2,5-Bis(hydroxymethyl)furan

2,5-Bis(hydroxymethyl)furan
Names
	IUPAC name [5-(hydroxymethyl)furan-2-yl]methanol
	Other names 2,5-furandimethanol, 2,5-bis(hydroxymethyl)furan, 2,5-di(hydroxymethyl)furan, 5-(hydroxymethyl)-furfuryl alcohol
Identifiers
CAS Number	1883-75-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:59984 ;
ChemSpider	67238 ;
ECHA InfoCard	100.015.950
PubChem CID	74663;
CompTox Dashboard (EPA)	DTXSID2062036 ;
	InChI InChI=1S/C6H8O3/c7-3-5-1-2-6(4-8)9-5/h1-2,7-8H,3-4H2 Key: DSLRVRBSNLHVBH-UHFFFAOYSA-N ;
	SMILES OCc1oc(cc1)CO;
Properties
Chemical formula	C6H8O3
Molar mass	128.127 g·mol−1
Appearance	white solid
Density	1.283 g/cm3
Melting point	74 to 77 °C (165 to 171 °F; 347 to 350 K)
Boiling point	275 °C (527 °F; 548 K)
Hazards
Flash point	120 °C (248 °F; 393 K)
Related compounds
Related furan-2-carbaldehydes	Furfural; Methoxymethylfurfural
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2,5-Bis(hydroxymethyl)furan (BHMF) is a heterocyclic organic compound, and is a derivative of a broader class of compounds known as furans. It is be produced from cellulose and has received attention as a biofeedstock.^[3] It is a white solid, although commercial samples can appear yellowish or tan.

Synthesis

2,5-BHF may be obtained from the reduction of the formyl group of 5-hydroxymethylfurfural (HMF). HMF is the product of acid-catalyzed dehydration of fructose. Fructose is both an isomer of and a derivative of glucose, which can be derived from the hydrolysis of cellulose. The reduction is catalyzed by nickel, copper chromite, platinum oxide, cobalt oxide, or molybdenum oxide, and sodium amalgam, under high temperatures and high hydrogen pressure.^[4]^[5] Hydrogenation in the presence of a copper or platinum catalyst in an aqueous environment gives 2,5-BHF as the main product. Under more forcing conditions, the furan ring is reduced as well, resulting in 2,5-bis(hydroxymethyl)tetrahydrofuran.^[4]

Applications

Functioning as a diol, 2,5-BHF has applications in the manufacture of polyurethane foams and polyesters.^[5]^[3]

References

^ http://www.chemblink.com/products/1883-75-6.htm
^ http://www.chemicalbook.com/ChemicalProductProperty_EN_CB4417778.htm
^ ^a ^b van Putten, R.-J., van der Waal, J. C., de Jong, E., Rasrendra, C. B., Heeres, H. J.,de Vries, J. G., "Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources", Chem. Rev. 2013, 113, 1499. doi:10.1021/cr300182k
^ ^a ^b Lewkowski, J. (2001). "Synthesis, chemistry and applications of 5-hydroxymethylfurfural and its derivatives". Arkivoc. 1: 17–54.
^ ^a ^b Tong, X., Ma, Y., Li, Y. (2010). "Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes". Applied Catalysis A: General. 285: 1–13. doi:10.1016/j.apcata.2010.06.049.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

2,5-bis(hydroxymethyl)furan

[1] ttp://www.chemblink.com/products/1883-75-6.htm

[2] ttp://www.chemicalbook.com/ChemicalProductProperty_EN_CB4417778.htm

[vanPtten-3] van Putten, R.-J., van der Waal, J. C., de Jong, E., Rasrendra, C. B., Heeres, H. J.,de Vries, J. G., "Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources", Chem. Rev. 2013, 113, 1499. doi:10.1021/cr300182k

[HMF_studies-4] Lewkowski, J. (2001). "Synthesis, chemistry and applications of 5-hydroxymethylfurfural and its derivatives". Arkivoc. 1: 17–54.

[HMF_derivs-5] Tong, X., Ma, Y., Li, Y. (2010). "Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes". Applied Catalysis A: General. 285: 1–13. doi:10.1016/j.apcata.2010.06.049.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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