Sulfonic Acid Salt Research Articles

Zwitterionic and vinyl-N-imidazolium ionic liquids

In this paper, we present employing our own and literature data the results of investigation of the thermal behavior and ion transport properties of vinyl and alkyl imidazolium zwitterions containing an alkane sulfonic acid group and salts on their basis. For comparison, we present the results of investigation the respective vinyl and alkyl imidazolium ILs without these functional groups. The phase behavior of zwitterionic and vinyl imidazolium ionic liquids is studied by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).

Biological responses in Danio rerio by the disinfectant SDBS in SARS-CoV-2 pandemic

The use of disinfectants, such as Sodium Dodecylbenzene Sulfonic acid salt (SDBS), has grown since the SARS-CoV-2 pandemic, with environmentally unknown consequences. The present study analyzed SDBS effects in the fish species Danio rerio, using a combination of biomarkers. Our data reported that larvae had their total locomotor activity increased when exposed to 1 mg/L of SDBS, but this parameter was decreased in fish exposed to 5 mg/L. A significant increment of erratic movements was reported in fish exposed to 1 and 5 mg/L of SDBS. These concentrations inhibited CYP1A1/CYP1A2, and of GSTs inhibition, suggesting SDBS is not preferentially biotransformed by these routes. Results concerning the antioxidant defense biomarkers (CAT and GPx) showed no straightforward pattern, suggesting SDBS exposure may have resulted in changes in redox balance. Finally, acetylcholinesterase activity increased. In summary, increased use of SDBS in a near future may result in deleterious effects in environmentally exposed fish.

Study on the effects of carbon nanotubes and xanthan gum on the performance of hydrocarbon surfactant foam systems

To improve the foam stability and fire extinguishing efficiency of fluorine-free foam (FFF) extinguishing agents, xanthan gum (XG) and carbon nanotubes (CNTs) were selected as the foam stabilizer agents in this study to investigate their effects on the physical and chemical properties and fire suppression effectiveness of FFF system. The effects of the four factors, namely, α-olefin sulfonic acid Salts (AOS), YT-Y762, XG, and CNTs, on the foam performance were investigated using L9(34) orthogonal design method. Three FFF solutions were selected based on the following four parameters: surface tension, 25% drainage time, foam height, and viscosity. The physicochemical properties, fire extinguishing, and burnback performance of the three FFF solutions were investigated. The results indicated that XG and CNTs have synergistic effects on the FFF solution, and the addition of 0.2 wt% of XG and 0.4 wt% of CNTs increased the 25 % drainage time by 81.40 %. The fire extinguishing performance was effectively improved. The results show the potential application of carbon nanotubes in FFF extinguishing agents.

Synthesis of silica bearing sulfobetaine and sulfonic groups and their electrorheological response

Organically modified silica bearing amino groups (SiO2-NH2) was prepared by the simple sol-gel procedure followed by treatment with butanesultone to produce zwitterionic silica bearing sulfobetaine groups (SiO2-SB). This particle was then treated with sulfuric acid to prepared particles carrying both sulfonic acid and ammonium salt (SiO2-SO3H). These particles were characterized by different methods and dispersed in silicone oil (15 wt%) to evaluate the electrorheological (ER) performance. Thermogravimetric (TG) analysis, zeta potential and Fourier transform infrared (FTIR) spectroscopy confirmed the structure of the modified silica. The ER response was evaluated using controlled shear stress (CSR) and oscillatory mode. The SiO2-NH2 and SiO2-SB based fluids displayed the highest shear stress at low shear rate even without an applied electric field. However the higher ER efficiency and lower leakage current was observed for the fluid containing SiO2-SO3H. From dielectric analysis, it was demonstrated that the zwitterionic SiO2-SB particle provided faster relaxation time and larger permittivity difference. Thus, it is possible to conclude that the lower viscosity of the SiO2-SO3H based fluid without electric field also plays an important role for a good ER efficiency. Both SiO2-SB and SiO2-SO3H particles are suitable for producing ER fluids due to their better dielectric properties and relaxation time. The former also presented better sedimentation stability.

