Acenaphthene Nitro Derivatives Plasma-Chemical Synthesis in the High-Frequency Currents Field at Reduced Pressure

Abstract

Plasma-chemical processing devices are widely used in practice and are an integral part in microelectronics, medicine, light industry and nanotechnology. In addition, they are used as methods for modifying the modern materials surfaces and in liquids processing. The paper considers preparation of the aromatic compound nitro derivatives under the action of capacitive high-frequency electrodeless discharge at the gas--liquid interface with the reduced pressure. During the plasma-chemical treatment of the reaction mixture containing the 1,2-dihydroacenaphthylene (acenaphthene), its complete conversion was observed, which was confirmed by detection of the acenaphthene mono- and dinitro-derivatives, as well as of the side chain oxidation products, in the reaction products. The proposed method of implementing nitration reaction of the aromatic substances, which belongs to the new instrumental methods of organic synthesis along with photochemistry and electrochemical synthesis, allows direct binding of the molecular nitrogen and oxygen into the valuable nitrogen-containing organic compounds. Study results demonstrate effective introduction of the plasma chemistry methods in chemical technology not only for the purposes of oxidative destruction of the organic substances, but also as the physicochemical tools for the fine organic synthesis allowing selective functionalization of the polynuclear aromatic compounds

The work was supported by the grant from the Russian Science Foundation (project no. 21-79-30062)

Please cite this article in English as:

Lubin A.A., Yakushin R.V., Oshchepkov M.S., et al. Acenaphthene nitro derivatives plasma-chemical synthesis in the high-frequency currents field at reduced pressure. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2023, no. 4 (109), pp. 123--140 (in Russ.). DOI: https://doi.org/10.18698/1812-3368-2023-4-123-140

References

[1] Khangholi A., Revilla R.I., Lutz A., et al. Electrochemical characterization of plasma coatings on printed circuit boards. Prog. Org. Coat., 2019, vol. 137, art. 105256. DOI: https://doi.org/10.1016/j.porgcoat.2019.105256

[2] Dunaev A.V., Murin D.B. Structuring copper in the plasma medium of a high-frequency discharge. Russ. Microelectron., 2018, vol. 47, no. 4, pp. 234--238. DOI: http://doi.org/10.1134/S1063739718040029

[3] von Woedtke T., Schmidt A., Bekeschus S., et al. Plasma medicine: a field of applied redox biology. In Vivo, 2019, vol. 33, iss. 4, pp. 1011--1026. DOI: https://doi.org/10.21873/invivo.11570

[4] Nayak R., ed. Sustainable technologies for fashion and textiles. Woodhead, 2020.

[5] Timoshina Y.A., Voznesensky E.F., Tskhay E.S., et al. Modification of surface of textile materials with silver nanoparticles in the radio-frequency induction plasma discharge of low pressure. J. Phys.: Conf. Ser., 2019, vol. 1328, art. 012083. DOI: http://doi.org/10.1088/1742-6596/1328/1/012083

[6] Laroussi M. Cold plasma in medicine and healthcare: the new frontier in low temperature plasma applications. Front. Phys., 2020, vol. 8, art. 74. DOI: http://doi.org/10.3389/fphy.2020.00074

[7] Magureanu M., Bilea F., Bradu C., et al. A review on non-thermal plasma treatment of water contaminated with antibiotics. J. Hazard. Mater., 2021, vol. 417, art. 125481. DOI: http://doi.org/10.1016/j.jhazmat.2021.125481

[8] Gushchin A.A., Grinevich V.I., Izvekova T.V., et al. Water purification to remove naphthalene by treatment with dielectric-barrier discharge in oxygen. High Energy Chem., 2022, vol. 56, no. 3, pp. 208--212. DOI: https://doi.org/10.1134/S0018143922020047

[9] Gushchin A.A., Gusev G.I., Grinevich V.I., et al. Destruction of 2,4-dichlorophenol in water solution using a combined process of sorption and plasma exposure to DBD. Plasma Chem. Plasma Process., 2021, vol. 41, no. 1, pp. 421--431. DOI: http://doi.org/10.6060/ivkkt.20216411.6507

[10] Zhang Z., Gong X., Zhang S., et al. Observation of replacement of carbon in benzene with nitrogen in a low-temperature plasma. Sci. Rep., 2013, vol. 3, no. 1, art. 3481. DOI: https://doi.org/10.1038/srep03481

[11] Hosseini H., Saleem M., Marotta E., et al. Nitrogen-containing organic products from the treatment of liquid toluene with plasma-activated N2 gas. Plasma Process. Polym., 2021, vol. 18, iss. 5, art. 2100012. DOI: https://doi.org/10.1002/ppap.202100012

[12] Dashevskiy M.M., ed. Atsenaften [Acenaphthene]. Moscow, Khimiya Publ., 1966.

