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Selective hydrogenation of benzonitrile and its homologues to primary amines over platinum
Krisztina Lévay,Tamás Kárpáti,László Heged}us 한국공업화학회 2021 Journal of Industrial and Engineering Chemistry Vol.101 No.-
Various supported precious metal (Pt, Rh, Ru, Ir) catalysts have been screened in the reduction of benzonitrile(BN), benzyl cyanide (BC) and 3-phenylpropionitrile (PPN) to benzylamine (BA), 2-phenylethylamine (PEA) and 3-phenylpropylamine (PPA), using our method for selective, heterogeneous,palladium-catalysed hydrogenation of nitriles to primary amines developed previously. A readily availableplatinum on carbon catalyst (10% Pt/C) afforded the best results obtaining complete conversion ofnitriles, as well as comparatively high isolated yields (58–70%) and selectivities to primary amines(57–68%) under mild and optimized conditions [6 bar, 30 C, two immiscible solvents (dichloromethane/water or toluene/water), acidic additives (NaH2PO4, (NH4)H2PO4 or H2SO4)]. Contrary to the typicalhigh secondary amine selectivity of platinum, surprisingly, this Pt/C catalyst proved to be much moreeffective and selective in the formation of PEA and PPA than a Pd/C one applied earlier. To clear the divergencesin the primary amine selectivity observed, quantum chemical calculations (DFT) were accomplishedrelated to the adsorption interactions between the imine intermediates and platinum.
수중에서의 불균일 루테늄 촉매에 의한 일차 아미드의 합성
김정원 ( Jung Won Kim ),정상진 ( Sang Jin Jung ),정호영 ( Ho Young Jung ) 한국화상학회 2013 한국화상학회지 Vol.19 No.2
The ruthenium hydroxide catalyst over aluminum oxide support could be easily prepared and applied to syntheses of the primary amides from primary amines or nitriles in water. The various kinds of amines (or nitriles) including non-activated aliphatic, heterocyclic, and aromatic substrates could be efficiently transformed to the desired products in excellent yields in the absence of the need for additives such as acids or bases and the requirement of oxidants. The observed catalysis was truly heterogeneous. The catalyst was retrieved by simple filtration without leaching of metal and the recovered catalyst after the reaction could be reused several times without appreciable loss of high catalytic performance.
Massoudi, Abdolhossain,Amini, Issa,Ramazani, Ali,Nasrabadi, Fatemeh Zeinali,Ahmadi, Yavar Korean Chemical Society 2012 Bulletin of the Korean Chemical Society Vol.33 No.1
The use of Smiles rearrangement in Ugi-type couplings with tropolone allows very straightforward multicomponent formation of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives. The Ugi four-component reaction of isocyanides with tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), primary amines and aldehydes proceeds smoothly and cleanly under mild conditions to afford 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives in fairly good yields.
Abdolhossain Massoudi,Issa Amini,Ali Ramazani,Fatemeh Zeinali Nasrabadi,Yavar Ahmadi 대한화학회 2012 Bulletin of the Korean Chemical Society Vol.33 No.1
The use of Smiles rearrangement in Ugi-type couplings with tropolone allows very straightforward multicomponent formation of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives. The Ugi four-component reaction of isocyanides with tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), primary amines and aldehydes proceeds smoothly and cleanly under mild conditions to afford 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives in fairly good yields.
Biosynthesis of Multiple Short-chain Primary Amines Based on Retrobiosynthetic Approach
Tong Un CHAE,Dong In KIM,Hyun Uk KIM,Woo Dae JANG,Sang Yup LEE 한국생물공학회 2021 한국생물공학회 학술대회 Vol.2021 No.10
Bio-based production of many chemicals is not yet possible due to the unknown biosynthetic pathways. Here, we report a strategy combining retrobiosynthesis and precursor selection step to design biosynthetic pathways for multiple short-chain primary amines (SCPAs). Streptomyces viridifaciens vlmD encoding valine decarboxylase is examined as a proof-of-concept promiscuous enzyme both in vitro and in vivo for generating SCPAs. Escherichia coli expressing the heterologous vlmD produces 10 SCPAs by feeding their direct precursors. Furthermore, metabolically engineered E. coli strains are developed to produce representative SCPAs from glucose, including the one producing 10.67 g L−1 of iso-butylamine by fed-batch culture. This study presents the strategy of systematically designing biosynthetic pathways for the production of a group of related chemicals as demonstrated by multiple SCPAs as examples.
Jung, H.S.,Yun, T.,Cho, Y.,Jeon, H.B. Pergamon Press 2016 Tetrahedron Vol.72 No.40
<P>In this study, we investigated the direct synthesis of primary arylamines from aryl iodides and bromides by Cu-catalyzed amination using ammonium hydroxide (27% NH3 in H2O) as nucleophile. In this article, two protocols are described: (1) a variety of aryl halides were treated with CuI (10 mol %) and DMEDA (15 mol %) in NH4OH/DMSO, or (2) with only Cul (10 mol %) in NH4OH/PEG300. In each case, the desired primary arylamines were obtained in excellent yields. Although DMEDA and PEG have previously been employed as a ligand or solvent, respectively, the substrates were limited or additional ligands were required for successful conversion. Notably, our new protocols do not require additional inorganic bases, whereas previous methods have used a base. As such, these new protocols are one of the most simple, convenient, and efficient methods that have been reported, to date. (C) 2016 Published by Elsevier Ltd.</P>
Identification and Quantification of Phthalates, PAHs, Amines, Phenols, and Metals in Tattoo
임현희,신호상 대한화학회 2015 Bulletin of the Korean Chemical Society Vol.36 No.8
The determination methods of polycyclic aromatic hydrocarbons (PAHs), phthalates, primary amines, phenols, and metals in tattoo dyes have been optimized and validated using gas chromatography-mass spectrometry, liquid chromatography-tandem mass spectrometry, and inductively coupled plasma-mass spectrometry. Twelve PAHs, 3 phthalates, 4 amines, and 15 metals were identified and quantified in 16 different tattoo dyes purchased from shops in the Republic of Korea. Phenols were not detected in any sample. The total PAHs in six inks and benzo(a)pyrene in one tattoo ink exceeded the legal limit set by the Council of Europe, and their maximum detected concentrations were about 10 and 5 times the limits of the compounds, respectively. 3,3′-Dichlorobenzidine and o-anisidine, which should not be present in tattoo inks by Resolution ResAP (2008) of the Council of Europe, were detected in tattoo inks. Also, Cd, Pb, Cu, Ba, Ni, Sb, Zn, and As exceeded the limits. These hazardous compounds should be controlled to the lowest possible concentrations in the raw materials and the production procedure of tattoo ink.
Xiaowei Zhao,Weihong Zhou,Qiong Jia 한국화학공학회 2009 Korean Journal of Chemical Engineering Vol.26 No.6
In the present study, a synergistic extraction mixture, primary amine N1923 (RNH2) and Cyanex925 (B), was loaded on PTFE powder to prepare PTFE Selective Resin and was employed for the adsorption of zinc, cadmium, and copper from chloride medium. The effects of shaking time, resin amounts, concentration of metal ions, and experimental temperature on the distribution coefficients were determined. The stoichiometry of the adsorbed complexes was determined to be MCl2·(1/2)RNH2·B with the Selective Resin. The equilibrium constants and thermodynamic quantities (ΔH, ΔG, and ΔS) were calculated. Furthermore, the Freundlich isotherm proved to be more suitable than the Langmuir isotherm to indicate the effect of concentration of M2+ on the adsorption with PTFE Selective Resin.