583-33-5

Usage

InChI:InChI=1/C9H12O3/c1-2-3-6-12-9(10)8-5-4-7-11-8/h4-5,7H,2-3,6H2,1H3

Upstream product

• 526-99-8 meso-galactaric acid 
• 71-36-3 butan-1-ol 
• 98-01-1 furfural 
• 56-23-5 tetrachloromethane 
• 555-31-7 aluminum isopropoxide 
• 123-72-8 butyraldehyde 
• 1829-09-0 2-furancarboxaldehyde dibutyl acetal 

Downstream Products

• 83867-83-8 butyl (+/-)-tetrahydrofuran-2-carboxylate 
• 4282-32-0 furan-2,5-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

A unique pathway to platform chemicals: Aldaric acids as stable intermediates for the synthesis of furandicarboxylic acid esters

2,5-Furandicarboxylic acid (FDCA) has received attention as an emerging bio-based building block with many applications, especially in renewable polyesters. The common route to FDCA uses the unstable 5-hydroxymethylfurfural (HMF) as an intermediate. Here, we present an alternative route to FDCA and its esters using C6 aldaric acids as stable intermediates. Aldaric acids, or sugar diacids, can be obtained by the oxidation of C6 sugars or uronic acids from pectin. Subsequent dehydration of aldaric acids by solid acid catalysts in butanol produces furancarboxylates. Using silica-supported acid catalysts, over 90% yields of furancarboxylates were achieved with the selectivity to FDCA and its esters reaching 80%.

METHOD OF PRODUCING FURAN CARBOXYLATES FROM ALDARIC ACIDS BY USING SOLID HETEROGENEOUS CATALYSTS

According to an example aspect of the present invention, there is provided a method of producing furan carboxylates from aldaric acids in the presence of a solid heterogeneous catalyst and a solvent with short reaction time. The feedstock for the production is a stable compound, which allows industrial scaling of the process. Solid acid catalyst and sustainable solvent provide considerable reduction of toxic waste compared to traditional methods, and recyclability.

Action of boron trifluoride etherate and stannic chloride on heterocyclic aromatic acetals

Twelve heterocyclic aromatic acetals (1a-12a) have been synthesised and their reactions with Lewis acids, viz. boron trifluoride etherate (BTE) and stannic chloride (STC) have been studied.The acetals yield ethers, esters and aldehydes with BTE, but only esters and aldehydes with STC.Interestingly, pyridine-2-aldehyde acetal (12a), yields aldehyde alone, that too in low yield.Probable mechanisms have been suggested for the product formation.