Sulfonate Esters Research Articles

APPLICATION OF Eco-Enzyme CONVERSION RESULTS INTO DISHWASHER SOAP

The application of the conversion results from Eco-Enzyme into dishwashing soap, the fermentation process lasts for one months, where the resulting liquid is dark brown in color and has a very strong sweet and sour fermented aroma. There is a lack of public knowledge about the very profitable benefits of Eco-Enzyme, such as as a multi-purpose cleaner as a multi-functional liquid which can be converted, one of the ways, into dishwashing soap. This research aims to determine the application of the results of converting Eco-Enzyme into dishwashing soap. This research used experimental methods and a research period of 3 months. This Eco-Enzyme is made with a ratio of organic ingredients: sugar: water 3:1:10. The Eco-Enzyme harvest is converted into dishwashing soap by adding lerak and Methyl Ester Sulfonate (MES). Eco-Enzyme conversion soap was then applied to several treatment groups: plastic plates, cans and glass. The results of the application show that the dishes washed with Eco-Enzyme using lerak have not completely removed dirt, oil and odors in each treatment, whereas Eco-Enzyme using Methyl Ester Sulfonate (MES) when compared with Sunlight brand liquid soap sold on the market shows that there are similarities both in terms of cleanliness, tapestry and smell. The research conclusion is that the application of the Eco-Enzyme conversion results has significant potential to be developed into an active ingredient for environmentally friendly dishwashing soap.

Electrochemical Sulfonylation of Indoles with Inorganic Sulfites and Alcohols: Direct Synthesis of Indole Sulfonic Esters.

A direct electrochemical sulfonylation between indoles, inorganic sulfites, and alcohols was developed, in which various indoyl sulfonate esters were prepared efficiently. In this transformation, the easy-handle and cost-effective inorganic sulfite was disclosed to engage in a Csp2-H sulfonylation as the SO2 source in an undivided electrolysis cell under mild conditions. In addition, the unexpected paired electrosynthesis has been achieved, owing to the dual role of inorganic sulfites, and led to a sulfonylation/reduction sequence to rapidly deliver hydroxyl substituted indole sulfonate esters.

Pembuatan Sabun Cuci Piring Cair Ramah Lingkungan BeEkstrak Kulit Jeruk Nipis (Citrus Aurantiifolia)

ish washing soap is a cleaner made by a chemical reaction between potassium or sodium and fatty acids from vegetable oils or animalfats. Making liquid dishwashing soap from lime peel extract has been carried out using the extraction method. This research aims todetermine the effect of lime peel extract and Methyl Ester Sulfonate (MES) on the characteristics of the liquid dishwashing soap produced,including several tests, namely pH, density, viscosity, bacteria based on SNI 06-2075-1996. Soap making is done by varying the volume oflime peel extract 3, 6, 9, 12, 15 ml and the MES mass 5, 10, 15, 20, 25, 30 grams, as well as adding other ingredients such as NaCl 8 grams,distilled water 300ml, aromatics 2 ml, dye 1 gram. The research results showed that a lime peel extract volume of 6 ml and a MES massof 15 grams produced the best soap with a pH of 6.04, density of 1.099 gr/ml, viscosity of 19.8 cP, bacteria 4 colonies/gr.

Solvent‐Free Synthesis of Carvone Oxime Ester and Carvone Oxime Sulfonic Esters

AbstractA ZnO‐mediated benzoylation between carvone oxime and acyl is reported, enabling access to diverse carvone oxime ester and carvone oxime sulfonic esters under solvent‐free conditions. The operationally simple procedure provides a novel method for the synthesis of oxime‐ester bonds with excellent chemo selectivity. This strategy provides a mild, direct, and green approach for synthesizing carvone oxime ester in moderate to excellent yields with good substrate tolerance. In addition, carvone oxime was synthesized under solvent‐free conditions.

Sulfonamides and sulfonate esters: Synthetic routes, proposed mechanisms, and crystallographic characterizations

The sulfonamide and sulfonate moieties are key structural features in many pharmaceuticals, agrochemicals, and materials and have proven useful as synthetic precursors. In this review, synthetic routes for sulfonamides and sulfonate esters were examined to gain insight into the mechanism behind the sulfonylation of amines and alcohols, which remains largely unknown and highly dependent on the reaction conditions used. Furthermore, the review delves into crystallographic characterizations of previously reported sulfonamide and sulfonate ester compounds, unraveling trends associated with crucial steric and electronic factors that influence their crystallization. This exploration not only enhances our understanding of the structural nuances of these compounds, but also paves the way for informed design strategies in synthetic and medicinal chemistry. In essence, this review endeavors to provide a holistic perspective on sulfonamides and sulfonate esters, bridging the realms of synthesis, mechanism elucidation, and structural characterization.

