Biosurfactants are gaining attention due to their biobased nature, including reduced toxicity and enhanced biocompatibility. This research work investigates the characteristics of the biosurfactant extracted from the halophilic strain Pa84 of Pseudomonas aeruginosa and optimizes its production using a statistical model. The identity of biosurfactant from P. aeruginosa strain Pa84 as rhamnolipid was determined by comparing the genomic sequences of strain Pa84 with high-yielding strains of P. aeruginosa that produce rhamnolipid, through Fourier transform infrared and liquid chromatography-mass spectrometer analyses, and by the presence of rhlA, rhlB, and rhlC genes in the genome of strain Pa84 that are responsible for the production of rhamnolipid. A methodical strategy using a time-course assessment and statistical software optimized the production of rhamnolipids. After optimization using central composite design-response surface methodology, the medium composition of 3.34 g/L of NH4Cl, 1.03 g/L of NaCl, and 4 g/L of glycerol were chosen, yielding 7.48 ± 0.0217 g/L of biosurfactant. These findings will help in the development of effective and sustainable bioprocess that produce rhamnolipid biosurfactants, for use in a variety of sectors.
{"title":"Harmonizing rhamnolipid biosurfactant production by halophilic Pseudomonas aeruginosa Pa84 by applying response surface methodology","authors":"Priyanka Sharma, Shantam Gautam, Siddhi Joshi, Mousumi Debnath","doi":"10.1002/jsde.12825","DOIUrl":"10.1002/jsde.12825","url":null,"abstract":"<p>Biosurfactants are gaining attention due to their biobased nature, including reduced toxicity and enhanced biocompatibility. This research work investigates the characteristics of the biosurfactant extracted from the halophilic strain Pa84 of <i>Pseudomonas aeruginosa</i> and optimizes its production using a statistical model. The identity of biosurfactant from <i>P. aeruginosa</i> strain Pa84 as rhamnolipid was determined by comparing the genomic sequences of strain Pa84 with high-yielding strains of <i>P. aeruginosa</i> that produce rhamnolipid, through Fourier transform infrared and liquid chromatography-mass spectrometer analyses, and by the presence of <i>rhlA</i>, <i>rhlB</i>, and <i>rhlC</i> genes in the genome of strain Pa84 that are responsible for the production of rhamnolipid. A methodical strategy using a time-course assessment and statistical software optimized the production of rhamnolipids. After optimization using central composite design-response surface methodology, the medium composition of 3.34 g/L of NH<sub>4</sub>Cl, 1.03 g/L of NaCl, and 4 g/L of glycerol were chosen, yielding 7.48 ± 0.0217 g/L of biosurfactant. These findings will help in the development of effective and sustainable bioprocess that produce rhamnolipid biosurfactants, for use in a variety of sectors.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"599-612"},"PeriodicalIF":1.8,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939091","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Giuseppe Tartaro, Davide Schirone, Luigi Gentile, Gerardo Palazzo
The system made by water, isooctane and a blend of Sodium dioctyl sulfosuccinate (AOT) with its more hydrophilic homologue sodium dihexyl sulfosuccinate (SDHS) can give raise to Winsor I, III and II equilibria at room temperature by slight changes in salinity. The phase transitions have been tracked using diffusion NMR, and solubilized volume fractions while small-angle X-ray scattering (SAXS) provided insight into the characteristic lengths (ξ) within the microemulsions' structures. Our findings reveal a peculiar linear correlation between the reciprocal of these characteristic lengths (ξ−1) and the HLD values. For HLD <0, ξ−1 decreases linearly with HLD with a slope = −0.0056 Å−1 but just above HLD = 0 the slope reverses (+0.0056 Å−1) and ξ−1 increases linearly with HLD demonstrating that the HLD reflects the direction of interfacial curvature. However, at the optimal composition where the curvature is null and HLD = 0, the linear trends observed for ξ−1 below and above HLD = 0 converge at a ξ−1 value that is significantly greater than 0. This indicates that HLD is a measure of the interface/volume ratio and not of the interface curvature. This work aims to deepen the understanding of the relationship between the semi-empirical HLD equation and the spontaneous curvature of microemulsions.
