d-Xylose-based surfactants: Synthesis, characterization and molecular modeling studies

Klai, Nadia; Bidjou-Haiour, Chahra; Bouquillon, Sandrine

doi:10.1016/j.crci.2014.11.007

Cited by 7 publications

(8 citation statements)

References 22 publications

(10 reference statements)

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“…Various catalytic acids have been used in the presence of a fatty alcohol to synthesize the corresponding xylosides using the Fischer method: sulfuric acid or p-toluenesulfonic acid (PTSA), [14][15][16] acetyl chloride, 14,17 acidic resin 14 or a catalytic amount of Lewis acid. 18 The use of ionic liquids as solvents with a catalytic amount of Lewis acid for the synthesis of octyl xylopyranosides has allowed increased reaction yields while maintaining a-selectivity.…”

Section: Synthesis Of Oand S-xylopyranosidesmentioning

confidence: 99%

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β-Xylopyranosides: synthesis and applications

et al. 2015

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Section: Synthesis Of Oand S-xylopyranosidesmentioning

confidence: 99%

“…250 Fischer glycosylation generally leads to mixtures of anomers, and the average DP of APGs is generally near 1. 16 Alkyl xylosides represent attractive targets for this type of application and are part of the agro-resource waste valorisation philosophy.…”

Section: B-xylopyranosides As Surfactantsmentioning

confidence: 99%

β-Xylopyranosides: synthesis and applications

et al. 2015

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“…Xylose is currently reduced into xylitol, converted into furfural or fermented into ethanol [7]. Although few pentose-based surfactants were previously developed, some recent studies described the chemical synthesis of alkyl pentosides and pentose-based fatty esters [9][10][11][12][13]. These syntheses often require high energy and various catalysts that might not be compatible with green chemistry processes.…”

Section: Introductionmentioning

confidence: 99%

d-Xylose and l-arabinose laurate esters: Enzymatic synthesis, characterization and physico-chemical properties

Thomas

Muzard

Deleu

et al. 2018

Enzyme and Microbial Technology

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Efficient enzymatic synthesis of d-xylose and l-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalysed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of d-xylose or l-arabinose and vinyllaurate at 50 °C. In case of l-arabinose, one monoester and one diester were obtained in a 57% overall yield. A more complex mixture was produced for d-xylose as two monoesters and two diesters were synthesized in a 74.9% global yield. The structures of all these pentose laurate esters was solved. Results demonstrated that the esterification first occurred regioselectively onto the primary hydroxyl groups. Pentose laurate esters exhibited interesting features such as low critical aggregation concentrations values all inferior to 25 μM. Our study demonstrates that the enzymatic production of l-arabinose and d-xylose-based esters represents an interesting approach for the production of green surfactants from lignocellulosic biomass-derived pentoses.

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“…Pentosane surfactants, in particular alkyl xylosides, are characterized by excellent surface and application properties compared to better known alkyl glucosides . Pentosane surfactants, mainly as alkyl polyxyloside, are recently offered on commercial scale by Wheatoleo .…”

Section: Introductionmentioning

confidence: 99%

“…The yield of xylosides were up to 80% . p‐Toluenesulfonic acid as catalyst was also used in another method described by Bouquillon . Reaction was carried out in THF as a solvent.…”

Section: Introductionmentioning

confidence: 99%

Micellar Route of the Synthesis of Alkyl Xylosides: An Unexpected Effect of Amphiphilic Imidazolium Ionic Liquids

et al. 2018

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This manuscript presents results from the investigation on the synthesis of alkyl xylosides by the novel, very efficient and promising protocol of the Fischer synthesis from unprotected xylose and aliphatic alcohol. The use of 1‐alkyl‐3‐methylimidazolium hydrogen sulfate ionic liquids as the catalysts with dual functionality (surfactant + acid catalyst) and micellar reaction system are the main novelty of described method. It has been found that in developed method of the synthesis of alkyl xylosides the reaction of unprotected xylose with aliphatic alcohols carried out in mild reaction conditions and leads to alkyl xylosides with high yields. In progress analyses by Dynamic Light Scattering (DLS), High Performance Liquid Chromatography (HPLC) and Gas Chromatography (GC/MS) confirm the general postulated pathway of developed method.

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d-Xylose-based surfactants: Synthesis, characterization and molecular modeling studies

Cited by 7 publications

References 22 publications

β-Xylopyranosides: synthesis and applications

β-Xylopyranosides: synthesis and applications

d-Xylose and l-arabinose laurate esters: Enzymatic synthesis, characterization and physico-chemical properties

Micellar Route of the Synthesis of Alkyl Xylosides: An Unexpected Effect of Amphiphilic Imidazolium Ionic Liquids

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