A new coumarin-based “OFF–ON” fluorescent sensor for H2S detection in HeLa cells

A new “OFF–ON” coumarin-based fluorescent probe for H2S detection was designed and successfully developed through O-sulfonylation between a dabsyl quencher and 7-hydroxy-4-methylcoumarin as a fluorescent reporter, based on a FRET approach. This H2S responsive probe, utilizing H2S assisted thiolysis of a sulfonate ester as the sensing strategy, demonstrated excellent performance towards H2S with a limit of detection (LoD) of 1.64 µM, along with superb selectivity, good stability and high specificity towards H2S without interference from other biomarkers and analytes. Moreover, dabsyl-7-hydroxy-4-methylcoumarin (dabsylcoumarin) is capable of permeating the cell membrane and effectively visualizing the level of H2S in the living HeLa cells without cytotoxicity.

Diamine-surfactant adsorption at the air–water interface: The impact of the diamine structure, surfactant structure and solution pH

The biogenic amines, polyamines, such as putrescine and cadavarine, are small flexible polycations. They interact with charged biological species and have a range of important biological functions. Their strong interaction with anionic surfactants results in enhanced adsorption at interfaces. Aspects of the impact of the polyamine molecular weight and structure on the pattern of surfactant adsorption at the air–water interface have been explored previously using neutron reflectivity, NR, and surface tension, ST. However there is limited evidence for the extent to which surfactant adsorption can be manipulated and the impact of the diamine structure and surfactant headgroup structure on surfactant adsorption at the air–water interface is reported here.The addition of putrescine [1,4 diaminobutane or butanediamine] over the pH range 3 to 10 enhances significantly the adsorption of sodium dodecyl sulfate, SDS, sodium dodecyl diethylene sulfate, SLES, and sodium tetradecyl methyl ester sulfonate, MES. For SDS and to a lesser extent MES there are regions where surface multilayer adsorption occurs at both pH 3 and 10, and this extends significantly the range of polyamine structures for which this is observed. Modifying the diamine spacer with ethylene oxide groups of varying length still results in enhanced adsorption for SDS and MES, but the enhancement is less pronounced and depends upon the size of the ethylene oxide group. However the incorporation of the ethylene oxide group does suppresses the formation of the more complex surface multilayered structures.

Integrated design of flame retardancy, smoke suppression and structure of carbon fiber reinforced vinyl ester resin composites through intercalation of nanofiber membranes

A novel flame-retardant method based on the intercalation of nanofiber flame-retardant membrane has been studied for composite laminates. Compared to traditional additive flame-retardant method, this method is more efficient, does not affect the composite forming process, and can improve the mechanical properties of composite. Nanofiber flame-retardant membranes (FPm) are prepared from polyether sulfone (PES) and pentaerythritol phosphate ester (PEPA) by electrospinning technique and inserted in the interlayer of carbon fiber reinforced vinyl ester resin (CF/VER) composites. The FPm can improve the flame-retardancy and smoke suppression of the CF/VER composites by promoting the charring of interlayer structure and form a barrier layer. The thickness of the FPm and the flame-retardant performance of the composites are positive correlation. At a FPm’s thickness of 50 μm, the limiting oxygen index (LOI) and UL-94 ratings of the CF/VER composites reached 33.5 % and V-1, respectively. The total heat release (THR) and total smoke release (TSP) are reduced by 26.4 % and 30.4 %, respectively. Due to the interlayer enhancement effect of FPm, the mechanical strength and interlaminar fracture toughness of CF/VER composites are also improved. Especially, when the thickness of FPm is 30 μm, the mode I interlaminar fracture toughness (GIC) of the CF/VER composite increased by 17.4 %. while the flexural strength, interlayer shear strength (ILSS), mode II interlaminar fracture toughness (GIIC) and storage modulus (E’) are all enhanced.