{"title":"Microstructure of sulfosuccinates based microemulsions","authors":"Giuseppe Tartaro, Davide Schirone, Luigi Gentile, Gerardo Palazzo","doi":"10.1002/jsde.12828","DOIUrl":"10.1002/jsde.12828","url":null,"abstract":"<p>The system made by water, isooctane and a blend of Sodium dioctyl sulfosuccinate (AOT) with its more hydrophilic homologue sodium dihexyl sulfosuccinate (SDHS) can give raise to Winsor I, III and II equilibria at room temperature by slight changes in salinity. The phase transitions have been tracked using diffusion NMR, and solubilized volume fractions while small-angle X-ray scattering (SAXS) provided insight into the characteristic lengths (ξ) within the microemulsions' structures. Our findings reveal a peculiar linear correlation between the reciprocal of these characteristic lengths (ξ<sup>−1</sup>) and the HLD values. For HLD <0, ξ<sup>−1</sup> decreases linearly with HLD with a slope = −0.0056 Å<sup>−1</sup> but just above HLD = 0 the slope reverses (+0.0056 Å<sup>−1</sup>) and ξ<sup>−1</sup> increases linearly with HLD demonstrating that the HLD reflects the direction of interfacial curvature. However, at the optimal composition where the curvature is null and HLD = 0, the linear trends observed for ξ<sup>−1</sup> below and above HLD = 0 converge at a ξ<sup>−1</sup> value that is significantly greater than 0. This indicates that HLD is a measure of the interface/volume ratio and not of the interface curvature. This work aims to deepen the understanding of the relationship between the semi-empirical HLD equation and the spontaneous curvature of microemulsions.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"587-598"},"PeriodicalIF":1.8,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jsde.12828","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939336","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Biosurfactants prevent agglomeration of nanoparticles by reducing the surface tension and offer stability over time by forming a stable layer on the surface of nanoparticles. The current study focuses on the biosynthesis of silver nanoparticles (SNP) coated with a rhamnolipid biosurfactant (BS) and its use as an additive in fabric cleaning detergent. Rhamnolipids were extracted from a Pseudomonas aeruginosa strain, Pa84, that was isolated from a halophilic environment, Sambhar Salt Lake, Rajasthan, India. The reduction of silver ions was achieved by the rhamnolipid-coated SNP (BS-SNP). BS, SNP, and BS-SNP demonstrated antibacterial efficacy against a variety of microorganisms. Lipase, present in the crude biosurfactant, was immobilized on modified chitosan microbeads (Ch-BS-SNP) and used for washing fabrics. The conjugate was found to be effective as a laundry detergent additive. The immobilized lipase showed high relative activity ranging from 66% to 110% and performed better than free lipase or standards. Our results highlight a potential claim for a commercially viable laundry detergent additive.
{"title":"Biofabrication of rhamnolipid biosurfactant for nanoparticle stabilization and chitosan immobilized lipase: A green detergent additive","authors":"Priyanka Sharma, Mousumi Debnath","doi":"10.1002/jsde.12824","DOIUrl":"10.1002/jsde.12824","url":null,"abstract":"<p>Biosurfactants prevent agglomeration of nanoparticles by reducing the surface tension and offer stability over time by forming a stable layer on the surface of nanoparticles. The current study focuses on the biosynthesis of silver nanoparticles (SNP) coated with a rhamnolipid biosurfactant (BS) and its use as an additive in fabric cleaning detergent. Rhamnolipids were extracted from a <i>Pseudomonas aeruginosa</i> strain, Pa84, that was isolated from a halophilic environment, Sambhar Salt Lake, Rajasthan, India. The reduction of silver ions was achieved by the rhamnolipid-coated SNP (BS-SNP). BS, SNP, and BS-SNP demonstrated antibacterial efficacy against a variety of microorganisms. Lipase, present in the crude biosurfactant, was immobilized on modified chitosan microbeads (Ch-BS-SNP) and used for washing fabrics. The conjugate was found to be effective as a laundry detergent additive. The immobilized lipase showed high relative activity ranging from 66% to 110% and performed better than free lipase or standards. Our results highlight a potential claim for a commercially viable laundry detergent additive.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"571-585"},"PeriodicalIF":1.8,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143938985","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Rossannie Guasamucare, Emma Parente, Juan Carlos Pereira, Livia Arizaga
