101-83-7Relevant articles and documents
A Direct Correlation between Dispersion, Metal Area, and Vapour Phase Hydrogenation of Aniline; a First Report
Vishwanathan, Venkataraman,Narayanan, Sankarasubbier
, p. 78 - 80 (1990)
Aniline hydrogenation activity is correlated with dispersion, crystallite size, and metal area over Rh/Al2O3 catalyst.
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Jackson,Sasse
, p. 3746,3747 (1962)
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Vapor-Phase Amination of Cyclohexanol over Silica-Supported Platinum Group Metal Catalysts
Hamada, Hideaki,Kuwahara, Yasushi,Sato, Takahiro,Wakabayashi, Katsuhiko
, p. 55 - 60 (1987)
Vapor-phase amination of cyclohexanol with ammonia over silica-supported platinum and other platinum group metal (Ru, Rh, Pd, Ir) catalysts has been studied.Cyclohexylamine and aniline are the main products.Platinum is the most active metal, although ther
Comparison of hydrogen adsorption and aniline hydrogenation over co-precipitated Co/Al2O3 and Ni/Al2O3 catalysts
Narayanan, Sankarasubbier,Unnikrishnan, Ramachandran Pillai
, p. 2009 - 2013 (1997)
Co/Al2O3 catalysts with different cobalt content (10-50 wt.%) have been prepared by a co-precipitation method at pH 8. The catalysts were characterised by physical measurements (pore volume, bulk density, surface area and XRD) and by
An efficient heterogenized palladium catalyst for N-alkylation of amines and α-alkylation of ketones using alcohols
Dang, Tuan Thanh,Shan, Siah Pei,Ramalingam, Balamurugan,Seayad, Abdul Majeed
, p. 42399 - 42406 (2015)
A silica supported palladium-NiXantphos complex is reported as an efficient and a high turnover heterogeneous catalyst for the N-alkylation of amines and the α-alkylation of ketones using readily available alcohols under neat conditions at 120-140 °C following hydrogen borrowing strategy. The catalyst is easily separable and offers negligible amount of palladium leaching (0.01 ppm). A high turnover number of about 46000 for the N-alkylation of amines and 4400 for the α-alkylation of ketones were achieved in the respective single batch reactions. The catalyst is recyclable up to four times without appreciable change in catalytic performance.
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Baker,Schuetz
, p. 1250 (1947)
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Selective synthesis of octahydroacridines and diannelated pyridines over zinc-containing mesoporous aluminosilicate molecular sieve catalysts
Selvaraj, Manickam,Assiri, Mohammed A.
, p. 12986 - 12995 (2019)
We demonstrate a very eco-friendly and single-step catalytic method for the highly selective synthesis of 1,2,3,4,5,6,7,8-octahydroacridine (OHA) by the vapour phase aminocyclization of cyclohexanone (CyO) with a mixture of formaldehyde (HCHO) and ammonia (NH3) over mesoporous bimetallic ZnAlMCM-41 (ZnAl-41) molecular sieves as efficient catalysts, which were synthesised by a simple basic hydrothermal method. To find optimum parameters for the synthesis of OHA, different reaction parameters, such as temperature, time on stream (TOS), weight hourly space velocity (WHSV), and feed molar ratios of CyO:HCHO:NH3, have been extensively studied. The used ZnAl-41 catalysts were treated by washing and calcination to recover the recyclable catalysts which were then reused in these reactions to study their catalytic abilities. To selectively synthesize a variety of pyridine compounds, the active mesoporous catalysts, namely, ZnAl-41(75) and recyclable ZnAl-41(75), with different reaction parameters, were extensively used in the vapour phase aminocyclization reaction with different aldehydes and cycloketones, and produced excellent product selectivities, e.g., 9-alkyl substituted octahydroacridines (9-ASOHAs) and diannelated pyridines (DAPs), with good ketone conversions. In this catalytic reaction, OHA, 9-ASOHAs and DAPs are the main products and are important as starting materials in the preparation of biologically active compounds, drugs, dyes and alkaloids. It is shown by our remarkable catalytic results that the ZnAl-41(75) catalyst, as an environmentally friendly heterogeneous catalyst, has outstanding catalytic activity in the production of OHA, 9-ASOHAs and DAPs by a single-step synthetic method.
RAPID AND EFFICIENT REDUCTION OF ALIPHATIC NITRO COMPOUNDS TO AMINES
Osby, John O.,Ganem, Bruce
, p. 6413 - 6416 (1985)
The combination of NaBH4 with catalytic quantities of NiCl2 smoothly reduces aliphatic nitro compounds to amines in methanol; Ni2B formed in situ is the active catalyst.
An improved method for the complete hydrogenation of aromatic compounds under 1 bar H2 with platinum nanowires
Yu, Tingting,Wang, Jiaqing,Li, Xinming,Cao, Xueqin,Gu, Hongwei
, p. 2852 - 2855 (2013)
A little pressure for a lot of gain: An efficient method has been developed for the controlled hydrogenation of phenol using a platinum nanowire catalyst under mild conditions (>98.4%, 1atm H2, 60°C). The catalyst also exhibited high levels of activity and selectivity towards other selected aromatic compounds bearing a variety of different substituents, demonstrating its generality towards the hydrogenation of aromatic compounds.
