New developments in the fatty acid industry in America

Sonntag, Norman O. V.

doi:10.1007/bf02678774

Cited by 42 publications

(19 citation statements)

References 12 publications

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“…LG, particularly 1,3-DAG, can be synthesized from oils and fats via chemical glycerolysis using alkaline catalysts [11]. But these methods employ temperatures above 200 7C and are characterized by low selectivities and yields.…”

Section: Introductionmentioning

confidence: 99%

Optimization of the synthesis of lower glycerides rich in unsaturated fatty acid residues obtained via enzymatic ethanolysis of sesame oil

Criado

Otero

2010

Euro J Lipid Sci & Tech

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The lipases Novozym 435, Lipozyme TL IM and Lipozyme RM IM were employed in the production of lower acylglycerols (LG), i.e. mono-(MAG) and diacylglycerols (DAG), rich in unsaturated fatty acids from sesame oil in batch reactors. The effect of the molar ratio of ethanol to fatty acids on the reusability of these immobilized lipases was studied in detail. The effects of pretreatment on lipase activity for ethanolysis were investigated. Glycerol had a strong product inhibition effect on the ethanolysis reaction, and a relatively large excess of ethanol was necessary to remove the glycerol adsorbed on these biocatalysts. The enzymatic activity was drastically reduced by addition of water to the reaction medium. The presence of organic solvents (hexane and acetone) did not favor the production of LG. For the Novozym 435-catalyzed reaction, optimum conditions were a molar ratio of ethanol to fatty acid residues of 5 : 1, 15 wt-% lipase and 50 7C. For Lipozyme TL IM, the optimum conditions were a molar ratio of ethanol to fatty acid residues of 5 : 1, 20 wt-% biocatalyst, and 30 7C. Novozym 435 and Lipozyme TL IM produced LG with molar ratios of unsaturated to saturated fatty acids of 20.4 in 1 h and 25.3 in 5 h, respectively. In the original oil, this ratio was 5. For trials conducted under optimum conditions, the products from the Novozym 435 trials contained 21.8 wt-% triacylglycerols (TAG), 24 wt-% DAG and 54.2 wt-% MAG. The products of the Lipozyme TL IM trials consisted of 12.9 wt-% DAG and 87.1 wt-% MAG. No TAG species were detected.

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Section: Introductionmentioning

confidence: 99%

Optimization of the synthesis of lower glycerides rich in unsaturated fatty acid residues obtained via enzymatic ethanolysis of sesame oil

Criado

Otero

2010

Euro J Lipid Sci & Tech

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“…1,3-DAG can be synthesized chemically from fats and oils using glycerol via a chemical glycerolysis reaction at temperatures in excess of 200°C using an alkaline catalyst (9). However, the yield and purity are low in this method, making it unsuitable for industrial production.…”

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confidence: 99%

Optimization of reaction conditions for the production of DAG using immobilized 1,3‐regiospecific lipase lipozyme RM IM

Watanabe

Shimizu

Sugiura

et al. 2003

J Americ Oil Chem Soc

158

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Oils with a high DAG (1,3-DAG) content have attracted considerable attention as a healthful food oil component. In this study, we report on the synthesis of 1,3-DAG from a mixture of FA, constituted largely of oleic and linoleic acids, using an immobilized 1,3-regioselective lipase from Rhizomucor miehei in a solvent-free system. The kinetics of 1,3-DAG production from FA and glycerol were investigated on the basis of a simplified model, taking into consideration the acyl migration reaction, the removal of water, and glycerol dissolution in the oil phase in addition to the esterification reactions. Both the yield of 1,3-DAG and the purity of DAG were evaluated under a variety of experimental conditions, including reaction temperature, pressure, and amount of enzyme present. When either the reaction temperature or the amount of enzyme used was increased, the 1,3-DAG production rate increased, but yield remained relatively constant. The 1,3-DAG yield as well as the purity of DAG gradually decreased because of the enhancement of acyl migration at later stages of the reaction after the 1,3-DAG concentration reached a maximum. Vacuum was important for attaining high yields of 1,3-DAG. Under conditions of a high vacuum (1 mm Hg) at 50°C, 1.09 M 1,3-DAG was produced from 1.29 M glycerol and 2.59 M FA in an 84% yield and in 90% purity.Rate constants k 1 = 7.50 × 10 −4 (L/mol/s) k 3 = 2.91 × 10 −4 (L/mol/s) k 5 = 7.85 × 10 −6 (1/s) k 7 = 1.84 × 10 −3 (L/mol/s) k 9 = 3.59 × 10 −4 (1/s) k 10 = 1.20 × 10 −2 (1/s)

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“…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.…”

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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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New developments in the fatty acid industry in America

Cited by 42 publications

References 12 publications

Optimization of the synthesis of lower glycerides rich in unsaturated fatty acid residues obtained via enzymatic ethanolysis of sesame oil

Optimization of the synthesis of lower glycerides rich in unsaturated fatty acid residues obtained via enzymatic ethanolysis of sesame oil

Optimization of reaction conditions for the production of DAG using immobilized 1,3‐regiospecific lipase lipozyme RM IM

Synthesis of MAG of CLA with Penicillium camembertii lipase

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