646-25-3Relevant articles and documents
One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
Coeck, Robin,De Vos, Dirk E.
supporting information, p. 5105 - 5114 (2020/08/25)
The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
Sustainable hydrogenation of aliphatic acyclic primary amides to primary amines with recyclable heterogeneous ruthenium-tungsten catalysts
Coeck, Robin,Berden, Sarah,De Vos, Dirk E.
supporting information, p. 5326 - 5335 (2019/10/11)
The hydrogenation of amides is a straightforward method to produce (possibly bio-based) amines. However current amide hydrogenation catalysts have only been validated in a rather limited range of toxic solvents and the hydrogenation of aliphatic (acyclic) primary amides has rarely been investigated. Here, we report the use of a new and relatively cheap ruthenium-tungsten bimetallic catalyst in the green and benign solvent cyclopentyl methyl ether (CPME). Besides the effect of the Lewis acid promotor, NH3 partial pressure is identified as the key parameter leading to high primary amine yields. In our model reaction with hexanamide, yields of up to 83% hexylamine could be achieved. Beside the NH3 partial pressure, we investigated the effect of the catalyst support, PGM-Lewis acid ratio, H2 pressure, temperature, solvent tolerance and product stability. Finally, the catalyst was characterized and proven to be very stable and highly suitable for the hydrogenation of a broad range of amides.
High-carbon alkane diamine, and preparation method and application thereof
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Paragraph 0077; 0080-0082, (2019/03/28)
The invention relates to the field of high-carbon alkane diamine preparation, and discloses high-carbon alkane diamine, and a preparation method and application thereof. The preparation method of thehigh-carbon alkane diamine disclosed by the invention is characterized in that the structure of the high-carbon alkane diamine is as shown in the formula NH2-(CH2)m-NH2; the method comprises the following steps: (1) under amideation reaction conditions, reacting high-carbon alkane diacid which is as shown in the formula COOH-(CH2)n-COOH with an ammonia-containing compound to obtain high-carbon chain diamide which is as shown in the formula CONH2-(CH2)n-CONH2; (2) under an alkaline condition, enabling the high-carbon chain diamide which is as shown in the formula CONH2-(CH2)n-CONH2 to perform rearrangement degradation in the existence of water, sodium hypochlorite and/or sodium hypobromite to obtain the high-carbon alkane diamine which is as shown in the formula NH2-(CH2)m-NH2, wherein n=11to 15, and m=9 to 13. The method provided by the invention is a safe, convenient, simple and feasible preparation method for the high-carbon alkane diamine.