Hydroxymethylfurfural

Hydroxymethylfurfural (HMF), also 5-(Hydroxymethyl)furfural, is an organic compound derived from dehydration of certain sugars. This yellow low-melting solid is highly water-soluble. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups. HMF has been identified in a wide variety of baked goods. HMF, which is derived from hexoses, is a potential "carbon-neutral" feedstock for fuels and chemicals.

Production and reactions

Related to the production of furfural, HMF is produced from sugars. It arises via the dehydration of fructose. Treatment of fructose with acids followed by liquid-liquid extraction into organic solvents such as methyl isobutyl ketone. The conversion is affected by various additives such as DMSO, 2-butanol, and polyvinyl pyrrolidone, which minimize the formation of side product. Ionic liquids facilitate the conversion of fructose to HMF. When hexoses are hydrolyzed with hydrochloric acid, 5-chloromethylfurfural is produced instead of HMF.