Synthesis and properties of sugar-based surfactants alkoxyethyl β-D-glucopyranoside

Ji, Shanwei; Shen, Wangzhen; Chen, Langqiu; Zhang, Yanhua; Wu, Xiubing; Fan, Yulin; Fu, Fang; Chen, Guoyong

doi:10.1016/j.colsurfa.2018.12.034

Cited by 23 publications

(41 citation statements)

References 60 publications

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“…Figure 2a Figure 3 shows the solubility of glucopyranosides (4). As described in the literature, 38,39 From the above discussion, it was obvious that the hydrophilic spacer strengthened the hydrophilicity and improved the water solubility.…”

Section: Resultsmentioning

confidence: 62%

“…Ji 38 reported that the water solubility of alkoxyethyl β-Dglucosides (6a−6h) with the hydrophilic spacer (−OCH 2 CH 2 −) reduced with an increase in the alkyl chain length. Figure 2a Figure 3 shows the solubility of glucopyranosides (4).…”

Section: Resultsmentioning

confidence: 99%

“…Ji reported that the water solubility of alkoxyethyl β- d -glucosides ( 6a–6h ) with the hydrophilic spacer (−OCH 2 CH 2 −) reduced with an increase in the alkyl chain length. Figure a also shows this similar water solubility for alkoxy ethoxyethyl β- d -glucosides ( 4a–4h ) with a stronger hydrophilic spacer ((−OCH 2 CH 2 −) m , m = 2) at 25 °C.…”

Section: Resultsmentioning

confidence: 99%

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Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

Fan

Chen

et al. 2020

J. Agric. Food Chem.

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Dioxyethene fragment (−(OCH2CH2)2−) was introduced into traditional alkyl β-d-glucopyranosides to ameliorate the water solubility, and eight nonionic surfactants, that is, alkoxy ethoxyethyl β-d-glucopyranosides with alkyl chain lengths (n = 6–16), were synthesized and characterized. Their hydrophilic and lipophilic balance number, water solubility, critical micelle concentration (cmc), γcmc, Γmax, and hygroscopic rate decreased with an increase in the alkyl chain length. Hexadecoxy ethoxyethyl β-d-glucopyranoside had no water solubility at 25 °C. Decoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the toluene/water and n-octane/water systems and the strongest foaming property, whereas dodecoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the rapeseed oil/water system. Such β-d-glucopyranosides (n = 6–12) exhibited excellent surface activity. In addition, for the binary mixture of alkoxy ethoxyethyl β-d-glucopyranosides (n = 8, 10, 12) and sodium dodecyl sulfate or cetyl trimethyl ammonium chloride, their cmc values were lower than the pure β-d-glucopyranosides, indicating that they had synergistic interactions. The fan focal conic textures of alkoxy ethoxyethyl β-d-glucopyranosides (n = 7–16) were observed during the cooling process under a polarizing optical microscope. Alkoxy ethoxyethyl β-d-glucopyranosides (n = 14, 16) had the related melting points and the clear points with differential scanning calorimetry. With β-d-glucopyranosides (n = 6–16) and n-butanol as the surfactant and cosurfactant, respectively, and with cyclohexane as the oil phase, the related microemulsion areas in their pseudoternary phase diagram system were investigated with the visual observation at 25 °C. Along with the slashing requirements of petroleum consumption, environmental protection, and green and sustainable development, nonionic sugar-based alkoxy ethoxyethyl β-d-glucopyranosides should be expected to have their potential practical application because of their strengthened hydrophilicity, improved water solubility, and enhanced surface activity.

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Section: Resultsmentioning

confidence: 62%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

Fan

Chen

et al. 2020

J. Agric. Food Chem.

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“…A problem that has not been solved yet is the low yield obtained with alcohols with more than eight carbon atoms due to their low solubility in aqueous mediums (El‐Sukkary et al, 2008). Recently, Ji et al (2019) synthesized alkoxyethyl β‐ d ‐glucopyranosides by adding a polyethylene oxide structure to a conventional alkylglycoside. The addition of this extension to the molecule improved the interfacial properties (Y.…”

Section: Building Blocks and Chemicals Derived From Carbohydratesmentioning

confidence: 99%

Surfactants produced from carbohydrate derivatives: A review of the biobased building blocks used in their synthesis

Ortiz

Alvarado

Zambrano³

et al. 2022

J Surfact & Detergents

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This work reviews the use of carbohydrates and their derivatives as renewable raw materials in the production of surfactants. Methods to attain state‐of‐the‐art carbohydrate‐derived surfactants are described. This includes surfactants widely used nowadays and others that have not yet transcended beyond the academic field. Given the abundance of hydroxyl groups in carbohydrates and the considerable quantity of different surfactant structures that can be generated during their synthesis, selectively obtaining a target product represents a challenge. Therefore, this work focuses on the platform chemicals available to synthesize biobased surfactants. The first part of the review comprises a brief introduction of simple and complex carbohydrates to better understand their chemistry. Then, a description of the processes to obtain biobased building blocks derived from carbohydrates according to the National Renewable Energy Laboratory (NREL, USA), and their usefulness in synthesizing surfactants is presented. This provides an organized inventory of the knowledge around the synthesis–production of surfactants from carbohydrate derivatives, emphasizing raw materials that could be inserted into the circular bioeconomy concept. Finally, the current industry trends and the potential role of biobased surfactants around new dioxane regulations are discussed.

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“…Owing to the fact that the alkyl glucosides are extracted from natural, renewable sources, they are characterized by biodegradability and low toxicity [ 44 ]. Alkyl glucosides display washing, foaming, and emulsifying properties [ 45 ].…”

Section: Introductionmentioning

confidence: 99%

Freeze-Dried Matrices Composed of Degradable Polymers with Surfactant-Loaded Microparticles Based on Pectin and Sodium Alginate

Stachowiak

Kowalonek

2021

Materials

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Gelatin/polyvinylpyrrolidone/hydroxyethyl cellulose/glycerol porous matrices with microspheres made of sodium alginate or pectin and sodium alginate were produced. A surfactant was loaded into these microparticles. The microspheres were characterized using optical microscopy, scanning electron microscopy SEM, and laser diffraction particle size analyzer. For the matrices, the density, porosity, swelling capacity, dissolution in phosphate saline buffer were determined and SEM, mechanical, and thermogravimetric studies were applied. The results showed that the size of the two-component microspheres was slightly larger than that of single-ingredient microparticles. The images confirmed the spherical shape of the microparticles. The prepared matrices had high water uptake ability and porosity due to the presence of hydrophilic polymers. The presence of microparticles in the matrices caused a decrease in these parameters. Degradation of the composites with the microspheres was significantly faster than the matrix without them. The addition of microparticles increased the stiffness and toughness of the prepared materials. The efficiency of the thermal decomposition main stage was reduced in the samples with microspheres, whereas a char residue increased in these composites.

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Synthesis and properties of sugar-based surfactants alkoxyethyl β-D-glucopyranoside

Cited by 23 publications

References 60 publications

Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

Surfactants produced from carbohydrate derivatives: A review of the biobased building blocks used in their synthesis

Freeze-Dried Matrices Composed of Degradable Polymers with Surfactant-Loaded Microparticles Based on Pectin and Sodium Alginate

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