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Ionic liquid-biosurfactant blends as effective dispersants for oil spills: Effect of carbon chain length and degree of saturation

Hassan Shah MU, Bhaskar Reddy AV, Yusup S, Goto M, Moniruzzaman M

Environ Pollut, 2021 Sep 01;284:117119.
PMID: 33906032 DOI: 10.1016/j.envpol.2021.117119

The well-known toxicity of conventional chemical oil spill dispersants demands the development of alternative and environmentally friendly dispersant formulations. Therefore, in the present study we have developed a pair of less toxic and green dispersants by combining lactonic sophorolipid (LS) biosurfactant individually with choline myristate and choline oleate ionic liquid surfactants. The aggregation behavior of resulted surfactant blends and their dispersion effectiveness was investigated using the baffled flask test. The introduction of long hydrophobic alkyl chain with unsaturation (attached to choline cation) provided synergistic interactions between the binary surfactant mixtures. The maximum dispersion effectiveness was found to be 78.23% for 80:20 (w/w) lactonic sophorolipid-choline myristate blends, and 81.15% for 70:30 (w/w) lactonic sophorolipid-choline oleate blends at the dispersant-to-oil ratio of 1:25 (v/v). The high dispersion effectiveness of lactonic sophorolipid-choline oleate between two developed blends is attributed to the stronger synergistic interactions between surfactants and slower desorption rate of blend from oil-water interface. The distribution of dispersed oil droplets at several DOR were evaluated and it was observed that oil droplets become smaller with increasing DOR. In addition, the acute toxicity analysis of developed formulations against zebra fish (Danio rerio) confirmed their non-toxic behavior with LC50 values higher than 400 ppm after 96 h. Overall, the proposed new blends/formulations could effectively substitute the toxic and unsafe chemical dispersants.

Matched MeSH terms: Surface-Active Agents/toxicity
Fulltext Biocompatible and Biodegradable Surfactants from Orange Peel for Oil Spill Remediation

Wang PS, Ahmad A, Nazar M, Rahmah AU, Moniruzzaman M

Molecules, 2023 Aug 01;28(15).
PMID: 37570764 DOI: 10.3390/molecules28155794

Oil spill remediation plays a vital role in mitigating the environmental impacts caused by oil spills. The chemical method is one of the widely recognized approaches in chemical surfactants. However, the most commonly used chemical surfactants are toxic and non-biodegradable. Herein, two biocompatible and biodegradable surfactants were synthesized from orange peel using the ionic liquid 1-butyl-3-methylimidazolium chloride (BMIMCl) and organic solvent dimethylacetamide (CH3CN(CH3)2) as reaction media. The acronyms SOPIL and SOPOS refer to the surfactants prepared with BMIMCl and dimethylacetamide, respectively. The surface tension, dispersant effectiveness, optical microscopy, and emulsion stability test were conducted to examine the comparative performance of the synthesized surfactants. The Baffled flask test (BFT) was carried out to determine the dispersion effectiveness. The toxicity test was performed against zebrafish (Danio rerio), whereas the closed bottle test (CBT) evaluated biodegradability. The results revealed that the critical micelle concentration (CMC) value of SOPIL was lower (8.57 mg/L) than that of SOPOS (9.42 mg/L). The dispersion effectiveness values for SOPIL and SOPOS were 69.78% and 40.30%, respectively. The acute toxicity test demonstrated that SOPIL was 'practically non-toxic' with a median lethal concentration of more than 1000 mg/L after 96 h. The biodegradation rate was recorded as higher than 60% for both surfactants within 28 days, demonstrating their readily biodegradable nature. Considering these attributes, biocompatible and biodegradable surfactants derived from orange peel emerge as a promising and sustainable alternative for oil spill remediation.

Matched MeSH terms: Surface-Active Agents/toxicity
Fulltext Ecotoxicity of commonly used oilfield-based emulsifiers on Guinean Tilapia (Tilapia guineensis) using histopathology and behavioral alterations as protocol

Chris DI, Wokeh OK, Téllez-Isaías G, Kari ZA, Azra MN

Sci Prog, 2024;107(1):368504241231663.
PMID: 38490166 DOI: 10.1177/00368504241231663

This study examined the histological aberrations in the gill and liver tissues and behavioural changes of Tilapia guineensis fingerlings exposed to lethal concentrations of used Oilfield-based emulsifiers for 96 h. Various concentrations of the surfactants were tested, ranging from 0.0 to 15.0 ml/L. The behaviour of the fish was observed throughout the experiment, and the results showed that increasing concentrations of the surfactants led to progressively abnormal behaviour, including hyperventilation and altered opercular beat frequency. These behavioural changes indicated respiratory distress and neurotoxic effects. Histological analysis revealed structural aberrations in the gill and liver tissues, with higher concentrations causing more severe damage, such as lesions, necrosis, inflammation, and cellular degeneration. This implies that surfactants released even at low concentrations are capable of inducing changes in the tissues of aquatic organisms. These findings highlight the toxic effects of the surfactants on fish health and provide biomarkers of toxicity. Future research should focus on understanding the specific mechanisms and long-term consequences of surfactant toxicity on fish genetic composition, populations, and ecosystems to implement effective conservation measures.

