- Isophthalonitrile (IPN) hydrogenation over K modified Ni-Co supported catalysts: Catalyst characterization and performance evaluation
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The hydrogenation of isophthalonitrile (IPN) to meta-xylylenediamine (m-XDA) is usually catalyzed by the Raney or supported Ni based catalysts in the presence of basic additive. Although the supported catalysts are safer than the Raney Ni catalysts, they have lower selectivity to m-XDA. This work revealed that the acid sites of NiCo/Al2O3 were responsible for the condensation reactions between amines and imines, which were the dominant side reactions. Besides the original acid sites on γ-Al2O3, the loading of Ni-Co introduced new acid sites, which had a greater contribution to the condensation reactions. The K modification significantly enhanced the selectivity to m-XDA by reducing the two kinds of acid sites. Due to the formation mechanism of new acid sites and the K modification mechanism on these sites, both the K loading and K impregnation sequence affected the catalytic performance. When 3.0 wt% K was introduced to NiCo/Al2O3 by co-impregnation (3KNiCo/Al2O3), the catalyst acidity decreased by 82%, and the selectivity to m-XDA increased from 45.5% to 99.9%. The superiority of the optimized catalyst 3KNiCo/Al2O3 was also confirmed when no basic additive was used.
- Liu, Chang,Wang, Tiefeng
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Read Online
- Ni-Co-Cu supported on pseudoboehmite-derived Al2O3: Highly efficient catalysts for the hydrogenation of organic functional groups
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Ni-Co-Cu catalysts supported on pseudoboehmite-derived Al2O 3 were developed for efficient hydrogenation of organic functional groups: CN and NO2 associated with benzene as well as CC in butynediol. Factors such as thermo-treatment of pseudoboehmite, Ni loading, Cu and Co content, and catalyst operating parameters were systematically studied. Among the catalysts, 20%Ni-3%Cu-5%Co/Al2O3 performed the best, showing 100% feed conversion and 84-99.8% selectivity of target products. Techniques such as N2 sorption measurement, scanning electron microscope, hydrogen temperature-programmed reduction and desorption, X-ray photoelectron spectroscopy, and in situ X-ray diffraction were used to characterize the catalysts. The superior performance of the catalyst can be attributed to synergetic interaction among the Ni-Cu-Co constitutes as well as enhancement of Ni2+ reduction and Ni0 dispersion that are resulted due to the co-presence of Cu and Co.
- Shi, Tianbao,Li, Hui,Yao, Lianghong,Ji, Weijie,Au, Chak-Tong
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Read Online
- Role of acid sites and surface hydroxyl groups in isophthalonitrile hydrogenation catalyzed by supported Ni-Co catalysts
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meta-Xylylenediamine (m-XDA) is industrially produced by the hydrogenation of isophthalonitrile (IPN) using Raney Ni/Co and basic additives. Compared with Raney Ni/Co, the supported Ni/Co catalysts are safer and have better mechanical strength. This work aimed at studying the catalytic performance of the supported Ni-Co catalysts in hydrogenation of IPN to m-XDA. The active sites for the condensation side reactions were studied using Ni-Co catalysts supported on different oxides and with different loadings. It was found that the acid sites catalyzed the condensation reactions between intermediate imines and amines. Two types of acid sites existed on the supported Ni-Co catalysts, namely, the original acid sites of the support and new acid sites formed by Ni/Co aluminates. In addition to acid sites, the surface hydroxyl groups on the oxide supports also catalyzed the condensation reactions, but were not active for the hydrogenation reaction. By increasing the Ni-Co loading, the selectivity to m-XDA was significantly enhanced, which was attributed to the suppression of both acid sites and hydroxyl groups. Compared to the low-loading catalysts (5Ni-1.25Co/Al2O3 and 5Ni-1.25Co/SiO2), the high-loading catalysts (20Ni-5Co/Al2O3 and 20Ni-5Co/SiO2) increased the m-XDA selectivity from ~45.5 to 99.9%.
