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107-15-3Relevant articles and documents
Mathew, Suresh,Nair, C. G. R.,Ninan, K. N.
, p. 269 - 294 (1991)
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)
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.
Structural Basis for the Catalytic Mechanism of Ethylenediamine- N, N′-disuccinic Acid Lyase, a Carbon-Nitrogen Bond-Forming Enzyme with a Broad Substrate Scope
Poddar, Harshwardhan,De Villiers, Jandré,Zhang, Jielin,Puthan Veetil, Vinod,Raj, Hans,Thunnissen, Andy-Mark W. H.,Poelarends, Gerrit J.
, p. 3752 - 3763 (2018)
The natural aminocarboxylic acid product ethylenediamine-N,N′-disuccinic acid [(S,S)-EDDS] is able to form a stable complex with metal ions, making it an attractive biodegradable alternative for the synthetic metal chelator ethylenediaminetetraacetic acid (EDTA), which is currently used on a large scale in numerous applications. Previous studies have demonstrated that biodegradation of (S,S)-EDDS may be initiated by an EDDS lyase, converting (S,S)-EDDS via the intermediate N-(2-aminoethyl)aspartic acid (AEAA) into ethylenediamine and two molecules of fumarate. However, current knowledge of this enzyme is limited because of the absence of structural data. Here, we describe the identification and characterization of an EDDS lyase from Chelativorans sp. BNC1, which has a broad substrate scope, accepting various mono- and diamines for addition to fumarate. We report crystal structures of the enzyme in an unliganded state and in complex with formate, succinate, fumarate, AEAA, and (S,S)-EDDS. The structures reveal a tertiary and quaternary fold that is characteristic of the aspartase/fumarase superfamily and support a mechanism that involves general base-catalyzed, sequential two-step deamination of (S,S)-EDDS. This work broadens our understanding of mechanistic diversity within the aspartase/fumarase superfamily and will aid in the optimization of EDDS lyase for asymmetric synthesis of valuable (metal-chelating) aminocarboxylic acids.
Two organically templated niobium and zinconiobium fluorophosphates: Low temperature hydrothermal syntheses of NbOF(PO4)2(C 2H10N2)2 and Zn3(NbOF) (PO4)4(C2H10N2) 2
Liu, Guang-Zhen,Zheng, Shou-Tian,Yang, Guo-Yu
, p. 231 - 237 (2007)
Two new niobium and zinconiobium fluorophosphates, NbOF(PO 4)2(C2H10N2)2 (1) and Zn3(NbOF)(PO4)4-(C2H 10N2)2 (2), have been prepared under hydrothermal conditions using ethylenediamine as a template. The structures were determined by single crystal diffraction to be triclinic, space group P1 (No. 2), a = 8.1075 (6) A, b = 9.8961 (7) A, c = 10.1420(8) A, α = 111.655(1)°, β = 111.51(1)°, γ = 93.206(1)°, V = 686.19(9) A3, and Z = 2 for 1 and orthorhombic, space group Fddd (No. 70), a = 9.1928(2) A, b = 14.2090(10) A, c = 32.2971 (6) A, V = 4218.66(12) A3, and Z = 8 for 2, respectively. Compound 1 is an infinite linear chain consisting of corner-sharing [Nb 2P2] 4-MRs bridged at the Nb centers with organic amines situated between chains, and compound 2, containing the chains similar to that in 1, forms a zeotype framework with organic amines situated in the gismondine-type [4684] cavities. The topology of 2 was previously unknown with vertex symbol 4·4·4·4· 8·8 (vertex 1), 4·4·4·82·8· 8 (vertex 2), 4·4·8·8·82·8 2 (vertex 3), and 4·4·4·8 2·8·8 (vertex 4). The topological relationships between the 4-connected network of 2 and several reported (3,4)-connected networks were discussed.
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Tkaczynski,Kotelko
, (1958)
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Synthesis, characterization and kinetics properties of chromium(III) complex [Cr(3-HNA)(en)2]Cl · H2O · CH3OH
Liu, Bin,Li, Ying-qi,Yang, Bin-Sheng
, p. 367 - 370 (2007)
The reaction of chromium(III) chloride, 3-hydroxy-2-naphthoic acid (3-HNA) and ethylenediamine (en) led to the formation of complex [Cr(3-HNA)(en)2]Cl · H2O · CH3OH, Bis(ethylenediamine-κ2N,N′)(3-hydroxy-2-napht
Durham, D. A.,Hart, F. A.
, p. 145 - 157 (1969)
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Lee,Hahn
, p. 6420,6424 (1969)
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Intramolecular Nucleophilic and General Acid Catalysis in the Hydrolysis of an Amide. Some Comments on the Mechanism of Catalysis by Serine Proteases
Morris, Jeffrey J.,Page, Michael I.
