- MANUFACTURING METHOD OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE, AND MANUFACTURING DEVICE OF MIDDLE CHAIN ALIPHATIC ACID TRIGLYCERIDE
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PROBLEM TO BE SOLVED: To provide a method capable of manufacturing a middle chain aliphatic acid triglyceride having good color tone and excellent stability, and a manufacturing device using the method. SOLUTION: There is disclosed a manufacturing method of middle chain aliphatic acid triglyceride and a manufacturing device of middle chain aliphatic acid triglyceride. The manufacturing method includes (a) a process for supplying a reaction system containing middle chain aliphatic acid and glycerin to an esterification reaction to obtain a reaction product containing the middle chain aliphatic acid triglyceride, (b) a process for removing unreacted middle chain aliphatic acid from the reaction product to obtain a reacted de-aliphatic acid product, and (c) a process for distilling the reacted de-aliphatic acid product using a thin film distillation machine to obtain a distilled product. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0078-0143; 0153-0161
(2019/08/12)
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- Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in an organic solvent system
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In this work, the esterification of glycerol with capric acid catalyzed by an immobilized form of a 1,3-positionally selective lipase (Rhizomucor miehei) showed to be effective for the synthesis of 1,3-dicaprin in n-heptane as the reaction medium. The effects of the reaction parameters were studied using an experimental factorial design of three factors and three levels with two central points. The selected experimental variables were amount of glycerol adsorbed on silica gel (G), biocatalyst load (E) and reaction temperature (T), and the response variables were total conversion of capric acid, acylglycerol fractions, selectivity and yield of dicaprin, and acyl migration reaction. The range of each parameter was selected as follows: G = 50-250 mg, E = 20-40 mg and T = 40-60 C. At optimum conditions 73% capric acid conversion was achieved, with 76% dicaprin selectivity, and selectivity to the specific 1,3-dicaprin of 70% of total products. An adequate selection of the reaction conditions is necessary not only to maximize the conversion of capric acid, but also to minimize the acyl migration reaction and the generation of undesired products. Evidence of kinetically controlled enzymatic acyl migration from sn-3/sn-1 to sn-2 is presented.
- Sanchez, Daniel Alberto,Tonetto, Gabriela Marta,Ferreira, Maria Lujan
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- Separation of acylglycerides obtained by enzymatic esterification using solvent extraction
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New avenues to add value to glycerol are currently being explored. One of them is the synthesis of structured lipids through glycerol esterification. In this work we have analyzed the recovery and purification of dicaprin obtained by esterification of glycerol with capric acid (C) in heptane, mediated by Lipozyme RM IM. This is an intermediate step to obtain lipids MLM. In the first stage, the diglyceride synthesis MGM (being G a central HC-OH) was carried out. When M = C, the diglyceride is CGC. Recovery of the diglyceride CGC is required to carry out the esterification of the sn-2 position with palmitic acid (P), thus obtaining the triglyceride CPC. Different solvents were evaluated using Ecofac 1.0 (a molecular design software solvent) through a theoretical approach to explore the best solvents for the acylglycerides separation. Then, the performance of the selected solvents to separate dicaprin from mono and tricaprin was experimentally studied in a liquid-liquid extraction process. Previously, the remaining fatty acid had been neutralized. With liquid-liquid extraction in three simple steps, using ethanol/water, 94 % of the dicaprin obtained by enzymatic esterification was recovered with a purity of 89 % (wt%). It was also possible to obtain dicaprin with a purity of 97 % but with a yield of 56 %.
- Sanchez, Daniel Alberto,Tonetto, Gabriela Marta,Ferreira, Maria Lujan
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p. 261 - 270
(2014/03/21)
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- METHOD FOR THE PREPARATION OF TRIGLYCERIDES OF MEDIUM-CHAIN LENGTH FATTY ACIDS
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A method is disclosed for the preparation of glycerol esters (triglycerides) of medium-chain length monocarboxylic fatty acids which consists of the reaction of the precursor free fatty acid and glycerol in the presence of a catalyst under partial vacuum. The process preferably uses a metal catalyst such as an oxide or a chloride of tungsten, molybdenum, calcium, zinc, chromium or magnesium. The method of the invention allows the preparation in high yield and high purity (>99.5%) of the final triglyceride. The present method allows the formation of triglycerides without solvent. Are also contemplated, the triglyceride obtained by the method, and the pharmaceutical composition containing the triglyceride as an excipient or as an active ingredient.
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Paragraph 0040
(2013/09/12)
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- TREATMENT OF NEURODEGENERATIVE CONDITIONS
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A method is provided for treating a patient in need of therapy for a neurodegenerative disease comprising administering to that patient a therapeutically effective dose of a lipid glyceride comprising a glycerol moiety and a fatty acid moiety, the fatty acid moiety being selected from the group consisting of γ-linolenic acid, dihomo-γ-linolenic acid and arachidonic acid characterised in that the selected fatty acid moiety is attached to the glycerol moiety at its sn-2 position. Preferably the method is that wherein the lipid is administered for a duration and at a dose sufficient to maintain or elevate TGF-β1 levels in the patient to therapeutic levels.
