[{"user_id":"83781","intvolume":"       424","type":"scientific_journal_article","place":"Amsterdam [u.a.]","_id":"13671","article_number":"139339","doi":"10.1016/j.fuel.2026.139339","publication_status":"published","publisher":"Elsevier","quality_controlled":"1","abstract":[{"lang":"eng","text":"The aging of biodiesel proceeds via multiple pathways, with oligomerization playing a central role. In this study, we investigated an epoxide-dependent oligomerization pathway, which had previously only been postulated. Using methyl oleate (C18:1) as a model monounsaturated fatty acid and acetic acid as a representative, reactive nucleophile and known biodiesel aging product with a suitable boiling point, oligomeric products were identified by size-exclusion chromatography (SEC) coupled with electrospray ionization quadrupole time-of-flight mass spectrometry (ESI-QTOF-MS). The concentration of 20 wt% was chosen to ensure a measurable kinetic effect while maintaining stable reaction conditions. Furthermore, the role of methyl oleate during biodiesel aging was addressed. Time-resolved analysis confirmed the proposed sequential order of reactions. It was pointed out that elimination reactions may occur. The data support the formation of epoxides, despite the isobaric overlap with ketones, and show that hydroxyl intermediates undergo esterification and etherification. Moreover, experiments with pure C18:1 demonstrated that acetic acid–derived oligomers are generated. Under Rancimat conditions, addition of 20 wt% acetic acid resulted in an approximately 1.1 – 2.6 increase in product yield. Kinetic analysis revealed structure-dependent formation and decay behavior of the aging products, with slightly faster epoxidation and shifted product distributions toward higher oligomeric species in the presence of acetic acid. Reactive intermediates were consumed more rapidly than oligomeric species and all decay processes followed apparent second-order kinetics. These findings provide direct experimental evidence for the involvement of epoxide-dependent pathways in biodiesel aging."}],"date_updated":"2026-04-08T12:55:00Z","publication":"Fuel : the science and technology of fuel and energy ","publication_identifier":{"issn":["0016-2361"],"eissn":["1873-7153"]},"date_created":"2026-04-07T12:49:23Z","keyword":["Biodiesel aging","Epoxide-dependent oligomerization","Acetic acid","Identification of aging products","Kinetics of aging products"],"language":[{"iso":"eng"}],"citation":{"ama":"Türck J, Funke C, Schmitt F, et al. Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate. <i>Fuel : the science and technology of fuel and energy </i>. 2026;424. doi:<a href=\"https://doi.org/10.1016/j.fuel.2026.139339\">10.1016/j.fuel.2026.139339</a>","van":"Türck J, Funke C, Schmitt F, Schneider J, Danneel HJ, Türck R, et al. Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate. Fuel : the science and technology of fuel and energy . 2026;424.","havard":"J. Türck, C. Funke, F. Schmitt, J. Schneider, H.-J. Danneel, R. Türck, W. Ruck, J. Krahl, Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate, Fuel : The Science and Technology of Fuel and Energy . 424 (2026).","bjps":"<b>Türck J <i>et al.</i></b> (2026) Kinetic Study and Confirmation of Epoxide-Dependent Oligomerization of Methyl Oleate. <i>Fuel : the science and technology of fuel and energy </i> <b>424</b>.","mla":"Türck, Julian, et al. “Kinetic Study and Confirmation of Epoxide-Dependent Oligomerization of Methyl Oleate.” <i>Fuel : The Science and Technology of Fuel and Energy </i>, vol. 424, 139339, 2026, <a href=\"https://doi.org/10.1016/j.fuel.2026.139339\">https://doi.org/10.1016/j.fuel.2026.139339</a>.","ufg":"<b>Türck, Julian u. a.</b>: Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate, in: <i>Fuel : the science and technology of fuel and energy </i> 424 (2026).","ieee":"J. Türck <i>et al.</i>, “Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate,” <i>Fuel : the science and technology of fuel and energy </i>, vol. 424, Art. no. 139339, 2026, doi: <a href=\"https://doi.org/10.1016/j.fuel.2026.139339\">10.1016/j.fuel.2026.139339</a>.","apa":"Türck, J., Funke, C., Schmitt, F., Schneider, J., Danneel, H.-J., Türck, R., Ruck, W., &#38; Krahl, J. (2026). Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate. <i>Fuel : The Science and Technology of Fuel and Energy </i>, <i>424</i>, Article 139339. <a href=\"https://doi.org/10.1016/j.fuel.2026.139339\">https://doi.org/10.1016/j.fuel.2026.139339</a>","chicago":"Türck, Julian, Carsten Funke, Fabian Schmitt, Jan Schneider, Hans-Jürgen Danneel, Ralf Türck, Wolfgang Ruck, and Jürgen Krahl. “Kinetic Study and Confirmation of Epoxide-Dependent Oligomerization of Methyl Oleate.” <i>Fuel : The Science and Technology of Fuel and Energy </i> 424 (2026). <a href=\"https://doi.org/10.1016/j.fuel.2026.139339\">https://doi.org/10.1016/j.fuel.2026.139339</a>.","short":"J. Türck, C. Funke, F. Schmitt, J. Schneider, H.-J. Danneel, R. Türck, W. Ruck, J. Krahl, Fuel : The Science and Technology of Fuel and Energy  424 (2026).","chicago-de":"Türck, Julian, Carsten Funke, Fabian Schmitt, Jan Schneider, Hans-Jürgen Danneel, Ralf Türck, Wolfgang Ruck und Jürgen Krahl. 2026. Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate. <i>Fuel : the science and technology of fuel and energy </i> 424. doi:<a href=\"https://doi.org/10.1016/j.fuel.2026.139339\">10.1016/j.fuel.2026.139339</a>, .","din1505-2-1":"<span style=\"font-variant:small-caps;\">Türck, Julian</span> ; <span style=\"font-variant:small-caps;\">Funke, Carsten</span> ; <span style=\"font-variant:small-caps;\">Schmitt, Fabian</span> ; <span style=\"font-variant:small-caps;\">Schneider, Jan</span> ; <span style=\"font-variant:small-caps;\">Danneel, Hans-Jürgen</span> ; <span style=\"font-variant:small-caps;\">Türck, Ralf</span> ; <span style=\"font-variant:small-caps;\">Ruck, Wolfgang</span> ; <span style=\"font-variant:small-caps;\">Krahl, Jürgen</span>: Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate. In: <i>Fuel : the science and technology of fuel and energy </i> Bd. 424. Amsterdam [u.a.], Elsevier (2026)"},"volume":424,"title":"Kinetic study and confirmation of epoxide-dependent oligomerization of methyl oleate","status":"public","author":[{"full_name":"Türck, Julian","first_name":"Julian","last_name":"Türck"},{"full_name":"Funke, Carsten","first_name":"Carsten","id":"74167","last_name":"Funke"},{"last_name":"Schmitt","first_name":"Fabian","full_name":"Schmitt, Fabian"},{"orcid":"0000-0001-6401-8873","first_name":"Jan","last_name":"Schneider","id":"13209","full_name":"Schneider, Jan"},{"id":"12231","full_name":"Danneel, Hans-Jürgen","last_name":"Danneel","first_name":"Hans-Jürgen"},{"first_name":"Ralf","last_name":"Türck","full_name":"Türck, Ralf"},{"last_name":"Ruck","first_name":"Wolfgang","full_name":"Ruck, Wolfgang"},{"first_name":"Jürgen","full_name":"Krahl, Jürgen","last_name":"Krahl","id":"68870"}],"year":"2026"},{"place":"Weinheim","doi":"10.1002/cssc.202300263","_id":"12823","user_id":"83781","intvolume":"        16","type":"scientific_journal_article","publisher":"Wiley","department":[{"_id":"DEP1408"}],"abstract":[{"text":"The energy crisis and dependence on fossil fuels forces societies to develop alternative pathways to secure energy supplies. Therefore, non‐fossil fuels such as biofuels and e‐fuels can help counteract the resulting demand for existing combustion engines. However, biofuels, like biodiesel, have disadvantages in terms of oxidation stability. In general, aging of biodiesel is a complex mechanism due to interaction of various components. In order to develop an ideal fuel, the mechanism must be understood in full detail. In this work, an attempt is made to simplify the system by using methyl oleate as a biodiesel model component. In addition, other fuel components of interest such as alcohols and their respective acids help to clarify the aging mechanism. This work used isopropylidene glycerol (solketal) as the main alcohol, 1‐octanol and octanoic acid. A holistic biodiesel aging scheme was developed by using generated data and evaluating the role of acids. They epoxidize unsaturated fatty acid via Prileschajev reactions. In addition, the role of epoxides in oligomerization reactions is confirmed. Moreover, the alcohols show that the suppression of oligomerization can be achieved by the reaction with methyl oleate. The alcohol‐dependent aging products were determined by quadrupole time‐of‐flight (Q‐TOF) mass spectrometry.","lang":"eng"}],"issue":"17","publication_status":"published","isi":"1","language":[{"iso":"eng"}],"keyword":["biodiesel aging","epoxide-dependent oligomerization","solketal","Prileschajew