Nonionic Biosurfactants Research Articles

Effect of biosurfactants on the transport of polyethylene microplastics in saturated porous media

Microplastic (MP) pollution has become a significant global environmental issue, and the potential application of biosurfactants in soil remediation has attracted considerable attention. However, the effects of biosurfactants on the transport and environmental risks of MPs are not fully understood. This study investigated the transport of polyethylene (PE) in the presence of two types of biosurfactants: typical anionic biosurfactant (rhamnolipids) and non-ionic biosurfactant (sophorolipids) using column experiments. We explored the potential mechanisms involving PE surface roughness and the influence of dissolved organic matter (DOM) on PE transport in the column under the action of biosurfactants, utilizing the Wenzel equation and fluorescence analysis. The results revealed that both the concentration of biosurfactants and the surface roughness of PE were advantageous for the adhesion of biosurfactants to the PE surface, thereby enhancing the mobility of PE in the column. The proportion of hydrophobic substances in various DOM sources is a critical factor that enhances PE transport in the column. However, the biosurfactant-mediated enhancement of PE transport was inhibited by the biosurfactant-DOM mixture. This was mainly due to DOM occupying the adhesion sites of biosurfactants on PE surfaces. Moreover, the mobility of PE in the presence of sophorolipids is higher than that in the presence of rhamnolipids because the combined hydrophobic and electrostatic forces between PE and sophorolipids create synergistic effects that improve PE stability. Additionally, the mobility of PE increased with rising pH and decreasing ionic strength. These findings provide a more comprehensive understanding of MP transport when using biosurfactants for soil remediation.

Biosurfactants as foaming agents in calcium phosphate bone cements

The idea of using biosurfactants to obtain highly porous, foamed calcium phosphate cements (fCPCs) is novel. The popularity of these compounds is mainly attributed to their biological activity such as anticancer or antibacterial properties. In our study, it was investigated how the functionalization of cements, based on α-tricalcium phosphate (α-TCP), with non-ionic biosurfactants such as sucrose ester S0112 and saponin from Quillaja bark affected the physicochemical as well as biological properties of cement-type materials. Foaming with these selected surface active agents led to highly porous fCPCs (open porosity >60 vol%) with compressive strength values ranging from 0.2 to 3.3 MPa and did not influence negatively the bioactive potential of the cements. Results showed that the sucrose ester had a positive effect on all studied cell types (osteosarcoma cell line MG-63 and preosteoblasts MC3T3-E1), while the effect of the saponin differed depending on the origin of the cells (cancerous or non-cancerous). The obtained results shed new light on the use of biosurfactants as additives to CPCs and pave the way for further studies, especially in vivo.

Self-assembly and cleaning and wettability of a polysaccharide-surfactant system formed from the cationic hydroxypropyltrimethyl ammonium chloride chitosan and nonionic sucrose lauric acid ester

Contact lens care solution was prepared via hydroxypropyltrimethyl ammonium chloride chitosan (HACC) and sucrose lauric acid ester (SML) via self-assembly in borate buffer solution (BBS). The elution efficiency of lipids, micellization, and wettability properties of HACC-SML in BBS was studied systematically using high-performance liquid chromatography (HPLC), dynamic light scattering (DLS), zeta potential, surface tension, and contact angles methodologies. The elution efficiency of the lipid increased from 46.98% to 65.68%, whereas DLS and zeta potential data varied with the addition of SML. These caused the shrinkage of micelles, and the system became stable, and further revealed that SML was a non-ionic biosurfactant with excellent performance. The result of surface tension at water-air and contact angles on silicone hydrogel lens at 25 °C showed that SML has outstanding adsorption capacity with an increased degree of wetting, ensuring the comfort and safety of wearing.

Synthesis of a branched surfactant from the castor derivative and its surface properties

A new class of ricinoleic acid-derived branched surfactant with a Y-shaped structure (ethoxylated monohydroxy stearic acid methyl ester, 12-HMEEn) was synthesized and characterized by introducing a polyoxyethylene head group in the hydroxyl position inside the molecule. The physicochemical properties and surface activities of 12-HMEEn with different degrees of ethoxylation at various concentrations were studied. The typical Y-shaped structure of the molecule facilitates its adsorption at the interface, which provides an excellent surface activity and affects its surfactant properties significantly. The dynamic contact angle, wettability, foaming properties, and compatibility tests of 12-HMEEn showed that it has good wetting performance, low foaming and fast defoaming properties, and good compatibility in formulation applications, indicating that the surfactant has potential application in industrial cleaning.

