10332. Ethoxymethylfurfural

Nomenclature

CAS number: 1917-65-3
5-(Ethoxymethyl)-2-furancarboxaldehyde; 5-(ethoxymethyl)-2-furaldehyde; 2-formyl-5-ethoxymethylfuran; ω-ethoxymethylfurfuraldehyde; EMF.
C8H10O3; mol wt 154.16.
C 62.33%, H 6.54%, O 31.14%.

Description and references

Naturally occurring aroma component of fortified wines. High energy organic liquid; prototype of the biofuels known as “furanics”. Prepn from ω-bromomethylfurfuraldehyde: W. F. Cooper, W. H. Nuttall, J. Chem. Soc. Trans. 99, 1193 (1911) DOI. Identification in port wine: R. F. Simpson, J. Sci. Food Agric. 31, 214 (1980) DOI. Quantification in sweet fortified wines: I. Cutazch et al., J. Agric. Food Chem. 47, 2837 (1999) DOI PubMed. Prepn via dehydration of fructose: D. W. Brown et al., J. Chem. Technol. Biotechnol. 32, 920 (1982). Prepn from glucose-containing starting material and use as biofuel: G. J. M. Gruter, F. Dautzenberg, EP 1834950 (2007 to Avantium). Direct prepn from cellulose: M. Mascal, E. B. Nikitin, Angew. Chem. Int. Ed. 47, 7924 (2008) DOI.

Chemical structure

Properties

Yellow oil. bp 235-240°; bp35 145°. d15.515.5 1.1096. Energy density: 8.7 kWh/l. Readily sol in usual organic solvents. Sol in hot petroleum; insol in cold. Moderately sol in water.

Use

Alternative fuel.