Sodium 2-bromoethanesulfonate Research Articles

Unraveling prevalence of homoacetogenesis and methanogenesis pathways due to inhibitors addition

Three inhibitors targeting different microorganisms, both from Archaea and Bacteria domains, were evaluated for their effect on CO2 biomethanation: sodium ionophore III (ETH2120), carbon monoxide (CO), and sodium 2-bromoethanesulfonate (BES). This study examines how these compounds affect the anaerobic digestion microbiome in a biogas upgrading process. While archaea were observed in all experiments, methane was produced only when adding ETH2120 or CO, not when adding BES, suggesting archaea were in an inactivated state. Methane was produced mainly via methylotrophic methanogenesis from methylamines. Acetate was produced at all conditions, but a slight reduction on acetate production (along with an enhancement on CH4 production) was observed when applying 20 kPa of CO. Effects on CO2 biomethanation were difficult to observe since the inoculum used was from a real biogas upgrading reactor, being this a complex environmental sample. Nevertheless, it must be mentioned that all compounds had effects on the microbial community composition.

Effective construction of anti-fouling zwitterion-functionalized ceramic membranes for separation of oil-in-water emulsion based on PDA/PEI co-deposition

Ceramic membranes have been widely used in oil-water separation owing to their characteristics of high flux, excellent chemical stability, strong hydrophilicity, and good fouling resistance. To further enhance their anti-fouling performance, a co-deposition reaction was employed for the surface modification of the ceramic membranes in this study. Polyethyleneimine and dopamine were used to introduce tertiary amine groups on the surface of the ceramic membranes, and sodium 2-bromoethanesulfonate was used for the quaternization reaction with tertiary amine groups. According to the water contact angle measurements, the ceramic membrane functionalized via zwitterionic modification exhibited better hydrophilicity and thus could absorb water droplets faster than pristine ceramic membranes. Consequently, the zwitterion-functionalized ceramic membrane achieved double the permeance (40 L m−2 h−1 bar-‍1) compared to the original ceramic membrane (20 L m−2 h−1 bar-‍1) during the separation of the oil-in-water emulsion, suggesting good anti-fouling performance.

Physiological Effects of 2-Bromoethanesulfonate on Hydrogenotrophic Pure and Mixed Cultures.

Mixed or pure cultures can be used for biomethanation of hydrogen. Sodium 2-bromoethanesulfonate (BES) is an inhibitor of methanogenesis used to investigate competing reactions like homoacetogenesis in mixed cultures. To understand the effect of BES on the hydrogenotrophic metabolism in a biomethanation process, anaerobic granules from a wastewater treatment plant, a hydrogenotrophic enrichment culture, and pure cultures of Methanococcus maripaludis and Methanobacterium formicicum were incubated under H2/CO2 headspace in the presence or absence of BES, and the turnover of H2, CO2, CH4, formate and acetate was analyzed. Anaerobic granules produced the highest amount of formate after 24 h of incubation in the presence of BES. Treating the enrichment culture with BES led to the accumulation of formate. M. maripaludis produced more formate than M. formicicum when treated with BES. The non-inhibited methanogenic communities produced small amounts of formate whereas the pure cultures did not. The highest amount of acetate was produced by the anaerobic granules concomitantly with formate consumption. These results indicate that formate is an important intermediate of hydrogenotrophic metabolism accumulating upon methanogenesis inhibition.

Preparation and characterization of a novel hydrophilic interaction/ion exchange mixed-mode chromatographic stationary phase with pyridinium-based zwitterionic polymer-grafted porous silica.

Novel zwitterionic polymer-grafted porous silica microspheres were prepared by using sodium 2-bromoethanesulfonate to quaternize the pyridyl side chains of the polymer, which is anchored on the surface of porous silica. The separation behavior for toluene and benzoic acid proved that the zwitterionic polymer-grafted porous silica worked as a stationary phase in hydrophilic interaction/ion exchange mixed-mode chromatography. Compared with a conventional sulfobetaine-based zwitterion-grafted porous silica column, the prepared poly(vinylpyridinium ethanesulfonate)-immobilized porous silica afforded the highly selective separation of benzoic acid derivatives over a wide pH range, and the separation behavior was quite sensitive to the protonation state of the carboxylic acids. The high selectivity was attributed to the multiple interactions between the guest molecule and the zwitterionic groups on the polymer chains. The new zwitterionic stationary phase demonstrated excellent selectivity for hydrophilic biorelated molecules such as nucleobases and nucleosides.

