Biodegradation of 2-Sulfonatofatty Acid Methyl Ester (α-SFMe).II

Masuda, Mitsuteru; Odake, H.; Miura, Kazuaki; Itō, Keiko; Yamada, Kaoru; Oba, Kenkichi

doi:10.5650/jos1956.42.905

Cited by 13 publications

(7 citation statements)

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“…Primary biodegradation of methyl α-sulfonyl fatty acid esters was reported to be complete within 3-10 d under aerobic conditions (10,(32)(33)(34)(35). Their ultimate biodegradation reaches about 80% within 20 d (35,36). These results are similar to those observed for α-sulfonated sugar esters in this study.…”

Section: Resultssupporting

confidence: 89%

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Baker

Matthews

Suares

et al. 2000

J Surfact & Detergents

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Ultimate aerobic biodegradabilities of an array of sugar ester surfactants were determined by International Standards Organisation method 7827, "Water Quality-Evaluation in an Aqueous Medium of the Aerobic Biodegradability of Organic Compounds, Method by Dissolved Organic Carbon" (1984). The surfactants were nonionic sugar esters with different-sized sugar head groups (formed from glucose, sucrose, or raffinose) and different lengths and numbers of alkyl chains [formed from lauric (C 12 ) or palmitic (C 16 ) acid]. Analogous anionic sugar ester surfactants, formed by attaching an α-sulfonyl group adjacent to the ester bond, and sugar esters with α-alkyl substituents were also studied. It was found that variations in sugar head group size or in alkyl chain length and number do not significantly affect biodegradability. In contrast, the biodegradation rate of sugar esters with α-sulfonyl or α-alkyl groups, although sufficient for them to be classified as readily biodegradable, was dramatically reduced compared to that of the unsubstituted sugar esters. An understanding of the relationship between structure and biodegradability provided by the results of this study will aid the targeted design of readily biodegradable sugar ester surfactants for use in consumer products.Surfactant biodegradability is a crucial factor in determining whether their concentrations in the environment remain below detrimental levels. Surfactants derived from sugar fatty acid esters are attractive because of their ready biodegradability, low toxicity, low irritation to eyes and skin, and the renewable nature of the sugar and fatty acid starting materials. They are widely used in food, cosmetic, and pharmaceutical formulations (1-3). Physicochemical properties of these surfactants can be tailored to suit potential applications by varying the sugar head group size and the length and number of alkyl chains. As well as nonionic surfactants, analogous anionic sugar ester surfactants can be produced by incorporation of a sulfonate group. These anionic sugar esters are more water soluble than their nonionic counterparts and may more easily replace conventional anionic surfactants in product formulations. Many effects of structural variations on the physicochemical properties of sugar ester surfactants have been reported (4-6).Sucrose fatty acid esters are rapidly biodegradable (7-13). However, the relationship between biodegradability and chemical structure of sugar ester surfactants has not been comprehensively studied. The aim of the current research was to investigate the ultimate aerobic biodegradation of surfactants derived from sugar fatty acid esters so as to develop an understanding of the relationships between surfactant structure and biodegradability. The biodegradabilities of an array of sugar ester surfactants in which the structure was systematically varied were determined. Structures of the surfactants studied are indicated in Scheme 1. Sugar head group size was varied from a monosaccharide (glucose) to a trisaccharide (raffinose). ...

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Section: Resultssupporting

confidence: 89%

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Baker

Matthews

Suares

et al. 2000

J Surfact & Detergents

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“…The main driving force to produce this surfactant commercially has been its superior detergency (4)(5)(6) and biodegradability (7)(8)(9)(10). The physicochemical properties, such as critical micelle concentration (CMC), interfacial tension, surface tension, Krafft point, and water hardness tolerance of different chain lengths of the hydrophobic portion, have been well documented (5,(10)(11)(12)(13).…”

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confidence: 99%

Phase diagram of α‐sulfonate methyl esters derived from palm stearin/alcohol/water systems

Lim

2004

J Surfact & Detergents

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Phase diagrams of α-sulfonate methyl ester derived from palm stearin (α-SMEPS)/alcohol/water systems were mapped at 30 ± 0.1°C. Two main regions-an isotropic and a lamellar liquid crystalline-were the focal points in this system. An increase in alcohol chain length decreased the isotropic region and increased the lamellar liquid crystal region. In the isotropic region, self-assembly of α-SMEPS at different alcohol chain lengths was determined by using conductivity and viscosity measurements. The phase boundaries of micelle to bicontinuous structure and bicontinuous structure to inverse micelle transitions in the isotropic regions are proposed from these analytical methods. The increase in alcohol chain length shifted the micelle ↔ bicontinuous structure to the water-rich corner, and the bicontinuous structure ↔ inverse micelle transition moved toward the alcohol-rich corner.

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“…In Japan, 2-sulfonato fatty acid methyl ester sodium salt (MES) has been used as one of the main surfactants in heavy-duty household granular detergents 1) . The eco-toxicological effects 2) and the biodegradability [3][4][5] of MES were reported previously. MES is readily and fully biodegradable under aerobic conditions; therefore, it can be removed efficiently by biological wastewater treatment systems such as activated sludge [3][4][5] .…”

Section: Introductionmentioning

confidence: 53%

“…conventional biological wastewater treatment systems because it is readily and fully biodegradable under aerobic conditions [3][4][5] . It has already been assessed that the surfactants LAS, alcohol ethoxylates, and alkyl amine oxide in household detergents pose a low risk; in this case also, the PECs are less than the PNECs 6) .…”

Section: K Miuramentioning

confidence: 99%

Aquatic Risk Assessment of 2-Sulfonato Fatty Acid Methyl Ester Sodium Salt (MES)

Miura

2007

J. Oleo Sci.

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The aquatic risk of 2-sulfonato fatty acid methyl ester sodium salt (MES) used in household detergents was assessed. The environmental exposure assessment expressed as predicted environmental concentration (PEC) was determined on the basis of monitoring results from the seven sites of four rivers in the urban area in Tokyo and Osaka. The 95 percentile as well as geometric mean of the MES concentration was found to exhibit a good correlation with the geometric mean of the Biochemical Oxygen Demand (BOD; the latter's regression was greater than 0.99). The predicted no effect concentration (PNEC) for the aquatic environment was estimated by performing chronic assays of algae and daphnia. The risk characterization ratio (RCR: PEC/PNEC) was less than 1. Therefore, it is concluded that MES will not adversely affect the aquatic environment in Japan.

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Biodegradation of 2-Sulfonatofatty Acid Methyl Ester (α-SFMe).II

Cited by 13 publications

References 0 publications

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Sugar fatty acid ester surfactants: Structure and ultimate aerobic biodegradability

Phase diagram of α‐sulfonate methyl esters derived from palm stearin/alcohol/water systems

Aquatic Risk Assessment of 2-Sulfonato Fatty Acid Methyl Ester Sodium Salt (MES)

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