Alkyl Ether Sulfate Research Articles

Reversible Splenial Lesion in the Corpus Callosum on MRI after Ingestion of a Herbicide Containing Glufosinate Ammonium: A Case Report

Glufosinate ammonium (GLA) is a broad-spectrum herbicide used worldwide. As the use of GLA-containing herbicides has increased, poisoning from incidental and deliberate ingestion has also increased, and has been mostly reported from Japan. Most of glufosinate poisoning events were associated with suicide attempts using BASTA® (Bayer, Leverkusen, Germany). BASTA®, a herbicide containing glufosinate ammonium (18.5%) and the anionic surfactant, polyoxyethylene alkylether sulfate (30%), has been widely used in many countries since 1984 (1). Glufosinate poisoning has been reported to induce central nervous system (CNS) symptoms, such as drowsiness, memory impairment, and seizures. Also, the included anionic surfactant, which increases blood vessel permeability, may cause symptoms such as reduced circulatory blood volume, altered cardiac function, and systemic peripheral vessel resistance (1). Periventricular white matter ischemias, hippocampal lesions, and both hippocampal and striatal lesions have been reported following GLA intoxication, together with radiological findings (2, 3). We describe a patient who developed a reversible callosal lesion by ingesting a GLA-containing herbicide in an attempted suicide.

Optimization of Application Efficacy for POST Herbicides with Adjuvants on Three-Cornered Jack (Emex australis Steinheil) in Wheat

Field studies were conducted to evaluate POST herbicides with adjuvants for the control of three-cornered jack in winter wheat. The herbicides evaluated were fluroxypyr 9.7% w/w + MCPA 38.8% w/w (formulated mixture [450 g ai ha−1]), carfentrazone-ethyl (20 g ai ha−1), bromoxynil 26.8% w/w + MCPA 40.0% w/w (formulated mixture [450 g ai ha−1]), thifensulfuron-methyl (75 g ai ha−1), and tribenuron-methyl (75 g ai ha−1), applied alone or tank mixed with the adjuvants alkyl ether sulfate sodium salt (625 mL ha−1) or fatty alcohol ethoxylate (375 mL ha−1). The addition of adjuvants to carfentrazone-ethyl resulted in > 94% control of three-cornered jack. Both adjuvants enhanced the efficacy of all herbicides for control of three-cornered jack, except thifensulfuron-methyl. However, a maximum increase in phytotoxicity on three-cornered jack was achieved with the addition of either adjuvant to tribenuron-methyl compared with herbicides used alone. Bromoxynil + MCPA and carfentrazone-ethyl gave maximum wheat yield and yield components.

Phytotoxic effects of herbicide Attribut and surfactant BioPower on the root, stem, and leaf anatomy of Triticum aestivum ‘Pehlivan’

This study was performed in order to determine toxic effects of different doses of Attribut (propoxycarbazone-sodium) used in wheat fields and BioPower (sodium alkyl ether sulphate) surfactant added to Attribut on Triticum aestivum L. ‘Pehlivan’. The doses used in the study were 0.42 mM Attribut, 0.82 mM Attribut, and 1.68 mM Attribut with or without 0.25% BioPower. Laboratory studies showed that the effective concentration value corresponded to the farmer dose, 0.42 mM Attribut. Applications were done by seed treatment. The effects of each of the doses applied to wheat plants were monitored in terms of anatomical parameters. Attribut doses of 0.82 mM and above had toxic effects on wheat plants, and these effects increased with the use of BioPower. As a response to the stress, the diameter in the general structure of the roots narrowed, the cuticle thickened, cleavages in parenchyma cells developed, and cell walls in the sclerenchyma cells and endodermis thickened.

