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RESEARCH PRODUCT

Acid Catalysis with Alkane/Water Microdroplets in Ionic Liquids

Gonzalo AbellánAntonio Doménech-carbóAndreas HirschMiguel ÁNgel Rivero-crespoVicent LloretRossella GrecoAntonio Leyva-pérez

subject

UNESCO::QUÍMICAInorganic chemistryAlkylation010402 general chemistry:QUÍMICA [UNESCO]01 natural sciencesArticleIonCatalysisAcid catalysischemistry.chemical_compoundFriedel−Crafts reactionMicroemulsionLewis acids and basesFriedel-Crafts reactionQD1-999Alkanechemistry.chemical_classification010405 organic chemistryWater microdropletsAlkane microemulsionsIonic liquids3. Good health0104 chemical sciencesAcid catalysisChemistrychemistryIonic liquidddc:547

description

Ionic liquids are composed of an organic cation and a highly delocalized perfluorinated anion, which remain tight to each other and neutral across the extended liquid framework. Here we show that n-alkanes in millimolar amounts enable a sufficient ion charge separation to release the innate acidity of the ionic liquid and catalyze the industrially relevant alkylation of phenol, after generating homogeneous, self-stabilized, and surfactant-free microdroplets (1–5 μm). This extremely mild and simple protocol circumvents any external additive or potential ionic liquid degradation and can be extended to water, which spontaneously generates microdroplets (ca. 3 μm) and catalyzes Brönsted rather than Lewis acid reactions. These results open new avenues not only in the use of ionic liquids as acid catalysts/solvents but also in the preparation of surfactant-free, well-defined ionic liquid microemulsions.

https://doi.org/10.1021/jacsau.1c00107