We report the synthesis of silver nanoparticles (Ag NPs) functionalized with L-cysteine (Ag-cys NPs) for colorimetric detection of contaminants: Hg2+, Pb2+, Cr6+ (CrO42−/Cr2O72), and As3+ in water samples. AgNPs synthesized were obtained in water from the mixture of the cationic and non-ionic surfactants, cetyltrimethylammonium bromide (CTAB) and nonylphenol ethoxylate (NP-10), respectively. Physicochemical characterization demonstrated a monomodal distribution of spherical nanoparticles with an average size of 8.25 nm. The stability of the Ag-cys NPs was evaluated by determining the surface charge, which was found to be +27.95 mV, indicating the stability of Ag-cys NPs against flocculation. The interaction between Ag-cys NPs and solutions of contaminants was studied. This was done by measuring the shift in LSPR band of Ag NPs covered with cys in the region of 400–450 nm. We observed a change or disappearance of color visually, indicating aggregation or oxidation of the Ag NPs. Concentration of cys, as well as the pH of the nanoparticles, were crucial in studying the aggregation process. This is a preliminary study in search of benefits such as low cost, in situ usability, ease of use, and rapid response making it a potential alternative to traditionally employed spectroscopic methods.
{"title":"Silver nanoparticle synthesis assisted by micelles for the development of a colorimetric nanobiosensor capable of detecting contaminants in water","authors":"Rossannie Guasamucare, Emma Parente, Juan Carlos Pereira, Livia Arizaga","doi":"10.1002/jsde.12821","DOIUrl":"10.1002/jsde.12821","url":null,"abstract":"<p>We report the synthesis of silver nanoparticles (Ag NPs) functionalized with L-cysteine (Ag-cys NPs) for colorimetric detection of contaminants: Hg<sup>2+</sup>, Pb<sup>2+</sup>, Cr<sup>6+</sup> (CrO<sub>4</sub><sup>2−</sup>/Cr<sub>2</sub>O<sub>7</sub><sup>2</sup>), and As<sup>3+</sup> in water samples. AgNPs synthesized were obtained in water from the mixture of the cationic and non-ionic surfactants, cetyltrimethylammonium bromide (CTAB) and nonylphenol ethoxylate (NP-10), respectively. Physicochemical characterization demonstrated a monomodal distribution of spherical nanoparticles with an average size of 8.25 nm. The stability of the Ag-cys NPs was evaluated by determining the surface charge, which was found to be +27.95 mV, indicating the stability of Ag-cys NPs against flocculation. The interaction between Ag-cys NPs and solutions of contaminants was studied. This was done by measuring the shift in LSPR band of Ag NPs covered with cys in the region of 400–450 nm. We observed a change or disappearance of color visually, indicating aggregation or oxidation of the Ag NPs. Concentration of cys, as well as the pH of the nanoparticles, were crucial in studying the aggregation process. This is a preliminary study in search of benefits such as low cost, in situ usability, ease of use, and rapid response making it a potential alternative to traditionally employed spectroscopic methods.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"557-569"},"PeriodicalIF":1.8,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143938984","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Mairis Guevara, Antonio Luis Cárdenas, Ana Forgiarini
Systems with elongated cylindrical micelles, also known as worm-like micelles (WM) or viscoelastic surfactants (VES), have high surface activity and high viscosity, which makes them attractive in different applications such as improved oil recovery, friction reducing agents in heating and cooling fluids, household and personal care products. This study examines the carbon's chain length of alkyl propoxylated sodium sulfate anionic surfactants (C16O(PO)15S, C14O(PO)15S, and C12O(PO)15S) mixed with a nonionic ethoxylated surfactant on viscoelastic properties and interfacial tension. Results show that the larger the surfactant's carbon chain, the greater the possibility of forming WM. Furthermore, the propylene oxides' (PO) number and the nonionic surfactant's type of tail (linear or branched) is studied, not only on WM formation but also on WM/crude interfacial tension values. It is observed that the surfactant's molecular structure plays an important role in WM formation. By increasing the anionic surfactant's PO from 15 to 20 units, the maximum value of zero viscosity goes from 4.507 to 0.092 Pa.s and by changing the structure of the nonionic surfactant from linear (C12-13EO8) to branched (C12-14EO9) keeping the PO number of the extended surfactant constant, the zero viscosity value goes from 4.507 to 0.28 Pa.s. Likewise, the WM/crude interfacial tension reached values of the order of 10−3 mN/m in the salinity range studied, which makes these systems very interesting for polymer substitution in enhanced crude oil recovery (EOR).