Synthesis of Sulfonic Acid Salts and Sulfonic Acids by Advanced Cross‐Coupling Reaction of Vinyl Sulfonates

AbstractThe present work describes an advanced cross‐coupling reaction of vinyl sulfonates for the synthesis of sulfonic acid salts and sulfonic acids under mild reaction conditions. The regioselectivity of the double Negishi reaction was achieved by means of the different reactivity of the C−Br and activated C−O bonds. The cross‐coupling reaction leads to a mixture of alkenes and sulfonic acid salts. The separation of alkenes and sulfonic acid salts is achieved through the low solubility of sulfonic acid sodium salts after workup. In addition, the developed procedure is also used for the atom‐economical preparation of cyclooxygenase‐2 inhibitors (COX‐2).

PVA-Silica Composite Membrane for Aqueous Hybrid Flow Battery

The use of redox flow batteries (RFBs) has become a wise decision to preserve renewable energy. For its widespread commercialization, the appropriate selection of redox-active species and ion exchange membranes (IEM) is essential. Herein, we synthesized a robust PVA-Silica (PVA-SiO2) composite membrane and demonstrated its essential use in an aqueous hybrid RFB. A proton-conducting, chemically and physically stable membrane was created by combining the traditional hydrophilicity of PVA with well-defined interconnecting ion-conducting channels produced by uniformly distributed silica particles. We believe that thermal crosslinking ensured substantial dimensional and chemical durability, whereas silica permitted good ionic conductivity. The utility of the membrane was proved in a hybrid redox flow battery consisting of newly synthesized 1,4-phenoxy bis-propane sulfonic acid (PPS) and vanadium (III) salt in 2 M H2SO4. A detailed battery analysis was carried out with a rate performance study, cycling test, polarization curve, and OCV. Over 100 charge/discharge cycles, it demonstrated 95% coulombic efficiency, 61% voltage efficiency, and 57% energy efficiency at a current density of 50 mA cm−2, indicating the best utility of an oxidatively susceptible functional group-free robust proton conducting membrane.

Highly Efficient Nonfullerene Organic Solar Cells with Nickel Oxide Hole‐Transporting Layer: Using Dipole‐Induced Energy‐Level Modification

To date, poly(3,4‐ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS) is the most commonly used hole‐transporting material (HTM) for nonfullerene acceptor (NFA) organic solar cell (OSCs) due to its high hole conductivity and reproducibility. However, considering the significant breakthroughs made by novel donor and NFA combinations such as PM6 and Y6, the development of HTMs which can outperform PEDOT:PSS is very limited. Here, for the first time, high‐performance NFA OSCs based on simple and solution‐processed nickel oxide HTMs with high power conversion efficiency (PCE) and stability are reported. Two different kinds of hydroquinone sulfonic acid (HSA) salts, which have a permanent dipole moment, are added to NiO solution. Due to the interfacial dipole moment generated by these salts and effective work function modulation of NiO, efficient hole transportation at the interface between hole‐transporting layer and bulk heterojunction (BHJ) layer by minimizing the energetic barrier is promoted. As a result, using PM6 and the Y6‐BO‐4F‐based BHJ layer, the PCE of 14.19% with very high open‐circuit voltage of 0.86 V is achieved, which is comparable with that of PEDOT:PSS‐based OSCs. For 1200 h under ambient atmosphere, OSCs based on NiO containing HSA salts demonstrate enhanced ambient stability compared to that of PEDOT:PSS.

Ionic Push-Pull Polythiophenes: A Further Step towards Eco-Friendly BHJ Organic Solar Cells.

Four new conjugated polymers alternating benzothiadiazole units and thiophene moieties functionalized with ionic phosphonium or sulfonic acid salts in the side chains were synthesized by a postfunctionalization approach of polymeric precursors. The introduction of ionic groups makes the conjugated polymers soluble in water and/or polar solvents, allowing for the fabrication of bulk heterojunction (BHJ) solar cells using environmentally friendly conditions. All polymers were fully characterized by spectroscopic, thermal, electrochemical, X-ray diffraction, scanning electron, and atomic force techniques. BHJ solar cells were obtained from halogen-free solvents (i.e., ethanol and/or anisole) by blending the synthesized ionic push–pull polymers with a serinol-fullerene derivative or an ionic homopolymer acting as electron-acceptor (EA) or electron-donor (ED) counterparts, respectively. The device with the highest optical density and the smoothest surface of the active layer was the best-performing, showing a 4.76% photoconversion efficiency.

