scholarly journals Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3307
Author(s):  
Ádám Tajti ◽  
Nóra Tóth ◽  
Bettina Rávai ◽  
István Csontos ◽  
Pál Tamás Szabó ◽  
...  
Keyword(s):  
Reaction Time ◽  
Continuous Flow ◽  
Molar Ratio ◽  
Primary Amines ◽  
Diethyl Phosphite ◽  
The Novel ◽  
Dialkyl Phosphites ◽  
Ft Ir ◽  
High Yields ◽  
Real Time Information

A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor.

scholarly journals Reaktive E=C(p–p)π Systeme, XXXIV Addition von Alkoholen oder primären Aminen an Phosphaalkene F3CP=C(F)OR. Neue Trifluormethylphosphane und -phosphaalkene/Reactive E = C( p – p ) π-Systems, XXXIV Addition of Alcohols or Primary Amines to Phosphaalkenes F3CP= C(F)OR . Novel Trifluoromethylphosphanes and Phosphaalkenes

1993 ◽  
Vol 48 (1) ◽  
pp. 58-67 ◽  
Author(s):  
Joseph Grobe ◽  
Duc Le Van ◽  
Gudrun Lange
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Molar Ratio ◽  
Primary Amines ◽  
The Novel ◽  
Experimental Conditions ◽  
Pull System ◽  
Fragment Ions ◽  
New Compounds ◽  
C Nmr

The course of the reactions o f fluorophosphaalkenes F3CP = C (F)OR [R = Me (1), Et (2)] with methanol or ethanol strongly depends on the experimental conditions. Thus at 70 °C a mixture of the 2-phosphapropionic acid ester F3CP (H )CO2R [R = Me (3), Et (4)] and trifluoromethylphosphane H2PCF3 is formed [molar ratio: 3 or 4 /H2 CF3 ≈1/1]. If the precursors F3CP (H )CO2R [R = Me (3), Et) are used as starting materials, the reaction with ROH under the same conditions affords 3 and 4, respectively, (90 to 95% yield) with only traces of H2PCF 3. In the presence o f iPr2NH these precursors react with R′OH to give the novel trifluoromethylphosphaalkenes F3CP = C (OR )OR [R /R′: Me/Me (6); E t/E t (7); Me/Et (8)]. With Et2NH , 3 undergoes an addition/elimination process yielding the interesting push/pull system Et2N(F)C = P-CO2Me (5). 1 and 2 react with primary amines R′NH2 (R′= tBu, Me) with stereoselective formation of the fairly labile phosphaalkenes F3CP = C(OR)NHR′ [R /R′: Me/tBu (9), Et/tBu(10), Me/Me (11)] with trans-positions for CF3 and NHR′.The new compounds 3 -11 were characterized by spectroscopic investigations (1H , 19F, 31P, 13C NMR ; IR, MS) and determination of M+ or typical fragment ions [M+ -OR ] by high resolution mass spectrometry.

scholarly journals Synthesis of Ca-Doped Three-Dimensionally Ordered Macroporous Catalysts for Transesterification

2018 ◽  
Vol 2018 ◽  
pp. 1-7 ◽  
Author(s):  
Tanat Chokpanyarat ◽  
Vittaya Punsuvon ◽  
Supakit Achiwawanich
Keyword(s):  
Reaction Time ◽  
Catalyst Concentration ◽  
Sol Gel ◽  
Biodiesel Production ◽  
Molar Ratio ◽  
The Novel ◽  
X Ray Diffraction ◽  
X Ray ◽  
Hierarchical Porous ◽  
Ordered Macroporous

The novel three-dimensionally ordered macroporous (3DOM) CaO/SiO2, 3DOM CaO/Al2O3, and 3DOM Ca12Al14O32Cl2 catalysts for biodiesel transesterification were prepared by sol-gel method. The 3DOM catalysts were characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), and Fourier transform infrared spectroscopy (FTIR). The hierarchical porous structure was achieved; however, only 3DOM CaO/Al2O3 and 3DOM Ca12Al14O32Cl2 catalysts were used for transesterification due to high amount of active CaO. Various parameters such as methanol to oil molar ratio, catalyst concentration, reaction time, and their influence on the biodiesel production were studied. The result showed that 99.0% RPO conversion was achieved using the 3DOM Ca12Al14O33Cl2 as a catalyst under the optimal condition of 12 : 1 methanol to oil molar ratio and 6 wt.% catalyst with reaction time of 3 hours at 65°C.

