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.
furan.svg)
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| Names | |
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| 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)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.015.950 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
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Furfural Methoxymethylfurfural |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
edit2,5-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
editFunctioning as a diol, 2,5-BHF has applications in the manufacture of polyurethane foams and polyesters.[3][5]
References
edit- ^ "2,5-Furandimethanol [1883-75-6]".
- ^ "2,5-Furandimethanol".
- ^ 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): 1499–1997. doi:10.1021/cr300182k. PMID 23394139.
- ^ a b Lewkowski, J. (2001). "Synthesis, chemistry and applications of 5-hydroxymethylfurfural and its derivatives". Arkivoc. 1: 17–54. doi:10.3998/ark.5550190.0002.102. hdl:2027/spo.5550190.0002.102.
- ^ 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 (1–2): 1–13. doi:10.1016/j.apcata.2010.06.049.