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

Abstract

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.

Surface active fatty acid ILs: Influence of the hydrophobic tail and/or the imidazolium hydroxyl functionalization on aggregates formation

“…Therefore, understanding the micellization behavior of ILs in aqueous solution is a vital part of predicting, controlling, and designing their properties and finally their applications. In this regard, the IL micellar systems were studied in various areas such as nanomaterials formation [29], organic synthesis [30], micellar catalysis [31], micellar extraction [32,33], drug delivery [34], and antimicrobial activity [25,35].…”

Micellar Catalysis in Fischer Glycosidation: En Route to Diverse Functional Glycosides

“…“Classic” route of Fischer reaction, beside the main product, also gives glucose oligomerization products (n>1, Scheme , route 1 ). Micellar route allows to obtain more chemically pure products, where oligomers are not observed (n =1, Scheme , route 1 ) . This phenomenon may be significant for many applications requiring the use of pure glycosides, e. g. in biochemistry .…”

“…As a very interesting effect can be recognized the lack of glucofuranoside anomers, which in „classical” Fischer reaction is commonly formed in the amounts of 3–5%wt. Similar phenomenon was observed in the reaction of glucose and xylose with aliphatic alcohols carried out in the micellar reaction system . It is well known, that the relative proportion of glucopyranosides to the glucofuranosides depends on the reaction conditions, also on the character of used catalyst.…”

A density functional theory study on the water aggregation behaviour of fatty acid-based anionic surface active ionic liquids

“…Nowadays, the water aggregation or micellization properties of SAILs are actively studied by both experimental and theoretical studies [38,49,50]. Experimentally, surface tension, conductivity, steady state uorescence spectra, viscosity, and dynamic light scattering measurements are used to determine the water aggregation properties of SAILs.…”