Betaine Surfactant Research Articles

Surface activity of a series of fluoroether betaine amphoteric surfactants: Oxygen roles

As PFOS, PFOA and their derivatives were banned according to the Stockholm Convention for their potential bioaccumulation and toxicity, people attempted to substitute the legacy fluorosurfactants with short-chain ones. Although short-chain alternatives can alleviate bioaccumulation, surface activity was compromised. Fluorine industry kept seeking for effective solution. In this work, we prepared and investigated a series of fluoroether betaine surfactants for their surface activity and spreading property. The role of oxygen on surface activity was discussed. We found that insertion of oxygen atoms into fluorinated chain could increase hydrophobicity and thus enhance surface activity. The contribution of one oxygen is approximately half of that of a difluoromethylene group by experience. Moreover, introducing oxygen diversified the structure to fill in the gap of surface activity between short and long fluorosurfactants. In summary, this work provided basic knowledge for molecular design.

Effects of Fatty Alcohols with Different Chain Lengths on the Performance of Low pH Biomass-Based Foams for Radioactive Decontamination.

Compared with polymers and nanoparticles, fatty alcohols can not only increase the stability of foam, but also maintain better foamability at pH < 2, which is beneficial to reduce waste liquid and increase decontamination efficiency for radioactive surface pollution. However, different fatty alcohols have different hydrophobic chain lengths. The effects of fatty alcohols with different chain lengths on the performance of decontamination foam were studied at pH < 2, to assist in the selection of suitable fatty alcohols as foam stabilizers. Combined with betaine surfactant and phytic acid, biomass-based foams were synthesized using fatty alcohols with different chain lengths. When the hydrophobic tail groups of the fatty alcohol and the surfactant were the same, the foam showed the best performance, including the lowest surface tension, the highest liquid film strength, the greatest sag-resistance and the best stability. However, when the hydrophobic tail groups were different, the space between adjacent surface active molecules was increased by thermal motion of the excess terminal tail segments (a tail-wagging effect), and the adsorption density reduced on the gas-liquid interface, leading to increased surface tension and decreased liquid film strength, sag-resistance and stability. The use of decontamination foam stabilized by fatty alcohols with the same hydrophobic group as the surfactant was found to increase the decontamination rate of radioactive uranium pollution from 64 to over 90% on a vertical surface.

Synergism between betaine surfactants under high-salt conditions

Foam properties and surface dilational rheology of single and mixed LHSB (lauramidopropyl hydroxyl sulfobetaine)-OAB (oleic amide propyl betaine) surfactants were measured to investigate the synergism between the two components. Experimental results showed obvious synergistic effects in foam stability, dilational modulus, and phase angle between LHSB and OAB. Moreover, interaction parameters were calculated to quantitatively characterize the synergism. The negative interaction parameters between LHSB and OAB demonstrated that there was an attractive interaction between LHSB and OAB, and the attractive interaction contributed to forming the dense surfactant layer at the liquid/air layer, which in turn improved foam stability. The negative values of parameters reached their maximum when the LHSB: OAB molar ratio ranged from 1:1 to 1:2, the same time the foam stability reached its maximum. The interaction between LHSB and OAB was confirmed by 2D NOSEY (two-dimensional nuclear overhauser enhancement spectroscopy) experiments, the interaction between LHSB and OAB could be attributed to the hydrogen bonding or the electrostatic interaction between the hydrophilic groups of the two surfactants.

The development of heat‐resistant and salt‐tolerant foam with betaine surfactants

AbstractA modified instrument was designed to evaluate foam properties under high temperature and pressure. The type and molar ratio of betaine surfactants were screened to develop the heat‐resistant and salt‐tolerant foam for Tahe oilfield (130°C, 220 g/L), and the effects of temperature and pressure on foam properties were also investigated. The synergism between surfactants and the enhanced oil recovery (EOR) mechanism of foam flooding in fractured‐vuggy reservoirs were studied. Experimental results showed the developed foam had excellent foaming ability and foam stability when the lauramidopropyl hydroxyl sulfobetaine (LHSB): erucic amide propyl betaine (EAB) molar ratio ranged from 1:1 to 1:2 (initial foam volume was 392 ml when the molar ratio was 1:1, drainage half‐time was 5.75 min and foam half‐time was 72 min when the molar ratio was 1:2 at 130°C and 2 MPa). The synergistic effect was found to reach its maximum when the LHSB:EAB molar ratio ranged from 1:1 to 1:2 according to interaction parameters, which agreed with the results of foam properties. Foam stability was found to considerably increase with increasing pressure, but decrease with increasing temperature. However, temperature and pressure were found to have consistent effects on foaming ability, that is, the foaming ability increased with increasing temperature and pressure. The flooding test showed foam flooding exhibited better sweep efficiency and higher recovery ratio in the fractured‐vuggy model than gas flooding and water flooding. This could be because injected foam did not channel through the top (or bottom) path due to its high viscosity and moderate density.