{"title":"Study of worm-like micelles of alcohol propoxylated sulfate/alcohol ethoxylated surfactants mixtures for crude oil recovery","authors":"Mairis Guevara, Antonio Luis Cárdenas, Ana Forgiarini","doi":"10.1002/jsde.12819","DOIUrl":"10.1002/jsde.12819","url":null,"abstract":"<p>Systems with elongated cylindrical micelles, also known as worm-like micelles (WM) or viscoelastic surfactants (VES), have high surface activity and high viscosity, which makes them attractive in different applications such as improved oil recovery, friction reducing agents in heating and cooling fluids, household and personal care products. This study examines the carbon's chain length of alkyl propoxylated sodium sulfate anionic surfactants (C<sub>16</sub>O(PO)<sub>15</sub>S, C<sub>14</sub>O(PO)<sub>15</sub>S, and C<sub>12</sub>O(PO)<sub>15</sub>S) mixed with a nonionic ethoxylated surfactant on viscoelastic properties and interfacial tension. Results show that the larger the surfactant's carbon chain, the greater the possibility of forming WM. Furthermore, the propylene oxides' (PO) number and the nonionic surfactant's type of tail (linear or branched) is studied, not only on WM formation but also on WM/crude interfacial tension values. It is observed that the surfactant's molecular structure plays an important role in WM formation. By increasing the anionic surfactant's PO from 15 to 20 units, the maximum value of zero viscosity goes from 4.507 to 0.092 Pa.s and by changing the structure of the nonionic surfactant from linear (C<sub>12-13</sub>EO<sub>8</sub>) to branched (C<sub>12-14</sub>EO<sub>9</sub>) keeping the PO number of the extended surfactant constant, the zero viscosity value goes from 4.507 to 0.28 Pa.s. Likewise, the WM/crude interfacial tension reached values of the order of 10<sup>−3</sup> mN/m in the salinity range studied, which makes these systems very interesting for polymer substitution in enhanced crude oil recovery (EOR).</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"523-533"},"PeriodicalIF":1.8,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939049","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The surface activities and application properties of aqueous solution surfactants are greatly influenced by their structure, especially the spacer group that connects the polar head groups. Herein, four new non-ionic Gemini surfactants with different spacers were designed and synthesized, and their surfactant properties and biodegradability were studied. The synthesis of these compounds involves a two-step procedure. The first step is the formation of an amide from lauric acid and diethanolamine. The second step is the reaction of lauryl diethanolamide with four different spacers, the latter being flexible-hydrophilic, and rigid-hydrophobic in structure, respectively. Their structures were characterized using 1H NMR, 13C NMR, FT-IR, and ESI-MS. The critical micelle concentration (CMC), the surface tension at CMC (γCMC), the efficiency of these compounds to reduce the surface tension by 20 mN/m (C20 and pC20), the effectiveness (πCMC), the maximum surface excess (Γmax), and the minimum surface area (Amin) were measured at 20, 40, and 50°C. The molecular architecture of the spacers in these compounds strongly influences the thermodynamic parameters, such as the standard change for Gibbs free energy of adsorption (ΔG°ads) and the standard change for Gibbs free energy of micellization (ΔG°mic). The ability of these surfactants to reduce surface tension is particularly good, but their distinguishing characteristic is their high relative propensity to form micellar aggregates. This aggregation ability improves as the hydrophilicity and flexibility of the spacer increase. Finally, in less than 30 days, all non-ionic Gemini surfactants were determined to be 99% biodegradable in river water.
