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Thermal risk assessment of vegetable oil epoxidation

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Abstract

This article describes thermal risk assessment of vegetable oil epoxidation by peroxycarboxylic acid. It is a liquid–liquid system where several exothermic reactions occur. Acetic acid was used as the carboxylic acid, and oleic acid was chosen as a model molecule because it is a common fatty acid in the triglyceride molecule. Differential scanning calorimetry (DSC) and accelerating rate calorimetry (ARC) were used to determine safety criteria such as the final temperature (T Final), T D24, and time to maximum rate under adiabatic condition (TMRad). We found that the calculation of TMRad based on DSC data could be incorrect when assuming a zero-order kinetic reaction. By using a process temperature of 70 °C, the extrapolated final temperature was found to be 544 °C from DSC experiments, T D24 was estimated to 20 °C based on ARC experiment, and TMRad was calculated to 164 min from ARC experiments. These criteria indicate the process can lead to a thermal runaway. Therefore, we recommend that vegetable oil epoxidation by peroxycarboxylic acid should not be performed in batch reactor, but in semi-batch mode.

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References

  1. Anastas PT, Warner JC. Green chemistry: theory and practice. Oxford: Oxford University Press; 2000.

    Google Scholar 

  2. Noyori R. Pursuing practical elegance in chemical synthesis. Chem Commun. 2005;14:1807–11.

    Article  Google Scholar 

  3. Meier MAR, Metzger JO, Schubert US. Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev. 2007;36:1788.

    Article  CAS  Google Scholar 

  4. Xia Y, Larock RC. Vegetable oil-based polymeric materials: synthesis, properties, and applications. Green Chem. 2010;12:1893–909.

    Article  CAS  Google Scholar 

  5. Hernández N, Williams RC, Cochran EW. The battle for the “green” polymer. Different approaches for biopolymer synthesis: bioadvantaged vs. bioreplacement. Org Biomol Chem. 2014;12:2834–49.

    Article  Google Scholar 

  6. Köckritz A, Martin A. Oxidation of unsaturated fatty acid derivatives and vegetable oils. Eur J Lipid Sci Technol. 2008;110:812–24.

    Article  Google Scholar 

  7. Di Serio M, Turco R, Pernice P, Aronne A, Sannino F, Santacesaria E. Valuation of Nb2O5–SiO2 catalysts in soybean oil epoxidation. Catal Today. 2012;192:112–6.

    Article  Google Scholar 

  8. Arends IWCE, Sheldon RA. Recent developments in selective catalytic epoxidations with H2O2. Top Catal. 2002;19:133–41.

    Article  CAS  Google Scholar 

  9. Bunton CA, Lewis TA, Llewelyn DL. Tracer studies in the formation and reactions of organic per-acids. J Am Chem Soc. 1956;78(6):1226–30.

    Article  Google Scholar 

  10. Shi H, Zhang Z, Wang Y. Mechanism on epoxidation of alkenes by peracids: a protonation-promoted pathway and its quantum chemical elucidation. J Mol Catal A Chem. 2005;238:13–25.

    Article  CAS  Google Scholar 

  11. Sinadinović-Fišer S, Janković M, Borota O. Epoxidation of castor oil with peracetic acid formed in situ in the presence of an ion exchange resin. Chem Eng Proc. 2012;62:106–13.

    Article  Google Scholar 

  12. Turco T. Industrial catalytic processes intensification through the use of microreactors. PhD dissertation, The University of Naples Federico II, Naples, 2010.

  13. Leveneur S, Wärnå J, Salmi T, Murzin DY. A review: catalytic synthesis and decomposition of peroxycarboxylic acids. Trends Chem Eng. 2010;13:17–52.

    CAS  Google Scholar 

  14. Leveneur S, Thönes M, Hébert J-P, Taouk B, Salmi T. From kinetic study to thermal safety assessment: application to peroxyformic acid synthesis. Ind Eng Chem Res. 2012;51(13999):14007.

    Google Scholar 

  15. Stoessel F. Thermal safety of chemical processes. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA; 2008.

    Book  Google Scholar 

  16. Sun D-X, Miao X, Xie C-X, Gu J, Li R. Study on thermal properties and kinetics of benzoyl peroxide by ARC and C80 methods. J Therm Anal Calorim. 2012;107:943–8.

