A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines

Abstract

A new and selective route for the synthesis of polymer precursors, primary diamines or N-substituted diamines, from dicarboxylic acids, diesters, diamides and diols using a Ru/triphos catalyst is reported.

Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis

“…It is noteworthy that the thus‐obtained fatty amines are an important class of chemicals for the industrial production of surfactants, germicides, and softeners. Although the reductive amination of relatively reactive carbonyl compounds such as ketones and aldehydes into amines has been studied extensively, reports on the reductive amination of carboxylic acids and esters including triglycerides remain relatively rare . Our heterogeneous catalytic system using NH 3 as a nitrogen source and H 2 does not require any additives and could thus serve as an effective method for the direct transformation of triglycerides into fatty amines.…”

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

“…They performed the hydrogenation of nonanoic acid in the presence of NH 3 to give a mixture of Noctylamines 55,56 . After this example, interesting developments in this area have been made by the groups of Cantat 138 , Beller (2015, 2016, and 2018) [139][140][141][142] , Cole-Hamilton (2017) 143,144 , and Sundararaju 145 . In all these cases, the active catalyst employed Triphos (Fig.…”

Diamines for Polymer Materials via Direct Amination of Lipid‐ and Lignocellulose‐based Alcohols with NH3

“…[34,[36][37][38][39] Alcohols and alcohol derivatives (ketones, aldehydes) are easily accessible already from biomass and can be exploited in the synthesis of amines via the direct amination of alcohols with NH 3 .T he reactionf ollowst he so-called "Hydrogen Shuttling" or "Borrowing Hydrogen" methodology withw ater as the only by-product (Scheme 2). [46,47,51] This is, however,crucial as it is also as ensitive probe whether the amination reactioni s sufficiently selective and the formation of problematic (e.g. [40][41][42][43][44][45] However,o nly two exampleso fal ong-chain diol direct amination have been reported, both for the case of 1,19-nonadecane diol, and the conversion of the product to polymers as ap robe of their suitability to this purposehas been lacking.…”

“…[40][41][42][43][44][45] However,o nly two exampleso fal ong-chain diol direct amination have been reported, both for the case of 1,19-nonadecane diol, and the conversion of the product to polymers as ap robe of their suitability to this purposehas been lacking. [46,47,51] This is, however,crucial as it is also as ensitive probe whether the amination reactioni s sufficiently selective and the formation of problematic (e.g. mono-functional) side-products is below an appreciable limit.…”