Micellar and sub-micellar chromatography with a cocamidopropyl betaine surfactant

We have coated a typical C18 column with the pH cationic charge controllable zwitterionic synthetic surfactant, cocamidopropyl betaine (CAPB), in order to generate a mixed mode reversed phase weak ion exchange column. As determined by the Thomas model, the column has an adsorbed surfactant capacity of 0.557 mmoles. The addition of 8.8 × 10–4 M CAPB to the totally aqueous mobile phase ensured stability of the surfactant on the column and permitted separation of the four component sulfonamide mixture with micellar liquid chromatography (MLC) in under 11 min. Comparatively, with a dilute H2SO4 mobile phase with no CAPB, the separation time for the sulfonamide mixture reached an excessive run time of an hour on the bare C18 chains. With CAPB in the mobile phase (no organic solvent present), a seven component sulfonamide mixture could be separated in less than 45 min. A five component short chain carboxylic acid mixture, separated in 20 min, was used to examine the ion exchange character of the column in pH environments of 2.3 and 4.6. Three phase MLC equilibrium analysis was also done in these pH environments with the sulfa drug and carboxylic acid mixtures to determine partition coefficients. Finally, a quite high molecular weight (70,000) anionic polystyrene sulfonate polymer was characterized by MLC with only CAPB and variable pH mobile phases; the optimal pH was determined to be 5.6. A totally aqueous mobile phase without CAPB was not suitable for profiling this polymer.

Effect of temperature on the stability of supercritical CO2 foam stabilized with a betaine surfactant at high pressure

Aiming at improving the thermal stability of CO2 foam under reservoir conditions, four different types of surfactants were evaluated through high temperature and pressure foaming apparatus. Supercritical CO2 (SC-CO2) foam stabilized with betaine surfactant EDSB has best stability among the surfactants. Effect of temperatures on CO2 foam properties were investigated and the stabilization mechanism of foam film was explored through molecular dynamics simulation. The results showed that the apparent viscosity in the capillary tube was up to 30 mPa·s at 15 s−1 at 120 ℃ and the resistance factor was up to 40 in the core. EDSB stabilized CO2 foam had lower C/W interfacial tension (IFT) due to the regular and tight molecular arrangement at the C/W interface. Covalence rate of CO2 foam stabilized with EDSB was lower than SDS at high temperature, which was attributed to large numbers of hydrophilic headgroups of EDSB molecule including sulfo groups, amino group and ethoxyl groups. They can bond more water molecules, forming thicker film than SDS. EDSB surfactant was also more difficult to be desorbed from the C/W interface than SDS, thereby further improving the foam film stability. The findings of this study can help for better understanding of the stabilization mechanism of CO2 foam film and optimizing the appropriate CO2 foam agents at high temperature.

Impact of oil and wettability on foam-assisted conformance control in a Middle Eastern carbonate reservoir

Gas injection has been evaluated and implemented in the large carbonate oil field located offshore Qatar as water alternating gas or WAG. It has been seen that WAG is economically viable and a robust enhanced oil recovery (EOR) method for homogenous formations. However, using WAG in heterogeneous parts of the field has not been attempted due to issues like early gas breakthrough and unfavourable sweep efficiency. Hence, it was decided to design a foam-assisted WAG system that can provide the required conformance control to mitigate those issues and expand the use of WAG. A complete laboratory programme was carried out to screen the best foaming surfactant formulation that resulted in the selection of environmentally friendly, Alkyl polyglucoside (APG) surfactant. Surfactant testing involved foamability in porous media under oil-wet and water-wet conditions in presence of residual oil to gas flood. The chosen surfactant showed good foam strength in both cases with effective mobility reduction factors (MRF) above 20. The impact of mobile oil was also observed by co-injecting oil during linear core flood experiments, which clearly showed that good foam strength could be achieved in a lower flow fraction of mobile oil with foam. Additionally, boosting of foam strength using amphoteric Lauryl Betaine (LB) surfactant was also performed. The formulation with APG/LB (70%/30%) gives foam boosting of 2.5 times compared to foam strength using APG alone. Additionally, it was shown that altering wettability using a nonionic Tergitol surfactant (TGT-1) as pre-flush and then injecting APG-5 surfactant and methane resulted in foam strength, which is 1.5 times higher than observed in oil-wet conditions.

