pp. 1279-1284.

13. Allabergenov R.D., SharipovKh.T., SharipovR.Kh., Niyazmatov A.A. Possibilities of oxidative lixiviation of rhenium sulphides by low pressures (Рений: закономерности окислительного выщелачивания солей рения).//7th International Symposium on Technetium and rhenium – Science and Utilization. Book of absracts. -July 4-8 2011. -Moscow. -120 p.

14. KushakbaevA., TokhtashevG., AkhmedovK. and etc. Precipitation of molybdenum with melamine from rhenium-containing acidic solutions / Manuscript dep. in ONIITEKHIM. - Cherkassy. 04/06/1988. - N.344-hp. (in Russian)

15. A.s. 338549 (USSR, 1970). A method for purifying acidic solutions of molybdenum from iron / Dyusebekov B. et al. - Publ. in B.I., 1970, No. 16. (in Russian)

16. Anfilogova L.A. and others. Purification of ammonium molybdate solutions from copper and nickel. - In the book: Scientific Tr. Institute "Sibtsvetmetkiiproekt", issue 1, 1971. - 260 p. (in Russian)

To cite this article: ZH. Z. B. Rakhimdzhonov, A. I. Asadov, U. N. Ruziev, S. N. Rasulova, V. P. Guro, M. A. Ibragimova. Technogenic raw materials for molybdenum production of Almalyk MMC // Uzbek chemical journal. -2023. – Nr5. - Pp.29-36. 

Received: 24.11.2023; Accepted: 07.12.2023; Published: 26.12.2023

 

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ORGANIC CHEMISTRY

 

UDK 547.856.1.

R. Z. Khudaykulova, G. N. Kudratov, I. S. Ortikov,  K. K. Turgunov, B. Zh. Elmuradov

SYNTHESIS AND REACTIONS OF NUCLEOPHILIC SUBSTITUTION OF 2,4-DICHLORO-6H-(BROMINE) QUINAZOLINES

Institute of Chemistry of Plant Substances of the Academy of Sciences of the Republic of Uzbekistan

Abstract. Background. It is known that bi- and tricyclic quinazoline derivatives are isolated from the PeganiumHarmala plant, which has high biological activity. The synthesis and study of compounds based on 2,4-dichloroquinazoline is relevant.

Purpose: Synthesis of 6-H (bromo)-2,4-dichloroquinazolines based on 6-H (bromo)-quinazoline-2,4-diones, water-soluble hydrochloride salts, their structure using physical research methods.

Methodology. As a result of the reaction of 6H (bromo)quinazoline-2,4-diones with chlorinating agents (POCl3+PCl5), products were obtained in a nucleophilic substitution reaction with secondary cyclic amines. Their structure was proven by IR and 1H NMR spectroscopy.

Originality. As a result of nucleophilic substitution, new quinazoline derivatives, water-soluble hydrochloride salts, were obtained.

Findings. 2,4-Dichloro-6H(bromo) quinazolines were also synthesized from cyclic secondary amines by nucleophilic substitution with morpholine and piperidine.

Key words: 2,4-dichloro-6H(bromo)quinazoline, morpholine, 2,4-di(piperidin-1-yl)quinazoline, 4,4`-(6-bromoquinazoline-2,4-diyl)dimorpholine, reactions nucleophilic substitution.

Highlights:

- cyclization of anthranilic, 5-bromanthranilic acids with formamide;

- chlorination of the resulting quinazoline-2,4-dione;

- 2,4-dichloro-6H(bromo)quinazolines were synthesized;

- nucleophilic substitution reaction with piperidine and morpholine;

- synthesis of 6H(bromo)-2,4-disubstituted quinazoline derivatives;

- salts of water-soluble quinazoline derivatives.

References

1.   Connolly D.J., Cusack D., O’Sullivan T. P., and Guiry P. J., “Synthesis of quinazolinones and quinazolines” //Tetrahedron. -2005. -vol. 61. -P. 10153–10202.