Effects of Prednisolone Derivative and Panaxydol: Biosurfactants on Cell Wall Integrity of Acne-Causing Resistant Bacteria.

Acne is one of the most common dermatological skin problem caused due to inflammation of the skin, leading to unfavorable growth of Propionibacterium acnes. It is a slow growing anaerobic, gram-positive bacterium that releases chemotactic factors and leads to the complex pathogenicity of acne. There are several acne treatments/therapies available, but topical therapy is usually the first choice for mild to moderate acne, and as the severity of the acne increases, the treatment modalities fail. There are many acne treatment options available, but topical therapy is best suited for mild - to - moderate skin problems, and then as the seriousness of the acne grows, the therapeutic approaches fall short. Biosurfactants are surfactants produced from plants or animals; Saponins are plant derived non-ionic biosurfactants which have steroidal and triterpenic glycosides distributed largely in plant kingdom. Numerous studies conducted by scientists have established the antimicrobial activity of and are considered more advantageous over synthetic precursors as they are eco-friendly, cheap and non-toxic. The present study was undertaken to investigate the antibacterial activity of saponins (bio-surfactants) characterized using mass spectroscopy against acne-causing bacteria. The discharge of cellular components including protein and UV-sensitive materials in the cell-free supernatant was provoked by saponin, confirming the cellular and membrane disturbances.. Furthermore, various morphological changes on the bacterial cell surface structure by Transmission electron microscopy and scanning electron microscopy revealed the disruption of the cell integrity leading to death. Results confirmed presence of non-ionic surfactants primarily affecting the disruption and destruction to the bacteria which indicates that saponins are efficient components with great potential applications in various pharmaceutical preparations. Effects of Prednisolone derivative and Panaxydol: Biosurfactants on cell wall integrity of Acne-Causing Resistant Bacteria.

Surfactant-mediated thioglycosylation of 1-hydroxy sugars in water.

Thioglycosides are an important class of sugars, since they can be used as non-ionic biosurfactants, biomimetic glycosides, and building blocks for carbohydrate synthesis. Previously, Brønsted- or Lewis-acid-catalyzed dehydrative glycosylations between a 1-hydroxy sugar and a thiol have been reported to yield open-chain dithioacetal sugars as the major products instead of the desired thioglycosides. These dithioacetal sugars are by-products derived from the endocyclic bond cleavage of the thioglycosides. Herein, we report dehydrative glycosylation in water mediated by a Brønsted acid-surfactant combined catalyst (BASC). Glycosylations between 1-hydroxy furanosyl/pyranosyl sugars and primary, secondary, and tertiary aliphatic/aromatic thiols in the presence of dodecyl benzenesulfonic acid (DBSA) provided the thioglycoside products in moderate to good yields. Microwave irradiation led to improvements in the yields and a shortening of the reaction time. Remarkably, open-chain dithioacetal sugars were not detected in the DBSA-mediated glycosylations in water. This method is a simple, convenient, and rapid approach to produce a library of thioglycosides without the requirement of anhydrous conditions. Moreover, this work also provides an excellent example of complementary reactivity profiles of glycosylation in organic solvents and water.

A Straightforward Assay for Screening and Quantification of Biosurfactants in Microbial Culture Supernatants.