Chemoselective deprotection of N-allylic amines using DDQ
Kumar, Pradeep,Cherian, Shijo K.,Jain, Ruchi,Show, Krishanu
, p. 7172 - 7176 (2014)
A highly chemoselective and simple method for the deprotection of N-allylic amines using DDQ has been developed. The use of DDQ in dichloromethane-water provides a mild and efficient one-step deallylation of a wide variety of orthogonally protected tertiary amine derivatives.
Hydrogenation of aniline to cyclohexylamine in supercritical carbon dioxide: Significance of phase behaviour
Chatterjee,Sato,Kawanami,Ishizaka,Yokoyama,Suzuki
, p. 186 - 193 (2011)
Hydrogenation of aniline to cyclohexylamine was carried out in supercritical carbon dioxide using a variety of noble metal (Pt, Pd and Rh) catalysts. At 80 °C and 8 MPa of CO2 pressure, >95% of aniline conversion with 93% selectivity to cyclohexylamine was achieved on 5% Rh/Al2O3. A strong influence of phase behaviour related to the CO2 pressure was found on the conversion and selectivity. Optimization of reaction parameters resulted in a higher overall activity in the biphase (liquid substrate + gaseous H2 and CO2) than in the single phase (liquid substrate-CO2-H2) condition. It has been found that the interaction of CO2 with amine leads to the formation of solid carbamic acid, which enhanced the selectivity of cyclohexylamine, but reduced the conversion significantly. Furthermore, reaction temperature played a crucial role in preventing the formation of carbamic acid and also maintained a reasonably high reaction performance in terms of conversion and selectivity.
Formation of secondary or tertiary aliphatic amines in aqueous media
Marieta Simion, Alina,Arimura, Takashi,Miyazawa, Akira,Simion, Cristian,Surya Prakash,Olah, George A.,Tashiro, Masashi
, p. 2859 - 2865 (2009)
Secondary and tertiary amines can be easily obtained from primary and secondary amines, respectively, in completely aqueous media, in the presence of a bicatalytic system formed of cheap commercial aluminum (Al) powder and 5% rhodium (Rh) or ruthenium (Ru) deposed on charcoal.
Transformylating amine with DMF to formamide over CeO2 catalyst
Wang, Yehong,Wang, Feng,Zhang, Chaofeng,Zhang, Jian,Li, Mingrun,Xu, Jie
, p. 2438 - 2441 (2014)
We here report a new protocol for the formylation of various amines, primary or secondary, aromatic or alkyl, cyclic or linear, mono- or di-amine, with dimethylformamide (DMF) as the formylation reagent to obtain the corresponding formamides in good to excellent yields over CeO2 catalyst. The reaction requires no homogeneous acidic or basic additives and is tolerant to water.
TRICHLOROSILANE-IMINE COMPLEXES. A NEW METHOD FOR THE REDUCTION OF IMINES TO AMINES
Benkeser, Robert A.,Snyder, Dudley C.
, p. 107 - 115 (1982)
It has been found that trichlorosilane adds regio-specifically to the carbon-nitrogen double bond of imines under mild conditions to yield hydrolytically unstable N-trichlorosilyl intermediates.The latter can be hydrolyzed in situ by alcoholic base to give the corresponding amines in moderate to good yields.Variously substituted aldo and keto imines, both alkyl and aryl, were tested to demonstrate the scope of the reaction.The facility of trichlorosilane addition appears to depend on the nature of the groups directly attached to the carbon-nitrogen double bond.Hydride trapping experiments suggest an intramolecular rather than intermolecular hydride transfer during the course of the reaction.
Molecular Assembly Line: Stepwise Hydrogenation of Multifunctional Substrates over Catalyst Mixtures
Tomkins, Patrick,Gebauer-Henke, Ewa,Müller, Thomas E.
, p. 546 - 550 (2016)
The synthesis of many chemical products requires multiple steps. To simplify the overall synthesis by combining consecutive reaction steps, the concept of a molecular assembly line promises to yield high reaction rates and selectivities. In this study, mixtures of carbon nanotube (CNT)-supported catalysts were used to demonstrate the potential of this concept on hand of the hydrogenation of nitrobenzene via aniline to cyclohexylamine. Mixtures of Pt/CNT, having a high activity in nitrobenzene hydrogenation, and of Ru/CNT, highly selective for the hydrogenation of aniline to cyclohexylamine, provided high activity at constant high selectivity. Varying the Pt:Ru ratio to 5:95 was found to be the best case scenario, for which the rates of the two consecutive reaction steps are balanced. The use of catalyst mixtures rather than bimetallic catalysts avoids complex phenomena such as phase separation or migration of one of the metals to the surface of the bimetallic particles.
Borohydride exchange resin, a new reducing agent for reductive amination
Yoon,Kim,Son,Choi
, p. 1595 - 1599 (1993)
Borohydride Exchange Resin is a useful, convenient reducing agent for the reductive amination of aldehydes and ketones in alcoholic solvent.