Biogenic aerosol in central East Antarctic Plateau as a proxy for the ocean-atmosphere interaction in the Southern Ocean

Ten years of data of biogenic aerosol (methane sulfonic acid, MSA, and non-sea salt sulfate, nssSO42−) collected at Concordia Station in the East Antarctic plateau (75° 06′ S, 123° 20′ E) are interpreted as a function of the Southern Annular Mode (SAM), Chlorophyll-a concentration (Chl-a; a proxy for phytoplankton biomass), sea ice extent and area. It is possible to draw three different scenarios that link these parameters in early, middle, and late summer. In early summer, the biogenic aerosol is significantly correlated to sea ice retreats through the phytoplankton biomass increases. Chl-a shows a significant correlation with nssSO42− in the finest fraction (< 1 μm). In contrast, only Chl-a in West Pacific and Indian Ocean sectors correlates with MSA in the coarse fraction. The transport routes towards the inner Antarctic plateau and aerosol formation processes could explain the different correlation patterns of the two compounds both resulting from the DMS oxidation. In mid-summer, Chl-a concentrations are at the maximum and are not related to sea ice melting. Due to the complexity of transport processes of air masses towards the Antarctic plateau, the MSA concentrations are low and not related to Chl-a concentration. In late summer, MSA and nssSO42− present the highest concentrations in their submicrometric aerosol fraction, and both are significantly correlated with Chl-a but not with the sea ice. In early and mid-summer, the enhanced efficiency of transport processes from all the surrounding oceanic sectors with air masses traveling at low elevation can explain the highest concentrations of nssSO42− and especially MSA. Finally, considering the entire time series, MSA shows significant year-to-year variability. This variability is significantly correlated with SAM but with a different time lag in early (0-month lag) and late summer (4-months lag). This correlation likely occurs through the effect of the SAM on phytoplankton blooms.

Influence of oligomethylenaryl sulphonates based on the light gas oil of catalytic cracking on the process of biocorrosion

This article presents the results of studies in the field of synthesis of water-soluble salts of oligomethylene aryl sulfonates synthesized using aromatic hydrocarbons contained in the gas oil fraction of the catalytic cracking process of oil as raw materials. Based on the synthesized various salts of oligoaromatic sulfonic acids (sodium, potassium, ammonium salts), solutions of various concentrations (35; 75; 150; 200 mg/l) were prepared and their effect on the vital activity of sulfate-reducing bacteria at a temperature of 30…32 °С for 7…14 days was studied. It was found that complex salts synthesized on the basis of oligomeric sulfonic acids of aromatic hydrocarbons of the gas oil fraction (N-1, N-2, N-3) at a concentration of 150 mg/l exhibit more than 90%, and at a concentration of 200 mg/l, 100% bactericidal effect and completely inhibits the growth of bacteria. It was revealed that the synthesized salts of sulfonic acids exhibit a relatively higher antimicrobial activity against SRB than the industrial bactericidal inhibitors AMDOR-IK-7 and AMDOR-IK-10 taken as a reference. Based on the studies, it was found that the synthesized salts of oligosulfonic acids completely inhibit the growth of sulfate-reducing bacteria at much lower concentrations compared to the industrially used bactericidal inhibitors taken as a reference. In particular, at a concentration of 150 mg/l, the bactericidal effect is more than 90% against 75…80% for the standard.

Identification of Water-Soluble Sulfonic Acids Isolated from Acid Tars by Gas Chromatography–Mass Spectrometry

We determined the nature of water-soluble sulfonic acids in acid tars taken from two storage ponds: one located at the 21 km of the M-7 Moscow–Nizhny Novgorod federal highway and another in the Kozinskoe forestry of the Balakhninsky district of Nizhny Novgorod oblast. Water-soluble compounds were extracted from acid tar with water; sulfuric acid was precipitated from acidic water as barium sulfate; the precipitate of barium sulfate was separated by filtration; the filtrate was neutralized with sodium carbonate and evaporated to dryness. The dry residue was treated with phosphorus pentachloride to convert sulfonic acid salts to volatile chlorides, which were analyzed by gas chromatography–mass spectrometry.

