1. Epoxidation of methyl oleate with molecular oxygen: Implementation of Mukaiyama reaction in flow
- Author
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Laurent Vanoye, Zine Eddine Hamami, Pascal Fongarland, Jiady Wang, Alain Favre-Réguillon, Claude de Bellefon, Laboratoire de Génie des Procédés Catalytiques (LGPC), École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, Institut de recherches sur la catalyse et l'environnement de Lyon (IRCELYON), Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Inorganic chemistry ,chemistry.chemical_element ,010402 general chemistry ,7. Clean energy ,01 natural sciences ,Oxygen ,Aldehyde ,Industrial and Manufacturing Engineering ,Catalysis ,chemistry.chemical_compound ,[CHIM.GENI]Chemical Sciences/Chemical engineering ,Mass transfer ,Organic chemistry ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,ComputingMilieux_MISCELLANEOUS ,chemistry.chemical_classification ,Heptane ,010405 organic chemistry ,General Chemistry ,[CHIM.CATA]Chemical Sciences/Catalysis ,6. Clean water ,0104 chemical sciences ,chemistry ,Molecular oxygen ,Microreactor ,Selectivity ,Food Science ,Biotechnology - Abstract
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.
- Published
- 2017
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