    Article  CAS  Google Scholar 

  17. Wu S-H, Chou H-C, Pan R-N, Huang Y-H, Horng J-J, Chi J-H, Shu C-M. Thermal hazard analyses of organic peroxides and inorganic peroxides by calorimetric approaches. J Therm Anal Calorim. 2012;109:355–64.

    Article  CAS  Google Scholar 

  18. Cheng S-Y, Tseng J-M, Lin S-Y, Gupta JP, Shu C-M. Runaway reaction on tert-butyl peroxybenzoate by DSC tests. J Therm Anal Calorim. 2008;93:121–6.

    Article  CAS  Google Scholar 

  19. Casson V, Maschio G. Screening analysis for hazard assessment of peroxides decomposition. Ind Eng Chem Res. 2012;51:7526–35.

    Article  CAS  Google Scholar 

  20. Wu S-H, Chi J-H, Huang C-C, Lin N-K, Peng J-J, Shu C-M. Thermal hazard analyses and incompatible reaction evaluation of hydrogen peroxide by DSC. J Therm Anal Calorim. 2010;102:563–8.

    Article  CAS  Google Scholar 

  21. You M-L, Tseng J-M, Liu M-Y, Shu C-M. Runaway reaction of lauroyl peroxide with nitric acid by DSC. J Therm Anal Calorim. 2010;102:535–9.

    Article  CAS  Google Scholar 

  22. Chi J-H, Wu S-H, Charpentier J-C, Yet-Pole I, Shu C-M. Thermal hazard accident investigation of hydrogen peroxide mixing with propanone employing calorimetric approaches. J Loss Prev Process Ind. 2012;25:142–7.

    Article  CAS  Google Scholar 

  23. Salzano E, Agreda AG, Russo V, Di Serio M, Santacesaria E. Safety criteria for the epoxydation of soybean oil in fed- batch reactor. Chem Eng Trans. 2012;. doi:10.3303/CET1226007.

    Google Scholar 

  24. Leveneur S, Delannoy F, Levesqueau Y, Hebert J-P, Estel L, Taouk B, Salmi T. The limit of DSC as a preliminary tool to determine the safety parameters? Chem Eng Trans. 2014;. doi:10.3303/CET1436024.

    Google Scholar 

  25. Keller A, Stark D, Fierz H, Heinzle E, Hungerbühler K. Estimation of the time to maximum rate using dynamic DSC experiments. J Loss Prev Process Ind. 1997;10:31–41.

    Article  Google Scholar 

  26. Blaine RL, Kissinger HE. Homer Kissinger and the Kissinger equation. Thermochim Acta. 2012;540:1–6.

    Article  CAS  Google Scholar 

  27. Musakka N, Salmi T, Wärnå J, Ahlkvist J, Piironen M. Modelling of organic liquid-phase decomposition reactions through gas-phase product analysis: model systems and peracetic acid. Chem Eng Sci. 2006;61:6918–28.

    Article  CAS  Google Scholar 

  28. Leveneur S, Salmi T, Musakka N, Wärnå J. Kinetic study of decomposition of peroxypropionic acid in liquid phase through direct analysis of decomposition products in gas phase. Chem Eng Sci. 2007;62:5007–12.

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the Academy of Finland and the European Regional Development Fund (INTERREG IVA Grant Number 4274). The authors are particularly grateful to Jean-Pierre Hébert for his contribution to the experiment.

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Authors and Affiliations

  1. Laboratoire de Sécurité des Procédés Chimiques (LSPC), EA4704, Normandie Université, INSA Rouen, 685 Avenue de l’université, BP08, 76801, Saint-Etienne-du-Rouvray, France

    Sébastien Leveneur & Lionel Estel

  2. School of Computing, Engineering and Mathematics, University of Brighton, Brighton, BN2 4GJ, UK

    Cyril Crua

  3. Laboratory of Industrial Chemistry and Reaction Engineering, Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, 20500, Åbo/Turku, Finland

    Sébastien Leveneur

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  1. Sébastien Leveneur
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  2. Lionel Estel
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  3. Cyril Crua
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Correspondence to Sébastien Leveneur.

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Leveneur, S., Estel, L. & Crua, C. Thermal risk assessment of vegetable oil epoxidation. J Therm Anal Calorim 122, 795–804 (2015). https://doi.org/10.1007/s10973-015-4793-8

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  • DOI: https://doi.org/10.1007/s10973-015-4793-8

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