Benzalkonium bromides (BAK) are an important class of cationic surfactants with both industrial and commercial uses. They are used as preservatives for ophthalmic, nasal and parenteral products and they are also used as a topical antiseptic and medical equipment disinfectant. In this work a universal method for the preparation of these compounds is described. Using quaternization of N,N-dimethylbenzylamines with long-chain n-alkylbromides we have prepared C8, C10, C12, C14, C16, C18 and C20 homologues of the benzalkonium bromides (BAK).
benzalkonium bromides; dimethylbenzylamines; n-alkylbromides; alkylating agent; quaternization
Avram E: Quaternization reaction of some N,N-dimethylalkylamines with benzyl chloride. Rev Roum Chim 46:49-54, 2001.
Dohnal V, Kuca K, Bielavska M, Cabal J: Determination of the benzalkonium homologs in desinfectant using HPLC (In Czech). Zprav Voj Farm 13:5-8, 2003.
Echols L, Maier VP, Poling SM, Sterling PR: New bioregulators of gibberellin biosynthesis in Gibberella fujikuroi. Phytochemistry 20:433-438, 1981.
Ferrier A, Garin D, Crance JM: Rapid inactivation of vaccinia virus in suspension and dried on surfaces. J Hosp Infect 57:73-79, 2004.
McBain AJ, Ledder RG, Moore LE, Catrenich CE, Gilbert P: Effects of quaternary-ammonium-based formulations on bacterial community dynamics and antimicrobial susceptibility. Appl Environ Microbiol 70:3449-3456, 2004.
Merianos JJ: In Block SS (ed.), Disinfection, sterilization and preservation; Lea and Febinger, PA, 1991, pp. 225-255.
Moss RA, Sunshine WL: Micellar catalysis of ester hydrolysis. The Influence of chirality and head group structure in "simple" surfactants. J Org Chem 39:1083-1089, 1974.
Novaki LP, El Seoud OA: Solvatochromism in aqueous micellar solutions: effects of the molecular structures of solvatochromic probes and cationic surfactants. Phys Chem Chem Phys 1:1957-1964, 1999.
Rudakova AW, Popova LP: Study of reaction capability of lygnoceryl alcohol (In Russian). Z Obsc Chim 36:242-244, 1966.
Stepanenko BN, Ulimina TS, Zelenkova VV: Synthesis of some qauternary salts of ammonium compounds (In Russian). Chim Farm Z 8:21-24, 1974.
Zhuravlev SV, Sukhareva ND, Chadova EK: The synthesis and study of quaternary ammonium salts (In Russian). Tr Central Naucn Issl Dezinf Inst 8:125-127, 1954.
Muhizi T, Coma V, Grelier S. Synthesis of D-glucosamine quaternary ammonium derivatives and evaluation of their antifungal activity together with aminodeoxyglucose derivatives against two wood fungi Coriolus versicolor and Poria placenta: structure-activity relationships. Pest Management Sci. 67: 287-293, 2011.
Mathew S, Divia N, Nair TDR, Haridas KR. Synthesis and characterization of novel starburst phase transfer catalyst. Indian J Chem., Sect B. 49: 1389-1393, 2010.
Cabal J, Micova J, Kuca K. Kinetics of hydrolysis of organophosphate soman by cationic surfactant Resamin AE. J Appl Biomed. 8: 111-116, 2010.
Muhizi T, Grelier S, Coma V. Synthesis of N-Alkyl-beta-D-glucosylamines and Their Antimicrobial Activity against Fusarium proliferatum, Salmonella typhimurium, and Listeria innocua. J Agric Food Chem. 57: 11092-11099, 2009.
Galletti P, Montecavalli A, Moretti F, Pasteris A, Samori C, Tagliavini E. Furan containing ammonium salts from furfural: synthesis and properties evaluation. New J Chem. 33: 1859-1868, 2009.
Muhizi T, Coma V, Grelier S. Synthesis and evaluation of N-alkyl-beta-D-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta. Carbohydr Res. 343: 2369-2375, 2008.
Kuca K, Marek J, Stodulka P, Musilek K, Hanusova P, Hrabinova M, Jun D. Preparation of benzalkonium salts differing in the length of a side alkyl chain. Molecules. 12: 2341-2347, 2007.
Jun D, Stodulka P, Koleckar V, Kuca K. TLC identification of benzalkonium bromide homologs. J Planar Chromatogr - Mod TLC. 20: 283-285, 2007.
Cabal J, Kuca K, Micova J. Kinetics of decompositition of organophosphate Fenitrothion by decontaminating foam-making blends. J Appl Biomed. 5: 167-170, 2007.
Kuca K, Bielavska M, Cabal J, Dohnal V. Determination of benzalkonium bromide homologues in disinfection products using high-performance liquid chromatography. Anal Lett. 38: 673–682, 2005.