Synthesis and Characterization of Zn-Ca-Mg-Al Hydrotacite-Like Compounds and its Application in the PVC

2011 ◽  
Vol 66-68 ◽  
pp. 65-69
Author(s):  
Long Feng Li ◽  
Yuan Gao ◽  
Mao Lin Zhang
Keyword(s):  
Reaction Time ◽  
Ph Value ◽  
Raw Materials ◽  
Treatment Temperature ◽  
Molar Ratio ◽  
Medium Ph ◽  
X Ray ◽  
Ft Ir ◽  
Thermal Stability Of

Ca-Mg-Al hydrotalcite-like compounds (CaMgAl-HTLcs) were synthesized by a hydrothermal method, and characterized by X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR) and differential thermal analysis (DTA) techniques. The effects of the medium pH value, the molar ratio of the raw materials, the reaction temperature and the reaction time on the structure of CaMgAl-HTLcs were studied. The results showed that increasing treatment temperature and reaction time could improve the crystallinity and monodispersity of hydrotalcite-like compound particles. And well-defined CaMgAl-HTLcs could be prepared at a pH value of 10~11 with n(Zn+Mg+Ca):n(Al) =2. The products synthesized were applied to PVC to improve the thermal stability of PVC.

Optimization and effects of process variables on the production and properties of methyl ester biodiesel

2014 ◽  
Vol 25 (2) ◽  
pp. 39-47 ◽  
Author(s):  
Andrew C. Eloka-Eboka ◽  
Ogbene Gillian Igbum ◽  
Freddie L. Inambao
Keyword(s):  
Reaction Time ◽  
Methyl Ester ◽  
Methyl Esters ◽  
Biodiesel Production ◽  
Molar Ratio ◽  
Individual Response ◽  
Process Variables ◽  
Biodiesel Fuels ◽  
High Yields ◽  
General Response

Optimization of the production process in biodiesel production holds huge prospects. A reduced cost option is the optimization of process variables that affect yields and purity of biodiesel, which was achieved in this study. Optimized production and direct effects of process variables on the production and quality of methyl ester biodiesel fuels from the non-edible seed oils of sandbox seed was carried out. Catalyst nature and concentration, alcohol to triglyceride molar ratio, mixing speed, reaction time and temperature were taken into consideration as variables to their individual response on the yields, viscosity and specific gravity of the methyl esters produced. These are specific indispensable properties of biodiesel for use in compression ignition engines. Optimized concentrations were 0.3 to 1.5% w/v and two mole ratios of 3:1 and 6:1. Time of reaction was varied (5mins to 30mins) with temperatures (38oC and 55oC). Also, the effect of methanol in the range of 4:1and 6:1 (molar ratio) was investigated, keeping catalyst type, reaction time and temperatures constant. The effects of KOH and NaOH on the transesterification were investigated with concentration kept constant at 1%. The general response in this study was that at optimized rate of agitation (800rpm), optimized reaction time was as low as 5minutes, 1% catalyst concentration of NaOH was the optimal concentration, and 55oC was the optimal temperature with attendant high yields. However, there are variations with the nature of feedstock as the work further exposed. These high points are particularly of interest to guide against process backdrop.

scholarly journals Continuous flow synthesis of α-aryl-α-aminophosphonates

2019 ◽  
Vol 91 (1) ◽  
pp. 67-76 ◽  
Author(s):  
Erika Bálint ◽  
Ádám Tajti ◽  
Katalin Ladányi-Pára ◽  
Nóra Tóth ◽  
Béla Mátravölgyi ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Reaction Times ◽  
Primary Amines ◽  
Flow Process ◽  
Flow Synthesis ◽  
Microwave Reactor ◽  
Dialkyl Phosphites ◽  
Benzaldehyde Derivatives

AbstractThe synthesis of α-aryl-α-aminophosphonates was performed by the three-component Kabachnik-Fields reaction of primary amines, benzaldehyde derivatives and dialkyl phosphites in a continuous flow microwave reactor. The target compounds could be obtained in high (~90%) yields without any catalyst in simple alcohols as the solvent. The flow process elaborated required shorter reaction times and lower excess of the reagent, as compared to the “traditional” batch reactions, and allowed the synthesis of the α-aminophosphonates on a somewhat larger scale.

