Phase-out-compliant fluorosurfactants

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en Hummel, M. Markiewicz, M. Stolte, S. Noisternig, Michael Braun, D. E. Gelbrich, Thomas Griesser, Ulrich J. Partl, G. Naier, B. Wurst, Klaus Krüger, B. Kopacka, Holger Laus, G. Huppertz, H. Schottenberger, H. 2018-12-21T10:28:31Z 2018-12-21T10:28:31Z 2017
dc.identifier.citation Hummel , M , Markiewicz , M , Stolte , S , Noisternig , M , Braun , D E , Gelbrich , T , Griesser , U J , Partl , G , Naier , B , Wurst , K , Krüger , B , Kopacka , H , Laus , G , Huppertz , H & Schottenberger , H 2017 , ' Phase-out-compliant fluorosurfactants : Unique methimazolium derivatives including room temperature ionic liquids ' , Green Chemistry , vol. 19 , no. 14 , pp. 3225-3237 . en
dc.identifier.issn 1463-9262
dc.identifier.other PURE UUID: 14db5383-6e9c-46fa-88f3-ee84bbfe4224
dc.identifier.other PURE ITEMURL:
dc.identifier.other PURE LINK:
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dc.description.abstract Expedient alkylations of 1-methyl-3H-imidazole-2-thione, a pharmaceutical active ingredient available in bulk quantities, provide high yield access to numerous protonated, or quaternized imidazoliums with chemospecific attachment of the fluoroponytail at the 2-mercapto functionality. The deprotonated primary target products represent valuable nitrogen heterocyclic bases, capable of further substitution, and salt or complex formation. Specific physicochemical characteristics that are relevant for phase and surface responsive behavior, e.g. critical micelle concentration, oleophobicity, depression of the aqueous surface tension, foam formation, emulsification of microgranular PTFE, are investigated for selected representatives and compared to the properties of common fluorosurfactants and ionic liquids. Remarkably, it is found that halogen bonding between iodide counterions of respective polyfluoroalkylmethimazolium systems and 1-iodoperfluoroalkanes, serving as the σ-hole partner of the halides, greatly affectthe solubility profile of the resulting molecular adducts. Single-crystal X-ray structure determinations are carried out across the new fluorous substance classes. Strikingly, the helical arrangement of fluorine atoms along the chains typically encountered in polyfluorinated compounds is not found as the prevailing conformation. Rather, they are outnumbered by structural motifs exhibiting the rare zig-zag (linear alkane-like) chain conformation. Key derivatives are also subjected to preliminary ecotoxicological testing. en
dc.format.extent 13
dc.format.extent 3225-3237
dc.format.mimetype application/pdf
dc.language.iso en en
dc.relation.ispartofseries Green Chemistry en
dc.relation.ispartofseries Volume 19, issue 14 en
dc.rights openAccess en
dc.subject.other Environmental Chemistry en
dc.subject.other Pollution en
dc.subject.other 1182 Biochemistry, cell and molecular biology en
dc.title Phase-out-compliant fluorosurfactants en
dc.type A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä fi
dc.description.version Peer reviewed en
dc.contributor.department Department of Bioproducts and Biosystems
dc.contributor.department University of Bremen
dc.contributor.department Innsbruck Medical University
dc.subject.keyword Environmental Chemistry
dc.subject.keyword Pollution
dc.subject.keyword 1182 Biochemistry, cell and molecular biology
dc.identifier.urn URN:NBN:fi:aalto-201812216624
dc.identifier.doi 10.1039/c7gc00571g
dc.type.version acceptedVersion info:eu-repo/date/embargoEnd/2017-04-04

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