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Thioimidazolium salts as a platform for nonvolatile alkylators and degradable antiseptics

  • ABSTRACT: A collection of thioimidazolium salts were synthesized and used as a new class of nonvolatile alkylating agents. Their nonvolatility prevents exposure during use or handling and are thus drastically safer than conventional alkylating agents. We discovered that thioimidazolium Iodide salts cannot release volatile compounds in the solid state, but instead only decompose when molten. Since decomposition proceeds via alkyl iodide elimination, SN2 of iodide on the thioimidazolium cation is constrained in the solid state, and instead can occur only upon melting when ions are mobile. By smart design of these alkylators, the melting point and thus the decomposition temperature of these salts can be increased from 106 to 169 °C and release negligible volatile organic compounds prior to melting. Thioimidazolium-bis(trifluoromethanesulfonyl)imide (TFSI) ionic liquids act as a completely nonvolatile and air-stable TFSI-based alkylating agent and can be used for high-throughput SynthesisABSTRACT: A collection of thioimidazolium salts were synthesized and used as a new class of nonvolatile alkylating agents. Their nonvolatility prevents exposure during use or handling and are thus drastically safer than conventional alkylating agents. We discovered that thioimidazolium Iodide salts cannot release volatile compounds in the solid state, but instead only decompose when molten. Since decomposition proceeds via alkyl iodide elimination, SN2 of iodide on the thioimidazolium cation is constrained in the solid state, and instead can occur only upon melting when ions are mobile. By smart design of these alkylators, the melting point and thus the decomposition temperature of these salts can be increased from 106 to 169 °C and release negligible volatile organic compounds prior to melting. Thioimidazolium-bis(trifluoromethanesulfonyl)imide (TFSI) ionic liquids act as a completely nonvolatile and air-stable TFSI-based alkylating agent and can be used for high-throughput Synthesis of TFSI ionic liquids without solvent. Alkyl groups from methyl to dodecyl can be transferred to a nucleophile and the product purified by sublimation of the thione byproduct, which can then be recycled. We also found that thioimidazolium salts with a dodecyl chain are bactericidal, yet can hydrolyze in water to form benign neutral products, and thus wont accumulate in the environment. These results demonstrate that thioimidazolium salts are a designable platform for the pursuit of safer and more environmentally friendly alkylating and antiseptic agents.zeige mehrzeige weniger

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Metadaten
Autoren/innen:R. Guterman, H. Miao, V. A. Cataldo, M. Antonietti, Thomas Dimke, Ina Stephan
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):ACS sustainable chemistry and engineering
Jahr der Erstveröffentlichung:2018
Organisationseinheit der BAM:4 Material und Umwelt
4 Material und Umwelt / 4.1 Biologische Materialschädigung und Referenzorganismen
Verlag:American Chemical Society
Verlagsort:Washington, DC
Jahrgang/Band:6
Ausgabe/Heft:11
Erste Seite:15434
Letzte Seite:15440
DDC-Klassifikation:Technik, Medizin, angewandte Wissenschaften / Ingenieurwissenschaften / Sanitär- und Kommunaltechnik; Umwelttechnik
Freie Schlagwörter:Alkylating agents; Antiseptic agents; Decomposition point; Melting point; Nonvolatile; One-step ionic liquids synthesis
Themenfelder/Aktivitätsfelder der BAM:Umwelt
Umwelt / Umweltverhalten von Materialien und Produkten
Umwelt / Umweltschadstoffe
DOI:https://doi.org/10.1021/acssuschemeng.8b03874
URL:http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=Alerting&SrcApp=Alerting&DestApp=WOS_CPL&DestLinkType=FullRecord&UT=WOS:000449577200199
ISSN:2168-0485
Verfügbarkeit des Volltexts:Volltext-PDF im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:06.12.2018
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:06.12.2018