2,5-Bis(hydroxymethyl)furan

changed changed 477211391 2,5-Bis(hydroxymethyl)furan.svg 220px 2,5-BHF-3D-balls.png 220 2,5-BHF molecule (Furan-2,5-diyl)dimethanol Furan-2,5-diyldimethanol[5-(hydroxymethyl)furan-2-yl]methanol2,5-Furandimethanol2,5-Bis(hydroxymethyl)furan2,5-Di(hydroxymethyl)furan5-(Hydroxymethyl)-furfuryl alcohol http://www.chemblink.com/products/1883-75-6.htm 2,5-Furandimethanol [1883-75-6] 2010-12-19 2019-07-22 https://web.archive.org/web/20190722145910/https://www.chemblink.com/products/1883-75-6.htm dead changed ?? 1883-75-6 correct FDA 4XE4JYN4G7 74663 correct chemspider 67238 correct EBI 59984 OCc1oc(cc1)CO correct chemspider 1S/C6H8O3/c7-3-5-1-2-6(4-8)9-5/h1-2,7-8H,3-4H2 correct chemspider DSLRVRBSNLHVBH-UHFFFAOYSA-N 6 8 3 white solid http://www.chemicalbook.com/ChemicalProductProperty_EN_CB4417778.htm 2,5-Furandimethanol 1.283 g/cm3 74 to 77 275 120 furans FurfuralMethoxymethylfurfural 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. 10.1021/cr300182k 23394139 Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources Chemical Reviews 113 3 1499–1997 2013 Van Putten Robert-Jan Van Der Waal Jan C De Jong Ed Rasrendra Carolus B Heeres Hero J De Vries Johannes G https://research.rug.nl/en/publications/ba586fda-9b33-4e7c-9701-2d3d3cf6cd93 11370/ba586fda-9b33-4e7c-9701-2d3d3cf6cd93 free 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. Lewkowski, J. Synthesis, chemistry and applications of 5-hydroxymethylfurfural and its derivatives Arkivoc 2001 1 17–54 10.3998/ark.5550190.0002.102 2027/spo.5550190.0002.102 free Tong, X. Ma, Y. Li, Y. Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes Applied Catalysis A: General 2010 285 1–2 1–13 10.1016/j.apcata.2010.06.049 2010AppCA.385....1T free 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. Applications Functioning as a diol, 2,5-BHF has applications in the manufacture of polyurethane foams and polyesters. References Category:Furans Category:Diols