- Surface and Antimicrobial Activity of Sulfobetaines
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Sulfobetaines belong to the group of zwitterionic surfactants. They are electroneutral salts, which have in the same molecule, two ionic centers with different charge. Due to the specific structure they exhibit excellent properties such as good solubility in water and detergency. In this paper we present surface properties and adsorption parameters of sulfobetaines in water/air systems. From the adsorption isotherms the CMC value, the surface tension and surface pressure at the CMC as well as the efficiency of adsorption were determined. Physicochemical analyses of the data allowed for the further description of adsorption process. Results showed that sulfobetaines exhibit good surface properties especially low CMC and p20 values. Additionally the antimicrobial activity of sulfobetaines solutions against gram-positive and gram-negative bacteria were tested by the well-diffusion method. MIC values and growth kinetics were determined by microdilution method. Antimicrobial assays demonstrated that sulfobetaines can be good antibacterial agents, but the activity of surfactants strongly depends on alkyl chain length.
- Wieczorek, Daria,Gwiazdowska, Daniela,Staszak, Katarzyna,Chen, Ying-Lien,Shen, Tang-Long
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- Eco-friendly synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by ionic liquid in aqueous media
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A biodegradable functionalized ionic liquid 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulfate ([DDPA][HSO4]) was prepared and used as a Bronsted acid-surfactant-combined catalyst for the eco-friendly one-pot synthesis of 1,8-dioxo-octahydroxanthenes at 100°C in water. Under these conditions, the reaction of various aromatic aldehydes with dimedone generated 1,8-dioxo-octahydroxanthenes in good yields with a simple postreaction procedure. The products could simply be separated from the catalyst/water system, and the catalyst could be reused at least six times without noticeably decreasing the catalytic activity.
- Fang, Dong,Yang, Jin-Ming,Liu, Zu-Liang
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- Selective oxidation of alcohols with H2O2 catalyzed by long chain multi-SO3H functionalized heteropolyanion-based ionic liquids under solvent-free conditions
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Two novel long chain multi-SO3H functionalized heteropolyanion-based ionic liquids were prepared and characterized. They as homogeneous catalysts showed high catalytic activity in selective oxidation of alcohols with 35% aqueous hydrogen peroxide under solvent-free conditions without adding any phase transfer catalyst. Two ionic liquids can be recovered readily and reused five times without any significant loss in their catalytic activities.
- Li, Xinzhong,Cao, Rong,Lin, Qi
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- Room temperature deep eutectic solvents of (1S)-(+)-10-camphorsulfonic acid and sulfobetaines: Hydrogen bond-based mixtures with low ionicity and structure-dependent toxicity
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Twelve novel deep eutectic solvents (DESs) were prepared and characterized in this work. They are mixtures of (1S)-(+)-10-camphorsulfonic acid (CSA) and differently structured sulfobetaines (SBs) with aliphatic, aromatic and amphiphilic moieties. They are liquids at room temperature, their melting points span, in fact, from -5° to 19 °C, so we can name these mixtures RTDESs (room temperature deep eutectic solvents). These zwitterionic DESs were characterized in terms of their viscosity, conductivity (and therefore ionicity via Walden plots), density, surface tension and toxicity on eukaryotic model cells. The collected data suggest that the interaction between CSA and the SBs can be ascribed as a hydrogen bond instead of a proton transfer, therefore they are not ionic liquids. To our knowledge, their position on the Walden plot, in the left portion close to the diagonal, has not yet been observed for other DESs or ionic liquid systems and indicates the low ionicity of these mixtures. A FTIR-based bioassay was performed to determine the toxicity of these mixtures on eukaryotic model cells (Saccharomyces cerevisiae). The DESs showed merely a dehydrating effect on the cells, similar to that produced by CaCl2, a low cell toxicity salt. This supports these DESs as promising green media. Amphiphilic SBs DESs showed a stronger effect on the cells and a structure-activity trend can be described for this class. A preliminary study on the use of these novel DESs as Bronsted catalyst media was accomplished by the use of one of them in chalcone synthesis, which showed promising catalytic and recycling capabilities.