Low-molecular-weight sulfonated chitosan as template for anticoagulant nanoparticles.

PurposeIn this work, low-molecular-weight sulfoethyl chitosan (SECS) was used as a model template for the generation of silver core-shell nanoparticles with high potential as anticoagulants for medical applications.Materials and methodsSECS were synthesized by two reaction pathways, namely Michael addition and a nucleophilic substitution with sodium vinylsulfonate or sodium 2-bromoethanesulfonate (NaBES). Subsequently, these derivatives were used as reducing and capping agents for silver nanoparticles in a microwave-assisted reaction. The formed silver-chitosan core-shell particles were further surveyed in terms of their anticoagulant action by different coagulation assays focusing on the inhibition of either thrombin or cofactor Xa.ResultsIn-depth characterization revealed a sulfoalkylation of chitosan mainly on its sterically favored O6-position. Moreover, comparably high average degrees of substitution with sulfoethyl groups (DSSE) of up to 1.05 were realized in reactions with NaBES. The harsh reaction conditions led to significant chain degradation and consequently, SECS exhibits masses of <50 kDa. Throughout the following microwave reaction, stable nanoparticles were obtained only from highly substituted products because they provide a sufficient charge density that prevented particles from aggregation. High-resolution transmission electron microscopy images reveal that the silver core (diameter ~8 nm) is surrounded by a 1–2 nm thick SECS layer. These core-shell particles and the SECS itself exhibit an inhibiting activity, especially on cofactor Xa.ConclusionThis interesting model system enabled the investigation of structure–property correlations in the course of nanoparticle formation and anticoagulant activity of SECS and may lead to completely new anticoagulants on the basis of chitosan-capped nanoparticles.

Sodium Persulfate and Potassium Permanganate Inhibit Methanogens and Methanogenesis in Stored Liquid Dairy Manure.

Stored liquid dairy manure is a hotspot for methane (CH) emission, thus effective mitigation strategies are required. We assessed sodium persulfate (NaSO), potassium permanganate (KMnO), and sodium hypochlorite (NaOCl) for impacts on the abundance of microbial communities and CH production in liquid dairy manure. Liquid dairy manure treated with different rates (1, 3, 6, and 9 g or mL L slurry) of these chemicals or their combinations were incubated under anoxic conditions at 22.5 ± 1.3°C for 120 d. Untreated and sodium 2-bromoethanesulfonate (BES)-treated manures were included as negative and positive controls, respectively, whereas sulfuric acid (HSO)-treated manure was used as a reference. Quantitative real-time polymerase chain reaction was used to quantify the abundances of bacteria and methanogens on Days 0, 60, and 120. Headspace CH/CO ratios were used as a proxy to determine CH production. Unlike bacterial abundance, methanogen abundance and CH/CO ratios varied with treatments. Addition of 1 to 9 g L slurry of NaSO and KMnO reduced methanogen abundance (up to ∼28%) and peak CH/CO ratios (up to 92-fold). Except at the lowest rate, chemical combinations also reduced the abundance of methanogens (up to ∼17%) and CH/CO ratios (up to ninefold), although no impacts were observed when 3% NaOCl was used alone. With slurry acidification, the ratios reduced up to twofold, whereas methanogen abundance was unaffected. Results suggest that NaSO and KMnO may offer alternative options to reduce CH emission from stored liquid dairy manure, but this warrants further assessment at larger scales for environmental impacts and characteristics of the treated manure.

Sulfoethylated polyaminostyrene: Synthesis in a gel and selectivity of sorption of silver(I) and copper(II) ions

A procedure was developed for preparing a new chelating ampholytic polymer, poly[N-(2-sulfoethyl) aminostyrene], by synthesis in a gel via treatment of polyaminostyrene with sodium 2-bromoethanesulfonate. The procedure allows preparation of the polymer with the degree of substitution of up to 0.7. Sulfoethylated polyaminostyrene with the degree of modification of 0.5 selectively takes up silver(I) and copper(II) ions from multicomponent solutions.

