620-02-0Relevant articles and documents
Catalytic Conversions in Water: a Novel Carbonylation Reaction Catalysed by Palladium Trisulfonated Triphenylphosphine Complexes
Papadogianakis, Georgios,Maat, Leendert,Sheldon, Roger A.
, p. 2659 - 2660 (1994)
The renewable basic chemical 5-hydroxymethylfurfural (HMF) is selectively carbonylated to the new compound 5-formylfuran-2-acetic acid using a water-soluble palladium complex of trisulfonated triphenylphosphine as the catalyst in an acidic aqueous medium at 70 deg C and 5 bar CO pressure; when hydrogen iodide is the acid component, the reaction follows a different course and HMF is selectively reduced to 5-methylfurfural.
Green catalytic synthesis of 5-methylfurfural by selective hydrogenolysis of 5-hydroxymethylfurfural over size-controlled Pd nanoparticle catalysts
Sun, Guohan,An, Jiahuan,Hu, Hong,Li, Changzhi,Zuo, Songlin,Xia, Haian
, p. 1238 - 1244 (2019)
A green approach for the conversion of 5-(hydroxymethyl)furfural (HMF) to 5-methylfurfural (MF) by using size-controlled palladium catalysts has been developed. Palladium nanoparticles (Pd NPs) with various sizes supported on activated carbon were prepared with polyvinylpyrrolidone (PVP) as the capping agent. The reaction results showed that all the PVP-assisted Pd catalysts achieved high selectivity whilst the hydrogenation ability of Pd NPs could be rationally tuned by varying the mole ratio of Pd/PVP. 2.5% Pd-PVP/C (1:2) presented a satisfactory activity with 80% MF yield and 90% selectivity. The reaction kinetics study showed that the transformation of HMF into MF over bifunctional PVP-assisted Pd NPs underwent an acid-catalyzed esterification followed by a Pd-catalyzed hydrogenolysis procedure. The role of formic acid in the transformation is not only as a hydrogen-donating agent but also as a reactant to form the key intermediate. This work provides a novel and environmentally-friendly method for the selective hydrogenation of bio-based HMF to MF.
Dehydration of carbohydrates to 2-furaldehydes in ionic liquids by catalysis with ion exchange resins
Heguaburu, Viviana,Franco, Jaime,Reina, Luis,Tabarez, Carlos,Moyna, Guillermo,Moyna, Patrick
, p. 88 - 91 (2012)
The dehydration of several sugars, including pentoses, hexoses, di, tri, and polysaccharides, in ionic liquids with acidic ion-exchange resins as heterogeneous catalysts was investigated. Good 2-furaldehydes recovery yields, reaching 92% in some cases, were achieved when Dowex 50W ion-exchange resins and 1-n-butyl-3-methylimidazolium chloride ([C4mim]Cl) were used. Our results show that this aproach could represent a promising route towards the cost-efficient production of 2-furaldehydes from carbohydrate-based feedstocks.
Ni-Al/CoOx-catalyzed hydrodeoxygenation of 5-hydroxymethylfurfural into 2,5-dimethylfuran at low temperatures without external hydrogen
An, Yadan,Bai, Guoyi,Bian, Gang,Li, Tianming,Niu, Libo,Xia, Zhanghui
, p. 7763 - 7772 (2021/10/12)
Catalytic hydrodeoxygenation of 5-hydroxymethylfurfural into 2,5-dimethylfuran has received great interest in recent years. In this work, a ternary Ni-Al/CoOx-1 catalyst was fabricated, which provided 96% yield of DMF from in situ hydrodeoxygenation of HMF under mild reaction conditions. XRD, TEM and TPR revealed that the addition of Al to the Ni-Co bimetallic system could make the structure more stable and improve the dispersion of Ni and Co species. XPS, CO-DRIFTS and EPR verified that an enhanced electron transfer from Co species to Ni occurred on Ni-Al/CoOx-1. Reaction mechanism studies unraveled that the Al addition results in promoting in situ H2 production from 2-propanol and accelerating the aldehyde group hydrogenation to a hydroxymethyl group and the subsequent hydrogenolysis into a methyl group, due to the formation of a charge separated metal-couple-site (Niδ-Coδ+) and stronger Lewis acid sites in Ni-Al/CoOx-1. In addition, this ternary Ni-Al/CoOx-1 catalyst exhibits superior recyclability without significant loss of activity for 7 cycles.
Radical induced disproportionation of alcohols assisted by iodide under acidic conditions
Huang, Yang,Jiang, Haiwei,Li, Teng,Peng, Yang,Rong, Nianxin,Shi, Hexian,Yang, Weiran
supporting information, p. 8108 - 8115 (2021/10/29)
The disproportionation of alcohols without an additional reductant and oxidant to simultaneously form alkanes and aldehydes/ketones represents an atom-economical transformation. However, only limited methodologies have been reported, and they suffer from a narrow substrate scope or harsh reaction conditions. Herein, we report that alcohol disproportionation can proceed with high efficiency catalyzed by iodide under acidic conditions. This method exhibits high functional group tolerance including aryl alcohol derivatives with both electron-withdrawing and electron-donating groups, furan ring alcohol derivatives, allyl alcohol derivatives, and dihydric alcohols. Under the optimized reaction conditions, a 49% yield of 5-methyl furfural and a 49% yield of 2,5-diformylfuran were obtained simultaneously from 5-hydroxymethylfurfural. An initial mechanistic study suggested that the hydrogen transfer during this redox disproportionation occurred through the inter-transformation of HI and I2. Radical intermediates were involved during this reaction.