The aim of this work is to study the synthesis of quaternary ammonium compounds based on olefins and to investigate the structure and properties of the obtained products. To achieve this goal, at the first stage, the process of obtaining isohexyl monochloroacetate by the esterification reaction of hexene isomers with monochloroacetic acid in the presence of an acid catalyst was studied and then by the cauterization reaction of the obtained product with triethylamine, quaternary ammonium salts were obtained in an organic solvent medium at 30 °C. The influence of the initial reagents, the nature of the solvent and temperature on the rate of the quaternization reaction was studied. The influence of the reaction duration on the yield of the formed quaternary salts was also studied. The physical properties of the synthesized esters and quaternary ammonium salts were determined. The structure of the product was determined by IR spectroscopy and thermoanalytical methods. A basic technological scheme for the synthesis of quaternary ammonium compounds is proposed.
D. N. Borisov, P. S. Fakretdinov, and G. V. Romanov, “Synthesis of ammonium compounds based on decene-1 and their effect on the viscosity of high-paraffin oil,” Neftegazovoe Delo, 2007, p. 10. [Online]. Available: http://www.ogbus.ru/authors/Borisov/Borisov_1.pdf.
M. C. Jennings, K. P. Minbiole, and W. M. Wuest, “Quaternary ammonium compounds: An antimicrobial mainstay and platform for innovation to address bacterial resistance,” ACS Infect. Dis., vol. 1, no. 7, pp. 288–303, 2015, doi: 10.1021/acsinfecdis.5b00047.
C. L. Schrank, K. P. Minbiole, and W. M. Wuest, “Are quaternary ammonium compounds, the workhorse disinfectants, effective against severe acute respiratory syndrome-coronavirus-2?,” ACS Infect. Dis., vol. 6, no. 7, pp. 1553–1557, 2020, doi: 10.1021/acsinfecdis.0c00265.
X. Zhong, R. Li, Z. Wang, W. Wang, and D. Yu, “Titanium dioxide/quaternary phosphonium salts/polyacrylonitrile composite nanofibrous membranes with high antibacterial properties and ultraviolet resistance efficiency,” J. Mater. Sci., vol. 54, pp. 13322–13333, 2019.
I. M. Garcia, S. B. Rodrigues, G. S. Balbinot, F. Visioli, V. C. B. Leitune, and F. M. Collares, “Quaternary ammonium compound as antimicrobial agent in resin-based sealants,” Clin. Oral Investig., 2019, pp. 1–8.
P. Makvandi, M. Ghaemy, A. A. Ghadiri, and M. Mohseni, “Photocurable antimicrobial quaternary ammonium–modified nanosilica,” J. Dent. Res., vol. 94, pp. 1401–1407, 2015.
J. Hermens, P. Leeuwangh, and A. Musch, “Joint toxicity of mixtures of groups of organic aquatic pollutants to the guppy (Poecilia reticulata),” Ecotoxicol. Environ. Saf., vol. 9, no. 3, pp. 321–326, 1985, doi: 10.1016/0147-6513(85)90049-1.
M. Faust, R. Altenburger, T. Backhaus, H. Blanck, W. Boedeker, P. Gramatica, V. Hamer, M. Scholze, M. Vighi, and L. Grimme, “Joint algal toxicity of 16 dissimilarly acting chemicals is predictable by the concept of independent action,” Aquat. Toxicol., vol. 63, no. 1, pp. 43–53, 2003, doi: 10.1016/S0166-445X(02)00133-9.
V. I. Levashova and N. I. Nikonorova, “Synthesis and investigation of the properties of quaternary ammonium salts based on N,N′-tetramethyldiaminomethane and 4-chloro-2-pentene,” Neftekhimiya, vol. 49, no. 3, pp. 268–271, 2009.
F. A. Makhmudova and O. S. Maksumova, “Synthesis and investigation of ammonium salts based on isohexyl monochloroacetate and triethylamine,” Dokl. Akad. Nauk Respubliki Uzbekistan, vol. 5, pp. 36–37, 2012.
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