Synthesis, physico-chemical properties and complexing abilities of new amphiphilic ligands from d-galacturonic acid

Allam, Anas; Behr, Jean‐Bernard; Dupont, Laurent; Nardello‐Rataj, Véronique; Plantier‐Royon, Richard

doi:10.1016/j.carres.2010.01.009

Cited by 15 publications

(11 citation statements)

References 70 publications

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“…Concerning other sugars than glucose, some glycamides have been obtained from glyconolactones like for the synthesis of copper-chelating macrocycles, − glycosylglycerolipid derivatives, and hepatoprotective hydrazines . With regard to the surfactant applications, Benvegnu et al have recently described the synthesis of bolaamphiphiles and guluronamides from polyguluronic acid or alginates …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

Lebeuf

Liu

Pierlot

et al. 2018

ACS Sustainable Chem. Eng.

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A series of 13 well-defined alkylglucuronamides [AGUA] surfactants with hydrophobic chains consisting of fatty alcohols (C8, C12, or C16) involved in a glucosidic bond has been synthesized in two steps from glucuronic acid or glucuronolactone. The nonionic polar heads are a sugar unit with an amide function derived from five different amines, i.e., methylamine, ammonia, ethanolamine, ethoxyethanolamine, and aminopropanediol. Their CMC values present variations from 0.03 to 29 mM, and their hydrophilic/lipophilic behaviors have been compared to conventional dodecyl polyethoxylated surfactants (C12E j ) using the PIT-slope methodology. They cover a large scale of the corresponding C12E j with j varying from 5 to 8. Regarding functional properties, the novel alkylglucuronamides exhibit good foaming properties. Last but not least, two of them could be classified as easily biodegradable according to respirometric tests.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

Lebeuf

Liu

Pierlot

et al. 2018

ACS Sustainable Chem. Eng.

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“…Glucuronic acids or their lactone derivatives are useful resources for the preparation of carbohydrate esters, by reaction with fatty alcohols. Both chemical and enzymatic procedures towards amphiphilic glucuronates have been reported (Figure 18) [148][149][150][151][152][153][154][155][156]. Though very close in structure compared to acylated sugars, this change in the OCOR vs COOR linkage has some influence on the properties [157].…”

Section: Glycosidesmentioning

confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

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GLOSSARY Carbohydrates are a family of biomolecules, ubiquitous in Nature, based on a common polyhydoxylated backbone though varying in size (from small molecules to macromolecules), in fine structure (configuration and functionalization), and possessing a wide range of biological properties and roles making them indispensable to life. Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups. Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension. Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, terpenes. DEFINITION OF THE SUBJECT Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life, and must therefore be improved constantly in terms of environmental impact, sustainability and performance. One way towards more sustainable surfactants is the use of renewable resources as raw materials for their manufacture, in place of fossil ones. Since the structure of surfactant combines a polar part to a hydrophobic one, carbohydrates, which are very polar molecules, appear as ideal candidates for serving as renewable building blocks in the synthesis of bio-based surfactants. Developed first with the aim of providing added-value to some agricultural crops and by products, this strategy shows nowadays a rebirth in the context of green and sustainable chemistry. The chapter illustrates, from the chemical point of view, the diversity of molecular structures which belong to the family of carbohydrate-based surfactants.

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“…Plantier-Royon and co-workers [64] developed new applications for GalA, envisioning taking advantage of the polyfunctional character of GalA and using it as a scaffold for the synthesis of new amphiphilic metal ligands. Among these, they efficiently synthesized new complexing surfactants from GalA and n-octanol as renewable raw materials in a two-step sequence.…”

Section: Synthesis Of Biologically and Pharmacological Active Compoundsmentioning

confidence: 99%