Health & Environmental Research Online (HERO)


PFDoA (307-55-1)


4 References Were Found:

Technical Report
Technical Report

Safety data sheet. Version 4.5. Tricosafluorododecanoic acid. Product number 406449. CAS-No. 307-55-1

Author: Sigma-Aldrich (2017) HERO ID: 3980877


Book/Book Chapter
Book/ Chapter

Fluorine compounds, organic

Authors: Siegemund, G; Schwertfeger, W; Feiring, A; Smart, B; Behr, F; Vogel, H; McKusick, B; Kirsch, P (2016) In Ullmann's encyclopedia of industrial chemistry. online: John Wiley and Sons, Inc. HERO ID: 3980878

[Less] Organic fluorine compounds are characterized by their carbon–fluorine bond. Fluorine can replace any . . . [More] Organic fluorine compounds are characterized by their carbon–fluorine bond. Fluorine can replace any hydrogen atom in linear or cyclic organic molecules because the difference between the van der Waals radii for hydrogen (0.12 nm) and fluorine (0.14 nm) is small compared to that of other elements (e.g., chlorine 0.18 nm). Thus, as in hydrocarbon chemistry, organic fluorine chemistry deals with a great variety of species. When all valences of a carbon chain are satisfied by fluorine, the zig-zagshaped carbon skeleton is twisted out of its plane in the form of a helix. This situation allows the electronegative fluorine substituents to envelop the carbon skeleton completely and shield it from chemical (especially nucleophilic) attack. Several other properties of the carbon–fluorine bond contribute to the fact that highly fluorinated alkanes are the most stable organic compounds. These include low polarizability and high bond energies, which increase with increasing substitution by fluorine (bond energies: C–F bond in CH3F, 448 kJ/mol; C–H bond in CH4, 417 kJ/mol; C–Cl bond in CH3Cl, 326 kJ/mol; and C–F bond in CF4, 486 kJ/mol).

The cumulative negative inductive effect of the fluorine in perfluoroalkyl groups may reverse the polarity of adjacent single bonds (e.g., in the pair H3C ◅ I and F3C ▻ I) or double bonds (e.g., CH3Cδ‡H ˆ CδH2 and CF3 CδH ˆ Cδ‡H2). Fluorine substitution changes the reactivity of olefins and carbonyl compounds. Polyfluorinated olefins possess an electron-deficient double bond, which reacts preferentially with nucleophiles. Carboxy groups are affected by the presence of an adjacent perfluoroalkyl radical. In carboxylic acids, the acidity is markedly increased. In other carbonyl compounds, the reactivity is increased without any fundamental change in the chemistry of the compound. Correspondingly, the basicity of amines is reduced by the introduction of fluorine. Fluorine attached to the ring of aromatic compounds acts mainly as a paradirecting substituent, whereas perfluoroalkyl groups behave as meta-directing substituents.

Naturally, the influence of fluorine is greatest in highly fluorinated and perfluorinated compounds. The fact that these compounds have a high thermal stability and chemical resistance and are physiologically inert makes them suitable for many applications for which hydrocarbons are not. Properties that are exploited commercially include high thermal and chemical stability, low surface tension, and good dielectric properties, for example, in fluoropolymers, perfluorinated oils and inert fluids.

Individual fluorine atoms or perfluoroalkyl groups do not change the technical properties of a hydrocarbon fundamentally. However, this is not the case with physiological properties. A fluorine atom in a bioactive material may simulate a hydrogen atom, and although this does not prevent metabolic processes from occurring, the end products may be ineffective or toxic. Accordingly, such fluorine compounds are important in, for example, pesticides and pharmaceuticals.

A general overview of the scientific literature on organofluorine chemistry was published in 2013 [1]; commercial applications of fluorine products are reviewed in [2–4].

The "refereed" or "peer review" status of a journal comes from the Ulrichsweb Global Serials Directory (http://ulrichsweb.serialssolutions.com/), as supplied by the publisher. The term refers to the system of critical evaluation of manuscripts/articles by professional colleagues or peers. The content of refereed publications is sanctioned, vetted, or otherwise approved by a peer-review or editorial board. The peer-review and evaluation system is utilized to protect, maintain, and raise the quality of scholarly material published in serials. Publications subject to the referee process are assumed, then, to contain higher quality content than those that are not.
Peer Reviewed Journal Article

Prediction of aqueous solubility, vapor pressure and critical micelle concentration for aquatic partitioning of perfluorinated chemicals

Authors: Bhhatarai, B; Gramatica, P (2011) Environmental Science and Technology 45:8120-8128. HERO ID: 3980826

[Less] The majority of perfluorinated chemicals (PFCs) are of increasing risk to biota and environment due . . . [More] The majority of perfluorinated chemicals (PFCs) are of increasing risk to biota and environment due to their physicochemical stability, wide transport in the environment and difficulty in biodegradation. It is necessary to identify and prioritize these harmful PFCs and to characterize their physicochemical properties that govern the solubility, distribution and fate of these chemicals in an aquatic ecosystem. Therefore, available experimental data (10-35 compounds) of three important properties: aqueous solubility (AqS), vapor pressure (VP) and critical micelle concentration (CMC) on per- and polyfluorinated compounds were collected for quantitative structure-property relationship (QSPR) modeling. Simple and robust models based on theoretical molecular descriptors were developed and externally validated for predictivity. Model predictions on selected PFCs were compared with available experimental data and other published in silico predictions. The structural applicability domains (AD) of the models were verified on a bigger data set of 221 compounds. The predicted properties of the chemicals that are within the AD, are reliable, and they help to reduce the wide data gap that exists. Moreover, the predictions of AqS, VP, and CMC of most common PFCs were evaluated to understand the aquatic partitioning and to derive a relation with the available experimental data of bioconcentration factor (BCF).

The "refereed" or "peer review" status of a journal comes from the Ulrichsweb Global Serials Directory (http://ulrichsweb.serialssolutions.com/), as supplied by the publisher. The term refers to the system of critical evaluation of manuscripts/articles by professional colleagues or peers. The content of refereed publications is sanctioned, vetted, or otherwise approved by a peer-review or editorial board. The peer-review and evaluation system is utilized to protect, maintain, and raise the quality of scholarly material published in serials. Publications subject to the referee process are assumed, then, to contain higher quality content than those that are not.
Peer Reviewed Journal Article

The pKa values of PFOA and other highly fluorinated carboxylic acids

Author: Goss, KU (2008) Environmental Science and Technology 42:456-458. HERO ID: 3980872

[Less] The dissociated and nondissociated species of any organic acid differ largely in their physicochemical . . . [More] The dissociated and nondissociated species of any organic acid differ largely in their physicochemical behavior. The ratio of both species in aqueous systems is determined by the respective pKa value. For perfluorooctanoic acid recent fate-modeling studies have applied a pKa value of 2.8. This value likely is too high by 3 log units. Here, the correct value is estimated to be close to -0.5 based on analogy considerations and molecular modeling. Calculated pKa values for other highly fluorinated carboxylic acids are also presented.