1883-75-6Relevant articles and documents
Heteromacrocycles from Ring-Closing Metathesis of Unsaturated Furanic Ethers
Cottier, Louis,Descotes, Gerard,Soro, Yaya
, p. 4285 - 4295 (2003)
New 2,5-bix(unsaturated alkyloxymethyl)-furan led to macrocyclic furanic derivatives in the presence of Grubb's catalyst via dimerization or direct intramolecular metathesis according to the length of the sidearm.
Photo-induced reduction of biomass-derived 5-hydroxymethylfurfural using graphitic carbon nitride supported metal catalysts
Guo, Yuanyuan,Chen, Jinzhu
, p. 101968 - 101973 (2016)
Photo-catalytic reduction of biomass-derived 5-hydroxymethylfurfural (HMF) into 2,5-dihydroxymethylfuran (DHMF) under visible light irradiation is achieved by using a platinum catalyst supported on graphitic carbon nitride (Pt/g-C3N4). Pt/g-C3N4 acts as a multifunctional and tandem catalyst to successively promote the photo-induced water splitting to form hydrogen and the successive activation of the produced hydrogen for HMF reduction, yielding DHMF yield of 6.5% with TOF of 0.457 h-1. This research provides a sustainable and green pathway for biomass conversion using solar radiation as a driving force.
Hydrogenolysis of 5-hydroxymethylfurfural to 2,5-dimethylfuran over supported Pt-Co bimetallic catalysts under mild conditions
Wang, Xiaofeng,Liu, Yuzi,Liang, Xinhua
, p. 2894 - 2902 (2018)
Highly dispersed Pt-Co bimetallic catalysts were deposited on multi-walled carbon nanotubes (MWCNTs) by atomic layer deposition. High-resolution TEM and TPR analyses verified the formation of Pt-Co bimetallic particles. Catalysts were applied for the hydrogenolysis of 5-hydroxymethyfurfural (HMF) to 2,5-dimethyfuran (DMF). A high yield of DMF (>90%) was achieved in the hydrogenolysis of HMF over the optimized Pt-Co/MWCNTs catalyst after 8 h of reaction time under 10 bar H2 at 160 °C. Through a series of experiments and comparison, the synergistic effect among Pt, Co, and MWCNTs was investigated. The results revealed that the synergistic effect between Pt-Co and MWCNTs played an important role in the improvement of selectivity to DMF for Pt-Co/MWCNTs bimetallic catalysts. In addition, steric hindrance appeared when Co loading in Pt-Co/MWCNTs was high and it affected the activity of the Pt-Co bimetallic catalysts. However, moderate activity can inhibit the production of byproducts and thereby improve the yield of DMF.
Efficient route for the construction of polycyclic systems from bioderived HMF
Kucherov,Galkin,Gordeev,Ananikov
, p. 4858 - 4864 (2017)
The first synthesis of tricyclic compounds from biobased 5-hydroxymethylfurfural (HMF) is described. The Diels-Alder reaction was used to implement the transition from HMF to a non-planar framework, which possessed structural cores of naturally occurring biologically active compounds and building blocks of advanced materials. A one-pot, three-step sustainable synthesis in water was developed starting directly from HMF. The reduction of HMF led to 2,5-bis(hydroxymethyl)furan (BHMF), which could be readily involved in the Diels-Alder cycloaddition reaction with HMF-derived maleimide, followed by hydrogenation of the double bond. The described transformation was diastereoselective and proceeded with a good overall yield. The applicability of the chosen approach for the synthesis of analogous structures containing amine functionality on the side chain was demonstrated. To produce the target compounds, only platform chemicals were used with carbohydrate biomass as the single carbon source.
Bio-based furan polymers with self-healing ability
Zeng, Chao,Seino, Hidetake,Ren, Jie,Hatanaka, Kenichi,Yoshie, Naoko
, p. 1794 - 1802 (2013)
We report the preparation of a furan polymer, poly(2,5-furandimethylene succinate) by means of a condensation reaction between bio-based monomers. A reversible Diels-Alder reaction between furan and maleimide groups allowed the formation of network polymers cross-linked by a bismaleimide. By controlling the amount of the bismaleimide, mechanical properties were varied widely. These network polymers healed well when their broken surfaces were activated by bismaleimide solutions or solvent. The polymers also displayed excellent self-healing ability without external stimulus. This polymer class offers a wide range of possibilities to produce materials from biomass that have both practical mechanical properties and healing ability. These materials have the potential to bring great benefits to our daily lives by enhancing the safety, performance, and lifetime of products.
Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides
Yen, Andy,Choo, Ken-Loon,Yazdi, Shabnam K.,Franke, Patrick T.,Webster, Robert,Franzoni, Ivan,Loh, Charles C. J.,Poblador-Bahamonde, Amalia I.,Lautens, Mark
, p. 6307 - 6311 (2017)
Herein we describe a rhodium-catalyzed enantioselective isomerization of meso-oxabicyclic alkenes to 1,2-naphthalene oxides. These potentially useful building blocks can be accessed in moderate to excellent yields with impressive enantioselectivities. Additionally, experimental findings supported by preliminary computations suggest that ring-opening reactions of bridgehead disubstituted oxabicyclic alkenes proceed through the intermediacy of these epoxides and may point to a kinetically and thermodynamically favored reductive elimination as the origin for the observed enantioselectivities.
