Synthesis and application of non-bioaccumulable fluorinated surfactants: a review

Abstract

Due to negative effects of conventional fluorinated surfactants with long perfluorocarbon chain (CxF2x+ 1, x≥7) like perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS), these conventional long perfluorocarbon chain surfactants have been restricted in many industrial applications. Nowadays, their potential non-bioaccumulable alternatives have been developed to meet the requirements of environmental sustainable development. In this paper, the recent advances of potential non-bioaccumulable fluorinated surfactants with different fluorocarbon chain structures, including the short perfluorocarbon chain, the branched fluorocarbon chain, and the fluorocarbon chain with weak points, are reviewed from the aspects of synthesis processes, properties, and structure-activity relationships. And their applications in emulsion polymerization of fluorinated olefins, handling membrane proteins, and leather manufacture also are summarized. Furthermore, the challenges embedded in the current non-bioaccumulable fluorinated surfactants are also highlighted and discussed with the hope to provide a valuable reference for the prosperous development of fluorinated surfactants. Graphical abstract

Interfaces with Fluorinated Amphiphiles: Superstructures and Microfluidics

“…Besides heteroatom‐containing or short and branched fluorous groups, [35] another type of more sustainable fluorous moiety consists of polyfluorinated groups with hydrogen atoms within the fluorinated chain [36] . Despite promising surface properties comparable to traditional fluorinated amphiphiles, sustainable fluorous moieties are more difficult to synthesize [11, 37] . A key research area of fluoroorganic chemists, which is essential for replacing the traditional persistent fluorinated amphiphiles, is to understand in more detail the fluorous properties of the many new sustainable fluorinated structures and to develop scalable synthetic procedures.…”

Grenzflächen mit fluorierten Amphiphilen: Überstrukturen und Mikrofluidik

“…Neben heteroatomhaltigen oder kurzen und verzweigten fluorierten Gruppen [35] wurden auch polyfluorierte Gruppen mit Wasserstoffatomen innerhalb der fluorierten Kette als nachhaltigere Alternative zu linearen Perfluoralkylgruppen entwickelt [36] . Trotz vielversprechender Oberflächeneigenschaften, die mit denen herkömmlicher fluorierter Amphiphile vergleichbar sind, ist die Synthese nachhaltiger fluorierter Gruppen schwieriger [11, 37] . Ein wichtiger Forschungsbereich der fluororganischen Chemie, welcher für den Ersatz herkömmlicher langlebiger fluorierter Amphiphile von entscheidender Bedeutung ist, ist das Bemühen, die Fluor‐spezifischenEigenschaften der vielen neuen nachhaltigen fluorierten Strukturen genauer zu verstehen und skalierbare Syntheseverfahren zu entwickeln.…”

Non-Ionic Fluorosurfactants for Droplet-Based in vivo Applications

“…While their ability to stabilize perfluorocarbon/water interfaces is excellent, with interfacial tensions as low as 15-20 mN m -1 , 14 they are "PFAS" which display significant bioaccumulation concerns. 15,16 Furthermore, their ionic nature promotes interactions with biomolecules and changes in pH or ionic strength can considerably alter the IFT. 14,17 Thus, these ionic fluorosurfactants are not optimal for use in biological applications.…”