- Liu, Chang,Hou, Ruijun,Wang, Tiefeng
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Read Online
- Catalytic hydrogenation of isophthalonitrile (IPN) over supported monometallic and bimetallic catalysts
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The hydrogenation of Isophthalonitrile (IPN) to meta-xylylenediamine (m-XDA) is usually catalyzed by RANEY or supported Ni based catalysts in the presence of a basic additive. The supported catalysts have better mechanical strength and are safer than RANEY Ni catalysts. This work aimed to study the catalytic performance of γ-Al2O3 supported Ni and Ni-M (M = Fe, Co, Cu) bimetallic catalysts in IPN hydrogenation. The H2-TPR results revealed that the introduction of a second metal enhanced the reducibility of Ni catalyst. The Ni-M bimetallic catalysts also had different metal dispersion, electronic properties and adsorption strength. Among Fe, Co and Cu, Fe showed the best promoting effect, which was attributed to the strong N-metal bonding and weak H-metal adsorption strength, which enhanced the catalytic activity and m-XDA selectivity. The catalytic performance also strongly depended on the Ni-Fe mass ratio. For the γ-Al2O3 supported Ni and Ni-M catalysts with a low Ni loading of 5 wt%, the rate constant kr increased from 0.024 mol0.2 L-0.2 min-1 over 5Ni/Al2O3 to 0.033 mol0.2 L-0.2 min-1 over 5Ni-1.67Fe/Al2O3, meanwhile the m-XDA selectivity increased from 34.7% to 49.5%. Over the Ni-Fe bimetallic catalyst with high metal loading, 20Ni-5Fe/Al2O3, a very high m-XDA selectivity of 99.9% was obtained.
- Liu, Chang,Li, Xiaodan,Wang, Tiefeng
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Read Online
- METHOD FOR PRODUCING m-XYLYLENE DIAMINE
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PROBLEM TO BE SOLVED: To provide a method for producing m-xylylene diamine that makes it possible to efficiently produce m-xylylene diamine by reducing the formation of by-products even when a reaction temperature is lowered in a hydrogenation reaction step. SOLUTION: In the presence of a catalyst with palladium carried on carbon and in the absence of ammonia and an amine compound (excluding a reaction product), 1,3-dicyanobenzene and hydrogen are reacted at 0°C or higher and 50°C or lower, and hydrogen is added to the 1,3-dicyanobenzene, producing m-xylylene diamine. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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Paragraph 0061-0073; 0075; 0079
(2021/08/13)
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- Modulating: Trans -imination and hydrogenation towards the highly selective production of primary diamines from dialdehydes
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Bio-based primary diamines are important building blocks for sustainable bio-polymers, but their synthesis remains challenging due to the high susceptibility to polymerization. Herein, we have developed a new strategy to suppress the polymerization by employing a more nucleophilic alkylamine to scavenge the dialdehyde and a Co/ZrO2 catalyst to regulate the trans-imination and hydrogenation activity. With this strategy, 2,5-bis(aminomethyl)furan (BAMF), a promising monomer for the production of new polyamides and polyureas, is successfully synthesized via the reductive amination of biomass-derived 2,5-diformylfuran (DFF) under a H2 and NH3 atmosphere with an unprecedentedly high selectivity up to 95%. This strategy is applicable to the reductive amination of other biomass-derived dialdehydes, thus paving a new way to bio-based diamine monomers. This journal is
- Hao, Rui,Li, Lin,Liu, Fei,Qi, Haifeng,Su, Yang,Wang, Aiqin,Yang, Jingyi,Zhang, Leilei,Zhang, Tao
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p. 6897 - 6901
(2020/11/09)
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- Cobalt pincer complexes for catalytic reduction of nitriles to primary amines
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Various cobalt pincer type complexes 1-6 were applied for the catalytic hydrogenation of nitriles to amines. Among these, catalyst 4 is the most efficient, allowing the reduction of aromatic as well as aliphatic nitriles in moderate to excellent yields.
