Preparation and some properties of tung oil monoglycerides

McKinney, R. S.; Goldblatt, L. A.

doi:10.1007/bf02638758

Cited by 10 publications

(4 citation statements)

References 13 publications

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“…Significant improvement was observed when the catalyst concentration was increased to 2%, the reaction temperature was raised to 80°C, and the reaction was conducted in the presence of five parts of pyridine. Under these conditions, the crude tung oil MG were found to contain 78.2% MAG after a 30-min reaction time (8).…”

Section: Resultsmentioning

confidence: 97%

“…Täufel et al (7) reported that the glycerolysis of soybean, peanut, sunflower seed, and rapeseed oils in the presence of pyridine using catalysts such as sodium methoxide, sodium ethoxide, and sodium carbonate could achieve MAG yields of up to 72% in reactions conducted between 100 and 110°C for 15 min. The glycerolysis of tung oil in the presence of 1% sodium methoxide and an excess of glycerol at 30% has been reported to yield a product containing 32.2% MAG after a 2-h reaction at 65°C (8). Significant improvement was observed when the catalyst concentration was increased to 2%, the reaction temperature was raised to 80°C, and the reaction was conducted in the presence of five parts of pyridine.…”

Section: Resultsmentioning

confidence: 99%

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Rapid synthesis of palm‐based monoacylglycerols

Cheng

Choo

et al. 2005

J Americ Oil Chem Soc

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Rapid synthesis of high-purity MAG from refined, bleached, and deodorized palm stearin (RBDPS) via chemical glycerolysis in the presence of pyridine was developed to obviate the conventional molecular distillation in the production of pure MAG. The optimal reaction for the sodium methoxide-catalyzed glycerolyis of RBDPS was recorded at 110°C using a 3 wt% catalyst concentration based on the weight of RBDPS, with an RBDPS/glycerol ratio of 1:2 and an RBDPS/pyridine ratio of 1:4. High yields of over 99% were achieved rapidly in 15 min, and increases in DAG and FFA were observed after a prolonged reaction time.Paper no. J11044 in JAOCS 82, 791-795 (November 2005). KEY WORDS:Glycerolysis; monoacylglycerols; pyridine; refined, bleached, and deodorized palm stearin.Partial glycerides are synthesized commercially on an industrial scale for application as emulsifying agents in a wide range of foods. MAG, with emulsifying properties superior to DAG, account for over 70% of the total world consumption as food emulsifiers (1). The chain length of the alkyl group in MAG in various formulations will determine the application, e.g., as emulsifiers, texturing agents, lubricants, or plasticizers in pharmaceuticals, cosmetics, or textiles (2). However, the applications of MAG are still mainly in the food industry because of their excellent self-emulsifying and surface-active properties. MAG are usually produced commercially by the glycerolysis of natural oils and fats. The reaction involves a reversible equilibrium; thus, the reaction product will always contain a mixture of MAG, DAG, and TAG. Generally, a reaction temperature above 220°C and an inorganic catalyst are needed (3). In addition to glycerolyis starting from oils and fats, the glycerolyis of methyl esters has also been investigated by researchers. Jeromin et al. (4) reported the production of MAG via the glycerolysis of methyl esters derived from animal and vegetable fats and oils. The reaction was carried out using methyl esters at a concentration ratio of MAG and DAG that lay between 3 and 10 in the presence of an alkaline catalyst. The reaction temperatures were slightly lower than those described earlier, i.e., between 130 and 160°C, but at a vacuum of 200 to 400 mbar. Both reactions yielded technical-grade MAG consisting of a glyceride mixture containing 40-60% MAG and DAG.Technical-grade MAG generally consists of a mixture of 40-48% MAG, 30-40% DAG, 5-10% TAG, 0.2-9% FA, and 4-8% glycerol (2). However, when used as emulsifiers, glycerides are required to contain at least 90% MAG. Hence, in the conventional production of such glycerides, it is necessary to subject the glyceride mixture to molecular distillation to enhance the content of MAG. The final yield in the conversion from TAG to MAG was reported to be about 58% (3).The production of MAG via chemical synthesis can be further improved by using a suitable solvent to increase the solubility of glycerol in the oil and subsequently enhance the glycerolysis reaction. Studies using various solvents to improve the...