Selective inhibition of methanogenic archaea in leach bed systems by sodium 2-bromoethanesulfonate

Abstract Lignocellulosic biomass is a feasible feedstock for biogas production through anaerobic digestion. Leaching, as part of a two-stage fermentation concept, is the most meaningful strategy to convert the substrate’s organic carbon compounds into volatile fatty acids (VFA) during acidification. Various chemicals have been investigated so far to enhance the process of acidification by selective inhibition of methanogens. Hardly any of them were evaluated for technical leach bed systems. In order to enhance the process of acidification the inhibitory effect of sodium 2-bromoethanesulfonate (BES) on the activity of methanogens was evaluated. An optimal inhibition concentration of 40 mM BES was found in lab-experiments and was verified in a pilot scale leach bed system, which was fed with urban lignocellulosic biomass. Overall, 2200 g/m 3 of acetic acid were achieved during the leaching process by a one-time addition of BES. As VFA concentration levels were observed to be constant, BES approved suitable.

Diagnosis of the acidification and recovery of anaerobic sequencing batch reactors

This study aims to investigate the diagnosis of acidification and efficient recovery of a laboratory-scale anaerobic sequencing batch reactor (ASBR) which treats synthetic glucose wastewater under mesophilic conditions (35°C). The diagnosis of the ASBR showed that acidification occurred on the seventh day after adding 20 mmol/L of sodium 2-bromoethanesulfonate into the reactor. A three-step recovery strategy was employed to recover the acidified reactor efficiently and to study its restoration process. Results indicated that the acidified ASBR can be revived in approximately 50 d. The specific methanogenic activities of the sludge, which were based on the substrate of acetate, propionate, and butyrate, were restored at 0.85, 0.67, and 0.51 (gCOD-CH4)/(gVSS∙d), respectively. The fluorescent observation images revealed large amounts of Methanosarcina-like and rod-shaped methanogens distributed in the sludge flocs after reactor restoration, thus ensuring that the fermentative, acidogenic, and methanogenic processes proceeded effectively in the anaerobic system.

Chemical properties of N-2-Sulfoethylchitosan with a medium degree of substitution

A method was developed for the preparation of N-2-sulfoethylchitosan (SECH) via synthesis in a gel with the use of the reaction of chitosan and sodium 2-bromoethanesulfonate. This method makes it possible to conduct a polymer-like transformation without any acid or base. The structures of the obtained polymers were confirmed via IR and 1H NMR spectroscopy. The study of the sorption of Ag+, Cu2+, Zn2+, Ni2+, Co2+, Cd2+, Pb2+, Mn2+, Mg2+, Ca2+, Sr2+, and Ba2+ ions that were crosslinked by SECH during their joint presence in an ammonia-acetate buffer solution showed high values of selectivity in relation to those of silver(I) and copper(II). The selectivity of the sorption of silver(I) ions with respect to copper(II) ions increased with an increase in the degree of substitution of SECH.

Simple synthesis and chelation capacity of N-(2-sulfoethyl)chitosan, a taurine derivative

This study presents a simple and effective synthesis method of N-(2-sulfoethyl)chitosan (NSE-chitosan) via a reaction between sodium 2-bromoethanesulfonate and chitosan that allows polymer transformation without using additional reagents and organic solvents. The chemical structure of the obtained NSE-chitosan was characterized by FT-IR and 1H NMR spectroscopies. Thermogravimetric study of NSE-chitosan coupled with FT-IR analysis has shown stability of the polymer up to 200°C, which almost does not change with the increase of degree of substitution (DS). The sorption of transition and alkaline earth metal ions from multicomponent solutions on NSE-chitosan was investigated. The synthesized sorbents showed the selective recovery of silver(I) and copper(II) ions from ammonium acetate buffer solution. The increase of DS enhanced the selectivity to silver(I) ions sorption in comparison with copper(II) ions. Selectivity coefficients KAg/Cu increase from 1.3 to 10.9 with DS increasing up to 0.7 (ammonium acetate buffer solution, pH 6.5). Sorption isotherms of transition metal ions on NSE-chitosan with DS=0.5 have been fitted using Langmuir, Freundlich, and Redlich–Peterson models. The maximum sorption capacities of sorbent in ammonium acetate buffer solution at pH 6.0 were 1.72mmol/g for Cu(II), 1.23mmol/g for Ag(I) and below 0.5mmol/g for Co(II), Zn(II), Cd(II), Pb(II), Mn(II) and Ni(II) ions.

Enhancing volatile fatty acid (VFA) and bio-methane production from lawn grass with pretreatment.

