5515-83-3Relevant academic research and scientific papers
MANUFACTURING METHOD OF N-SUBSTITUTED (METH)ACRYLAMIDE
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Paragraph 0053; 0056, (2019/05/25)
To provide a method for industrially manufacturing high purity β-alkoxypropionic acid amide, β-aminopropionic acid amide and N-substituted (meth)acrylamide at high yield using (meth)acrylic acid ester as a starting material.SOLUTION: By conducting an amidation reaction with amine in the presence of a metal complex as a catalyst using β-substituted propionic acid ester which is a product material of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine, β-substituted propionic acid amide is obtained. Further by conducting a thermal decomposition reaction of the β-substituted propionic acid amide in the presence of the metal complex, and eliminating the alcohol or the amine, objective compound N-substituted (meth)acrylamide is obtained.SELECTED DRAWING: None
Synthesis and catalytic activity of porous polymer containing ionic liquid structures
Li, Junqiao,Lu, Wei,Li, Weifeng,Liang, Xuezheng
, p. 840 - 846 (2016/12/07)
A novel porous polymer containing ionic liquid (IL) structures was synthesized via quternization and condensation of 4-vinylpyridine and p-xylylene dichloride. The ionic liquid structures were incorporated in the polymeric framework and for this reason bulky IL molecules can hardly block pores and neutralize active sites. The polymer shows a high BET surface area and easily accessible active sites. Catalytically the polymer is very active in Michael additions with averaged yields over 96.0% achieved after short reaction times. The high BET surface, remarkable activity, operational simplicity, wide applicability and improved stability are the key properties of the polymer.
Synthesis of a crosslinked polymer with a benzyl(triphenyl)phosphonium ionic liquid moiety and its catalytic activity
Liang, Xuezheng
, p. 99448 - 99453 (2015/12/04)
A novel crosslinked polymer with a benzyl(triphenyl)phosphonium ionic liquid moiety was synthesized from triphenylphosphine and p-xylylene dichloride. The bulky IL molecules were inlaid in the polymeric framework, which avoided pore blocking and IL moiety release. The polymer had a high BET surface area and accessible active sites. The polymer was applied to catalyze the aza-Michael additions and gave average yields over 95.0% in several minutes. The polymer had several advantages such as high BET surface area, high activity and high stability, which hold great potential for green chemical processes.
Design and evaluation of switchable-hydrophilicity solvents
Vanderveen, Jesse R.,Durelle, Jeremy,Jessop, Philip G.
, p. 1187 - 1197 (2014/03/21)
Switchable-hydrophilicity solvents (SHSs) are solvents that can switch reversibly between one form that is miscible with water to another that forms a biphasic mixture with water. For these SHSs, we use CO2 at 1 bar as a stimulus for triggering the transformation to the water-miscible form and removal of CO2 to achieve the reverse. We now report the identification of 13 new SHSs, including the first secondary amine SHSs, and a comparison of all known SHSs in terms of safety and environmental impacts. Amines which include another functional group, especially oxygen-containing groups, are less hazardous than alkylamines. Secondary amines can have improved switching speeds relative to tertiary amines. The variety of SHSs identified suggests that amine SHSs can be designed to have ideal properties for a given application.
Ecofriendly and efficient procedure for hetero-Michael addition reactions with an acidic ionic liquid as catalyst and reaction medium
Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh,Baghbanzadeh, Mostafa
experimental part, p. 109 - 112 (2012/06/30)
1-Methylimidazolium trifluoroacetate ([Hmim]-TFA) is reported as a cost-effective catalyst for a simple and environmentally benign hetero-Michael reaction. [Hmim]TFA works both as reaction medium and catalyst. The reaction is applicable to various aromatic sulfur and nitrogen nucleophiles. This method has advantages such as high yields, short reaction time, and simple workup. The catalyst could be recycled several times without any loss of activity.
Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media
Labade, Vilas B.,Pawar, Shivaji S.,Shingare, Murlidhar S.
experimental part, p. 1055 - 1059 (2012/07/27)
A green approach to the Aza-Michael addition reaction between an amine and α,β-unsaturated compounds has been achieved by conventional as well as non-conventional methods. The reaction is catalyzed by cesium fluoride (CsF) in aqueous media at ambient temperature to afford the product in excellent yield. Ultrasound irradiation has been used as a non-conventional energy source, which reduces the reaction time with improved product yield.