- Schneek?nig, Jacob,Tannert, Bianca,Hornke, Helen,Beller, Matthias,Junge, Kathrin
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p. 1779 - 1783
(2019/04/27)
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- Green and convenient protocols for the efficient reduction of nitriles and nitro compounds to corresponding amines with NaBH4 in water catalyzed by magnetically retrievable CuFe2O4 nanoparticles
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Abstract: In this study, firstly, CuFe2O4 nanoparticles were prepared by a simple operation. The structure of the mentioned nanoparticles was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma-optical emission spectrometry, vibrating sample magnetometer and also Brunauer–Emmett–Teller and Barrett–Joyner–Halenda analyses. The prepared magnetically copper ferrite nanocomposite was successfully applied as a simple, cost-effective, practicable, and recoverable catalyst on the green, highly efficient, fast, base-free, and ligand-free reduction of nitriles and also on the affordable and eco-friendly reduction of nitro compounds with the broad substrate scope to the corresponding amines with NaBH4 in water at reflux in high to excellent yields. Graphical abstract: [Figure not available: see fulltext.].
- Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein
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- Facile synthesis of supported Ru-Triphos catalysts for continuous flow application in selective nitrile reduction
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The selective catalytic hydrogenation of nitriles represents an important but challenging transformation for many homogeneous and heterogeneous catalysts. Herein, we report the efficient and modular solid-phase synthesis of immobilized Triphos-type ligands in very high yields, involving only minimal work-up procedures. The corresponding supported ruthenium-Triphos catalysts are tested in the hydrogenation of various nitriles. Under mild conditions and without the requirement of additives, the tunable supported catalyst library provides selective access to both primary amines and secondary imines. Moreover, the first application of a Triphos-type catalyst in a continuous flow process is presented demonstrating high catalyst life-time over at least 195 hours without significant activity loss.
- Konrath, Robert,Heutz, Frank J.L.,Steinfeldt, Norbert,Rockstroh, Nils,Kamer, Paul C.J.
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p. 8195 - 8201
(2019/09/19)
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- NICKEL DIATOMACEOUS EARTH CATALYST AND METHOD FOR PRODUCING THE SAME
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A nickel diatomaceous earth catalyst having a weight loss rate measured by hydrogen-TG at 400 to 600° C. of 0.05 to 2.0%.
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Paragraph 0072
(2018/11/21)
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- Cobalt complex, preparation method thereof, and application thereof in selective catalysis of transfer hydrogenation reaction of cyano group
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The invention discloses a cobalt complex, a preparation method thereof, and an application thereof in the selective catalysis of a transfer hydrogenation reaction of a cyano group. The structural formula of the cobalt complex is represented by formula I. The cobalt complex is prepared through a reaction of a cobalt salt and an NNP ligand or a PNP ligand under the protection of an inert atmosphere;and the chemical formula of the cobalt salt is CoX12, wherein X1 represents halogen, a sulfate radical, a perchlorate radical, a hexafluorophosphate radical, a hexafluoroantimonate radical, a tetrafluoroborate radical, a trifluoromethanesulfonate radical or a tetra(pentafluorophenyl)borate radical. The cobalt complex can be used in the selective catalysis of the transfer hydrogenation reaction ofthe cyano group to obtain a primary amine compound, a secondary amine compound and a tertiary amine compound, the primary amine compound, the secondary amine compound and the tertiary amine compoundare important intermediates in a series of subsequent functionalizing reactions, and the cobalt complex has a very high catalysis activity, and has great research values and a great application prospect.
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Paragraph 0157-0159; 0161
(2018/05/07)
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- Synthesis of Renewable meta-Xylylenediamine from Biomass-Derived Furfural
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We report the synthesis of biomass-derived functionalized aromatic chemicals from furfural, a building block nowadays available in large scale from low-cost biomass. The scientific strategy relies on a Diels–Alder/aromatization sequence. By controlling the rate of each step, it was possible to produce exclusively the meta aromatic isomer. In particular, through this route, we describe the synthesis of renewably sourced meta-xylylenediamine (MXD). Transposition of this work to other furfural-derived chemicals is also discussed and reveals that functionalized biomass-derived aromatics (benzaldehyde, benzylamine, etc.) can be potentially produced, according to this route.
