Biphasic reaction of glycerol and oleic acid: Byproducts formation and phase transfer autocatalytic effect

Gomes, Mariana de S.; Santos, Mariana Rocha Dutra; Salviano, Adriana Barbosa; Mendonça, Fernanda G.; Menezes, Izadora R.S.; Jurisch, Marina; Rodrigues, Guilherme Dias; Augusti, Rodinei; Martins, Paulo Sodero; Lago, Rochel M.

doi:10.1016/j.cattod.2019.02.011

Cited by 6 publications

(3 citation statements)

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“…In our previously published review [8] on glycerolysis of oleic acid (OA), the FFA conversion rate is higher initially when the MO yield is also higher, irrespective of the reaction being catalyzed or non-catalyzed. The presence of MO dictating the conversion of OA in the glycerolysis reaction has been recently well established by the work of Gomes et al [9]. MO, an ester of OA, was found to act as a phase transfer agent, accelerating the reaction.…”

Section: Introductionmentioning

confidence: 92%

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Liquid‐Liquid Phase Equilibrium of Glycerolysis Precursors: Experimental and Modeling Study

Mamtani,

da Silveira,

Farid

et al. 2023

Chem Eng & Technol

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The mutual immiscibility of glycerol and free fatty acids limits glycerolysis, a reaction capable of upgrading waste‐derived oils. In the present work, the liquid‐liquid phase equilibrium data for the glycerol‐water‐oleic acid and glycerol‐monoolein‐oleic acid ternary systems were determined experimentally and compared with predictions of the UNIFAC‐LLE and COSMO‐SAC models. Monoolein was found to affect the glycerol solubility in oleic acid strongly. None of the models investigated adequately determined phase equilibria for the glycerol‐monoolein‐oleic acid system. COSMO‐SAC predictions showed the best trend for glycerol solubility in the fatty phase. For the glycerol‐water‐oleic acid system, UNIFAC‐LLE predictions were in good agreement with experimental data.

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Section: Introductionmentioning

confidence: 92%

“…MO, an ester of OA, was found to act as a phase transfer agent, accelerating the reaction. Given the evidence [9], it is intuitive that the glycerolysis biphasic system's reaction kinetics will be impacted by this changing phase behavior, and thus is worthwhile of an investigation.…”

Section: Introductionmentioning

confidence: 99%

Liquid‐Liquid Phase Equilibrium of Glycerolysis Precursors: Experimental and Modeling Study

Mamtani,

da Silveira,

Farid

et al. 2023

Chem Eng & Technol

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“…2a, c, and e), reaching 54.90 ± 3.32 g/100 g glycerol-free product at 40 °C, 59.31 ± 2.14 g/100 g at 50 °C, and 60.97 ± 0.15 g/100 g at 60 °C. This was possible because a higher reaction temperature increases both the rate of reaction and the mutual miscibility of reactants, leading to higher conversions and more products [45]. Also, maximum selectivity for both DG (S DG ) and PG (S PG ) occurred earlier but within a narrower period as the temperature was increased (Fig.…”

Section: Effect Of Temperature and Molar Ratio On Conversion Distribu...mentioning

confidence: 99%

Synthesizing Precursors for Functional Food Structured Lipids from Soybean Oil Deodorized Distillates

Agapay

Tran‐Nguyen

et al. 2020

Waste Biomass Valor

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A "green" scheme of synthesizing diglycerides as a means of valorizing an oil processing by-product, specifically soybean oil deodorized distillate (SODD), was established. Different glycerol dosing strategies were implemented in the solvent-free lipase catalyzed esterification of free fatty acids with glycerol within molar ratios of 2-4 and temperatures of 40-60 °C. The process responses were compared with non-dosed systems in this study and other similar processes reported in literature. Better 1,3-diglyceride selectivity at comparable yields were observed with glycerol dosed-systems over non-dosed systems. The presence of molecular sieves negatively affected 1,3-diglyceride selectivity, total diglyceride selectivity and yield. Selectivity of 0.91 ± 0.01 g diglycerides/g (mono + triglycerides), free fatty acid conversion of 57.87 ± 3.46%, and yield of 30.59 ± 1.26 g diglyceride/100 g raw material is obtained with SODD at 40 °C, overall free fatty acid to glycerol molar ratio of 2, 4 wt% Novozyme 435 and 48 h. The process scaled better than most solvent-based ones supported with hygroscopic sorbents in terms of reaction mass efficiency.

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Glycerol polymerization degree effect on the emulsifying properties of polyglycerol esters

Díaz-Lasprilla

Mercado

Ramirez-Caballero

2021

J of Applied Polymer Sci

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Polymeric emulsifiers based on glycerol and oleic acid were developed and their properties evaluated in palm oil and water solutions. Developed polymeric emulsifiers were polyglycerol-esters. Polymerization degree of polyglycerol-esters at different dosages (from 0.2 to 3% w/v) had a significant effect over emulsion stability, water surface tension, droplet size, and viscosity. Polyglycerol-ester with highest polymerization degree behaved more efficiently as emulsifier. A dosage of 0.5% w/v was required to maintain emulsion stability for a half-life period of 872 min (~14.5 h); which, is 5.6 and 3.6-fold longer stability than with the other two polyglycerol-esters developed. When dosage increased to 3% w/v, the emulsion stability also increased to 3792 min (~2.6 days). Nevertheless, surfactants with lower polymerization degree and molecular weight did not behave the same way. Emulsifier with highest polymerization degree reduced water surface tension by 70% and the mean particle diameter decreased when emulsifier polymerization degree increased. For the viscosity parameter, there were two interesting regions: for shear rates up to 1 s −1 the emulsion behaved as Non-Newtonian fluid type Shear-thinning; while, higher shear rates, the viscosity exhibited a Newtonian profile.

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Biphasic reaction of glycerol and oleic acid: Byproducts formation and phase transfer autocatalytic effect

Cited by 6 publications

References 50 publications

Liquid‐Liquid Phase Equilibrium of Glycerolysis Precursors: Experimental and Modeling Study

Liquid‐Liquid Phase Equilibrium of Glycerolysis Precursors: Experimental and Modeling Study

Synthesizing Precursors for Functional Food Structured Lipids from Soybean Oil Deodorized Distillates

Glycerol polymerization degree effect on the emulsifying properties of polyglycerol esters

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