Strategies for synthesizing non-bioaccumulable alternatives to PFOA and PFOS

Sha, Mo; Xing, Peng; Jiang, Biao

doi:10.1016/j.cclet.2015.03.038

Cited by 40 publications

(15 citation statements)

References 34 publications

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“…They showed higher efficiency in a relatively low concentration. Surface tension of aqueous solution (γ cmc ) and critical micelle concentration (CMC) of these solutions were much lower than those of PFOA (CMC = 31.2 mmol·L −1 , γ cmc = 24.7 mN·m −1 ), which showed better surface performances than those of PFOA [18,19,20].…”

Section: Introductionmentioning

confidence: 99%

“…Given the above conclusions, novel fluorine-containing acrylate polymers were designed and synthesized from perfluoro-2-methyl-2-pentene based on fluoro-olefin double bond reactive site, which was regarded less toxic, and hence, minimizing bio-accumulation risks associated with C-8 fluoro-compounds [18,19,20]. The repellency and thermodynamic properties of the polymers were investigated to explore the relationship between structure and performance.…”

Section: Introductionmentioning

confidence: 99%

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Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating

et al. 2018

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A new structural fluorine-containing methacrylate monomer CH2=C(CH3)COOC–(CF3)2CF2CF2CF3 (5) was synthesized derived from perfluoro-2-methyl-2-pentene (D2). A homopolymer of 5 and copolymers of 5 and methacrylate with different alkyl chain length (chain length n = 1, 2, 4, 6, 8, 12, 18) were obtained. These new fluorinated acrylate polymers showed excellent water and oil repellency. The contact angle of the films of the homopolymer and part of the copolymers were similar with the corresponding polymers prepared from CH2=CHC(O)OCH(C3F7)(CF(CF3)2), but greater than that of the C6F13(CF3)CHOC(O)CH=CH2 homopolymer. The structure-property relationship research indicated that the copolymers’ hydrophobicity decreased first and then increased with the increase of alkyl chain length. Td of all the polymers were greater than 220 °C and Tg fluctuated within the range of −51~103.8 °C. Contact angle and Tg could be adjusted by controlling the feed ratio of monomer to meet the requirements of technical indicators in the practical applications. The outstanding liquid repellency and thermal stability make monomer 5 a promising alternative to perfluorinated long-chain fluorosurfactants.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating

et al. 2018

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“…The OBS was produced at a volume of 3500 tones per year in China and has been widely used as an additive in film-forming fluoroprotein foams (FFFPs) and alcohol-resistant foams (AFFF-AR/FFFP-AR) and as a surfactant for improving oil production . Unlike PFCAs and PFSAs which have been synthesized by electrochemical fluorination and/or telomerization, OBS is produced by oligomerization, in which hexafluoropropylene trimer (HFPT) is an important starting material. − The synthesis process was shown in SI Figure S1. Although four isomers for HFPT oligomer (HFPT-a′, b′, c′, and d′ shown in SI Figure S2) have been reported, HFPT-c′ exhibits much higher reactivity than the other three isomers .…”

Section: Introductionmentioning

confidence: 99%

Discovery of a Novel Polyfluoroalkyl Benzenesulfonic Acid around Oilfields in Northern China

Shi

et al. 2017

Environ. Sci. Technol.

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The existence of more than 3000 per- and polyfluoroalkyl substances (PFASs) on the global market has prompted the identification and hazard characterization of hitherto unknown PFASs. In the present study, a novel PFAS, sodium p-perfluorous nonenoxybenzenesulfonate (OBS), was identified using Orbitrap MS/MS in water samples around a suspected application area, Daqing Oilfield, China. The peak OBS concentration was 3.2 × 10 ng/L in a sample taken near the oil well with the longest production history in Daqing. The concentrations of OBS and contribution to the sum of PFASs in surface waters displayed considerable variation among the three sampling areas (mean levels at 6.9, 50, and 5.6 × 10 ng/L with mean percentages at 9.8%, 45%, and 69% in the background, new and old oilfield areas respectively) confirming that the density of oil wells and the oil production history are important factors influencing OBS contamination in the studied areas. A preliminary assessment of acute toxicity and environmental fate indicates that OBS exhibits similar toxicity and environmental persistence to perfluorooctanesulfonic acid (PFOS). The widespread occurrence of OBS, in conjunction with its potential hazard properties, underscores the need to further study on the bioaccumulation and potential for human exposure.

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“…Unfortunately, studies had confirmed that fluorocarbon surfactants (PFOS or their derivatives), the key component of AFFF, were persistent chemicals that were easily accumulated in the blood of humans and other animals (X. H. Jia, 2015;Liu et al, 2013;Schuster et al, 2013Schuster et al, , 2014Sha et al, 2015b;Tan et al, 2005;Ye, 2000). Specifically, these substances would not be degraded by enzymes or metabolic decomposition, and the half-life of fluorocarbon surfactants would increase by 2.8-3.8 years for each additional carbon atom in the perfluoroalkyl chain (Martin et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Study on aqueous film‐forming foam extinguishing agent based on fluorocarbon cationic–hydrocarbon anionic surfactants mixture system

Yang

Peng

Sha

et al. 2021

J Surfact & Detergents

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Fluorocarbon surfactants were the main components of aqueous film-forming foam extinguishing agents (AFFF). Unfortunately, the widely used fluorocarbon surfactant perfluorooctane sulfonate (PFOS) was limited due to its toxicity, bioaccumulation and biodegradability. In this paper, an environmentally friendly quaternary ammonium cationic fluorocarbon surfactant with high surface activity and simple synthesis route was reported. The surface performance and aggregation behavior of the mixed solution of this fluorocarbon surfactant and sodium n-octyl sulfate were studied by means of surface tension meter and transmission electron microscope (TEM). The results showed that the synergistic effect of sodium n-octyl sulfate and this fluorocarbon surfactant was significant, and many vesicles could be observed in the mixed solution with the concentration of 0.1 mol/L under TEM. Subsequently, three environmental friendly AFFF formulations (F-1, F-2, F-3) were designed with the mixture of the fluorocarbon surfactant, sodium n-octyl sulfate and lauryl betaine BS-12 as foaming agent. Through its foam performance test, it could be seen that F-3 showed relatively excellent foam performance. The initial foam height h 0 was 70 mm, the 25% drainage time was 315 s, the extinguishing time was 28 s, and the burn-back time was 720 s. This kind of fire extinguishing agent had the potential of fire protection application.

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Strategies for synthesizing non-bioaccumulable alternatives to PFOA and PFOS

Cited by 40 publications

References 34 publications

Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating

Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating

Discovery of a Novel Polyfluoroalkyl Benzenesulfonic Acid around Oilfields in Northern China

Study on aqueous film‐forming foam extinguishing agent based on fluorocarbon cationic–hydrocarbon anionic surfactants mixture system

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