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2,5-Furandimethanol is a furan derivative with antioxidant and antibacterial activity.

Synonyms: 5-(Hydroxymethyl)furfuryl Alcohol; NSC 524614; NSC 40737

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Weers, Marco ; von Seggern, Aaron R. ; Vocke, Heinrich ; Taffa, Dereje H. ; Wark, Michael ;

Abstract: Polymeric carbon nitride (PCN) can be prepared by heating of nitrogen rich precursors and is used as a photocatalyst for hydrogen evolution and transformation of organic mols. This work gives a deeper understanding of the different properties of PCN and the observed intermediates when or are chosen as precursors and heated to temperatures in the range of 350-575°C. Melem or a melem-tetramer are the main intermediates when is used as starting material, while urea-based PCN is formed via a supramol. assembly of and . This leads to crucial differences in properties such as surface area, amount of NH2-groups and photocatalytic activity. PCN from , loaded with Pt nanoparticles, shows higher activities for photocatalytic hydrogen evolution due to more NH2-groups. The melem-tetramer shows nanosheetlike structure combined with a high amount of NH2-groups and has the highest activity of all prepared catalysts for the photocatalytic of (HMF) to (BHMF). Thus, this research demonstrates the formation mechanism and the design of PCN based catalysts with a large amount of NH2-groups and a high photocatalytic reduction ability.

Keywords: polymeric carbon nitride ; melem tetramer ; photocatalysis ; 5-hydroxymethylfurfuralreduction ; hydrogen evolution

Purchased from AmBeed:

Piao, Guangxia ; Yoon, Sun Hee ; Cha, Hyun Gil ; Han, Dong Suk ; Park, Hyunwoong ;

Abstract: The electrocatalytic hydrogenation of 5-hydroxymethylfurfural (HMF) to 2,5-bis(hydroxymethyl)furan (BHMF) is an alternative to conventional heterogeneous catalysis with H2 at high temperatures and pressures. Although Ag is the most representative electrocatalyst, it works only under limited conditions. This study synthesizes highly porous dendritic Bi, Sn, and BiSn electrocatalysts using an in situ generated hydrogen bubble template. Density functional theory computations on the adsorption energy and elementary hydrogenation reaction steps of HMF predict the superiority of Bi to Sn and the intermediate behavior of BiSn between Bi and Sn. The dendritic BiSn catalyst generates a current density of ∼144 mA cm−2 at a faradaic efficiency (FE) of ∼100% for BHMF production at pH ∼ 7 (corresponding to the BHMF production rate of ∼2.7 mmol h−1 cm−2) in prolonged electrolysis. Considering the material cost (

Purchased from AmBeed: ; ; ; ; ; 1883-75-6

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Product Details of 2,5-Furandimethanol

CAS No. :1883-75-6
Formula : C6H8O3
M.W : 128.13
SMILES Code : OCC1=CC=C(CO)O1
Synonyms :
5-(Hydroxymethyl)furfuryl Alcohol; NSC 524614; NSC 40737
MDL No. :MFCD00003253
InChI Key :DSLRVRBSNLHVBH-UHFFFAOYSA-N
Pubchem ID :74663

Safety of 2,5-Furandimethanol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of 2,5-Furandimethanol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

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YieldReaction ConditionsOperation in experiment
With sodium hydroxide; 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide; at 0 - 20℃; With reference to Scheme 1 below, 1 ml of 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([EMIm]TFSI, available from Merck) newly serving as an ionic liquid was placed in a round-bottom flask, 0.126 g (1 mmol) of 5-hydroxymethylfurfural (HMF, Compound I) was dissolved, the reaction temperature was adjusted to 0° C., and then sodium hydroxide powder (0.200 g, 5 mmol) was added thereto. Subsequently, the reaction temperature was increased to room temperature so that the reaction took place. After completion of the reaction, 20 ml of dichloromethane was added, after which the filtrate obtained via filtration, namely, the dichloromethane layer was distilled under reduced pressure, thus recovering the ionic liquid. [0057] The lump of filtered particles resulting from recovering the ionic liquid was dissolved in 2 ml of water, and then neutralized with 1 N HCl, so that the pH of the solution was adjusted to about 78. Extraction using ethyl acetate (3×50 ml) and then concentration under reduced pressure were conducted, yielding 2,5-dihydroxymethylfuran (DHMF, Compound II) as a white solid. [0058] The pH of the remaining water layer was adjusted to about 3, followed by performing extraction using ethyl acetate and then concentration under reduced pressure, yielding 5-hydroxymethylfuranoic acid (HMFA, Compound III) as a light yellow solid. The yields of the products are shown in Table 1 below. [0059] The melting point of the light yellow crystals was 239.5° C., and the light yellow crystals were analyzed to be a target compound using 1H-NMR, 13C-NMR. The analytic data was as follows. [0060] HMFA: 1H NMR (300 MHz, acetone-d6): delta 7.16 (d, J=3.4, 1H), 6.47 (d, J=3.4, 1H), 4.59 (s, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 160.9, 159.5, 144.9, 119.6, 109.6, 57.3. [0061] DHMF: 1H NMR (300 MHz, acetone-d6): delta 6.18 (s, 2H), 4.48 (d, J=5.8, 4H), 4.18 (t, J=5.8, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 155.8, 108.22, 57.2.
With 1-butyl-3-methylimidazolium Tetrafluoroborate; sodium hydroxide; at 0 - 20℃; DHMF and HMFA were prepared in the same manner as in Example 1, with the exception that 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIm]BF4, available from C-TRI) was used as the ionic liquid instead of 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([EMIm]TFSI). [0075] The melting point of the light yellow crystals was 239.5° C., and the light yellow crystals were analyzed to be the target compound using 1H-NMR, 13C-NMR. The analytic data was as follows. [0076] HMFA: 1H NMR (300 MHz, acetone-d6): delta 7.16 (d, J=3.4, 1H), 6.47 (d, J=3.4, 1H), 4.59 (s, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 160.9, 159.5, 144.9, 119.6, 109.6, 57.3. [0077] DHMF: 1H NMR (300 MHz, acetone-d6): delta 6.18 (s, 2H), 4.48 (d, J=5.8, 4H), 4.18 (t, J=5.8, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 155.8, 108.22, 57.2.
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YieldReaction ConditionsOperation in experiment
14%; 6%; 76% With oxygen; sodium hydrogencarbonate; In water; at 90℃; for 10h;Catalytic behavior; The catalyst (0.039 g) was added into a solution of HMF(0.40 mmol) and NaHCO3 (1.6 mmol) in deionized water (20 mL).The suspension was heated to 90 C under stirring and bubbledwith O2 at a flow rate of 70 mL min-1. An aliquot (50 muL) of thereaction mixture was taken out at given intervals and diluted to5 mL with deionized water in a volumetric flask. The liquid samplewas then syringe-filtered through a 0.2 lm PTFE membrane and analyzed by HPLC. The concentrations of HMF, HMFCA, FFCA, andFDCA in the reaction solutions were measured by HPLC using theexternal standard calibration curve method. To evaluate the relativestandard deviation (RSD) of the reaction results, four parallelexperiments were carried out by using Pt/3DOM-Ce1-xBixO2-delta ascatalyst. The RSD values for yield of HMFCA, FFCA, and FDCA weredetermined as 1.7percent, 2.4percent, and 2.5percent, respectively.
 

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