Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups

Khlebnikova, T. B.; Pai, Z. P.; Fedoseeva, L. A.; Mattsat, Yulia V.

doi:10.1007/s11144-009-0054-9

Cited by 34 publications

(30 citation statements)

References 10 publications

(17 reference statements)

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“…Later, a number of related papers and patents was published. The authors varied the ammonium phase transfer catalyst, reaction conditions, or molar amount and concentration of H 2 O 2 used (e.g., [62][63][64][65][66]). Depending on these influencing factors the yields of AA varied between 67 and 92%.…”

Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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“…UFAME can be converted into high value‐added products, one of which is the oxidative cleavage of UFAME into aldehyde and carboxylic acid species. These cleavage products can be used to prepare biodegradable products, e.g., plasticizers, synthetic lubricants, and polymers …”

Section: Introductionmentioning

confidence: 99%

“…These cleavage products can be used to prepare biodegradable products, e.g., plasticizers, synthetic lubricants, and polymers. [1][2][3][4] In previous reports, oxidative cleavage of UFAME mostly resulted in carboxylic acids rather than aldehydes. To obtain aldehydes from UFAME, the methods of reductive ozonolysis [5,6] and Fe catalysis [7] are the direct routes that provides fatty aldehydes.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Cleavage of Methyl 9,10‐Epoxystearate over WO₃/MCM‐41 for Methyl 9‐Oxononanoate Production

Peng

Xie

et al. 2018

Euro J Lipid Sci & Tech

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At present, the utilization of grease has attracted more and more attention. This article presents a simple method that efficiently cleaves methyl oleate‐derived methyl 9,10‐epoxystearate (a) to give high yields of methyl 9‐oxononanoate (d) with nonanal (c) as co‐product. A WO3/MCM‐41 catalyst is prepared via direct mixed‐gel synthesis. The catalyst is tested in the oxidative cleavage of a to produce d which can be used as a polymer precursor or an important feedstock. The effects of WO3 loading, temperature, time, H2O2/a molar ratio, catalyst/a weight ratio, and t‐BuOH/a weight ratio on the a conversion and d yield are examined using single‐factor experiments. The optimal reaction conditions are determined by orthogonal experiments. The optimal WO3 loading, temperature, time, H2O2/a molar ratio, catalyst/a weight ratio, and t‐BuOH/a weight ratio are 35%, 80 °C, 20 min, 1.3, 0.04, and 0.5, respectively. Under these conditions, the a conversion and d yield reach 99.4 and 78.4%, respectively. In addition, the catalyst shows no significant decrease in activity after being reused three times. Moreover, the reaction mechanism is studied based on the product distribution over time. Practical Applications: Few studies on methyl 9,10‐epoxystearate used as the raw material to give methyl 9‐oxononanoate and nonanal are found. Because the ethylene oxide bond is more unstable than the carbon–carbon double bond, the oxidative cleavage of methyl 9,10‐epoxystearate is easier than cleavage of methyl oleate that allows the oxidative cleavage to be done under milder conditions. Methyl 9‐oxononanoate can be converted to a monomer of high‐value polymers and is also an important feedstock in the production of chemicals. The co‐product nonanal is a natural spice which can be used in the fragrance industry. The results show that the reaction time is short and methyl 9‐oxononanoate yield is high under mild reaction conditions. The method in this study can also be widely used in other oxidative cleavage reactions of epoxides. Methyl 9,10‐epoxystearate is used as the raw material to produce methyl 9‐oxononanoate with nonanal as co‐product using WO3/MCM‐41 as catalyst and H2O2 as oxidant.

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“…In an oxidation reaction, the reaction rate typically increases as the hydrogen peroxide concentration increases. However, high concentration of hydrogen peroxide may produce undesired side products . Moreover, at high concentration of hydrogen peroxide, explosive mixtures may be produced, which is a major safety concern in the industrial use of hydrogen peroxide.…”

Section: Introductionmentioning

confidence: 99%

“…However, high concentration of hydrogen peroxide may produce undesired side products. 11 Moreover, at high concentration of hydrogen peroxide, explosive mixtures may be produced, which is a major safety concern in the industrial use of hydrogen peroxide. Indeed, the mixture of hydrogen peroxide solutions with concentrations higher than 40 wt % and organic compounds can form explosive mixtures.…”

Section: Introductionmentioning

confidence: 99%

In‐line monitoring of hydrogen peroxide in two‐phase reactions using raman spectroscopy

et al. 2017

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Hydrogen peroxide is an environment‐friendly oxidizer, which is used in several chemical processes. However, safety necessitates the determination and control of the concentration of hydrogen peroxide during oxidation reactions. We propose a methodology to monitor hydrogen peroxide in disperse two‐phase reaction mixtures based on in‐line Raman spectroscopy. We compare indirect hard modeling (IHM), peak integration (PI), and partial least squares (PLS). Building predictive PLS and PI calibration models is challenging, whereas the IHM calibration is easy to develop. These methods show good accuracy for known samples (root mean square error of cross validation [RMSECV] of 0.3–0.7 wt %) compared to the classic titration method (RMSECV of 0.4 wt %). After calibration, inline monitoring during reaction is performed demonstrating that the concentration of hydrogen peroxide can be successfully monitored in a fast and reliable way by Raman spectroscopy. The IHM seems to give slightly better inline predictions. © 2017 American Institute of Chemical Engineers AIChE J, 63: 3994–4002, 2017

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Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups

Cited by 34 publications

References 10 publications

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Oxidative Cleavage of Methyl 9,10‐Epoxystearate over WO₃/MCM‐41 for Methyl 9‐Oxononanoate Production

In‐line monitoring of hydrogen peroxide in two‐phase reactions using raman spectroscopy

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Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups

Cited by 34 publications

References 10 publications

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Oxidative Cleavage of Methyl 9,10‐Epoxystearate over WO3/MCM‐41 for Methyl 9‐Oxononanoate Production

In‐line monitoring of hydrogen peroxide in two‐phase reactions using raman spectroscopy

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Product

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Oxidative Cleavage of Methyl 9,10‐Epoxystearate over WO₃/MCM‐41 for Methyl 9‐Oxononanoate Production