66357-60-6Relevant academic research and scientific papers
Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose
Mueller, Christoph,Diehl, Volker,Lichtenthaler, Frieder W.
, p. 10703 - 10712 (1998)
Brief exposure to bromine in water-methanol at 0 °C smoothly and effectively converts furfurylamines with hydroxymethyl (5) or glucosyloxymethyl substituents (16) into the respective 6-substituted 3- pyridinols 9 and 19, whereas the N-methyl-furfurylamines 10 and 17 elaborate the N-methyl-pyridinium betaines 13 and 22. Combination of this multistep one-pot reaction with the large scale-feasible generation of hydroxymethylfurfural (4) from D-fructose and its O-glucosyl analog 15 from isomaltulose, together with their ready conversion into furfurylamines by reductive amination, opens up a preparatively satisfactory, 3-step 'reaction channel' from inexpensive sugars to hydrophilic 3-pyridinols, of interest as intermediate chemicals for drugs of the pyridostigmine type and agrochemicals.
Electrochemical reductive amination of furfural-based biomass intermediates
Roylance, John J.,Choi, Kyoung-Shin
, p. 5412 - 5417 (2016)
Electrochemical reductive amination uses water as the hydrogen source without requiring other chemicals as the reducing agent, providing reaction conditions that are more environmentally benign. The catalytic abilities and efficiencies of various metal electrodes (Ag, Cu, Pt, Sn, Zn) were investigated for the electrochemical reductive amination of 5-hydroxymethylfurfural (HMF), a key intermediate for biomass conversion, with methylamine (CH3NH2). For each metal electrode, the potentials necessary to initiate reductive amination as well as potential dependent Faradaic efficiency (FE) and selectivity were investigated systematically. Based on the results, reduction conditions and a high surface area Ag electrode that can achieve a FE and a selectivity nearing 100% were reported. Furthermore, reductive amination of HMF derivatives such as 5-methylfurfural (5-MF), 2,5-diformylfuran (DFF), and 5-formyl-2-furancarboxylic acid (FFCA) using methylamine as well as reductive amination of HMF using ethanolamine (NH2CH2CH2OH) were conducted to establish electrochemical reductive amination as a general route for the reductive amination of furfural-based biomass intermediates.
Reductive Amination, Hydrogenation and Hydrodeoxygenation of 5-Hydroxymethylfurfural using Silica-supported Cobalt- Nanoparticles
Chandrashekhar, Vishwas G.,Natte, Kishore,Alenad, Asma M.,Alshammari, Ahmad S.,Kreyenschulte, Carsten,Jagadeesh, Rajenahally V.
, (2021/11/30)
Efficient and selective conversion of renewable feedstocks to essential chemicals and fuels applying green and sustainable catalytic processes is of central importance and attracts scientific interest. Among different biomass-based feedstocks, 5-hydroxymethylfurfural (HMF) represents valuable platform compound widely used for the synthesis of valuable chemicals, fuels, and polymers. Here we report cobalt nanoparticles catalyzed reductive amination, hydrogenation and hydrodeoxygenation of HMF to produce furan based primary, secondary and tertiary amines including N-methylamines as well as 2,5-bis(hydroxymethyl)furan, (5-methylfuran-2-yl)methanol and selected N-, O-, and S-containing heterocycles. Key to success for this HMF valorization is the use of reusable silica supported cobalt-based nanoparticles, which have been prepared by the immobilization and pyrolysis of Co-terephthalic acid-piperazine MOF template on silica.
