Inhibited Oxidation of Hydrocarbons in the Presence of Nitrogen, Phosphorus, Selenium, and Sulfur-Containing Heterocyclic Compounds

Document Type : Research Article

Authors

1 A.M. Kuliev Institute of the Chemistry of Additives, ANAS, Baku, AZERBAIJAN

2 LA.M. Kuliev Institute of the Chemistry of Additives, ANAS, Baku, AZERBAIJAN

3 A.E. Favorsky Irkutsk Institute of Chemistry, SB RAS, Irkutsk, RUSSIA

Abstract

With the expansion of the scope of lubricant oils and fuels, the requirements for their performance properties are increasing. One of the performance characteristics of these petroleum products is their resistance to oxidation. It is known that as a result of oxidation, their performance properties deteriorate. Antioxidant stabilizers are used to increase the resistance of organic materials against oxidation. The study of the mechanism of action of oxidation inhibitors is one of the most important tasks in this field, the solution of which is the creation of a theoretically substantiated approach to the targeted synthesis of more effective antioxidants. To create the theoretical and practical foundations of solving this problem was to find novel classes of effective additives of multivalent activity, particularly antioxidants, a series of recently synthesized nitrogen, sulfur, selenium and phosphorus polyfunctional compounds, including pyrroledithioates, 6,8-bicycloctanes, aminopyrimidine, tris(2-pyridyl)phosphinesulfide and -selenide have been investigated using model oxidative reactions. The compounds studied appear to be perspective inhibitors of hydrocarbon oxidation. Some of them are antioxidants of combined action, breaking the chains of the oxidative reactions with cumene peroxide radicals and catalytically decomposing cumene hydroperoxide.

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[1] Mustafayev N., Novotorzhina N., Ramazanova Y., et al., Synthesis and Study of Novel Derivatives of 1, 3-Dioxolane as Anti-Seizing Additives to Lubricating Oils, Chemistry Africa, 5: 821–826 (2022).
[2] Farzaliyev V., Mustafayev N., Efendiyeva K., et al.,  Synthesis and Study of Bisakylxanthogenates as Additives to Lubricating Oils, Chemistry Africa, 5(3): 569-574 (2022).
[3] Akchurina T., Sardarova S., Efendiyeva Kh., Eyvazova I., Farzaliyev V., Sujayev A., Synthesis and Study of aroylethyl(ethyl)-xanthates as Stabilizers of Polymeric Materials, Applied Petrochemical Research, 11(3): 327-333 (2021).
[4] Garibov E.N., Rzaeva I.A., Shikhaliev N.G., Kuliev A.I., Farzaliev V.M., Allakhverdiev M.A., Cyclic Thioureas as Cumene Oxidation Inhibitors, Russ. J. Appl. Chem., 83(4): 707-711 (2010).
[5] Veliyeva L., Sadıqova A., Israfilova Z., Rzaeva I., Kurbanova M., Farzaliyev V., Maharramov A., Sujayev A., Towards Fuel Antioxidants of New Types, Applied Petrochemical Research. 11(3): 317-325 (2021)
[6] Magerramov A.M., Kurbanova M.M., Abdinbekova R.T., Rzaeva I.A., Farzaliev V.M., Allakhverdiyev M.A., Synthesis and Antioxidative Properties of Some 3,4-dihydropyrimidin-2(1H)ones(-thiones), Russ. J. Appl. Chem., 79(5): 787-790 (2006).
[8] Howard J.K., Rihak K.J., Bissember A.C., Smith J.A., The Oxidation of Pyrrole, Chem. Asian J., 11: 155–167 (2016).
[9] Emanuel N.M., Denisov E.T., Mayzus Z.K., “Chain Reactions of Hydrocarbon Oxidation in Liquid Phase”, Macmillan, 375 (1965).
[10] Scott G., Shearn P.A., Mechanisms of Antioxidant Action: Effects of Sulfur Compounds on the Melt Stability of Polypropylene, J. Appl. Polym. Sci., 13(7): 1329-1335 (1969).
[11] Nagiyeva E., Farzaliyev V., Kazımzadeh A., Ramazanova Y., Mammedyarova K., Mammedova R., Sujayev A., Synthesis and Study of Modified Alkylphenolate Additives for Motor Oils, Iran. Jour. Chem. Chem. Eng., 41(12): 4098-4103 (2022).
[12] Bhardwaj V., Gumber D., Abbot V., Dhiman S., Sharma P., Pyrrole: a Resourceful Small Molecule in Key Medicinal Hetero-Aromatics, RSC Adv., 5: 15233-15266 (2015).
[13] Gholap S.S., Pyrrole: An Emerging Scaffold for Construction of Valuable Therapeutic Agents,  Eur. J. Med. Chem., 110: 13-31 (2016).
[14] Kaur R., Rani V., Abbot V., Kapoor Y., Konar D., Kumar K., Recent Synthetic and Medicinal Perspectives of Pyrroles: An Overview, J. Pharm. Chem. Chem. Sci., 1(1): 17-32 (2017).
[15] Tzankova D., Vladimirova S., Peikova L., Georgieva M., Synthesis of Pyrrole and Substituted Pyrroles, J. Chem. Tech. Metal., 53(3): 451-464 (2018).
[16] Trofimov B.A., Mikhaleva A.I., Schmidt E.Y., Sobenina L.N., “Chemistry of pyrroles”, CRC Press, 398 (2016).
[17] Trofimov B.A., Schmidt E.Y., Ushakov I.A., Mikhaleva A.I., Zorina N.V., Protsuk N.I., Senotrusova E.Y., Skital’tseva E.V., Kazheva O.N., Alexandrov G.G., Dyachenko O.A., One-Pot Assembly of 7-Methylene-6,8-dioxabicyclo[3.2.1]octanes, Congeners of Frontalin, from Ketones and Acetylene, Eur. J. Org. Chem., 30: 5142-5145 (2009).
[18] Schmidt E.Y., Bidusenko I.A., Cherimichkina N.A., Trofimov B.A., Expedient Nonclassical Reaction of Acetylenes with Ketones: Controlling the Switch Between Bicyclic Ketals and Cyclopentenols Formation, ARKIVOC, 7: 145-157 (2015).
[19] Schmidt E.Y., Bidusenko I.A., Ushakov I.A., Protsuk N.I., Trofimov B.A., An Easy Access to Sulfur Derivatives of 6,8-Dioxabicyclo[3.2.1]octanes, Naturally Abundant Scaffolds, Synthesis, 50(13): 2624-2630 (2018).
[20] Schmidt E.Y., Tatarinova I.V., Protsuk N.I., Ushakov I.A., Trofimov B.A., A One-Pot Synthesis of 2-Aminopyrimidines from Ketones, Arylacetylenes, and Guanidine, J. Org. Chem., 82(1): 119-125 (2017).
[21] Malysheva S.F., Kuimov V.A., Trofimov A.B., Belogorlova N.A., Litvintsev Y.I., Belogolova A.M., Gusarova N.K., Trofimov B.A., 2-Halopyridines in a Triple Reaction in the Pn/KOH/DMSO System to form Tri(2-pyridyl)phosphine: Experimental and Quantum-Chemical Dissimilarities, Mendeleev Commun., 28: 472–474 (2018).
[22] Kharat A.N., Bakhoda A., Hajiashrafi T., Abbasi A., Synthesis, Characterization, and Crystal Structures of Tris(2-pyridyl)phosphine Sulfide and Selenide, Phosphorus, Sulfur and Silicon., 185(11): 2341-2347 (2010).