556-48-9Relevant articles and documents
Heterogenized C-Scorpionate Iron(II) Complex on Nanostructured Carbon Materials as Recyclable Catalysts for Microwave-Assisted Oxidation Reactions
Ribeiro, Ana P. C.,Martins, Luísa M. D. R. S.,Carabineiro, Sónia A. C.,Buijnsters, Josephus G.,Figueiredo, José L.,Pombeiro, Armando J. L.
, p. 1821 - 1828 (2018)
The C-scorpionate iron(II) complex [FeCl2(Tpm)] [Tpm=κ3-HC(C3H3N2)3] (1) was immobilized on five different nanostructured carbon materials (nanodiamonds, graphene nanoplatelets, graphene ox
Preparation of supported catalyst and 1, 4 - cyclohexanediol prepared by hydrogenation of fixed bed hydroquinone
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Paragraph 0022-0066, (2021/08/25)
The invention relates γ-Al. 2 O3 Or γ-Al. 2 O3 The preparation of and inorganic carbon supported catalysts and the catalytic hydrogenation of 1, 4 - cyclohexanediol in fixed beds mainly uses γ-Al. 2 O3 Or γ-Al. 2 O3 The transition metal supported by the inorganic carbon is a catalyst, at H. 2 The reaction was carried out in a solution filled with hydroquinone, and 1, 4 - cyclohexanediol was prepared on a fixed bed. The catalyst disclosed by the invention is simple in preparation process, high in conversion rate, 1 and 4 -cyclohexanediol selectivity. The catalyst is low in manufacturing cost, easy to amplify and produce, and closer to industrial production.
Ceria supported Ru0-Ruδ+ clusters as efficient catalyst for arenes hydrogenation
Cao, Yanwei,Zheng, Huan,Zhu, Gangli,Wu, Haihong,He, Lin
supporting information, p. 770 - 774 (2020/08/24)
Selective hydrogenation of aromatic amines, especially chemicals such as aniline and bis(4-aminocyclohexyl)methane for non-yellowing polyurethane, is of particular interests due to the extensive applications. To conquer the existing difficulties in selective hydrogenation, the Ru0-Ruδ+/CeO2 catalyst with solid frustrated Lewis pairs was developed for aromatic amines hydrogenation with excellent activity and selectivity under relative milder conditions. The morphology, electronic and chemical properties, especially the Ru0-Ruδ+ clusters and reducible ceria were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), X-ray photoelectron spectroscopy (XPS), CO2 temperature programmed desorption (CO2-TPD), H2 temperature programmed reduction (H2-TPR), H2 diffuse reflectance Fourier transform infrared spectroscopy (H2-DRIFT), Raman, etc. The 2% Ru/CeO2 catalyst exhibited good conversion of 95% and selectivity greater than 99% toward cyclohexylamine. The volcano curve describing the activity and Ru state was found. Owning to the “acidic site isolation” by surrounding alkaline sites, condensation between the neighboring amine molecules could be effectively suppressed. The catalyst also showed good stability and applicability for other aromatic amines and heteroarenes containing different functional groups.
Composite oxide supported double-transition metal catalyst used for fixed bed catalytic hydroquinone hydrogenation to prepare 1 and 4 - cyclohexanediol
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Paragraph 0022-0069, (2021/08/25)
The double-transition metal-based catalyst is used for fixed bed catalytic hydroquinone hydrogenation preparation 1, 4 - cyclohexanediol, mainly taking composite oxide as a carrier and carrying double-transition metal as a catalyst, and is used for catalyzing hydroquinone hydrogenation to prepare 1 and 4 - cyclohexanediol in a fixed bed. To the catalyst, high selectivity 1 and 4 - cyclohexanediol can be obtained through high-efficiency benzenediol hydrogenation on a fixed bed. The catalyst prepared by the method is simple in process, low in cost, easy to amplify and beneficial to industrial production.
Carbon-supported Ni-based catalyst, preparation method thereof and 1-4 -cyclohexanediol prepared by catalyzing hydroquinone hydrogenation in fixed bed
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Paragraph 0021-0050, (2021/08/25)
The invention provides 1-cyclohexanediol high-surface-area porous-4 - structure inorganic carbon carrier-supported-supported catalyst used for selective hydrogenation Ni of hydroquinone and a preparation method thereof. The catalyst includes a main active component. Auxiliaries and carriers or main active components and carriers. The support is an inorganic carbon support or an acid or base treatment. The main active component is Ni, Ni is 0.01-50 .0 wt % in the weight of the catalyst, and the content of other auxiliaries is 0 - 10.0 wt % of the catalyst. Ni And auxiliaries are supported on an inorganic carbon support by means of impregnation or the like, and the main active component is highly dispersed in the support. In fixed-bed reactors, under certain temperature and pressure and of the catalyst, hydroquinone can be converted to 1 and 4 - cyclohexanediol with high activity and selectivity.