Matched MeSH terms: Surface-Active Agents/toxicity
Pulmonary oedema due to inhalation of detergent aerosol

Rao J, Das PK

Malays J Pathol, 1994 Dec;16(2):165-6.
PMID: 9053567

Healthy adult male albino rats were subjected to inhalation of increasing doses of detergent (dioctyl sodium sulfo-succinate) aerosol ranging from 100 mg to 500 mg. Administration of 500 mg of detergent aerosol resulted in peribronchial and focal alveolar oedema in 3 out of 5 animals. The lungs of control animals which were subjected to inhalation of vehicle aerosol (ethanol and saline) did not show any abnormality. It is possible that pulmonary oedema observed in detergent aerosol inhalation may be due to the action of detergents on the surfactant system of the lung.

Matched MeSH terms: Surface-Active Agents/toxicity*
Fulltext Performance of Green Surfactants in the Formulation of Heavy-Duty Laundry Liquid Detergents (HDLD) with Special Emphasis on Palm Based Alpha Methyl Ester Sulfonates (α-MES)

Low SY, Tan JY, Ban ZH, Siwayanan P

J Oleo Sci, 2021 Aug 05;70(8):1027-1037.
PMID: 34248098 DOI: 10.5650/jos.ess21078

Liquid detergent has an increasing demand in North America, Western Europe, and Southeast Asia countries owing to its convenience to use and efficiency to clean. Alpha methyl ester sulfonates (α-MES), an anionic surfactant derived from palm oil based methyl ester, was reported to have lower manufacturing cost, good detergency with less dosage, excellent biodegradability, higher tolerance to hard water, and lower eco-toxicity as compared to linear alkylbenzene sulfonates (LABS). LABS was known as the workhorse of the detergent industry in the 20th century. Although palm-based α-MES was successfully used as the sole surfactant in powder detergent, there are still some unsettled technical issues related to phase stability and viscosity when using this anionic surfactant in heavy-duty laundry liquid detergent formulations. This paper will review not only the market overview of detergents, the application and performance of green surfactants in laundry detergents but also will highlight the technical issues related to the application of palm-based α-MES in laundry liquid detergent and some of the possible methods to overcome the formulation adversities.

Matched MeSH terms: Surface-Active Agents/toxicity
The oral and intratracheal toxicities of ROUNDUP and its components to rats

Adam A, Marzuki A, Abdul Rahman H, Abdul Aziz M

Vet Hum Toxicol, 1997 Jun;39(3):147-51.
PMID: 9167243

The toxicities of ROUNDUP and its component chemicals, glyphosate (N-phosphonomethylglycine) and polyoxyethyleneamine (POEA), were determined at 0, 1, 3, 6 and 24 h following administration to rats. The intratracheal administration of glyphosate (0.2 g/kg), POEA (0.1 g/kg), a mixture of glyphosate (0.2 g/kg) + POEA (0.1 g/kg), or ROUNDUP (containing 0.2 g/kg glyphosate and 0.1 g/kg POEA) elicited immediate respiratory effects which were more severe and which lasted longer in the groups receiving the POEA-containing preparations than in the glyphosate alone group. By 1 h, all test preparations had caused deaths, but more occurred from the POEA-containing preparations than from glyphosate. The po administration of POEA (1 g/kg), the mixture of glyphosate (2 g/kg) +POEA (1 g/kg), or ROUNDUP (containing 2 g/kg glyphosate and 1 g/kg POEA) produced diarrhea and blood-stained weeping from noses. Death was only seen from POEA at 24 h. Glyphosate (2 g/kg po) produced transient diarrhea without nose bleeds; POEA caused diarrhea at 1 h; and the mixture of POEA + glyphosate produced diarrhea later that increased in severity with time. Bloody nose secretions were seen only with the preparations that contained POEA. No deaths, respiratory effects or bloody nose secretions occurred in controls given saline. Both POEA and glyphosate caused lung hemorrhages and lung epithelial cell damage with po or intratracheal exposures. These results indicate POEA and preparations that contained POEA were more toxic than glyphosate.

Matched MeSH terms: Surface-Active Agents/toxicity*
Occurrence, fate and environmental risk of linear alkylbenzene sulfonate in the Langat and Selangor River basins, Malaysia

Sakai N, Shirasaka J, Matsui Y, Ramli MR, Yoshida K, Ali Mohd M, et al.