2.   Grover G., Kini S.G. Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents // European Journal of Medicinal Chemistry. -2006. -vol. 41. -P. 256-262.

3.   Verhaeghe P., Azas N., Gasquet M., Hutter S., Ducros C., Laget M., et al. Synthesis and antiplasmodial activity of new 4-aryl-2-trichloromethyl quinazolines // Bioorganic & Medicinal Chemistry Letters. -2008. -vol. 18. -P. 396-401.

4.   Georgey H., Abdel Gawad N., Abbas S. Synthesis and anticonvulsant activity of some quinazolin-4-(3H)-one derivatives // Molecules. -2008. -vol. 13. -P. 2557-2569.

5.   Malamas M.S., Millen J. Quinazoline acetic acids and related analogues as aldose reductase inhibitors // Journal of Medicinal Chemistry. -1991. -vol. 34. -P. 1492-1503.

6.   Abida, Nayyar P., and Arpanarana M., “An updated review: newer quinazoline derivatives under clinical trial” // International Journal of Pharmaceutical & Biological Archive, -2011. -vol. 2, no 6, -P. 1651–1657.

7.   Shallal H.M., Russu W.A. Discovery, synthesis, and investigation of the antitumor activity of novel piperazinyl pyrimidine derivatives // European Journal of Medicinal Chemistry. -2011. -vol. 46. -P. 2043-2057.

8.     Chilin A., Conconi M.T., Marzaro G., Guiotto A., Urbani L., Tonus F., et al. Exploring epidermal growth factor receptor (EGFR) inhibitor features: The role of fused deoxygenated rings on the quinazoline scaffold // Journal  of Medicinal Chemistry. -2010. -vol. 53. -P. 1862-1866.

9.   Sagiv-Barfi I., Weiss E., Levitzki A. Design, synthesis, and evaluation of quinazoline T cell proliferation inhibitors //   Bioorganic & Medicinal Chemistry. -2010. -vol. 18. -P. 6404-6413.

10. Pat. 1596885 (France). Brooker P.J., Newbold G.T. Fungicidal Quinazolinones // Chem. Abstr. -1969. -vol. 74. -P. 112970.

11. Pat. 972977 (Great Britain). Kuehle E., Pitter R., Grewe F., Kaspurs H. 3-(2-Alkyiaminopropenyl)-1,2,4-benzothiadiazine 1,1-dioxides and 1,3-benzodiazin-4-ones // Chem. Abstr. -1964. -vol. 61. -P. 12020b.

12. Pat. 2839446 (USA). Pyrimidine derivatives/Margot A., Gysin H. //Chem. Abstr. 1958. -vol. 52. -P. 17296.

13. Chaurasia M.R., Sharma S.K., Kumar R. Synthesis of new 6,8-disubstituted 2-guanidino-4(3H)-quinazolines as potential antifungal agents // Agric. Biol. Chem.-Japan, -1980. -vol. 44. № 3. -P. 663-665.

14. Pat. 3812121 (USA). Chupp J.P. Tetrahydrothioquinazolinones // AJChem. -1975. -P. 70378. (in Russian)

15. Lehr Sllaminski W. Plant growth regulators of the quinazoline series // ZeszytyNauk. Univ. jagiel. Ser. Nauk Mat. Przyrod., Mat., Fis. Chim.-Krakow, Poland, -1959.-№ 6. -P. 53-56; Chem. Abstr.-Washington, -1969. -vol. 55. -P. 362.

