Synthesis and characterization of tri-block fluorinated-n-alkanes

Conte, L.; Zaggia, Alessandro; Sassi, Alain; Seraglia, Roberta

doi:10.1016/j.jfluchem.2006.12.016

Cited by 16 publications

(11 citation statements)

References 32 publications

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“…The solid state structure of 2 has not been previously reported, although it has been characterized by powder diffraction 46 and thermal techniques. 47 In line with the powder diffraction study we have observed two different polymorphs; 48 only one gave a solution, which corresponds to the β-polymorph, and is shown in Figure 2a. The bond lengths and angles are collated in the Supporting Information (Table S1).…”

Section: ' Results and Discussionsupporting

confidence: 78%

“…This has not been fully characterized by NMR spectroscopy before, so we have included complete NMR data in the Experimental Section. The solid state structure of 2 has not been previously reported, although it has been characterized by powder diffraction and thermal techniques . In line with the powder diffraction study we have observed two different polymorphs; only one gave a solution, which corresponds to the β-polymorph, and is shown in Figure a.…”

Section: Resultsmentioning

confidence: 99%

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Fluorine–Fluorine Interactions in the Solid State: An Experimental and Theoretical Study

et al. 2011

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The solid state structures of three compounds that contain a perfluorinated chain, CF(3)(CF(2))(5)CH(2)CH(CH(3))CO(2)H, CF(3)(CF(2))(5)(CH(2))(4)(CF(2))(5)CF(3) and {CF(3)(CF(2))(5)CH(2)CH(2)}(3)P═O have been compared and a number of C-F···F-C and C-F···H-C interactions that are closer than the sum of the van der Waals radii have been identified. These interactions have been probed by a comprehensive computational chemistry investigation and the stabilizing energy between dimeric fragments was found to be 0.26-29.64 kcal/mol, depending on the type of interaction. An Atoms-in-Molecules (AIM) study has confirmed that specific C-F···F-C interactions are indeed present, and are not due simply to crystal packing. The weakly stabilizing nature of these interactions has been utilized in the physisorption of a selected number of compounds containing long chain perfluorinated ponytails onto a perfluorinated self-assembled monolayer, which has been characterized by IRRAS (Infrared Reflection Absorption Spectroscopy).

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Section: ' Results and Discussionsupporting

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Fluorine–Fluorine Interactions in the Solid State: An Experimental and Theoretical Study

et al. 2011

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“…The volume of the blood extract was adjusted to 200 µL using nitrogen. Performance standard 13 C 5 -PFNA and 300 µL of 2 mM ammonium acetate in water were added prior to analysis. Analysis was performed using an Acquity UPLC coupled to a Quattro Premier XE (Waters Corp.) with an atmospheric electrospray interface operating in negative ion mode (ES-MS/MS).…”

Section: Introductionmentioning

confidence: 99%

A Time Trend Study of Significantly Elevated Perfluorocarboxylate Levels in Humans after Using Fluorinated Ski Wax

Nilsson

Kärrman

Westberg

et al. 2010

Environ. Sci. Technol.

119

113

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A time trend study focusing on ski waxing technicians' exposure to perfluorinated chemicals (PFCs) from fluorinated wax fumes was performed in 2007/2008. Levels of eight perfluorocarboxylates and three perfluorosulfonates were analyzed in monthly blood samples from eight technicians. Samples were collected before the ski season, i.e., preseason, then at four FIS World Cup competitions in cross country skiing, and finally during an unexposed 5-month postseason period. The perfluorinated carboxylates perfluoroheptanoic acid (PFHpA), perfluorooctanoic acid (PFOA), perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA), and perfluoroundecanoic acid (PFUnDA) bioaccumulate, and continued exposure may contribute to elevated levels in ski technicians compared to the general population. The wax technicians' median blood level of PFOA is 112 ng/mL compared to 2.5 ng/mL in the general Swedish population. A significant correlation was found between number of working years and levels of perfluorocarboxylates. The PFOA levels in three technicians with "low" initial levels of PFOA (<10.0 ng/mL in preseason blood) increased by 254, 134, and 120%, whereas five technicians with "high" initial levels (>100 ng/mL in preseason sample) were at steady state. PFHxA is suggested to have a short half-life in humans relative the other perfluorocarboxylates. The levels of perfluorosulfonates were unaffected by the wax exposure.

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“…Cross-country skis, downhill skis, and snowboards are all optimized for maximum speed using glide waxes. The exact contents of the waxes are seldom disclosed by the manufacturers, but wax analyses show that most of the gliders available on the market contain semifluorinated n-alkanes (SFAs) and PFCAs (15). The estimated annual production of kick and glide wax is 275 tonnes globally, calculation based on information from Swix stating that their production of 110 tonnes represents 40% share of the ski wax market worldwide (16).…”

Section: Introductionmentioning

confidence: 99%

Inhalation Exposure to Fluorotelomer Alcohols Yield Perfluorocarboxylates in Human Blood?

Nilsson

Kärrman

Rotander

et al. 2010

Environ. Sci. Technol.

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Levels of perfluorinated carboxylates (PFCAs) in different environmental and biological compartments have been known for some time, but the routes of exposure still remain unclear. The opinions are divergent whether the exposure to general populations occurs mainly indirect through precursor compounds or direct via PFCAs. Previous results showed elevated blood levels of PFCAs in ski wax technicians compared to a general population. The objective of this follow-up study was to determine concentrations of PFCAs, perfluorosulfonates (PFSAs), and fluorotelomer alcohols (FTOHs), precursor compounds that are known to degrade to PFCAs, in air collected in the breathing zone of ski wax technicians during work. We collected air samples by using ISOLUTE ENV+ cartridges connected to portable air pumps with an air flow of 2.0 L min(-1). PFCAs C5-C11 and PFSAs C4, C6, C8, and C10 were analyzed using LC-MS/MS and FTOHs 6:2, 8:2, and 10:2 with GC-MS/MS. The results show daily inhalation exposure of 8:2 FTOH in μg/m(3) air which is up to 800 times higher than levels of PFOA with individual levels ranging between 830-255000 ng/m(3) air. This suggests internal exposure of PFOA through biotransformation of 8:2 FTOH to PFOA and PFNA in humans.

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Synthesis and characterization of tri-block fluorinated-n-alkanes

Cited by 16 publications

References 32 publications

Fluorine–Fluorine Interactions in the Solid State: An Experimental and Theoretical Study

Fluorine–Fluorine Interactions in the Solid State: An Experimental and Theoretical Study

A Time Trend Study of Significantly Elevated Perfluorocarboxylate Levels in Humans after Using Fluorinated Ski Wax

Inhalation Exposure to Fluorotelomer Alcohols Yield Perfluorocarboxylates in Human Blood?

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