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JOURNAL OF SURFACTANTS AND DETERGENTS · 2025 · IF 1.8

Development of green solubilizer based on acidic sophorolipid

Bochuan Lin,Jing Wang,Jiansheng Zha,Kuan Chang

Solubilization of oil-soluble substances in aqueous solution is essential in daily chemistry. Commonly used synthetic solubilizers are environmentally harmful and have limited applications. In this study, sophorolipid, a biosurfactant, was purified through an efficient, simple, and solubilization-compatible method, yielding an aqueous acidic sophorolipid (acid-SL) with high purity of 96 wt%. The bola structure of acid-SL conferred reversible pH-responsive micelle behavior and therefore a distinctive solubilization effect on polar small molecules under neutral pH environment. Based on this, the synergistic solubilization effect of acid-SL in combination with rhamnolipid (RL) was confirmed, with the optimal compound ratio being acid-SL/RL = 0.95:0.05. The compound system significantly improved the solubilization ability under acidic conditions and had superior solubilization capacity for oil-soluble substances such as essential oils, fragrances, and preservatives compared to commonly used solubilizers like Polysorbate 20 and Polyoxyethylene 40.

研究领域: 应用化学 · 环境科学 · 生物学
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ACS Applied Nano Materials · 2021 · IF 5.097

Amphiphilic Rhamnolipid Molybdenum Disulfide Nanosheets for Oil Recovery

Ming Qu,Jirui Hou,Tuo Liang,Pengpeng Qi

Much attention has been directed toward amphiphilic nanosheets in diverse applications owing to their remarkable properties. In this work, the rhamnolipid-molybdenum disulfide nanosheets, environmentally friendly biological-amphiphilic-nanosheets (BANs), are prepared through the one-step simple hydrothermal method. The ultralow concentration of BANs (0.005 wt %), as a solid emulsifier, can emulsify crude oil and stabilize the size of emulsions (oil in water) within 1.2 μm. The adsorption of BANs to the oil–water interface improves the stability of the BANs emulsion, and it both reduces interfacial tension and increases interfacial film strength. Tremendous desorption energy (thousands of KBT) is required to remove a single BAN from the interface to the bulk phase. Besides, BANs can turn an oil-wet surface into an intermediate-wet surface and spread to exfoliate oil film on the solid surface. The evolution of the three-phase contact line experiences two stages: a steep stage and a gentle stage. The spreading behaviors are due to an imbalance between the surface forces and structuring disjoining pressure at the confinement region (wedge film). Moreover, 25.3% of additional oil recovery was observed from the flooding of an ultralow concentration of BANs nanofluid (0.005 wt %) in a natural outcrop core, which is 2.5 mD in permeability at experimental conditions: 120 °C and around 25 × 104 mg/L in salinity. The high tolerance of rhamnolipid-molybdenum disulfide nanosheets to high temperature and harsh salinity is because of synergism between MoS2 nanosheets and rhamnolipid molecules. Additional residual oil reduction is due to a combination of multiple effects such as crude oil emulsification, wettability alteration, interfacial tension reduction, and formation of structuring disjoining pressure. This study presents the possibility to enhance oil recovery in low-permeability reservoirs with harsh conditions.

CAS / MDL: 62-56-6
研究领域: 材料科学 · 化学工程 · 石油工程 · 纳米技术 · 环境科学
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BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY · 2023 ·Vol. 70 ·期 6 ·1806-1816 · IF 2.8

Quantitative determination of rhamnolipid using HPLC-UV through carboxyl labeling