The effect of betaine surfactants on the association behavior of associating polymer

The interfacial properties and rheological behavior of surfactant/polymer complex systems were measured to investigate the association behavior of the associating polymer. Compared with the pure surfactant solution, there are two inflection points in the surface tension curve for the surfactant/polymer complex systems. The two inflection points are dependent on the surfactant type and polymer concentration. The effect of surfactant on the rheological behavior of polymer can be divided into two aspects. First, the addition of short-chain betaine surfactant is detrimental to the viscosity of polymer solution due to the electrostatic shielding effect. Second, long-chain betaine surfactant also reduces the viscosity of polymer solutions at low concentrations. However, when the concentration of the long-chain betaine surfactant is relatively high, the long-chain betaine surfactant could form worm-like micelles that promote the intermolecular association and thus increase the number of associating junctions, thereby resulting in the augmentation of viscosity. So it is necessary to apply the long-chain betaine surfactant to build the polymer/surfactant flooding system. The interaction model between surfactant and polymer is proposed, which is different from the traditional ‘Three-Region Model’.

Investigation of the Kinetic Regularities of the Process of Biodegradation of Betaine Surfactant by Bacteria of the Genus Pseudomonas

Surfactants are extremely common organic compounds that enter the environment in large quantities in the form of household and industrial wastewater. The toxicity of surfactants for biological systems, the high concentration of substances and the duration of the bioremediation process of polluted ecosystems requires improving the biotechnology of microbial wastewater treatment for surfactants. The purpose of this work is to study the kinetic laws of the reaction of the biological decomposition of betaine surfactants. Pseudomonas bacteria were used as bio-destructors of the surfactants. Kinetic data were obtained to create the possibility of further optimization of research on the biodegradation of toxic organic substances. The strains that were promising destructors of cocamidopropylbetaine were selected. The toxicity of high concentrations of surfactants in relation to microorganisms of the genus Pseudomonas was proven. Safe values of the surfactant concentration for conducting biodegradation tests were found. A kinetic model of the biodestructive process was constructed. It proves that the processes of biodegradation are described by a kinetic equation of the first order. With the derived equation, it is possible to determine the time interval of biodegradation of cocamidopropylbetaine to the specified values by means of mathematical calculations.

Business Roundup

BUSINESS Business Roundup ShareShare onFacebookTwitterWechatLinked InRedditEmail C&EN, 2021, 99 (33), p 15September 13, 2021Cite this:C&EN 99, 33, 15AbstractSolid Power , a developer of batteries made with a solid electrolyte, plans to add a second facility in the Denver area that will make up to 30,000 metric tons per year of sulfide-based electrolyte material for its batteries. The firm says the facility will increase its output by a factor of 25 when it opens in 2022. Libra Specialty Chemicals is building a plant in Irlam, England, to make 1,000 metric tons per week of betaine surfactants. Libra says it has developed low-salt betaines that will be adopted by well-known makers of personal care and cleaning products. Kemira will build a third production line for alkenyl succinic anhydride sizing agents at its site in Nanjing, China, by 2023. The company says that demand for the papermaking ingredients is growing quickly and that supply has been tight. Mitsubishi Chemical will build a 2,000-metric-ton-per-year facility for sugar esters at its siteView: PDF | Full Text HTML

Optimum concentration of fly ash nanoparticles to stabilize CO2 foams for aquifer and soil remediation

