ChemInform Abstract: Epoxidation and Baeyer—Villiger Oxidation Using Hydrogen Peroxide and a Lipase Dissolved in Ionic Liquids.

Kotlewska, Aleksandra J.; Rantwijk, Fred van; Sheldon, Roger A.; Arends, Isabel W. C. E.

doi:10.1002/chin.201149038

Cited by 7 publications

(12 citation statements)

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“…In the presence of an olefin substrate, this forms the basis for a chemoenzymatic epoxidation (Figure 6a). More recently, it was shown 140 that better results could be obtained using CaLB dissolved in ILs consisting of HBD cations in combination with nitrate as the coordinating anion. Nitrate is an attractive anion: It is stable under oxidative conditions, nontoxic, biocompatible, and inexpensive.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Role of Biocatalysis in Sustainable Chemistry

2017

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Based on the principles and metrics of green chemistry and sustainable development, biocatalysis is both a green and sustainable technology. This is largely a result of the spectacular advances in molecular biology and biotechnology achieved in the past two decades. Protein engineering has enabled the optimization of existing enzymes and the invention of entirely new biocatalytic reactions that were previously unknown in Nature. It is now eminently feasible to develop enzymatic transformations to fit predefined parameters, resulting in processes that are truly sustainable by design. This approach has successfully been applied, for example, in the industrial synthesis of active pharmaceutical ingredients. In addition to the use of protein engineering, other aspects of biocatalysis engineering, such as substrate, medium, and reactor engineering, can be utilized to improve the efficiency and cost-effectiveness and, hence, the sustainability of biocatalytic reactions. Furthermore, immobilization of an enzyme can improve its stability and enable its reuse multiple times, resulting in better performance and commercial viability. Consequently, biocatalysis is being widely applied in the production of pharmaceuticals and some commodity chemicals. Moreover, its broader application will be further stimulated in the future by the emerging biobased economy.

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Section: Chemical Reviewsmentioning

confidence: 99%

“…172 The E factor of the epoxidation of styrene in ChCl/sorbitol was calculated to be 7.7 compared with 16.7 for the same olefin in [bmim][BF 4 ] (as discussed in the preceding section). 140 We note, however, that comparison with one of the nitrate ILs would probably have been more meaningful.…”

Section: Deep Eutectic Solvents (Dess)mentioning

confidence: 99%

Role of Biocatalysis in Sustainable Chemistry

2017

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“…In addition, 0.025 g of Novozyme-435 per 0.5 mmol of ketone was used in a previous study. 11 We also used a standard molar excess of acids to ketone (i.e., 2:1). As 50 a result of our study, a lower interval of reactive carboxylic acids (i.e., from pentanoic to nonanoic acids) was observed for native CALB ( Table 1).…”

Section: Scheme 1 Chemo-enzymatic Baeyer-villiger Oxidation Of 2methymentioning

confidence: 99%

“…[4][5][6] In the second option, the enzyme in used only in one step of the 25 reaction, and therefore, the reaction is called chemo-enzymatic. [7][8][9][10][11][12][13][14][15] This reaction involves the oxidation of long-or medium-chain carboxylic acids with hydrogen peroxide in the presence of lipase to generate in situ peracid, which is used to oxidise ketones to lactones in the second step. An interesting modification of the 30 chemo-enzymatic method that utilises ethyl acetate as a solvent and a peracetic acid precursor has been recently proposed.…”

Section: Introductionmentioning

confidence: 99%

“…13 Only one report demonstrated that the oxidation of ketones by peracid generated in situ in the reaction system catalysed by Novozyme-435 could be significantly accelerated due to the presence of a few hydrogen bond donating ionic liquids. 11 In 50 addition, Novozyme-435 was dissolved in 1-(3-hydroxypropyl)-3methylimidazolium nitrate or 1-butyl-3-methylimidazolium nitrate forming gel-like homogeneous liquids. When this method was used, ketones were oxidised with 50% H2O2 at 50 °C in 5 h to lactones with moderate to excellent yields.…”

Section: Introductionmentioning

confidence: 99%

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Chemo-enzymatic Baeyer–Villiger oxidation in the presence of Candida antarctica lipase B and ionic liquids

et al. 2015

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A new method for the chemo-enzymatic Baeyer-Villiger oxidation of cyclic ketones to lactones has been developed. The influence of reaction parameters and the structure of various ionic liquid was studied. Free Candida Antarctica lipase B or Novozyme-435 suspended in an ionic liquid were used as the catalytic phase. The reaction was carried out under mild conditions at room temperature using 30% aq. H2O2 as the oxidation agent. 1-Butyl-3-methyl bistriflimide was the most effective ionic liquid and 10 increased the reaction rate compared to toluene. Lipase exhibited good stability, and the ionic liquid could be easily reused. Therefore, a general chemo-enzymatic method for the oxidation of cyclohexanones and cyclobutanones to obtain adequate lactones in high yields (79-95%) has been proposed. 65 enzymes in ionic liquids including polarity, hydrophobicity, nucleophilicity, hydrogen bonding ability, viscosity, enzyme dissolution, and surfactant effect. [18][19][20] In addition, the parameters that quantify the interactions of the proteins and the aqueous electrolytes, such as cosmotropicity vs. chaotropicity, have been 70 proposed for explaining protein behaviour in aqueous ionic liquids. Unfortunately, the anions of ionic liquids do not always strictly follow the Hofmeister series for protein stability. 16 Ionic liquids can also form so-called organised 'nano-structures,' which are described as hydrogen bonded polymeric supramolecules that have 75 polar and non-polar regions. The structure of the ionic liquids can protect the crucial water in the protein from solvophobic

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Ionic Liquids in Selective Oxidation: Catalysts and Solvents

et al. 2017

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Selective oxidation has an important role in environmental and green chemistry (e.g., oxidative desulfurization of fuels and oxidative removal of mercury) as well as chemicals and intermediates chemistry to obtain high-value-added special products (e.g., organic sulfoxides and sulfones, aldehydes, ketones, carboxylic acids, epoxides, esters, and lactones). Due to their unique physical properties such as the nonvolatility, thermal stability, nonexplosion, high polarity, and temperature-dependent miscibility with water, ionic liquids (ILs) have attracted considerable attention as reaction solvents and media for selective oxidations and are considered as green alternatives to volatile organic solvents. Moreover, for easy separation and recyclable utilization, IL catalysts have attracted unprecedented attention as "biphasic catalyst" or "immobilized catalyst" by immobilizing metal- or nonmetal-containing ILs onto mineral or polymer supports to combine the unique properties of ILs (chemical and thermal stability, capacity for extraction of polar substrates and reaction products) with the extended surface of the supports. This review highlights the most recent outcomes on ILs in several important typical oxidation reactions. The contents are arranged in the series of oxidation of sulfides, oxidation of alcohols, epoxidation of alkenes, Baeyer-Villiger oxidation reaction, oxidation of alkanes, and oxidation of other compounds step by step involving ILs as solvents, catalysts, reagents, or their combinations.

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ChemInform Abstract: Epoxidation and Baeyer—Villiger Oxidation Using Hydrogen Peroxide and a Lipase Dissolved in Ionic Liquids.

Cited by 7 publications

References 1 publication

Role of Biocatalysis in Sustainable Chemistry

Role of Biocatalysis in Sustainable Chemistry

Chemo-enzymatic Baeyer–Villiger oxidation in the presence of Candida antarctica lipase B and ionic liquids

Ionic Liquids in Selective Oxidation: Catalysts and Solvents

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