Epoxidation of oleic acid with oxygen in the presence of benzaldehyde using heterogenized homogeneous co‐type ion‐exchange membrane as catalyst

Kuo, M.C.T.; Chou, Tse‐Chuan

doi:10.1002/cjce.5450680514

Cited by 12 publications

(9 citation statements)

References 18 publications

(25 reference statements)

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“…Formation of the ternary complex can be depicted as follows: where A = oleic acid, E = free enzyme, B = hydrogen peroxide, AE = enzyme-oleic acid complex, ABE = ternary complex of the enzyme + oleic acid + hydrogen peroxide, EQ = enzymeperoleic acid complex, P = water, and Q = peroleic acid. The rate or velocity (v) equation obtained with the above mechanism is as follows: [2] where V max = maximum velocity, K iA = dissociation constant for enzyme-oleic acid complex, K mA = Michaelis constant for oleic acid, K mB = Michaelis constant for hydrogen peroxide, and K 1 i = inhibition constant due to hydrogen peroxide. Based on crystallographic and molecular modeling studies of Lipase B from C. antarctica, it is postulated that the active site pocket can be partitioned into two sides, an acyl side and an alcohol side, where the corresponding parts of the substrate will be located during catalysis (16).…”

Section: Resultsmentioning

confidence: 99%

A kinetic model for the enzyme‐catalyzed self‐epoxidation of oleic acid

Yadav

Devi

2001

J Americ Oil Chem Soc

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This paper reports a kinetic model for the selfepoxidation of oleic acid with toluene as solvent and Novozym 435 (a commercially available preparation of immobilized Candida antarctica lipase) as catalyst at 30°C. The effects of various parameters on the conversion and rates of reaction were studied. Both the initial rate and the progress curve data were used to fit an ordered bi-bi model. At low temperatures, the rate of epoxidation was faster than the rate of deactivation of the enzyme by hydrogen peroxide.Paper no. J9531 in JAOCS 78, 347-351 (April 2001).Epoxidation of olefinic compounds leads to the formation of commercially important precursors that are employed to manufacture glycols, alcohols, carbonyls, alkanolamines, substituted olefins, polyesters, polyurethanes, and epoxy resins. The unsaturation present in fatty acid molecules and their corresponding esters can be harnessed to prepare a gamut of epoxidized compounds. For instance, epoxides of soybean and other vegetable oils have been employed as plasticizers and stabilizers for the plastics of polyvinyl chloride (PVC) and other related resins to improve the flexibility, elasticity, and toughness of the plastics and also to impart thermal and photo stability. Among the various chemical routes available for the synthesis of epoxidized oils, the most important and widely applied one involves the use of a suitable organic peracid (1-4) with an unsaturated oil. The next important process is the oxidation of unsaturated compounds in the presence of aldehydes (5). However, the disadvantage of the latter process is that the aldehyde should be taken in stoichiometric quantities with the acid, leading to by-product formation. As compared to chemical processes, enzyme-catalyzed epoxidations are advantageous from several viewpoints, such as mild reaction conditions and high selectivity/specificity with little or no by-product formation. Self-epoxidation of unsaturated acids with hydrogen peroxide in the presence of a lipase is a novel application of enzyme catalysis (6) because by-products, such as dihydroxy acids and estolides, that are so common in the epoxidation of fatty acids by chemical routes are not formed in lipase-catalyzed epoxidations; the only by-product is a small amount of epoxy-peroxy acid. The formation of carboxylic

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Section: Resultsmentioning

confidence: 99%

A kinetic model for the enzyme‐catalyzed self‐epoxidation of oleic acid

Yadav

Devi

2001

J Americ Oil Chem Soc

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“…Thus, it would be interesting to replace the processes based on peracids by a more desirable catalytic one. [8][9][10][11][12] Recently, it has been shown that the incorporation of Ti into the framework of zeolites produce oxidation catalysts with unique shape-selective properties. 13 Large-pore Ti-b zeolite 14 and the mesoporous material Ti-MCM-41, 15 when properly prepared, are active for the selective oxidation of bulky substrates that can not diffuse inside the Ti-silicalite channels.…”

mentioning

confidence: 99%

Epoxidation of unsaturated fatty esters over large-pore Ti-containing molecular sieves as catalysts: important role of the hydrophobic–hydrophilic properties of the molecular sieve

Camblor¹,

Corma²,

Esteve³

et al. 1997

Chem. Commun.

109

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“…This reaction has been applied to the epoxidation of unsaturated fatty acid derivatives. Surprisingly, the epoxidation was mainly carried out using benzaldehyde . Despite this, both high yield and selectivity toward epoxide were achieved.…”

Section: Introductionmentioning

confidence: 99%

Epoxidation of methyl oleate with molecular oxygen: Implementation of Mukaiyama reaction in flow

Vanoye

Hamami

Wang

et al. 2016

Euro J Lipid Sci & Tech

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Continuous‐flow technology with channel dimension in the millimeter region found widespread applications in numerous applications. The epoxidation of methyl oleate with molecular oxygen using an aldehyde as sacrificial reductant (Mukaiyama reaction) was implemented in a segmented flow microreactor. The effect of aldehyde structure and aldehyde/methyl oleate molar ratio on the conversion to epoxides was studied. Total conversion of methyl oleate (0.67 M in heptane) with a selectivity higher than 99% and a cis/trans ratio ∼75/25 was reach in less than 4 min, at room temperature, using three equivalents of 2‐ethylhexanal, 100 ppm of Mn(II) as catalyst and five bar of oxygen. Practical applications: As the result of the small reactor volumes, very high surface‐to‐volume ratio and high heat exchange efficiency compared to classical batch reactors, the overall safety of oxidation processes is significantly improved using continuous‐flow technology. Microreactors also provide better mass transfer, and thus, improve the productivity of the aerobic epoxidation of methyl oleate using aldehyde as sacrificial reductant while maintaining the high selectivity of the process. (i) Epoxidation of methyl oleate with molecular oxygen is performed safely using continuous‐flow technology. (ii) Total conversion is obtained in 4 min at r.t. using 100 ppm of Mn(II) and a sacrificial reductant. (iii) The selectivity and cis/trans ratio are comparable to batch.

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Epoxidation of oleic acid with oxygen in the presence of benzaldehyde using heterogenized homogeneous co‐type ion‐exchange membrane as catalyst

Cited by 12 publications

References 18 publications

A kinetic model for the enzyme‐catalyzed self‐epoxidation of oleic acid

A kinetic model for the enzyme‐catalyzed self‐epoxidation of oleic acid

Epoxidation of unsaturated fatty esters over large-pore Ti-containing molecular sieves as catalysts: important role of the hydrophobic–hydrophilic properties of the molecular sieve

Epoxidation of methyl oleate with molecular oxygen: Implementation of Mukaiyama reaction in flow

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