355-37-3 | 1H-PERFLUOROHEXANE

CAS:355-37-3 | 1H-PERFLUOROHEXANE,Description

1H-Perfluorohexane, as a member of the perfluorinated compounds (PFCs), is characterized by its strong carbon-fluorine bonds and resistance to degradation. It is used in various industrial applications, including surfactants and protective coatings, due to its ability to repel water and oil stains. PFCs like 1H-Perfluorohexane are globally present in the environment and have been detected in human biological samples, raising concerns about their potential impact on health and the environment.

Synthesis Analysis

The synthesis of related perfluoroalkyl compounds involves the oxidation of 1-iodo-1H,1H-perfluoroalkanes with trifluoroperacetic acid, followed by treatment with triflic acid and benzene or fluorobenzene. This method has been used to produce various (1H,1H-perfluoroalkyl)phenyl- and -(p-fluorophenyl)iodonium triflates in good yields. Additionally, (trans-1H-Perfluoro-1-alkenyl)phenyliodonium triflates can be synthesized by dehydrofluorination of these compounds with a base.

Molecular Structure Analysis

The molecular structure of perfluorinated compounds, including 1H-Perfluorohexane, is characterized by a strong carbon-fluorine bond. Gas-phase electron diffraction studies of related perfluoro compounds have revealed detailed geometric parameters, such as bond lengths and angles, which are indicative of the robust and stable nature of these molecules.

Chemical Reactions Analysis

Perfluorinated compounds exhibit unique reactivity due to the strength of the C-F bond. For instance, thermolysis of certain perfluoroalkyl iodonium triflates can produce perfluoroalkyl triflates and iodobenzene, while others yield (Z)-1-iodo-1H-perfluoro-1-alkenes and phenyl triflate. The thermal decomposition of these compounds suggests an ionic mechanism involving various cationic species.

Physical and Chemical Properties Analysis

Perfluorohexane sulfonate (PFHxS), a closely related compound to 1H-Perfluorohexane, has been identified as a persistent organic pollutant due to its long half-life in human serum and potential neurotoxicity. The physical and chemical properties of PFHxS, such as its stability and resistance to degradation, have been a significant concern. Mechanochemical degradation using zero-valent iron and ferrate(VI) has shown promise in degrading PFHxS, highlighting the potential for developing effective treatment methods for these stable compounds.

Furthermore, the toxicokinetic behavior of perfluorohexanoic acid (PFHxA) in animal models has been studied, providing insights into the systemic exposure and clearance rates of these compounds. Such studies are crucial for understanding the environmental and health impacts of perfluorinated compounds.

Lastly, the liquid structure of perfluoroalkylalkanes has been probed using 129Xe NMR spectroscopy, revealing nano-segregation and the formation of mesophases in these substances. This segregation is driven by dispersion forces, which is unusual compared to common examples determined by hydrogen bonding and polarity.

Scientific Research Applications

• Drug Encapsulation and Medical Applications : PFH has been successfully encapsulated in polymethylsilsesquioxane (PMSQ) using coaxial electrohydrodynamic atomisation (CEHDA) for medical applications. This method is suitable for preparing both micro- and nanoscale capsules. The encapsulation of a dye (Evans blue) was achieved by heating the capsules in the dye solution to vaporize the PFH core, enabling the inward diffusion of the liquid. This approach can be useful in the preparation of multicomponent and multifunctional micro- and nanoparticles (Chang, Stride, & Edirisinghe, 2009).
• Extraction Capability : PFH, as a diluent, has shown a synergistic effect on the extraction capability of 1H,1H,2H,2H-Perfluorooctan-1-ol for salicylic acid. This is supported by experimental and computational investigations. The synergistic effect is attributed to interactions through hydrogen bonds (Wu et al., 2018).
• Photoacoustic Therapy : PFH, combined with gold nanorods (AuNRs), has been used in photoacoustic therapy. Upon pulsed laser irradiation, PFH vaporization facilitates bubble implosion and shockwave generation, inducing apoptosis in cancer cells effectively (Zhong, Yang, & Xing, 2016).
• Perfluorocarbon Nanoemulsions for Cancer Therapy and Imaging : PFH nanoemulsions (PFH-NEs) have been developed as drug-delivery vehicles and contrast agents for ultrasound and photoacoustic imaging of cancer. They are small (<100 nm), stable at physiological conditions, and can be used for multimodal imaging and as drug-loaded therapeutics via endocytosis (Fernandes et al., 2016).
• Microemulsion Systems : PFH has been used in the study of aqueous microemulsion systems with the fluorinated surfactant tetraethylammonium perfluorooctylsulfonate (TEAFOS). This study observed the transition from threadlike micelles to spherical micelles solubilizing the oil, providing insights into the behavior of microemulsion systems (Johannessen, Walderhaug, & Balinov, 2004).

Safety And Hazards

1H-Perfluorohexane is generally considered safe when handled properly. However, precautions should be taken:

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• Inhalation : Avoid inhalation of vapors.
   
• Skin Contact : Minimal skin absorption, but avoid prolonged contact.
   
• Environmental Impact : Due to its persistence, proper disposal is crucial.
   

Future Directions

Research on 1H-Perfluorohexane continues to explore its applications in emerging fields such as nanotechnology, materials science, and green chemistry. Investigations into its biodegradability and potential alternatives are essential for sustainable use.

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