Introduction of bis-imidazolium dihydrogen phosphate as a new green acidic ionic liquid catalyst in the synthesis of arylidene malononitrile, ethyl (E)-3-(aryl)-2-cyanoacrylate and tetrahydrobenzo[b]pyran derivatives

2021 ◽  
Author(s):  
Zahra Rahmatizadeh-Pashaki ◽  
Nader Daneshvar ◽  
Farhad Shirini
Keyword(s):  
Ionic Liquid ◽  
Dihydrogen Phosphate ◽  
Acidic Ionic Liquid

scholarly journals Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

2020 ◽  
Vol 16 ◽  
pp. 351-361
Author(s):  
Fei You ◽  
Xing He ◽  
Song Gao ◽  
Hong-Ru Li ◽  
Liang-Nian He
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
Ricinoleic Acid ◽  
Viscosity Index ◽  
Acid Value ◽  
Dihydrogen Phosphate ◽  
High Catalytic Activity ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions

Raw material from biomass and green preparation processes are the two key features for the development of green products. As a bio-lubricant in metalworking fluids, estolides of ricinoleic acid are considered as the promising substitute to mineral oil with a favorable viscosity and viscosity index. Thus, an efficient and sustainable synthesis protocol is urgently needed to make the product really green. In this work, an environment-friendly Brønsted acidic ionic liquid (IL) 1-butanesulfonic acid diazabicyclo[5.4.0]undec-7-ene dihydrogen phosphate ([HSO3-BDBU]H2PO4) was developed as the efficient catalyst for the production of oligomeric ricinoleic acid from ricinoleic acid under solvent-free conditions. The reaction parameters containing reaction temperature, vacuum degree, amount of catalyst and reaction time were optimized and it was found that the reaction under the conditions of 190 °C and 50 kPa with 15 wt % of the [HSO3-BDBU]H2PO4 related to ricinoleic acid can afford a qualified product with an acid value of 51 mg KOH/g (which corresponds to the oligomerization degree of 4) after 6 h. Furthermore, the acid value of the product can be adjusted by regulating the reaction time, implying this protocol can serve as a versatile method to prepare the products with different oligomerization degree and different applications. The other merit of this protocol is the facile product separation by stratification and decantation ascribed to the immiscibility of the product and catalyst at room temperature. It is also worth mentioning that the IL catalyst can be used at least for five cycles with high catalytic activity. As a result, the protocol based on the IL catalyst, i.e. [HSO3-BDBU]H2PO4 shows great potential in industrial production of oligomeric ricinoleic acid from ricinoleic acid.

scholarly journals The green synthesis of N-hydroxyethyl-substituted 1,2,3,4-tetrahydroquinolines with acidic ionic liquid as catalyst

2020 ◽  
Vol 9 (1) ◽  
pp. 554-558
Author(s):  
Hui Guo ◽  
Haonan Li ◽  
Xiaoyue Cao ◽  
Zuoyao Wang ◽  
Qian Zhang ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Green Synthesis ◽  
Superior Performance ◽  
Dihydrogen Phosphate ◽  
Unsaturated Ketone ◽  
Acidic Ionic Liquid

AbstractN-Hydroxyethyl-substituted 1,2,3,4-tetrahydroquinolines were synthesized by the reaction of 2-(phenylamino)ethanol with unsaturated ketone catalyzed by acidic ionic liquid N-methyl-2-pyrrolidonium dihydrogen phosphate [NMPH]H2PO4, obviating the need for toxic and expensive catalysts. The acidic ionic liquid not only showed superior performance over H3PO4 but also was stable and could be reused at least five times with a slight loss of activity. It provided a straightforward and efficient protocol for the synthesis of 1,2,3,4-tetrahydroquinoline derivatives.

1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

2020 ◽  
Vol 23 (2) ◽  
pp. 157-167
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Biginelli Reaction ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Dicationic Ionic Liquid

Objective: A facile and efficient method for synthesis of 3, 4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by a novel dicationic Brönsted acidic ionic liquid, [(EtNH2)2SO][HSO4]2, has been successfully developed. Material and Method:: 3, 4-Dihydropyrimidin-2(1H)-ones were synthesized through one-pot condensation of aromatic aldehydes, ethyl acetoacetate, and urea under solvent-free conditions using [(EtNH2)2SO][HSO4]2 as a novel catalyst. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate / n-hexane = 1 / 5). The products have been characterized by IR, 1H NMR, 13C NMR, and also by their melting points. Results: In this research, a library of dihydropyrimidinone derivatives was synthesized via Biginelli reaction under solvent-free conditions at 120oC using [(EtNH2)2SO][HSO4]2 as a catalyst. Various aromatic aldehydes, as well as heteroaromatic aldehydes, were employed, affording good to high yields of the corresponding products and illustrating the substrate generality of the present method. In addition, the prepared dicationic Brönsted acidic ionic liquid can be easily recovered and reused. Conclusion: 1, 1’-Sulfinyldiethylammonium bis (hydrogen sulfate), as a novel dicationic ionic liquid, can act as a highly efficient catalyst for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions.