Direct Conversion of 5-Hydroxymethylfurfural to Furanic Diether by Copper-Loaded Hierarchically Structured ZSM-5 Catalyst in a Fixed-Bed Reactor
Hu, Hualei,Xue, Tingting,Zhang, Zhenxin,Gan, Jiang,Chen, Liangqi,Zhang, Jian,Qu, Fengzuo,Cai, Weijie,Wang, Lei
, p. 3461 - 3469 (2021)
The highly-efficient conversion of 5-hydroxymethylfurfural (HMF) to 2,5-bis(ethoxymethyl)furan (BEMF) was achieved over the copper-loaded hierarchically structured ZSM-5 (Cu/HSZ) catalysts in the continuous fixed-bed reactor. The main reaction path for BEMF synthesis on the Cu/HSZ catalysts was confirmed as following: HMF was firstly hydrogenated to BHMF intermediates over metal sites and then the formed BHMF was etherified by acid sites. Benefiting from the ammonia evaporation (AE) method promoted the dispersion of copper and reduced the acidity, the Cu/HSZ-AE catalyst exhibited more excellent BEMF yield and stability than the catalyst prepared by conventional incipient-wetness impregnation (Cu/HSZ-IW). Indeed, the inactivation of Cu/HSZ-IW catalyst was mainly attributed to the deactivation of copper by carbon species deposition.
Highly selective supported gold catalyst for CO-driven reduction of furfural in aqueous media
Dong, Jing,Zhu, Mingming,Zhang, Gaoshuo,Liu, Yongmei,Cao, Yong,Liu, Su,Wang, Yangdong
, p. 1669 - 1675 (2016)
The reductive transformation of furfural (FAL) into furfuryl alcohol (FOL) is an attractive route for the use of renewable bio-sources but it suffers from the heavy use of H2. We describe here a highly efficient reduction protocol for converting aqueous FAL to FOL. A single phase rutile TiO2 support with a gold catalyst (Au/TiO2-R) that used CO/H2O as the hydrogen source catalyze this reduction efficiently under mild conditions. By eliminating the consumption of fossil fuel-derived H2, our process has the benefit afforded by using CO as a convenient and cost competitive reducing reagent.
Selective Conversion of 5-Hydroxymethylfuraldehyde Using Cp?Ir Catalysts in Aqueous Formate Buffer Solution
Wu, Wei-Peng,Xu, Yong-Jian,Zhu, Rui,Cui, Min-Shu,Li, Xing-Long,Deng, Jin,Fu, Yao
, p. 1209 - 1215 (2016)
The highly selective hydrogenation/hydrolytic ring-opening reaction of 5-hydroxymethylfuraldehyde (5-HMF) was catalyzed by homogeneous Cp?IrIII half-sandwich complexes to produce 1-hydroxy-2,5-hexanedione (HHD). Adjustment of pH was found to regulate the distribution of products and reaction selectivity, and full conversion of 5-HMF to HHD with 99 % selectivity was achieved at pH 2.5. A mechanistic study revealed that the hydrolysis/ring-opening reaction of 2,5-bis-(hydroxymethyl)furan is the important intermediate reaction step. In addition, an isolated yield of 85 % for HHD was obtained in a 10 g-scale experiment, and the reaction with fructose as the starting material also led to a 98 % GC yield (71.9 % to fructose) of HHD owing to the excellent tolerance of the catalyst under acidic conditions. pH dependent: A catalytic system is developed for the selective conversion of 5-hydroxymethylfuraldehyde to 1-hydroxy-2,5-hexanedione in high yield and selectivity. The Cp?IrIII half-sandwich catalysts have an excellent tolerance to acidic aqueous conditions and can transform 5-HMF in the hydrolysis solution of fructose in excellent yield, demonstrating a potential for a large-scale production.
Efficient and Selective Electrochemical and Photoelectrochemical Reduction of 5-Hydroxymethylfurfural to 2,5-Bis(hydroxymethyl)furan using Water as the Hydrogen Source
Roylance, John J.,Kim, Tae Woo,Choi, Kyoung-Shin
, p. 1840 - 1847 (2016)
Reductive biomass conversion has been conventionally conducted using H2 gas under high-temperature and -pressure conditions. In this study, efficient electrochemical reduction of 5-hydroxymethylfurfural (HMF), a key intermediate for biomass conversion, to 2,5-bis(hydroxymethyl)furan (BHMF), an important monomer for industrial processes, was demonstrated using Ag catalytic electrodes. This process uses water as the hydrogen source under ambient conditions and eliminates the need to generate and consume H2 for hydrogenation, providing a practical and efficient route for BHMF production. By systematic investigation of HMF reduction on the Ag electrode surface, BHMF production was achieved with the Faradaic efficiency and selectivity nearing 100%, and plausible reduction mechanisms were also elucidated. Furthermore, construction of a photoelectrochemical cell (PEC) composed of an n-type BiVO4 semiconductor anode, which uses photogenerated holes for water oxidation, and a catalytic Ag cathode, which uses photoexcited electrons from BiVO4 for the reduction of HMF to BHMF, was demonstrated to utilize solar energy to significantly decrease the external voltage necessary for HMF reduction. This shows the possibility of coupling electrochemical HMF reduction and solar energy conversion, which can provide more efficient and environmentally benign routes for reductive biomass conversion.
