A Brønsted acidic ionic liquid as an efficient and reusable catalyst system for esterification

The dehydration of D‐fructose and glucose has been studied with acidic ionic liquids as catalysts. A series of Brønsted‐acidic ionic liquids has been synthesized and tested in the dehydration of D‐fructose. The results showed that N‐methyl‐2‐pyrrolidonium methyl sulfonate [NMP]+[CH3SO3]− and N‐methyl‐2‐pyrrolidonium hydrogen sulfate [NMP]+[HSO4]− have high catalytic activity. Highly efficient and selective dehydration of D‐fructose to 5‐hydroxymethylfurfural (HMF) was achieved in dimethyl sulfoxide (DMSO) under mild conditions. For example, a 72.3 % yield of HMF with 87.2 % selectivity were obtained for 2 h at 90 °C in the presence of 7.5 mol % [NMP]+[CH3SO3]−. The effects of the reaction temperature, time, and solvent were investigated in detail. The catalyst and solvent can be recycled for the dehydration of D‐fructose. The Hammett method was used to determine the acidities of these ionic liquids, which indicated that the acidity and molecular structure have strong effects on the catalytic activity of ionic liquids. Based on the experimental results, a possible reaction mechanism for the dehydration of D‐fructose is proposed.

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“…[29][30][31] The detailed synthesis conditions are described in the experimental section. [ À is a white solid at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

2010

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“…Esterification of alcohols by carboxylic acids has been carried out in a halogen-free Bronsted acidic ionic liquid, Nmethyl-2-pyrrolidinium methyl sulphonate under mild conditions, and without additional solvent [90] (see Scheme 4). In a very recent report of TSIL, Das and coworkers have reported a sulfonic acid functionalized IL for efficient synthesis of indole derivatives [91].…”

Section: As Acid Catalystsmentioning

confidence: 99%

Ionic Liquids: Synthesis and Applications in Catalysis

Rajni

2014

Advances in Chemistry

217

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Ionic liquids have emerged as an environmentally friendly alternative to the volatile organic solvents. Being designer solvents, they can be modulated to suit the reaction conditions, therefore earning the name "task specific ionic liquids. " Though primarily used as solvents, they are now finding applications in various fields like catalysis, electrochemistry, spectroscopy, and material science to mention a few. The present review is aimed at exploring the applications of ionic liquids in catalysis as acid, base, and organocatalysts and as soluble supports for catalysts.

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“…For this work dichloromethane (DCM) was the solvent of choice. Other studies have employed benzene [9,14], as well as DCM as the solvent [10]. Obviously in the case of [H-NMP][OCym] this compromises the bio-based label that may be attributed to the final product.…”

Section: Resultsmentioning

confidence: 99%

“…The first benefit of these ionic liquids is the joint catalysis and solvation offered onto the reactants. This has been realised with high loadings of acidic ionic liquids (typically 25 mol%) applied at room temperature in otherwise solvent-free systems [9]. Whether these quantities adhere to the definition of solvent or not is debatable.…”

Section: Introductionmentioning

confidence: 99%

Using metrics and sustainability considerations to evaluate the use of bio-based and non-renewable Brønsted acidic ionic liquids to catalyse Fischer esterification reactions

Clark

Farmer

Macquarrie

et al. 2013

sustain chem process

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Background: Ionic liquids have found uses in many applications, one of which is the joint solvation and catalysis of chemical transformations. Suitable Brønsted acidic ionic liquids can be formed by combining lactams with sulphonic acids. This work weighs up the relative benefits and disadvantages of applying these Brønsted acidic ionic liquid catalysts in esterifications through a series of comparisons using green chemistry metrics. Results: A new bio-based ionic liquid was synthesised from N-methyl pyrrolidinone and p-cymenesulphonic acid, and tested as a catalyst in three Fischer esterifications under different conditions. An evaluation of the performance of this Brønsted acidic ionic liquid was made through the comparison to other ionic liquid catalysts as well as conventional homogeneous Brønsted acids.

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A Brønsted acidic ionic liquid as an efficient and reusable catalyst system for esterification

Cited by 104 publications

References 20 publications

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

Efficient and Selective Dehydration of Fructose to 5‐Hydroxymethylfurfural Catalyzed by Brønsted‐Acidic Ionic Liquids

Ionic Liquids: Synthesis and Applications in Catalysis

Using metrics and sustainability considerations to evaluate the use of bio-based and non-renewable Brønsted acidic ionic liquids to catalyse Fischer esterification reactions

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