Esterification Kinetics of Glycerol with Fatty Acids in the Presence of Zinc Carboxylates:  Preparation of Modified Acylglycerol Emulsifiers

Macierzanka, Adam; Szeląg, Halina

doi:10.1021/ie040077m

Cited by 64 publications

(51 citation statements)

References 25 publications

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“…Investigations on the effectiveness of acylglycerol emulsifiers, modified with sodium and potassium soaps, showed the possibility of using such emulsifiers for the stabilization of O/W emulsions [20]. As presented elsewhere [21,22] the modification of the hydrophobic properties of acylglycerol emulsifiers may be realized by means of the controlled esterification of glycerol with fatty acids in the presence of zinc or magnesium soaps. In contrast to the use of alkali soaps, the synthesized products are very effective in the stabilization of W/O-type emulsions.…”

Section: Introductionmentioning

confidence: 93%

Effect of Alkyl Sulfate on the Phase Behavior of Microemulsions Stabilized with Monoacylglycerols

Szeląg

Szumała

2010

J Surfact & Detergents

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In this study the effect of an anionic surfactant (sodium dodecyl sulfate SDS) and oils (hydrocarbons: C12-C16) on the formation and phase behavior of the systems of oil/monoacylglycerols (MAG):SDS/propylene glycol/water has been investigated. The effects of the surfactant mixture on the phase behavior and the concentration of water or oil in the systems were studied at three temperatures (50, 55, 60°C). Electrical conductivity measurement, FT-IR spectroscopy and differential scanning calorimetry methods were applied to determine the structure and type of the microemulsions formed. The dimension of microemulsion droplets was characterized by dynamic light scattering. It has been stated that the concentration of SDS has a strong influence on the shape and extent of the microemulsion areas. Addition of an ionic surfactant to the mixture with MAG promotes an increase in the area of microemulsion formation in the phase diagrams, and these areas of the isotropic region change with the temperature. It was shown that the presence in the systems of a surfactant more hydrophilic than MAG caused an increase in water content in the microemulsions. It was found that, depending on temperature and concentration of the surfactant mixture, it was possible to obtain a W/O type microemulsion with a dispersed particles size distribution ranging from 20 to 50 nm and containing about 17-38% water in the system. Among different alkanes (from C12 to C16), hexadecane embedded microemulsions showed a maximum water solubilization capacity. Keywords Microemulsions Á Monoacylglycerols Á Sodium dodecyl sulfate Á FT-IR Á DSC Á DLS Abbreviations FTIR Fourier transform infrared MAG Monoacylglycerols ME Microemulsions MLS Multiple light scattering PG Propylene glycol (1,2-propanediol) SDS Sodium dodecyl sulfate

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Section: Introductionmentioning

confidence: 93%

Effect of Alkyl Sulfate on the Phase Behavior of Microemulsions Stabilized with Monoacylglycerols

Szeląg

Szumała

2010

J Surfact & Detergents

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“…3, 4, 5, 6). Literature reports that the HOAc:glycerol molar ratio is a key factor in these reactions [28,29]. However, data is scarce regarding glycerol esterification reactions catalysed by Lewis acids [30].…”

Section: Effects Of the Glycerol:hoac Molar Ratiomentioning

confidence: 99%

Novel Esterification of Glycerol Catalysed by Tin Chloride (II): A Recyclable and Less Corrosive Process for Production of Bio-Additives

2011

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In this work, a novel process based on use of a SnCl 2 Á2H 2 O catalyst which is less corrosive, inexpensive, and a water tolerant Lewis acid was employed for synthesis of fuel bio-additives from glycerol. High yields and selectivities were achieved for glycerol esterification with acetic acid under mild reaction conditions. The SnCl 2 catalyst showed to be as active as p-toluene sulfonic and sulfuric acid, catalysts commonly used in acid-catalysed esterification reactions. However, its use has significant advantages in comparison to these Brønsted acid catalysts, including lower reactor corrosion and unnecessary neutralization at the end reaction. The SnCl 2 catalyst can also be recovered and reused without loss of catalytic activity. Additionally, effects of reaction temperature, HOAc:glycerol molar ratio and catalyst concentration on both selectivity and yield of glycerol acetates were also investigated. The lower corrosiveness, facilitated handling, as well as potential for reuse without activity loss after simple recycle protocols are positive aspects of SnCl 2 catalysts.

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“…Macierzanka and Szelag [17] studied the esterification of glycerol in the presence of zinc carboxylates and found that this catalyst significantly influenced monoglyceride (MAG) conversion and its presence increased the glycerol-fatty acid interfacial area (increase of microemulsions formation). Di Serio and co-workers [18] described esterification reactions employing layered metal carboxylates or layered metal soaps (zinc acetate and stearate).…”

Section: Introductionmentioning

confidence: 99%

Esterification of fatty acids with ethanol over layered zinc laurate and zinc stearate – Kinetic modeling

Paiva

Sterchele

Corazza

et al. 2015

Fuel

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h i g h l i g h t sModeling of long chain FFA with ethanol was performed using EleyRideal approach. No diffusional limitations were found with zinc carboxylic salts. High hydrophobic behavior was observed with zinc laurate. Ethanolysis of FFA reached 92% and catalytic gain compared to blanks reached 40%. Structural changes in the catalyst were observed which exchange FFA with the medium. g r a p h i c a l a b s t r a c t a b s t r a c tThis work is focused on the esterification of fatty acids (commercial oleic mix) with zinc carboxylates (layered metal soap). About 25 experiments were performed, with and without catalyst, yielding a kinetic model based on the Eley-Rideal approach, able to predict fatty acid conversions under different conditions (molar ratio fatty acids/ethanol and temperature). An apparent first order reaction with respect to both reactants with no diffusion limitations was proposed. The activation energy of 80 kJ/mol was found. Fatty acid conversion up to 92% was reached under some conditions and the catalytic yields compared to the blank ones reached 40% in less than 90 min of reaction. This catalyst has shown a unique behavior among all other catalysts available for esterification, acting similarly to a homogeneous catalyst during the reaction but being recovered like a heterogenous catalyst at the end of the process.

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Esterification Kinetics of Glycerol with Fatty Acids in the Presence of Zinc Carboxylates: Preparation of Modified Acylglycerol Emulsifiers

Cited by 64 publications

References 25 publications

Effect of Alkyl Sulfate on the Phase Behavior of Microemulsions Stabilized with Monoacylglycerols

Effect of Alkyl Sulfate on the Phase Behavior of Microemulsions Stabilized with Monoacylglycerols

Novel Esterification of Glycerol Catalysed by Tin Chloride (II): A Recyclable and Less Corrosive Process for Production of Bio-Additives

Esterification of fatty acids with ethanol over layered zinc laurate and zinc stearate – Kinetic modeling

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