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Method of preparing conjugated linoleic acid glyceride by utilizing immobilized lipase

A conjugated linoleic acid glyceride, conjugated linoleic acid glyceride technology, applied in the field of preparing conjugated linoleic acid glyceride, can solve the problems of long time, reduce product quality, easy residues, etc., to save cumbersome processes , The effect of reducing the reaction time and reducing the impurity content

Active Publication Date: 2014-06-11
INNOBIO CORP LTD
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  • Summary
  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem with this process is that the organic solvent is highly toxic and easy to remain in the product, and at the same time the organic solvent is highly volatile, resulting in high production costs
[0008] Patent CN200710030862.9 utilizes immobilized enzyme (Novozym435) in the presence of n-hexane to catalyze the esterification reaction of glycerol and ω-3 polyunsaturated fatty acid free fatty acid to prepare triglycerides. After 24 hours of reaction, the content of triglycerides is 1% of the glycerides. 31%, the reaction time of this process is relatively long, and the yield is relatively low
The problem with this process is that the whole process takes a long time, and it is easy to cause product oxidation, reduce product quality, and increase costs.
The problem with this process is that the organic solvent is highly toxic and easy to remain in the product, and at the same time the organic solvent is highly volatile, resulting in high production costs
The additives used will remain in the final product, and molecular sieves are used in the process, which is not easy to reuse and increases the reaction cost
In addition, the problem of this process is that the organic solvent is highly toxic and easy to remain in the product. At the same time, the volatility of the organic solvent is relatively high, resulting in high production costs.
The problem with this process is that the organic solvent is highly toxic and easy to remain in the product. At the same time, the organic solvent is highly volatile, resulting in high production costs.
However, it can be seen that the reaction time of the solvent-free system is relatively long, which is not conducive to industrial production.
[0013] The preparation of commercialized conjugated linoleic acid glycerides is mostly chemical method. The starting materials are conjugated linoleic acid ethyl ester and methyl ester. The preparation of conjugated linoleic acid ethyl ester and methyl ester is through safflower oil and The methyl linoleate product is obtained by transesterification of methanol, and then catalyzed and conjugated by a basic catalyst to obtain ethyl and methyl conjugated linoleate. The material contains partially saponified free fatty acids, which need to be deacidified to obtain Only materials with an acid value ≤ 1 can undergo transesterification, and the process is cumbersome, which affects product quality

Method used

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  • Method of preparing conjugated linoleic acid glyceride by utilizing immobilized lipase
  • Method of preparing conjugated linoleic acid glyceride by utilizing immobilized lipase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] (1) Fill 2.4g of immobilized lipase in the enzyme reaction column, and keep the temperature of the enzyme reaction column at 45°C;

[0060](2) Put methyl conjugated linoleate containing 1% free fatty acid and glycerol in a molar ratio of 3:1 into the material tank, and preheat to 65°C;

[0061] (3) Stir and mix the materials in step (2) evenly at a stirring speed of 100rpm / min. The uniformly mixed material liquid is pumped into the enzyme reaction column through a constant flow pump at a flow rate of 0.5ml / min. The reaction was continued for 35 hours, and the reaction product was collected. Molecular distillation was carried out at 175° C. and 20 Pa to remove excess methyl conjugated linoleate to obtain the final product.

[0062] The composition and content of the final product were determined by high performance liquid chromatography, and the results are shown in Table 1.

Embodiment 2

[0064] (1) Fill 2.4g of immobilized lipase in the enzyme reaction column, and keep the temperature of the enzyme reaction column at 45°C;

[0065] (2) Put the conjugated linoleic acid methyl ester and glycerin with 0% free fatty acid in a molar ratio of 3:1 into the material tank, let it stand, the reaction liquid is divided into two layers, and the upper layer is conjugated linoleic acid methyl ester , the lower layer is glycerol, and the reaction solution is preheated to 65°C;

[0066] (3) Pass the sample tube connected to the constant flow pump into the bottom end of the conjugated methyl linoleate material in the upper layer of the reaction solution, and pump it into the enzyme reaction column through the constant flow pump at a flow rate of 0.5ml / min. After the second time, feed the feed pipe to the bottom of the glycerin layer in the lower layer of the reaction solution, pump it into the enzyme reaction column through a constant flow pump, and the flow rate is 0.5ml / min,...

Embodiment 3

[0070] (1) Fill 2.4g of immobilized lipase in the enzyme reaction column, and keep the temperature of the enzyme reaction column at 50°C;

[0071] (2) Put the conjugated linoleic acid methyl ester containing 5% free fatty acid and glycerol in a molar ratio of 3.5:1 into the material tank, let it stand, the reaction liquid is divided into two layers, and the upper layer is conjugated linoleic acid methyl ester , the lower layer is glycerol, and the reaction solution is preheated to 65°C;

[0072] (3) Pass the sample tube connected to the constant flow pump into the bottom end of the conjugated methyl linoleate material in the upper layer of the reaction solution, and pump it into the enzyme reaction column through the constant flow pump at a flow rate of 0.5ml / min. After the second time, feed the feed pipe to the bottom of the glycerin layer in the lower layer of the reaction solution, pump it into the enzyme reaction column through a constant flow pump, and the flow rate is 0....

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Abstract

The invention provides a method of preparing conjugated linoleic acid glyceride by utilizing immobilized lipase. Conjugated linoleic acid methyl ester / ethyl ester containing part of free fatty acid and glycerol are adopted as materials, the immobilized lipase is adopted as a catalyst, conjugated linoleic acid ester and the glycerol are alternatively charged at the early stage, so that contact probability of the glycerol and the immobilized lipase is effectively increased, and reaction efficiency is increased; conjugated linoleic acid glyceride is prepared by virtue of a mixed charging method of the conjugated linoleic acid ester and the glycerol at a later stage; the free fatty acid and glycerol react to generate water molecules which are beneficial to playing of enzyme activity, so that reaction efficiency is quickened; meanwhile, methyl alcohol or alcohol is removed online by virtue of a way of charging a nitrogen gas or vacuum-pumping in a reaction process, so that reaction time is greatly shortened; and any organic reagent is not needed to be added in the whole preparation process, and residue of any organic solvent is not caused. Compared with the known glyceride preparation method, the method disclosed by the invention is simpler, lower in cost; and the obtained conjugated linoleic acid glyceride product is higher in quality and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing conjugated linoleic acid glycerides by using immobilized lipase. Background technique [0002] Conjugated linoleic acids (CLA) is a general term for several stereo and positional isomers of linoleic acid (Linoleic acids, LA) molecules. Enenoic acid. The double bond of CLA mainly has four positions on the carbon chain: 8,10-, 9,11-, 10,12- and 11,13-, and because the carbon atoms at both ends of the conjugated double bond have cis Formula (cis) and trans (trans) two geometric configurations, that is, each positional isomerism has four geometric isomers of cis-cis, cis-trans, trans-cis, and trans-trans, so CLA isomerism There are many types of bodies. Among them, c9, t11-CLA and t10, c12-CLA are the two main isomers with the most content and proved to have physiological activity. Natural CLA mainly exists in the milk fat and meat products of rumen animals such as cattle and sheep, with the content rangi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/64
Inventor 吴文忠杨大苹伏萃翠徐维锋姜书华洪永德
Owner INNOBIO CORP LTD
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