LAPSE:2021.0126v1
Published Article
LAPSE:2021.0126v1
Soybean Oil Epoxidation: Kinetics of the Epoxide Ring Opening Reactions
Elio Santacesaria, Rosa Turco, Vincenzo Russo, Riccardo Tesser, Martino Di Serio
March 14, 2021
The epoxide ring opening reaction (ROR) can be considered as the most important side reaction occurring in the epoxidation of soybean oil reaction network. This reaction consistently reduces the selectivity to epoxidized soybean oil (ESBO). The reaction is also important for producing polyols and lubricants. In this work, the reaction was studied in different operative conditions to evaluate the effect on ROR rate respectively: (i) The Bronsted acidity of the mineral acid (H2SO4 or H3PO4), used as catalyst for promoting the oxidation with hydrogen peroxide of formic to performic acid, that is, the reactant in the epoxide formation; (ii) the concentration of the nucleophilic agents, normally present during the ESBO synthesis like HCOOH, HCOOOH, H2O, H2O2; (iii) the stirring rate that changes the oil−water interface area and affects the mass transfer rate; (iv) the adopted temperature. Many different kinetic runs were made in different operative conditions, starting from an already epoxidized soybean oil. On the basis of these runs two different reaction mechanisms were hypothesized, one promoted by the Bronsted acidity mainly occurring at the oil−water interface and one promoted by the nucleophilic agents, in particular by formic acid. As it will be seen, the kinetic laws corresponding to the two mentioned mechanisms are quite different and this explain the divergent data reported in the literature on this subject. All the kinetic runs were correctly interpreted with a new developed biphasic kinetic model.
Keywords
epoxides, hydrogen peroxide, kinetics, ring opening reaction, soybean oil
Suggested Citation
Santacesaria E, Turco R, Russo V, Tesser R, Di Serio M. Soybean Oil Epoxidation: Kinetics of the Epoxide Ring Opening Reactions. (2021). LAPSE:2021.0126v1
Author Affiliations
Santacesaria E: CEO of Eurochem Engineering Ltd., 20139 Milano, Italy [ORCID]
Turco R: NICL—Department of Chemical Science, University of Naples Federico II, 80126 Naples, Italy [ORCID]
Russo V: NICL—Department of Chemical Science, University of Naples Federico II, 80126 Naples, Italy [ORCID]
Tesser R: NICL—Department of Chemical Science, University of Naples Federico II, 80126 Naples, Italy
Di Serio M: NICL—Department of Chemical Science, University of Naples Federico II, 80126 Naples, Italy
Journal Name
Processes
Volume
8
Issue
9
Article Number
E1134
Year
2020
Publication Date
2020-09-11
Published Version
ISSN
2227-9717
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Original Submission
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PII: pr8091134, Publication Type: Journal Article
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LAPSE:2021.0126v1
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doi:10.3390/pr8091134
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Mar 14, 2021
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Mar 14, 2021
 
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Mar 14, 2021
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Calvin Tsay
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