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Rapid synthesis of palm‐based monoacylglycerols

Cheng

Choo

et al. 2005

J Americ Oil Chem Soc

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“…[70] The heat treatment additionally pre-polymerizes the oil molecules and hence leads to enhanced and faster crosslinking during the curing process. [70][71][72][73] Here, we focus on three drying oils differing in their molecular composition, degree of unsaturated bonds and hence their crosslinking abilities; namely tung oil (having a surface tension of γ = 33.1 mJ m −2 ), [74] linseed oil (γ = 31.3 mJ m −2 ), [74] and a mixture of linseed oil and colophony. The latter is well known to lower the surface energy of water [75] and increase the hydrophobicity of blends with polymers.…”

Section: Preparation Of the Coating System Based On Drying Oilsmentioning

confidence: 99%

Sustainable Repellent Coatings Based on Renewable Drying and Nondrying Oils

Dehm

Walter²,

Weichselgartner

et al. 2022

Adv Materials Inter

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Contamination of surfaces can cause loss of performance in a variety of applications. Bioinspired coatings based on the lotus or pitcher plants provide surface topographies that create superhydrophobic or slippery features with self‐cleaning properties. However, typical fabrication procedures often involve potentially toxic chemicals, perfluorinated compounds, nondegradable polymers, and energy‐intensive methods, with negative consequences for the environment. Here, a sustainable coating process based on renewable materials to prepare superhydrophobic and liquid‐infused coatings with minimal environmental impact is presented. A scalable spray coating protocol is used. Synthetic liquid and polymeric materials are substituted with natural drying oils, i.e., oils that react with ambient oxygen and cure to solid materials, as polymeric binder in which silica particles are partially embedded. The self‐cleaning characteristics against aqueous contaminations are investigated as a function of the drying oil used as binder. The assessment of the mechanical stability reveals the advantage of an underlying “primer layer” of the pure oil. Furthermore, it is demonstrated that oils from renewable sources can act as lubricants for the creation of slippery surfaces. The efficiency of such sustainable slippery coatings in reducing concrete adhesion points toward their applicability in real world scenarios.

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“…The immiscibility of the glycerol and TAG leads to mass transfer limitation, which is commonly considered to be the most significant reason for the low total conversion and yield of MAG. Different approaches have been investigated in lipase-catalysed glycerolysis processes, carried out in different reaction media such as organic solvents 24 and supercritical carbon dioxide 25 -29 or with aid of micro-emulsion technology. 30 Supercritical fluids as a green solvent have been studied for enhancing mass transfer, especially between the glycerol-layer and the TAG-layer, for this case in the past 10 years.…”

Section: Introductionmentioning

confidence: 99%

Sustainable utilization of crude glycerol from biodiesel production: catalyst free monoacyglycerols production

Liu

Yan

Jiang

2017

J. Chem. Technol. Biotechnol

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BACKGROUND The biodiesel by‐product, crude glycerol including lower alcohols, could be used as the feedstock for producing monoacyglycerols (MAGs), which are commonly used as non‐ionic surfactants and emulsifiers. In this work, lower alcohols (methanol, ethanol and isopropanol) in sub‐ and supercritical states were used as the solvents for MAG production. RESULTS Isopropanol is the best solvent for obtaining high monooleate (MOG) yield compared with methanol and ethanol. Moreover, the sub‐ and super‐critical isopropanol shows better performance than the normal NaOH catalyzed or non‐solvent process. The reaction loading of a batch reactor has a complicated effect on the yield. The maximum MOG yield can always be obtained at 60% loading. The square root modified quadratic model was utilized to analyze the relationship and to optimize reaction temperature (220–260 °C), reaction time (30–150 min), and isopropanol (0–4 mL). In the optimum condition (260 °C, 150 min, 4 mL of isopropanol), a high MOG yield of 67.8% can be obtained, well in agreement with the predicted value. CONCLUSION Isopropanol at sub‐ and super‐critical state greatly improved the mass transfer between the immiscible reactants (triglyceride and glycerol). Compared with some methods with chemical catalyst, the method without any catalyst obtained higher MOG yield. © 2016 Society of Chemical Industry

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Preparation and some properties of tung oil monoglycerides

Cited by 10 publications

References 13 publications

Rapid synthesis of palm‐based monoacylglycerols

Rapid synthesis of palm‐based monoacylglycerols

Sustainable Repellent Coatings Based on Renewable Drying and Nondrying Oils

Sustainable utilization of crude glycerol from biodiesel production: catalyst free monoacyglycerols production

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