10576-04-2

Upstream product

• 124-12-9 caprylnitrile 
• 1120-48-5 n-dioctylamine 
• 111-86-4 n-Octylamine 
• 111-87-5 octanol 
• 1116-76-3 Tri-n-octylamine 
• 124-13-0 Octanal 

Downstream Products

• 124-13-0 Octanal 
• 1726-77-8 octanal (2,4-dinitrophenyl)hydrazone 
• 2296-14-2 dioctylamine hydrochloride 
• 5851-49-0 2-heptyl-1H-benzoimidazole 
• 1120-48-5 n-dioctylamine 

Relevant academic research and scientific papers

Dehydrogenation of amines to nitriles in aqueous micelles

An aqueous reaction medium, based on a surfactant solution of dimethyldodecylamine N-oxide (DDAO) has been developed for the oxidative dehydrogenation of primary amines using NiSO4 as catalyst and K 2S2O8 as oxidant. This reaction medium enhances the rate of the reaction relative to other media previously reported in the literature, which are also toxic. The reactions of various aliphatic and cyclic amines have been investigated and gave nitriles with yields of >90% in mild conditions. The aqueous surfactant solution and reagents were recycled for future use. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Nanoceria-promoted low Pd-Ni catalyst for the synthesis of secondary amines from aliphatic alcohols and ammonia

This paper describes the preparation of a series of bimetallic Pd-Ni catalysts supported over nanoceria with very low Ni and Pd loading (2-TPR, H2-TPD, STEM-EDS-SDD and XPS. The sequence of impregnation of both metals and the Pd loading affected to an important extent the catalytic activity by conditioning the crystallite size and the Pd and Ni speciation, as well as the reducibility and reversible H2 storage properties. By optimizing the preparation protocols, a 0.5wt% Pd-0.5wt% Ni-Pd/CeO2 formulation prepared by sequential impregnation of the nickel and palladium precursors afforded 80% yield of dioctylamine at almost full conversion [TON = 1160 mmol per mmol (Ni + Pd)surface] in the direct amination reaction of 1-octanol with ammonia at 180 °C for 2 h. Metal leaching during the reaction could be completely avoided. The high catalytic performance of Pd-Ni induced by nanoceria places this catalyst among the best ever reported catalysts for the synthesis of secondary amines.

Preparation of nitrogen-doped carbon supported cobalt catalysts and its application in the reductive amination

The use of non-noble metal catalysts with high activity is of great importance for organic transformations. Herein, nitrogen-doped carbon supported cobalt catalysts with high surface area up to 981.2 m2/g were prepared via the simple pyrolysis of cobalt coordinated organic polymers with silica as the hard template. The pyrolysis temperature showed a great effect on the structure and properties of the as-prepared catalysts. The Co@NC-800 catalyst with the pyrolysis temperature of 800 °C demonstrated a high activity for the selective reductive amination of carbonyl compounds to primary amines with ammonia and hydrogen. Structurally-diverse primary amines with yields in the range from 81.8% to 100% were attained under the optimal conditions. The Co@NC-800 catalyst could be reused without the loss of its activity. The Co@NC-800 catalyst demonstrated comparable activity as the reported heterogeneous noble metal catalysts.

Direct synthesis of nitriles by Cu/DMEDA/TEMPO-catalyzed aerobic oxidation of primary amines with air

By screening the copper catalysts, ligands, and the reaction conditions, a simple CuCl/DMEDA/TEMPO catalyst system readily available from commercial sources is developed for a direct and selective synthesis of the useful nitriles by an aerobic oxidation reaction of primary amines using air as an advantageous oxidant under mild conditions.

A ruthenium racemisation catalyst for the synthesis of primary amines from secondary amines

A Ru-based half sandwich complex used in amine and alcohol racemization reactions was found to be active in the splitting of secondary amines to primary amines using NH3. Conversions up to 80% along with very high selectivities were achieved. However, after about 80% conversion the catalyst lost activity. Similar to Shvo's catalyst, the complex might deactivate under the influence of ammonia. It was revealed that not NH3 but mainly the primary amine is responsible for the deactivation.

