A facile one-step polymerization strategy is explored to achieve novel catechol-based materials. Depending on the functionality of the catechol, the as-prepared product can be used to modify at will the surface tension of nano and bulk structures, from oleo-/hydrophobic to highly hydrophilic. A hydrophobic catechol prepared thus polymerized shows the ability to self-assemble as solid nanoparticles with sticky properties in polar solvent media. Such a versatile concept is ideal for the development of catechol-based multifunctional materials.
A series of catechol derivatives with a different number of linear alkyl chain substituents, and different length, have been shown to polymerize in the presence of aqueous ammonia and air, yielding hydrophobic coatings that present the ability to provide robust and efficient water repellency on weaved textiles, including hydrophilic cotton. The polymerization strategy presented exemplifies an alternative route to established melanin- and polydopamine-like functional coatings, affording designs in which all catechol (adhesive) moieties support specific functional side chains for maximization of the desired (hydrophobic) functionality. The coatings obtained proved effective in the transformation of polyester and cotton weaves, as well as filter paper, into reusable water-repellent, oil-absorbent materials capable of retaining roughly double their weight in model compounds (n-tetradecane and olive oil), as well as of separating water/oil mixtures by simple filtration.
The catalytic transfer hydrogenation (CTH) of glucose to sorbitol has been studied using a wide collection of different biomass-derived alcohols and diols as hydrogen donors. Catalytic activity results reflect the feasibility to conduct this transformation in the presence of conventional, commercially available Raney Ni-type sponges as catalysts. Sacrificial diols displayed a superior performance as hydrogen donors as compared to short-chain alcohols, including secondary alcohols. Among them, terminal diols such as 1,4-butanediol and 1,5-pentanediol were revealed as excellent hydrogen donors, providing a high selectivity in the conversion of glucose into sorbitol. As for the catalysts, molybdenum promotion provided a very high catalytic activity to sponge nickel catalysts, even under mild temperature conditions. The transformation was also studied in a fixed-bed reactor under continuous-flow operation conditions. Results demonstrate that the catalysts are highly stable and able to operate for at least 550 h on stream with a high selectivity in the CTH of glucose to sorbitol.
Featured Application: Catalytic transfer hydrogenation from alcohols allow converting under mild reaction conditions glucose into sorbitol.Abstract: Sorbitol production from glucose was studied through catalytic transfer hydrogenation (CTH) over Raney nickel catalysts in alcohol media, used as solvents and hydrogen donors. It was found that alcohol sugars, sorbitol and mannitol, can be derived from two hydrogen transfer pathways, one produced involving the sacrificing alcohol as a hydrogen donor, and a second one involving glucose disproportionation. Comparison between short-chain alcohols evidenced that ethanol was able to reduce glucose in the presence of Raney nickel under neutral conditions. Side reactions include fructose and mannose production via glucose isomerization, which occur even in the absence of the catalyst. Blank reaction tests allowed evaluating the extension of the isomerization pathway. The influence of several operation parameters, like the temperature or the catalyst loading, as well as the use of metal promoters (Mo and Fe-Cr) over Raney nickel, was examined. This strategy opens new possibilities for the sustainable production of sugar alcohols.Sorbitol production was reported to be carried out using cellulose in the presence of noble metals [9] and transition metal-based catalysts [10,11]. However, a most extended alternative is its production starting from glucose. At an industrial scale, sorbitol is produced via glucose hydrogenation [2] as it is the most affordable precursor [12], whose production is liable to be obtained via cellulose hydrolysis [13,14]. The reaction mechanism consists of the reduction of carbonyl groups of saccharides under hydrogen pressure in the presence of a solid metal catalyst based on Ni, Pd, Pt, or Ru [15,16]. All these catalysts are easily recoverable and display good catalytic activity in terms of sorbitol yield, operating under aqueous-phase solution [6,[17][18][19][20]. In recent years, Raney nickel and ruthenium catalysts made a clean sweep on sorbitol production. Ru presents higher activity and selectivity to sorbitol [16,21] than Raney nickel catalysts, but this metal is much more expensive than nickel-based catalysts. In this way, Raney nickel was revealed as the most interesting active phase to be used in the industrial-scale hydrogenation of glucose [21,22], mostly because of its low price [23]. Nevertheless, the lower catalytic activity of nickel as compared to other precious-metal-based conventional hydrogenation catalysts, such as ruthenium, results in the need for high hydrogen pressure and harsh operating conditions. Consequently, a significant energy demand must be satisfied compared to that required when using more active hydrogenation catalysts and, thus, higher environmental impacts are associated with the use of Raney nickel catalysts [24].This work focuses on gaining insights into a developing alternative reaction pathway to the conventional hydrogenation procedure used to transform glucose into sorbitol by exploring the feasibility of car...
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