Sulfonate Esters Research Articles

Molecular Dynamics Simulation of Methyl Ester Sulfonates at the Water/Chloroform Interface

Molecular dynamics simulation method was used to investigate distribution properties of methyl ester sulfonates (MES) with different carbon numbers at the chloroform/water interface. We consider a series of surfactant isomers in the family of methyl ester sulfonates, denoted by CnMES, where n is the number of carbon atoms in the alkyl chain. According to the simulation results, a well-stable interface between the chloroform and water phases could form in the presence of MES surfactants. The simulation results show that stability of interface with C18MES is relatively high comparing to C14MES and C16MES. From the comparison of the interfacial thickness obtained by the density profiles, we could realize that the surfactant C16MES cause the lowest interfacial thickness. Furthermore, we found that the system containing C14MES has the largest interfacial thickness as it shows the best miscibility with chloroform among the other surfactants.

Production of Biodegradable Sulfonated Methyl Ester by a Falling Film Reactor for ASP Flooding in EOR

Petroleum production can be improved through enhanced oil recovery (EOR) methods such as chemical injection. This study focused on sulfonation of methyl ester using SO3 dissolved in oleum compounds (H2SO4.SO3) in a mini-pilot falling film reactor at 70 °C and its application for chemical EOR with ASP flooding. The reactor was equipped with cooling water to facilitate heat transfer in view of the highly exothermic reaction. Biodegradable methyl ester sulfonate, a biosurfactant, was produced from esterification of vegetable oils, palm kernel oil, and coconut oil. The MES products were characterized by Fourier transform infrared testing, which showed S=O and -OH groups peaks, indicating that sulfonation had occurred. The IFT test data showed that the MES from CNO produced the lowest IFT values for light oil and heavy oil, equal to 11.4 mN/m and 10.3 mN/m, respectively. The effect of the MES concentration on the phase behavior was an increase of the IFT value before being applied in ASP flooding, and a decrease after reaching the optimum condition. The EOR core flooding test with the formulated ASP resulted in original oil in place (OOIP) percentages in the range of 12 to 23.5%. The highest acquisition was 23.53% OOIP for an ASP composition of 200 ppm, 0.5%wt, 2800 ppm, respectively.

Structural characterization of naphthalene sulfonamides and a sulfonate ester and their in vitro efficacy against Leishmania tarentolae promastigotes

Structural and biological activity analyses of two naphthalene sulfonamides and a naphthalene sulfonate ester.

Performance of Green Surfactants in the Formulation of Heavy-Duty Laundry Liquid Detergents (HDLD) with Special Emphasis on Palm Based Alpha Methyl Ester Sulfonates (α-MES).

Liquid detergent has an increasing demand in North America, Western Europe, and Southeast Asia countries owing to its convenience to use and efficiency to clean. Alpha methyl ester sulfonates (α-MES), an anionic surfactant derived from palm oil based methyl ester, was reported to have lower manufacturing cost, good detergency with less dosage, excellent biodegradability, higher tolerance to hard water, and lower eco-toxicity as compared to linear alkylbenzene sulfonates (LABS). LABS was known as the workhorse of the detergent industry in the 20th century. Although palm-based α-MES was successfully used as the sole surfactant in powder detergent, there are still some unsettled technical issues related to phase stability and viscosity when using this anionic surfactant in heavy-duty laundry liquid detergent formulations. This paper will review not only the market overview of detergents, the application and performance of green surfactants in laundry detergents but also will highlight the technical issues related to the application of palm-based α-MES in laundry liquid detergent and some of the possible methods to overcome the formulation adversities.