Microwave-assisted alcoholysis of dialkyl phosphites by ethylene glycol and ethanolamine

2014 ◽  
Vol 86 (11) ◽  
pp. 1723-1728 ◽  
Author(s):  
György Keglevich ◽  
Erika Bálint ◽  
Ádám Tajti ◽  
Béla Mátravölgyi ◽  
György Tibor Balogh ◽  
...  
Keyword(s):  
Ethylene Glycol ◽  
Alkyl Substituent ◽  
Molar Ratio ◽  
Diethyl Phosphite ◽  
Microwave Assisted ◽  
Dialkyl Phosphites ◽  
By Products

Abstract A study on the microwave-assisted alcoholysis of diethyl phosphite with ethylene glycol revealed that after optimization of the conditions (molar ratio, temperature and time), the target “monomer,” (HOCH2CH2O)2P(O)H was formed in a proportion of 59 %, but with an incomplete conversion. The formation of the (HOCH2CH2O)(EtO)P(O)H and H(EtO)(O)POCH2CH2OP(O)(OEt)H by-products was, in most cases, inevitable. The alcoholysis with ethanolamine was more efficient and took place in a conversion of 100 % to afford H2NCH2CH2O)2P(O)H in a proportion of 85 %. An alkyl substituent on the N-atom prevented the alcoholysis.

Reaktive E=C(p-p)π-Systeme, XXVIII / Reactive E=C(p-p)π-Systems, XXVIII

1991 ◽  
Vol 46 (8) ◽  
pp. 978-984 ◽  
Author(s):  
Joseph Grobe ◽  
Duc Le Van ◽  
Thomas Großpietsch
Keyword(s):  
Room Temperature ◽  
The Other ◽  
Molar Ratio ◽  
Primary Amines ◽  
Addition Reactions ◽  
The Novel ◽  
One Pot ◽  
Cycloaddition Product ◽  
Tert Butylamine ◽  
The One

The reaction of perfluoro-2-phosphapropene F3CP=CF2 (1) with tert-butylamine or isopropylamine in a 1:3 molar ratio leads to the novel iminomethylene phosphanes F3CP=C=N(tBu) [(2), 30% yield] and F3CP=C=N(iPr) [(3), 5%], respectively. 2 slowly decomposes at room temperature giving tert-butylisonitrile and the cyclophosphanes (F3CP)n (n = 3, 4, 5). 3 is found to be less stable than 2 and for example is attacked by primary amines. The reaction of 2 with 2,3-dimethyl-1,3-butadiene or trimethylphosphane yields, on the one hand, the cycloaddition product of bis(trifluormethyl)diphosphene (4), and on the other hand, the phosphorus ylid Me3P=PCF3 (5) together with (tBu)NC.2 and 3, respectively, are not obtained from (F3C)2PH and the corresponding primary amines in a series of HF elimination and H2NR addition reactions. The main products formed from a 1:4 molar mixture of (F3C)2PH and H2N(iPr) in a one-pot procedure were shown to be the chiral phosphanes F3CP[NH(iPr)]C[=N(iPr)]H (6), F3CP[NH(iPr)]CHF2 (7) and F3CP[NH(iPr)]CH2F (8) (60:35:5). The corresponding reaction of (F3C)2PH with H2N(tBu) mainly yields the compound F3CP[NH(tBu)]CH2F (10).

Catalytic Synthesis of Butyraldehyde Glycol Acetal with H4SiW12O40/MCM-48

2012 ◽  
Vol 531 ◽  
pp. 312-315 ◽  
Author(s):  
Ming Bo Xu ◽  
Jie Yang ◽  
Yong Kui Huang ◽  
Shui Jin Yang
Keyword(s):  
Reaction Time ◽  
Molecular Sieve ◽  
Catalytic Synthesis ◽  
Molar Ratio ◽  
Impregnation Method ◽  
Mass Ratio ◽  
Optimum Conditions ◽  
Environmental Friendly ◽  
Ft Ir ◽  
Catalyst Dosage

