Synthesis and emission of active chlorine from immobilized N-chloro-N-alkylsulfonamides
DOI:
https://doi.org/10.15587/2313-8416.2016.66881Keywords:
active chlorine, emission, N-alkylsulfonamides, Taurine, N-chlorotaurine, N, N-dichlorotaurine, immobilized N-chloro-N-alkylsulfonamide, antimicrobial activity, IR-spectra, UV-spectraAbstract
Aim. To synthesize immobilized N-chloro-N-alkylsulfonamides with different lengths alkyl radicals, to study their properties and emission of active chlorine from them upon activation.
Methods. Immobilized N-alkylsulfonamides were synthesized by reaction of immobilized on a styrene-divinylbenzene copolymer (8 % of divinylbenzene) sulfochloride with amines, e.g.: Methylamine, Ethylamine, n-Propylamine, n-Butylamine, Cyclohexylamine, n-Dodecylamine. Immobilized N-chloro-N-alkylsulfonamides were obtained after their reaction with Sodium hypochlorite. Active chlorine emission from the synthesized substances into the Taurine – containing aqueous solutions was studied.
Results. It has been shown, that the content of active chlorine in N-chloro-N-alkylsulfonamides decreases symbatically with increasing length of the alkyl radical. Upon increasing length of the alkyl substituent in the polymer matrix, quantity of N-alkylsulfonamide groups, not reacting with Sodium hypochlorite due to steric hindrance generated by alkyl groups, decreases.
Immobilized N-chloro-N-alkylsulfonamides upon their activation by Taurine are more stable in aqueous solutions in comparison with analogous Sodium N-chloro sulfonamides. After 24 hours, active chlorine pseudo-equilibrium is achieved and remains stable within 192 hours. Active chlorine achieved concentration upon activation is 40–130 mg/dm3, depending on alkyl radical. N-chlorotaurine – N, N-dichlorotaurine equilibrium in solution was studied by UV-spectroscopy method. Antimicrobial properties of the solution, produced from the immobilized N-chloro-N- (n-propyl) sulfonamide, were studied.
Conclusion. Active chlorine content in immobilized N-chloro-N-alkylsulfonamides decreases symbatically with increasing length of the alkyl radical.
Immobilized N-chloro-N-alkylsulfonamides show a significant resistance to the Taurine effect comparing with corresponding Sodium N-chloro sulfonamides. In relation to the activator – Taurine, the difference between immobilized N-chloro-N-alkylsulfonamides and Sodium N-chloro sulfonamides is connected with distinctions in the structure of –SO2NAlkCl and –SO2NNaCl fragments, as well as N–CI binding energy.
Immobilized N-chloro-N-alkylsulfonamides can be used as a prolonged action active chlorine sources
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Copyright (c) 2016 Владимир Николаевич Торопин, Константин Сергеевич Бурмистров, Богдан Валериевич Мурашевич, Геннадий Николаевич Кременчуцкий
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