Contamination caused by non-aqueous phase liquids (NAPLs) in aquifers and soil is an important challenge that requires effective remediation techniques. One potential approach is through the use of CO2 foams to displace NAPLs from permeable media. CO2 foams generated only by surfactants are not stable enough for the efficient removal of NAPLs contamination. This shortcoming may be alleviated via the use of nanoparticles (NPs)-surfactant mixtures as a stabilizing agent. This work focuses on the evaluation of the optimum concentration of fly ash nanoparticles for stabilizing CO2 foam with the combined action of the surfactant. The performance of this foam is evaluated in remediating a contaminated 41 mm × 36 mm surrogate permeable medium in a microfluidic device. Mixtures of fly ash, a by-product of coal-burning power plants, and alpha-olefin sulfonate (AOS) and lauramidopropyl betaine (LAPB) surfactants are used to generate stable foams. The results show that a 1000 mg/L AOS-LAPB surfactant solution along with 1000 mg/L of fly ash NPs produces the best performance. Formation of deposits in the matrix is observed. These deposits, which are more prominent at higher NP concentrations, appear to adversely affect displacement, displacement efficiency and remediation of the medium. This study demonstrates that using fly ash nanoparticles and optimizing their concentration can effectively stabilize CO2 foams and improve the displacement efficiency for aquifer and soil remediation.

Synthesis of nanorod apatites with templates at critical micelle concentrations and in vitro evaluation of cytotoxicity and antimicrobial activity

ABSTRACT This study aimed to investigate the synthesis, cytotoxicity, and antimicrobial activity of nanorod apatites obtained using different surfactants at their critical micelle concentrations via hydrothermal method. Nanoscale apatite was obtained from ionic solutions without a template (nHA) compared with synthesized nanorod apatites of T-nHA, S-nHA, F-nHA and P-nHA with four different templates, i.e. the cationic/cetyltrimethylammonium bromide (CTAB), anionic/sodium dodecyl sulfate (SDS), nonionic/Pluronic F-127, and zwitterionic/cocamidopropyl betaine (CAPB) surfactants. Results showed that all of the synthesized apatites have a nanoscale rod-shaped morphology with bacteriostatic properties on day 1. However, only the nanorod apatite of T-nHA demonstrated long-term antibacterial activity up to day 14 due to the combined nanoscale-sized effects and surface phenomena. Among the nanorod apatites produced by the surfactant molecular geometry and solution conditions, the synthesized nanorod apatite of P-nHA possessed the smallest homogeneous crystals. Cytotoxicity results revealed that the nanorod apatites of nHA and F-nHA present insignificant cytotoxicity. Given its acceptable bacteriostatic effect and biocompatibility, the F-nHA may be considered better than nHA. Compared with the conventional-sized apatites, surfactant template-assisted nanorod apatite of T-nHA with high antimicrobial activity may be used as composite grafts for reconstructive surgery to improve inflammation that may be caused by bacteria.

Salvaging Cochlear Implant After Suspected Biofilm Infection: Our Experience.

We describe a novel procedure using betaine surfactant and polyhexanide for biofilm in cochlear implants. Early intervention along with wound debridement, double layer vascularized flap and rifampicin helps in salvaging the implant. Leaving the array in cochlea avoids fibrosis and can be considered for cochlear implantation at a later stage. This novel procedure significantly limits morbidity and repeated surgeries.

Synthesis and Characterization of 2-Di-methyl Amino Ethyl Laurate Betaine Surfactant

Abstract The growing need for sustainable natural-based surfactants from green chemistry has led to syntheses of surfactants without the use of solvents and without the generation of by-products when milder manufacturing processes are used. The zwitterionic betaine ester surfactants are derived from natural renewable sources and are biodegradable. In this research, the betaine ester surfactant 2-di-methylaminoethyllaurate betaine was synthesized from 2-di-methylaminoehanol and lauric acid derived from coconut oil in a three-step chemo-enzymatic esterification reaction. The enzymatic process was optimized in terms of operating parameters such as temperature, time, molar ratio and enzyme concentration, resulting in a yield of 87.91%. Structural analysis of the intermediate 2-di-methylaminoethyl laurate as well as the final product 2-di-methylaminoethyl laurate betaine was carried out with FTIR and 1H NMR. The surfactant properties of the betaine were also determined and showed that the betaine can be used as a co-surfactant in many cosmetic and personal care products.