- Scodeller, Ivan,Mansouri, Samir,Morvan, Didier,Muller, Eric,de Oliveira Vigier, Karine,Wischert, Raphael,Jér?me, Fran?ois
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supporting information
p. 10510 - 10514
(2018/08/17)
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- Preparation Method for Aromatic Diamine Compounds by Hydrogenation Reaction of Aromatic Nitrile Compounds
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The present invention refers to a ruthenium (Ru) and/or palladium (Pd) number it rises, light, activated carbon, carbon nanotube and/or yes pin carrying on a support selected from the group consisting of aromatic nitrile compound hydrogenated catalyst is at least 95% improved for nitration of aromatic manufacturing method for nitration of aromatic yield number bath a number under public affairs substrate.
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Paragraph 0055-0056; 0059; 0065; 0068; 0073
(2017/09/30)
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- Selective Hydrogenation of Nitriles to Primary Amines by using a Cobalt Phosphine Catalyst
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A general procedure for the catalytic hydrogenation of nitriles to primary amines by using a non-noble metal-based system is presented. Co(acac)3 in combination with tris[2-(dicyclohexylphosphino)ethyl]phosphine efficiently catalyzes the selective hydrogenation of a wide range of (hetero)aromatic and aliphatic nitriles to give the corresponding amines.
- Adam, Rosa,Bheeter, Charles Beromeo,Cabrero-Antonino, Jose R.,Junge, Kathrin,Jackstell, Ralf,Beller, Matthias
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p. 842 - 846
(2017/03/17)
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- PRODUCTION OF XYLENE DERIVATIVES
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The present invention relates to the production of xylene derivatives from furfural and its derivatives. The invention describes new routes for converting furfural and its derivatives into xylene derivatives including novel intermediates.
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Page/Page column 24
(2017/07/06)
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- Mild and Selective Cobalt-Catalyzed Chemodivergent Transfer Hydrogenation of Nitriles
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Herein, we describe a selective cobalt-catalyzed chemodivergent transfer hydrogenation of nitriles to synthesize primary, secondary, and tertiary amines. The solvent effect plays a key role for the selectivity control. The general applicability of this procedure was highlighted by the synthesis of more than 70 amine products bearing various functional groups in high chemoselectivity. Moreover, this mild system achieved >2000 TONs (turnover numbers) for the transfer hydrogenation of nitriles.
- Shao, Zhihui,Fu, Shaomin,Wei, Mufeng,Zhou, Shaolin,Liu, Qiang
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supporting information
p. 14653 - 14657
(2016/11/23)
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- METHOD FOR PRODUCING M-XYLYLENEDIAMINE AND METHOD FOR PRODUCING BISAMIDE COMPOUND
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A method for producing meta-xylylenediamines includes a reaction step in which monohalogenated benzenes, formaldehydes, and an amide compound having a primary amide group or a secondary amide group are allowed to react in the presence of an acidic liquid, a dehalogenation step in which the halogen atom derived from the monohalogenated benzenes is replaced with a hydrogen atom, and a deprotection step in which the primary amide group or the secondary amide group derived from the amide compound is converted to an amino group. In the reaction step, the acidic liquid contains inorganic acid, the equivalent ratio of the hydrogen atom of the inorganic acid relative to the monohalogenated benzenes is more than 16; the acidic liquid has an inorganic acid concentration of more than 80 mass%; and the reaction temperature is more than 40°C.
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Paragraph 0179-0182
(2016/10/08)
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- HIGH-YIELD METHOD FOR RECOVERING XYLYLENEDIAMINE
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PROBLEM TO BE SOLVED: To provide a high-yield method for recovering xylylenediamine, which is effective when a liquid reaction product, which is obtained by hydrogenating phthalonitriles, is distilled to recover xylylenediamines and a loss of the xylylenediamines, which are derived from a high boiling point component to be produced by polycondensation of the xylylenediamines and are left standing at the bottom of a distillation column, is solved. SOLUTION: The high-yield method for recovering xylylenediamine comprises the steps of: purifying crude xylylenediamines by distillation to obtain the xylylenediamines; and thermally decomposing the high boiling point component, which is produced by polymerizing the xylylenediamines left standing at the bottom of the distillation column after the distillation is completed, to regenerate the xylylenediamines so that a recovery rate of the xylylenediamines is increased. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0023
(2016/12/22)
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- Method for preparing xylylenediamine
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The present invention relates to a method for synthesizing meta-xylylenediamine by making xylene react with ammonia at lower temperatures and neutralizing xylylenediamine hydrochloride obtained from the reaction in an alkaline solution. In the present invention, the reaction is made at lower temperatures, normal pressure or lower pressure, thereby taking less facility investment cost and process cost compared with a hydrogenation reaction method.COPYRIGHT KIPO 2015
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Paragraph 0034-0035
(2016/12/12)
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- Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels
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Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.