16. Shakhidoyatov Kh.M., Irisbaev A., Abdullaev N.P. Synthesis of potential plant growth regulators in the series of N-substituted lactams and quinazolines. Plant growth regulators and herbicides // Tashkent: “Fan”, -1978. -P. 166-195. (in Russian)

17. L. Krause, R. Herbs-Irmer, G. M. Sheldrick, D. Stalke, (2015). J. Appl. Cryst. 48, 3-10.

18. G. M. Sheldrick, ActaCrystallogr, A64, 112 (2008)

19. G. M. Sheldrick, ActaCrystallogr, C71, 3 (2015)

To cite this article: R. Z. Khudaykulova, G. N. Kudratov, I. S. Ortikov,  K. K. Turgunov, B. Zh. Elmuradov. Synthesis and reactions of nucleophilic substitution of 2,4-dichloro-6h-(bromine) quinazolines // Uzbek chemical journal. -2023. – Nr5. - Pp.37-45. 

Received: 23.10.2023; Accepted: 24.11.2023; Published: 26.12.2023

 

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UDK 547.326.6:661

M. L. Nurmanova, R. R. Makhkamov, F. R. Saidkulov, Sh. K. Samandarov, A. E. Kurbanbaeva

COLLOID CHEMICAL PROPERTIES OF NEW SURFACTANTS BASED ON ALIPHATIC CARBON ACIDS

Institute of General and Inorganic Chemistry of the Academy of Sciences of the Republic of Uzbekistan, e-mail: nurmanova.mohira@gmail.com

Abstract. Background. The main method of dust suppression is water spraying, but when there is a shortage of water, it is ineffective and expensive. The creation of new surfactants is important for solving the problem of dust suppression.

Purpose. Synthesis of sulfoester fatty acids based on local raw materials, study of their surface activity and foaming ability.

Methodology. pH meter, method for determining surface tension (σ) tensiometer DCAT 9T (GmbH, Germany); method for determining the stability and foaming ability of surfactants GOST 23409.26-78.

Originality. Surfactants are synthesized by sulfurization of esters and esterification of acids with alcohol. An increase in the length of hydrocarbon chains in a surfactant molecule affects their surface activity.

Findings. The critical concentration of surfactant micelle formation is in the concentration range of 0.25-1.25%. Foaming ability correlates with surface activity.

Key words: surfactant, surface tension, foaming ability, foam, dust suppression.

Highlights:

- surfactants and natural polymers retain moisture on the soil surface;

- the compositions form an elastic film on the soil surface.

References

1. Workshop on colloidal chemistry. Edited by I.S. Lavrova. -Moscow: Higher School, 1983. -216 p. (in Russian)

2. Egorova I.Yu. // Bulletin of Tver State University. Series: Chemistry, 2007. -No. 15. -P. 86. (in Russian)

3. Surfactants and detergents. Directory. / Ed. Abramzon A.A. M.: "Hyperox". -1993. -270 s. (in Russian)

4. Verezhnikov V.N. Workshop on colloidal chemistry of surfactants. -Voronezh: VSU, 1984. -P. 285. (in Russian)

5. Makhkamov R., Kim V., Aminov S., Sirazhiddinova D. (1992) Correlation between the structure of a carbohydrate substituent and the adsorption ability in a series of the derivatives of hexylene-succinic acid.// Kolloid Journal 54:(4)121-124. (in Russian)

6. Usmanov R.M., Abdikamalova A.B., Eshmetov I.D., Kuldasheva S.A., Eshmetov R.J., Sharipova A.I. Obtaining coal adsorbents based on local wood waste, research of their physico-chemical and adsorption properties. //Journal of Critical Reviews. -Vol 7. -Issue 12. -2020., Scopus (3) (IF. 0.6)

7. Surfactants in Solution (1996) ed. A.K.Chattopadhyay, K.L.Mittal, 440 p.

8. Zhaksybaev Zhomart “Synthesis and development of technology for the production of a new surfactant from raw materials of natural origin.” -2020 (graduate work.) (in Russian)

9. Ochilov A.A., Abdurakhimov S.A., Salikhanova D.S. Eshmetov R.Zh. Synthesis of demulsifiers based on secondary waste from the oil and fat industry. //UNIVERSUM: Chemistry and biology: electronic scientific journal. - Russia. -2020. - No. 2(71).- P. 50-53. (02.00.00.№2) (in Russian)