Optimizing activity of herbicides at reduced rate on Emex spinosa campd. with adjuvants

In pot experiments, two adjuvants were evaluated for their efficacy in enhancing activity of five herbicides applied at reduced rates (75% of the recommended rates) on Emex spinosa at the cotyledon-leaf and at the two- to four- leaf stage. Herbicides (at recommended rates) including fluroxypyr+MCPA at 450 g a.i. ha-1, carfentrazone-ethyl at 20 g a.i. ha-1, bromoxynil+MCPA at 450 g a.i. ha-1, thifensulfuron-methyl at 75 g a.i. ha-1 and tribenuronmethyl at 75 g a.i. ha-1 alone and tank mixed at reduced rates with adjuvants, namely, alkyl ether sulphate sodium salt at 625 mL ha-1 or fatty alcohol ethoxylate at 375 mL ha-1. Addition of the adjuvants to reduced rates of fluroxypyr+MCPA and carfentrazone-ethyl, increased their efficacy with 100% mortality and biomass reduction of E. spinosa at the cotyledon- leaf stage and at the two- to four- leaf stage which was similar to their recommended rates without the adjuvants except for carfentrazone-ethyl at a reduced rate without adjuvants at the two- to four- leaf stage. Bromoxynil+MCPA at reduced rates with alkyl ether sulphate sodium salt also gave 100% control of E. spinosa over weedy check at the two- to four- leaf stage. Both the adjuvants generally increased the efficacy of tribenuron-methyl at reduced rates when sprayed at both leaf stages. These findings suggest that the use of adjuvants may increase the efficacy of the above mentioned herbicides against E. spinosa and it may be incorporated in an integrated weed management program.

Structure–Behavior–Property Relationship Study of Surfactants as Foam Stabilizers Explored by Experimental and Molecular Simulation Approaches

A multiscale stability study of foams stabilized by sodium dodecyl sulfate (SDS), sodium dodecylbenzene sulfonate (SDBS), and sodium polyoxyethylene alkylether sulfate (AES) was conducted, to investigate the relationship of surfactant molecular behavior and interfacial monolayer configuration of foam film to the foam film properties. Molecular dynamic (MD) simulations using a full-atom model was utilized to explore the microscopic features of the air/liquid interface layer. Several parameters such as the distribution of surfactant head groups and the order degree of surfactant hydrophobic tails were used to describe the molecular adsorption behavior. The effect of molecular structure on the nature of the foam film and the impact on the dynamic stability of wet foam is discussed. In the experimental evaluation, the SDBS foam films manifest strong stiffness and low viscoelasticity as shown by the interfacial shear rheology determination as well as texture analyzer (TA) measurement results, which agree very well with the array behavior of SDBS molecules at the air/water interface as described by the simulation results and is identified to be the reason for the poor dynamic stability. Comparing the molecular structure of SDS, SDBS, and AES, the special contributions of the linking groups such as the O atom, the phenyl group, and the EO (oxyethyl) chain to the interfacial array behavior of surfactants were characterized. It is concluded that microhardness of the foam film enhanced by rigid linking groups favors static foam stability but decreases the dynamic foam stability, while viscoelasticity of the foam film enhanced by soft linking groups increases the dynamic foam stability.

A Process for the Production of Φ-Sulfo Fatty Methyl Ester Sulfonates (Φ-MES)

AbstractΦ-Sulfo Fatty Methyl Esters sulfonates (Φ-MES) were obtained via sulfoxidation of fatty acid methyl esters (FAME) with SO2, O2, and ultraviolet light of appropriate wavelength. Expectedly, these products may be used as linear alkylbenzene sulfonate (LAS) and alkyl ether sulfate (AES) partners, either in heavy-duty or in hand dishwashing liquids. Φ-MES are new anionic surfactants that can be regarded as potential components for detergent formulations and body care products as well. In this work we summarize the most relevant results of our research started fifteen years ago, on the synthesis, separation and analysis of Φ-sulfo fatty methyl ester sulfonates known as Φ-MES, and we update our last findings. We have to point out that we are for the time being, the only research group in the world to have published our research on Φ-MES. This paper describes the optimum batch conditions for the sulfoxidation of FAME and a reaction mechanism is proposed. The paper depicts an improved workup for the separation of reaction products from non reacted methyl ester and the GC-MS analysis of Φ-sulfo fatty methyl ester sulfonate is shown. Finally, an interpretation of conversion and selectivity of sulfoxydation reaction is given.

