A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen-Mn(III) Complexes in Supercritical CO<sub>2</sub>

Gao, Chunxia; Shin, Wooseob; Han, Ji Sang; Han, Donggyun; Chari, M. Adharvana; Kim, Hong-Doo; Ahn, Kwang‐Hyun

doi:10.5012/bkcs.2009.30.3.541

Cited by 8 publications

(2 citation statements)

References 13 publications

(7 reference statements)

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“…A sufficient amount of research with metallic catalysts has been done, where catalysts such as titanium on amorphous silicon dioxide have shown high efficiency and exhibited no side reactions related to opening of the oxirane ring . Furthermore, the use of methyltrioxomolybdenum and -rhenium as catalysts has demonstrated the lowest quantity of hydrogen peroxide needed and the shortest reaction time compared to conventional methods. , A few more unconventional methods have been proposed, e.g., epoxidation with the application of dioxiranes and epoxidation with the use of supercritical carbon dioxide. , …”

Section: Introductionmentioning

confidence: 99%

“…22,23 A few more unconventional methods have been proposed, e.g., epoxidation with the application of dioxiranes and epoxidation with the use of supercritical carbon dioxide. 24,25 In recent years, a new trend has emerged where an enzymatic approach to epoxidation is utilized. What is special about the chemo-enzymatic approach is that there is no need for an additional carboxylic acid as the reaction carrier since the carboxylic group in the fatty acid takes that role.…”

Section: Introductionmentioning

confidence: 99%

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Fatty Acid Epoxidation on Enzymes: Experimental Study and Modeling of Batch and Semibatch Operation

Wikström

Aguilera

Tolvanen

et al. 2023

Ind. Eng. Chem. Res.

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Biolubricants, plasticizers, bio-based rigid foams, and nonisocyanate polyurethanes can be made in a green way from epoxidized fatty acids. The classical technology for fatty acid epoxidation requires a reaction carrier, which acts as the real epoxidation agent. The process is complicated and involves a safety risk because of the appearance of percarboxylic acids. Therefore, the direct epoxidation of fatty acids in the presence of an immobilized enzyme is an attractive pathway to epoxidized fatty acids. Oleic acid was used as the model compound is this work, and commercial immobilized lipase Novozym 435 was used as the catalyst and hydrogen peroxide as the epoxidation agent. Batch and semibatch operation modes were tested in a laboratory-scale stirred tank reactor. The experimental results showed that almost complete conversions of the double bonds in oleic acid were achievable under isothermal batch and semibatch operation, with low concentrations of ring-opening byproducts. Semibatch operation gave an improvement of the product yield. Mathematical modeling of the experimental data was based on the reaction stoichiometry OA + HP → POA + W and OA + POA → EOA + OA, where OA = oleic acid, HP = hydrogen peroxide, POA = peroleic acid, W = water, and EOA = epoxized OA. Rate equations for the formation of peroleic acid and epoxide were derived, and the numerical values of the kinetic and adsorption parameters were estimated with nonlinear regression analysis. The reactor models consisted of ordinary differential equations, which were solved numerically during the parameter estimation until the optimal parameter values were reached. The model gave a very good description of the experimental data.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fatty Acid Epoxidation on Enzymes: Experimental Study and Modeling of Batch and Semibatch Operation

Wikström

Aguilera

Tolvanen

et al. 2023

Ind. Eng. Chem. Res.

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ChemInform Abstract: A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen‐Mn(III) Complexes in Supercritical CO₂.

et al. 2009

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2 . -Moderate enantioselectivity values are observed in the epoxidation reactions of several olefins under optimized conditions. The enantioselectivities are slightly improved when a more sterically hindered catalyst is used. Besides the green protocol, another important feature of this procedure is the stability of the epoxides under these conditions. The epoxidation of cis-β-methylstyrene (III) yields the cis-β-methylstyrene oxide (IV) with 47% enantiomeric excess. However, a large amount of trans-epoxide is also produced. -(GAO, C.; SHIN, W.; HAN, J.; HAN, D.; CHARI, M. A.; KIM, H.; AHN*, K.-H.; Bull. Korean Chem.

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Homogeneous Catalysis in Supercritical Fluids

Erkey¹

2011

Supercritical Fluid Science and Technology

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A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen-Mn(III) Complexes in Supercritical CO₂

Cited by 8 publications

References 13 publications

Fatty Acid Epoxidation on Enzymes: Experimental Study and Modeling of Batch and Semibatch Operation

Fatty Acid Epoxidation on Enzymes: Experimental Study and Modeling of Batch and Semibatch Operation

ChemInform Abstract: A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen‐Mn(III) Complexes in Supercritical CO₂.

Homogeneous Catalysis in Supercritical Fluids

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A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen-Mn(III) Complexes in Supercritical CO2

Cited by 8 publications

References 13 publications

Fatty Acid Epoxidation on Enzymes: Experimental Study and Modeling of Batch and Semibatch Operation

Fatty Acid Epoxidation on Enzymes: Experimental Study and Modeling of Batch and Semibatch Operation

ChemInform Abstract: A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen‐Mn(III) Complexes in Supercritical CO2.

Homogeneous Catalysis in Supercritical Fluids

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A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen-Mn(III) Complexes in Supercritical CO₂

ChemInform Abstract: A Green Protocol for Asymmetric Epoxidation of Olefins Catalyzed by Carbon Dioxide Soluble Chiral Salen‐Mn(III) Complexes in Supercritical CO₂.