A large variety of microorganisms produces biosurfactants with the potential for a number of diverse industrial applications. To identify suitable wild-type or engineered production strains, efficient screening methods are needed, allowing for rapid and reliable quantification of biosurfactants in multiple cultures, preferably at high throughput. To this end, we have established a novel and sensitive assay for the quantification of biosurfactants based on the dye Victoria Pure Blue BO (VPBO). The assay allows the colorimetric assessment of biosurfactants directly in culture supernatants and does not require extraction or concentration procedures. Working ranges were determined for precise quantification of different rhamnolipid biosurfactants; titers in culture supernatants of recombinant Pseudomonas putida KT2440 calculated by this assay were confirmed to be the same ranges detected by independent high-performance liquid chromatography (HPLC)-charged aerosol detector (CAD) analyses. The assay was successfully applied for detection of chemically different anionic or non-ionic biosurfactants including mono- and di-rhamnolipids (glycolipids), mannosylerythritol lipids (MELs, glycolipids), 3-(3-hydroxyalkanoyloxy) alkanoic acids (fatty acid conjugates), serrawettin W1 (lipopeptide), and N-acyltyrosine (lipoamino acid). In summary, the VPBO assay offers a broad range of applications including the comparative evaluation of different cultivation conditions and high-throughput screening of biosurfactant-producing microbial strains.

Static adsorption of a new cationic biosurfactant on carbonate minerals: Application to EOR

One of the main challenges in the surfactant flooding process, used as a chemical based enhanced oil recovery (EOR) method, is the surfactant adsorption phenomenon. This paper highlights the adsorption equilibrium of Morus nigra leaf extract in aqueous solutions as a newly introduced cationic biosurfactant on carbonate minerals. A conductivity technique utilized to assess the adsorption of the surfactant in the aqueous phase. The adsorption data examined using four different equilibrium adsorption isotherm models (Langmuir, Freundlich, Temkin, and linear). The results confirm that the Langmuir isotherm model has the best match to experimental data with a coefficient of determination of 0.9960. Moreover, a comparison between the adsorption density of Morus nigra and Ziziphus Spina Christi (a nonionic biosurfactant) on two similar carbonate samples performed based on their adsorption mechanisms and pH values. The results of this paper can be useful in surfactant selection in EOR processes, especially for chemical flooding schemes.

Enzymatic glycolipid surfactant synthesis from renewables

Glycolipids are promising nonionic biosurfactants with a wide range of application. In contrast to the traditional surfactants from fossil origin, they are not only exhibiting excellent surfactant and emulsifying properties but are in addition biodegradable and non-toxic to the environment. Glycolipids can be produced by microbial fermentation, by chemical or enzymatical synthesis using renewable resources. In this review, strengths and weaknesses of each production method are compared and enzymatic synthesis is highlighted as the method of choice for the tailor-made synthesis of a wide range of novel glycolipids. As for enzymatical and chemical synthesis solvents with low water activity are needed to favor condensation instead of the hydrolysis reaction, organic solvents or ionic liquids are commonly used. However, the unusual deep eutectic solvent system might be a green alternative worth to consider. In terms of enzymatic catalysis, lipases are well known in literature and already widely used for the production of sugar-acyl-esters. However, β-glucosidases can be alternatively used for glycolipid synthesis which is far less studied. The abilities of both enzymes for glycolipid synthesis are therefore compared and discussed.

Performance evaluation of environmentally benign nonionic biosurfactant for enhanced oil recovery

Chemical enhanced oil recovery (EOR) is a successful method for increasing crude oil recovery. However, chemicals commonly used for enhanced oil recovery operations possess adverse biological impacts. To meet the legislative requirement and environmental protection demands, the performance of a highly biodegradable nonionic surfactant derived from tannic acid, a possible alternative, was evaluated using a microfluidic technology for the replacement of chemically synthesis surfactant by green chemistry products. Aqueous microdroplets containing the surfactant in crude oils were used for measurements of interfacial tension (IFT) reduction. The degree of interfacial tension reduction by sodium dodecyl sulfate (SDS), one of the most popular conventional surfactants, was also quantified for performance comparison. The potential of the biosurfactant for IFT reduction of light crude oil was superior to that of SDS. To evaluate the feasibility of the biosurfactant in improvement of recovery efficiency, surfactant-assisted flooding was tested under a random microfluidic network at the optimal concentrations, and the results were in good agreement with IFT reduction tests. The utilization of the polymer in a biosurfactant synthesis process effectively enhanced high sweep efficiency by decreasing a viscous fingering effect. The biosurfactant proved to be adequate and can sufficiently alleviate environmental concerns adopted by chemical flooding EOR.