Study on Hydrolysis of Magnesium Hydride by Interface Control

Magnesium hydride (MgH2) is one of the competitive hydrogen storage materials on account of abundant reserves and high hydrogen content. The hydrolysis of MgH2 is an ideal and controllable chemical hydrogen generation process. However, the hydrolyzed product of MgH2 is a passivation layer on the surface of the magnesium hydride, which will make the reaction continuity worse and reduce the rate of hydrogen release. In this work, hydrogen generation is controllably achieved by regulating the change of the surface tension value in the hydrolysis, a variety of surfactants were systematically investigated for the effect of the hydrolysis of MgH2 In the meantime, the passivation layer of MgH2 was observed by scanning electron microscope (SEM), and the surface tension value of the solution with different surfactants were monitored, investing the mechanism of hydrolysis adding different surfactants. Results show that different surfactants have different effects on hydrogen generation. The hydrogen generation capacity from high to low is as follows: tetrapropylammonium bromide (TPABr), sodium dodecyl benzene sulfonate (SDBS), Ecosol 507, octadecyl trimethyl ammonium chloride (OTAC), sodium alcohol ether sulfate (AES), and fatty methyl ester sulfonate (FMES-70). When the ratio of MgH2 to TPABr was 5 : 1, the hydrogen generation was increased by 52% and 28.3%, respectively, at the time of 100 s and 300 s. When hydrolysis time exceeds 80 s, the hydrogen generation with AES and FMES-70 began to decrease; it was reduced by more than 20% at the time of 300 s. SEM reveals that surfactants can affect the crystalline arrangement of Mg(OH)2 and make the passivation layer three-dimensionally layered providing channels for H2O molecules to react with MgH2.

Synthesis, Characterization, and Evaluation of Solution Properties of Sesame Fatty Methyl Ester Sulfonate Surfactant.

The search for alternative, biodegradable, and sustainable raw materials to replace finite petrochemicals is an area of great interest. Triglycerides obtained from oilseed crops are such potential raw materials. In this study, sesame oil was trans-esterified to sesame fatty methyl esters (SEFAMEs) that were used as precursors in the synthesis of sesame fatty methyl esters sulfonate (SEFAMESO) surfactant. SEFAME and SEFAMESO surfactants were characterized by high-performance liquid chromatography–mass spectrometry (HPLC-MS), 1H NMR, and Fourier transform infrared (FTIR) spectra. HPLC-MS, 1H NMR, and FTIR spectra indicated successful trans-esterification and conversion of SEFAMEs to SEFAMESO. Solution properties of the SEFAMESO surfactant including hydrophilic–lipophilic balance (HLB) value, Krafft point, foam-ability, critical micelle concentration (CMC), counterion degree of binding and thermodynamic parameters such as ΔG°mic, ΔH°mic, ΔS°mic, ΔH°mic,* and TC were evaluated. The CMC values of SEFAMESO at 298.15 K were relatively lower than that of the sodium dodecyl sulfate (SDS) standard, and these values decreased to a minimum at 303.15 K and then increased with an increase in temperature. ΔG°mic values were negative indicating a spontaneous micellization process. ΔH°mic and ΔS°mic values revealed that micellization was entropy-driven at low temperatures and both entropy- and enthalpy-driven at high temperatures. ΔH°mic,* values were negative suggesting formation of stable micelles. The evaluated properties revealed the potential application of the synthesized surfactant as a cleansing agent.

Synthesis of polymeric surfactant from palm oil methyl ester for enhanced oil recovery application

Methyl ester sulfonate (MES) is an anionic surfactant derived from natural oils. Polymers are large molecules composed of many repeated units that increase viscosity as a mobility control. Therefore, polymer and surfactant can be reacted into one substance as an alternative for enhanced oil recovery (EOR) application. The principle of this research is to graft sulfonate groups from MES into the polymer chain. Based on the experiments, the best result of polymerization was obtained at a mole ratio of 1:0.3 MES to acrylamide. Based on the interfacial tension (IFT) measurement, the IFT value decreased from 8.6 to 2.3 mN/m before and after the addition of polymeric surfactant respectively. The synthesis of polymeric surfactant obtained a yield of 1384.79%. Polymeric surfactant is potential candidates to change the initial oil-wet state of the quartz surface to water-wet based on wettability alteration study. According to thermal analysis and emulsification behavior, this polymeric surfactant was thermally stable under the desired reservoir temperature and was able to emulsify crude oil. The adsorption study showed that the adsorption onto the rock surface increased when the polymeric surfactant concentration was increased in the system. Core flooding experiments showed an increase in oil recovery in different concentrations of polymeric surfactant. Although the IFT value of polymeric surfactant is not very low, it has the potential as an alternative surfactant for EOR applications.