Self-coupling of benzylamines over a highly active and selective supported copper catalyst to produce N-substituted amines by the borrowing hydrogen method
Liu, Huihui,Chuah, Gaik-Khuan,Jaenicke, Stephan
, p. 262 - 268 (2015)
Amines were used as hydrogen donor for the borrowing hydrogen methodology with a heterogeneous catalyst. Supported copper catalysts catalyzed the self-condensation reaction of primary amines to secondary amines/imines with high efficiency. The recyclable, non-leaching catalyst is synthesized by a sol-gel method, which allows entrapping copper nanoparticles in an alumina matrix. The synthesized copper catalysts were found to be active in the self-coupling of primary amines to produce secondary amines. The hydrogen donor for the transfer hydrogenation appears to be the primary amine, and no additional hydrogen or hydrogen transfer reagent is required. To the best of our knowledge, this is the first report of a copper based catalyst for this type of reaction using the borrowing hydrogen scheme.
The Co-amination of Phenol and Cyclohexanol with Palladium-on-carbon Catalyst in the Liquid Phase. An Application of a Hydrogen-transfer Reaction
Hamada, Hideaki,Yamamoto, Makoto,Kuwahara, Yasushi,Matsuzaki, Takehiko,Wakabayashi, Katsuhiro
, p. 1551 - 1555 (1985)
Phenol and Cyclohexanol are simultaneously aminated to aniline and cyclohexylamine by ammonolysis with the palladium-on-carbon catalyst in the liquid phase, although the amination of either phenol or cyclohexanol hardly occurs without the other.In contras
A FACILE SYNTHESIS OF SYMMETRICAL SECONDARY AMINES FROM PRIMARY AMINES PROMOTED BY THE HOMOGENEOUS CATALYST RuCl2(Ph3P)3
Bui-The-Khai,Concilio, Carlo,Porzi, Gianni
, p. 249 - 251 (1981)
Primary amines bearing an α-hydrogen atom are quantitatively converted to symmetrical secondary amines by heating at 185 deg C for 5 h in the presence of a catalytic amount of RuCl2(Ph3)3.
Chemical Conversions using Sheet Silicates: Novel Intermolecular Elimination of Ammonia from Amines
Ballantine, James A.,Purnell, Howard,Rayanakorn, Mongkon,Thomas, John M.,Williams, Kevin J.
, p. 9 - 10 (1981)
Ammonia is readily eliminated from molecular pairs of intercalated primary amines thereby generating the secondary amines in high yield in a novel proton-mediated reaction; certain cyclic secondary amines produce unusual products by a similar interlamellar reaction.
Highly efficient heterogeneous gold-catalyzed direct synthesis of tertiary and secondary amines from alcohols and urea
He, Lin,Qian, Yue,Ding, Ran-Sheng,Liu, Yong-Mei,He, He-Yong,Fan, Kang-Nian,Cao, Yong
, p. 621 - 624 (2012)
Urea, the white gold: The efficient synthesis of tertiary and secondary amines is achieved by heterogeneous gold-catalyzed direct amination of stoichiometric alcohols with urea in good to excellent yields. Via a hydrogen autotransfer pathway, the reactions of primary alcohols with urea give tertiary amines exclusively, while secondary alcohols selectively afford secondary amines.
Aromatic compound hydrogenation and hydrodeoxygenation method and application thereof
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Paragraph 0094-0096; 0098; 0100-0104, (2021/05/29)
The invention belongs to the technical field of medicines, and discloses an aromatic compound hydrogenation and hydrodeoxygenation method under mild conditions and application of the method in hydrogenation and hydrodeoxygenation reactions of the aromatic compounds and related mixtures. Specifically, the method comprises the following steps: contacting the aromatic compound or a mixture containing the aromatic compound with a catalyst and hydrogen with proper pressure in a solvent under a proper temperature condition, and reacting the hydrogen, the solvent and the aromatic compound under the action of the catalyst to obtain a corresponding hydrogenation product or/and a hydrodeoxygenation product without an oxygen-containing substituent group. The invention also discloses specific implementation conditions of the method and an aromatic compound structure type applicable to the method. The hydrogenation and hydrodeoxygenation reaction method used in the invention has the advantages of mild reaction conditions, high hydrodeoxygenation efficiency, wide substrate applicability, convenient post-treatment, and good laboratory and industrial application prospects.
One-pot synthesis of cyclohexylamine and: N -aryl pyrroles via hydrogenation of nitroarenes over the Pd0.5Ru0.5-PVP catalyst
Chaudhari, Chandan,Sato, Katsutoshi,Ikeda, Yasuyuki,Terada, Kenji,Abe, Naoya,Nagaoka, Katsutoshi
supporting information, p. 9743 - 9746 (2021/06/15)
The direct synthesis of cyclohexylamine via the hydrogenation of nitrobenzene over monometallic (Pd, Ru or Rh) and bimetallic (PdxRu1-x) catalysts was studied. The Pd0.5Ru0.5-PVP catalyst was the most effective catalyst for this reaction. The catalyst can be reused and applied for the synthesis of N-aryl pyrroles and quinoxalines from nitrobenzenes.