- Yang, Donglai,Arifhodzic, Lejla,Ganellin, C. Robin,Jenkinson, Donald H.
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supporting information
p. 907 - 923
(2013/07/27)
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- PROCESS FOR THE DIRECT AMINATION OF ALCOHOLS USING AMMONIA TO FORM PRIMARY AMINES BY MEANS OF A XANTPHOS CATALYST SYSTEM
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The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.
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Paragraph 0063
(2014/01/08)
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- Hydrogen transfer reduction of nitriles in DBU based ionic liquids
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Raney nickel catalyzed transfer hydrogenation of nitrile was proposed, with formats as hydrogen donor. Three ionic liquids, including [DBUH +][C2H5COO-], [DBUH +][C3H7COO-], and [DBUH +][C4H9COO-], were prepared as reaction medium, and [DBUH+][C4H9COO -] showed the best performance. Various nitriles were reduced with potassium formate as hydrogen donor, and considerable to excellent yields of amines were given. The ionic liquid can be used for 6 times at least, and the reaction process is clean. ARKAT-USA, Inc.
- Chen, Xinzhi,Zhou, Shaodong,Qian, Chao
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experimental part
p. 128 - 136
(2012/09/11)
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- Application of alkoxide in catalytic transfer hydrogenation of unsaturated nitrogen compounds
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Alcoholate was utilized in catalytic transfer hydrogenation of unsaturated nitrogen compounds. In the reduction of nitro compounds, oximes and imines, alkoxide was used as the promoter, with alcohol as the hydrogen source, while in the reduction of nitriles, alkoxide was used as the hydrogen source. Springer Science+Business Media B.V. 2012.
- Chen, Xinzhi,Zhou, Shaodong,Chen, Yuehan,Dong, Zehan,Gao, Yeyu,Qian, Chao,He, Chaohong
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p. 2255 - 2269
(2013/02/23)
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- PROCESS FOR PRODUCING XYLYLENEDIAMINE
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The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass% or less and a xylylenediamine content of 1 mass% or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.
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Page/Page column 7-8; 11
(2011/06/24)
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- Improved ruthenium-catalyzed amination of alcohols with ammonia: Synthesis of diamines and amino esters
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Diamination of diols: The first homogeneously catalyzed diaminations of primary and secondary diols with ammonia give the corresponding diamines. Other primary as well as secondary alcohols including hydroxy-substituted esters can also be efficiently converted to primary amines. This atom-efficient and selective amination method proceeds in an ammonia atmosphere without additional hydrogen sources. Copyright
- Imm, Sebastian,Baehn, Sebastian,Zhang, Min,Neubert, Lorenz,Neumann, Helfried,Klasovsky, Florian,Pfeffer, Jan,Haas, Thomas,Beller, Matthias
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supporting information; experimental part
p. 7599 - 7603
(2011/10/01)
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- PRODUCTION METHOD OF XYLYLENEDIAMINE
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A method of producing xylylenediamine by the hydrogenation of dicyanobenzene obtained by the ammoxidation of xylene in a high yield while prolonging the catalyst life. In the method, a molten dicyanobenzene from which compounds having a boiling point lower than that of dicyanobenzene have been removed but compounds having a boiling point higher than that of dicyanobenzene are not removed is dissolved in a solvent containing liquid ammonia. By this dissolution, at least part of dicyanobenzene polymers precipitates as insolubles. The precipitates are removed by a solid-liquid separation. By subjecting the resulting solution containing the dicyanobenzene polymers in a reduced amount to hydrogenation, xylylenediamine is produced in a high yield and the life time of hydrogenation catalyst is prolonged.
