Catalytic synthesis of methyl 9,10‐dihydroxystearate from technical feedstocks in continuous flow via epoxidation and hydrolysis

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dc.contributor.authorVondran, Johanna
dc.contributor.authorBenninghoff, Tobias
dc.contributor.authorEmminghaus, Anahita Irene
dc.contributor.authorSeidensticker, Thomas
dc.date.accessioned2024-02-16T12:09:42Z
dc.date.available2024-02-16T12:09:42Z
dc.date.issued2022-04-30
dc.description.abstractThe sequence of the homogeneously Ru-catalyzed epoxidation of methyl oleate and acid-catalyzed hydrolysis of the corresponding epoxide methyl 9,10-epoxy stearate is successfully transferred from batch into flow mode, allowing for the continuous production of methyl 9,10-dihydroxystearate. Thereby, methyl oleate is first converted up to 97% within 14 min at excellent selectivity in the epoxidation using aqueous hydrogen peroxide as the sole oxidant. In the subsequent hydrolysis, a residence time of 10 min is sufficient for quantitative conversion of the epoxide. The desired, pure vicinal diol is isolated upon crystallization from the crude reaction mixture in an integrated process starting from technical grade (91.5%) substrate. The isolated yield is increased upon the addition of water as a green antisolvent from 75% up to 97%. Finally, the concept is transferred to methyl oleate of even lower purity (76%), still obtaining an isolated yield of 66% of the vicinal diol. Thus, the integration of sequential epoxidation and hydrolysis into continuous flow and subsequent crystallization allows for high conversion and selectivities within a total residence time of 27 min, corresponding to a space–time yield of 190 g h−1 L−1 in the epoxidation and 164 g h−1 L−1 in the hydrolysis, respectively. Practical applications: The modular flow setup enables the targeted functionalization toward the epoxide intermediate or the vicinal diol. Both offer versatile applications for the production of polymers, surfactants, or toward further conversion as in oxidative cleavage starting from methyl oleate. The application of flow chemistry offers advantages for the safe handling of hydrogen peroxide even at high temperatures. With fats and oils being natural substances, oleochemicals such as fatty acid methyl esters are typically available in technical purity so that efficient strategies for the isolation of pure products are of need. Crystallization of the product is promising, as additional organic solvents are not required. Thus, using the difference in melting point and solubility behavior of the desired product compared to other compounds is a promising method for the applicability of renewable resource-based substrate mixtures.en
dc.identifier.urihttp://hdl.handle.net/2003/42336
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-24173
dc.language.isoende
dc.relation.ispartofseriesEuropean journal of lipid science and technology;124(7)
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/de
dc.subjectCrystallizationen
dc.subjectFlow chemistryen
dc.subjectHomogeneous catalysisen
dc.subjectHydrogen peroxideen
dc.subjectMethyl oleateen
dc.subject.ddc660
dc.subject.rswkKristallisationde
dc.subject.rswkReagierende Strömungde
dc.subject.rswkHomogene Katalysede
dc.subject.rswkWasserstoffperoxidde
dc.subject.rswkOleatede
dc.titleCatalytic synthesis of methyl 9,10‐dihydroxystearate from technical feedstocks in continuous flow via epoxidation and hydrolysisen
dc.typeTextde
dc.type.publicationtypeResearchArticlede
dcterms.accessRightsopen access
eldorado.secondarypublicationtruede
eldorado.secondarypublication.primarycitationJ. Vondran, T. Benninghoff, A. I. Emminghaus, T. Seidensticker, Catalytic Synthesis of Methyl 9,10-dihydroxystearate from Technical Feedstocks in Continuous Flow via Epoxidation and Hydrolysis. Eur. J. Lipid Sci. Technol. 2022, 124, 2200041. https://doi.org/10.1002/ejlt.202200041de
eldorado.secondarypublication.primaryidentifierhttps://doi.org/10.1002/ejlt.202200041de

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