Epoxidation of Linseed Oil by Performic Acid Produced In Situ

Abstract

Linseed oil is characterized by an elevated concentration of highly unsaturated fatty acids such as linolenic and linoleic acids. This work has the objective to evaluate the effect of the high unsaturation of linseed oil on the reactivity and selectivity of the epoxidation reaction. For this purpose, different kinetic experiments of linseed oil epoxidation with performic acid, produced in situ, and phosphoric acid as catalyst, have been performed and interpreted with a biphasic kinetic model previously tested on soybean oil epoxidation. This model considers the contribution of the main reactions involved in each phase, including the side reactions such as performic acid decomposition and ring opening reactions. The experiments made have been simulated, with the mentioned kinetic model, after the evaluation by mathematical regression of the kinetic and thermodynamic parameters of the model. Then, the obtained results have been compared with those described in the literature for soybean seed oil, considering, in particular, the effect of the different unsaturated fatty acids composition on activity and selectivity.

Selective Oxidation of Glucose using Hydrogen Peroxide as an Oxidant: On the Structure Sensitivity of the Apparent Activation Energy

“…The strong S‐shape of concentration curve typically indicates an autocatalytic behaviour. A plausible explanation for such behaviour is related to formation of performic acid due to presence of formic acid and hydrogen peroxide in the reaction medium [27] . Subsequently performic acid can accelerate further C−C scission leading to the S‐shaped concentration curves.…”

“…A plausible explanation for such behaviour is related to formation of performic acid due to presence of formic acid and hydrogen peroxide in the reaction medium. [27] Subsequently performic acid can accelerate further CÀ C scission leading to the S-shaped concentration curves. However, this behaviour slows down with a decreasing hydrogen peroxide concentration, which is apparently related to slower performic acid formation.…”

Epoxidation of Methyl Esters as Valuable Biomolecules: Monitoring of Reaction

“…For ME_LO, the signal belonging to the valence vibrations of OH groups (maximum at 3417 cm −1 ) increased with increasing reaction time ( Figure 2 A). This indicates the subsequent hydrolysis of the epoxides to alcohols [ 31 ]. The hydrolysis corresponds with (i) almost zero EI, i.e., almost zero oxirane rings and (ii) a high kinematic viscosity (450 mm 2 /s) after 24 h of reaction.…”

Comparative Thermo-Mechanical Properties of Sustainable Epoxy Polymer Networks Derived from Linseed Oil

“…The higher unsaturation degree (about 6.3 double bonds per triglyceride molecule) offers numerous possibilities for chemical modification to synthesize more complex or more reactive macromolecules. Perhaps the most important and studied reaction at the VOs double bonds is the epoxidation because the oxirane ring gives countless possibilities to obtain high performance materials or it can be subjected to different reaction strategies to further modify the oil structure, obtaining more reactive functionalities grafted on the triglyceride backbone [ 10 ]. The epoxidation of LO is preferentially performed by in situ method, using peracetic or performic acids as oxidizing agents, the epoxy content being tailored through the control of the reaction parameters (reactants ratio, time) [ 10 , 11 ].…”

“…Perhaps the most important and studied reaction at the VOs double bonds is the epoxidation because the oxirane ring gives countless possibilities to obtain high performance materials or it can be subjected to different reaction strategies to further modify the oil structure, obtaining more reactive functionalities grafted on the triglyceride backbone [ 10 ]. The epoxidation of LO is preferentially performed by in situ method, using peracetic or performic acids as oxidizing agents, the epoxy content being tailored through the control of the reaction parameters (reactants ratio, time) [ 10 , 11 ]. Aside from all the associated advantages, ELO (like other epoxidized VOs), can lead to polymeric structures through different reaction strategies, but their thermal and mechanical features are not so competitive for industrial applications.…”