Jing Zhou,Si-Jia Miao,Shi-Zhong Yang,Jin-Feng Liu,Hong-Ze Gang,Bo-Zhong Mu

Rhamnolipid, as a low-toxic, biodegradable and environmentally friendly biosurfactant, has broad application prospects in many industries. However, the quantitative determination of rhamnolipid is still a challenging task. Here, a new sensitive method for the quantitative analysis of rhamnolipid based on a simple derivatization reaction was developed. In this study, 3-[3′-( l -rhamnopyranosyloxy) decanoyloxy] decanoic acid (Rha-C10-C10) and 3-[3′-(2′- O -α- l -rhamnopyranosyloxy) decanoyloxy] decanoic acid (Rha-Rha-C10-C10) were utilized as the representative rhamnolipids. Liquid chromatography–mass spectrometry and high-performance liquid chromatography-ultra violet results showed that these two compounds were successfully labeled with 1 N1-(4-nitrophenyl)-1,2-ethylenediamine. There was an excellent linear relationship between rhamnolipid concentration and peak area of labeled rhamnolipid. The detection limits of the Rha-C10-C10 and Rha-Rha-C10-C10 were 0.018 mg/L (36 nmol/L) and 0.014 mg/L (22 nmol/L), respectively. The established amidation method was suitable for the accurate analysis of rhamnolipids in the biotechnological process. The method had good reproducibility with the relative standard deviation of 0.96% and 0.79%, respectively, and sufficient accuracy with a recovery of 96%–100%. This method was applied to quantitative analysis of 10 rhamnolipid homologs metabolized by Pseudomonas aeruginosa LJ-8. The single labeling method was used for the quantitative analysis of multiple components, which provided an effective method for the quality evaluation of other glycolipids with carboxyl groups.

研究领域: 生物技术 · 分析化学 · 环境科学
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ENERGY & FUELS · 2019 · IF 3.021

Wettability Alteration in Low-Permeability Sandstone Reservoirs by “SiO2–Rhamnolipid” Nanofluid

Di Wang,Shanshan Sun,Kai Cui,Hailan Li,Yejing Gong,Jirui Hou,Zhongzhi Zhang

The wettability condition of a rock’s surface is an enormous parameter for enhanced oil recovery (EOR) in low-permeability reservoirs. It determines the spreading of injected water and the adhesion of residual oil on rock surfaces. In this study, a new nanofluid composed of silica nanoparticles and rhamnolipid in brine was utilized as an effective agent to alter the wettability of a rock’s surface. In order to obtain rock surfaces with different initial wettabilities, hexamethyldisilazane (HMDS) was used for the sample preparation. The measurement of three-phase contact angles for water/air/rock and brine/oil/rock were performed to explore the contact situation between a rock surface and movable fluids, and the spontaneous imbibition test researched the process of oil recovery with nanofluid. By evaluating the experimental measurements, nanofluid showed a significant potential in wettability alteration from oil-wet toward water-wet state, which is an important mechanism for “scraping” oil drops from a rock surface during nano-EOR process. Moreover, a total of nine coreflooding tests were performed to investigate the effects of rock wettability on waterflooding and nanofluid flooding, respectively. The results revealed that an intermediate-wet state of a rock’s surface is in favor of the oil recovery especially for waterflooding, and nanofluid, resulting in an additional 5.3–6.8% increments in oil recovery compared to conventional waterflooding. In conclusion, nanofluids show a significant potential for EOR from low-permeability cores, implying a wide application in oil fields.

CAS / MDL: 7631-86-9
研究领域: 石油工程 · 材料科学 · 表面化学
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International Journal of Environmental Research and Public Health · 2022 ·Vol. 19 ·期 18 ·11518 · IF 4.614

Rhamnolipid-Enhanced ZVI-Activated Sodium Persulfate Remediation of Pyrene-Contaminated Soil

Wenyang Wang,Xiyuan Wang,Hao Zhang,Qingdong Shi,Huapeng Liu

In soil, polycyclic aromatic hydrocarbons (PAHs) are tightly bound to organic components, but surfactants can effectively transform them from a solid to a liquid phase. In this study, the biosurfactant rhamnolipid (RL) was selected as the eluent; shaking elution in a thermostatic oscillator improved the elution rate of pyrene, and the effects of RL concentration, temperature, and elution time on the elution effect were compared. After four repeated washings, the maximum elution rate was 75.6% at a rhamnolipid concentration of 20 g/L and a temperature of 45 °C. We found that 38 μm Zero-Valent Iron (ZVI) had a higher primary reaction rate (0.042 h−1), with a degradation rate of 94.5% when 3 g/L ZVI was added to 21 mM Na2S2O8at 60 °C. Finally, electron paramagnetic resonance (EPR) detected DMPO-OH and DMPO-SO4signals, which played a major role in the degradation of pyrene. Overall, these results show that the combination of rhamnolipid elution and persulfate oxidation system effectively remediated pyrene-contaminated soil and provides some implications for the combined remediation with biosurfactants and chemical oxidation.Keywords:soil washing;persulfate;ZVI;rhamnolipid;pyrene

研究领域: 环境科学 · 生物修复
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WATER RESEARCH · 2014 · IF 5.323

Adsorptive removal of methylene blue by rhamnolipid-functionalized graphene oxide from wastewater