The bioconversion of fiber-based carbohydrates during anaerobic digestion (AD) is impeded due to the recalcitrant nature of the plant cell wall. Pretreatment of lignocellulose materials under mild conditions are needed to improve the digestibility at minimum cost. This study investigated the effects of different pretreatments, including ozone, soaking aqueous ammonia (SAA), combined ozone and SAA (OSAA), and size reduction to enhance volatile fatty acid (VFA) and bio-methane production when lawn grass was used as substrate. To study VFA production, methanogenesis was selectively inhibited by sodium 2-bromoethanesulfonate to decouple the relation between VFA and bio-methane. The enzymatic hydrolysis of SAA (residence time 24h at 50°C) and OSAA (10 min ozonation and 6h of SAA) in pretreatment of lawn grass sample resulted in 86.71% and 89.63% sugar recovery, respectively. The specific methane yields of the control, ozone, SAA, OSAA, and size-reduced grass samples were 402.5, 358.8, 481.0, 462.6, and 358.3 ml CH4/g volatile solid (VS), respectively.

A comparison of treatment techniques to enhance fermentative hydrogen production from piggery anaerobic digested residues

To accelerate the start-up process and enhance the efficiency of a hydrogen production system, piggery anaerobic digested residues (PADRs) were subjected to several different treatment methods to enrich the hydrogen-producing bacteria. Eight treatment methods were performed on the PADRs, including acid, alkali, heat, drying, ultrasound, aeration, sodium 2-bromoethanesulfonate (BES), and chloroform. The best method was found to be drying at 60 °C for 48 h, which maximised the total biogas production and the hydrogen fraction without causing any methane production. The volatile fatty acids (VFAs) found after the drying treatment were acetate and butyrate, which together accounted for 91.9% of all VFAs, indicating that butyric acid fermentation was established. Due to the drying treatment, the metabolites produced from the biodegradable DOM were utilised more rapidly, more completely, and with the least amount of hard-degradation organic matter content obtained, according to EEM fluorescence spectra. This drying treatment offers a promising method to1 improve bio-hydrogen production.

Synthesis in a gel and sorption properties of N-2-sulfoethyl chitosan

A new procedure was developed for preparation of chelate amino-containing polymer N-2-sulfoethyl chitosan by synthesis in a gel through the reaction between chitosan and sodium 2-bromoethanesulfonate, yielding a polymer with the degree of substitution of up to 0.5. The structure of the resulting polymers was confirmed by 1H NMR spectroscopy. The sorption characteristics with respect to transition and alkaline-earth metal ions were determined for the cross-linked polymers.

Synthesis and characterization of novel cardo poly(aryl ether sulfone) bearing zwitterionic side groups for proton exchange membranes

A novel series of sulfonated poly(aryl ether sulfone)s with zwitterionic groups ([-CH 2CH 2CH 2N +CH 3(CH 2CH 2SO 3 −) 2]) have been prepared by the copolycondensation of a secondary amine-containing biphenol monomer with 4,4′-biphenol and 4,4′-dichlorodiphenylsulfone, and this was followed by the reaction with sodium 2-bromoethanesulfonate. All the resulting copolymers can form uniform and tough membranes by simple solution casting. The investigation of ion exchange capacity (IEC) values indicated that each ammonium group interacted with one sulfonate group. Because of strong intermolecular interaction, the increased packing density of chain formed that resulted in polymer membranes with lower water uptake and swelling ratio, and better oxidative stability compared with side-chain-type sulfonated poly(aryl ether sulfone)s with the close IEC values. The polymer membranes bearing zwitterionic groups kept intact in Fenton’s reagent at 80 °C for 20 h. Furthermore, these membranes demonstrated higher proton conductivity than the side-chain-type sulfonated polymer membranes at the same measurement conditions.

Competition of Fe(III) reduction and methanogenesis in an acidic fen

Peatlands are sources of relevant greenhouse gases such as CH4, but the temporal presence of Fe(III) may inhibit methanogenesis. Because excess of carbon during the vegetation period might allow concomitant electron-accepting processes, Fe(III) reduction and methanogenesis were studied during an annual season in an acidic fen. The upper peat layer displayed the highest Fe(II)- and CH4-forming activities. The rates of Fe(II) formation did not change during the year and methanogenesis started mostly when Fe(II) formation reached a plateau. Most of the Fe(III) pool seemed to be bioavailable, and addition of nitrilotriacetic acid stimulated only light Fe(II) formation, whereas EDTA and anthraquinone-2,6-disulfonate had no effect. In the presence of an inhibitor for methanogenesis (sodium 2-bromoethanesulfonate), Fe(II) formation was inhibited to 45%. Addition of Fe(III) during ongoing methanogenesis led only to a partial inhibition of CH4 formation. The proportion of acetoclastic methanogenesis varied between 42% and 90%, but no trend with time was observed. The number of acetate-, ethanol- or lactate-utilizing Fe(III) reducers approximated 10(5)-10(6) cells g (fresh wt peat)(-1). Fermentative glucose-utilizing Fe(III)-reducers were most abundant. Our results suggest that (1) methanogens used Fe(III) as an electron acceptor and (2) fermenting bacteria, which do not compete with methanogens for common electron donors, dominated the reduction of Fe(III) in this fen.