Characterization and quantitative analysis of surfactants in textile wastewater by liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry

A method based on the application of ultra-performance liquid chromatography (UPLC) coupled to hybrid quadrupole-time-of-flight mass spectrometry (QqTOF-MS) with an electrospray (ESI) interface has been developed for the screening and confirmation of several anionic and non-ionic surfactants: linear alkylbenzenesulfonates (LAS), alkylsulfate (AS), alkylethersulfate (AES), dihexyl sulfosuccinate (DHSS), alcohol ethoxylates (AEOs), coconut diethanolamide (CDEA), nonylphenol ethoxylates (NPEOs), and their degradation products (nonylphenol carboxylate (NPEC), octylphenol carboxylate (OPEC), 4-nonylphenol (NP), 4-octylphenol (OP) and NPEO sulfate (NPEO-SO4). The developed methodology permits reliable quantification combined with a high accuracy confirmation based on the accurate mass of the (de)protonated molecules in the TOFMS mode. For further confirmation of the identity of the detected compounds the QqTOF mode was used. Accurate masses of product ions obtained by performing collision-induced dissociation (CID) of the (de)protonated molecules of parent compounds were matched with the ions obtained for a standard solution. The method was applied for the quantitative analysis and high accuracy confirmation of surfactants in complex mixtures in effluents from the textile industry. Positive identification of the target compounds was based on accurate mass measurement of the base peak, at least one product ion and the LC retention time of the analyte compared with that of a standard. The most frequently surfactants found in these textile effluents were NPEO and NPEO-SO4 in concentrations ranging from 0.93 to 5.68 mg/L for NPEO and 0.06 to 4.30 mg/L for NPEO-SO4. AEOs were also identified.

Cardiovascular effects of herbicides and formulated adjuvants on isolated rat aorta and heart

Various formulations of agricultural chemicals, including solutions, wettable powders, and emulsifiable concentrates, contain adjuvants of solvents and surfactants in addition to active ingredients. Among these formulations, herbicides are among the most commonly used pesticides globally. Some pesticides have been demonstrated to cause severe circulatory failure in poisoned humans. To clarify the potential risk of herbicides and their adjuvants influence on the cardiovascular system, four technical grade (TG) herbicides and their end products (EP), including paraquat, glyphosate, glufosinate, and atrazine, as well as their formulated adjuvants isopropylamine (IPA), polyoxyethylene alkylether sulfate (AES), ethyl acetate (EA), xylene, petrolium-170 (P-170), and solvesso-100 (S-100), were assessed to determine their effects on isolated rat aorta and heart. The results revealed that the vasorelaxation effects of the herbicide EPs exceeded those of TGs, and atrazine produced more significant vasorelaxation in rat aortas than the other herbicides tested. The formulated adjuvants of IPA did not affect the aorta; however, AES, EA, xylene, P-170 and S-100 caused significant vasorelaxation. Herbicide EPs-induced vasorelaxation was generally endothelium-dependent. Furthermore, the TG and EP of paraquat, and the TG of glufosinate and glyphosate were found to have no effect on the isolated heart. However, the normal twitch tensions of the isolated heart were significantly inhibited by EPs of glyphosate and glufosinate, and by TG and EP of atrazine. Although, the adjuvants of IPA appeared unaffected, however, AES, EA, xylene, P-170 and S-100 caused complete inhibition and contraction on the isolated hearts. These results indicated that the adjuvants of herbicides might enhance hypotension and contributed to cardiovascular disorders during intoxication.

Effect of equilibrium and dynamic surface activity of surfactant on foam transport in porous medium

An apparatus containing a visual porous medium plate model and digital video recorder was employed to investigate the transportation of foam stabilized by sodium polyoxyethylene alkylether sulfate (AES), sodium dodecyl benzene sulfonate (SDBS) and TritonX-100 in porous medium. The results showed that transfiguration and fracture were the main transport manners for foam in the porous medium at high gas and liquid transfusion rate. The increase in probability of transfiguration in foam transport process corresponded to the higher flow impedance. A simple U-shape device was designed to investigate the rigidity of surfactant layer at the gas/liquid interface, and the equilibrium surface tension was assigned to be the key parameter which manifests the rigidity of surfactant interface layer. The dynamic surface tension of different surfactant system has also been measured, and the parameters gotten by Rosen model might be the measurement of dynamic elasticity of surfactant interface layer. There is consanguineous relation between the equilibrium surface activity or dynamic activity of the surfactants and the transport of the foam in the porous medium.