Zhibin Wu,Hua Zhong,Xingzhong Yuan,Hou Wang,Lele Wang,Xiaohong Chen,Guangming Zeng,Yan Wu

In this article, a rhamnolipid-functionalized graphene oxide (RL-GO) hybrid was prepared by one-step ultrasonication and adsorptive removal of methylene blue (MB) from both artificial and real wastewater by the RL-GO was investigated. The Scanning electron microscopy (SEM), Transmission electron microscopy (TEM), Fourier transform infrared spectrum (FT-IR), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Brunauer–Emmett–Teller (BET) area and Zeta potential analysis were used to characterize the adsorbent. The results showed that RL-GO had abundant functional groups and a mesopores feature. MB adsorption by the RL-GO increased with increase in adsorbent dose, pH, temperature and initial MB concentration, while it was insensitive to ionic strength variation. The adsorption kinetics fitted well to the pseudo-second-order model with correlation coefficients greater than 0.999. The Intra-particle diffusion and Boyd's film-diffusion models showed that the rate-controlled step was dominated by film-diffusion in the beginning and then followed by intra-particle diffusion. The adsorption isotherm was fitted by adsorption models with the suitability in order of BET > Freundlich > Langmuir > Temkin, based on comparison between correlation coefficients. Thermodynamic analysis of equilibriums suggested that the adsorption MB on RL-GO was spontaneous and endothermic. The adsorption mechanism was also proposed to be electrostatic attraction, π–π interaction and hydrogen bond . In addition, the real wastewater experiment, the regeneration study and the comparative cost analysis showed that the RL-GO composites could be a cost-effective and promising sorbent for MB wastewater treatment owing to its high efficiency and excellent reusability.

研究领域: 环境科学 · 材料科学
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WATER SCIENCE AND TECHNOLOGY · 2017 ·Vol. 76 ·期 5 ·1167-1176 · IF 1.197

Biosurfactant rhamnolipid enhanced modification of corn stalk and its application for sorption of phenanthrene

Tong Le,Liu Weiting,Lin Weijia,Guo Chuling,Yang Jing,Wei Yanfu,Xie Yingying,Liu Shasha,Dang Zhi

The application of modified agricultural wastes for removing polycyclic aromatic hydrocarbons (PAHs) from water is gaining a growing interest. However, most modified methods using synthetic chemicals may cause secondary pollution. To overcome this limitation, in this study, a rhamnolipid modified corn stalk (RL-CS) for the removal of phenanthrene (PHE) from aqueous solution was prepared using a rhamnolipid-enhanced acid modification method. RL-CS with higher surface area and lower polarity exhibited higher PHE removal efficiency than that of raw corn stalk (RCS). The adsorption kinetics of RL-CS fitted well with pseudo-second-order kinetics (R 2 > 0.999). Sorption coefficients and carbon-normalized sorption coefficient of RL-CS were 4.68 and 2.86 times higher than that of RCS. Sorption process of RL-CS was nonlinear. Meanwhile, the sorption was an exothermic process and could occur spontaneously. The present study demonstrated that biosurfactant-modified biosorbent RL-CS may be of great potential for the removal of low concentrations of PAHs from the contaminated waters.

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MOLECULES · 2021 ·Vol. 26 ·期 3 ·560 · IF 4.412

The Formation of Chitosan-Coated Rhamnolipid Liposomes Containing Curcumin: Stability and In Vitro Digestion

Wei Zhou,Ce Cheng,Li Ma,Liqiang Zou,Wei Liu,Ruyi Li,Yupo Cao,Yuhuan Liu,Roger Ruan,Jihua Li

There is growing interest in developing biomaterial-coated liposome delivery systems to improve the stability and bioavailability of curcumin, which is a hydrophobic nutraceutical claimed to have several health benefits. The curcumin-loaded rhamnolipid liposomes (Cur-RL-Lips) were fabricated from rhamnolipid and phospholipids, and then chitosan (CS) covered the surface of Cur-RL-Lips by electrostatic interaction to form CS-coated Cur-RL-Lips. The influence of CS concentration on the physical stability and digestion of the liposomes was investigated. The CS-coated Cur-RL-Lips with RL:CS = 1:1 have a relatively small size (412.9 nm) and positive charge (19.7 mV). The CS-coated Cur-RL-Lips remained stable from pH 2 to 5 at room temperature and can effectively slow the degradation of curcumin at 80 °C; however, they were highly unstable to salt addition. In addition, compared with Cur-RL-Lips, the bioavailability of curcumin in CS-coated Cur-RL-Lips was relatively high due to its high transformation in gastrointestinal tract. These results may facilitate the design of a more efficacious liposomal delivery system that enhances the stability and bioavailability of curcumin in nutraceutical-loaded functional foods and beverages.Keywords:liposomes;chitosan;curcumin;rhamnolipids;stability;in vitro digestion

