Studies on a macromolecular dichloroamine — the N,N‐dichloro poly(styrene‐co‐divinylbenzene) sulphonamide

Abstract

Starting from a commercial sulphonate cation-exchange resin via sulphonyl chloride and sulphonamide resins, a macromolecular dichloroamine with ca. 6 mmol of active chlorine per gram of resin was prepared. The conditions for its optimum preparation starting from poly(styrene-co-diviny1benzene)sulphonamide (poly(St-Co-DVB)SQNH,) were stated. The possibility of iterated chlorination and dechlorination of the product was proved. Its stability in the range of 20-100"C, both in the dry state and in aqueous media, was determined. Moreover, its derivatographic examinations up to 1OOO"C were performed. Examples for the use of the macromolecular dichloroamine as a polymer supported reagent for chlorination, oxidation of several organic and inorganic species and water disinfection are given. ZUS AMMENFASSUNG:Ausgehend von einem handelsublichen makropor6sen Sulfonat-Kationenaustauscher wurde Uber Sulfonylchlorid-und Sulfonamid-Harze ein hochmolekulares Dichloramin mit fast 6 mmol aktivem Chlor pro Gramm des Harzes hergestellt. Die besten Bedingungen fur den hochsten Umsatz von Poly(styro1-co-divinylbenzol) sulfonamid (Poly(St-Co-DVB)SQNH,) zum Dichloramin wurden ermittelt. Es wurde festgestellt, da8 die wiederholte Dechlorierung und Chlorierung der Produkte ohne merklichen Abbau abliiuft. Es wurde die Bestiindigkeit im Temperaturbereich von 20-100°C gemessen und zwar sowohl im trockenen Zustand als auch in wiifirigen Medien. Dartiber hinaus wurden derivatographische Messungen bis 1 OOO "C durchgefiihrt. Es werden auch Beispiele fur die Anwendung des Dichloramins als polymeres Reagenz fur Chlorierungen, Oxidationen von organischen und anorganischen Verbindungen und fur die Wasserdesinfektion gegeben.

Polymeric decontaminant 2 (N,N‐dichloropolystyrene sulfonamide): Synthesis, characterization, and efficacy against simulant of sulfur mustard

“…14,15 Our interest in polymer-supported reactions 16 and synthesis of polymeric analogues of well known halogeno-sulfonamides and their applications have been reported. 17 A macro porous poly(styrene-co-divinylbenzene) resin having N,N-dichloro sulfonamide groups [18][19][20] have been used as a polymer supported reagent for chlorination, oxidation for residual sulfides, 21 cyanides, 22 thiocyanates, 23 water disinfection, 18 and some application in synthetic organic chemistry. 24 We have already reported N,N-dichloro poly (styrene-co-divinylbenzene) sulfonamide as a polymeric decontaminant 25 for simulant of sulfur mustard but this polymer have two disadvantages, first it is insoluble in almost all solvents and secondly, it showed prolonged decontamination time.…”

Using macroporous N-chlorosulfonamide S/DVB copolymer as an aid to iron removal from water

“…Copolymers with N-chlorosulfonamide groups in sodium or hydrogen form (R/Na stands for [P]-SO 2 NClNa and R/H stands for [P]-SO 2 NClH) were prepared according to methods published in detail elsewhere [3,4,14]: As the starting material, we used Amberlyst 15 (produced by Rohm and Haas Co.), a commercially available sulfonate cation exchanger. This is a macroporous poly (S/20 % DVB) resin, which contained 4.7 mmol/g -SO 3 -groups in the dry state (the surface area 45 m 2 /g, average pore diameter 25 nm).…”

“…This is a macroporous poly (S/20 % DVB) resin, which contained 4.7 mmol/g -SO 3 -groups in the dry state (the surface area 45 m 2 /g, average pore diameter 25 nm). The product contained 2.15 mmol/g -SO 2 NClNa groups (i.e., 4.30 mequiv of active chlorine/g) and additionally 0.70 mmol/g -SO 3 Na groups. The transformation of the N-chlorosulfonamide groups from sodium to hydrogen form was achieved by treating the R/Na product with an excess of acetic acid.…”

“…Cross-linked copolymers were synthesized and investigated by D. W. Emerson [2]. We have synthesized and investigated cross-linked and macroporous sodium and hydrogen form halogene sulfonamide copolymers [3,4]. The polymeric or copolymeric derivatives of N-chlorosulfonamide compounds are known to be efficient oxidants.…”

N‐Halamines

“…Polymer-bound N-chloro-N-sodiobenzenesulfonamidate, prepared via functionalization of poly(styrene-co-divinylbenzene), and its derivatives are useful in water disinfection and in removal of cyanide from water (144)(145)(146)(147)(148)(149)(150)(151). They have also been used in kinetic and mechanistic studies of the oxidation of pentoses (152) and phenylethyl alcohols (153).…”