1822-45-3Relevant articles and documents
-
Moshier,Spialter
, p. 1050 (1956)
-
Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis
Pelckmans, Michiel,Vermandel, Walter,Van Waes, Frederik,Moonen, Kristof,Sels, Bert F.
, p. 14540 - 14544 (2017/10/23)
Short amines, such as ethanolamines and ethylenediamines, are important compounds in today's bulk and fine chemicals industry. Unfortunately, current industrial manufacture of these chemicals relies on fossil resources and requires rigorous safety measures when handling explosive or toxic intermediates. Inspired by the elegant working mechanism of aldolase enzymes, a novel heterogeneously catalyzed process—reductive aminolysis—was developed for the efficient production of short amines from carbohydrates at low temperature. High-value bio-based amines containing a bio-derived C2 carbon backbone were synthesized in one step with yields up to 87 C%, in the absence of a solvent and at a temperature below 405 K. A wide variety of available primary and secondary alkyl- and alkanolamines can be reacted with the carbohydrate to form the corresponding C2-diamine. The presented reductive aminolysis is therefore a promising strategy for sustainable synthesis of short, acyclic, bio-based amines.
Preparation of peralkylated amines
-
, (2008/06/13)
A process for the preparation of peralkylated amines of the general formula I STR1 in which R1, R2 denote C1 -C200 alkyl, C3 -C8 cycloalkyl, C4 -C20 alkylcycloalkyl, C4 -C20 cycloalkylalkyl, C2 -C20 alkoxyalkyl, aryl, C7 -C20 alkylaryl, C7 -C20 aralkyl, C2 -C8 hydroxyalkyl, C2 -C8 mercaptoalkyl, C8 -C20 phenoxyalkyl, C2 -C8 aminoalkyl, C2 -C8 (NHR4)alkyl, C2 -C8 (NR4 R5)alkyl or together form a saturated or unsaturated C2 -C6 alkylene chain optionally mono- to tri-substituted by C1 -C4 alkyl and optionally interrupted by oxygen or nitrogen X denotes a C2 -C20 alkylene or C2 -C20 alkenylene or C4 -C8 cycloalkylene chain optionally mono- to penta-substituted by R3, C1 -C8 alkyl, C1 -C8 alkoxy, C1 -C8 dialkylamino, phenoxy, diphenylamino and/or C2 -C8 alkoxycarbonyl, A denotes hydrogen, C1 -C20 alkyl, C3 -C8 cycloalkyl, C4 -C20 alkylcycloalkyl, C4 -C20 cycloalkylalkyl, C2 -C20 alkoxyalkyl, aryl, C7 -C20 alkylaryl, C7 -C20 aralkyl, C1 -C20 alkoxy, hydroxy, C1 -C20 hydroxyalkyl, amino, C1 -C20 alkylamino, C2 -C20 dialkylamino, C3 -C12 alkenyleneamino, C3 -C8 cycloalkylamino, arylamino, aryl-C1 -C12 alkylamino, halogen, mercapto, C2 -C20 alkenylenoxy, C3 -C8 cycloalkoxy and aryloxy R3 denotes CH2 --NR1 R2, R4, R5 denote C1 -C20 alkyl by the reaction of a nitrile of the general formula II in which R1, R2, R4, R5, X and A have the aforementioned meanings and R3 stands for --CH2 --NR1 R2 or cyano, with a secondary amine of the general formula III STR2 and hydrogen at temperatures ranging from 50° to 250° C. and pressures ranging from 5 to 350 bar in the presence of a catalyst, wherein the catalyst used is palladium on an oxidic support.