Protease autolysis in heavy-duty liquid detergent formulations: effects of thermodynamic stabilizers and protease inhibitors

Autolysis has been identified as the primary mode of subtilisin activity loss in a heavy-duty liquid detergent (HDLD) formulation containing 10% linear alkylbenzene sulfonate (LAS), 6% alkylether sulfate (AES), and 8% alcohol ethoxylate (AE). Circular dichroism (CD) and Fourier-transform infrared (FTIR) spectra indicate that the protease, a Bacillus lentus subtilisin variant, largely retains its native structure within this formulation. The autolysis reaction is second-order in protease concentration, and a mechanism is proposed wherein both the thermodynamic stability (ΔGunfolding) and Michaelis–Menten catalytic efficiency (kcat/KM) of the enzyme influence the overall autolysis rate. Estimates of ΔGunfolding were calculated from experimental values of the second-order autolysis rate constant using kcat/KM as determined against the synthetic substrate N-succinyl-Ala-Ala-Pro-Phe-p-nitroanilide (suc-AAPF-pNA). Sucrose, a known protein stabilizer, was added to the HDLD formulation at a concentration of 0.5M. The resulting 0.5kcal/mol increase in ΔGunfolding reduced the second-order autolysis rate constant by 50%. Conversely, addition of the chelating agent EDTA removed bound Ca2+ ions from the subtilisin, destabilizing it by ∼4kcal/mol; the autolysis rate constant was increased roughly 10,000-fold. Subtilisin inhibitors (borax/propylene glycol) were used to reduce kcat/KM, and concomitant decreases in the autolysis rate were observed. Possible strategies to reduce protease autolysis by thermodynamic stabilization and/or kinetic inhibition are discussed.

Distribution of Calcium Ion in Wash System and Detergency: Calcium Ion Interaction with Surfactants, Builders and Cotton Fabrics

Investigation of the distribution of calcium ions in the wash system was conducted to clarify the interaction between calcium ions and surfactant, builder and cotton fabric in the range of low water hardness. In the presence of cotton fabric, sodium alkyl ether sulfate (AES) was clearly hard to compound salt with calcium than linear alkyl benzene sulfonate (LAS). Polyoxyethylene alkyl ether (AE) showed the lowest ability to compound with calcium ions. The data also suggest that some of the calcium ions in the solution were adsorbed into cotton fabric prior to compound with surfactant or to be bound by builder in the solutions. The relationship of calcium ion distribution to detergency clearly indicated less calcium to remain in solution with greater detergency. Detergency was greatest for the solution containing both 0.022% AE and 0.015% sodium tripolyphosphate (STPP), and equivalent to that of using 0.023% Zeolite. For greater detergency, AES or AE should be used as surfactant and Zeolite concentration should be at least 0.023%.

Forensic Toxicological Determination of Surfactant by Liquid Chromatography/Electrospray lonization Mass Spectrometry and Liquid Chromatography/Electrospray lonization Tandem Mass Spectrometry.

A procedure for identifying surfactants was investigated by liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) and liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) from the forensic toxicological point of view. The analysis of anionic, cationic, and nonionic surfactants in both negative and positive mode revealed that anionic and cationic surfactants are detected as M- ions in the negative mode and M+ ions in the positive mode, respectively, while [M+H]+ ions or [M+NH4]+ ions appeared for nonionic surfactants in the positive mode. Anionic surfactants (linear alkylbenzene sulfonate and polyoxyethylene alkyl ether sulfate) were successfully extracted using a weak anion exchange cartridge, with recovery rates of 53.8-76.7%. Cationic surfactant (benzalkonium) was also easily extracted using a weak cation exchange cartridge with a recovery rate of 107%. When aqueous solutions of cationic, anionic, and nonionic surfactants were concentrated to dryness, the recovery rates ranged from 65.8% to 124%. By analyzing anionic surfactants (alpha-olefine sulfate, polyoxyethylene alkyl ether sulfate, and linear alkylbenzene sulfonate) in the product ion scan mode in LC/ESI-MS/MS, it was possible to identify the structure of the hydrophilic group of surfactants, and MS/MS was confirmed to be a powerful technique for classification.