Syntheses of water-soluble N-donor ligands for aqueous catalysis using green, Michael-type addition reactions

A new route for synthesizing sulfonate-containing N-donor ligands has been developed involving the Michael-type addition reaction of primary or secondary amines with sodium vinylsulfonate in water. Our reactions offer several advantages over traditional Michael-type addition reactions. For example, while most conjugate addition reactions are carried out in organic solvents in the presence of bases or acids (S. G. Davies, T. D. McCarthy, Synlett, 1995, 700–704; D. Rosenthal, G. Braundrup, K. H. Davies, M.E. Wall, J. Org. Chem., 1965, 30, 3689–3696), our reactions adhere to green chemistry principles and are conducted in aqueous solutions without harsh bases or acids, eliminating the need for more toxic compounds and solvents. Additionally, the new synthetic route utilizes selective conjugate addition reactions instead of unselective alkylation reactions using sodium 2-bromoethanesulfonate or similar sulfonated alkyl halides (J. March, Advanced Organic Chemistry: reactions, mechanisms and structure, Wiley, New York, 4th edn., 1992, pp. 411-413), which greatly decreases the amount of undesired side-products. Finally, the new synthetic route yields new, water-soluble ligands which may be utilized in aqueous catalysis involving water-soluble metal complexes.

Polysulfone ionomers for proton-conducting fuel cell membranes: sulfoalkylated polysulfones

Polysulfones (PSUs) carrying short pendant alkyl side-chains with terminal sulfonic acid units have been prepared and studied as proton-conducting membrane materials. The first step in the preparation involved quenching of lithiated PSU with SO 2 gas, resulting in sulfinated PSU. In the second step, the lithium sulfinate units on the polymer were reacted with sodium 2-bromoethanesulfonate, sodium 3-bromopropanesulfonate, or 1,4-butane sultone to produce sulfoethylated, sulfopropylated, or sulfobutylated PSUs, respectively. Analysis by thermogravimetry showed that membranes based on the sulfoalkylated polymers were stable up to approximately 300 °C under N 2 atmosphere. Calorimetry measurements revealed that the modified polymers absorbed large amounts of non-freezing water, corresponding to 11–14 mol H 2O/mol SO 3H under immersed conditions. The proton conductivity of a membrane based on a PSU carrying 0.9 sulfopropyl chains per repeating unit was measured to be 77 mS/cm at 70 °C under humidifying conditions.

Pressure Effects on the Reaction of Hydroxide Ion with Sodium 2-Bromoethanesulfonate

Abstract Kinetic effect of pressure on the reaction of hydroxide ion with 2-bromoethanesulfonate was studied. The reaction was moderately accelerated by pressure and the activation volumes suggest that the presence of the negative charge on the sulfonato group does not produce any measurable solvation increase during activation.

2-Bromoethanesulfonate: A selective agent for isolating resistantMethanosarcina mutants

Sodium 2-bromoethanesulfonate (BES), a structural analog of 2-mercaptoethanesulfonate (coenzyme M), inhibited methanogenesis and growth ofMethanosarcina strain 227 in the presence of H2/CO2, methanol, or acetate. A single exposure to 24 μM BES was sufficient to produce cultures resistant to 240 μM BES. Wild-type cultures inhibited by 200 μM BES (or less) resumed growth and methane production when coenzyme M (coM) was added to the culture medium. Cultures incubated one week or longer with 200 μM BES (or less) spontaneously resumed growth and methanogenesis in the presence of H2/CO2, methanol, or acetate without added coM. BES resistance was heritable and not the result of inactivation or decomposition of BES. BES resistance acquired on one methanogenic substrate was retained when cells were grown on a different methanogenic substrate. However, BES resistance did not confer multiple resistance to other halomethane compounds such as chloroform, 2-bromoethanol, 2-bromopropionic acid, and chloramphenicol. BES resistance varied in two other genera of methanogens tested. One strain ofMethanospirillum hungatei was very sensitive to BES, and no resistant mutants were demonstrated. One strain ofMethanobacterium formicicum, however, was resistant to 200 μM BES without any known prior exposure to BES.