Synthesis and characterization of novel alkoxy nonionic biosurfactants

ABSTRACTA series of novel alkoxy nonionic biosurfactants were synthesized by ring-opening reaction of methoxy poly(ethylene glycols) and alkylene oxide. The chemical structures of these biosurfactants were confirmed by Fourier-transform infrared spectroscopy (FTIR) and 1HNMR spectra. The surface tensions of these nonionic biosurfactants in the aqueous solutions were determined using a surface tensionmeter. The results showed that the critical micelle concentrations decreased with the increase of hydrophobic chain. However, due to the effect of intermolecular hydrogen bonding, the critical surface tensions of these nonionic biosurfactants increased with increasing the hydrophobic chain and were lower than those of conventional nonionic biosurfactants. Meanwhile, the effects of electrolytes on surface tension of these nonionic biosurfactants were slight. Due to the excellent surface activity, these alkoxy nonionic biosurfactants could have great potential in cleansing, oil recovery, and drug delivery.

Systematic investigation of the synergistic effects of novel biosurfactant ethoxylated phytosterol-alcohol systems on the interfacial tension of a water/model oil system

Increasing attention has been paid to the potential applications of biodegradable or natural surfactants in various fields, including chemical enhanced oil recovery (EOR), since the use of eco-friendly chemical processes was first proposed. The novel nonionic biosurfactant, ethoxylated phytosterols (BPS-n), was introduced to chemical EOR for the first time. The BPS-n showed a satisfactory ability to reduce the interfacial tension (IFT) between water and a model oil (n-octane) when the effects of BPS-n concentration, salinity and temperature were investigated. Several typical alcohols have been used as cosurfactants to further reduce the IFT through synergistic effects with BPS-30. Interestingly, there may be a close relationship between the ability to reduce the IFT and the hydrophobic chain length of the alcohol. Based on the adsorption and stereo-hindrance effect, we proposed a reasonable explanation for this relationship.

Green recyclable SO3H-carbon catalyst for the selective synthesis of isomannide-based fatty acid monoesters as non-ionic bio-surfactants

Solvent free one-pot synthesis of isomannide-based fatty acid monoesters as non-ionic bio-surfactants employing a green recyclable SO3H-carbon catalyst was demonstrated.

An efficient renewable-derived surfactant for aqueous esterification reactions

An efficient and simple approach for the aqueous esterification of a range of carboxylic acids with alcohols has been developed using catalytic amounts of a glucose-derived N-alkanoyl-N-methyl-1-glycamine non-ionic biosurfactant (C12MG). Excellent yields to final products were obtained under mild conditions and the protocol was amenable to both aromatic and long alkyl chain acids (e.g. fatty acids).

Regioselective acylation of methyl-α-d-glucopyranoside with different acylating agents catalysed by micro/mesoporous materials

The composite microporous/mesoporous material ZSM-5/MCM-48 was successfully prepared by hydrothermal synthesis using a simple one-step crystallization process. The material was a mesoporous composite containing zeolite and crystals of ZSM-5. The textural and structural features of this material were characterized by use of powder XRD, nitrogen sorption, FTIR spectroscopy, SEM, and TEM. The mesoporous material obtained, Al-MCM-48, and the composite material, ZSM-5/MCM-48, were used as catalysts for acylation of methyl-α-d-glucopyranoside. Fatty acids (n = 10, 14, and 16) and fatty acid chlorides were used, individually, as acylating agents for this reaction. The effects of solvent, type of catalyst, and nature of the fatty acids on the acylation reaction were investigated. Reaction yields in the range 50–70 % were achieved by use of this synthetic pathway. The products resulting from the acylation reaction are new nonionic bio-surfactants.