Effect of aromatic acid on the rheological behaviors and microstructural mechanism of wormlike micelles in betaine surfactant

The rheology and microstructural behaviors of viscoelastic surfactant solutions induced by different organic acids are fascinating. However, the viscosity and viscoelasticity behavior of some surfactants such as oleyl amidopropyl betaine (OAPB) surfactant is very poor even at high concentrations. To improve these properties at low concentrations, a system of OAPB and phthalic acid (OPA) at a mass ratio of 3:2 has been developed. The rheological behaviors and microstructural aggregations of the OAPB/OPA system were measured by rheometer, transmission electron microscopy (Cryo-TEM), and dynamic light scattering (DLS). The experimental results showed that the addition of OPA significantly increases the viscoelasticity and viscosity properties of the OAPB viscoelastic micelle solutions at 25°C. The improvements of these properties are attributed to the formation of a micellar network due to the addition of OPA. The rheology and micellar properties were found to transform a transparent viscous water like a fluid at pH 7 to a viscoelastic fluid at pH 2.9. The zero-shear viscosity and relaxation times declined exponentially with an increase of temperature indicating a reduction in the average micellar lengths. The properties changes were attributed to the strength of electrostatic attractions, hydrophobic effects, and hydrogen bonding between OAPB and OPA molecules. Since the current system can be easily tuned by pH for at least 3 circles without deterioration of its properties, the system unlocks the significant prospect for designing stimuli-responsive smart materials for various industrial applications.

Design and synthesis of an azobenzene–betaine surfactant for photo-rheological fluids

HypothesisMorphology of surfactant self-assemblies are governed by the intermolecular interactions and packing constraints of the constituent molecules. Therefore, rational design of surfactant structure should allow targeting of the specific self-assembly modes, such as wormlike micelles (WLMs). By inclusion of an appropriate photo-responsive functionality to a surfactant molecule, light-based control of formulation properties without the need for additives can be achieved. ExperimentsA novel azobenzene-containing surfactant was synthesised with the intention of producing photo-responsive wormlike micelles. Aggregation of the molecule in its cis and trans isomers, and its concomitant flow properties, were characterised using UV–vis spectroscopy, small-angle neutron scattering, and rheological measurements. Finally, the fluids capacity for mediating particle diffusion was assessed using dynamic light scattering. FindingsThe trans isomer of the novel azo-surfactant was found to form a viscoelastic WLM network, which transitioned to inviscid ellipsoidal aggregates upon photo-switching to the cis isomer. This was accompanied by changes in zero-shear viscosity up to 16,000×. UV–vis spectroscopic and rheo-SANS analysis revealed π-π interactions of the trans azobenzene chromophore within the micelles, influencing aggregate structure and contributing to micellar rigidity. Particles dispersed in a 1 wt% surfactant solution showed a fivefold increase in apparent diffusion coefficient after UV-irradiation of the mixture.

Synergistic effect of octadecyl ammonium oxide and oleate amide propyl betaine and development of a foam drainage reagent for natural gas production

Betaine surfactants are used widely in oil field chemistry as well as other industrial applications, but their foaming ability is very poor so that it cannot be used in foaming. In this work, the effect of octadecyl ammonium oxide on the foam properties of oleate amide propyl betaine, a new compound foaming reagent, is studied based on foam performance. Then, a foam drainage reagent of 0.5 wt% oleate amide propyl betaine and 0.1 wt% octadecyl ammonium oxide is developed for natural gas production. Its salt resistance, methanol resistance, high temperature resistance, anti-condensate oil performance, and emulsification ability are systematically evaluated. Furthermore, the factors affecting foam performance are analyzed. The results show that the compound foaming reagent has good anti-salt, anti-methanol, and anti-condensate oil properties for meeting application requirements. The microstructures of foams derived from different reagents reveal the stability mechanism. All results reflect the fact that compounding can expand their application range in different environments to various extents, which benefits the design and use of compound surfactants.

