Synthesis and structure–activity relationships of nonionic surfactants with short fluorocarbon chains

Wang, Ruiguo; Song, Lei; Guo, Yuan; Kou, Junjie; Song, Hongjian; Liu, Yuxiu; Zhang, Jingjing; Wang, Qingmin

doi:10.1016/j.molliq.2020.114486

Cited by 24 publications

(6 citation statements)

References 37 publications

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“…In order to make asymmetric glycerol ether derivatives, glycidyl ether is an important platform molecule that has rarely been studied. The literature methods often report drawbacks associated with the use of excess ECH, 14 phase transfer catalysts, 15 and microwave reactors (i.e., small scale), 16 and most glycerol ethers were obtained either using complex operations or with relatively low yields.…”

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confidence: 99%

Glycerol‐derived solvents containing two or three distinct functional groups enabled by trifluoroethyl glycidyl ether

et al. 2021

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Conversion of epichlorohydrin to glycidyl ethers creates versatile precursors that can be transformed into a variety of molecular species with glycerol skeletons, enabling the design of molecules with highly tailored functionalities. The synthesis of 2,2,2-trifluoroethyl glycidyl ether (TFGE, IUPAC name: 2-[(2,2,2-trifluoroethoxy) methyl]oxirane, CAS# 1535-91-7) was optimized to provide high yield/selectivity and good "green metrics." TFGE was then used as a platform molecule in the synthesis of asymmetric glycerol 1,3-diether-2-alcohol derivatives, which were subsequently transformed to 1,2,3-triethers or 1,3-diether-2-ketones. The density, viscosity, and CO 2 solubility of each molecule were measured and compared with those of other glycerol-derived compounds as well as compounds with similar functional groups. Furthermore, quantum chemical calculations were performed to understand the structure-property-performance relationships of these molecules for CO 2 absorption. Based on the results in this work, we foresee that TFGE (and similar glycidyl ethers) would offer great flexibility in molecular design of green solvents and precursors to more complex compounds.

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confidence: 99%

Glycerol‐derived solvents containing two or three distinct functional groups enabled by trifluoroethyl glycidyl ether

et al. 2021

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“…When the CMC of 2PP‐PPP was about 50 mg/L, the interfacial tension was decreased to 2.5 mN/m. Wang 40 et al synthesized nonionic fluorosurfactant 5i from methoxypolyethylene glycol (mPEG) or 2‐methoxyethanol, cyclic brominated alcohols, and perfluoroalkyl alcohols, which only can reduce the surface tension of water to 17.89 mN/m. Therefore, 2PP‐PPP has the superior interfacial activity.…”

Section: Resultsmentioning

confidence: 99%

“…When the CMC of 2PP-PPP was about 50 mg/L, the interfacial tension was decreased to 2.5 mN/m. Wang 40 concentration was below 1 wt%, microdroplets occurred over a large demulsification area, indicating that surfactant concentrations below 1 wt% were too low to cover the interface and generate a stable interfacial film. Clusters of negative and positive droplets were clearly separated for the concentration range 1-4 wt%, indicating that the generated microdroplets were stable.…”

Section: Effects Of Different Surfactant Concentrations On Their Perf...mentioning

confidence: 99%

Synthesis of a biocompatible fluorinated multiblock copolymer surfactant for water‐in‐fluorocarbon droplets and its application in droplet digital polymerase chain reaction

Feng,

Li,

Zhu

et al. 2024

J of Applied Polymer Sci

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Droplet digital polymerase chain reaction (ddPCR) technology has attracted considerable attention in recent years. A multiblock surfactant based on perfluompolyethers (PFPE) has been widely used in droplet‐based microfluidics and is known to provide high droplet stability and biocompatibility. We developed a multiblock copolymer surfactant synthesized by adjusting the proportions of the intermediates to enhance the stabilities of droplets at high temperatures. The surfactants were synthesized via amidation reactions that coupled the PFPE and diamine polyethylene glycol (PEG), and the introduction of triethylamine, as a catalyst, made the reaction more efficient. The as‐synthesized surfactants were used to generate water‐in‐ fluorocarbon (W/F) droplets with a microfluidic device and a ddPCR device was used to evaluate the performance of the droplets. When the molar ratio (PFPE‐PEG:PFPE‐PEG‐PFPE) was 2:1 and the concentration reached 2 wt%, the droplets showed good thermal stability. Surfactant showed the best performance, lowering the interfacial tension to 2.5 mN/m, when it's critical micelle concentration (CMC) exceeded 50 mg/L. Furthermore, the use of an alkaline solution (pH = 9–10) as the washing buffer, improved the biocompatible of the surfactant. When applied to the detection of λDNA, the limit of detection was 0.52 copies/μL. The as‐synthesized surfactants showed promise in generating biocompatible and thermally stable droplets and providing a new surfactant option for future ddPCR technology.

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“…The detergency of surfactants was studied using the RHLQ-III washing machine . The surfactants studied were POEA solutions with a concentration of 2 g/L and a hard water concentration of 250 mg/kg.…”

Section: Methodsmentioning

confidence: 99%

“…The detergency of surfactants was studied using the RHLQ-III washing machine. 29 The surfactants studied were POEA solutions with a concentration of 2 g/L and a hard water concentration of 250 mg/kg. Washability tests were carried out at an agitation speed of 120 rpm, a temperature of 30 ± 1 °C, and a washing time of 20 min.…”

Section: Langmuirmentioning

confidence: 99%

Effect of Different Ethylene Oxide Addition Numbers on the Performance of Polyoxyethylene Tallow Amine as a Pesticide Emulsifier

Lang,

Zhou,

Sun

et al. 2023

Langmuir

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Surfactant reduces the surface tension of liquids, resulting in improved emulsion stability, and there is great interest in pesticide additives. Ethoxylate is often used as a pesticide emulsifier. However, the degree of ethoxylation and the existence of dioxane byproducts can significantly affect the performance of emulsifiers. Here, a series of polyoxyethylene tallow amines with the addition of different numbers of ethylene oxide (EO) were synthesized and characterized. Their physical and chemical performances were measured. The ability of POEA as a surfactant to reduce water surface tension and the surface adsorption of molecules were assessed based on the static and dynamic surface tensions. The results show that the surfactant molecules preferentially form a saturated adsorption layer in solution, and the mixed-diffusion-kinetics mechanism dominates the adsorption process. With the increase of the EO addition number, the emulsifying property of POEA increases, while the wetting property gradually decreases and the contact angle increases. These results can provide a basis for the selection of pesticide additives. At the same time, the mechanism of removing dioxane by ethoxylate is described, and a simple and low-consumption method is put forward to reduce the dioxane content. It provides a new idea for the removal of dioxane.

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Synthesis and structure–activity relationships of nonionic surfactants with short fluorocarbon chains

Cited by 24 publications

References 37 publications

Glycerol‐derived solvents containing two or three distinct functional groups enabled by trifluoroethyl glycidyl ether

Glycerol‐derived solvents containing two or three distinct functional groups enabled by trifluoroethyl glycidyl ether

Synthesis of a biocompatible fluorinated multiblock copolymer surfactant for water‐in‐fluorocarbon droplets and its application in droplet digital polymerase chain reaction

Effect of Different Ethylene Oxide Addition Numbers on the Performance of Polyoxyethylene Tallow Amine as a Pesticide Emulsifier

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