MES surfactant-based liquid soaps added with eco-enzyme and pandan wangi leaf extract (Pandanus amaryllifolius Roxb) on physical-chemistry properties, and antibacterial activity,"

The growing demand for liquid soap has spurred innovations in soap formulations, particularly using methyl ester sulfonate (MES) as a surfactant base combined with natural ingredients like eco-enzyme and fragrant pandan leaf extract. This study aimed to determine the optimal liquid soap formulation by evaluating physicochemical properties and antibacterial activity against Staphylococcus aureus. The research was conducted in two stages. First, liquid soap was produced at different temperatures (20°C, 50°C, and 100°C) to identify the optimal temperature based on maximum lipase activity. In the second stage, various formulations were prepared, incorporating eco-enzyme and fragrant pandan leaf extract at the identified optimal temperature. The six formulations tested were: F1 (MES-based soap), F2 (20% eco-enzyme), F3 (15% eco-enzyme and 5% fragrant pandan leaf extract), F4 (10% eco-enzyme and 10% fragrant pandan leaf extract), F5 (5% eco-enzyme and 15% fragrant pandan leaf extract), and F6 (20% fragrant pandan leaf extract). The formulations were assessed for lipase activity, pH, density, and viscosity. The most effective formulation was further tested for antibacterial activity using the disc diffusion method with six treatments, including MES-based soap and controls. Statistical analysis using One-Way ANOVA revealed that adding eco-enzyme and fragrant pandan leaf extract significantly affected the soap's properties. The optimal formulation, containing 5% eco-enzyme and 15% fragrant pandan leaf extract, exhibited a lipase activity of 15,778 U/mL, a pH of 5.02, a density of 1.06 g/mL, a viscosity of 3.59 cP, and an antibacterial zone of 37.22 mm, making it the best candidate for further development

Room-Temperature Photochemical Copper-Mediated Fluorination of Aryl Iodides.

This report describes a method for the photochemical Cu-mediated fluorination of aryl iodides with AgF via putative aryl radical (Ar•) intermediates. It involves irradiating an aryl iodide with UVB light (λmax = 313 nm) in the presence of a mixture of CuI and CuII salts and AgF. Under these conditions, fluorination proceeds at room temperature for substrates containing diverse substituents, including alkoxy and alkyl groups, ketones, esters, sulfonate esters, sulfonamides, and protected amines. This method has been translated to radiofluorination using a combination of K18F, K3PO4, and AgOTf.

Quinoline sulfonates as the potent inhibitors of MDA-MB-231 and MCF-7 breast cancer cells: Synthesis, cytotoxicity, and molecular docking studies

Quinoline is a promising class of heterocycles with interesting biological and pharmacological properties including anti-cancer. Variety of quinoline-based derivatives have been synthesized previously and reported for diversed biological properties, which assisted in the development of new drug candidates. The current study describes the synthesis of quinoline-based sulfonic esters 1–42, and their cytotoxicity towards two breast cancer cell lines (MDA-MB-231, and MCF-7) and a normal human BJ cell line. Compounds 15, 20, and 28 showed the highest cytotoxicity against both breast cancer cell lines. Molecular docking studies predicted the hydrophobic interactions of test compounds with both estrogen α-receptor, and EGF-receptor.

Sulfonate-bridged semi-biopolyamide for Pb(II) electrochemical probing and dye adsorption

With the continuous development of modern industry, environmental problems accompanied by heavy metal Pb(II) and organic dyes become increasingly apparent, and the development of associated detection/removal materials has important practical significance thus. In this work, a novel biomass (diphenolic acid and furfurylamine)-based, polyamide-sulfonate cross-linked polymer (PA-df-OBSC) was successfully constructed. Further characterization of PA-df-OBSC indicated that the chemical structure of PA-df-OBSC consists of multiple N/O/S-containing molecular fragments as amide, tertiary amine, carboxylic acid, sulfonate ester and sulfonate acid. Such structural characteristic endows PA-df-OBSC dual functional application prospect. PA-df-OBSC can be applied as an enrichment-type Pb(II) electrochemical probe due to its specific complexation for Pb(II). The modified glassy carbon electrode (GCE) with PA-df-OBSC as active modifier presented a wide detection range (0.1–30 μmol/L) and low detection limit (1.31 × 10−8 M) for Pb(II). Besides, PA-df-OBSC also showed selective adsorption for cationic dye methylene blue (MB), with the maximum adsorption capacity up to 521.72 mg/g.

Application of Sodium Methyl Ester Sulfonate Anionic Surfactants as Corrosion Inhibitors for Carbon Steel in Oilfield Injection Water

Application of Sodium Methyl Ester Sulfonate Anionic Surfactants as Corrosion Inhibitors for Carbon Steel in Oilfield Injection Water

C(sp3)–H sulfinylation of light hydrocarbons with sulfur dioxide via hydrogen atom transfer photocatalysis in flow

Sulfur-containing scaffolds originating from small alkyl fragments play a crucial role in various pharmaceuticals, agrochemicals, and materials. Nonetheless, their synthesis using conventional methods presents significant challenges. In this study, we introduce a practical and efficient approach that harnesses hydrogen atom transfer photocatalysis to activate volatile alkanes, such as isobutane, butane, propane, ethane, and methane. Subsequently, these nucleophilic radicals react with SO2 to yield the corresponding sulfinates. These sulfinates then serve as versatile building blocks for the synthesis of diverse sulfur-containing organic compounds, including sulfones, sulfonamides, and sulfonate esters. Our use of flow technology offers a robust, safe and scalable platform for effectively activating these challenging gaseous alkanes, facilitating their transformation into valuable sulfinates.

