2,5-Bis(hydroxymethyl)furan (BHMF) is a heterocyclicorganic 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.
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]
^ abVan 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.
^ abLewkowski, 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.
^ abTong, 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.
January 01, 1970
hydroxymethyl, furan, bhmf, heterocyclic, organic, compound, derivative, broader, class, compounds, known, furans, produced, from, cellulose, received, attention, biofeedstock, white, solid, although, commercial, samples, appear, yellowish, names, preferred, i. 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 2 5 Bis hydroxymethyl furan Names Preferred IUPAC name Furan 2 5 diyl dimethanol Other names Furan 2 5 diyldimethanol 5 hydroxymethyl furan 2 yl methanol2 5 Furandimethanol2 5 Bis hydroxymethyl furan2 5 Di hydroxymethyl furan5 Hydroxymethyl furfuryl alcohol 1 Identifiers CAS Number 1883 75 6 N 3D model JSmol Interactive image ChEBI CHEBI 59984 Y ChemSpider 67238 Y ECHA InfoCard 100 015 950 PubChem CID 74663 UNII 4XE4JYN4G7 Y CompTox Dashboard EPA DTXSID2062036 InChI InChI 1S C6H8O3 c7 3 5 1 2 6 4 8 9 5 h1 2 7 8H 3 4H2 YKey DSLRVRBSNLHVBH UHFFFAOYSA N Y SMILES OCc1oc cc1 CO Properties Chemical formula C 6H 8O 3 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 FurfuralMethoxymethylfurfural Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSynthesis 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 Retrieved from https en wikipedia org w index php title 2 5 Bis hydroxymethyl furan amp oldid 1198516051, wikipedia, wiki, book, books, library,