Catalytic transfer hydrogenation of 4-O-5 models in lignin-derived compounds to cycloalkanes over Ni-based catalysts
Chen, Changzhou,Liu, Peng,Xia, Haihong,Zhou, Minghao,Jiang, Jianchun
, p. 582 - 591 (2020/12/01)
There is an urgent need to develop a selective hydrogenolysis of Caryl-O bonds in lignin to produce valued-added chemicals and fuels. Recently, hydrogen has been used in the hydrogenation reaction, which hides inevitable danger and is not economical. Therefore, isopropanol, as a hydrogen-donor solvent, is employed for aryl ether hydrogenolysis in lignin models over nickel supported on a carbon nanotube (CNT). Except for aromatic ether (4-O-5), the Ni/CNT catalyst is also found to be suitable for alkyl-aryl ether (α-O-4 and β-O-4) cleavage in control experiments. The physicochemical characterizations were carried out by means of H2-temperature-programmed reduction, X-ray diffraction, transmission electron microscopy, and X-ray photoelectron spectroscopy analyses. The catalyst can be magnetically recovered and efficiently reused for five consecutive recycling tests in the transfer hydrogenation of aromatic ethers. A mechanism study indicated that the hydrogenolysis cleavage of the ether bond is the first step in the reaction process, and hydrogenation of aromatic rings is only a successive step in which phenol and benzene are intermediate states and are then further hydrogenated. Furthermore, it has been demonstrated that aryl groups play an important role in the hydrogenation of phenol in the competitive catalytic hydrogenation reaction of phenol.
Highly Efficient Cleavage of Ether Bonds in Lignin Models by Transfer Hydrogenolysis over Dual-Functional Ruthenium/Montmorillonite
Xue, Zhimin,Yu, Haitao,He, Jing,Zhang, Yibin,Lan, Xue,Liu, Rundong,Zhang, Luyao,Mu, Tiancheng
, p. 4579 - 4586 (2020/06/21)
Cleavage of ether bonds is a crucial but challenging step for lignin valorization. To efficiently realize this transformation, the development of robust catalysts or catalytic systems is required. In this study, montmorillonite (MMT)-supported Ru (denoted as Ru/MMT) is fabricated as a dual-functional heterogeneous catalyst to cleave various types of ether bonds through transfer hydrogenolysis without using any additional acids or bases. The prepared Ru/MMT material is found to efficiently catalyze the cleavage of various lignin models and lignin-derived phenols; cyclohexanes (fuels) and cyclohexanols (key intermediates) are the main products. The synergistic effect between electron-enriched Ru and the acidic sites on MMT contributes to the excellent performance of Ru/MMT. Systematic studies reveal that the reaction proceeds through two possible reaction pathways, including the direct cleavage of ether bonds and the formation of intermediates with one hydrogenated benzene ring, for all examined types of ether bonds, namely, 4-O-5, α-O-4, and β-O-4.
Selective hydrogenation of lignin-derived compounds under mild conditions
Chen, Lu,Van Muyden, Antoine P.,Cui, Xinjiang,Laurenczy, Gabor,Dyson, Paul J.
, p. 3069 - 3073 (2020/06/17)
A key challenge in the production of lignin-derived chemicals is to reduce the energy intensive processes used in their production. Here, we show that well-defined Rh nanoparticles dispersed in sub-micrometer size carbon hollow spheres, are able to hydrogenate lignin derived products under mild conditions (30 °C, 5 bar H2), in water. The optimum catalyst exhibits excellent selectivity and activity in the conversion of phenol to cyclohexanol and other related substrates including aryl ethers.
One-pot Synthesis of 4-Aminocyclohexanol Isomers by Combining a Keto Reductase and an Amine Transaminase
Sviatenko, Olha,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Venkata Manideep, Kollipara,Merdivan, Simon,Günther, Sebastian,Süss, Philipp,H?hne, Matthias
, p. 5794 - 5799 (2019/08/30)
The efficient multifunctionalization by one-pot or cascade catalytic systems has developed as an important research field, but is often challenging due to incompatibilities or cross-reactivities of the catalysts leading to side product formation. Herein we report the stereoselective preparation of cis- and trans-4-aminocyclohexanol from the potentially bio-based precursor 1,4-cyclohexanedione. We identified regio- and stereoselective enzymes catalyzing reduction and transamination of the diketone, which can be performed in a one-pot sequential or cascade mode. For this, we identified regioselective keto reductases for the selective mono reduction of the diketone to give 4-hydroxycyclohexanone. The system is modular and by choosing stereocomplementary amine transaminases, both cis- and trans-4-aminocyclohexanol were synthesized with good to excellent diastereomeric ratios. Furthermore, we identified an amine transaminase that produces cis-1,4-cyclohexanediamine with diastereomeric ratios >98 : 2. These examples highlight that the high selectivity of enzymes enable short and stereoselective cascade multifunctionalizations to generate high-value building blocks from renewable starting materials. Introduction.
A novel cluster of C5-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold
Huber, Imre,Zupkó, István,Gyovai, András,Horváth, Péter,Kiss, Eszter,Gulyás-Fekete, Gergely,Schmidt, János,Perjési, Pál
, p. 4711 - 4735 (2019/06/04)
A new series (6) of C5-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with IC50 values of 0.68?μM (A2780), 0.69?μM (C33A) and 0.92?μM (MDA-MB-231) compared to cisplatin with 1.30?μM, 3.69?μM and 19.13?μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [IC50 = 0.76?μM (A2780), 2.69?μM (C33A), 1.28?μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such C5-curcuminoids.
