Tall Oil Fatty Acid Epoxidation Using Homogenous and Heterogeneous Phase Catalysts

• DOI: 10.1007/s10924-020-01724-9
• Publication Date: 2020-04-09T17:02:43Z
• Authors: Arnis Abolins; Mikelis Kirpluks; Edgars Vanags; Anda Fridrihsone; Ugis Cabulis
• Keywords: Amberlite; Tall oil; Ion-exchange resin; Peracetic acid; Degree of unsaturation

Tall oil fatty acids were epoxidized by in-situ generation of peracetic acid in the presence of two different acidic catalysts, commonly used catalyst—sulfuric acid and ion exchange resin. The described epoxidation was carried out without the use of organic solvents to comply with the principles of Green chemistry. The epoxidation process was monitored by the change of the relative oxirane conversion and alkenic unsaturation. Furthermore, the changes in the chemical structure of the epoxidized tall oil fatty acids were investigated using FTIR spectroscopy. It was shown that ion exchange resin Amberlite IR-120 H catalyst was superior to sulfuric acid catalyst as it delivered fewer by-products from oxirane group opening reactions. The oxirane value reached up to 2.31 mmol/g of epoxy groups, which is 41.9% of theoretically possible oxirane oxygen yield, when tall oil was epoxidized using Amberlite IR-120 H. The reusability of ion exchange resin was also studied, the 6.2% decrease in relative oxirane conversion value was registered after Amberlite IR-120 H was reused up to 10 times.