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.
Pd/TiO2-Photocatalyzed Self-Condensation of Primary Amines to Afford Secondary Amines at Ambient Temperature
Wang, Lyu-Ming,Kobayashi, Kensuke,Arisawa, Mitsuhiro,Saito, Susumu,Naka, Hiroshi
, p. 341 - 344 (2019)
Symmetric secondary amines were synthesized by the self-condensation of primary amines over a palladium-loaded titanium dioxide (Pd/TiO2) photocatalyst. The reactions afforded a series of secondary amines in moderate to excellent isolated yields at ambient temperature (30 °C, in cyclopentyl methyl ether). Applicability for one-pot pharmaceutical synthesis was demonstrated by a photocatalytic reaction sequence of self-condensation of an amine followed by N-alkylation of the resulting secondary amine with an alcohol.
Selective reduction of halo-nitro aromatic compounds using [Rh]/DHTANa as catalyst in an aqueous bi-phase system
Rathod, Vikas Damu,Paganelli, Stefano,Piccolo, Oreste
, p. 52 - 55 (2016)
The use of water as co-solvent for biphasic reactions and of easily recyclable water-soluble catalysts are highly desirable for the realization of greener processes. The selective reduction of halo nitroarenes to the corresponding haloanilines is a very important industrial transformation for the production of agrochemicals, pigments, bactericides and pharmaceuticals and is not easy to obtain. The application of a water soluble catalyst, prepared by rhodium species and a cheap thioligand, in the hydrogenation of some halonitroarenes is here described. Excellent conversions, good recyclability of the catalytic species embedded in the aqueous phase and very high selectivity are demonstrated.
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.
Concurrent Hydrogenation of Aromatic and Nitro Groups over Carbon-Supported Ruthenium Catalysts
Tomkins, Patrick,Gebauer-Henke, Ewa,Leitner, Walter,Müller, Thomas E.
, p. 203 - 209 (2015)
The concurrent hydrogenation of aromatic and nitro groups poses particular challenges due to the highly differing adsorption strengths of the two chemical moieties on the surfaces of metal catalysts. In a study of the hydrogenation of nitrobenzene as a model reaction, catalysts of ruthenium supported on carbon nanotubes (Ru/CNT) provided an ideal compromise, allowing for hydrogenation of both the aromatic ring and the nitro group. The use of methyl-labeled substrates enabled tracking the pathway of specific substrates and obtaining insight into the relative rates for the hydrogenation of nitrobenzene and intermediates. Together with findings on the coadsorption of nitrobenzene and aniline on the Ru/CNT catalyst, an advanced mechanistic model for the hydrogenation of nitrobenzene emerges. (Chemical Equation Presented).
Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines
Cuypers, Thomas,Morias, Thomas,Windels, Simon,Marquez, Carlos,Van Goethem, Cédric,Vankelecom, Ivo,De Vos, Dirk E.
, p. 1884 - 1893 (2020)
Phenol and its derivatives, which naturally occur in lignocellulose, can be considered as a renewable feedstock not only for aromatic, but also for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without using any additives. Various supported Ni catalysts were screened and we elucidated the influence of the key parameters, including the acid-base properties of the supporting material. Acquired knowledge was then applied to different phenol-ammonia/amine combinations, resulting in the synthesis of various primary, secondary and tertiary cyclohexylamines in fair to very high yields.
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.