10. Makhkamov R., Kim V., Aminov S., Sirazhiddinova D. (1992) Correlation between the aggregative stability of emulsions and the hydration of an emulsifier cation.// Kolloid Journal 54:(4)118-120 (in Russian)

11. Makhkamov R., Kurbanbaeva A., Khalmuminova D., Saidkulov F., Nurmanova M., Samandarov Sh., Saidakhmedova Kh. Synthesis and colloidal-chemical properties of new surface-active derivatives of maleic acid // Web of science: international scientific research journal. -ISSN: 2776-0979. -Volume 3. -Issue 4. -2022.  -Р. 389-398.

12. NoskovB. A.; LoglioG.; MillerR. Dilational viscoelasticity of  polyelectolyte/surfactant adsorption films at the air/water interface:  Dodecyltrimethylammonium bromide and sodium poly (styrenesulfonate).// J. Phys. Chem. -2004. -108, 18615.

13. Абдукаримов М.М., Ёдгаров Н., Бекназаров Х.С., Жалилов А.Т. Антикоррозионные свойства модифицированной госсиполовой смолы и композиционных покрытий на ее основе// Universum: Технические науки, Выпуск: 7 (76). -2020. Ч.2., 02.00.00; №1(in Russian)

14. Karsa R (1998). New Products and Applications in Surfactant Technology, 245 p.

15. Kronberg B., Holmberg K., Lindman B. Types of surfactants, their synthesis, and applications. Surface Chemistry of Surfactants and Polymers. Wiley, Hoboken, NJ, USA. -2014, - 324 р.

16. Bhadani A., Hokyun J. (2020) Synthesis and properties of renewable citronellol based biodegradable anionic surfactant.// Coll. Polym. Sci. 298:(11)1543-1550.

17. E. Negim, L. Kozhamzharova, J. Khatib, L. Bekbayeva, C. Williams. Effects of Surfactants on the Properties of Mortar Containing Styrene Methacrylate Superplasticizer // The Scientific World Journal. -2014. -V. -P. 10.

To cite this article: M. L. Nurmanova, R. R. Makhkamov, F. R. Saidkulov, Sh. K. Samandarov, A. E. Kurbanbaeva. Colloid chemical properties of new surfactants based on aliphatic carbon acids // Uzbek chemical journal. -2023. – Nr5. - Pp.46-51

Received: 23.10.2023; Accepted: 24.11.2023; Published: 26.12.2023

 

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UDK 665.7.038+620.197

S. А. Berdiev

STUDYING THE INFLUENCE OF SYNERGIC COMPOSITES BASED ON ORGANIC OXYGEN-CONTAINING ETERS ON THE OCTANE NUMBER

Tashkent scientific research institute of chemical technology,Tashkent, Uzbekistan, ORCID: 0009-0005-1516-2840, sanjarberdiev75@gmail.com

Abstract. Background. Despite the significant increase in the need for energy in the world due to industrialization, high economic growth, modern transport technology systems and the development of the energy sector, due to the limited reserves of oil or fossil fuels, their use is 26-27% of the total need. Therefore, meeting strict standard requirements of fuel quality, using modifiers to obtain high-quality fuel is important in the production of gasoline and diesel fuel.

Purpose. It consists in the development of a technology for obtaining multifunctional additives that improve the mechanical properties of gasoline and diesel fuels.

Methodology. The subject of the research is to study the optimal conditions of the process of obtaining multifunctional modifiers based on metal and nitrogen-containing compounds, to obtain modifiers that increase the octane number of gasoline, and to develop the technology of obtaining metal-containing antidetonators.

Originality. E-1, E-2 and E-3 organic esters containing oxygen as additives to increase the octane number of petroleum fuels, the effect on the octane number of the directly driven gasoline fraction compared to analogues is 0.4-1.82 units in the motor octanerating (MOR) method, 0 in the research octane rating (ROR) method. 7-2.5 units improved, and the effect of the gasoline fraction of the reformate sample on the octane number improved by 0.2-1.3 units in the ROR method, and by 0.1-1.1 units in the MOR method.