A novel environmental friendly catalyst，H4SiW12O40/MCM-48, was prepared by impregnation method. The catalysts were characterized by means of XRD and FT-IR. The synthesis of butyraldehyde glycol acetal catalyzed by H4SiW12O40/MCM-48 was studied with butyraldehyde and glycol as reactants. H4SiW12O40/MCM-48 was an excellent catalyst for the synthesizing butyraldehyde glycol acetal and Keggin structure of H4SiW12O40 kept unchanged after being impregnated on surface of the molecular sieve support. Effects of n(butyraldehyde)∶n(glycol), catalyst dosage, cyclohexane(water-stripped reagent ) and reaction time on yields of the product were investigated. The optimum conditions had been found, that is, molar ratio of butyraldehyde to glycol is1:1.4，mass ratio of catalyst used to the reactants is 0.4% and reaction time is 45 min. Under these conditions, the yield of butyraldehyde glycol acetal can reach 73.3%.

scholarly journals Study of the Three-Component Reactions of 2-Alkynylbenzaldehydes, Aniline, and Dialkyl Phosphites—The Significance of the Catalyst System

Materials ◽  
2021 ◽  
Vol 14 (20) ◽  
pp. 6015
Author(s):  
Nóra Popovics-Tóth ◽  
Kármen Emőke Szabó ◽  
Erika Bálint
Keyword(s):  
Reaction Time ◽  
Chromatographic Separation ◽  
Crucial Role ◽  
Catalyst System ◽  
Short Reaction Time ◽  
Simple Operation ◽  
Dialkyl Phosphites ◽  
Simple Extraction ◽  
High Yields

New, practical approaches for the synthesis of α-amino (2-alkynylphenyl)-methylphosphonates and 1,2-dihydroisoquinolin-1-ylphosphonates were developed. By the propylphosphonic anhydride (T3P®)-mediated Kabachnik–Fields reaction of 2-alkynylbenzaldehydes, aniline, and dialkyl phosphites, α-amino (2-alkynylphenyl)-methylphosphonates were obtained selectively in high yields. The method developed is a simple operation and did not require a chromatographic separation since the products could be isolated from the reaction mixture by a simple extraction. At the same time, 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonates could be prepared effectively from the same kinds of starting materials (2-alkynylbenzaldehydes, aniline, and dialkyl phosphites) at 60 °C in a short reaction time by changing the catalyst for CuCl. Therefore, it was proved that the catalyst system applied played a crucial role with respect to the reaction outcome.

Synthesis of 3-Amino-7-(N,N-Dimethylamino)-2-Substituted-5-Phenylphenazin-5-Ium Chlorides by Oxidative Cyclization

2019 ◽  
Vol 16 (2) ◽  
pp. 283-287
Author(s):  
Yuan Liu ◽  
Ling Jin ◽  
Jun-feng Liu ◽  
Yu-qi Wang ◽  
Zhi-xiang Zhou
Keyword(s):  
Reaction Time ◽  
Potassium Permanganate ◽  
Raw Materials ◽  
13C Nmr Spectroscopy ◽  
Oxidative Cyclization ◽  
Ir Absorption ◽  
Absorption Data ◽  
1H And 13C Nmr ◽  
Ft Ir ◽  
High Yields

Aim and Objective:Phenazines are substances with an extensive range of important applications. Recently, the synthesis of N-arylation has been made more feasible owing to the advent of a new methodology. But because the toxicity of the used oxidant and the low yield, it is necessary to find a nonpoisonous or less toxic oxidant. We report on the use of potassium permanganate as an oxidant to synthesize phenylphenazin-5- ium chlorides via sequential aniline arylation.Materials and Methods:The corresponding 2-substituted-3-amino-5-phenyl-7-N,N-dimethylamino phenazinium chlorides were obtained via various o-substituted toluidines reacted with 4-amino-N,N-dimethyamine and aniline using potassium permanganate as an oxidant under different conditions such as temperature, pH, reaction time and the ratio of raw materials. Infrared (IR) absorption data were acquired on a Thermo Nicolet Nexus 670 FT-IR spectrometer with DTGS KBr detector. All the products were characterized by Mass, 1H and 13C NMR spectroscopy. The total C, H, N, content was measured by the elemental analyzer.Results:The yields of 3-amino-7-(N,N-dimethylamino)-2-substituted-5-phenylphenazin-5-ium chlorides are from 42.5% to 75.8% based on the electrophilic ability of different substituted groups under the temperature of 95°C, pH 4.5 and the reaction time of 8hrs.Conclusion:3-Amino-7-(N,N-dimethylamino)-2-substituted-5-phenylphenazin-5-ium chlorides have been synthesized in high yields via the oxidative cyclization with potassium permanganate. This route is a simple, economic, efficient and environmentally friendly.

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