27836-64-2

Usage

InChI:InChI=1/C18H36O6/c1-2-3-4-5-6-7-8-9-10-11-12-23-18-17(22)16(21)15(20)14(13-19)24-18/h14-22H,2-13H2,1H3

Synthetic route

D-Glucose (2280-44-6) + 1-dodecyl alcohol (112-53-8) → dodecyl β-D-glucopyranoside (27836-64-2)

Conditions	Yield
With Adipic acid; choline chloride at 80 - 95℃; Reagent/catalyst; Inert atmosphere; Green chemistry;	76%
	6%
With sulfuric acid; silica gel at 65℃; for 8h; Fischer glycosylation;

Upstream product

• 2280-44-6 D-Glucose 
• 112-53-8 1-dodecyl alcohol 
• 9004-34-6 cellulose 
• 9004-34-6 microcrystalline cellulose 
• 50-99-7 D-glucose 

Downstream Products

• 258349-79-0 n-dodecyl 4,6-O-benzylidene-β-D-glucopyranoside 

Relevant academic research and scientific papers

High Catalytic Performance of Aquivion PFSA, a Reusable Solid Perfluorosulfonic Acid Polymer, in the Biphasic Glycosylation of Glucose with Fatty Alcohols

The catalytic performance of Aquivion PFSA, a solid superacid, was investigated in the catalytic glycosylation of glucose with fatty alcohols. Four main criteria were considered to evaluate the catalytic performance of Aquivion PFSA: (1) the selectivity of the reaction, (2) the turnover frequency, (3) the reactor productivity, and (4) the catalyst stability/recycling. To shed light on the catalytic performance of Aquivion PFSA, it was systematically compared to H2SO4, which is industrially employed in such reactions. We discovered that Aquivion PFSA surpassed the catalytic performance of H2SO4 in terms of activity, selectivity, and reactor productivity. In particular, Aquivion PFSA selectively converted glucose to alkyl polyglucosides (DP = 1.2) with 85% yield, which corresponded to a reactor productivity as high as 477 kg/(m3 h). Conversely to H2SO4, Aquivion PFSA was also capable of selectively producing alkyl polyglucosides directly from glucose syrup, a cheap source of glucose. This result was ascribed to the amphiphilic nature of Aquivion PFSA, which facilitated the Pickering-like emulsification of the biphasic reaction medium. Finally, owing to its high chemical and mechanical properties, Aquivion PFSA was highly stable under our working conditions and could be recycled at least 10 times without obvious loss of its catalytic performance.

Micellar effect on the direct Fischer synthesis of alkyl glucosides

This manuscript presents results from the investigation on the synthesis of alkyl glucosides by the novel, very efficient and environmentally friendly protocol of the Fischer-type synthesis from unprotected glucose and aliphatic alcohols. The use of the dual functionality catalysts (surfactant?+?acid catalyst) and micellar reaction system are the main novelty of described method. It has been found, that in developed method of synthesis the reaction of unprotected glucose with aliphatic alcohols carried out with significantly different route, than the normal (classical) route and leads to alkyl glucopyranoside derivatives with high yields. In progress analyses by DLS, HPLC and GC/MS confirm the general postulated pathway of developed method.

Conversion of Cellulose into Amphiphilic Alkyl Glycosides Catalyzed by Aquivion, a Perfluorosulfonic Acid Polymer

The perfluorosulfonic acid (PFSA) Aquivion PW98 is an amphiphilic solid superacid which is shown to catalyze the conversion of cellulose into amphiphilic alkyl glycosides (AAGs) in 85 % yield (with 97 % selectivity). The process involves a mechanocatalytic depolymerization of cellulose followed by a direct glycosylation with n-dodecanol. In comparison to H2SO4 and solid acid catalysts commonly employed in cellulose processing, Aquivion PFSA PW98 is not only recyclable but also exhibits superior catalytic performances in terms of yield, selectivity, and reactor productivity.

Preparation and surface activity of phosphated alkyl oligoglucosides

A family of phosphated alkyl oligoglucoside surfactants was prepared by reacting alkyl oligoglucosides with phosphorus oxychloride. The alkyl oligoglucosides were obtained by an usual method in which the glucose is reacted with a fatty alcohol containing 10-18 carbon atoms. These novel phosphated surfactants have been found to exhibit good surface tension, foaming and wetting power. The critical micelle concentration was found to increase with the length of hydrocarbon chain of the surfactant. The surface excess concentration and the interfacial area per surfactant molecule are reported. These phosphated surfactants also exhibit a good performance to improve the whiteness and wetting of cotton fabrics in a hydrogen oxide bleaching system, and they are also found to be more biodegradable than conventional surfactants. AOCS 2010.