CAS / MDL: 458-37-7
研究领域: 食品科学 · 生物医学工程
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ENERGY & FUELS · 2023 · IF 5.3

Synergistic Effects of SiO2-Rhamnolipid Nanofluid on Oil-Water Distribution in Low-Permeability Reservoirs

Di Wang,Ying Zhang,Yijing Luo,Zhiyong Zhang,Zhongzhi Zhang

The application of nanofluid in enhancing oil recovery (EOR) is eliciting considerable interest from researchers. The present study investigates the impact of a novel environmentally friendly nanofluid, composed of rhamnolipid and SiO2 nanoparticles, on oil-water distributions in micro/nano pore spaces, suggesting the potential in EOR from low-permeability reservoirs. We conduct comprehensive experiments, including contact angle measurement, micromodel tests, and nuclear magnetic resonance (NMR) core displacement experiments, to research the synergistic effects of biosurfactant and SiO2 nanoparticles on oil-water distribution changes. Firstly, the contact angle of a liquid droplet on rock surfaces provides a quantitative characterization of water phase spreading on pore walls. The results indicate that the nanofluid injection is advantageous in enhancing the swept volume of the water phase. Secondly, the visualization of fluid mobilization and migration in micro/nano pores is demonstrated by micromodel test. Residual oil is mobilized from stagnant zones with nanofluid injection, and subsequently recovered by waterflooding. Moreover, the micromodel observations exhibit that the nanofluid can disperse the trapped oil into small oil droplets and displace them. Finally, the NMR core displacement experiments clarify the main EOR mechanisms in microporous spaces using nanofluid. As compared to brine and rhamnolipid solution, nanofluid is more likely to motivate trapped oil, thereby increasing the swept volume of the injection fluids. Besides, the distribution changes of residual oil are also influenced by the reservoir’s permeability. As the permeability of experimental cores decreases from 48.5 mD to 0.1 mD, the swept volume of nanofluid gradually expands from larger to smaller pores (from >1000 nm to 1–10 nm). The nanofluid decreases the residual oil saturation of three cores by 3.97%, 4.97%, and −1.65%, respectively, compared to the rhamnolipid-only solution. The increase in residual oil saturation observed in the core sample with 0.1 mD suggests that the re-aggregate of activated oil induces changes in oil-water distribution.

CAS / MDL: 7631-86-9
研究领域: 石油工程 · 环境科学 · 材料科学
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ENERGY & FUELS · 2018 · IF 3.024

Synergistic Effect of Silica Nanoparticles and Rhamnolipid on Wettability Alteration of Low Permeability Sandstone Rocks

Di Wang,Shanshan Sun,Te Sha,Tongjing Liu,Honghong Dong,Kai Cui,Hailan Li,Yejing Gong,Jirui Hou,Zhongzhi Zhang,Pengcheng Fu

Wettability modification is one of the main mechanisms to increase oil recovery from low-permeability oil reservoirs. Nanofluids composed of nanoparticles can be used as modifiers to alter wettability from oil-wet to water-wet condition thus to promote hydrocarbon recovery. Biosurfactants, which are candidates to replace synthetic surfactants for industrial applications, have the potential to prepare nanofluids. In this study, nanofluids prepared by dispersing SiO2 nanoparticles in rhamnolipid solution (hereby named bionanofluids) were considered potential wettability modifiers to apply to petroleum recovery from low-permeability sandstone reservoirs. Analyses via visual observation, optical absorbance measurement, ζ-potential determination, and particle size measurements demonstrated that the bionanofluids with 25 ppm rhamnolipids maintained an optimal stability. The effect of bionanofluids on wettability alteration was investigated through contact angle measurement and imbibition test. The results showed that bionanofluids could alter the wettability of oil-wet sandstone to strongly water-wet. The best performance was achieved with a nanoparticle concentration of 1000 ppm. Additionally, a micromodel test using rhamnolipid solution and bionanofluid was carried out to evaluate the synergistic effects of SiO2 nanoparticles and rhamnolipid on displacing oil. Bionanofluid injection following biosurfactant flooding was shown to improve oil recovery, yielding an additional 5% production. These results reveal that the bionanofluid prepared with SiO2 and rhamnolipids not only remained stable but also provided a potential way for enhanced oil recovery.

