Design and Exploration of –SO3H Group Functionalized Brønsted Acidic Ionic Liquids (BAILs) as Task-Specific Catalytic Systems for Organic Reactions: A Review of Literature

Sarma, Parismita; Dutta, Arup; Borah, Ruli

doi:10.1007/s10563-017-9227-0

Cited by 22 publications

(13 citation statements)

References 76 publications

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“…However, in the procedure we have developed in this study, the purification of the product is extremely easy and practical. [55] However, as can be seen from this reference study, these ionic liquid based catalysts are generally subjected to [27] 2 Esterification NaOCH 3 Solventless B 1 70 90 [28] 3 Via acyl chloride -Benzene-ether C 5 rx 83 [29] 4 Via acyl chloride -Benzene E 16 0-rt 85 [30] www.advancedsciencenews.com www.ejlst.com anion-exchange reactions and some short-chain wax esters were obtained in lower yields (82%) after 48 h. As well known, strong inorganic acids (e.g., HClO 4 or H 2 SO 4 ) used in some studies may cause double bond shifts and isomerization, especially in unsaturated fatty acid derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…Use of expensive catalysts that can be prepared by troublesome methods, higher reaction temperatures and sometimes low yields of products are some of these drawbacks. On the other hand, a comprehensive review study was conducted on organic reactions including also some esterification reactions using −SO 3 H group functionalized Brønsted acidic ionic liquids . However, as can be seen from this reference study, these ionic liquid based catalysts are generally subjected to anion‐exchange reactions and some short‐chain wax esters were obtained in lower yields (82%) after 48 h.…”

Section: Resultsmentioning

confidence: 99%

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Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

Yıldırım

Mudaber

Öztürk

2018

Euro J Lipid Sci & Tech

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Biological wax esters are important commercial products used in various industrial and medicinal fields. These valuable compounds can be synthesized via several chemical and enzymatic reactions which have some advantages and more disadvantages. In particular, many strong acid catalysts cause undesirable structural changes in unsaturated fatty acids molecules. In the present study, easily accessible 1‐hexadecyl‐3‐sulfoimidazolium chloride as an ionic liquid is screened as a mild Brønsted acid metal free catalyst for the chemical esterification, or transesterification, of equimolar amounts of long chain fatty acids or fatty acid methyl esters, respectively, with fatty alcohols in a solventless medium. The various parameters affecting the yield of the wax ester are optimized, catalyst reuse studies, and large scale synthesis are also carried out. According to this alternative practical and green process, a series of wax esters (17 examples) are produced readily in good to excellent yields. There is no undesirable geometric cis‐trans isomerization in unsaturated fatty acids under the reaction conditions used. The catalyst is also quite effective when triglycerides are converted directly to the wax esters via transesterification reaction. Practical Applications: With an effortless and environmentally friendly method developed in this study, various wax esters can be synthesized as valuable industrial materials. In order to synthesis these esters, there is not any restriction for starting compounds. The most important aspect of the developed procedures is that metallic or strong aggressive acidic catalysts are not used compared to existing procedures. It is possible to carry out large‐scale syntheses of esters with high yields. In the present study, a series of industrial and medical important wax esters are synthesized from renewable sources in a solvent‐free environment using IL‐catalyzed environmentally friendly methods.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

Yıldırım

Mudaber

Öztürk

2018

Euro J Lipid Sci & Tech

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“…The literature search also displayed few reports involving N‐alkane sulfonic acid functionalized Brönsted acidic imidazolium/ammonium based ionic liquids as dual solvent‐catalyst system for the Claisen‐Schmidt condensation at 100–160 °C for varied reaction time (1.5 h to 9 h) under inert atmosphere . In these reactions, N‐alkyl sulfonic acid functionalized ionic liquids (ILs) worked as non‐corrosive and recyclable safer alternative of conventional non‐reusable corrosive acidic/basic reagents/catalysts . Thus, in this work, we were interested to explore the catalytic activities of two series of direct ‐N‐SO 3 H functionalized imidazolium ILs i. e. 2‐methyl/2‐ethyl‐1,3‐disulfoimidazolium carboxylate ionic liquids [MDSIM][X] and [EDSIM][X], (where, X − =CF 3 COO − ,CCl 3 COO − and CH 3 COO − ) (Scheme ) for one ‐pot preparation of 3‐substitited indoles after selective formation of the chalcones involving Claisen‐Schmidt condensation and consecutive Michael‐like addition of indole (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