- Cardellini, Fabio,Germani, Raimondo,Cardinali, Gianluigi,Corte, Laura,Roscini, Luca,Spreti, Nicoletta,Tiecco, Matteo
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p. 31772 - 31786
(2015/04/22)
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- Biodiesel synthesis from the esterification of free fatty acids and alcohol catalyzed by long-chain Bronsted acid ionic liquid
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A long-chain Bronsted acid ionic liquid (IL), 3-(N,N- dimethyldodecylammonium)propanesulfonic acid p-toluenesulfonate ([DDPA][Tos]), was prepared and characterized by FT-IR, 1H NMR, 13C NMR, UV/vis and TGA. The H0 (Hammett function) value of the IL was also determined. The IL as catalyst was applied to the catalytic synthesis of biodiesel from free fatty acids (FFAs). The influencing factors, such as the type and amount of catalyst, reaction time, molar ratio of fatty acid to methanol and reaction temperature, were investigated. The results indicated that the long-chain Bronsted acid IL showed high catalytic activity and fair reusability. Esterification was accomplished under the following optimized conditions: molar ratio of alcohols to FFA at 1.5:1, mole fraction of ionic liquid at 10%, 60 °C, and 3 h. The products could be separated from the catalyst system by liquid-liquid biphase separation at room temperature with good yields of 92.5% to 96.5%. The catalyst could be reused nine times after the removal of water and alcohol. Therefore, the long-chain Bronsted acid IL has good potential for the synthesis of biodiesel from low-cost feedstocks such as waste oil and woody plant oils.
- He, Leqin,Qin, Shenjun,Chang, Tao,Sun, Yuzhuang,Gao, Xiaorui
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p. 1102 - 1107
(2013/04/24)
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- AMINO- OR AMMONIUM-CONTAINING SULFONIC ACID, PHOSPHONIC ACID AND CARBOXYLIC ACID DERIVATIVES AND THEIR MEDICAL USE
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The present invention relates to amino- or ammonium-containing sulfonic acid, phosphonic acid and carboxylic acid derivatives, in particular the compounds of formula 1, 2, 3, 4, 5 or 6, and their medical use, including their use in the treatment, prevention or amelioration of an inflammatory, autoimmune and/or allergic disorder.
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Page/Page column 40
(2012/12/13)
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- Synthesis, characterization and surface properties of series sulfobetaine surfactants
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A series of surface active sulfo-propane betaines and sulfo-butane betaines were synthesized with high yields by the reaction of an appropriate N,N-dimethyl alkylamine with an excess of 1,3-propane sultone and 1,4-butane sultone. The structures were characterized by 1H-NMR spectroscopy and elemental analysis. The micellar properties of these compounds were determined by surface tension methods. Surface tension measurements also provide information about the dependence of the surface tension at the CMC (γcmc), pC20 (negative logarithm of the surfactant molar concentration C20 required to reduce the surface tension by 20 mN/m), the surface excess (Γmax) at air/solution interface, the minimum area per surfactant molecule at the air solution interface (A).
- Qu, Guangmiao,Cheng, Jiecheng,Wei, Jijun,Yu, Tao,Ding, Wei,Luan, Huoxin
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experimental part
p. 31 - 35
(2012/01/13)
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- One-pot, three-component Mannich-type reaction catalyzed by functionalized ionic liquid
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A three-component Mannich-type reaction of aromatic aldehydes, aromatic amines, and ketones was catalyzed by a novel functionalized ionic liquid, 3-(N,N-dimethyldodecylammonium)propanesulfonic acid hydrogen sulfate ([DDPA][HSO4]) at room temperature to give various β-amino carbonyl compounds in good yields. The catalyst could be reused at least six times without noticeably reducing catalytic activity.