Synthesis and Characterization of a Novel Ionic Liquid Based on N,N,N,N-tetramethylethylenediamine and its Application in the Synthesis of 1,8-dioxo-octahydro Xanthenes

2018 ◽  
Vol 21 (7) ◽  
pp. 526-532 ◽  
Author(s):  
Zahra Abdi Piralghar ◽  
Mohammad Mahmoodi Hashemi ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Chlorosulfonic Acid ◽  
Solvent Free ◽  
Aryl Aldehydes ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions ◽  
Aryl Aldehyde ◽  
High Yields

Aim and Objective: In this work, we synthesized and characterized a novel Brönsted acidic ionic liquid from the reaction of N, N, N’, N’-tetramethylethylenediamine with chlorosulfonic acid and explored its catalytic activity in 1, 8-dioxo-octahydroxanthenes synthesis. Materials and Methods: Dimedone, aryl aldehydes, and the ionic liquid as the catalyst were reacted under solvent-free conditions. The progressive of the reaction was monitored by a thin layer of chromatography (ethyl acetate/n-hexane = 1/5). All products were characterized as the basis of their spectra data and melting point by comparison with those reported in the literature. Results: The prepared ionic liquid was successfully applied in the synthesis of 1, 8-dioxooctahydroxanthenes in good to high yields on the reaction of aryl aldehyde and dimedone at 120oC under solvent-free conditions. Conclusion: This research demonstrates that the catalyst is impressive for 1, 8-dioxo-octahydroxanthenes synthesis under solvent-free conditions.

Highly Efficient Synthesis of β-Amino Ketones via Direct Mannich-type Reaction Catalyzed by Acidic Ionic Liquid

2011 ◽  
Vol 8 (6) ◽  
pp. 385-390 ◽  
Author(s):  
Dong-Nuan Zhang ◽  
Ji-Tai Li ◽  
Ya-Li Song ◽  
Guo-Feng Chen
Keyword(s):  
Ionic Liquid ◽  
Efficient Synthesis ◽  
Type Reaction ◽  
Acidic Ionic Liquid ◽  
Highly Efficient

scholarly journals Ionic Liquid-Assisted Synthesis of Ag3PO4 Spheres for Boosting Photodegradation Activity under Visible Light

Catalysts ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 788
Author(s):  
Beibei Zhang ◽  
Lu Zhang ◽  
Yulong Zhang ◽  
Chao Liu ◽  
Jiexiang Xia ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Visible Light ◽  
High Efficiency ◽  
Chemical Precipitation ◽  
Active Species ◽  
Precipitation Method ◽  
Dihydrogen Phosphate ◽  
Xrd Pattern ◽  
Simple Chemical ◽  
Visible Light Driven

In this work, a simple chemical precipitation method was employed to prepare spherical-like Ag3PO4 material (IL-Ag3PO4) with exposed {111} facet in the presence of reactive ionic liquid 1-butyl-3-methylimidazole dihydrogen phosphate ([Omim]H2PO4). The crystal structure, microstructure, optical properties, and visible-light photocatalytic performance of as-prepared materials were studied in detail. The addition of ionic liquids played a crucial role in forming spherical-like morphology of IL-Ag3PO4 sample. Compared with traditional Ag3PO4 material, the intensity ratio of {222}/{200} facets in XRD pattern of IL-Ag3PO4 was significantly enhanced, indicating the main {111} facets exposed on the surface of IL-Ag3PO4 sample. The presence of exposed {111} facet was advantageous for facilitating the charge carrier transfer and separation. The light-harvesting capacity of IL-Ag3PO4 was larger than that of Ag3PO4. The photocatalytic activity of samples was evaluated by degrading rhodamine B (RhB) and p-chlorophenol (4-CP) under visible light. The photodegradation efficiencies of IL-Ag3PO4 were 1.94 and 2.45 times higher than that of Ag3PO4 for RhB and 4-CP removal, respectively, attributing to a synergy from the exposed {111} facet and enhanced photoabsorption. Based on active species capturing experiments, holes (h+), and superoxide radical (•O2−) were the main active species for visible-light-driven RhB photodegradation. This study will provide a promising prospect for designing and synthesizing ionic liquid-assisted photocatalysts with a high efficiency.

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