“…[20,22] In these reactions, N-alkyl sulfonic acid functionalized ionic liquids (ILs) worked as non-corrosive and recyclable safer alternative of conventional non-reusable corrosive acidic/basic reagents/ catalysts. [33] Thus, in this work, we were interested to explore the catalytic activities of two series of direct -N-SO 3 H functionalized imidazolium ILs i. e. 2-methyl/2-ethyl-1,3-disulfoimidazolium carboxylate ionic liquids [MDSIM][X] and [EDSIM][X], (where, X À = CF 3 COO À ,CCl 3 COO À and CH 3 COO À ) (Scheme 1) for one -pot preparation of 3-substitited indoles after selective formation of the chalcones involving Claisen-Schmidt condensation and consecutive Michael-like addition of indole (Scheme 2). The products of this one-pot method are abundant in nature as flower scents, perfumes as well as in coal tar and possess antifungal, antimicrobial, antiviral, anti-inflammatory and analgesic activities.…”

Section: Introductionmentioning

confidence: 99%

Brönsted Acidic Ionic Liquids Catalysed Sequential Michael‐Like Addition of Indole with Chalcones via Claisen‐Schmidt Condensation

et al. 2020

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A sequential acidic ionic liquid catalyzed one pot approach was conducted for preparation of 3‐substituted indoles starting from in situ generated chalcones involving Claisen‐Schmidt condensation of substituted aromatic aldehydes with acetophenone followed by Michael‐like addition of indoles to these chalcones under solvent‐free thermal reactions. For this purpose, some new and some reported Brönsted acidic ionic liquids, 2‐alkyl‐1, 3‐disulfoimidazolium carboxylate [RDSIM][X] (where R=Me & Et and X=CH3COO−, CCl3COO−, CF3COO−), were analyzed to compare their Brönsted acidic strength and thermal stabilities. From this investigation, 2‐methyl‐1, 3‐disulfoimidazolium trifluoroacetate [MDSIM][CF3COO] and 2‐ethyl‐1,3‐disulfoimidazolium trifluoroacetate [EDSIM][CF3COO] were determined as efficient ionic liquid catalysts for study of the two‐step one pot synthesis of 3‐substituted indoles.

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“…[8,9] For these reasons, ionic liquids (ILs) are being investigated for their unique chemical and physical properties such as low vapor pressure, non-flammability, mild reaction conditions, thermal stability and recyclability. [10][11][12][13] The key characteristic of an IL is its designability, which can be improved and optimized by properly adjusting the types of anions and cations and their substituents. These properties lead to a wide range of applications, including materials, [14,15] organic synthesis, [16] membrane separating processes, [17] electrochemistry [18] and catalysis.…”

Section: Introductionmentioning

confidence: 99%

The study of industrializable ionic liquid catalysts for long‐chain alkenes Friedel–Crafts alkylation

Zhou

Sheng

et al. 2020

Applied Organom Chemis

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Catalysts based on different halo‐alkanes structures with durable catalytic performance were synthesized and applied to the Friedel–Crafts alkylation of long‐chain alkenes (mixed C16–24 olefins) with toluene. Surprisingly, compared with the usual industrial catalysts (~10 runs), the cyclic times of the ionic liquid (IL) catalysts reached up to 24 runs, which greatly promotes the industrialization process. Then, Lewis acids of catalysts with different precursor/AlCl3 molar ratios were investigated and a close relation was discovered between the Lewis acid and catalytic activity. In addition, a comparison of the different halo‐alkanes structures about those catalysts was made. The results showed that the [C6Et3N]Cl–AlCl3 had the strongest Lewis acid, corresponding to the highest catalytic performance. Also, the structures of precursors and the specific gravity and active site species of catalysts were investigated by Fourier transform infrared and Magic Angle Spinning Nuclear Magnetic Resonance (MAS NMR). Meanwhile, the various parameters (catalyst dosage, toluene/olefin molar ratio, reaction temperature and reaction time) of long‐chain alkenes alkylation with toluene were studied. Finally, under the optimized reaction conditions, the conversion and selectivity of long‐chain alkenes alkylation reached 99.92 and 32.99%, respectively.

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Design and Exploration of –SO3H Group Functionalized Brønsted Acidic Ionic Liquids (BAILs) as Task-Specific Catalytic Systems for Organic Reactions: A Review of Literature

Cited by 22 publications

References 76 publications

Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

Improved Sustainable Ionic Liquid Catalyzed Production of Symmetrical and Non‐Symmetrical Biological Wax Monoesters

Brönsted Acidic Ionic Liquids Catalysed Sequential Michael‐Like Addition of Indole with Chalcones via Claisen‐Schmidt Condensation

The study of industrializable ionic liquid catalysts for long‐chain alkenes Friedel–Crafts alkylation

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