- Fang, Dong,Gong, Kai,Zhang, Dai-Zhen,Liu, Zu-Liang
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experimental part
p. 1325 - 1329
(2010/05/19)
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- Synthesis of quaternary alkylammonium sulfobetaines
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A series of quaternary alkylammonium sulfobetaines of general formula RN+(CH3)2(CH2)nSO 3-, where n = 2-4, have been synthesised by reacting the corresponding N,N-dimethylamines with either sodium 2-chloroethanesulfonate (n = 2), 1,3-propane-sultone (n = 3), or 1,4-butanesultone (n = 4). Full details of the preparation of the required N,N-dimethylamines are reported.
- Ward, Robert S.,Davies, Joanna,Hodges, Geoffrey,Roberts, David W.
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p. 2431 - 2439
(2007/10/03)
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- A Proton NMR Study on the Structure of Water of Hydration of Aqueous Micelles
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The chemical shift of water was measured as a function of concentration of the detergents cetyltrimethylammonium chloride, CTACl; 3-N-dodecyl-N,N-dimethylammonio-1-propanesulfonate, DDAPS; polyoxyethylene (9.5) octylphenyl ether, Triton X-100, and the deuterium content of the solvent.The short chain compound butyltrimethylammonium bromide was also studied as a model for CTACl.Graphs of the chemical shifts vs. the mole fractions of the solubilizates were linear in all cases and the slopes were used to calculate the so called "fractionation factor, φ" which can be used as a measure of the degree of structure of the water of hydration of the appropriate species (relative to bulk water).The calculated φ values indicated that the butyltrimethylammonium ion does not perturb hydrogen bonding of the solvent (φ = 0.99), whereas the water in the Stern layer of CTACl is more organized than bulk water (φ = 1.06).Zwitterionic DDAPS was found to enhance the structuring marginally (φ = 1.02) whereas the nonionic surfactant Triton X-100 has a structure decreasing effect (φ = 0.95). - Keywords: Colloides / H/D Fractionation / Isotope Effects / Micelles / Spectroscopy, Nuclear Magnetic Resonance
- El Seoud, Monica I.,Farah, Joao P. S.,El Seoud, Omar A.
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p. 180 - 183
(2007/10/02)
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- The Upper Consolute Boundary in Zwitterionic Surfactant-Water Systems
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Selected zwitterionic surfactants display a liquid-liquid miscibility gap having an upper critical temperature, which differs in overall shape from the "cloud point" miscibility gap displayed by single-bond and semipolar surfactants.The dependence of the location of this phase phenomenon on the molecular structure of the surfactant and NMR investigations of the isotropic solution structure in the vicinity of the gap are reported.Lengthening the lipophilic group enlarges the area spanned by both the cloud point miscibility gap and the zwitterionic surfactant-water miscibility gap.However, increasing the size of proximate substituents further enlarges the former but shrinks the latter.This gap is most evident in ammonio sulfates, less so in ammonio sulfonates, and does not exist in ammonio carboxylate-water systems.NMR investigations of the structure of 3-(nonyldimethylammonio)propyl sulfate-water solutions in the region of its miscibility gap have been carried out using the pulsed field gradient spin-echo method.In addition, 1H NMR spectra have been recorded.The self-diffusion data, just below the independently measured critical micelle concentration (cmc), show that the surfactant exists as a molecular solution.In contrast to ionic surfactants, the concentration of molecular surfactant increases slowly above the cmc.Above the cmc, the self-diffusion data suggest that small, spherical micelles exist over a wide range of concentrations and temperatures.The NMR line widths observed in the continuous-wave mode are consistent with this interpretation.Estimates of the hydration levels of the surfactant suggest that hydration decreases with increasing concentration and temperature but remains relatively high even at 80 deg C.These studies reveal no anomalies in solution structure or aggregation phenomena in the vicinity of the miscibility gap.
- Nilsson, Per-Gunnar,Lindman, Bjoern,Laughlin, Robert G.
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p. 6357 - 6362
(2007/10/02)
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