Catalytic Hydrogen Production by Ruthenium Complexes from the Conversion of Primary Amines to Nitriles: Potential Application as a Liquid Organic Hydrogen Carrier

The potential application of the primary amine/nitrile pair as a liquid organic hydrogen carrier (LOHC) has been evaluated. Ruthenium complexes of formula [(p-cym)Ru(NHC)Cl2] (NHC=N-heterocyclic carbene) catalyze the acceptorless dehydrogenation of primary amines to nitriles with the formation of molecular hydrogen. Notably, the reaction proceeds without any external additive, under air, and under mild reaction conditions. The catalytic properties of a ruthenium complex supported on the surface of graphene have been explored for reutilization purposes. The ruthenium-supported catalyst is active for at least 10 runs without any apparent loss of activity. The results obtained in terms of catalytic activity, stability, and recyclability are encouraging for the potential application of the amine/nitrile pair as a LOHC. The main challenge in the dehydrogenation of benzylamines is the selectivity control, such as avoiding the formation of imine byproducts due to transamination reactions. Herein, selectivity has been achieved by using long-chain primary amines such as dodecylamine. Mechanistic studies have been performed to rationalize the key factors involved in the activity and selectivity of the catalysts in the dehydrogenation of amines. The experimental results suggest that the catalyst resting state contains a coordinated amine.

Tuneable hydrogenation of nitriles into imines or amines with a ruthenium pincer complex under mild conditions

The selective hydrogenation of aromatic and aliphatic nitriles into amines and imines is described. Using a ruthenium pincer complex, the selectivity towards amines or imines can be controlled by simple parameter changes. The reactions are conducted under very mild conditions between 50-100°C at 0.4 MPa H2 pressure without any additives at low catalytic loadings of 0.5-1 mol %, which results in quantitative conversions and high selectivity.

Alcohol amination with heterogeneous ruthenium hydroxyapatite catalysts

The intermolecular amination of alcohols was performed with ruthenium (Ru3+) immobilized on a calcium hydroxyapatite support. No additional base additives were necessary, nor did the catalyst require base treatment prior to reaction. High conversions were obtained with different amine and alcohol reactants.

Cu(I)/TEMPO-catalyzed aerobic oxidative synthesis of imines directly from primary and secondary amines under ambient and neat conditions

By catalyst and condition screening, a simple Cu(I)/TEMPO-catalyst system was found to be an active and highly effective catalyst for the aerobic oxidation of amines to imines in open air at room temperature under neat conditions. This new method provided a mild, efficient, and practical alternative for the synthesis of the useful imines directly from primary and secondary amines.

Oxidation of amines over alumina based catalysts

Amines were oxidized by molecular oxygen in the vapor phase at atmospheric pressure over alumina and silicotungstic acid/alumina catalysts. The study is focused on the influence of structure of amine and catalyst properties on the composition of the main reaction products and byproducts. Coating of γ-Al2O3 with silicotungstic acid or its semisalt can significantly enhance its catalytic activity in amine oxidation. The adsorption of amine on weak acidic sites of catalyst is essential for its oxidation to main reaction products. Cycloalkylamines are oxidized mainly to cyclic oximes (selectivity up to 64%) and Schiff bases of appropriate cycloalkanone and cycloalkylamine (selectivity up to 38%). Mainly nitriles (selectivity up to 55%) and appropriate Schiff bases (selectivity up to 54%) were observed in the oxidation products of primary alkylamines. Their molar ratio depends on the catalyst acidity and reaction conditions. 1,6-Hexanediamine is oxidized mainly to caprolactam (yield 48%) and other cyclic lactames and Schiff bases as well as to dinitrile (yield 13%).