Sulfoxylated methyl esters as potential components of liquid formulations

AbstractSulfoxylated methyl esters (Φ‐MES) are obtained via sulfoxidation of fatty acid methyl esters with SO2, O2, and ultraviolet light of appropriate wavelength. These products may be used as co‐surfactants with linear alkylbenzene sulfonate and alkyl ether sulfate, either in heavy‐duty or in hand dishwashing liquids. Standard hand dishwashing formulations based on Φ‐MESC16 are presented and discussed with regard to solubility, viscosity, performance, and skin compatibility. The experimental results obtained indicate that the above‐mentioned products can be regarded as potential components for liquid formulations.

Determination of anionic surfactants during wastewater recycling process by ion pair chromatography with suppressed conductivity detection

A direct approach utilizing ion pairing reversed-phase chromatography coupled with suppressed conductivity detection was developed to monitor biodegradation of anionic surfactants during wastewater recycling through hydroponic plant growth systems and fixed-film bioreactors. Samples of hydroponic nutrient solution and bioreactor effluent with high concentrations (up to 120 mS electrical conductance) of inorganic ions can be analyzed without pretreatment or interference. The presence of non-ionic surfactants did not significantly affect the analysis. Dynamic linear ranges for tested surfactants [Igepon TC-42, ammonium lauryl sulfate, sodium laureth sulfate and sodium alkyl (C 10–C 16) ether sulfate] were 2∼500, 1∼500, 2.5∼550 and 3.0∼630 μg/ml, respectively.

Collector–frother interaction in column flotation of Florida phosphate

This study examines main and interaction effects of frother type, collector and pH on the efficiency of column flotation of Florida phosphate. Two types of frothers are used including sodium alkyl ether sulfate, as an anionic frother, and mixed polyglycols as a nonionic frother. A mixture of fatty acid and fuel oil is used as a collector. The results show that column flotation, depending on the operating conditions, can give phosphate concentrates of high grade (∼31% P 2O 5) at a recovery as high as (∼99%). However, interaction between frothers and the collector and consequently the flotation efficiency were found to be dependent on frother type. Specifically, anionic frother was found to lose its ability to stabilize the froth in the presence of low dosages of collector. An anionic frother used in the presence of conditioning water containing residual collector (i.e., supernatant water after conditioning solids with collector) resulted in a significant reduction in recovery. This phenomenon does not occur with the polyglycol (nonionic) frother. Flotation results of the three-phase system have been confirmed by results obtained in two-phase experiments where a low dosage of collector is added while measuring air hold-up in the presence of different frothers. The residual collector reduces air hold-up and increases bubble size when added with the alkyl ether sulfate (anionic) frother. On the other hand, a synergistic effect was obtained in the presence of the nonionic frother.

Isolation and Analysis of Tetraheme-Bound-Cytochrome from Photosynthetic Reaction Centers of Rhodopseudomonas viridis

A tetraheme cytochrome (BCytc) was isolated from the photosynthetic reaction centers (RC) of Rhodopseudomonas viridis while maintaining the redox activity. BCytc was removed from the H-subunit-detached RC by polyacrylamide electrophoresis using an alkyl ether sulfate mixed with sodium dodecyl sulfate. Redox titration of BCytc showed a simple one-step redox titration curve and a lowered midpoint potential than that of one in RC. Direct electron transfer between BCytc and electrode surfaces, such as indium tin oxide, was successfully performed, indicating a potential for molecular electronic material.

