Epoxidation Kinetics of High-Linolenic Triglyceride Catalyzed by Solid Acidic-Ion Exchange Resin

Kousaalya, Adhimoolam Bakthavachalam; Beyene, Shiferaw D.; Ayalew, Beshah; Pilla, Srikanth

doi:10.1038/s41598-019-45458-8

Cited by 12 publications

(8 citation statements)

References 33 publications

(55 reference statements)

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“…This is in good agreement with results regarding the curing of epoxide/anhydride systems described in literature 40 . Epoxide groups near the triglyceride center of ELSO are less reactive, due to a steric hindrance, and may remain unreacted 41 . As a result, increasing the MTHPA concentration, i.e.…”

Section: Resultssupporting

confidence: 92%

“…40 Epoxide groups near the triglyceride center of ELSO are less reactive, due to a steric hindrance, and may remain unreacted. 41 As a result, increasing the Figure 5(a) displays the curing enthalpy of the ELSO/TETA +2EI formulations prepared. The resin formulated with the calculated molar ratio shows the lowest curing enthalpy (i.e.…”

Section: Thermo-mechanical Propertiesmentioning

confidence: 99%

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Curing of epoxidized linseed oil: Investigation of the curing reaction with different hardener types

Todorovic

Resch‐Fauster

Mahendran

et al. 2020

J of Applied Polymer Sci

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The effect of the hardener type and amount on the curing reaction and the resulting thermal and mechanical performance characteristics of epoxidized linseed oil are studied in detail. The analysis of the curing mechanism reveals that due to steric hindrance, side reactions and/or fast gelation, the optimal mixing ratio of bio‐based epoxy resins and hardeners has to be determined experimentally and cannot be calculated. The investigated thermosets exhibit a glass transition temperature of 12, 54, and 145°C after curing. The overall mechanical performance of the resulting resin ranges from soft and flexible to stiff and rigid, depending on the hardener type applied, which can be utilized in the formation of epoxy composites and coatings.

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Section: Resultssupporting

confidence: 92%

Section: Thermo-mechanical Propertiesmentioning

confidence: 99%

Curing of epoxidized linseed oil: Investigation of the curing reaction with different hardener types

Todorovic

Resch‐Fauster

Mahendran

et al. 2020

J of Applied Polymer Sci

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“…Chemical groups at the 15th position are not affected by steric and electronic effects of the glycerol center that highly affected the closer groups (at the 9th and 12th positions). The opening of the epoxy group at the 15th position can cause steric hindrance affecting the epoxidation of the rest of the double bonds but also preventing any interaction between organic acid and the epoxy groups, thus preventing their cleavage [29]. TOFA and TOFAME do not contain glycerol center, which could interact sterically and electrically with chemical groups at the 9th, 12th and 15th positions.…”

Section: Resultsmentioning

confidence: 99%

Epoxidation of Tall Oil Fatty Acids and Tall Oil Fatty Acids Methyl Esters Using the SpinChem® Rotating Bed Reactor

et al. 2022

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Tall oil fatty acids are a second-generation bio-based feedstock finding application in the synthesis of polyurethane materials. The study reported tall oil fatty acids and their methyl esters epoxidation in a rotating packed bed reactor. The chemical structure of the synthesized epoxidized tall oil fatty acids and epoxidized tall oil fatty acids methyl ester were studied by Fourier-transform infrared spectroscopy. Average molecular weight and dispersity were determined from gel permeation chromatography data. The feasibility of multiple uses of the Amberlite® IRC120 H ion exchange resin as a catalyst was investigated. Gel permeation chromatography chromatograms of epoxidized tall oil fatty acids clearly demonstrated the formation of oligomers during the epoxidation reaction. The results showed that methylation of tall oil fatty acids allows obtaining an epoxidized product with higher relative conversion to oxirane and much smaller viscosity than neat tall oil fatty acids. Epoxidation in a rotating packed bed reactor simplified the process of separating the catalyst from the reaction mixture. The Amberlite® IRC120 H catalyst exhibited good stability in the tall oil fatty acids epoxidation reaction. Graphical Abstract

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“…Ergo, not all the double bonds can be treated in the same way. This explains the fact that the TOFA mixture behaves differently from oleic acid because linolenic acid is present in the TOFA mixture.…”

Section: Resultsmentioning

confidence: 99%

Epoxidation of Tall Oil Catalyzed by an Ion Exchange Resin under Conventional Heating and Microwave Irradiation

Aguilera

Rahkila

Hemming

et al. 2020

Ind. Eng. Chem. Res.

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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.

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Epoxidation Kinetics of High-Linolenic Triglyceride Catalyzed by Solid Acidic-Ion Exchange Resin

Cited by 12 publications

References 33 publications

Curing of epoxidized linseed oil: Investigation of the curing reaction with different hardener types

Curing of epoxidized linseed oil: Investigation of the curing reaction with different hardener types

Epoxidation of Tall Oil Fatty Acids and Tall Oil Fatty Acids Methyl Esters Using the SpinChem® Rotating Bed Reactor

Epoxidation of Tall Oil Catalyzed by an Ion Exchange Resin under Conventional Heating and Microwave Irradiation

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