Synthesis of Mesoporous Silica from Palm Oil Boiler Ash (MS-POBA) with Addition of Methyl Ester Sulfonate as a Template for Free Fatty Acid Adsorption from Crude Palm Oil (CPO)

The synthesis of mesoporous material by utilizing palm oil boiler ash (POBA) waste as the silica source and methyl ester sulfonate (MES) surfactant as the template for a high-porosity was investigated for free fatty acids (FFA) adsorption. The research was initiated with silica extraction from POBA by sodium hydroxide addition through the sol-gel precipitation method. Silica modification was carried out with MES surfactant and 3-aminopropyltrimethoxysilane (APTMS) as the co-structure-directing agent (CSDA) in different calcination temperatures. Mesoporous silica-POBA (MS-POBA) free template had a surface area, pore diameter, and pore volume (41.033 m2/g, 4.180 nm, and 0.250 cm3/g) lower than MS-POBA with the template (71.0147 m2/g, 7.923 nm, and 0.524 cm3/g). The ability of MS-POBA to adsorb FFA reached its optimum conditions with an adsorption time of 20 min and an adsorbent dosage of 0.24 g. The FFA removal by MS-POBA with the template was found to have higher adsorption ability, which was 35.54%, compared to the MS-POBA free template of 26.68%. The high porosity of MS-POBA with a template makes the FFA adsorption capacity of this material higher than MS-POBA free template.

Preparation and optimization of dummy molecularly imprinted polymer-based solid-phase extraction system for selective enrichment of p-toluene sulfonate esters genotoxic impurities

Sulfonate esters, one class of genotoxic impurities (GTIs), have gained significant attention in recent years due to their potential to cause genetic mutations and cancer. In the current study, we employed the dummy template molecular imprinting technology with a dummy template molecule replacing the target molecule to establish a pretreatment method for samples containing p-toluene sulfonate esters. Through computer simulation and ultraviolet–visible spectroscopy analysis, the optimal functional monomer acrylamide and polymerization solvent chloroform were selected. Subsequently, a dummy template molecularly imprinted polymer (DMIP) was prepared by the precipitation polymerization method, and the polymer was characterized in morphology, particle size, and composition. The results of the adsorption and enrichment study demonstrated that the DMIP has high adsorption capability (Q = 7.88 mg/g) and favorable imprinting effects (IF = 1.37); Further, it could simultaneously adsorb three p-toluene sulfonate esters. The optimal adsorption conditions were obtained by conditional optimization of solid-phase extraction (SPE). A pH 7 solution was selected as the loading condition, the methanol/1 % phosphoric acid solution (20:80, v/v) was selected as the washing solution, and acetonitrile containing 10 % acetic acid in 6 mL was selected as the elution solvent. Finally, we determined methyl p-toluene sulfonate alkyl esters, ethyl p-toluene sulfonate alkyl esters, and isopropyl p-toluene sulfonate alkyl esters in tosufloxacin toluene sulfonate and capecitabine at the 10 ppm level (relative to 1 mg/mL active pharmaceutical ingredient (API) samples) by using DMIP-based SPE coupled with HPLC. This approach facilitated the selective enrichment of p-toluene sulfonate esters GTIs from complex API samples.

Two genotoxic impurities of sulfonate esters in Posaconazole: Synthesis, method validation and mechanism of action

