Design, synthesis and surfactant properties of perfluorobutyl-based fluorinated sodium alkanesulfonates

Chirumarry, Sridhar; Rao, V. Raghavender; Ko, Yohan; Vijaykumar, B.V.D.; Lim, Jae‐Min; Kim, Hyundon; Han, Sang-Chul; Jang, Kiwan; Shin, Dong‐Soo

doi:10.1016/j.jfluchem.2017.04.003

Cited by 17 publications

(9 citation statements)

References 19 publications

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“…Thus triethylamine was excessive as 1.1 molars to 1H,2H,2H−Perfluorohexan‐1‐ol. Analogous exothermic sulfonation cases proceed under mild conditions [61,62] . The second reaction was directed towards the protonation of 1‐methylimidazole, with a concomitant occurrence of the linkage between the hydrophilic and hydrophobic moieties.…”

Section: Resultsmentioning

confidence: 99%

“…Analogous exothermic sulfonation cases proceed under mild conditions. [61,62] The second reaction was directed towards the protonation of 1-methylimidazole, with a concomitant occurrence of the linkage between the hydrophilic and hydrophobic moieties. Owing to the tunable of the imidazole ring, the 3-positon N substitution was readily used to construct hydrophilic structure under proper conditions, especially in synthesizing hydrocarbon chain surfactants.…”

Section: Discussion Of Preparation Processmentioning

confidence: 99%

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Synthesis and Characterization of a Novel Imidazolium Short‐Chain Fluorocarbon Surfactant as a Potential Agent for Aqueous Film Forming Foam

Wang,

Bai,

Zhu

et al. 2023

ChemistrySelect

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To explore novel hydrophilic groups of short‐chain fluorocarbon surfactants for aqueous film‐forming foam (AFFF), an original surfactant (S‐im) with a unique imidazolium structure was developed. The intermediate and S‐im were identified by FT‐IR and NMR, validating the mild synthesis route. MS spectrum correspondingly verified the molecular weight of S‐im (329.07). TGA analysis further revealed that S‐im showed satisfied thermal stability before 200 °C. Due to the synergism effect, equimolar S‐im/C6H13NaO3S (6.29 mmol/L) maintained a low surface tension of 17.81 mN/m. Likewise, the high surface activity of the equimolar mixture contributed to its spreading on different hydrocarbon fuels. We adjusted the mixture concentration to 20 mmol/L based on applicable standards to obtain a moderate foam expansion (9.7) and an opportune drained time (323 s). The mixture exerted a promising performance. All flames caused by investigated fuels were extinguished in 75 seconds, with burnback time exceeding 14 minutes, indicating a significant field application potential.

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Section: Resultsmentioning

confidence: 99%

Section: Discussion Of Preparation Processmentioning

confidence: 99%

Synthesis and Characterization of a Novel Imidazolium Short‐Chain Fluorocarbon Surfactant as a Potential Agent for Aqueous Film Forming Foam

Wang,

Bai,

Zhu

et al. 2023

ChemistrySelect

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“…43 In subsequent studies, a series of sulfonate surfactants with degrading points were synthesized, which were believed to be safer than PFOS. 44 Inspired by their work, this article synthesized two sulfonate fluorosurfactants with ether bonds by introducing a hydrophilic group using 1,3propane sultone. Herein, the synthetic methods of 2 and 4, their surface activity, foamability, foam stability, and wettability as well as a comparison with 7 are reported.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Surface Activity, and Foamability of Two Short-Chain Fluorinated Sulfonate Surfactants with Ether Bonds

