Hydroxymethylfurfural

Chembox new
Name = Hydroxymethylfurfural
ImageFile = Hydroxymethylfurfural.png ImageSize = 200px
ImageName = Hydroxymethylfurfural
IUPACName = 5-(hydroxymethyl)-2-furaldehyde
Section1 = Chembox Identifiers
CASNo = 67-47-0
SMILES = O=Cc1ccc(CO)o1
Section2 = Chembox Properties
Formula = C₆H₆O₃
MolarMass = 126.11 g/mol
Density = 1.29 g/cm³
MeltingPt = 30 - 34 °C
BoilingPt = 114 - 116 °C (1 mbar)

Hydroxymethylfurfural, HMF or 5-(Hydroxymethyl)furfural is an aldehyde and a furan compound formed during the thermal decomposition of sugars and carbohydrates. [cite web|title=HMF, hydroxy-methyl-furfural|work=hydroxy-methyl-furfural
url=http://www.xs4all.nl/~jtemp/hmf.html|accessmonthday=September 10 |accessyear=2005] 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.

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: [terradaily.com [http://www.terradaily.com/reports/New_Process_Makes_Diesel_Fuel_And_Industrial_Chemicals_From_Simple_Sugar_999.html News Article] ] [cite journal | title = Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose | author = Yuriy Román-Leshkov, Juben N. Chheda, James A. Dumesic | journal = Science | year = 2006 | volume = 312 | issue = 5782 | pages = 1933–1937 | doi = 10.1126/science.1126337 | pmid = 16809536]

:

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. [cite press release | publisher = Pacific Northwest National Laboratory | url = http://www.pnl.gov/news/release.asp?id=255 | title = Plastic that grows on trees | date = 2007-06-14 ] [cite journal | title = Metal Chlorides in Ionic LiquidSolvents Convert Sugars to 5-Hydroxymethylfurfural | author = Haibo Zhao, Johnathan E. Holladay, Heather Brown, Z. Conrad Zhang | journal = Science | year = 2007 | volume = 316 | issue = 5782 | pages = 1597–1600 | doi = 10.1126/science.1141199 | pmid = 17569858] 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. [ [http://www.technologyreview.com/Nanotech/18943/ MIT Technology Review] ]

Uses

HMF is identified as a biofuel with great potential.Fact|date=June 2008 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.Fact|date=June 2008

History

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

References