53280-20-9Relevant academic research and scientific papers
Heterogeneous Aza-Michael Addition Reaction by the Copper-Based Metal–Organic Framework (CuBTC)
Bhattacharjee, Samiran,Shaikh, Aftab Ali,Ahn, Wha-Seung
, p. 2011 - 2018 (2020/11/18)
Abstract: The copper benzene-1, 3, 5-tricarboxylate metal–organic framework (CuBTC) was found to be an effective heterogeneous catalyst for the aza-Michael addition reaction of the four types of amines to electron deficient alkenes at room temperature. The catalytic protocol showed high product yields and outstanding chemo selectivity. The cyclic amines (piperidine and pyrrolidine) and aliphatic amines (n-dibutylamine) provided aza-Michael addition with a high yield of product (?98%) within shorter reaction period (2?h) at room temperature under mild reaction conditions using CuBTC. However, it was observed that the aza-Michael reaction proceeded more slowly, giving 62% yield of product after 24?h in the case of aromatic amine (aniline) with n-butyl acrylate in the presence of CuBTC under identical reaction conditions. The catalyst could be reused four recycles without losing its initial catalytic activity and selectivity. XRD and SEM analysis further confirmed that the crystallinity of catalyst was retained during the reaction. A reaction mechanism is proposed for the aza-Michael addition reaction over heterogeneous CuBTC catalyst. Graphic Abstract: [Figure not available: see fulltext.].
Bio-heterogeneous Cu(0)NC@PHA for n-aryl/alkylation at room temperature
Jian Fui, Choong,Lutfor Rahman, Md,Musta, Baba,Sani Sarjadi, Mohd,Sarkar, Shaheen M.,Xin Ting, Tang
, (2021/06/28)
A pure cellulose was derived from waste fibre and it was chemically modified to a hydroxamic acid ligand. The poly(hydroxamic acid) was treated with an aqueous copper solution to afford the greenish stable five-membered copper complex; namely Cu(II)@PHA. Further, the Cu(II)@PHA was treated with a reducing agent hydrazine hydride to give brown colour cellulose supported copper nanocomplex (Cu(0)NC@PHA). The Cu(0)NC@PHA was characterised by ATR-FTIR, FE-SEM & EDS, TEM, ICP-OES, TGA, XRD and XPS analyses. The cellulose-based Cu(0)NC@PHA was used for the n-aryl/alkylation (Michael addition) reaction with a variety of α,β-unsaturated Michael acceptors to produce the corresponding n-aryl/alkyl products with an excellent yield at room temperature. The Cu(0)NC@PHA showed extraordinary stability and it was easily filtered out from the reaction mixture and may potentially recycled up to five times without loss of its original catalytic ability.
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
Tapioca cellulose based copper nanoparticles for chemoselective N-alkylation
Islam, Md. Shaharul,Mandal, Bablu Hira,Biswas, Tapan Kumar,Rahman, Md. Lutfor,Rashid,Tan, Suat-Hian,Sarkar, Shaheen M.
, p. 550 - 557 (2017/01/05)
Biomaterials as a support for catalysts are of prime importance. Tapioca root which is an abundant biopolymer source was used to synthesize cellulose supported bio-heterogeneous poly(hydroxamic acid) copper nanoparticles (CuN@PHA) and was characterized by Fourier transform infrared spectroscopy (FTIR), ultraviolet-visible spectroscopy (UV-Vis), field emission scanning electron microscopy (FESEM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma atomic emission spectroscopy (ICP-AES), transmission electron microscopy (TEM) analyses. The tapioca cellulose supported CuN@PHA (50 mol ppm) effectively catalyzed N-alkylation reaction of aliphatic amines with α,β-unsaturated compounds to give the corresponding alkylated products. High yields up to 95% were achieved for the converted products. The reusability of the cellulose supported nanoparticles was found to be excellent with no significant reduction of its catalytic activity over several cycles. The catalyst showed high catalytic activity having turnover number (TON) 18000 and turnover frequency (TOF) 2250 h-1.
Waste corn-cob cellulose supported bio-heterogeneous copper nanoparticles for aza-Michael reactions
Sarkar, Shaheen M.,Sultana,Biswas, Tapan Kumar,Rahman, Md. Lutfor,Yusoff, Mashitah Mohd
, p. 497 - 502 (2016/01/12)
Bio-heterogeneous poly(amidoxime) copper nanoparticles were prepared on the modified surface of waste corn-cob cellulose through a graft copolymerization process. The Cu-nanoparticles (0.05 mol% to 50 mol ppm) selectively promoted the aza-Michael reaction of aliphatic amines to give the corresponding alkylated products at room temperature in methanol. The supported nanoparticles were easy to recover and reused eight times without a significant loss of their activity.