[13] Dood A.J., Fisher P.A., Bodden C.L., et al. Synthesis of 5,6-diaminoacenaphthylene by reduction of sterically crowded nitro groups with sodium dithionite. SynOpen, 2018, vol. 2, no. 4, pp. 0312--0315. DOI: https://doi.org/10.1055/s-0037-1610406

[14] Ye F., Liang X.-M., Xu K.-X., et al. A novel dithiourea-appended naphthalimide "on-off" fluorescent probe for detecting Hg²⁺ and Ag⁺ and its application in cell imaging. Talanta, 2019, vol. 200, pp. 494--502. DOI: https://doi.org/10.1016/j.talanta.2019.03.076

[15] Oshchepkov A.S., Oshchepkov M.S., Oshchepkova M.V., et al. Naphthalimide-based fluorescent polymers for molecular detection. Adv. Opt. Mater., 2021, vol. 9, iss. 6, art. 2001913. DOI: https://doi.org/10.1002/adom.202001913

[16] Grabchev I., Konstantinova T. Synthesis of some polymerisable 1,8-naphthalimide derivatives for use as fluorescent brighteners. Dyes Pigm., 1997, vol. 33, iss. 3, pp. 197--203. DOI: https://doi.org/10.1016/S0143-7208(96)00053-8

[17] Grabchev I., Qian X., Bojinov V., et al. Synthesis and photophysical properties of 1,8-naphthalimide-labelled PAMAM as PET sensors of protons and of transition metal ions. Polymer, 2002, vol. 43, iss. 21, pp. 5731--5736. DOI: https://doi.org/10.1016/S0032-3861(02)00417-2

[18] Panchenko P.A., Fedorova O.A., Fedorov Yu.V. Fluorescent and colorimetric chemosensors for cations based on 1,8-naphthalimide derivatives: design principles and optical signalling mechanisms. Russ. Chem. Rev., 2014, vol. 83, no. 2, pp. 155--182. DOI: https://doi.org/10.1070/RC2014v083n02ABEH004380

[19] Hao Y., Zhang Y., Ruan K., et al. A naphthalimide-based chemodosimetric probe for ratiometric detection of hydrazine. Sens. Actuators B Chem., 2017, vol. 244, pp. 417--424. DOI: https://doi.org/10.1016/j.snb.2016.12.145

[20] Goel R., Sharma S., Paul K., et al. Naphthalimide based chromofluorescent sensor and DNA intercalator: triggered by Hg²⁺ / HSO^-₄ cleavage reaction. Sens. Actuators B Chem., 2017, vol. 246, pp. 776--782. DOI: http://doi.org/10.1016/j.snb.2017.02.090

[21] Oshchepkov A., Oshchepkov M., Pavlova G., et al. Naphthalimide-functionalized bisphosphonates for fluorescence detection of calcification in soft tissues. Sens. Actuators B Chem., 2020, vol. 314, art. 128047. DOI: https://doi.org/10.1016/j.snb.2020.128047

[22] Oshchepkov M.S., Semyonkin A.S., Menkov A.O., et al. Microflow synthesis of fluorescent markers based on 1,8-naphthalimide for polylactide nanoparticles and bioimaging. Mendeleev Commun., 2020, vol. 30, iss. 6, pp. 747--749. DOI: https://doi.org/10.1016/j.mencom.2020.11.019

[23] Malik M.A. Nitric oxide production by high voltage electrical discharges for medical uses: a review. Plasma Chem. Plasma Process., 2016, vol. 36, no. 3, pp. 737--766. DOI: https://doi.org/10.1007/s11090-016-9698-1

[24] Piskarev I.M., Ivanova I.P., Trofimova S.V., et al. Formation of peroxynitrite induced by spark plasma radiation. High Energy Chem., 2014, vol. 48, no. 3, pp. 213--216. DOI: https://doi.org/10.1134/S0018143914030138

[25] Piskarev I.M., Ivanova I.P., Trofimova S.V., et al. Formation of peroxynitrite induced by spark plasma radiation. High Energy Chem., 2014, vol. 48, no. 3, pp. 213--216. DOI: https://doi.org/10.1134/S0018143914030138

[26] Bogomolov B.B., Boldyrev V.S., Zubarev A.M., et al. Intelligent logical information algorithm for choosing energy- and resource-efficient chemical technologies. Theor. Found. Chem. Eng., 2019, vol. 53, no. 5, pp. 709--718. DOI: https://doi.org/10.1134/S004057951905027

[27] Yakushin R.V., Chistolinov A.V., Boldyrev V.S., et al. Research of liquid phase oxidation of aliphatic alcohols in plasma chemical water treatment. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2021, no. 1 (94), pp. 92--108 (in Russ.). DOI: https://doi.org/10.18698/1812-3368-2021-1-92-108

[28] Kalistratova A.V., Oshchepkov M.S., Ivanova M.S., et al. Microwave radiation applied in the N-аryl-N′-aminoеthylureas. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2021, no. 5 (98), pp. 125--141 (in Russ.). DOI: http://dx.doi.org/10.18698/1812-3368-2021-5-125-141