{"title":"Synthesis, characterization, biodegradation, and evaluation of the surface-active properties of non-ionic gemini surfactants derived from lauryl diethanolamide","authors":"Gerónimo Tognotti, Carolina Guadalupe Gutierrez, Marcelo César Murguía","doi":"10.1002/jsde.12820","DOIUrl":"10.1002/jsde.12820","url":null,"abstract":"<p>The surface activities and application properties of aqueous solution surfactants are greatly influenced by their structure, especially the spacer group that connects the polar head groups. Herein, four new non-ionic Gemini surfactants with different spacers were designed and synthesized, and their surfactant properties and biodegradability were studied. The synthesis of these compounds involves a two-step procedure. The first step is the formation of an amide from lauric acid and diethanolamine. The second step is the reaction of lauryl diethanolamide with four different spacers, the latter being flexible-hydrophilic, and rigid-hydrophobic in structure, respectively. Their structures were characterized using <sup>1</sup>H NMR, <sup>13</sup>C NMR, FT-IR, and ESI-MS. The critical micelle concentration (CMC), the surface tension at CMC (γ<sub>CMC</sub>), the efficiency of these compounds to reduce the surface tension by 20 mN/m (<i>C</i><sub>20</sub> and p<i>C</i><sub>20</sub>), the effectiveness (π<sub>CMC</sub>), the maximum surface excess (Γ<sub>max</sub>), and the minimum surface area (<i>A</i><sub>min</sub>) were measured at 20, 40, and 50°C. The molecular architecture of the spacers in these compounds strongly influences the thermodynamic parameters, such as the standard change for Gibbs free energy of adsorption (Δ<i>G°</i><sub><i>ads</i></sub>) and the standard change for Gibbs free energy of micellization (Δ<i>G°</i><sub><i>mic</i></sub>). The ability of these surfactants to reduce surface tension is particularly good, but their distinguishing characteristic is their high relative propensity to form micellar aggregates. This aggregation ability improves as the hydrophilicity and flexibility of the spacer increase. Finally, in less than 30 days, all non-ionic Gemini surfactants were determined to be 99% biodegradable in river water.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"535-556"},"PeriodicalIF":1.8,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939050","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The wide use of antibiotics can lead to antimicrobial resistance. Biosurfactant rhamnolipids are not prone to induce antimicrobial resistance due to their potential to target microbial membranes in both bacteria and fungi. However, the membrane interaction of anionic rhamnolipids with microbials has never been visually observed. This study applied previously synthesized anionic fluorescent Trisodium 8-hydroxypyrene-1,3,6-trisulfonate (HPTS)-based surfactants, with hydrophobic tails from C8 to C18, to examine their interaction with the plant pathogen Alternaria alternata. The antifungal potency of the surfactants exhibited a positive correlation with the increase in hydrophobic chain length, culminating in C16, which demonstrated the highest activity. Subsequently, a modest reduction in potency was noted for the C18. Fluorescence microscopy confirmed the membrane targeting of HPTS-C16, and molecular dynamics simulations supported its specific membrane interaction. HPTS-C16 was notably more effective against spores than mycelium, consistent with its binding affinity. This research provides a fluorescent method to dissect the relationship between surfactant properties and microbial membrane characteristics, guiding the development of antimicrobials to combat resistance.