Crown ether complex cation ionic liquids: Preparation and applications in organic reactions
Song, Yingying,Jing, Huanwang,Li, Bo,Bai, Dongsheng
experimental part, p. 8731 - 8738 (2011/09/16)
A series of crown ether complex cation ionic liquids (CECILs) were designed, synthesised and characterised by NMR spectroscopy, HRMS, thermogravimetric differential thermal analysis (TG-DTA) and elemental analysis. Their applications in various organic reactions were investigated: [15-C-5Na][OH], [15-C-5Na][OAc], [18-C-6K][OH] and [18-C-6K][OAc] (15-C-5=[15]crown-5; 18-C-6=[18]crown-6) efficiently catalysed the Michael addition of alkenes and relevant nucleophiles; [18-C-6K][OH] and [15-C-5Na][OH] effectively catalysed the Henry reaction of nitromethane and aromatic aldehydes; [18-C-6K][OH] has excellent catalytic efficiency for Knoevenagel condensation of aromatic aldehydes and malononitrile; PdCl2/[18-C-6K] 3[PO4]/K2CO3 efficaciously catalysed the Heck reaction of olefins and aromatic halides; [18-C-6K][BrO3] can be used as both oxidant and solvent in the oxidation reaction of aromatic alcohols. The CECIL catalysts [15-C-5Na][OH] (Michael addition) and [18-C-6K][OH] (Henry reaction) can be recycled and reused several times without obvious loss of activity and their recovery is very simple.
Highly efficient procedure for the conjugate addition of amines to electron deficient alkenes
Liao, An-Ping,Lan, Ping,Li, Mei,Lan, Li-Hong
experimental part, p. 225 - 228 (2010/09/04)
The novel efficient procedure has been developed for the conjugate addition of amines to electron deficient alkenes. The results showed that the catalyst was very efficient for the reactions with the excellent yields in several minutes. Operational simplicity, without need of any solvent, low cost of the catalyst used, high yields, reusability, excellent chemoselectivity, applicability to large-scale reactions are the key features of this methodology. The article is published in the original.
A comparison between nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in hydroamination of activated olefins
Dash, Chandrakanta,Shaikh, Mobin M.,Butcher, Ray J.,Ghosh, Prasenjit
experimental part, p. 2515 - 2524 (2010/05/14)
A comparison is drawn between the nickel and palladium precatalysts of 1,2,4-triazole based N-heterocyclic carbenes in the hydroamination of activated olefins. Though all of the newly designed nickel and palladium precatalysts, trans-[1-i-propyl-4-R-1,2,4-triazol-5-ylidene]2MBr2 [R = Et, M = Ni (1b); R = Et, M = Pd (1c); R = CH2CHCH2, M = Ni (2b) and R = CH2CHCH2, M = Pd (2c)], are moderately active for hydroamination reaction of a variety of secondary amines viz. morpholine, piperidine, pyrrolidine and diethylamine with activated olefins like, acrylonitrile, methyl acrylate, ethyl acrylate and t-butyl acrylate at room temperature in 1 hour, the nickel complexes (1b and 2b) exhibited superior activity compared to its palladium counterparts (1c and 2c). The better performance of the nickel complexes has been correlated to the more electron deficient metal center in the nickel 1b and 2b complexes than in the palladium 1c and 2c analogs based on the density functional theory studies. The 1b-c and 2b-c complexes were synthesized by the reaction of 1-i-propyl-4-R-1,2,4- triazolium bromide [R = Et (1a) and R = CH2CHCH2 (2a)] with MCl2 [M = Ni, Pd] in presence of NEt3 as a base. The Royal Society of Chemistry 2010.
Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates
Dhake, Kishor P.,Tambade, Pawan J.,Singhal, Rekha S.,Bhanage, Bhalchandra M.
experimental part, p. 4455 - 4458 (2010/09/20)
An efficient protocol for the regioselective aza-Michael addition of amines with acrylates using CaL B as a biocatalyst at 60 °C has been developed. The reaction is applicable to a wide variety of primary and secondary amines with different acrylates to synthesize the corresponding β-amino esters with good yields. An alternative route for the synthesis of higher β-amino esters through the additional transesterification step is also studied and was found effective.