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Page/Page column 26-27
(2008/06/13)
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- Method for carrying out reactions characterized by an equilibrium
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The invention relates to a process for conducting a chemical reaction characterized by an equilibrium in a reaction system designed as a loop reactor, said loop reactor comprising a reactor vessel (1), at least one loop connected to said reactor vessel (1) each by means of an outlet and an inlet, said loop comprising means (3) for pumping over a fluid reaction material, at least one he exchanger (4), optionally means (5) for feeding said reaction material into Me reactor vessel (1) and a separate gas loop (8) which is connected to the gas space of the reactor vessel (1) above the reaction mixture and has separate means for feeding a gas into the gas loop (8), for withdrawing gas from the gas loop (8) and/or for treating said gas circulating in the gas loop (8), said process comprising the steps of circulating and/or treating said gas in said gas loop (8), feeding said gas into the reactor vessel (1) for influencing the equilibrium of a reaction conducted in said reactor vessel (1) and being characterized by the equilibrium and, after influencing said equilibrium reaction conducted in said reactor vessel (1), exhausting said gas from said reactor vessel (1) into the gas loop (8).
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Page column 12
(2008/06/13)
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- Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
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1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.
- Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo
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p. 839 - 843
(2007/10/03)
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- Glyceride synthesis in a solvent-free system
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Synthesis of partial glycerides in a solvent-free system has been investigated with various acyl donors and glycerol as substrates and a 1,3-specific immobilized lipase to catalyze the reaction. Capric acid was the most efficient acyl donor, compared with ethyl caprate and tricaprin. However, to obtain a high yield of dicaprin and a low amount of tricaprin, ethyl caprate was the acyl donor of choice. The composition of the product mixture was determined by the ratio of ethyl caprate to glycerol; a molar ratio of 3:1 was optimum for dicaprin synthesis. The water content in glycerol did not influence the final yield of dicaprin, but initial production of capric acid increased with increasing water content. The reaction was found to be controlled entirely by external mass transfer. The yield of diglyceride could be increased from 70 to 90% by lowering the reaction temperature, so that the diglyceride precipitated during the reaction.
- Fureby,Adlercreutz,Mattiasson
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p. 1489 - 1495
(2007/10/03)
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- Synthesis of medium-chain glycerides by lipase in organic solvent
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Using commercial lipases from various microbial origins, medium-chain glycerides, such as mono-, di-, and tri-caprin, were synthesized in isooctane from glycerol and capric acid. The enzyme reaction was performed with 0.35 M capric acid, 0.025 M glycerol, and 0.46 g silica gel to remove water in 5 mL of isooctane with 30 mg lyophilized lipase. Of the 21 kinds of lipases, 11 showed good synthetic activities. Lipases from Pseudomonas aeruginosa (Lipase PS), Rhizomucor miehei lipase and Chromobacterium viscosum lipase (Lipase CV) showed high activities for the production of tricaprin, while lipase OF-360 (from Candida rugosa) and lipase D (Rhizopus delemar) were good for dicaprin production. Lipases CC and MY from C. rugosa (C. cylindracea) also showed high activities for dicaprin and tricaprin. Some lipases, especially lipase PS, had high thermal stability over 60°C. The optimal lyophilization pH to dehydrate the lipase coincides with the optimal buffer solution pH for hydrolysis.
- Kwon, Dae Young,Song, Hyo Nam,Yoon, Suk Hoo
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p. 1521 - 1525
(2007/10/03)
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- 1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols
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The 1H-NMR spectroscopic properties of 15 synthetic homologous saturated triacylglycerols of type AAA and 16 mixed saturated triacylglycerols of type ABA and AAB have been studied. Triacylglycerols containing short-chain fatty acids (2:0-6:0) are readily identified. Triacylglycerols containing medium- and long-chain fatty acid components are not differentiated. From the analysis of 19 acetylenic triacylglycerols of type AAA, ABA and AAB (containing positional isomers of acetylenic fatty acids), it is only possible to characterize triacylglycerols with acyl groups containing the acetylenic bond at the Δ2-Δ5 position. 1H-NMR analysis could not confirm the positions (α- or β-acyl) of the acetylenic acids in mixed triacylglycerols. In the study of 22 ethylenic triacylglycerols of type AAA containing positional isomers of (Z)- or (E)-ethylenic acids, molecules containing an ethylenic bond in the Δ2 position of the acyl chains were readily characterized, as the ethylenic protons in the α- and β-acyl chains were fully resolved. Triacylglycerols containing an unsaturated center at the position were characterized by the shifts of the 2-H protons. The spectra of the remaining triacylglycerol molecules were very similar and the position of the ethylenic system could not be determined by this technique.
- Lie Ken Jie, Marcel S.F.,Lam
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p. 155 - 171
(2007/10/03)
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