Findings. According to the obtained preliminary results, the improvement of the octane number of the proposed modifiers with an effective effect on the octane number compared to their analogues allows the use of these modifiers as synergistic additives for increasing the octane number on the properties of petroleum fuels.

Key words: organic modifier, composite, oxygenated organic ethers, analogue, octane number, concentration.

Highlights:

- a technology for the production of metal-containing organic compounds has been developed:

- modifiers with anti-knock properties;

- the resulting modifiers increase the octane number of fuels;

- composite materials with high anti-corrosion efficiency;

- physical and chemical properties of composite materials.

References

1.   Ershov, M.A., Experience and prospects for the use of bioethanol fuels / M.A. Ershov, E.V. Trifonova, I.F. Khabibulin, E.V. Emelyanov // Oil refining and petrochemistry. Scientific and technical achievements and best practices. - 2014. - No. 12. - P. 33-37.

2.   Karpov, S.A. Ethanol on the experience of using motor gasoline / S.A. Karpov // World of petroleum products. Bulletin of oil companies. - 2006. - No. 6. - P. 6-7.

3.   Borzaev, B.Kh. Multifunctional additives for motor gasoline / B.Kh. Borzaev, S.P. Karpov, V.M. Kapustin // Chemistry and technology of fuels and oils. – 2007. - No. 4. – P. 18-20.

4.   Sachivko, A.V. Phase equilibria in the hydrocarbons – ethanol – water system at different temperatures / A.V. Sachivko, O.A. Naumova, V.P. Tverdokhlebov, D.G. Ershov // News of higher educational institutions. Series: Chemistry and chemical technology. - 2008. - No. 10. - P.29-31.

5.   Efendi, A.J. Methods for producing alternative fuelsbased on methanol / A.J. Efendi, A.M. Alieva, L.G. Maharramova, L.I. Kozharova, I.G. Melikova, E.M. Babaeva // Oil refining and petrochemistry. Scientific and technical achievements and best practices. - 2019. - No. 2. - P. 27-32.

6.   Potanin, D.A. Experience and prospects for using methanol in the production of motor gasoline / D.A. Potanin, M.A. Ershov, E.V.Emelyanov, M.V. Kapustin // Oil refining and petrochemistry. Scientific and technical achievements and best practices. - 2015. - No. 15. - P. 3-5.

7.   Stryakhileva, M.N. Production of methyl tert-alkyl ethers - high-octane components of gasoline / M.N. Stryakhileva, G.N. Krymova, D.N. Chaplits, I.P. Pavlova, A.M. Baunov // Thematic review. M.: – 1988. – No.8. - 72 p.

8.   Mikishev, V.A. Industrial experience of the MTBE synthesis plant at JSC "ANHK" / A.A. Trukhina, M.V. Andriyanov, M.S. Glazkova // World of petroleum products. Bulletin of oil companies. - 2015. – No. 9. – P. 29-31.

9.   Patent No.SU1838383 A3 USSR Composition of hydrocarbon fuel / Burmistrov O.A., Lebedev S.R., Kuznetsova L.N. et al. - No. 5022664/04Application 01/17/92; Publ. 08/30/93 Bulletin. No. 32.

10. Georgieva, E.Yu. Study of the possibility of using alcohols as a high-octane component of catalytic cracking gasoline [Electronic resource] / E.Yu. Georgieva, A.V. Sundurov // “Scientific and practical electronic journal Alley of Science”. - 2018. - No. 6(22).

