- Kinetic studies of the N-Alkylation of secondary amines with 1, 2-dichloroethane
-
The reaction of 1,2-dichloroethane with 2-(ethylamino)ethanol or diethylamine have been investigated in several solvents from 51 to 80°C. A reaction mechanism has been proposed where 1, 2-dichloroethane reacts with the secondary amines in both bimolecular substitution (SN 2) and elimination (E2) reactions; the substitution product is rapidly converted in an aziridinium ion and undergoes a consecutive reaction with the starting amine to give a tetrasubstituted ethylenediamine. The rate constants as well as the activation energies of these reactions have been determined.
- Yang,Thyrion
-
-
Read Online
- Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis
-
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.
- Pelckmans, Michiel,Vermandel, Walter,Van Waes, Frederik,Moonen, Kristof,Sels, Bert F.
-
p. 14540 - 14544
(2017/10/23)
-
- N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/γ-Al2O3
-
A simple method for N-alkylation of 1, 2-diaminoethane with different alcohols in a fixed-bed reactor using cheap CuO-NiO/γ-Al2O 3 as the catalyst has been developed. The present catalytic system was applicable in the N-alkylation of 1, 2-diaminoethane with both primary and secondary alcohols. Mono-N-alkylation of 1, 2-diaminoethane with low-carbon alcohols resulted in high yields; the yields of tetra-N-alkylation of 1, 2-diaminoethane with low-carbon alcohols declined markedly with the increase of the molecular volume of alcohols.
- Huang, Jia-Min,Xu, Lu-Feng,Qian, Chao,Chen, Xin-Zhi
-
experimental part
p. 304 - 307
(2012/08/28)
-
- N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/?3-Al2O3
-
A simple method for N-alkylation of 1,2-diaminoethane with different alcohols in a fixed-bed reactor using cheap CuO-NiO/?3-Al2O3 as the catalyst has been developed. The present catalytic system was applicable in the N-alkylation of
- Huang, Jia-Min,Xu, Lu-Feng,Qian, Chao,Chen, Xin-Zhi
-
p. 304 - 307
(2015/03/03)
-
- Reactions of (Et2NCH2CH2NEt 2)·H2SiCl2 with selected diorganometallic reagents of magnesium and lithium
-
Addition of the THF-insoluble di-Grignard reagent from 2,2′-dibromo- 4,4′-tert-butylbiphenyl (1) to a solution of [(teeda)·H 2SiCl2] in CH2Cl2/THF produced 2,7-di-tert-butyl-9H-9-silafluorene (3) in isolated, recrystallized yields of 2O, when reacted with [(teeda)·H2SiCl2] in CH2Cl 2/Et2O, gave similar yields of 5,10-dihydro-2,5,8- trimethylphenazasiline (4). In the absence of CH2Cl2 the major product produced from 1 was the spirocycle 2,2′,7,7′-tetra- tert-butyl-9,9′-spirobi[9H-9-silafluorene] both in a solvent-free form (5′) and as an ethanol solvate (5), both of which were crystallographically characterized. The spirocycle 2,2′,5,5′,8, 8′-hexamethyl-5,10-dihydro-10,10-spirobiphenazasiline (6) was formed from the reaction of the dilithio reagent of 2 in the absence of CH 2Cl2.
- Corey, Joyce Y.,Trankler, Kevin A.,Braddock-Wilking, Janet,Rath, Nigam P.
-
experimental part
p. 5708 - 5713
(2011/02/16)
-
- METHOD FOR PRODUCING N-MONOALKYL-SUBSTITUTED ALKYLENE AMINE
-
PROBLEM TO BE SOLVED: To provide a method for producing an N-monoalkyl-substituted alkylene amine especially useful for uses such as medicine intermediates, agrochemical intermediates, urethane resin-foaming catalysts, surfactants and the like among alkyl-substituted alkylene amine compounds from an alcohol and an alkylene amine as raw materials. SOLUTION: This method for producing the N-monoalkyl-substituted alkylene amine is characterized by reacting the alkylene amine with a ≥2C alkyl alcohol in the presence of a copper-containing oxide catalyst system. The N-monoalkyl-substituted alkylenamine is produced in high conversion and in N-monoalkylation selectivity.
- -
-
Page/Page column 6; 8
(2010/02/11)
-
- Preparation of bidentate ligands
-
A process is disclosed for preparing biaryl, bidentate ligands comprising: (1) contacting a biaryl compound having the structural formula: STR1 with a proton abstracting agent under conditions suitable to form a biaryl dianion, which is then (2) contacted with a Group V compound of the formula: STR2 where X' is halogen or a suitable leaving group.
- -
-
-
- ALKYLATION OF ACYCLIC AND CYCLIC DIAMINES AND POLYAMINES
-
Alkylation of diamines and polyamines by allyl and methallyl chlorides or by chloropropenes has been used to obtain polyalkylpolyamines that had not been described previously.The alkylation of the polyamines by allyl and methallyl chlorides proceeds more energetically in comparison with the alkylation by ethyl chloride or chloropropenes.The alkylation of either cyclic and acyclic polyamines begins with the primary amino group.With increasing length of the chain and the alkyl radical at the nitrogen of the alkylated polyamines, their capability for reacting with the evolved hydrogen chloride drops off, and this leads to a decrease in yield of the desired products owing to the loss of activity of the original or partly alkylated polyamines.
- Zagudullin, R. N.,Baimetov, Z. M.
-
p. 889 - 894
(2007/10/02)
-
- Homogeneously Catalyzed Synthesis of β-Amino Alcohols ans Vicinal Diamines from Ethylene Glycol and 1,2-Propanediol
-
Disubstituted β-amino alcohols and tetrasubstituted vicinal alkanediamines have been synthesized in high yield and at mild temperatures by the selective amination of ethylene glycol and 1,2-propanediol catalyzed by ruthenium or iridium complexes.
- Marsella, John A.
-
p. 467 - 468
(2007/10/02)
-