研究领域: 石油工程 · 纳米技术 · 表面化学 · 提高采油率 · 胶体与界面科学
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JOURNAL OF CONTAMINANT HYDROLOGY · 2026 · IF 5.5

Insight into the inhibitory role of rhamnolipid in the adsorption of neonicotinoid pesticides onto biochars

Songting Wang,Bin Wang,Kunyu Wen,Yanbin Ma,Usman Farooq,Zhichong Qi,Taotao Lu,Li Zhang,Shuangcheng Tang

Biochar, an economical porous carbonaceous material, exhibits considerable potential for diverse applications, particularly in soil remediation and wastewater treatment. Rhamnolipid—a ubiquitous biosurfactant in natural environments—may significantly influence the interaction between biochar and neonicotinoid pesticides. To evaluate this, the adsorption of two representative neonicotinoid pesticides (nitenpyram and dinotefuran) on biochars produced at 300 °C and 750 °C (BC_300 and BC_750) was investigated in the presence of rhamnolipid. The adsorption kinetics were well described by the pseudo-second-order model ( R 2  = 0.994–0.999), and the isotherms by the Langmuir model ( R 2  = 0.951–0.997). In the absence of biosurfactants, BC_750 exhibited substantially higher adsorption capacity for both neonicotinoid pesticides compared to BC_300. Furthermore, nitenpyram demonstrated greater adsorption affinity to the biochars than dinotefuran. These differences are primarily attributed to variations in the physicochemical properties of the biochars, including surface area, aromaticity, and surface functional groups, as well as the molecular structures of the pesticides, particularly the presence of nitrogen-containing heterocyclic moieties. More importantly, rhamnolipid suppressed the adsorption of neonicotinoid pesticides onto both biochars, primarily through pore blockage, competitive adsorption, and steric hindrance. For instance, the maximum adsorption capacity ( q max ) of nitenpyram onto BC_300 declined from 7.3 mg/g (without rhamnolipid) to 2.8 mg/g (with 30 mg/L rhamnolipid). Additionally, for a given biochar, the inhibitory effect of rhamnolipid on nitenpyram adsorption was more sensitive to variations in biosurfactant concentration compared to dinotefuran. This enhanced inhibition stemmed from the disruption of π–π interactions between nitenpyram and the biochar. Additionally, the inhibitory effect of rhamnolipid on pesticide adsorption decreased progressively from pH 3.0 to 10.0 due to the pH-dependent adsorption behavior of the biosurfactant on the biochars. These findings highlight the necessity of considering the influence of coexisting biosurfactants when employing biochar as an amendment in soil/water systems.

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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Immune enhancement of rhamnolipid/manganese calcium phosphate mineralized nanoparticle: A promising subunit antigen delivery system

Zheng Jia,Xinyao Zhou,Jingjing Liu,Xinqi De,Yifan Li,Zaixing Yang,Haoyuan Duan,Fang Wang,Junwei Ge

The use of biomimetic mineralization strategy is promising to solve the problem of poor stability and immune effect of subunit antigens. However, non-specifically inducing protein mineralization is still a challenge. we hypothesized that rhamnolipids with both protein and metal binding capacity could be used to develop more functional and biocompatible calcium mineralized nanoparticle (RMCP). The results show that rhamnolipids synergistically enhanced the mineralization of protein with manganese ions and improved 21 % the loading antigens of RMCP compared to manganese calcium phosphate nanoparticles. Transmission electron microscopy (TEM) and Dynamic Light Scattering (DLS) showed particle size of RMCP is 260 ± 12.1 nm with spherical morphology. In vitro experiments have shown that RMCP effectively activate immune cells through the cGAS-STING and NLRP3 pathways and demonstrated a higher level of cytokines in RAW264.7 Macrophages. In vivo, RMCP triggered an increased IgG titer with 16.5-fold IgG2a/IgG1 ratio compared to the aluminum adjuvant which improved the recovery status after challenge in mice. We used biological surfactants for the first time to enhance the biomimetic mineralization process of subunit antigen, which provides a new approach for constructing calcium-based biocompatible antigen delivery vectors, helping to develop a new generation of stable, efficient, and safe subunit vaccines.

CAS / MDL: 10043-52-4 7785-87-7
研究领域: 免疫学 · 纳米技术 · 疫苗开发 · 生物材料
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