---
_id: '13671'
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.
article_number: '139339'
author:
- first_name: Julian
  full_name: Türck, Julian
  last_name: Türck
- first_name: Carsten
  full_name: Funke, Carsten
  id: '74167'
  last_name: Funke
- first_name: Fabian
  full_name: Schmitt, Fabian
  last_name: Schmitt
- first_name: Jan
  full_name: Schneider, Jan
  id: '13209'
  last_name: Schneider
  orcid: 0000-0001-6401-8873
- first_name: Hans-Jürgen
  full_name: Danneel, Hans-Jürgen
  id: '12231'
  last_name: Danneel
- first_name: Ralf
  full_name: Türck, Ralf
  last_name: Türck
- first_name: Wolfgang
  full_name: Ruck, Wolfgang
  last_name: Ruck
- first_name: Jürgen
  full_name: Krahl, Jürgen
  id: '68870'
  last_name: Krahl
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>'
  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>'
  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>.'
  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>.'
  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)'
  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).'
  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>.'
  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>.'
  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).'
  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).'
  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.'
date_created: 2026-04-07T12:49:23Z
date_updated: 2026-04-08T12:55:00Z
doi: 10.1016/j.fuel.2026.139339
intvolume: '       424'
keyword:
- Biodiesel aging
- Epoxide-dependent oligomerization
- Acetic acid
- Identification of aging products
- Kinetics of aging products
language:
- iso: eng
place: Amsterdam [u.a.]
publication: 'Fuel : the science and technology of fuel and energy '
publication_identifier:
  eissn:
  - 1873-7153
  issn:
  - 0016-2361
publication_status: published
publisher: Elsevier
quality_controlled: '1'
status: public
title: Kinetic study and confirmation of epoxide-dependent oligomerization of methyl
  oleate
type: scientific_journal_article
user_id: '83781'
volume: 424
year: '2026'
...
---
_id: '12823'
abstract:
- lang: eng
  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.
author:
- first_name: Julian
  full_name: Türck, Julian
  last_name: Türck
- first_name: Fabian
  full_name: Schmitt, Fabian
  last_name: Schmitt
- first_name: Lukas
  full_name: Anthofer, Lukas
  last_name: Anthofer
- first_name: Ralf
  full_name: Türck, Ralf
  last_name: Türck
- first_name: Wolfgang
  full_name: Ruck, Wolfgang
  last_name: Ruck
- first_name: Jürgen
  full_name: Krahl, Jürgen
  id: '68870'
  last_name: Krahl
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>'
  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>'
  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>.'
  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>.'
  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'
  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).'
  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>.'
  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>.'
  short: 'J. Türck, F. Schmitt, L. Anthofer, R. Türck, W. Ruck, J. Krahl,   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.'
  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).'
date_created: 2025-04-22T13:38:51Z
date_updated: 2025-06-26T07:47:02Z
department:
- _id: DEP1408
doi: 10.1002/cssc.202300263
external_id:
  isi:
  - '001025502300001'
  pmid:
  - '37220243'
intvolume: '        16'
isi: '1'
issue: '17'
keyword:
- biodiesel aging
- epoxide-dependent oligomerization
- solketal
- Prileschajew reaction
language:
- iso: eng
place: Weinheim
pmid: '1'
publication: '  ChemSusChem : chemistry & sustainability, energy & materials'
publication_identifier:
  eissn:
  - 1864-564X
  issn:
  - 1864-5631
publication_status: published
publisher: Wiley
status: public
title: Extension of Biodiesel Aging Mechanism–the Role and Influence of Methyl Oleate
  and the Contribution of Alcohols Through the Use of Solketal
type: scientific_journal_article
user_id: '83781'
volume: 16
year: '2023'
...