Poly(hydroxamic acid) functionalized copper catalyzed C-N bond formation reactions
Islam, Md. Shaharul,Mandal, Bablu Hira,Biswas, Tapan Kumar,Rahman, Md. Lutfor,Rashid,Tan, Suat-Hian,Sarkar, Shaheen M.
, p. 56450 - 56457 (2016/07/06)
Highly active poly(hydroxamic acid) functionalized copper catalysts were synthesized by the surface modification of khaya cellulose through graft copolymerization and subsequent hydroximation processes. The prepared catalysts were well characterized by FTIR, FESEM, HRTEM, ICP-AES, UV-vis and XPS analyses. The supported catalysts effectively promoted C-N bond formation reactions and provided excellent yields of the corresponding products under mild reaction conditions. The catalysts were easy to recover from the reaction mixture and were reused several times without any significant loss of their catalytic activity.
(Meth) acrylamide hydroxyakyl production (by machine translation)
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Paragraph 0019, (2016/12/12)
PROBLEM TO BE SOLVED: To provide a method of manufacturing hydroxyalkyl (meth) acrylamide which uses dibutyl amine as a double bond protecting reagent, and thereby can stably carry out thermal decomposition of an amide adduct without an acid catalyst. SOLUTION: In the method, methyl (meth)acrylate and dialkylamine are reacted to convert into an ester adduct, the adduct is made to react with alkanolamine under the presence of a strong base nature catalyst, an amide adduct which is a synthetic intermediate is obtained after the sulfuric acid neutralizing of the ester adduct, and then thermal decomposition of the amide adduct is carried out to manufacture hydroxyalkyl (meta) acrylamide. Dibutyl amine is used for double bond protecting of methyl (meth)acrylate, and thereby thermal decomposition of the amide adduct obtained thereafter can be carried out stably without using an acid catalyst to obtain hydroxyalkyl (meth) acrylamide. COPYRIGHT: (C)2012,JPO&INPIT
Carboxylate-assisted formation of alkylcarbonate species from co 2 and tetramethylammonium salts with a β-amino acid anion
Hong, Sung Yun,Cheon, Youngeun,Shin, Seung Hoon,Lee, Hyunjoo,Cheong, Minserk,Kim, Hoon Sik
, p. 890 - 897 (2013/07/27)
Tetramethylammonium-based molten salts bearing a β-amino acid anion (TMAAs) are synthesized through Michael addition reactions of amines with methyl acrylate followed by hydrolysis and subsequent neutralization by using aqueous tetramethylammonium hydroxide. The CO2 capture performances of the TMAAs are evaluated and are shown to interact with CO2 in a 1:1 mode in both water and alcohol. FTIR and 13C NMR spectroscopic studies on the interactions of TMAAs with CO2 indicate that the type of CO 2 adduct varies with the solvent used. When water is used as the solvent, a bicarbonate species is produced, whereas hydroxyethylcarbonate and methylcarbonate species are generated in ethylene glycol and methanol, respectively. Computational calculations show that the carboxylate groups of TMAAs contribute towards the formation and stabilization of 1:1 CO2 adducts through hydrogen bonding interactions with the hydrogen atoms of the amino groups.
An efficient biomaterial supported bifunctional organocatalyst (ES-SO 3- C5H5NH+) for the synthesis of β-amino carbonyls
Verma, Sanny,Jain, Suman L.,Sain, Bir
experimental part, p. 2314 - 2318 (2011/05/02)
A biomaterial supported organocatalyst, readily synthesized by the reaction of chemically modified sulfonic group containing expanded corn starch with pyridine exhibited excellent catalytic activity for the synthesis of β-amino carbonyls in excellent yields via aza-Michael addition of amines to electron deficient alkenes. A remarkable enhancement in the reaction rates was observed with the prepared bifunctional organocatalyst in comparison to the either starch grafted sulfonic acid or the corresponding homogeneous pyridinium p-toluenesulfonate.
Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes
Verma, Sanny,Mungse, Harshal P.,Kumar, Neeraj,Choudhary, Shivani,Jain, Suman L.,Sain, Bir,Khatri, Om P.
supporting information; experimental part, p. 12673 - 12675 (2012/01/05)
Graphene oxide was found to be a highly efficient, reusable and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes to furnish corresponding β-amino compounds in excellent yields. The Royal Society of Chemistry 2011.
