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2,5-Bis(hydroxymethyl)furan

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2,5-Bis(hydroxymethyl)furan
2,5-BHF molecule
Names
Preferred IUPAC name
(Furan-2,5-diyl)dimethanol
Other names
Furan-2,5-diyldimethanol
[5-(hydroxymethyl)furan-2-yl]methanol
2,5-Furandimethanol
2,5-Bis(hydroxymethyl)furan
2,5-Di(hydroxymethyl)furan
5-(Hydroxymethyl)-furfuryl alcohol[1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.015.950 Edit this at Wikidata
  • InChI=1S/C6H8O3/c7-3-5-1-2-6(4-8)9-5/h1-2,7-8H,3-4H2 checkY
    Key: DSLRVRBSNLHVBH-UHFFFAOYSA-N checkY
  • OCc1oc(cc1)CO
Properties
C6H8O3
Molar mass 128.127 g·mol−1
Appearance white solid[2]
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 furans
 Furfural
Methoxymethylfurfural
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 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-BHMF 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-BHMF 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.[3][5]

References

  1. ^ "2,5-Furandimethanol [1883-75-6]".
  2. ^ "2,5-Furandimethanol".
  3. ^ a b Van Putten, Robert-Jan; Van Der Waal, Jan C; De Jong, Ed; Rasrendra, Carolus B; Heeres, Hero J; De Vries, Johannes G (2013). "Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources". Chemical Reviews. 113 (3): 1499. doi:10.1021/cr300182k. PMID 23394139.
  4. ^ a b Lewkowski, J. (2001). "Synthesis, chemistry and applications of 5-hydroxymethylfurfural and its derivatives". Arkivoc. 1: 17–54.
  5. ^ 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.
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