40649-36-3Relevant articles and documents
Hydrogenation of 4-propylphenol over carbon-supported palladium catalyst without external hydrogen: Effect of carbon support and palladium loading
Nagasawa, Yoshiyuki,Hiraishi, Yushi,Horyo, Daiki,Sobu, Tomoki,Taniguchi, Kenkichi,Nanao, Hidetaka,Sato, Osamu,Yamaguchi, Aritomo,Shirai, Masayuki
, p. 431 - 434 (2021/03/15)
The ring hydrogenation of 4-propylphenol in aqueous ethanol solution was studied over graphite- and activated carbon-supported palladium catalysts (Pd/G and Pd/C) with 0.15 wt % of palladium loadings without using external hydrogen. Decomposition of ethan
4-Propylphenol Hydrogenation over Pt-Pd Bimetallic Catalyst in Aqueous Ethanol Solution without External Hydrogen
Kusumawati, Etty Nurlia,Nagasawa, Yoshiyuki,Nanao, Hidetaka,Sasaki, Takehiko,Sato, Osamu,Shirai, Masayuki,Yamaguchi, Aritomo
, p. 1968 - 1971 (2022/01/12)
Ring-hydrogenation of 4-propylphenol (4-PP) to 4-propylcyclohexanone, cis- and trans-4-propylcyclohexanols proceeded over graphite-supported palladium catalysts (Pd/G) in aqueous ethanol solution at 573K without using external hydrogen gas. Compared to Pd
Liquid-phase Hydrodeoxygenation of 4-Propylphenol to Propylbenzene: Reducible Supports for Pt Catalysts
González Escobedo, José Luis,Karinen, Reetta,Lahtinen, Jouko,Lassi, Ulla,Lindblad, Marina,M?kel?, Eveliina,Neuvonen, Jouni,Puurunen, Riikka L.
, (2020/07/06)
Pyrolysis and liquefaction biocrudes obtained from lignocellulose are rich in phenolic compounds that can be converted to renewable aromatics. In this study, Pt catalysts on reducible metal oxide supports (Nb2O5, TiO2), along with irreducible ZrO2 as a reference, were investigated in the liquid-phase hydrodeoxygenation (HDO) of 4-propylphenol (350 °C, 20 bar H2, organic solvent). The most active catalyst was Pt/Nb2O5, which led to the molar propylbenzene selectivity of 77 percent, and a yield of 75 percent (98 percent conversion). Reducible metal oxide supports provided an increased activity and selectivity to the aromatic product compared to ZrO2, and the obtained results are among the best reported in liquid-phase. The reusability of the spent catalysts was also studied. The spent Pt/Nb2O5 catalyst provided the lowest conversion, while the product distribution of the spent Pt/ZrO2 catalyst changed towards oxygenates. The results highlight the potential of pyrolysis or liquefaction biocrudes as a source of aromatic chemicals.
Fine-Bubble-Slug-Flow Hydrogenation of Multiple Bonds and Phenols
Iio, Takuya,Nagai, Kohei,Kozuka, Tomoki,Sammi, Akhtar Mst,Sato, Kohei,Narumi, Tetsuo,Mase, Nobuyuki
supporting information, p. 1919 - 1924 (2020/11/09)
We describe a promising method for the continuous hydrogenation of alkenes or alkynes by using a newly developed fine-bubble generator. The fine-bubble-containing slug-flow system was up to 1.4 times more efficient than a conventional slug-flow method. When applied in the hydrogenation of phenols to the corresponding cyclohexanones, the fine bubble-slug-flow method suppressed over-reduction. As this method does not require the use of excess gas, it is expected to be widely applicable in improving the efficiency of gas-mediated flow reactions.
Surface Modification of a Supported Pt Catalyst Using Ionic Liquids for Selective Hydrodeoxygenation of Phenols into Arenes under Mild Conditions
Ohta, Hidetoshi,Tobayashi, Kanako,Kuroo, Akihiro,Nakatsuka, Mao,Kobayashi, Hirokazu,Fukuoka, Atsushi,Hamasaka, Go,Uozumi, Yasuhiro,Murayama, Haruno,Tokunaga, Makoto,Hayashi, Minoru
supporting information, p. 14762 - 14766 (2019/11/13)
The selective and efficient removal of oxygenated groups from lignin-derived phenols is a critical challenge to utilize lignin as a source for renewable aromatic chemicals. This report describes how surface modification of a zeolite-supported Pt catalyst using ionic liquids (ILs) remarkably increases selectivity for the hydrodeoxygenation (HDO) of phenols into arenes under mild reaction conditions using atmospheric pressure H2. Unmodified Pt/H-ZSM-5 converts phenols into aliphatic species as the major products along with a slight amount of arenes (10 % selectivity). In contrast, the catalyst modified with an IL, 1-butyl-3-methylimidazolium triflate, keeps up to 76 % selectivity for arenes even at a nearly complete conversion of phenols. The IL on the surface of Pt catalyst may offer the adsorption of phenols in an edge-to-face manner onto the surface, thus accelerating the HDO without the ring hydrogenation.