Dispersion of electrically conductive carbon fibres in self-compacting concrete using chemical and mechanical dispersing techniques

In this study, the influence of the mechanical de-agglomeration of carbon fibres in the mixing water blended with methylcellulose and sodium dodecyl benzene sulfonic acid salt (SDBS) for dispersion of carbon fibres in self-compacting concrete (SCC) was studied. The mechanical energy needed for de-agglomeration was provided by churning the carbon fibres in the treated water using mechanical churner at varying speed of 1440RPM to 23000RPM. The degree of dispersion was evaluated by investigating the variations in rheological, electro-mechanical and microstructure properties of carbon-fibre reinforced SCC. It was observed that the mechanical churner at lower speed (1440RPM to 11000RPM) in the surfactant blended water successfully deagglomerated the carbon fibre filament threads without disturbing their individual morphology that resulted in better distribution of fibres in the concrete. Microstructure images further confirmed the role of mechanical mixing in improving the dispersion of fibres.

Dispersion of electrically conductive carbon fibres in self-compacting concrete using chemical and mechanical dispersing techniques

In this study, the influence of the mechanical de-agglomeration of carbon fibres in the mixing water blended with methylcellulose and sodium dodecyl benzene sulfonic acid salt (SDBS) for dispersion of carbon fibres in self-compacting concrete (SCC) was studied. The mechanical energy needed for de-agglomeration was provided by churning the carbon fibres in the treated water using mechanical churner at varying speed of 1440RPM to 23000RPM. The degree of dispersion was evaluated by investigating the variations in rheological, electro-mechanical and microstructure properties of carbon-fibre reinforced SCC. It was observed that the mechanical churner at lower speed (1440RPM to 11000RPM) in the surfactant blended water successfully deagglomerated the carbon fibre filament threads without disturbing their individual morphology that resulted in better distribution of fibres in the concrete. Microstructure images further confirmed the role of mechanical mixing in improving the dispersion of fibres.

Elusive Impurities—Evidence versus Hypothesis. Technical and Regulatory Update on Alkyl Sulfonates in Sulfonic Acid Salts

There is a widespread and long-standing perception that drug substances presented as sulfonic acid salts pose an inherent risk to patients, owing to the potential presence of mutagenic alkyl sulfon...

Preparation and evaluation of the mixtures of sulfonate and phenate as lube oil additives

Lubricating oil additives impart new properties to oil or reinforce desirable properties already possessed by the oil. They are used to prevent sludge and varnish deposits in engines, to inhibit rust and corrosion, and to minimize wear and friction. Detergents, especially basic detergents, contain reserve base that will neutralize the acids, while this decreases the corrosive tendency of the acids formed at high temperatures. Dispersants also disperse sludge formed in engine operated at low temperature. In the present work, neutral, basic, and overbasic calcium salt of sulfurized dodecyl phenol and neutral calcium sulfonate were prepared and evaluated as antioxidant and detergent/dispersants. Also, different metallic mixtures were prepared via mixing dodecyl benzene sulfonic acid and neutral calcium salt of dodecyl phenol in different ratios. Then basic and overbasic of corresponding mixtures were prepared using excess of calcium hydroxide and carbon dioxide. The efficiency of the prepared compounds as detergent/dispersant additives for lubricating oil was investigated. It was found that the prepared additives have excellent power of dispersion and detergency and this efficiency increases by increasing basicity, percentage of calcium salt, and the ratio of dodecyl benzene sulfonic acid in the mixture.

