SUMMARY
This experiment tested the reactivity of the cationic surfactant Resamin AE
[N-(2-hydroxyethyl)-N-(2-hydroxy-4-oxa(C14÷22-alkyl))-N,N-dimethylammonium chloride] with organophosphonate soman. It was confirmed that soman is
incorporated in the micelle of Resamin AE and that the hydroxyl group or Resamin AE supports the hydrolysis of this organophosphonate. A further
increase in reactivity was achieved by the addition of hydrogen peroxide into the reaction mixture. In contrast, if the concentration of neutral
salts was increased, a decrease in the velocity of the hydrolysis was obtained. The hydrolytic efficacy of Resamin AE was also compared with that
of hexadecyldimethyl-(2-hydroxyethyl)-ammonium bromide. Resamin AE appeared to be a more efficacious hydrolytic agent than other similar compounds
due to its advantageous chemical structure.
KEY WORDS
cationic surfactants; micellar catalysis; soman; decontamination; Resamin AE
REFERENCES
Bunton CA, De Buzzaccarini F, Hamed FH: Nucleophilic aromatic substitution in microemulsions of a hydroxyethyl surfactant. J Org Chem
48:2461-2465, 1983.
Cabal J, Kassa J, Severa J: A comparison of the decontamination efficacy of foam-making blends based on cationic and nonionic tensides against
organophosphorus compounds determined in vitro and in vivo. Hum Exp Toxicol 22:507-14, 2003.
Cabal J, Kuca K, Micova J: Kinetics of decompositition of organophosphate Fenitrothion by decontaminating foam-making blends. J Appl Biomed
5:167-170, 2007.
Cabal J, Kuca K, Sevelova L, Dohnal V: Cyclodextrines as functional agents for decontamination of the skin contamined by nerve agents. Acta Medica
(Hradec Kralove) 47:115-118, 2004.
Cibulka R, Hampl F, Martinu T, Mazac J, Totevova S, Liska F: Metal ion chelates of lipophilic alkyl diazinyl ketoximes as hydrolytic catalysts.
Collect Czech Chem Commun 64:1159-1179, 1999.
Guggenheim EA: On the determination of the velocity constant of a unimolecular reaction. Phil Mag 2:538-543, 1926.
Kivala M, Cibulka R, Hampl F: Cleavage of 4-nitrophenyl diphenyl phosphate by isomeric quaternary pyridinium ketoximes - How can structure and
lipophilicity of functional surfactants influence their reactivity in micelles and microemulsions? Coll Czech Chem Commun 71:1642-1658,
2006.
Kotoucova H, Cibulka R, Hampl F, Liska F: Amphiphilic quaternary pyridinium ketoximes as functional hydrolytic micellar catalysts - does the
nucleophilic function position influence their reactivity? J Mol Catal A - Chem 174:59-62, 2001.
Kuca K, Kivala M, Dohnal V: General method for the quaternization of N,N-dimethyl benzylamines with long chain n-alkylbromides. J Appl Biomed
2:195-198, 2004.
Kuca K, Dohnal V, Bielavska M, Cabal J: Determination of benzalkonium bromide homologues in desinfection products using high-performance liquid
chromatography. Anal Lett 38:673-682, 2005.
Kuca K, Musilek K, Hanusova P, Hrabinova M, Marek J, Stodulka S, Jun D: Preparation of the benzalkonium salts differing in the length of the side
alkylating chain. Molecules 12:2341-2347, 2007.
Menger FM, Portnoy CE: On the chemistry of reactions proceeding inside molecular aggregates. J Am Chem Soc 89:4698-4703, 1967.
OECD Guidelines for the Testing of Chemicals, Test No. 115: Surface Tension of Aqueous Solutions. OECD, Paris 1981.
Ouarti N, Marques A, Blagoeva I, Ruasse MF: Optimization of micellar catalysis of nucleophilic substitutions in buffered cetyltrimethylammonium
salt solutions. 1. Buffers for the 9-10 pH range. Langmuir 16:2157-2163, 2000.
Scrimin P, Ghirlanda G, Tecilla P: Comparative reactivities of phosphate ester cleavage by metallomicelles. Langmuir 12:6235-6241, 1996.
Simanenko YS, Karpichev EA, Prokop'eva TM: Functional detergents containing an imidazole ring and typical fragments of alpha-nucleophiles
underlying micellar systems for cleavage of esters of phosphorus acid. Russ J Org Chem 40:206-218, 2004.
Szyszkowski B: Experimentelle Studien der Fiber Kapillaren Eigenschaften der Wasserigen Losungen von Fettsauren. Z Phys Chem 64:385-415,
1908.
Tiwari S, Kolay S, Ghosh KK, Kuca K, Marek J: Kinetic study of the reactions of p-nitrophenyl acetate and p-nitrophenyl benzoate with oximate
nucleophiles. Int J Chem Kinet 41:57-64, 2009a.
Tiwari S, Ghosh KK, Marek J, Kuca K: Comparative study of nucleophilic efficacy of pralidoxime towards phosphorus, sulphur and thiophosphorus
based esters. React Kinet Catal Lett 2009b, In press.
Waysbort D, McGarvey DJ, Creasy WR, Morrissey KM, Hendrickson DM, Durst HD: A decontamination system for chemical weapons agents using a liquid
solution on a solid sorbent. J Hazard Mater 161:1114-1121, 2009.
Zajicek M, Radl Z: Katalyticky vliv kationaktivniho tenzidu na hydrolyzu fosfonatu. In Sbornik Vyzkumneho ustavu 070, Brno 1979, pp. 115-129 (In
Czech).
Zakharova LY, Fedorov SB, Kudryavtseva LA, Bel'skii VE, Ivanov BE: The effect of electrolytes on the reaction rates and acid-base equilibria in
ionic micelles. Russ Chem Bull 42:1329-1333, 1993.
|
CITED
Berger J. The age of biomedicine: current trends in traditional subjects. J Appl Biomed. 9: 57-61, 2011.
|
