Oleic Acid Based Cyclodextrins for the Development of New Hydrosoluble Amphiphilic Compounds

Abstract

A new family of amphiphilic cyclodextrins produced from oleic acid derivatives and maleic anhydride is described. These amphiphilic cyclodextrins are synthesized in two steps. The first step is the alkenylation of maleic anhydride by oleic acid derivatives to produce the oleic succinic anhydrides. The second step is the grafting of the oleic succinic anhydrides on various cyclodextrins. A self‐inclusion of the alkyl chain or an inclusion of one alkyl chain in the cavity of another CD is showed by NMR experiments. The twelve amphiphilic cyclodextrins described possess high solubility in water (50–500 g/L at 20 °C) and low critical aggregation concentration (16–360 mg/L).

Highly Water‐Soluble Amphiphilic Cyclodextrins Bearing Branched and Cyclic Oleic Grafts

“…This result confirmed that a rhodium catalyst was necessary to produce the cyclic anhydrides. For comparison, the entries 5 and 6 recalled our already published branched anhydrides obtained by thermic way . The two results showed that higher temperature (220 °C vs. 140 °C) was necessary to produce a higher quantity of branched products in a shorter time.…”

“…The second step of the synthetic pathway is the grafting of the unsaturated or saturated BSA/CSA mixture on β‐CD. This step was performed as described for the syntheses of amphiphilic β‐CD esters of alkenyl succinic acids published mainly by the group of de Rossi and others groups , . The reaction was done in pyridine with 2 molar equivalents of the anhydride functions of the BSA/CSA mixture with respect to β‐CD and allowed to produce various oleic succinyl‐β‐CDs (Scheme and Table ).…”

“…Note that the CSA was not obtained without the use of a catalyst. In this context, we recently published the synthesis of new amphiphilic oleic succinyl‐cyclodextrins obtained by esterification of various cyclodextrins (CDs) with branched oleic succinic anhydrides made from oleic acid or its methyl ester by thermic maleinisation . In this publication, the aim was to synthesize oleic succinic anhydrides by using various amounts of rhodium catalyst to access different ratios of cyclic to branched products.…”

Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins

“…OS-CDs synthesis was conducted in two steps as previously reported by our group [31,32]. The first step involved the alkenylation of maleic anhydride by methyl oleate and oleic acid, leading to the formation of maleinised methyl oleate or maleinised oleic acid, respectively.…”

Synthetic Application of Cyclodextrins in Combination with Metal Ions, Complexes, and Metal Particles

“…Hydrogenation of 2-methylbut-3-en-2-ol gave the corresponding saturated alcohol with full conversion and 100 % selectivity with stable activity in three runs ( Recently, the synthesis of new amphiphilic oleic acid based cyclodextrin materials was reported by reacting CDs with oleic succinic anhydride. [41] These amphiphilic preparations are highly water-soluble and have low surface tension and low criticalaggregation concentration. Of these products, 15-βCD with a substitution degree of 1.6 was used to stabilize ruthenium nanoparticles (2.56 � 0.60 nm) by reducing Ru(NO)(NO 3 ) 3 and 15-βCD (1 : 3 ratio) with NaBH 4 and applying the resulting catalyst in hydrogenations.…”