Improved As-Synthesized Oleic Amido Propyl Betaine Surfactant Mixture for Stable Ultra-Low Interfacial Tension: Effect of Mixed Co-Solvents

As-synthesized oleic amido propyl betaine surfactant mixture, that was produced through a “direct formulation through synthesis” process, exhibited ultra-low oil/water interfacial tension (IFT) values as low as 3.5 × 10−4 mN/m when dissolved in seawater at a reservoir temperature of 96 °C. The as-synthesized surfactant, which was left untreated, had a slightly cloudy appearance when mixed with seawater. Polar solvents were introduced to this surfactant to improve its aqueous solubility by changing its overall hydrophilicity, particularly on the oil/water interface. In this study, two types of glycol ether co-solvent, i.e., ethylene glycol monobutyl ether and diethylene glycol monobutyl ether, were used at different concentrations in a single application and as a mixture of co-solvents at a certain ratio. The behavior of the as-synthesized surfactant with the presence of these co-solvents was investigated. As a result, it showed that the co-solvent helps in solubility improvement and alters the interfacial tension behavior of the surfactant. Ethylene glycol monobutyl ether was found to be efficient in maintaining an ultra-low IFT value of the surfactant. However, the aqueous solubility of the surfactant was not significantly improved. In contrast, the addition of diethylene glycol monobutyl ether showed improvement of the aqueous solubility of the surfactant, but it tends to increase the IFT above ultra-low value. Based on this understanding, a set of co-solvent mixing ratios were tested, and the results showed further improvement in both the oil/water interfacial tension behavior and surfactant aqueous solubility. The most stable oil/water IFT of 3.36 × 10−3 mN/m and clearer surfactant solutions were obtained for ratio C at 35 wt.% presence of co-solvent.

Static and flow behaviors of supercritical CO2 foam stabilized with betaine surfactant for mobility control application

Aiming at improving the stability of Supercritical CO2 (SC-CO2) foam in high temperature and salinity reservoirs, a kind of betaine surfactant, Hexadecyl Hydroxypropyl Sulfo Betaine (HHSB), was screened to stabilize SC-CO2 foam. The properties of SC-CO2 foam were improved at elevated temperature and pressure. The effects of surfactant concentration, temperature, pressure and salinity on film drainage rate were measured to explore the stability of SC-CO2 foam. The results showed that an increase of surfactant concentration, pressure and salinity can decrease film drainage rate and enhance the foam stability, which was attributed to the increase of surfactant adsorption at the gas–liquid interface. The performance of SC-CO2 foam formed by HHSB was improved and the tolerant temperature was up to 100 °C. 1-D core flooding experiments indicated that compared with Coinjection of Surfactant and Gas (CSG) method the SC-CO2 foam generated through Surfactant-Alternative-Gas (SAG) method had lower foam strength but better in-depth migration capacity. The high temperature and pressure 3-D sand showed that in Water-Alternative-Gas (WAG) case CO2 broke early through the high permeability layers. In SAG case, SC-CO2 foam can improve the macroscopic sweep efficiency by reducing the CO2 mobility.

As-Synthesized Oleic Amido Propyl Betaine Surfactant Mixture and the Effect on the Crude Oil–Seawater Interfacial Tension

As-synthesized oleic amido propyl betaine surfactant mixture was developed through a slight modification of a conventional two-step betaine synthesis process of amidation and quaternization reactions. This method is a “direct formulating through synthesis” to achieve a targeted interfacial property (interfacial tension or IFT) of the as-synthesized surfactant. Oil–water IFT was measured in the crude oil–seawater system at 96 °C. The result showed that the as-synthesized surfactant was able to reduce crude oil–seawater IFT to the ultra-low level (&lt;0.01 mN/m). As the finding emerged, the investigation was conducted to identify the elements that would bring the characteristic of ultra-low IFT. The characterization of the surfactant using FTIR, TG-IR, and HPLC suggested that unreacted materials associated with the surfactant remained, such as the carryover of a fatty amide from the intermediate process, residues of N, N trimethylene dimethylamine and sodium chloride as a by-product, and the important newly formed sodium oleate compound that was inadvertently generated via the reaction. The performance of the as-synthesized in seawater condition has been verified and the surface tension plot shows the lowest surface tension point at 0.05 wt.% concentration before developing a plateau region at higher surfactant concentration, indicating that the formation of surfactant micelles has been interrupted by the presence of other components in the solution. The dynamic IFT test performed on the as-synthesized product revealed that it was still able to reduce the crude oil–seawater IFT to an ultra-low level, despite the multiple undesirable components in the surfactant. IFT as low as 3.4 × 10−4 mN/m for the specific seawater and crude oil composition was obtained at a temperature of 96 °C.