Chemosphere, 2017 Apr;172:234-241.
PMID: 28081507 DOI: 10.1016/j.chemosphere.2016.12.139

Five homologs (C10-C14) of linear alkylbenzene sulfonate (LAS) were quantitated in surface water collected in the Langat and Selangor River basins using liquid chromatography-tandem mass spectrometry (LC-MS/MS). A geographic information system (GIS) was used to spatially analyze the occurrence of LAS in both river basins, and the LAS contamination associated with the population was elucidated by spatial analysis at a sub-basin level. The LAS concentrations in the dissolved phase (<0.45 μm) and 4 fractions separated by particle size (<0.1 μm, 0.1-1 μm, 1-11 μm and >11 μm) were analyzed to elucidate the environmental fate of LAS in the study area. The environmental risks of the observed LAS concentration were assessed based on predicted no effect concentration (PNEC) normalized by a quantitative structure-activity relationship model. The LAS contamination mainly occurred from a few populated sub-basins, and it was correlated with the population density and ammonia nitrogen. The dissolved phase was less than 20% in high contamination sites (>1000 μg/L), whereas it was more than 60% in less contaminated sites (<100 μg/L). The environmental fate of LAS in the study area was primarily subject to the adsorption to suspended solids rather than biodegradation because the LAS homologs, particularly in longer alkyl chain lengths, were considerably absorbed to the large size fraction (>11 μm) that settled in a few hours. The observed LAS concentrations exceeded the normalized PNEC at 3 sites, and environmental risk areas and susceptible areas to the LAS contamination were spatially identified based on their catchment areas.

Matched MeSH terms: Surface-Active Agents/toxicity
Eye irritation potential: palm-based methyl ester sulphonates

Yusof NZ, Azizul Hasan ZA, Abd Maurad Z, Idris Z

Cutan Ocul Toxicol, 2018 Jun;37(2):103-111.
PMID: 28693384 DOI: 10.1080/15569527.2017.1352595

AIM: To evaluate eye irritation potential of palm-based methyl ester sulphonates (MES) of different chain lengths; C12, C14, C16, C16:18.
METHODS: The Bovine Corneal Opacity and Permeability test method (BCOP), OECD Test Guideline 437, was used as an initial step to study the inducing effect of palm-based MES on irreversible eye damage. The second assessment involved the use of reconstructed human corneal-like epithelium test method, OECD Test Guideline 492 using SkinEthic™ Human Corneal Epithelium to study the potential effect of palm-based MES on eye irritancy. The palm-based MES were prepared in 10% solution (w/v) in deionized water and tested as a liquid and surfactant test substances whereby both test conducted according to the liquid/surfactant treatment protocol.
RESULTS: The preliminary BCOP results showed that palm-based MES; C12, C14, C16, C16:18 were not classified as severe eye irritants test substances with in vitro irritancy score between 3 and the threshold level of 55. The second evaluation using SkinEthic™ HCE model showed that palm-based MES; C12, C14, C16, C16:18 and three commercial samples were potentially irritants to the eyes with mean tissue viability ≤ 60% and classified as Category 2 according to United Nations Globally Harmonized System of Classification and Labelling of Chemicals. However, there are some limitations of the proposed ocular irritation classification of palm-based MES due to insolubility of long chain MES in 10% solution (w/v) in deionized water.
CONCLUSION: Therefore, future studies to clarify the eye irritation potential of the palm-based MES will be needed, and could include; methods to improve the test substance solubility, use of test protocol for solids, and/or inclusion of a benchmark anionic surfactant, such as sodium dodecyl sulphate within the study design.

Matched MeSH terms: Surface-Active Agents/toxicity*
Synthesis and characterization of choline-fatty-acid-based ionic liquids: A new biocompatible surfactant

Ali MK, Moshikur RM, Wakabayashi R, Tahara Y, Moniruzzaman M, Kamiya N, et al.

J Colloid Interface Sci, 2019 Sep 01;551:72-80.
PMID: 31075635 DOI: 10.1016/j.jcis.2019.04.095

Ionic liquid (IL) surfactants have attracted great interest as promising substitutes for conventional surfactants owing to their exceptional and favorable physico-chemical properties. However, most IL surfactants are not eco-friendly and form unstable micelles, even when using a high concentration of the surfactant. In this study, we prepared a series of halogen-free and biocompatible choline-fatty-acid-based ILs with different chain lengths and degrees of saturation, and we then investigated their micellar properties in aqueous solutions. Characterization of the synthesized surface-active ILs (SAILs) was performed by 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, differential scanning calorimetry, and elemental analysis. The surface-active properties of the SAILs were investigated by tensiometry, conductometry, and dynamic light scattering measurements. The critical micelle concentration of the SAILs was found to be 2-4 times lower than those of conventional surfactants. The thermodynamic properties of micellization (ΔG0m, ΔH0m, and ΔS0m) indicate that the micellization process of the SAILs is spontaneous, stable, and entropy-driven at room temperature. The cytotoxicity of the SAILs was evaluated using mammalian cell line NIH 3T3. Importantly, [Cho][Ole] shows lower toxicity than the analogous ILs with conventional surfactants. These results clearly suggest that these environmentally friendly SAILs can be used as a potential alternative to conventional ILs for various purposes, including biological applications.

Matched MeSH terms: Surface-Active Agents/toxicity