Synthesis of environmentally relevant fluorinated surfactants—a review

Lehmler, Hans‐Joachim

doi:10.1016/j.chemosphere.2004.11.078

Cited by 320 publications

(186 citation statements)

References 159 publications

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“…Many perfluorocarbon compounds are synthesized by an electrochemical fluorination process (Lehmler, 2005). Perfluorocarbon compounds synthesized by this route are typically highly impure and, besides containing various organofluorine compounds, can contain trace amounts of toxic inorganic impurities such as heavy metals.…”

Section: Purity and Cytotoxic Effect Of Neat Pfobmentioning

confidence: 99%

Synthesis, physicochemical properties and in vitro cytotoxicity of nicotinic acid ester prodrugs intended for pulmonary delivery using perfluorooctyl bromide as vehicle

Lehmler

Vyas

et al. 2008

International Journal of Pharmaceutics

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This study explores perfluorooctyl bromide (PFOB) as a potential vehicle for the pulmonary delivery of a series of prodrugs of nicotinic acid using cell culture studies. The prodrugs investigated have PFOB-water (log K p = 0.78 to > 2.2), perfluoromethylcyclohexane-toluene (log K p = −2.62 to 0.13) and octanol-water (log K p = 0.90 to 10.2) partition coefficients spanning several orders of magnitude. In confluent NCI-358 human lung cancer cells, the toxicity of prodrugs administered in culture medium or PFOB depends on the medium of administration, with EC20's above 8 mM and 2.5 mM for culture medium and PFOB, respectively. Short-chain nicotinates administered both in PFOB and medium increase cellular NAD/NADP levels at 1 mM nicotinate concentrations. Long-chain nicotinates, which could not be administered in medium due to their poor aqueous solubility, increased NAD/NADP levels if administered in PFOB at concentrations ≥ 10 mM. These findings suggest that even highly lipophilic prodrugs can partition out of the PFOB phase into cells, where nicotinic acid is released and converted to NAD. Thus, PFOB may be a novel and biocompatible vehicle for the delivery of lipophilic prodrugs of nicotinic acid and other drugs directly to the lung of laboratory animals and humans.

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Section: Purity and Cytotoxic Effect Of Neat Pfobmentioning

confidence: 99%

Synthesis, physicochemical properties and in vitro cytotoxicity of nicotinic acid ester prodrugs intended for pulmonary delivery using perfluorooctyl bromide as vehicle

Lehmler

Vyas

et al. 2008

International Journal of Pharmaceutics

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“…Perfluorooctanesulfonic acid (PFOS) and related compounds have been used for over 50 years in various large scale technical applications such as fire extinguishing media and in consumer products such as stain-repellent coatings on carpets, paper or fabrics [1][2][3]. These multifaceted applications of PFOS and other perfluorinated surfactants utilize an unusual combination of properties such as thermal, chemical and biological inertness, excellent spreading characteristics, and high surface activity.…”

Section: Introductionmentioning

confidence: 99%

Mixing of perfluorooctanesulfonic acid (PFOS) potassium salt with dipalmitoyl phosphatidylcholine (DPPC)

Lehmler

Xie

Bothun

et al. 2006

Colloids and Surfaces B: Biointerfaces

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Perfluorooctane-1-sulfonic acid (PFOS) is emerging as an important persistent environmental pollutant. To gain insight into the interaction of PFOS with biological systems, the mixing behavior of dipalmitoylphosphatidylcholine (DPPC) with PFOS was studied using differential scanning calorimetry (DSC) and fluorescence anisotropy measurements. In the DSC experiments the onset temperature of the DPPC pretransition (T p ) decreased with increasing PFOS concentration, disappearing at X DPPC ≤ 0.97. The main DPPC phase transition temperature showed a depression and peak broadening with increasing mole fraction of PFOS in both the DSC and the fluorescence anisotropy studies. From the melting point depression in the fluorescence anisotropy studies, which was observed at a concentration as low as 10 mg/L, an apparent partition coefficient of K = 5.7 × 10 4 (mole fraction basis) was calculated. These results suggest that PFOS has a high tendency to partition into lipid bilayers. These direct PFOS-DPPC interactions are one possible mechanism by which PFOS may contribute to adverse effects, for example neonatal mortality, in laboratory studies and possibly in humans.

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“…They are reaction products synthesized from telomerization process by iodine pentafluoride reacting with unsaturated taxogen molecules such as tetrafluoroethylene and ethylene. PFIs are used as important industrial intermediates for the production of various PFCs, such as fluorotelomer alcohols, olefins and acrylate monomers [2,13]. Since the usage of electrochemical fluorination method has been terminated since 2002 in most countries, the telomerization process has been increasingly popular in the production of PFCs.…”

Section: Introductionmentioning

confidence: 99%

Trace determination of airborne polyfluorinated iodine alkanes using multisorbent thermal desorption/gas chromatography/high resolution mass spectrometry

Ruan

Wang

Zhang

et al. 2010

Journal of Chromatography A

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a b s t r a c tA novel gas chromatography/high resolution mass spectrometry method coupled with multisorbent thermal desorption cartridges has been developed for the determination of volatile neutral polyfluorinated iodine alkanes (PFIs) in airborne samples. It allows, for the first time, simultaneous analysis of four mono-iodized perfluorinated alkanes, three diiodized perfluorinated alkanes and four mono-iodized polyfluorinated telomers in ambient air samples. 3.75 L air sample was passed through a sorbent tube packed with 150 mg of Tenax TA and 200 mg of Carbograph 1TD for analyte adsorption. Important factors during the analysis procedures, such as safe sampling volume, air sampling rate, analyte desorption and transfer strategies, were optimized and good thermal desorption efficiencies were obtained. The method detection limit (MDL) concentration ranged from 0.04 pg/L for 1H,1H,2H,2H-perfluorododecyl iodide to 1.2 pg/L for perfluorohexyl iodide, and instrument response of a seven-point calibration was linear in the range of 10-1000 pg. Travel spike recoveries ranged from 83% to 116%. Small variabilities of less than 36% were obtained near the MDLs and the differences between triplicates were even smaller (2.1-7.3%) at 200 pg spiked level. The method was successfully applied to analyze ambient air samples collected near a point source, and five PFIs were identified (10.8-85.0 pg/L), with none of the analytes detectable at the background site.

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Synthesis of environmentally relevant fluorinated surfactants—a review

Cited by 320 publications

References 159 publications

Synthesis, physicochemical properties and in vitro cytotoxicity of nicotinic acid ester prodrugs intended for pulmonary delivery using perfluorooctyl bromide as vehicle

Synthesis, physicochemical properties and in vitro cytotoxicity of nicotinic acid ester prodrugs intended for pulmonary delivery using perfluorooctyl bromide as vehicle

Mixing of perfluorooctanesulfonic acid (PFOS) potassium salt with dipalmitoyl phosphatidylcholine (DPPC)

Trace determination of airborne polyfluorinated iodine alkanes using multisorbent thermal desorption/gas chromatography/high resolution mass spectrometry

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