Hydroxymethylfurfural

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Hydroxymethylfurfural
IUPAC name	5-(hydroxymethyl)-2-furaldehyde
Identifiers
CAS number	[67-47-0]
SMILES	O=Cc1ccc(CO)o1
Properties
Molecular formula	C6H6O3
Molar mass	126.11 g/mol
Density	1.29 g/cm³
Melting point	30 - 34 °C
Boiling point	114 - 116 °C (1 mbar)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Hydroxymethylfurfural, HMF or 5-(Hydroxymethyl)furfural is an aldehyde and a furan compound formed during the thermal decomposition of sugars and carbohydrates.^[1] HMF has been identified in a wide variety of heat processed foods including milk, fruit juices, spirits, honey, etc. Recent studies proved HMF is also found in cigarettes.

Contents 1 Production 2 Uses 3 History 4 References

[edit] Production

Just like the production of furfural, HMF can be produced from biomass.

In 2006 a researcher from University of Wisconsin-Madison discovered a new way of producing HMF from fructose:^[2][3]

In this new method, fructose is reacted with hydrochloric acid in an aqueous phase and the formed HMF (very water-soluble) is then continuously extracted into Methyl isobutyl ketone as an organic phase at 180 °C. The water phase is modified with DMSO and PVP, reducing the amount of side product to a minimum. The organic phase is modified with 2-butanol in order to improve the amount of HMF in the organic phase. In an optimized system for fructose (but not raw biomass), conversion is 77% with half the HMF ending up in the organic phase. Removing the (high boiling) solvents remains an issue.

In the image above are displayed in a series of chemical equilibria: fructopyranose 1, fructofuranose 2, two intermediate stages of dehydration (not isolated) 3,4 and finally HMF 5.

In June 2007, researchers at Pacific Northwest National Laboratory discovered an inexpensive process (using chromium chloride as catalyst) to directly convert both fructose (yielding 90%+) and glucose (yielding 70%+) into an HMF, leaving very little residual impurities.^[4] This discovery has great relevance for the manufacturing of plastics and synthetic fuels directly from biomass, since glucose can be derived directly from starch and cellulose, both widely available in nature.^[5]

[edit] Uses

HMF is identified as a biofuel with great potential.^{[citation needed]} Organic oxidation of this compound also gives 2,5-furandicarboxylic acid which may replace terephthalic acid as a monomer in the production of plastics.

5-HMF is under investigation as a treatment for sickle cell disease.^{[citation needed]}

[edit] History

This organic compound was studied by French chemist Louis Maillard in 1912 while doing research about non-enzymatic reactions from glucose and lysine.

[edit] References

1. ^ HMF, hydroxy-methyl-furfural. hydroxy-methyl-furfural. Retrieved on September 10, 2005.
2. ^ terradaily.com News Article
3. ^ Yuriy Román-Leshkov, Juben N. Chheda, James A. Dumesic (2006). "Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose". Science 312 (5782): 1933 - 1937. doi:10.1126/science.1126337. 
4. ^ Pacific Northwest National Laboratory (2007-06-14). "Plastic that grows on trees". Press release.
5. ^ MIT Technology Review