Synthesis of monoglycerides by glycerolysis of rapeseed oil using immobilized lipase

Elfman‐Börjesson, Inger; Härröd, Magnus

doi:10.1007/s11746-999-0162-8

Cited by 50 publications

(36 citation statements)

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“…But the process cannot be applied to synthesize MAG of unstable FA. Hence, many research groups have engaged in the synthesis of MAG through lipasecatalyzed reactions (hydrolysis, esterification, glycerolysis, and ethanolysis) (3)(4)(5)(6)(7)(8). These reactions were, however, conducted in organic solvent systems, which are not suitable for industrial production of MAG esterified with functional FA.…”

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confidence: 99%

Synthesis of MAG of CLA with Penicillium camembertii lipase

Watanabe

Shimada

Yamauchi-Sato³

et al. 2002

J Americ Oil Chem Soc

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CLA has various physiological activities, and a FFA mixture containing almost equal amounts of cis-9,trans-11 and trans-10,cis-12 CLA (named FFA-CLA) has been commercialized. We attempted to produce MAG of CLA by a two-step successive reaction. The first step was esterification of FFA-CLA with glycerol. A mixture of FFA-CLA/glycerol (1:5, mol/mol), 2 wt% water, and 200 units/g of Penicillium camembertii monoand diacylglycerol lipase was agitated at 30°C to form a homogeneous emulsion. The esterification degree reached 84% after 10 h. To further increase the degree, the reaction was continued with dehydration at 5 mm Hg. The esterification degree reached 95% after 24 h (34 h in total), and the reaction mixture contained 50 wt% MAG and 44 wt% DAG. The second step was glycerolysis of the resulting DAG. The reaction mixture in the first-step esterification was transferred from the reactor to a beaker and was solidified by vigorous agitation on ice. When the solidified mixture was allowed to stand at 5°C for 15 d, glycerolysis of DAG proceeded successfully, and MAG content in the reaction mixture increased to 88.6 wt%. Hydrolysis of the acylglycerols was not observed during the second reaction. FA composition in the synthesized MAG was completely the same as that in the original FFA-CLA, showing that Penicillium lipase does not have selectivity toward FA in the FFA-CLA preparation.Paper no. J10248 in JAOCS 79, 891-896 (September 2002).KEY WORDS: CLA, esterification, glycerolysis, MAG, monoand diacylglycerol lipase, Penicillium camembertii.MAG are very good emulsifiers and are widely used as food additives. MAG are produced industrially by chemical alcoholysis of oils and fats with two molar equivalents of glycerol in the presence of metal catalysts at high temperatures of 210-240°C (1,2). But the process cannot be applied to synthesize MAG of unstable FA. Hence, many research groups have engaged in the synthesis of MAG through lipasecatalyzed reactions (hydrolysis, esterification, glycerolysis, and ethanolysis) (3-8). These reactions were, however, conducted in organic solvent systems, which are not suitable for industrial production of MAG esterified with functional FA. Meanwhile, several organic solvent-free systems also have been reported: (i) glycerolysis with Pseudomonas lipase (9,10); (ii) ethanolysis of TAG with immobilized Candida antarctica lipase (11); and (iii) esterification of FFA with glycerol using Penicillium camembertii mono-and diacylglycerol lipase (referred to as Penicillium lipase) (12). CLA is produced by alkali conjugation of safflower or sunflower oil in propylene glycol or ethylene glycol. The first product is a FFA mixture containing almost equal amounts of cis-9,trans-11 (c9,t11)-CLA and trans-10,cis-12 (t10,c12)-CLA, and the acylglycerols (main component, TAG) esterified with the FFA are also commercially available. The FFA mixture containing CLA isomers has various physiological activities that have been demonstrated in animal models, such as reduction of the incidence of cancer (13-15), d...

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confidence: 99%

Synthesis of MAG of CLA with Penicillium camembertii lipase

Watanabe

Shimada

Yamauchi-Sato³

et al. 2002

J Americ Oil Chem Soc

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“…Following this sharp decrease in FFA concentration, there is a slow rate of decrease up to an FFA concentration of 21% at 8 h. In earlier studies [11,13], the hydrolysis and synthesis reactions in a similar system were followed for 72 h at 34 8C. It has been observed that the change in the compositions reached almost equilibrium within the first 10 h. However, it has been reported again in similar systems by using commercial immobilized lipases such as Novozym 435 that the equilibrium level is reached in a shorter time than 2 h [12]. The time course to reach equilibrium is in agreement with these studies.…”

Section: Resultsmentioning

confidence: 99%

“…The potential use of vegetable oils as a substrate for the production of addedvalue compounds such as monoglyceride (MG) and diglyceride (DG) is an attractive way to valorize the olive oil industry [4]. Enzymatic esterification has been investigated for the production of MG and/or DG by several authors [11,12].…”

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Change in glyceride composition of olive pomace oil during enzymatic esterification

Göğüş

Fadı́loğlu

Ciftci

2004

Nahrung

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Enzymatic esterification of free fatty acids of olive pomace oil with glycerol was investigated. The esterification reaction was carried out in the absence and presence of glycerol (glycerol to free fatty acids (FFA) molar ratio of 1/3 and 1/6). In the absence of glycerol, the FFA concentration decreased from 32 to 21% while the triglyceride concentration increased from 33 to 40% after of 8 h of reaction time. The most significant decrease in FFAs and increase in triglycerides was observed at the limiting concentration of glycerol (glycerol to FFA molar ratio of 1/3). The FFA concentration decreased to 2.5% and the triglyceride concentration increased up to 78%. The change in both FFA and triglyceride concentrations was found to be statistically significant (P < 0.05).

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“…Several attempts to produce monoglycerides through the use of lipases, also immobilized, have been reported [16][17][18][19][20]. However, the yield in monoglycerides never exceeded 40 %, thus requiring a molecular distillation process.…”

Section: Resultsmentioning

confidence: 99%

The use of rice bran oil within a biorefinery concept

Zaccheria

Mariani

Ravasio

2015

Chem. Biol. Technol. Agric.

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Background: A waste of the rice production chain, namely bran, can be used to produce an oil with a very high content in free fatty acids (FFA). Due to its very high acidity, this material cannot be used neither to feed power generators nor as raw material for oleochemicals synthesis, and therefore it is not even extracted. Results: Rice bran oil with a content of 84 % in free fatty acids can be converted into a mixture of triglycerides or into useful oleochemicals such as monoglycerides, widely used as emulsifiers in food. Monoglycerides were obtained carrying out a one step esterification + transesterification reaction over an amorphous solid acid. Yields are higher than those obtained by enzymatic transesterification of oil and competitive with the esterification of free fatty acids involving the use of homogeneous acids generating significant amounts of wastewaters. On the other hand, esterification with higher amount of glycerol, a low value by-product of the biodiesel industry, gave an oil with low acidity suitable to feed power generators. Conclusions:The use of solid acid catalysts is a valuable tool for the valorization of rice bran oil. The chance to produce a low acidity oil or monoglycerides in one step from RBO may add value to the whole rice productive chain while setting the stage for the design of biorefineries based on the use of agro-industrial residues.

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Synthesis of monoglycerides by glycerolysis of rapeseed oil using immobilized lipase

Cited by 50 publications

References 23 publications

Synthesis of MAG of CLA with Penicillium camembertii lipase

Synthesis of MAG of CLA with Penicillium camembertii lipase

Change in glyceride composition of olive pomace oil during enzymatic esterification

The use of rice bran oil within a biorefinery concept

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