AbstractSulfonate esters are a class of organic impurities that includes highly potent mutagenic substances that typically need to be controlled down to a low ppm level in pharmaceutical development. In this work, two genotoxic impurities of sulfonate esters in Posaconazole, for example, ((3S,5R)‐5‐((1H‐1,2,4‐triazol‐1‐yl)methyl)‐5‐(2,4‐difluorophenyl)tetrahydrofuran‐3‐yl)methyl‐4‐methylbenzenesulfonate and (2S,3S)‐3‐ (4‐(4‐(4‐(4‐(((3R,5R)‐5‐((1H‐1,2,4‐triazol‐1‐yl)methyl)‐5‐(2,4‐difluorophenyl)tetrahydrofuran‐3‐yl)methoxy)phenyl)piperazin‐1‐yl)phenyl)‐5‐oxo‐4,5‐dihydro‐1H‐1,2,4‐triazol‐1‐yl)pentan‐2‐yl‐4‐methylbenzenesulfonate, were synthesized and characterized. The genotoxicity which was evaluated by two (quantitative) structure‐activity relationships prediction methodologies showed positive. Furthermore, a novel high‐performance liquid chromatography‐tandem mass spectrometry limit test method for detecting these two impurities in Posaconazole has been established and validated. The chromatographic separation of analytes was conducted on an ACQUITY BEH C18 column, and performed with 0.05% methanoic acid‐water and 0.05% methanoic acid‐acetonitrile as mobile phases A and B, respectively. Six batches of commercial‐scale Posaconazole samples were detected by the validated method and the results were in accordance with the Food and Drug Administration acceptance criteria for the genotoxic impurities in drug substances. Finally, a tentative mechanism for these two impurities was proposed, they are generally accepted to undergo an SN2‐type reaction, resulting in 7‐methylguanine as the predominant adduct in double‐stranded DNA.

Deprotection of the BOC Groups in Poly(2-(tert‑butoxycarbonyloxy)ethyl methacrylate) controlled by the incorporation of polymerizable thermally latent acids

Poly((2‑tert-butoxycarbonyloxy)ethyl methacrylate) (PBHEMA) is converted to poly(2-hydroxyethyl methacrylate) (PHEMA) with the release of isobutene and CO2 by heating and this reaction is accelerated by an acid. The thermally latent acid catalysts (TLA) are useful for the control of a working temperature for the deprotection of the tert‑butoxycarbonyl (BOC) groups included in PBHEMA. In this study, styrene- and methacrylate-type sulfonic esters were synthesized and copolymerized with BHEMA in order to investigate the effect of the TLAs incorporated into the polymer chains. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) were carried out for the copolymers of BHEMA with the polymerizable TLAs in order to discuss the deprotection features of the BOC group in comparison with the results for the systems of PBHEMA blended with the low-molecular-weight TLAs.

Oil spill dispersant formulation from Palmitoyl-DEA and methyl ester sulfonate

Surfactants are chemical compounds that can interact with solvents to reduce surface tension. Palmitoyl-Diethanolamide surfactant (Palmitoyl-DEA) and methyl ester sulfonate (MES) can be applied in dispersing oil in seawater as Oil Spill Dispersant (OSD). An OSD formulation derived from a mixture of two surfactant solutions, namely Palmitoyl-DEA and MES, was found. Diethanolamide non-ionic surfactant solution and anionic methyl ester sulfonate surfactant solution in various concentrations were mixed according to their respective ratios at 50℃ for 60 minutes. The OSD product obtained was then analyzed for density, surface tension, and emulsion stability. OSD products at a concentration of 4% MES and 2% DEA with a 2:1 ratio obtained the best analytical results. The OSD product has excellent density, surface tension, and emulsion stability (> 80%). Furthermore, testing of OSD products was carried out for oil pollution in seawater. The results of simulation tests using OSD products for handling petroleum pollution in seawater (15 mL/L) show an excellent ability to disperse oil (> 90%). The oil and OSD dispersed in seawater showed a more significant increase in COD and BOD values.

Behavior of calcium lignosulfonate under oxygen pressure acid leaching condition

The behavior of calcium lignosulfonate (CLS) in the oxygen pressure acid leaching process of ZnS concentrate was investigated using total organic carbon assessment (TOC), UV–visible spectrophotometry, Fourier transform infrared spectroscopy (FTIR), and gas chromatography-coupled mass spectrometry (GC–MS) as characterization methods. The effect of the CLS degradation products on zinc electrowinning was also discussed. The results showed that the temperature was positively correlated with the degradation of CLS, while the initial acidity had only significant effects in the range of 0–50 g/L and oxygen partial pressure range of 0–0.1 MPa. At an oxygen partial pressure of 0.2 MPa, an acidity of 160 g/L, and a reaction temperature of 150 °C, about 82.4% of CLS was degraded. In the oxygen pressure acid leaching process, CLS underwent polymerization and decomposition reactions, and its aromatic rings and side chain groups were damaged to varying degrees. At 120 °C, CLS was partially converted into sulfonic acids, phenols, and esters of higher molecular weights. At 150 °C, CLS further degraded into lower-molecular-weight aromatic ethers and sulfonic acids with shorter carbon chains. These organics were relatively stable and were the main sources of organic compounds during the oxygen pressure leaching process of zinc concentrates. The addition of CLS had a significant negative impact on zinc electrowinning, which was related to the adsorption of CLS on the cathode surface, enhancing cathodic polarization and inhibiting zinc reduction kinetics.