{"title":"Interpretation of antimicrobial function of biosurfactant rhamnolipids using Trisodium 8-hydroxypyrene-1,3,6-trisulfonate-based fluorescent surfactants","authors":"Shuai Kong, Haifeng Xiao, Baima Zhuoga, Chong Shen, Qin Meng","doi":"10.1002/jsde.12804","DOIUrl":"10.1002/jsde.12804","url":null,"abstract":"<p>The wide use of antibiotics can lead to antimicrobial resistance. Biosurfactant rhamnolipids are not prone to induce antimicrobial resistance due to their potential to target microbial membranes in both bacteria and fungi. However, the membrane interaction of anionic rhamnolipids with microbials has never been visually observed. This study applied previously synthesized anionic fluorescent Trisodium 8-hydroxypyrene-1,3,6-trisulfonate (HPTS)-based surfactants, with hydrophobic tails from C8 to C18, to examine their interaction with the plant pathogen <i>Alternaria alternata</i>. The antifungal potency of the surfactants exhibited a positive correlation with the increase in hydrophobic chain length, culminating in C16, which demonstrated the highest activity. Subsequently, a modest reduction in potency was noted for the C18. Fluorescence microscopy confirmed the membrane targeting of HPTS-C16, and molecular dynamics simulations supported its specific membrane interaction. HPTS-C16 was notably more effective against spores than mycelium, consistent with its binding affinity. This research provides a fluorescent method to dissect the relationship between surfactant properties and microbial membrane characteristics, guiding the development of antimicrobials to combat resistance.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"511-522"},"PeriodicalIF":1.8,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939646","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
N-lauroyl derivatives of amino acids have widely been reported as environmentally benign surfactants. Although N-lauroyl-l-glutamate is reported in the literature, the effect of the two carboxylate groups in it has not been specifically addressed. In this study, we report the interactions of bovine serum albumin (BSA) with N-lauroylglutamate (S1) and an N-lauroyl derivative of a tripeptide of glutamic acid (S2), respectively. The surfactant S1 has two and S2 has four carboxylic acid groups making them different from other N-lauroyl amino acids, which have just one carboxylic acid group. The aim of this study is to understand the role of the number of carboxylate groups present in these amino acid-based anionic surfactants while interacting with biomolecules such as BSA. The critical micelle concentration (CMC) of the surfactants were measured both in the presence and absence of BSA using fluorescence spectroscopy. The fluorescence of BSA was quenched on addition of the surfactants. The mechanisms of fluorescence quenching were established by studying the fluorescence at three different temperatures. CD studies were performed to calculate the temperature at which BSA unfolds completely in the presence and absence of the surfactants. Conformational changes in the secondary structure of BSA were also observed on the addition of S1 and S2. The results of these studies are compared with those previously reported for the interactions between BSA and N-lauroylglycinate. We find that S1 has a lower CMC than S2 and lauroylglycinate. The surfactant S1 stabilized the secondary structure of BSA better at higher temperatures.
{"title":"N-lauroylglutamates with two and four carboxylate head groups: Their interactions with bovine serum albumin","authors":"Ankita Singh, Sumedha Gupta, Neelakshi, Vinithra Gurunarayanan, Ramesh Ramapanicker","doi":"10.1002/jsde.12818","DOIUrl":"10.1002/jsde.12818","url":null,"abstract":"<p><i>N</i>-lauroyl derivatives of amino acids have widely been reported as environmentally benign surfactants. Although <i>N</i>-lauroyl-<span>l</span>-glutamate is reported in the literature, the effect of the two carboxylate groups in it has not been specifically addressed. In this study, we report the interactions of bovine serum albumin (BSA) with <i>N</i>-lauroylglutamate (<b>S1</b>) and an <i>N</i>-lauroyl derivative of a tripeptide of glutamic acid (<b>S2</b>), respectively. The surfactant <b>S1</b> has two and <b>S2</b> has four carboxylic acid groups making them different from other <i>N</i>-lauroyl amino acids, which have just one carboxylic acid group. The aim of this study is to