Guo,

Huang

et al. 2023

Langmuir

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Fluorinated surfactants are widely used in many fields because of their excellent surface active properties, but their high stability has caused many environmental problems. With the ban and restriction of classical long-chain fluorinated surfactants such as perfluorooctanesulfonic acid (PFOS) and perfluorooctanoic acid (PFOA) worldwide, the development and replacement of their alternatives is now a major challenge. How to reduce environmental persistence, bioaccumulation, and biotoxicity while maintaining high surface activity has become an important issue in the development of fluorinated surfactants. Using short-chain fluorinated surfactants is one of the important solutions to resolve the pollution of organic fluorinated compounds. In this article, we synthesized two short-chain fluorinated surfactants with ether bonds. One of them 6:2 FTESNa (2) used the perfluoroalkyl chain (n-C 6 F 13 -) and the other C72 FEESNa (4) used the fluoroether segment with six fluorinated carbons and two oxygens (CF 3 OCF(CF 3 )CF 2 OCF(CF 3 )). The surface activity, foam performance, and wettability of the two molecules were measured. The surface tensions at critical micelle concentration (γ cmc ) and the critical micelle concentration (cmc) of 2 and 4 were 17.6 mN/m (2.2 g/L) and 20.2 mN/m (4.6 g/L), respectively. Both of them were significantly superior to the surface activity of 6:2 FTSNa (7) which is one of the current alternatives for PFOS. Additionally, the foamability and foam stability of both 2 and 4 were better than that of 7. In the aspect of wettability on PTFE, that of 4 was greater than those of 2 and 7. In summary, this work provided a new choice for alternatives of PFOS and PFOA.

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“…Currently, due to the nature of high quantum yield and readily synthetic process, some pyrazoline derivatives have been synthesized and used in fluorescence probes, for orientation 4 , detecting cation [5][6][7][8] , hydrazine 9,10 , thiols [11][12][13] , and DNA 14 . Moreover, their biological roles have been studied in insecticidal function [15][16][17] , human monoamine oxidase activity inhibition 18,19 , anti-inflammation [20][21][22] , antimicrobial 23,24 , analgesia 25 . In addition, pyrazoline derivatives could inhibit the proliferation of cancer cells with satisfactory activity 26,27 .…”

Section: Introductionmentioning

confidence: 99%

Discovery of new fluorescent thiazole–pyrazoline derivatives as autophagy inducers by inhibiting mTOR activity in A549 human lung cancer cells

et al. 2020

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A series of fluorescent thiazole–pyrazoline derivatives was synthesized and their structures were characterized by 1H NMR, 13C NMR, and HRMS. Biological evaluation demonstrated that these compounds could effectively inhibit the growth of human non-small cell lung cancer (NSCLC) A549 cells in a dose- and time-dependent manner in vitro and inhibit tumor growth in vivo. The structure–activity relationship (SAR) of the compounds was analyzed. Further mechanism research revealed they could induce autophagy and cell cycle arrest while had no influence on cell necrosis. Compound 5e inhibited the activity of mTOR via FKBP12, which could be reversed by 3BDO, an mTOR activator and autophagy inhibitor. Compound 5e inhibited growth, promoted autophagy of A549 cells in vivo. Moreover, compound 5e showed good selectivity with no influence on normal vascular endothelial cell growth and the normal chick embryo chorioallantoic membrane (CAM) capillary formation. Therefore, our research provides potential lead compounds for the development of new anticancer drugs against human lung cancer.

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Design, synthesis and surfactant properties of perfluorobutyl-based fluorinated sodium alkanesulfonates

Cited by 17 publications

References 19 publications

Synthesis and Characterization of a Novel Imidazolium Short‐Chain Fluorocarbon Surfactant as a Potential Agent for Aqueous Film Forming Foam

Synthesis and Characterization of a Novel Imidazolium Short‐Chain Fluorocarbon Surfactant as a Potential Agent for Aqueous Film Forming Foam

Synthesis, Surface Activity, and Foamability of Two Short-Chain Fluorinated Sulfonate Surfactants with Ether Bonds

Discovery of new fluorescent thiazole–pyrazoline derivatives as autophagy inducers by inhibiting mTOR activity in A549 human lung cancer cells

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