Lipase‐catalyzed synthesis of secondary glucose esters under continuous flow conditions

AbstractChemical methods for the synthesis of sugar esters require the use of high temperatures in the presence of alkaline catalysts resulting in undesirable by‐products and low regiosselectivity. Sugar‐based fatty acid esters are non‐ionic, biodegradable, odorless, non‐irritating, non‐toxic surfactants widely used pharmaceuticals, cosmetics, detergents, and food industry. Here in we report our results on enzymatic esterification of protected glucose (glucose ketal) with several fatty acids using the immobilized lipase from Rhizomucor miehei under batch and continuous flow conditions, to afford new glucose derivatives with potential surfactant properties. The results presented here shows that high conversions can be obtained in short reaction time.Practical application: The research of new non‐toxic, environmentally friendly and biodegradable surfactants to replace chemicals has increased along with the development of green chemistry. Nonionic biosurfactants, such as sugar fatty acid esters, may be obtained by enzymatic synthesis, a simple manufacturing method for application in several areas, including food, cosmetic, detergent, and pharmaceutical industry. In this work we have described the uncommon esterification of a steric hindered secondary hydroxyl group on glucose ketal leading to new glucose derivatives with potential application as surfactants.

ChemInform Abstract: Enzymatic Synthesis of Sugar Fatty Acid Esters in Ionic Liquids

AbstractReview: 40 refs.

Applicability Test of New Surfactant Produced from Zizyphus Spina-Christi Leaves for Enhanced Oil Recovery in Carbonate Reservoirs

After the primary production period, water flooding is usually performed to recover more oil from reservoirs. However, water flooding recoveries are low from naturally fractured carbonate reservoirs, due in part to these reservoirs being mixed to oil-wet. Most of Iranian reservoirs are naturally fractured. Chemical process and especially surfactant flooding is an interested method because of its effect on interfacial tension (IFT) reduction and wettability alteration. Different surfactants are used for chemical flooding in the world but these chemical have high price and some detrimental effect on the environment. In this paper a new nonionic biosurfactant which is produced from the leaves of special tree called Zizyphus Spina-Christi is introduced. There is a hypothesis that this surfactant can be used in chemical flooding of fractured reservoirs because of very low cost and availability in Middle-East and Africa compared to other currently used surfactants. For this purpose surfactant is extracted from the leaves by spray dryer method. The pendant drop method is used to measure interfacial tension and critical micelle concentration (CMC) values. In order to investigate the effect of this surfactant on oil recovery two series of imbibition experiments are conducted on water-wet and oil-wet samples. It is observed that oil recovery is about ∼16 % OOIP (original oil-in-place) for oil-wet cores by using this surfactant. In the same test, no oil is produced with water due to high oil wettability. After adding surfactant to the water, the oil recovery about ∼7 % OOIP is obtained. Other test is done on water-wet cores which shows that addition of surfactant reduce the ultimate recovery from ∼35 % OOIP to ∼12.5 % OOIP. Reducing interfacial tension cause decrease in imbibition drive mechanism and lower the ultimate recovery. These results indicate that this new type of surfactant can meet the technical requirements as enhanced oil recovery (EOR) agent for chemical flooding.

Enzymatic synthesis of sugar fatty acid esters in ionic liquids

Sugar fatty acid esters are nonionic biosurfactants widely used in food, cosmetic and pharmaceutical industries. Ionic liquids (ILs) have shown great potential as an alternative reaction medium to conventional organic solvents for their enzymatic synthesis, promoting a significant enhancement in sugar solubility, enzymatic reactivity and regioselectivity. In this perspective, we summarize the advances in the use of ILs as a solvent for sugar dissolution and lipase-catalyzed sugar ester synthesis, review the recent achievements in designing enzyme-compatible ILs for the synthesis, and discuss the challenges that the research on this topic is facing. Among the advanced ILs, deep eutectic solvents (DESs) merit a serious consideration as a potential reaction medium for this application.

Enzyme‐catalyzed regioselective synthesis of sucrose‐based esters

AbstractSucrose‐based esters are nonionic biosurfactants, which can be synthesized from the enzyme‐catalyzed esterification/transesterification of sucrose. The multi‐hydroxyl groups of sucrose and the immiscibility of sucrose with the acyl donors are the main bottlenecks in obtaining highly regioselective sucrose‐based esters. In this mini‐review, the effects of reaction conditions such as biocatalysts, design of solvent systems used as reaction media, modification and denaturation of substrates, and coupling with external auxiliary physical fields such as microwave irradiation and ultrasonic waves on the yield of sucrose esters and regioselectivity of products are highlighted. The existing problems in the field of enzymatic synthesis of sucrose esters as well as its future perspectives were pointed out. Copyright © 2011 Society of Chemical Industry