, p. 1131 - 1136 (1980)
The lactonisation of N-(2-aminoethyl)-6-endo-hydroxybicycloheptane-2-endo-carboxamide shows a sigmoid pH-rate profile which is interpreted, kinetically, in terms of the hydroxide-ion-catalysed hydrolysis of the amide with the terminal amino-group unprotonated and protonated.Reaction of the latter species occurs with a rate enhancement of ca. 109 compared with an amide lacking the hydroxy- and protonated amino-groups.This is attributed to intramolecular nucleophilic and general acid-catalysis.The relative effectiveness of these two processes are compared and it is concluded that intramolecular general acid-catalysis makes a relatively minor contribution to the rate enhancement even though the breakdown of the tetrahedral intermediate is thought to be a concerted process.Some comments are made about the mechanisms proposed for the chymotrypsin-catalysed hydrolysis of amides and concerted breakdown of the tetrahedral intermediate is suggested as a possible mechanism.
Ethylenediamine and Aminoacetonitrile Catalyzed Decarboxylation of Oxalacetate
Leussing, Daniel L.,Raghavan, N. V.
, p. 5635 - 5643 (1980)
Monoprotonated ethylenediamine (ENH+) and aminoacetonitrile (AAN) are highly effective catalysts for the decarboxylation of oxalacetate (OA2-) with the latter amine showing 50percent faster rates.The mechanisms of the reactions are the same as that earlier proposed by Guthrie and Jordan from studies on the carboxylation of acetoacetate (AA-): amine and keto acid react to form ketimine which either decarboxylates or is competitively converted to enamine.We find that a prton is required to effect decarboxylation, but it also promotes enamine formation, the more so the greater basicity of the parent amine.Owing to this side reaction, the more basic amines tend to show lower catalytic activity with respect to decarboxylation. a second effect also contributes to the high activity of AAN: even though the rate constants for imine formation appear to be roughly similar with AAN and ENH+, proton catalysis has a much larger net influence on the AAN rate because changes in +> are not canceled by inverse changes in . 4-Ethyloxalacetate forms an adduct with ENH+ that has a considerably greater enamine content and a higher stability than its OA2- analogue.These differences in substrate behavior must be taken into account when esters are used as models for the parent keto acids in these reactions.Comparison of our results with those previously published for OA2- decarboxylation catalyzed by a partially quaternized poly(ethylenimine) suggests that OA2- is predominantly bound to the quaternary amine sites but decarboxylation likely proceeds via a Schiff-base mechanism.
Kinetics and thermodynamics of amine and diamine signaling by a trifluoroacetyl azobenzene reporter group
Mertz, Eric,Beil, James B.,Zimmerman, Steven C.
, p. 3127 - 3130 (2003)
(Matrix presented) (Trifluoroacetyl)azobenzene dyes were previously employed as amine reporter groups (chemosensors) in a dendrimer-based monomolecular imprinting system. Kinetic and binding studies with a range of amines and diamines show that the highly selective signaling observed for alkane diamines by these imprinted dendrimers arises from a kinetic effect due to intramolecular general base-catalyzed carbinolamine formation with the dye itself. The relationship between diamine structure and carbinolamine stability and rate of formation is described.
7-(Imidazolidin-1-ylmethyl)quinolin-8-ol: An unexpected product from a mannich-type reaction in basic medium
Rivera, Augusto,Rios-Motta, Jaime,Navarro, Miguel Angel
, p. 531 - 537 (2006)
7-(Imidazolidin-1-ylmethyl)quinoline-8-ol, an N-substituted imidazolidine, was synthesized in a one-step reaction between 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD) and 8-hydroxyquinoline. Obtaining this substance enhanced the scope of possibilities in the synthesis of unsymmetrically N,N-disubstituted imidazolidines. 1H-NMR spectral studies revealed that this type of substance does not undergo ring-chain tautomerism.