Novel metabolites of triazophos formed during degradation by bacterial strains Pseudomonas kilonensis MB490, Pseudomonas kilonensis MB498 and pseudomonas sp. MB504 isolated from cotton fields

In the current scenario of overuse of pesticides (resulting in soil and water pollution and ultimately leading to biomagnification), a research project was carried out to study biodegradation of Triazophos. For this purpose, three bacterial strains (Pseudomonas kilonensis MB490, Pseudomonas kilonensis MB498 and Pseudomonas sp. MB504), isolated from cotton fields of Mianwali, Pakistan were investigated for Triazophos degradation and metabolite formation in M-9 broth, soil slurry and soil microcosm after incubation for 9 days. There was 88.4–95.8% Triazophos degradation in M-9 broth, 99.90% degradation in soil slurry and 92.74 to 96% Triazophos degradation in soil microcosm by these bacteria after 9 days. While there was negligible Triazophos degradation (upto 7%) in the controls without bacteria. According to GCMS analysis, 7 unique and novel metabolites (1, 2, 4-Triazole-4—amine, N-(2-Thienylmethyl), Benzene sulfonic acid hydrazide, Benzene sulfonic acid methyl ester, 4H-1,2,4-Triazole-4-benzenesulfonamide, 4, 5 dihydro-N-(O-toyl)-3-furamide, Ethyl 4-phenyldiazenylbenzoate and Dibutyl methanephosphonate) of Triazophos were revealed. Current results strongly suggest the potential of these bacterial strains for the remediation of Triazophos contaminated agricultural soils.

Catalytic performance and deactivation mechanism of a one-step sulfonated carbon-based solid-acid catalyst in an esterification reaction

In this study, catalytic activity and deactivation mechanism of a carbon-based solid-acid catalyst in the esterification of oleic acid and methanol were investigated. The experimental results showed that the S150-4 catalyst, prepared by sulphonating at 150 °C for 4 h, yielded the highest sulfonic acid density. The conversion yield reached 97.98% under the optimum esterification conditions (i.e. catalyst loading, 10 wt%; methanol/oleic acid molar ratio, 8:1; reaction temperature, 65 °C; reaction time, 8 h) and decreased to 79.19% after four cycles. In the first batch of esterification, the formation of sulfonic esters was the main reason for the deactivation of the catalyst, whereas the leaching of sulphur was the main contributor in the second to fourth batches. Therefore, it is believed that reducing the leaching of sulphur and the formation of sulfonic esters by changing the addition method of methanol is an effective method to extend the service life of the catalyst.

A simple method for the synthesis of sulfonic esters

An efficient and simple approach for the direct synthesis of aryl and heteroaryl sulfonic esters was developed using DMS and DES as alkoxysulfonylation reagents. The reaction is operationally simple and scalable. This protocol does not require solvent, expensive catalysts, base, ligand additives or other reagents. A wide range of sulfonic esters were synthesized in moderate to good chemical yields. This method has the advantage of low cost, facile and tolerated a wide range of substrates.

Sulfonate-isosteric replacement examined within heroin-hapten vaccine design

Heroin overdose and addiction remain significant health and economic burdens in the world today costing billions of dollars annually. Moreover, only limited pharmacotherapeutic options are available for treatment of heroin addiction. In our efforts to combat the public health threat posed by heroin addiction, we have developed vaccines against heroin. To expand upon our existing heroin-vaccine arsenal, we synthesized new aryl and alkyl sulfonate ester haptens; namely aryl-mono-sulfonate (HMsAc) and Aryl/alkyl-di-sulfonate (H(Ds)2) as carboxyl-isosteres of heroin then compared them to our model heroin-hapten (HAc) through vaccination studies. Heroin haptens were conjugated to the carrier protein CRM197 and the resulting CRM-immunoconjugates were used to vaccinate Swiss Webster mice following an established immunization protocol. Binding studies revealed that the highest affinity anti-heroin antibodies were generated by the HMsAc vaccine followed by the HAc and H(Ds)2 vaccines, respectively (HMsAc > HAc≫HDs2). However, neither the HMsAc nor H(Ds)2 vaccines were able to generate high affinity antibodies to the psychoactive metabolite 6-acetyl morphine (6-AM), in comparison to the HAc vaccine. Blood brain bio-distribution studies supported these binding results with vaccine efficiency following the trend HAc > HMsAc ≫ H(Ds)2 The work described herein provides insight into the use of hapten-isosteric replacement in vaccine drug design.