understand the role of the number of carboxylate groups present in these amino acid-based anionic surfactants while interacting with biomolecules such as BSA. The critical micelle concentration (CMC) of the surfactants were measured both in the presence and absence of BSA using fluorescence spectroscopy. The fluorescence of BSA was quenched on addition of the surfactants. The mechanisms of fluorescence quenching were established by studying the fluorescence at three different temperatures. CD studies were performed to calculate the temperature at which BSA unfolds completely in the presence and absence of the surfactants. Conformational changes in the secondary structure of BSA were also observed on the addition of <b>S1</b> and <b>S2</b>. The results of these studies are compared with those previously reported for the interactions between BSA and <i>N</i>-lauroylglycinate. We find that <b>S1</b> has a lower CMC than <b>S2</b> and lauroylglycinate. The surfactant <b>S1</b> stabilized the secondary structure of BSA better at higher temperatures.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"501-510"},"PeriodicalIF":1.8,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939254","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Jiadong Chen, Weikang Tang, Mengqi Han, Qinfei Chen, Hong Zhou, Yongkui Zhang, Wenbin Liu
Amino acid surfactants are widely used in areas of life and industry. Biomimetic synthesis of a new type of amino acid surfactant was based on the melanogenesis using the natural substances ethyl protocatechuate. Ethyl protocatechuate was oxidized to o-benzoquinone using silver oxide. The amino group of amino acids, including arginine, cysteine, glutamic acid, histidine, leucine, and threonine, was conjugated with o-benzoquinone to synthesize melanin-like amino acid surfactants. o-Benzoquinone moiety behaved as hydrophobic part while amino acid residue served as hydrophilic head group. The critical micelle concentration of cysteine product was 1.18 mM. The melanin-like amino acid surfactant showed excellent foamability, wettability, emulsification, solubilization, and dispersibility properties. Arginine product showed the longest foam half lifetime of 18 min; the wetting time of threonine product was 23 s; the emulsion delamination time of cysteine product was 1034 and 1940 s for liquid paraffin and soybean oil, respectively; threonine product had the most solubilization capacity of 9430 mL mol−1 of benzene; glutamic acid product showed the highest lime soap dispersing power value of 45.58%. It was the first invention for biomimetic synthesis of amino acid surfactant from aspect of both structure and route. Melanin-like amino acid surfactant had promising potential in both fundamental research and industrial application.
氨基酸表面活性剂广泛应用于生活和工业领域。以天然物质原儿茶酸乙酯为原料,以黑素生成为基础,仿生合成了一种新型氨基酸表面活性剂。用氧化银将原儿茶酸乙酯氧化为邻苯醌。将精氨酸、半胱氨酸、谷氨酸、组氨酸、亮氨酸、苏氨酸等氨基酸的氨基与邻苯醌偶联,合成类黑色素氨基酸表面活性剂。邻苯醌部分为疏水部分,氨基酸残基为亲水头基。半胱氨酸产物的临界胶束浓度为1.18 mM。该类黑色素氨基酸表面活性剂具有优异的起泡性、润湿性、乳化性、增溶性和分散性。精氨酸产物泡沫半衰期最长,为18 min;苏氨酸产物润湿时间为23 s;液体石蜡和大豆油的半胱氨酸产物乳化分层时间分别为1034 s和1940 s;苏氨酸产物对苯的增溶量最大,为9430 mL mol−1;谷氨酸产品的石灰皂分散力值最高,为45.58%。无论从结构还是从途径上都是仿生合成氨基酸表面活性剂的第一个发明。类黑色素氨基酸表面活性剂具有广阔的基础研究和工业应用前景。
{"title":"Synthesis of amino acid surfactants bioinspired from melanin using ethyl protocatechuate","authors":"Jiadong Chen, Weikang Tang, Mengqi Han, Qinfei Chen, Hong Zhou, Yongkui Zhang, Wenbin Liu","doi":"10.1002/jsde.12815","DOIUrl":"10.1002/jsde.12815","url":null,"abstract":"<p>Amino acid surfactants are widely used in areas of life and industry. Biomimetic synthesis of a new type of amino acid surfactant was based on the melanogenesis using the natural substances ethyl protocatechuate. Ethyl protocatechuate was oxidized to o-benzoquinone using silver oxide. The amino group of amino acids, including arginine, cysteine, glutamic acid, histidine, leucine, and threonine, was conjugated with o-benzoquinone to synthesize melanin-like amino acid surfactants. o-Benzoquinone moiety behaved as hydrophobic part while amino acid residue served as hydrophilic head group. The critical micelle concentration of cysteine product was 1.18 mM. The melanin-like amino acid surfactant showed excellent foamability, wettability, emulsification, solubilization, and dispersibility properties. Arginine product showed the longest foam half lifetime of 18 min; the wetting time of threonine product was 23 s; the emulsion delamination time of cysteine product was 1034 and 1940 s for liquid paraffin and soybean oil, respectively; threonine product had the most solubilization capacity of 9430 mL mol<sup>−1</sup> of benzene; glutamic acid product showed the highest lime soap dispersing power value of 45.58%. It was the first invention for biomimetic synthesis of amino acid surfactant from aspect of both structure and route. Melanin-like amino acid surfactant had promising potential in both fundamental research and industrial application.