Electrocatalytic Upgrading of Lignin-Derived Bio-Oil Based on Surface-Engineered PtNiB Nanostructure
Zhou, Yulin,Gao, Yijing,Zhong, Xing,Jiang, Wenbin,Liang, Yulin,Niu, Pengfei,Li, Meichao,Zhuang, Guilin,Li, Xiaonian,Wang, Jianguo
, (2019/01/25)
The development of robust electrocatalysts for electrocatalytic hydrogenation (ECH) of guaiacol and related lignin model monomers is necessary for the stabilization or upgrading of bio-oil. Additionally, the efficiency of biomass conversion to bio-oil products remains below the minimum requirements for its implementation at scale. Herein, a PtNiB/CMK-3 catalyst with pronounced ECH performance in the conversion of guaiacol and related model lignin monomers to bio-oil under optimally mild conditions, through a modulation strategy that modified the electronic structure of PtNi via boron alloying, is prepared. Notably, the optimized PtNiB/CMK-3 exhibited an inspiring high faradaic efficiency of 86.2%, which is significantly higher (13.7 times) than that of the PtNi/CMK-3 without B-doping (6.3%). Experimental results and theoretical calculations showed that the B-doping optimized the PtNiB alloy surface electron structure, simultaneously promoting substrate and intermediate adsorption and the ECH process. In addition, the uniform dispersion of PtNiB nanoparticles embedded within the mesoporous channels of CMK-3 ensures an enhanced utilization efficiency, leading to improvements in stability and bio-oil product generation. The lab-scale ECH experiment of guaiacol also certified the scale-up potential. This work opens a promising avenue to the rational design of advanced and highly efficient electrocatalysts for biomass upgrading.
Aliphatic C-H Bond Oxidation with Hydrogen Peroxide Catalyzed by Manganese Complexes: Directing Selectivity through Torsional Effects
Milan, Michela,Bietti, Massimo,Costas, Miquel
supporting information, p. 2720 - 2723 (2018/05/22)
Substituted N-cyclohexyl amides undergo aliphatic C-H bond oxidation with H2O2 catalyzed by manganese complexes. The reactions are directed by torsional effects leading to site-selective oxidation of cis-1,4-, trans-1,3-, and cis-1,2-cyclohexanediamides. The corresponding diastereoisomers are unreactive under the same conditions. Competitive oxidation of cis-trans mixtures of 4-substituted N-cyclohexylamides leads to quantitative conversion of the cis-isomers, allowing isolation and successive conversion of the trans-isomers into densely functionalized oxidation products with excellent site selectivity and good enantioselectivity.
Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction
Luo, Weiwei,Lin, Lili,Zhang, Yu,Liu, Xiaohua,Feng, Xiaoming
, p. 3374 - 3377 (2017/07/15)
An efficient desymmetrizing carbonyl-ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N′-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol methodology originates from the efficient interaction between the catalyst with enophiles, discrimination of the two chair conformations of olefinic components, and the intrinsic six-membered transition-state structure of ene process.
Examples of xylochemistry: Colorants and polymers
Kühlborn, Jonas,Danner, Ann-Kathrin,Frey, Holger,Iyer, Rishab,Arduengo, Anthony J.,Opatz, Till
supporting information, p. 3780 - 3786 (2017/08/23)
Against the backdrop of modern sustainable chemistry and valorization of biomass for chemical raw materials, the syntheses of indigo dyes and polyamides as representatives of two classes of everyday chemical products based on xylochemicals are described. Wood-derived starting materials were transformed into functional materials using the principles of green chemistry to expand the scope of products gained from renewable resources. The indigo dyes were synthesized in a short, straightforward sequence starting from vanillin. Two polyamides, representatives of an important class of polymers, were obtained from 4-propylcyclohexanol, which is one of the longest known (and most abundant) hydrogenative depolymerization products of lignin.
Transfer hydrogenation of 4-propylphenol using ethanol and water over charcoal-supported palladium catalyst
Nagasawa, Yoshiyuki,Nanao, Hidetaka,Sato, Osamu,Yamaguchi, Aritomo,Shirai, Masayuki
, p. 643 - 645 (2016/07/06)
The aromatic hydrogenation of 4-propylphenol to 4-propylcyclohexanone, cis- and trans-4-propylcyclohexanols proceeded over a charcoal-supported palladium catalyst (Pd/C) in water-ethanol cosolvent at 573 K without using any external hydrogen gas. The ring hydrogenation activities in water-ethanol cosolvent over Pd/C were higher than those with a conventional method using externally supplied hydrogen gas. Both water and ethanol were indispensable for the ring hydrogenation in the water-ethanol cosolvent at 573 K.
