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.

Synthesis of Bis-Indolylmethanes Containing 1,2,3-Triazolyl Catalyzed by Brønsted Acidic Ionic Liquid under Solvent-Free Conditions

2011 ◽  
Vol 287-290 ◽  
pp. 1696-1699
Author(s):  
Yong Hong Zhang ◽  
Zhen Kai Lei ◽  
Xiang Ju Huang ◽  
Xiao Yu Pan ◽  
Xin Hai Zhao ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
Solvent Free ◽  
Experimental Procedure ◽  
Short Reaction Time ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Solvent Free Conditions

A series of novelbis-indolylmethanes containing 1,2,3-triazolyl have been synthesized from the reaction of indoles with 4-formyl-1,2,3-triazole catalyzed by Brønsted acidic ionic liquid [PyNCH2CO2H][HSO4] under solvent-free conditions. The satisfactory results were obtained with excellent yields and short reaction time in the experimental procedure.

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.

Study on Bio-Fuels Drop Acid by [BSPy]HSO4 Catalytic Esterification

2013 ◽  
Vol 781-784 ◽  
pp. 2433-2437 ◽  
Author(s):  
Ai Hua Zhang ◽  
Zhi Hong Xiao ◽  
Liang Bo Zhang ◽  
Ru Kuan Liu ◽  
Wu Hong Zhong ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Reaction Time ◽  
Reaction Temperature ◽  
Acid Value ◽  
Esterification Reaction ◽  
Process Conditions ◽  
High Catalytic Activity ◽  
Brønsted Acidic Ionic Liquid ◽  
The Stability ◽  
Acid Esterification

Research on the synthesis of BrOnsted acidic ionic liquid by the method of solvent, the pyrolysis bio-fuel with cornus wisoniana oil drop acid esterification reaction, the catalyst dosage, reaction time and reaction temperature on the effects of the acid dropping and in the best optimization under the condition of the stability of the catalyst were investigated. The experimental results show that [BSPHSO4 with high catalytic activity, optimization of process conditions as follows: 1.2% of catalyst, reaction temperature 75 °C, reaction time of 70 min, acid value reduced to 2.0 mg KOH/g. By optimizing the cycle experiment, the stability of the catalyst performance is good, the catalytic activity is relatively stable.

Brønsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Synthesis of Xanthenes Derivatives as Antimicrobial and Antioxidant Agents

2020 ◽  
Vol 5 (1) ◽  
pp. 11-19
Author(s):  
K.A. Shaikh ◽  
U.N. Chaudhary ◽  
P.J. Doshi
Keyword(s):  
Ionic Liquid ◽  
Antioxidant Activities ◽  
Simple Procedure ◽  
Antimicrobial Activities ◽  
Reusable Catalyst ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Antioxidant Agents ◽  
Solvent Free Conditions ◽  
Xanthene Derivatives

In the present investigation, a mild, efficient and simple procedure has been developed for the synthesis of xanthene derivatives is described via three component condensation of aromatic aldehydes with β- naphthol or dimedone or mixture of β-naphthol and dimedone using Brønsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluene-sulfonate under solvent-free conditions. The synthesized compounds were screened for antimicrobial activities against Gram-positive (Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa) bacteria and fungus (Candida albicans). The antioxidant activities of these compounds were determined by DPPH scavenging free radical method. Present methodology has a number of advantages such as mild reaction condition, inexpensive catalyst, stable at room temperature and it was also found that this catalyst might be recovered quantitatively and reused without much loss of catalytic activity.

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