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"491-500"},"PeriodicalIF":1.8,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Surfactant plays a crucial role in the chemical enhanced oil recovery (cEOR) process, and in-situ emulsification is regarded as one of the mechanisms for surfactant flooding. However, no direct evidences are available so far to show how emulsions are generated in porous media, and how emulsification is essential for cEOR. To address these issues, binary mixtures of several currently-used sulfonate surfactants, SH5, SH6, and SHZ, were formulated with connate brine to displace crude oil in both 2D microfluidic chips and 3D glass beads porous media, as well as artificial cores. It was found that both “oil-in-water” (O/W) and “water-in-oil” (W/O) macroemulsions can be formed in-situ inside the porous media, and they improve oil recovery mainly through breaking residual oil into small drops and improving mobility ratio, which can significantly reduce the residual oil saturation by up to 12.8% in 2D microchips. The in-situ emulsification in 3D glass beads medium can get oil recovery factor up to 15% over water flooding. In-situ formulation of microemulsion was also observed in microfluidic flow tests. Part of the oil phase is emulsified into microemulsions that are present in the middle phase, further mobilizing the oil trapped downstream, lowering residual oil saturation from 54.8% to 11.3% in 2D microchips, and enhancing oil recovery factor up to 25% in core flooding test. These findings advance insightful understanding of in-situ emulsification during surfactant flooding process under simulated oil reservoir condition, offering real-time evidence of how both macro- and micro-emulsions formation help for cEOR.
{"title":"Microfluidic visualization of in-situ emulsification during surfactant flooding","authors":"Yiwei Fang, Moyi Li, Baoliang Peng, Weidong Liu, Guangzhi Liao, Xuezhi Zhao, Yujun Feng","doi":"10.1002/jsde.12816","DOIUrl":"10.1002/jsde.12816","url":null,"abstract":"<p>Surfactant plays a crucial role in the chemical enhanced oil recovery (cEOR) process, and in-situ emulsification is regarded as one of the mechanisms for surfactant flooding. However, no direct evidences are available so far to show how emulsions are generated in porous media, and how emulsification is essential for cEOR. To address these issues, binary mixtures of several currently-used sulfonate surfactants, S<sub>H5</sub>, S<sub>H6</sub>, and S<sub>HZ</sub>, were formulated with connate brine to displace crude oil in both 2D microfluidic chips and 3D glass beads porous media, as well as artificial cores. It was found that both “oil-in-water” (O/W) and “water-in-oil” (W/O) macroemulsions can be formed in-situ inside the porous media, and they improve oil recovery mainly through breaking residual oil into small drops and improving mobility ratio, which can significantly reduce the residual oil saturation by up to 12.8% in 2D microchips. The in-situ emulsification in 3D glass beads medium can get oil recovery factor up to 15% over water flooding. In-situ formulation of microemulsion was also observed in microfluidic flow tests. Part of the oil phase is emulsified into microemulsions that are present in the middle phase, further mobilizing the oil trapped downstream, lowering residual oil saturation from 54.8% to 11.3% in 2D microchips, and enhancing oil recovery factor up to 25% in core flooding test. These findings advance insightful understanding of in-situ emulsification during surfactant flooding process under simulated oil reservoir condition, offering real-time evidence of how both macro- and micro-emulsions formation help for cEOR.</p>","PeriodicalId":17083,"journal":{"name":"Journal of Surfactants and Detergents","volume":"28 3","pages":"479-490"},"PeriodicalIF":1.8,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143939632","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}