Redox properties of an H-subunit-depleted photosynthetic reaction center from Rhodopseudomonas viridis

Recently, we reported that a H-subunit-depleted photosynthetic reaction center (RC-H) was purified from purple nonsulfer photosynthetic bacterium Rhodopseudomonas viridis ( Rps. viridis) using a strong detergent sodium alkyl ether sulfate. We compared the redox properties of a native photosynthetic reaction center (RC) and RC-H of Rps. viridis. In RC-H prepared by our method, secondary quinone (Q B) was removed while primary quinone (Q A) was retained. Absorption spectrum of RC-H was similar to that of RC. After reconstitution of ubiquinone 10 into Q B sites, RC-H showed electron transfer activity that was the same as that for native RC. This is the first report about the redox properties of RC-H of Rps. viridis.

Sodium alkyl ether sulfate preparative electrophoresis for the preparation of reaction centers without H-subunit from Rhodopseudomonas viridis.

Sodium alkyl ether sulfate (AES), an analog of sodium dodecyl sulfate (SDS) was used in polyacrylamide gel electrophoresis (PAGE) for the partial decomposition of the photosynthetic reaction center (RC) of Rhodopseudomonas viridis. Unlike SDS, AES did not completely dissociate RC into its subunits but selectively detached H-subunit from RC to give RC(-H) without losing the spectroscopic nature of RC. For the denaturation of RC(-H), AES was found to be as mild as 3-[3-cholamidopropyl)dimethylammonio]-l-propanesulfonate (CHAPS).

Effect of oil composition on physical properties and spread width of polyester multifilament for spinning a composite yarn

This study examines the effect of oil composition (including the anti‐static agent ‐ alkyl ether sulfate) on the physical properties and spread width of polyester multifilament for spinning a composite yarn. The results show that the solid content and viscosity of a special oil are slightly lower than normal oil, which reduces the stickiness of the spreading multifilament. Also, the coefficient of kinetic friction μk and electrical conductivity of oiled polyester multifilaments are higher than normal oil in order to conduct and store charges, and to divide easily and spread widely to maintain good spreading performance. The content of the anti‐static agent is the most important component of a special oil. For example, the amount of alkyl ether sulfate (RO(CH2CH2O)nSO3Na) should be 14% to reduce electrical resistance, and increase spreading performance. Furthermore, the number n of oxyethylene groups(CH2CH2O) on alkyl ether sulfate is 2 or 3 in order to maintain a lower electrical resistance and wider spread width.

Cardiovascular Effects of a Herbicide Containing Glufosinate and a Surfactant:In Vitroandin VivoAnalyses in Rats

A herbicide, Basta (BASTA), containing glufosinate ammonium (GLA) as the main component and an anionic surfactant, sodium polyoxyethylene alkylether sulfate (AES), causes hemodynamic changes characterized by a decrease in total vascular resistance with an increase or a decrease in cardiac output in human acute oral poisoning. With a motivation based on these clinical observations, we tried to elucidate the exact component and its mode of action that is mostly responsible for the direct cardiovascular effects of this herbicide formulation, investigating the effects of BASTA, GLA, and AES independently on the cardiovascular system in ratsin vitroandin vivo.In isolated right atria beating spontaneously in Krebs–Ringer's solution, BASTA and AES produced negative chronotropic responses in a concentration-dependent manner. In electrically driven isolated left atria, BASTA and AES produced positive inotropic responses concentration dependently but negative inotropic responses at extremely high concentrations. In aortic ring segments, BASTA and AES produced no vasoconstrictive effects but exerted significant vasodilative effects when the aortic ring was precontracted with phenylephrine. Thesein vitroresponses caused by BASTA and AES occurred to a similar degree. On the other hand, the main component, GLA, produced no effects in isolated atria and aortas. In anesthetized rats, relatively low doses of BASTA and AES produced a decrease in blood pressure followed by a slight increase in heart rate, which was presumably due to baroreflex caused by the decrease in blood pressure. At an extremely high dose, BASTA and AES produced a decrease in blood pressure with a marked decrease in heart rate. Thesein vivoresponses to BASTA and AES also occurred to a similar degree. In contrast, the main component, GLA, did not produce any effects on heart rate and blood pressure in anesthetized rats. From these results, we concluded that the effects of BASTA in ourin vivoexperiments were not caused by the main component, GLA, but was mostly caused by AES through its vasodilative effects plus cardiostimulatory effects at low doses and cardiosuppressive effects at high doses.