Calcium oxalate deposition on cotton fabric in the presence of different anionic surfactants

Sodium oxalate is a detergent builder candidate due to its good performance in detergent formulations. However, sodium oxalate softens water by forming precipitates, thus preventing calcium oxalates from depositing on fabrics is a key goal for sodium oxalate-based detergents. Surfactants and builders are two main ingredients in detergents. Here, six anionic surfactants were chosen to study their deposition effects on cotton fabric during washing. Ash deposition analysis was used to evaluate the amount of calcium oxalate deposition on cotton fabric. X-ray diffractometer and scan electron microscope were performed to the study crystal phase and morphological changes of calcium oxalates in the presence of the different anionic surfactants, and the total interaction energy between calcium oxalates and cotton fabric was calculated by Derjaguin–Landau–Verwey–Overbeek (DLVO) theory in each case. The results showed that different anionic surfactants have a different effect on the ash deposition, primarily that the concentration of surfactants had less influence on the deposition with the exceptions of sodium dodecyl benzene sulfonates (SDBS) and sodium methyl ester sulfonates (MES). Anionic surfactants can influence both phase and morphology of calcium oxalates, which might influence the zeta potential of the calcium oxalates. When the calcium oxalates are of the same phase, the deposition amount decreased with increasing maximum total interaction energy (VTmax). The greatest decrease in calcium oxalates deposition occurred in the presence of sodium alkyl ether sulfates (AES) and disodium lauryl sulfosuccinates (AEMES), of which VTmax is the largest.

Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin’s protein-protein interaction with the 26S proteasome. We previously published a study exploring the aryl sulfonate ester of cjoc42 in an effort to enhance gankyrin binding and inhibit cancer cell proliferation. In order to further improve the gankyrin binding ability of the cjoc42 scaffold, an extensive SAR for the aryl-triazole moiety of cjoc42 was developed. Our cjoc42 derivatives exhibited enhanced gankyrin binding, as well as enhanced antiproliferative activity against Hep3B, HepG2, A549, and MDA-MB-231 cancer cell lines.

Microemulsion synthesis of anhydrous calcium sulfate nanowhiskers with calcium acetate solution and its surface structure stable and crystal phase evolution after modification

Methods obtaining gypsum whiskers via calcining dihydrate or hemihydrate gypsum perform high energy consumption. It also performs potential environmental impacts. New methods with energy-saving, high-efficiency, and environmentally friendly perform great challenges, which aim at fabricating gypsum whiskers even nanowhiskers. In this study, we used high-concentration calcium acetate solution and dilute sulfuric acid to fabricate anhydrite calcium sulfate nanowhiskers with microemulsion solution at room temperature. For further research on regulation and modification of its surface, calcium sulfates were modified by silicone quaternary ammonium salt and fatty acid methyl ester sulfonate in order to study their surface structure and crystal evolution during modification. After characterization, it indicated that the phase of calcium sulfate transmitted from anhydrite phase into dihydrite phase with a slight change on the surface layers. Benefiting from stability and activity properties of calcium sulfate nanowhiskers after modified, the compressive strength of cement paste with only 1% calcium sulfates performed increased absolutely 10.1% and 4.3% at conservation age of 3 days and 28 days.

Evaluation of calcium oxalate deposition on different fabrics under different sodium oxalate-based detergent formulations

The builder is an important ingredient in detergents. Sodium oxalate is a good non-phosphate detergent builder, which has good calcium-removing properties and good wash performance in detergents. However, sodium oxalate-based detergent formulations face a tricky problem of “incrustation” on fabrics due to calcium oxalate deposition. If sodium oxalate is used in commercial detergents, then “incrustation” must be solved. In this study, we examined the effect of fabric type, anionic surfactant, polymer, and temperature on incrustation and soil redeposition (“secondary” washing effect) of a sodium oxalate-based detergent. The results showed that both the anionic surfactant and polymer influenced the deposition of calcium oxalate on fabrics. Overall, the amount of calcium oxalate deposition followed the order polyamide < polyester < cotton with the same formulation. Finally, good secondary washing effects (low ash deposition and high whiteness retention) formulations were selected by cumulative washing. The formulation of methyl ester sulfonate (MES)-sodium carboxymethyl cellulose (CMC), MES-polyvinyl pyrrolidone, and alcohol ether sulfate (AES)-CMC had better secondary effects, and the optimal combination of the 12 formulations was AES-CMC.