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Page/Page column 6
(2010/07/08)
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- CURING AGENT FOR LOW TEMPERATURE CURE APPLICATIONS
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The present invention discloses both amine compositions and amine-epoxy compositions containing N,N′-dimethyl-meta-xylylenediamine. A novel process for producing amines such as N,N′-dimethyl-meta-xylylenediamine, and structurally similar amines, is also disclosed.
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Page/Page column 13-14
(2010/03/31)
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- Curing agent for low temperature cure applications
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The present invention discloses both amine compositions and amine-epoxy compositions containing N,N'-dimethyl-meta-xylylenediamine. A novel process for producing amines such as N,N'-dimethyl-meta-xylylenediamine, and structurally similar amines, is also disclosed.
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Page/Page column 18
(2010/04/24)
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- Process for preparing a curing agent for low temperature cure applications
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The present invention discloses both amine compositions and amine-epoxy compositions containing N,N'-dimethyl-meta-xylylenediamine. A novel process for producing amines such as N,N'-dimethyl-meta-xylylenediamine, and structurally similar amines, is also disclosed.
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Page/Page column 18
(2010/04/24)
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- PRODUCTION METHOD OF PRIMARY AMINES AND CATALYSTS FOR PRODUCING PRIMARY AMINES
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A method of producing a primary amine by the hydrogenation of a nitrile in the presence of a hydrogenation catalyst. The hydrogenation catalyst contains at least one metal selected from the group consisting of nickel, cobalt and iron. Before use in the hydrogenation of nitrile, the hydrogenation catalyst is pretreated with at least one treating agent selected from the group consisting of hydrocarbons, alcohols, ethers, esters and carbon monoxide at 150 to 500° C.
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Page/Page column 6
(2008/06/13)
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- Method for the Production of Xylyendiamine
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Process for preparing o-, m- or p-xylylenediamine by hydrogenation of o-, m- or p-phthalonitrile in the presence of a heterogenous catalyst, which comprises feeding a solution of the phthalonitrile in the corresponding isomer of crude xylylenediamine into the hydrogenation reactor, with the crude xylylenediamine having a purity in the range from 85 to 99.7% by weight and a content of higher boilers in the range from 0.3 to 15% by weight.
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Page/Page column 4
(2008/12/04)
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- Process for Preparing Xylylenediamine by Continuous Hydrogenation of Phthalontrile
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Processes for preparing a xylylenediamine by continuous hydrogenation, wherein the processes comprise: introducing a liquid circulation stream comprising a phthalonitrile and ammonia into a reactor to continuously hydrogenate the phthalonitrile in the presence of a heterogenous catalyst and the ammonia such that a reactor effluent comprising the xylylenediamine is formed; drawing off a portion of the reactor effluent to provide a first recycle stream; mixing at least a portion of the first recycle stream in a mixing unit with liquid ammonia and fresh phthalonitrile in solid or molten form to provide a second recycle stream; and recycling the second recycle stream to the liquid circulation stream, or wherein the second recycle stream and any remaining unmixed portion of the first recycle stream are both recycled to the liquid circulation stream.
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Page/Page column 6
(2008/12/06)
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- Functionalized Photoreactive Compounds
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The present invention concerns functionalized photoreactive compounds of formula (I), that are particularly useful in materials for the alignment of liquid crystals. Due to the adjunction of an electron withdrawing group to specific molecular systems bearing an unsaturation directly attached to two unsaturated ring systems, exceptionally high photosensitivities, excellent alignment properties as well as good mechanical robustness could be achieved in materials comprising said functionalized photoreactive compounds of the invention.
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- Production of Xylylenediamines
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A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.
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Page/Page column 3-7
(2008/06/13)
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- PROCESS FOR PRODUCING HIGHLY PURIFIED XYLYLENEDIAMINE
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A method of producing xylylenediamine from xylene. In the method, xylene is converted into dicyanobenzene by ammoxidation. The produced dicyanobenzene is extracted into an organic solvent. The extact is then distilled to separate dicyanobenzene from the organic solvent. After added with a solvent, the separated dicyanobenzene is hydrogenated in a liquid phase. Finally, the hydrogenation product is purified by distillation to obtain a highly pure xylylenediamine. The method is conducted in a simple and low energy-consuming process.
