Synthesis of Alkyl Polyglycosides From Glucose and Xylose for Biobased Surfactants: Synthesis, Properties, and Applications

Estrine, Boris; Marinković, Siniša; Jérôme, François

doi:10.1016/b978-0-12-812705-6.00011-3

Cited by 13 publications

(24 citation statements)

References 22 publications

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“…27−30 Isoamyl polypentoside (iC 5 Xyl), heptyl polyglucoside (C 7 Glu), and caprylyl/ capryl polyglycosides (C 8/10 Gly) passed the OECD 301F test with results up to 86%, 82%, and 98% of biodegradation over 28 days. 31−33 Furthermore, no dermatologic irritation for decyl and octadecyl glucoside (C 10 Glu, C 18 Glu) 28 and moderate ocular irritations (for C 8/10 Gly or iC 5 Xyl according to the OECD 405 test) 34 have been found, along with low health toxicity (LD 50 > 35 g/kg according to the OECD 401 test) for C 8/10 Glu 1.6 . 28 Eco-toxicity for aquatic organisms such as zooplankton and phytoplankton was found to be lower for APG surfactants as compared to C i E j , and, among the APGs, the branched ones are even less harmful than the linear ones.…”

Section: ■ Introductionmentioning

confidence: 99%

“…35 Finally, APGs are easily prepared from biobased resources, alcohols from fatty acids, and glucose or xylose from starch or hemicellulose. 34,36 Herein, we report the CA extraction from rosemary using five commercially available APGs, butyl glucoside (C 4 Glu), isoamyl polyxyloside (iC 5 Xyl), heptyl (C 7 Glu) and ethylhexyl (C 6,−2 Glu) polyglucosides, and caprylyl-capryl polyglycoside (C 8/10 Gly). Their ability to solubilize CA is also reported.…”

Section: ■ Introductionmentioning

confidence: 99%

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Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

Mazaud

Lebeuf

Pierlot

et al. 2021

ACS Sustainable Chem. Eng.

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Rosemary (Rosmarinus officinalis L.) is a Mediterranean herb known for its high antioxidant power that has been widely attributed to carnosic acid (CA). Passive extractions of CA have been performed in water by using five commercially available short-chain alkyl polyglycosides (APG) with alkyl chain lengths ranging from 4 to 10 carbon atoms and polar heads composed of pentoses and/or glucoses. APGs are nontoxic amphiphiles with high biodegradability. Their solubilizing capacity for CA has been determined, highlighting heptyl glucoside (C7Glu) as the most efficient one, followed by 2-ethylhexyl glucoside (C6,–2Glu) and isoamyl xyloside (iC5Xyl). However, iC5Xyl exhibited the highest selectivity toward CA solubilization as compared to ursolic acid (UA), a potential coextracted compound of rosemary leaves. In addition, it was found to be the most efficient amphiphile to extract CA from both ground and whole rosemary leaves. To optimize the maceration process and the recovery of the extract, a full factorial design 24 was performed investigating iC5Xyl concentration, temperature, stirring, and extraction time. A high concentration of hydrotrope was found to be the most important condition to optimize the maceration step, while the temperature particularly increases the yield, but in detriment of the CA content in the final dried extract.

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Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

Mazaud

Lebeuf

Pierlot

et al. 2021

ACS Sustainable Chem. Eng.

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“…The industrial‐scale production of carbohydrate‐based surfactants is relatively recent (Gutsche & Behler, 1999; Lang, 2002). Commercially produced carbohydrate‐derived surfactants include sucrose esters and fatty alcohol polyglycosides, also called APGs (Estrine et al, 2019; Lichtenthaler, 2007; Spitzer, 2021; Von Rybinski, 2001). Other commercially important carbohydrate‐based surfactants are synthesized from glucose derivatives.…”

Section: Building Blocks and Chemicals Derived From Carbohydratesmentioning

confidence: 99%

“…APGs began their commercial production around 1992 (Estrine et al, 2019; von Rybinski & Hill, 1998). These biomass‐derived surfactants reduce interfacial tension with the advantage that the hydration of the polar head made up of glucose units is less affected by temperature changes than common nonionic surfactants (Nickel et al, 1996).…”

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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“…The fine control of temperature, time and molar ratio of sugar to alcohol, could tune the . Whereas the preparation of APGs with a of more than 2 remains to date a huge challenge 17,[27][28][29] , the proposed method could expand the molar mass and maintain complete glycosylation of the sugars at the same time. The distillation of water along with propargyl alcohol in step 2, resulted to be the key-step for the oligomerization.…”

confidence: 99%

Sequential acid-catalyzed alkyl glycosylation and oligomerization of unprotected carbohydrates

et al. 2021

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Synthesis of Alkyl Polyglycosides From Glucose and Xylose for Biobased Surfactants: Synthesis, Properties, and Applications

Cited by 13 publications

References 22 publications

Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

Amyl Xyloside, a Selective Sugar-Based Hydrotrope for the Aqueous Extraction of Carnosic Acid from Rosemary

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

Sequential acid-catalyzed alkyl glycosylation and oligomerization of unprotected carbohydrates

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