Physicochemical, foaming and biological properties of lowly irritant anionic sugar-based surfactants

Bois, Rémy; Abdellahi, Bemba; Mika, Benjamin; Golonu, Séma; Vigneron, Pascale; Chagnault, Vincent; Drelich, Audrey; Pourceau, Gwladys; Wadouachi, Anne; Vayssade, Muriel; Pezron, Isabelle; Nesterenko, Alla

doi:10.1016/j.colsurfa.2020.125525

Cited by 9 publications

(3 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Carbohydrate-based surfactants can also be prepared via chemical synthesis from monosaccharides isolated from biomass. The commercial production of carbohydrate-based surfactants started in the 1980s and is mostly based on sucrose and glucose derivatives. − Much less is known about surfactants derived from l -Ara and d -GalA, monosaccharides that can be obtained from SBP in bulk quantities without direct competition with food production. ,, …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

Jansen,

van Rijbroek,

den Bakker

et al. 2023

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Herein, we report a method for the synthesis of biobased surfactants derived from sugar beet pulp (SBP) monosaccharides, L-Ara and D-GalA. The surfactants were prepared via one-pot reductive amination, allowing the introduction of different alkyl chain lengths and methyl modifications. Optimal reaction conditions were established to achieve high yields and easy purification. The synthesized surfactants including the tertiary amines exhibited desirable properties, including solubility, foamability, and reduction of surface tension. Notably, the anionic surfactants derived from D-GalA demonstrated better solubility and foam performance compared to those derived from L-Ara. In addition, these surfactants exhibited surface tension and critical micelle concentration (CMC) comparable to those of the commercial surfactant sodium lauryl ether sulfate (SLES). Furthermore, the biodegradable surfactant GalA1.8 displayed excellent emulsifying properties and low skin irritation potential. On the L-Ara surfactant with a short chain, Ara1.6 has potential as a hydrotrope. These findings suggest that biobased surfactants derived from SBP monosaccharides have promising applications in various industries, including pharmaceuticals, cosmetics, detergents, and chemicals.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

Jansen,

van Rijbroek,

den Bakker

et al. 2023

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…As green and biodegradable natural compounds, 20 sugars are frequently used to prepare sugar-based surfactants. Up to now, many commercially available sugar-based surfactants, like APG, 21 AEG, 22 SE, 23 MEGA-12, 24 and newly designed surfactants, such as DDM, 25 GlcNC12S, 26 GlcCC12S, 26 OBTG, 27 and ALA 14, 28 have been developed. Malik and co-workers reported the oxidation of citric acid by MnO 4 − with the assistance of biocompatible natural sugar-based surfactant crocin.…”

Section: Introductionmentioning

confidence: 99%

An efficient and green procedure for transformation of thiols to disulfides and thioamides in AGA8 aqueous micelles

et al. 2023

View full text Add to dashboard Cite

show abstract

“…In addition, aldonamides have been described as intermediates for the synthesis of glycoconjugates, evaluated as glucose-sensing materials [13], or for the synthesis of neo-glycoconjugates [14][15][16][17]. For several years, our group has been involved in the design of N-alkylaldonamides and their derivatives as sugar-based surfactants [18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Fast and Efficient Mechanosynthesis of Aldonamides by Aminolysis of Unprotected Sugar Lactones

Bil

Abdellahi

Pourceau

et al. 2022

Sustainable Chemistry

Self Cite

View full text Add to dashboard Cite

Sugar amides, such as aldonamides, are interesting, sugar-based molecules used in various fields, from detergency to medicine. Nevertheless, their valorization, especially as alternatives to petroleum-based substances, can be slowed down by their synthetic pathway, which is generally not in accordance with green chemistry principles, and is also not economically competitive. We propose herein a fast procedure for the synthesis of aldonamide-derived glycoconjugates with mechanochemistry. The conditions were first optimized with galactonolactone, used as a model lactone, and dodecylamine. After only 5 min of grinding of stoechiometric amounts of amine and lactone, in the presence of water used as a Liquid Assisted Grinding (LAG) agent, the corresponding galactonamide was isolated with a high yield (90%) after a simple aqueous work-up. The optimized conditions were then applied to a wide variety of amines and sugar lactones, showing the versatility of the methodology. Gluco- and ribono-lactone exhibited similarly excellent reactivity, showing that the procedure is not sugar-dependent. Furthermore, the procedure was shown to be compatible with various functional groups such as alkene, alkyne, thiol, ester and hydroxyl.

show abstract

Physicochemical, foaming and biological properties of lowly irritant anionic sugar-based surfactants

Cited by 9 publications

References 48 publications

Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

Synthesis and Performance of Biobased Surfactants Prepared by the One-Pot Reductive Amination of l-Arabinose and d-Galacturonic Acid

An efficient and green procedure for transformation of thiols to disulfides and thioamides in AGA8 aqueous micelles

Fast and Efficient Mechanosynthesis of Aldonamides by Aminolysis of Unprotected Sugar Lactones

Contact Info

Product

Resources

About