reaction"],"date_updated":"2025-06-26T07:47:02Z","date_created":"2025-04-22T13:38:51Z","publication":"  ChemSusChem : chemistry & sustainability, energy & materials","publication_identifier":{"issn":["1864-5631"],"eissn":["1864-564X"]},"pmid":"1","status":"public","author":[{"last_name":"Türck","first_name":"Julian","full_name":"Türck, Julian"},{"full_name":"Schmitt, Fabian","last_name":"Schmitt","first_name":"Fabian"},{"last_name":"Anthofer","first_name":"Lukas","full_name":"Anthofer, Lukas"},{"first_name":"Ralf","full_name":"Türck, Ralf","last_name":"Türck"},{"last_name":"Ruck","first_name":"Wolfgang","full_name":"Ruck, Wolfgang"},{"first_name":"Jürgen","full_name":"Krahl, Jürgen","last_name":"Krahl","id":"68870"}],"year":"2023","external_id":{"pmid":["37220243"],"isi":["001025502300001"]},"citation":{"ama":"Türck J, Schmitt F, Anthofer L, Türck R, Ruck W, Krahl J. Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal. <i>  ChemSusChem : chemistry &#38; sustainability, energy &#38; materials</i>. 2023;16(17). doi:<a href=\"https://doi.org/10.1002/cssc.202300263\">10.1002/cssc.202300263</a>","ieee":"J. Türck, F. Schmitt, L. Anthofer, R. Türck, W. Ruck, and J. Krahl, “Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal,” <i>  ChemSusChem : chemistry &#38; sustainability, energy &#38; materials</i>, vol. 16, no. 17, 2023, doi: <a href=\"https://doi.org/10.1002/cssc.202300263\">10.1002/cssc.202300263</a>.","short":"J. Türck, F. Schmitt, L. Anthofer, R. Türck, W. Ruck, J. Krahl,   ChemSusChem : Chemistry &#38; Sustainability, Energy &#38; Materials 16 (2023).","chicago-de":"Türck, Julian, Fabian Schmitt, Lukas Anthofer, Ralf Türck, Wolfgang Ruck und Jürgen Krahl. 2023. Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal. <i>  ChemSusChem : chemistry &#38; sustainability, energy &#38; materials</i> 16, Nr. 17. doi:<a href=\"https://doi.org/10.1002/cssc.202300263\">10.1002/cssc.202300263</a>, .","din1505-2-1":"<span style=\"font-variant:small-caps;\">Türck, Julian</span> ; <span style=\"font-variant:small-caps;\">Schmitt, Fabian</span> ; <span style=\"font-variant:small-caps;\">Anthofer, Lukas</span> ; <span style=\"font-variant:small-caps;\">Türck, Ralf</span> ; <span style=\"font-variant:small-caps;\">Ruck, Wolfgang</span> ; <span style=\"font-variant:small-caps;\">Krahl, Jürgen</span>: Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal. In: <i>  ChemSusChem : chemistry &#38; sustainability, energy &#38; materials</i> Bd. 16. Weinheim, Wiley (2023), Nr. 17","van":"Türck J, Schmitt F, Anthofer L, Türck R, Ruck W, Krahl J. Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal.   ChemSusChem : chemistry &#38; sustainability, energy &#38; materials. 2023;16(17).","mla":"Türck, Julian, et al. “Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal.” <i>  ChemSusChem : Chemistry &#38; Sustainability, Energy &#38; Materials</i>, vol. 16, no. 17, 2023, <a href=\"https://doi.org/10.1002/cssc.202300263\">https://doi.org/10.1002/cssc.202300263</a>.","bjps":"<b>Türck J <i>et al.</i></b> (2023) Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal. <i>  ChemSusChem : chemistry &#38; sustainability, energy &#38; materials</i> <b>16</b>.","havard":"J. Türck, F. Schmitt, L. Anthofer, R. Türck, W. Ruck, J. Krahl, Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal,   ChemSusChem : Chemistry &#38; Sustainability, Energy &#38; Materials. 16 (2023).","ufg":"<b>Türck, Julian u. a.</b>: Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal, in: <i>  ChemSusChem : chemistry &#38; sustainability, energy &#38; materials</i> 16 (2023), H. 17.","apa":"Türck, J., Schmitt, F., Anthofer, L., Türck, R., Ruck, W., &#38; Krahl, J. (2023). Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal. <i>  ChemSusChem : Chemistry &#38; Sustainability, Energy &#38; Materials</i>, <i>16</i>(17). <a href=\"https://doi.org/10.1002/cssc.202300263\">https://doi.org/10.1002/cssc.202300263</a>","chicago":"Türck, Julian, Fabian Schmitt, Lukas Anthofer, Ralf Türck, Wolfgang Ruck, and Jürgen Krahl. “Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal.” <i>  ChemSusChem : Chemistry &#38; Sustainability, Energy &#38; Materials</i> 16, no. 17 (2023). <a href=\"https://doi.org/10.1002/cssc.202300263\">https://doi.org/10.1002/cssc.202300263</a>."},"volume":16,"title":"Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate and the Contribution of Alcohols Through the Use of Solketal"}]