Epoxidation of tall oil catalyzed by an ion exchange resin under conventional heating and microwave irradiation

Adriana Freites Aguilera, Jani Rahkila, Jarl Hemming, Maristiina Nurmi, Gaetan Torres, Théophile Razat, Pasi Tolvanen, Kari Eränen, Sébastien Leveneur, Tapio Salmi*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Tall oil fatty acids (TOFA) are a byproduct from the Kraft pulping process, and they represent a renewable and inexpensive alternative with high potential as a renewable feedstock. Epoxidized TOFA have great potential as chemical intermediates. Epoxidation of oleic acid, TOFA, and distilled tall oil (DTO) was conducted in an isothermal batch reactor with in situ-formed peracetic acid using hydrogen peroxide as the reactant and acetic acid as the reaction carrier. Amberlite IR-120 was used as the solid heterogeneous catalyst. The catalyst loading effect, the reactant ratios, the reaction temperature (40-70 °C), and the influence of microwave irradiation on epoxidation and ring opening were studied. The application of microwave irradiation resulted in an improvement of the epoxidation rate in the absence of the catalyst. Lower product yields were obtained for the epoxidation of DTO than for TOFA because of the higher viscosity and high content of rosin acids which presumably promoted ring opening reactions. At higher temperatures, the selectivity to oxirane decayed due to ring opening. Titration analysis and NMR analysis confirmed that microwave irradiation induces the ring opening reactions for TOFA epoxidation, and it accelerates this process for DTO. The rapid nature of the microwave heating might have unchained a series of ring opening reactions between neighboring oxirane groups and with the nucleophilic agents in the reaction mixture.

Original languageEnglish
Pages (from-to)10397-10406
Number of pages10
JournalIndustrial and Engineering Chemistry Research
Volume59
Issue number22
DOIs
Publication statusPublished - 12 May 2020
MoE publication typeA1 Journal article-refereed

Keywords

  • epoxidation
  • vegetable oil
  • tall oil
  • Microwave irradiation

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