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Page/Page column 6-8
(2008/06/13)
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- Method for producing xylylenediamine
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A method of producing xylylenediamine of the present invention includes the steps of : subjecting a liquid mixture of phthalonitriles with liquid ammonia or a mixture of liquid ammonia and an organic solvent to a first catalytic hydrogenation treatment, thereby hydrogenating the phthalonitriles to obtain a reaction product (A), wherein a content of the liquid ammonia or the mixture of liquid ammonia and an organic solvent is 80 wt% or more; removing the liquid ammonia in the reaction product (A) to obtain a reaction product (B); subjecting the reaction product (B) to a second catalytic hydrogenation treatment, thereby hydrogenating cyanobenzylamine to obtain a reaction product (C); and distilling the reaction product (C) to purify xylylenediamine.
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Page/Page column 6-8
(2008/06/13)
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- Arylalkylamine vanadium (V) salts for the treatment and/or prevention of Diabetes mellitus
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This invention provides compounds of formula (IIA) and pharmaceutical compositions thereof, where M, a, b, and R1-R5 are as defined herein, for treating human type 1 and type 2 diabetes, particularly insulin-resistant diabetes. Pharmaceutical compositions comprising the compounds of formula (IIA) are also disclosed.
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Page/Page column 19; 20
(2010/11/26)
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- Process for the preparation of amino compounds containing an aromatic ring by using a shell-type catalyst
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An aromatic dinitrile compound is hydrogenated in an amide solvent in the presence of a solid catalyst and in the absence of ammonia to produce an aromatic ring-containing amino compound by reducing at least one cyano group to aminomethyl group. The solid catalyst is a supported palladium catalyst in which palladium is substantially present on the outer surface of carrier and in a surface layer within a depth of 200 μm from the outer surface. Using such a solid catalyst, the aromatic dinitrile compound is efficiently hydrogenated to the aromatic ring-containing amino compound under mild conditions.
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Page/Page column 7-8
(2008/06/13)
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- METHOD FOR PRODUCING A XYLYLENE DIAMINE
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The invention relates to a method for producing a xylylene diamine by the heterogeneously catalysed hydration of a phthalodinitrile. According to the invention, the hydration is carried out in the presence of a cobalt skeleton catalyst, an alkali metal hydroxide and an alcohol and/or ether as the solvent, at an absolute pressure ranging between 1 and 100 bar and a temperature of between 40 and 150 °C.
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Page/Page column 8-9
(2008/06/13)
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- METHOD FOR PRODUCING A XYLYLENEDIAMINE
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The invention relates to a method for producing a xylylenediamine by the heterogeneously catalysed hydrogenation of a phthalodinitrile. According to the invention, said hydrogenation is carried out in the presence of a nickel skeleton catalyst, water, an alkali metal hydroxide and an ether, which acts as the solvent, at an absolute pressure ranging from 1 to 100 bar, a temperature of between 40 and 150 °C and without the addition of ammonia.
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Page/Page column 10
(2008/06/13)
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- METHOD FOR THE PRODUCTION OF DIAMINOXYLENE BY CONTINUOUS HYDROGENATION OF LIQUID PHTHALONITRILE
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The invention relates to a method for the production of diaminoxylene, by continuous hydrogenation of liquid phthalonitrile, on a heterogeneous catalyst, in the presence of liquid ammonia, in a reactor, whereby a part of the reactor product is continuously recycled to the reactor feed as a liquid recycle stream (recirculating loop). A flow of fused phthalonitrile is added as a liquid to the recycle stream around the hydrogenation reactor in a mixing device, whereby the phthalonitrile conversion in the reactor on a single pass is greater than 99 % and the recycle stream comprises more than 93 % by weight of liquid ammonia and diaminoxylene and contains no further solvent for phthalonitrile.
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Page/Page column 9
(2008/06/13)
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- METHOD FOR PRODUCING XYLYLENEDIAMINE
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PROBLEM TO BE SOLVED: To provide a method for efficiently converting a xylylenediamine condensate formed as a by-product in a catalytic hydrogen reduction of dicyanobenzene or a reductive catalytic hydrogenation reaction of phthalaldehyde into the xylylenediamine. SOLUTION: The method for producing the xylylenediamine is characterized as follows. The xylylenediamine condensate is reacted with ammonia and hydrogen in the presence of a catalyst (a catalyst for degrading the condensate) containing at least one kind of metal selected from nickel, cobalt, iron, copper, ruthenium, palladium and rhodium.