Thermal stability of end‐capped and linear sulfonated polyimides, sulfonated polystyrene, and Nafion 117

ABSTRACTThe thermal stability of end‐caped and linear sulfonated polyimides (SPIs), sulfonated polystyrene (SPS), and a sulfonated perfluorinated hydrocarbon, Nafion 117, and the corresponding triethylammonium sulfonate salts was investigated by dynamic and isothermal thermogravimetric analysis (TGA). Gas chromatographic‐mass spectrographic analysis (GC/MS) of the sulfonated polymers and the salts to determine the volatiles released from acid and salt groups over a temperature range 200–275 °C was also investigated. GC/MS analysis reveals that water and sulfur dioxide volatiles are released from the sulfonic acids and water, sulfur dioxide and triethyl amine are released from the sulfonate salts. Dynamic and isothermal TGA studies based on weight loss revealed that the SPIs exhibited superior thermal stability than SPS and Nafion 117 sulfonic acids. However, dynamic TGA curves to determine the onset decomposition temperature of the sulfonic acid group reveal that Nafion 117 and SPS sulfonic acids exhibited greater thermal stabilities than the SPIs. The mechanisms of sulfonic acid and triethylammonium sulfonate salt decompositions based on GC/MS, 13C‐NMR, and dynamic TGA curves are proposed. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45694.

ソックスレー抽出器を用いたアミノ酸エチルエステル-p-トルエンスルホン酸塩の合成

ソックスレー抽出器を用いたアミノ酸エチルエステル-p-トルエンスルホン酸塩の合成

Synthesis and Properties of 2-Oxa-6-azaspiro[3.3]heptane Sulfonate Salts

An improved synthesis of the bicyclic spiro compound 2-oxa-6-azaspiro[3.3]heptane is presented. While this compound is often isolated as an oxalate salt, its isolation as a sulfonic acid salt yields a more stable and more soluble product. With these improved properties access to a wider range of reaction conditions with the spirobicyclic 2-oxa-6-azaspiro[3.3]heptane has been enabled.

Sulfonate-functionalized nanoporous silica spheres as adsorbent for methylene blue

Sulfonate-functionalized nanoporous silica spheres (NSS-SO3) were prepared by conversion of epoxide to sulfonate with sulfonic acid salts. NSS-SO3 was used as an adsorbent for removal of methylene blue (MB) cationic dye. The adsorbent was characterized by means of scanning electron microscopy (SEM), N2 adsorption–desorption isotherms, Fourier-transform infrared (FTIR) and Raman spectroscopy, and thermogravimetric analysis. SEM images showed the spherical morphology of the material. The synthesized material was successfully applied for MB removal from synthetic solution in batch systems. The equilibrium sorption isotherm and kinetics were investigated. The adsorption of dye onto the adsorbent could reach equilibrium after 60 min. The equilibrium adsorption data were best described by the Langmuir isotherm. A maximum monolayer sorption capacity of 208 mg g−1 was found. The kinetic studies indicated that the adsorption process could be well fited by a pseudo-second-order kinetic model.

Sulfonic Acid Salts of Donepezil and Stabilization of Amorphous Donepezil via Formation of Amorphous Salts

Three crystal structures of donepezil salts formed with sulfonic acids were obtained. Interestingly, donepezil-besylate and donepezil-tosylate share similar crystal molecular conformations and crystal packing. On the basis of PXRD patterns, donepezil-mesylate and donepezil-esylate are likely to share similar crystal structures. The sulfonyl hydroxides of all three sulfonic acids form an intermolecular hydrogen bond with the piperidyl amine of donepezil. Solid state characterization showed that the Tg’s of all four amorphous donepezil salts are similar to each other and increase significantly compared to Tg of donepezil. Stability analysis found that the amorphous salts of donepezil formed with mesylate and esylate led to significantly improved physical stability under accelerated stability conditions, but the other donepezil-sulfonic acid salts did not. Solubility data showed that mesylate/esylate salts of donepezil significantly increase the solubility of donepezil that is not shown by other salt forms. Solubility analysis indicated that the solubility of donepezil-mesylate and donepezil-esylate is extremely high compared to that of donepezil-besylate and donepezil-tosylate. We concluded that the extremely high solubility is responsible for delaying the rate of nucleation and thus improving the physical stability of amorphous donepezil. This study highlights that the aqueous solubility of amorphous material is an important factor when considering the physical stability of amorphous material under high relative humidity.