Per- and polyfluoroalkyl substances (PFAS) are a class of chemicals present in a wide range of commercial and consumer products due to their water-repellency, nonstick, or surfactant properties, resulting from their chemical and thermal stability. This stability, however, often leads to persistence in the environment when they are inevitability released. We utilized microbial microcosms from wastewater treatment plant (WWTP) sludge to determine how employing different functional groups such as heteroatom linkages, varying chain lengths, and hydrofluoroethers (HFEs) will impact the ultimate fate of these novel PFAS structures. A suite of five novel fluorosurfactant building blocks (F₇C₃OCHFCF₂SCH₂CH₂OH (FESOH), F₃COCHFCF₂SCH₂CH₂OH (MeFESOH), F₇C₃OCHFCF₂OCH₂CH₂OH (ProFdiEOH), F₇C₃OCHFCF₂CH₂OH (ProFEOH), and F₃COCHFCF₂OCH₂CH₂OH (MeFdiEOH)) and their select transformation products, were incubated in WWTP aerobic microcosms to determine structure–activity relationships. The HFE alcohol congeners with a thioether (FESOH and MeFESOH) were observed to transform faster than the ether congeners, while also producing second-generation HFE acid products (F₇C₃OCHFC(O)OH (2H-3:2 polyfluoroalkyl ether carboxylic acid [PFECA]) and F₃COCHFC(O)OH (2H-1:2 PFECA). Subsequent biodegradation experiments with 2H-1:2 PFESA and 2H-1:2 PFECA displayed no further transformation over 74 days. Surface water Photofate experiments compared 2H-1:2 PFECA, and 2H-1:2 polyfluorinated ether sulfonate (PFESA) with their fully fluorinated ether acid counterparts, and demonstrated the potential for both HFE acid species to completely mineralize over extended periods of time, a fate that highlights the value of studying novel PFAS functionalization. Environ Toxicol Chem 2024;00:1–9. © 2023 The Authors. Environmental Toxicology and Chemistry published by Wiley Periodicals LLC on behalf of SETAC.

中文翻译：

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评估新型高功能化氢氟醚醇在废水处理厂微观世界和地表水中的最终归宿的比较生物降解研究

全氟烷基物质和多氟烷基物质 (PFAS) 是一类化学品，由于其化学和热稳定性而具有防水性、不粘性或表面活性剂特性，因此广泛存在于商业和消费品中。然而，当它们不可避免地被释放时，这种稳定性通常会导致它们在环境中持久存在。我们利用废水处理厂 (WWTP) 污泥中的微生物微观世界来确定使用不同的官能团（例如杂原子键、不同的链长度和氢氟醚 (HFE)）将如何影响这些新型 PFAS 结构的最终命运。一套五种新型含氟表面活性剂结构单元（F ₇ C ₃ OCHFCF ₂ SCH ₂ CH ₂ OH (FESOH)、F ₃ COCHFCF ₂ SCH ₂ CH ₂ OH (MeFESOH)、F ₇ C ₃ OCHFCF ₂ OCH ₂ CH ₂ OH (ProFdiEOH) )、F ₇ C ₃ OCHFCF ₂ CH ₂ OH (ProFEOH) 和 F ₃ COCHFCF ₂ OCH ₂ CH ₂ OH (MeFdiEOH)) 及其选择的转化产物在污水处理厂好氧微观世界中孵育，以确定结构-活性关系。观察到 HFE 醇同系物与硫醚（FESOH 和 MeFESOH）的转化速度比醚同系物更快，同时还产生第二代 HFE 酸产物（F ₇ C ₃ OCHFC(O)OH (2H-3:2 多氟烷基醚羧基)酸 [PFECA]) 和 F ₃ COCHFC(O)OH (2H-1:2 PFECA)。随后使用 2H-1:2 PFESA 和 2H-1:2 PFECA 进行的生物降解实验显示 74 天内没有进一步转化。地表水 Photofate实验将 2H-1:2 PFECA 和 2H-1:2 多氟醚磺酸盐 (PFESA) 与其完全氟化醚酸对应物进行了比较，并证明了两种 HFE 酸在较长时间内完全矿化的潜力，这种命运强调了研究新型 PFAS 功能化的价值。Environ Toxicol Chem 2024;00:1–9。© 2023 The Authors。环境毒理学和化学由 Wiley periodicals LLC 代表 SETAC 出版。