Effect of Re promoter on the structure and catalytic performance of Ni-Re/Al2O3 catalysts for the reductive amination of monoethanolamine
Ma, Lei,Yan, Li,Lu, An-Hui,Ding, Yunjie
, p. 8152 - 8163 (2018)
In this paper, Ni/Al2O3 catalysts (15 wt% Ni) with different Re loadings were prepared to investigate the effect of Re on the structure and catalytic performance of Ni-Re/Al2O3 catalysts for the reductive amination of monoethanolamine. Reaction results reveal that the conversion and ethylenediamine selectivity increase significantly with increasing Re loading up to 2 wt%. Ni-Re/Al2O3 catalysts show excellent stability during the reductive amination reaction. The characterization of XRD, DR UV-Vis spectroscopy, H2-TPR, and acidity-basicity measurements indicates that addition of Re improves the Ni dispersion, proportion of octahedral Ni2+ species, reducibility, and acid strength for Ni-Re/Al2O3 catalysts. The Ni15 and Ni15-Re2 catalysts were chosen for in-depth study. The results from SEM-BSE, TEM, and CO-TPD indicate that smaller Ni0 particle size and higher Ni0 surface area are obtained in the reduced Ni-Re/Al2O3 catalysts. Results from in situ XPS and STEM-EDX line scan suggest that Re species show a mixture of various valances and have a tendency to aggregate on the surface of Ni0 particles. During reaction, the Ni0 particles on the Al2O3 support are stabilized and the sintering process is effectively suppressed by the incorporation of Re. It could be concluded that sufficient Ni0 sites, the collaborative effect of Ni-Re, and brilliant stability contribute to the excellent catalytic performance of Ni-Re/Al2O3 catalysts for the reductive amination of monoethanolamine.
Applications of dynamic combinatorial chemistry for the determination of effective molarity
Ciaccia, Maria,Tosi, Irene,Baldini, Laura,Cacciapaglia, Roberta,Mandolini, Luigi,Di Stefano, Stefano,Hunter, Christopher A.
, p. 144 - 151 (2015)
A new strategy for determining thermodynamic effective molarities (EM) for macrocylisation reactions using dynamic combinatorial chemistry under dilute conditions is presented. At low concentrations, below the critical value, Dynamic Libraries (DLs) of bifunctional building blocks contain only cyclic species, so it is not possible to quantify the equilibria between linear and cyclic species. However, addition of a monofunctional chain stopper can be used to promote the formation of linear oligomers allowing measurement of EM for all cyclic species present in the DL. The effectiveness of this approach was demonstrated for DLs generated from mixtures of 1,3-diimine calix[4]arenes, linear diaminoalkanes and monoaminoalkanes. For macrocycles deriving from one bifunctional calixarene and one diamine, there is an alternating pattern of EM values with the number of methylene units in the diamine: odd numbers give significantly higher EMs than even numbers. For odd numbers of methylene units, the alkyl chain can adopt an extended all anti conformation, whereas for even numbers of methylene units, gauche conformations are required for cyclisation, and the associated strain reduces EM. The value of EM for the five-carbon linker indicates that this macrocycle is a strainless ring. This journal is
PREPARATION METHOD OF ETHYLENEDIAMINE
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Paragraph 0048-0049; 0053-0054; 0058-0061, (2021/06/01)
A dehydrogenation reaction step in which (A) monoethanolamine is dehydrogenated to form aminoacetaldehyde in the presence of a reductive amination catalyst containing cobalt, scandium, and palladium as an active ingredient. A dehydration reaction step of contacting (B) said aminoacetaldehyde with an amine compound to form iminoethanamine. A hydrogenation process wherein (C) is contacted with iminoethaneamine and hydrogen to form ethylenetriamine. Method for manufacturing a semiconductor device A process for the preparation of ethyleneamine.
METHOD FOR PRODUCING ETHANOLAMINES AND/OR ETHYLENEAMINES
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Paragraph 0250-0257, (2020/04/09)
The present invention relates to a process for preparing ethanolamines and/or ethyleneamines in the gas phase by reacting ethylene glycol with ammonia in the presence of an amination catalyst. It is a characteristic feature of the process that the amination catalyst is prepared by reducing a calcined catalyst precursor comprising an active composition, where the active composition comprises one or more active metals selected from the group consisting of the elements of groups 8, 9, 10 and 11 of the Periodic Table of the Elements and optionally one or more added catalyst elements selected group consisting of the metals and semimetals of groups 3 to 7 and 12 to 17, the element P and the rare earth elements. It is a further characteristic feature of the process that a catalyst precursor having low basicity is used, the low basicity being achieved in that a) the catalyst precursor is prepared by coprecipitation and the active composition additionally comprises one or more basic elements selected from the group consisting of the alkali metals and alkaline earth metals; orb) the catalyst precursor, as well as the active composition, additionally comprises a support material and is prepared by impregnating the support material or precipitative application onto the support material and the support material comprises one or more basic elements selected from the group consisting of the alkali metals, Be, Ca, Ba and Sr or one or more minerals selected from the group consisting of hydrotalcite, chrysotile and sepiolite; orc) the catalyst precursor, as well as the active composition, additionally comprises a support material and is prepared by impregnating the support material or precipitative application onto the support material and the active composition of the catalyst support comprises one or more basic elements selected from the group consisting of the alkali metals and the alkaline earth metals; ord) the catalyst precursor is calcined at temperatures of 600° C. or more; ore) the catalyst precursor is prepared by a combination of variants a) and d) or by a combination of variants b) and d) or by a combination of variants c) and d).