Regio-isomeric isoxazole sulfonates: Synthesis, characterization, electrochemical studies and DNA binding activity

The transformation of 3,5-bis hydroxypheny-1,2-isoxazoles to their sulfonate ester derivatives is being described. The synthesis of the products was confirmed using FT-IR, NMR, and X-ray diffraction analysis. Subsequently the electrochemical and DNA binding studies of the synthesized compounds were executed. Electrochemical studies of compounds were carried out using cyclic voltammetry (CV). Results from cyclic voltammetry depicted that the synthesized compounds demonstrate one electron oxidation. CV titrations were employed to study interactions between synthesized isoxazole derivatives and DNA, which revealed intercalative interaction of the synthesized compounds with DNA. Compound 4 exhibited highest DNA interaction with the value of 9.03 × 104 M−1 for the binding constant (K).

Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates.

While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this challenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% ± 11% average yield). Mechanistic studies show that Pd strongly prefers the aryl triflate, the Ni catalyst has a small preference for the aryl tosylate, aryl transfer between catalysts is mediated by Zn, and Pd improves yields by consuming arylzinc intermediates.

Preparation of magnetorheological fluid with excellent sedimentation stability

ABSTRACT In order to prepare magnetorheological fluid with excellent sedimentation stability, various surfactants are applied to coat carbonyl iron powder. The prepared magnetorheological fluid shows excellent sedimentation stability when the surfactants are respectively sodium lauryl alcohol phosphate, compound sodium fatty acid methyl ester sulfonate, ethylene glycol monostearate and glyceride monostearate. Orthogonal tests are carried out for the optimal combination of surfactants and thixotropic agent. The experimental results show that the optimal combination of additives for MRF is 1.5 wt% of sodium lauryl alcohol phosphate, 1.0 wt% of compound MES, 1.5 wt% of ethylene glycol monostearate, 1.5 wt% of glycerol monostearate and 1.0 wt% of hydrophobic fumed silica. Magnetorheological fluid is prepared by the compound scheme, of which the viscosity is 1.09 Pa·s at 25.9°C and the sedimentation rate is 1.61% after one-week placement. The novel MRF is in excellent sedimentation stability and fluidity.

Enhanced Cellular Uptake and Photodynamic Effect with Amphiphilic Fluorinated Porphyrins: The Role of Sulfoester Groups and the Nature of Reactive Oxygen Species

A class of amphiphilic photosensitizers for photodynamic therapy (PDT) was developed. Sulfonate esters of modified porphyrins bearing—F substituents in the ortho positions of the phenyl rings have adequate properties for PDT, including absorption in the red, increased cellular uptake, favorable intracellular localization, low cytotoxicity, and high phototoxicity against A549 (human lung adenocarcinoma) and CT26 (murine colon carcinoma) cells. Moreover, the role of type I and type II photochemical processes was assessed by fluorescent probes specific for various reactive oxygen species (ROS). The photodynamic effect is improved not only by enhanced cellular uptake but also by the high generation of both singlet oxygen and oxygen-centered radicals. All of the presented results support the idea that the rational design of photosensitizers for PDT can be further improved by better understanding the determinants affecting its therapeutic efficiency and explain how smart structural modifications can make them suitable photosensitizers for application in PDT.

Development of environment-friendly oil-in-water emulsion based drilling fluid for shale gas formation using sunflower oil

Mineral oils are frequently used for the making of synthetic-based drilling fluids. However, there are several downsides associated with these oils. These mineral oils are non-renewable, toxic in nature, non-biodegradable and prompting towards the incredible expense of waste treatment. In this research article, an anionic surfactant sodium methyl ester sulfonate (SMES) was synthesized using sunflower oil. SMES is then used to formulate environment-friendly oil-in-water emulsion-based drilling fluid. The synthesized surfactant is characterized by FT-IR, 1H-NMR and TGA analysis. The effect of xanthan gum (XG), bentonite, and sodium methyl ester sulfonate (SMES) on the rheology and filtration characteristics of developed emulsion based drilling fluid was analyzed thoroughly. The developed emulsion based drilling fluid had lower friction coefficient in case of oil concentration compared to SMES concentration. The zeta potential has been measured to check the emulsion stability and it has been attended that an increase in the concentration of SMES (0.3–0.7 wt/v %) and xanthan gum (0.2–0.6 wt/v %) has improved the stability of the emulsion. The contact angle and interfacial tension were analyzed and it was observed that interfacial tension was reduced from 102.5 to 25.35 mN/m and contact angle increased from 32.5° to 92.3°. The thermal stability of oil-in-water emulsion based drilling fluid was maintained up to 140 °C.