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Page/Page column 7-8
(2008/06/13)
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- High-selective production method of di(aminomethyl)-substituted aromatic compound
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A di(aminomethyl)-substituted aromatic compound is produced by a two-stage hydrogenation. In the first stage, an aromatic dinitrile is hydrogenated into a cyano(aminomethyl)-substituted aromatic compound in the presence of a Pd-containing catalyst. The resultant cyano(aminomethyl)-substituted aromatic compound is then hydrogenated in the second stage into the target di(aminomethyl)-substituted aromatic compound in the presence of a Ni- and/or Co-containing catalyst. By the above method, the di(aminomethyl)-substituted aromatic compound is produced in a high selectivity and a sufficiently high yield without reducing the catalyst life.
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- Process for production of xylylenediamine and/or cyanobenzylamine
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In the process of the present invention, xylylenediamine and/or cyanobenzylamine is produced by a catalytic liquid-phase hydrogenation of a phthalonitrile compound. The liquid-phase hydrogenation is performed by controlling the concentration of a benzamide compound to a specific level or lower. In a preferred embodiment, the concentration of a benzoic acid compound is further controlled to a specific level or lower. By the process, xylylenediamine and/or cyanobenzylamine is produced at high yields and the catalyst life is prolonged.
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- Production method of xylylenediamine
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In the method of the present invention, xylylenediamine is produced by a two-stage hydrogenation of a dicyanobenzene compound. In a first stage (a), the hydrogenation is performed until a conversion of nitrile groups reaches 90 mol% or higher and less than 99.9 mol%. In a second stage (b), the hydrogenation is further continued at temperatures 10°C or more higher than in the step (a) until the conversion of nitrile groups reaches a level which is higher than that attained in the step (a) and equal to 99.5 mol% or more. In the present invention, a highly pure xylylenediamine containing a minimized amount of cyanobenzylamine is efficiently produced in a simple manner without needing a specific purification, and also without deteriorating the use efficiency of the catalyst while reducing the amount of the dicyanobenzene compound remaining not reacted and the generation of the intermediate cyanobenzylamine.
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- Process for production of xylylenediamine
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In the process of the present invention for producing a xylylenediamine by a liquid-phase hydrogenation of a dicyanobenzene in the presence of a catalyst, the catalyst having its activity decreased during the course of use in the hydrogenation is reactivated and a pressure drop through a fixed bed catalyst layer is got rid of, thereby regenerating the catalyst for reuse in the subsequent hydrogenation of the dicyanobenzene to produce the xylylenediamine. The catalyst is regenerated by brought into contact with a hydrogen-containing gas under controlled temperature conditions.
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- Tetracyclic benzimidazole derivatives and combinatorial libraries thereof
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The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.
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- Process for producing aromatic primary amine by low-pressure
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A method for producing an aromatic primary amine, characterized by hydrogenating an aromatic nitrile at a low partial pressure of hydrogen in a heterogeneous system comprising a non-reductive polar solvent and a nickel-immobilized catalyst suspended therein was proposed. By such method, an aromatic primary amine which is industrially useful as a medicine, agricultural chemical, dye surfactant, chemical agent, etc. can be produced in a high yield.
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- Supported nickel-catalyzed hydrogenation of aromatic nitriles under low pressure conditions
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Hydrogenation of aromatic nitriles takes place under the mild conditions using supported nickel catalysts to afford amino-methyl-substituted aromatics in good yields.
- Takamizawa,Wakasa,Fuchikami
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p. 1623 - 1625
(2007/10/03)
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- Synthesis of phthalonitrile resins containing ether and imide linkages
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Imide-containing phthalonitrile monomers are prepared from a phthalonitrile and an aromatic dianhydride. The monomer and a method for preparing the monomer is disclosed. These monomers are synthesized into heat resistant polymers and copolymers with aromatic ring structure incorporating imide and ether linkages. The synthesis of the high temperature thermosetting polymers and copolymers is also disclosed.
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