Method for preparing alkyl glycoside

The invention provides a method for preparing alkyl glycoside. The method comprises the following steps: providing a deep-eutectic solvent as a catalyst, wherein the deep-eutectic solvent consists ofcholine chloride and hydrogen-bond donors, and the structural formula of the choline chloride is shown as the formula (I) in the original specification; performing a reaction on the deep-eutectic solvent, glucose and fatty alcohol, so as to generate the alkyl glycoside, wherein the molar ratio of the choline chloride and the hydrogen-bond donors is 1: 1. Therefore, by utilizing the characteristicsof the deep-eutectic solvent of being uneasy in volatilization and combustion, good in heat stability and solubility, easy in recovery, repeatable in use and the like, the reaction is performed on the deep-eutectic solvent, the glucose and the fatty alcohol to generate the alkyl glycoside, the utilization rate of atoms in a synthesis process is as high as 100%, and the alkyl glycoside is low in toxicity and is biodegradable.

Method for preparing alkyl polyglycoside through concerted catalysis of ionic liquid compounding system

The invention belongs to a preparation method of alkyl polyglycoside, and particularly relates to a method for preparing the alkyl polyglycoside through concerted catalysis of an ionic liquid compounding system. According to the method disclosed by the invention, ionic liquid with catalytic activity is compounded with one or two of sulphuric acid, phosphoric acid, p-toluene sulfonic acid and dodecylbenzene sulfonic acid so that a novel catalysis system is formed, and the alkyl polyglycoside is prepared through the concerted catalysis of the novel catalysis system. The technology of the method disclosed by the invention has the advantages that the reaction efficiency of a unit catalyst is high and the reaction time is short.

Efficient production and separation of biodegradable surfactants from cellulose in 1-butyl-3-methylimidazolium chloride

Alkyl glycoside biodegradable surfactants were produced from cellulose and 1-octanol or 1-dodecanol in a one-pot, two-step (hydrolysis-glycosidation) process in 1-butyl-3-methylimidazolium chloride. Both surfactant productivity and separation efficiencies have been strikingly enhanced compared to other previously reported ionic liquid processes. Production temperatures were decreased to limit the extent of glucose dehydration and further degradation processes, but the conversions remained high. Surfactant molar yields up to 72% were achieved by operating at 70°C. Several separation procedures were tested to achieve high recoveries of both surfactant and ionic liquid. The use of a silica stationary phase was useful for isolation of the surfactant, whereas crystallization of the ionic liquid improved its separation efficiency. Finally, the precipitation of dodecyl glycosides in aqueous media was highly efficient for their isolation and for the recovery (> 99 %) of the ionic liquid by using only water as the solvent for separation.

Transformation of cellulose into biodegradable alkyl glycosides by following two different chemical routes

The transformation of cellulose into long-chain alkyl glycoside surfactants has been carried out following two different routes: (1) Direct transformation of cellulose to butyl-, hexyl-, octyl-, decyl- and dodecyl-α,β- glycosides in an ionic liquid media and Amberlyst-15Dry as catalysts, with mass yield of up to 82%; and (2) two steps reaction with transformation of cellulose into methyl glucosides, with a procedure described by Zhang et al., followed by transacetalation with 1-octanol and 1-decanol in the presence of Amberlyst-15Dry. A kinetic study for the direct transformation of cellulose using 1-octanol has shown that depolymerisation of cellulose continues during the Fischer glycosidation. Increasing the chain length of the alcohol decreases the global reaction rate owing to an increase in the lipophilicity of the alcohol that decreases its contact with the carbohydrates. Finally, several acid catalysts were tested and the best results were obtained with Amberlyst-15Dry.

Medicament comprising a reducing alkyl-sugar monomer for the treatment of inflammatory disorders

The invention relates to a medicament comprising at least one reducing alkyl-sugar monomer having a hydroxyl function which is substituted by an alkoxy radical at C2-C40, said medicament being preferably intended to regulate inflammatory mechanisms. The reducing sugar is preferably selected from the group containing rhamnose, fucose and glucose. The invention also relates to a cosmetic treatment method involving the topical application of a composition comprising at least one reducing alkyl-sugar monomer having a hydroxyl function which is substituted by an alkoxy radical at C2-C40.

Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation

Fischer glycosylation, a widely used technique for the preparation of simple alkyl or aryl glycosides, has a few drawbacks including the use of strong mineral acids, excess alcohols, high temperature and long reaction times. This manuscript highlights a modification using sulfuric acid immobilized on silica as catalyst for the preparation of glycosides from free sugars such as d-glucose, d-galactose, d-mannose, l-rhamnose, l-fucose, N-acetyl-d-glucosamine and d-maltose with a diverse range of alcohols to afford a series of useful sugar derivatives in good to excellent yields.