138052-46-7

Upstream product

• 67-56-1 methanol 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 50-99-7 D-glucose 
• 9004-34-6 cellulose 

Relevant academic research and scientific papers

Kinetic analysis of hexose conversion to methyl lactate by Sn-Beta: Effects of substrate masking and of water

Simple sugars show promise as substrates for the formation of fuels and chemicals using heterogeneous catalysts in alcoholic solvents. Sn-Beta is a particularly well-suited catalyst for the cleavage, isomerization and dehydration of sugars into more valuable chemicals. In order to understand these processes and save resources and time by optimising them, kinetic and mechanistic analyses are helpful. Herein, we study substrate entry into the Sn-Beta-catalysed methyl lactate process using abundant hexose substrates. NMR spectroscopy is applied to show that the formation of methyl lactate occurs in two kinetic regimes for fructose, glucose and sucrose. The majority of methyl lactate is not formed from the substrate directly, but from methyl fructosides in a slow regime. At 160 °C, more than 40% of substrate carbon are masked (i.e. reversibly protected in situ) as methyl fructosides within a few minutes when using hydrothermally synthesised Sn-Beta, while more than 60% methyl fructosides can be produced within a few minutes using post-synthetically treated Sn-Beta. A significant fraction of the substrate is thus masked by rapid methyl fructoside formation prior to subsequent slow release of fructose. This release is the rate-limiting step in the Sn-Beta-catalysed methyl lactate process, but it can be accelerated by the addition of small amounts of water at the expense of the maximum methyl lactate yield.

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.

High-yielding one-step conversion of D-glucose and D-galactose to the corresponding α and β methyl-D-glucofuranosides and galactofuranosides

D-Glucose and D-Galactose are transformed to the corresponding α and β-Methyl D-Glucofuranosides in good yields using methanol and Ferric chloride as catalyst.

A NEW, FACILE METHOD FOR CLEAVAGE OF ACETALS AND DITHIOACETALS IN CARBOHYDRATE DERIVATIVES

Treatment of carbohydrate acetals and dithioacetals with a dilute solution of iodine in methanol provides a simple, convenient, and high-yielding process for cleavage of the acetal functions.