11. Shevchenko V.S. Fuel additives: MTBE at the peak of consumption in Russia [E-resource] / V.S. Shevchenko // Bulletin of the chemical industry. – 2016. –Link: http://vestkhimprom.ru /posts/toplivnyeprisadki-mtbe-na-pike-potrebleniya-v-rossii

12. Sidracheva, I.I. Research into the possibility of involving butylalcohols into gasoline produced by OJSC "Salavatnefteorgsintez" / I.I. Sidracheva, A.V. Sitdikova, A.S. Alyabyev, I.V. Rogozha // Oil refining and petrochemistry. Scientific and technical achievements and best practices. - 2009. - No.6. - P.24-28.

13. Ershov, M.A. Biobutanol in comparison with other oxygenates / M.A.Ershov, E.V. Emelyanov, T.A. Klimova // World of petroleum products. Bulletin of oil companies – 2012. - No. 2. – P. 3-6.

14. Patent No. US 8968429 B2 USA Butanol compositions for fuel blending and methods for the production thereof / Baustian, James J. (St. Charles, IL, US) Wolf, Leslie Raymond (Naperville, IL, US) - No. 13/243569 Application 09.23.11; Publ. 03.03.15.

To cite this article: S. А. Berdiev. Studying the influence of synergic composites based on organic oxygen-containing eters on the octane number // Uzbek chemical journal. -2023. – Nr5. - Pp.52-58

Received: 20.12.2023; Accepted: 25.12.2023; Published: 26.12.2023

 

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UDK 665.7.038+620.197

S. А. Berdiev, А.Т. Djalilov

STUDYING THE EFFECTIVENESS OF NITROGEN AND SULFUR CONTAINING ORGANIC OLIGOMERIC ADDITIVES SOLUBLE IN PETROLEUM OILS

Tashkent Scientific Research Institute of Chemical Technology, Tashkent, Uzbekistan, ORCID: 0009-0005-1516-2840, sanjarberdiev75@gmail.com

Abstract. Background. Additives based on nitrogen, oxygen and sulfur organic compounds and their composite mixtures are used worldwide to improve fuel quality. Therefore, great attention is being paid to research and development aimed at the development of effective methods of obtaining composites that affect the operational properties of petroleum products.

Purpose. Development of technology for obtaining additives containing nitrogen, oxygen and sulfur in the composition of petroleum products, improving their operational properties.

Methodology. Modern cryoscopic analysis, IR-spectroscopy, elemental analysis, ultraviolet spectroscopy, thermal analysis (DTA, TGA - derivatogram) methods, motor (OSM) and research (OST) methods of determining the octane number were used as research methods.

Originality. NS-1 and NS-2 brands of diesel fuel added with oligomer additives have been found to reduce the diameter of pits formed on the metal surface from 460 μm, and the samples added in the amount of 0,3% have increased the efficiency of NS-1 brand to 305 μm in diameter and NS-2 brand to 280 μm in diameter.

Findings. Oligomer additives NS-1 and NS-2, which contain nitrogen and sulfur, meet modern requirements, and when a combined corrosion inhibitor is used as a component, the level of corrosion protection in industrial И-20A oils has improved to 93,2 %.

Key words: oligomer additive, viscosity, corrosion rate, fluidity, inhibitor, industrial oil И-20A.

Highlights:

- level of corrosion protection for oligomeric additives of the NS-1 brand, containing nitrogen and sulfur;

- the anti-corrosion ability of mixtures was studied using the gravimetric method;

- a mixture of NS-1 corrosion inhibitor with 5-20% industrial oil I-20A;

- it was found that the degree of corrosion protection was 92.3%.

References

1. E. Stupnisek-Lisac, A. Gazivoda, M. Mod zarac, Electrochim. Acta 47 (2002) 4189 b.

2.  E. Rocca, G. Bertrand, C. Rapin, J.C. Labrune, J. Electroanal. 503 (2001) 133 b.

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To cite this article: S. А. Berdiev, А.Т. Djalilov. Studying the effectiveness of nitrogen and sulfur containing organic oligomeric additives soluble in petroleum oils // Uzbek chemical journal. -2023. – Nr5. - Pp.58-64. 

Received: 20.12.2023; Accepted: 25.12.2023; Published: 26.12.2023

 

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