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Preparation method of conjugated linoleic acid glycerides

A technology of conjugated linoleic acid glycerides and conjugated linoleic acid, which is applied in the field of preparation of conjugated linoleic acid glycerides, can solve the problem of low production efficiency, reaction time of up to 20 hours or even 75 hours, and high cost Inappropriate and other problems, to achieve the effect of short reaction time, simple post-processing, and high safety

Active Publication Date: 2012-07-18
INNOBIO CORP LTD
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0004] At present, the preparation method of conjugated linoleic acid glyceride is mainly based on enzyme catalysis, as disclosed in the patent "Synthesis of conjugated linoleic acid glyceride derivatives based on enzymatic method" (CN 101200741A), using enzymes in organic solvents Catalyzed reaction between conjugated linoleic acid and glycerol compounds to prepare conjugated linoleic acid glycerides; however, using enzyme-catalyzed method, although the reaction is mild, the reaction time is as long as 20 hours or even 75 hours, and n-hexane and other organic solvents, the product yield is only 40-50%; this method has low production efficiency and high cost and is not suitable for industrialized production

Method used

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  • Preparation method of conjugated linoleic acid glycerides
  • Preparation method of conjugated linoleic acid glycerides
  • Preparation method of conjugated linoleic acid glycerides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1. Under the situation of blowing nitrogen gas, add dropwise 4.4 kg of 24% potassium ethoxide ethanol solution to 50 kg of methyl linoleate at 100°C; react for 3 hours, and finish the reaction with a methyl linoleate content of 1.1%;

[0037] ② After cooling down, add 50 liters of 60% methanol aqueous solution to wash the reactants in ①; let stand to separate liquid, and decompress and precipitate the oil layer;

[0038]③Set the molecular distillation heating temperature at 160°C; control the vacuum degree at 20Pa, and distill to obtain refined conjugated methyl linoleate.

[0039] ④ After mixing methyl conjugated linoleate and glyceryl acetate in a molar ratio of 3.1:1, raise the temperature to 125°C under nitrogen protection, and add the catalyst potassium methoxide solution dropwise. 3%, catalyze the ester exchange reaction, and react until the triglyceride content is qualified to start the high vacuum reaction to the end;

[0040] ⑤ Add 50 liters of 60% methanol aq...

Embodiment 2

[0047] 1. Under the situation of blowing nitrogen gas, add dropwise 4.73 kg of 23.8% concentration of potassium ethoxide ethanol solution to 75 kg of ethyl linoleate at 110°C; react for 2 hours, and the content of methyl linoleate is 1.14% to end the reaction;

[0048] ② After cooling down, add 7.5 liters of 30% aqueous ethanol solution to wash the reactants in ①; let stand to separate liquid, and decompress and precipitate the oil layer;

[0049] ③Set the molecular distillation heating temperature at 175°C; control the vacuum degree at 24±2Pa, and distill to obtain refined conjugated ethyl linoleate;

[0050] ④ After mixing ethyl conjugated linoleate and glyceryl acetate in a molar ratio of 3.2:1, raise the temperature to 145°C under the protection of nitrogen, and add the catalyst potassium ethylate solution dropwise. The dosage of potassium ethylate is changed to glyceryl acetate 4% of the mass, catalyze the transesterification reaction, and react until the triglyceride con...

Embodiment 3

[0057] 1. In the case of nitrogen blowing, add dropwise 187.5 kg of 20.8% concentration of sodium methoxide methanol solution to 500 kg of ethyl linoleate at 140°C; react for 3.5 hours, and the methyl linoleate content is 0.95% to end the reaction;

[0058] ② After cooling down, add 450 liters of 70% aqueous ethanol solution to wash the reactants in ①; let stand to separate the liquid, and decompress and precipitate the oil layer;

[0059] ③Set the molecular distillation heating temperature at 165°C; control the vacuum degree at 20Pa, and distill to obtain refined conjugated ethyl linoleate.

[0060] ⑤ After mixing ethyl conjugated linoleate and glyceryl acetate in a molar ratio of 3.5:1, raise the temperature to 150°C under nitrogen protection, and add the catalyst sodium ethoxide solution dropwise. The amount of sodium ethoxide is the mass of glyceryl acetate 0.8%, catalyze the transesterification reaction, react until the triglyceride content is qualified, start the high va...

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Abstract

A preparation method of conjugated linoleic acid glycerides comprises the following steps: (1) C1-4 sodium alcoholate / potassium alcoholate is taken as a catalyst, linoleic acid short-chain alcohol ester is prepared to be conjugated linoleic acid short-chain alcohol ester through inversion reaction for 1-8 hours at 90-150 DEG C, and the using amount of the catalyst is 1.5-8.0% of weight of the linoleic acid short-chain alcohol ester; (2) sodium methylate / potassium methylate and sodium ethoxide / potassium ethoxide are taken as catalysts, the conjugated linoleic acid short-chain alcohol ester and acetoglyceride with mole ratio being 3:1-3.5:1 are reacted for 3-10 hours at 100 DEG C and 170 DEG C to prepare the conjugated linoleic acid glycerides, and the using amount of the catalysts is 0.8-10% of the weight of acetoglyceride. According to the preparation method, the natural resources are utilized sufficiently, an organic solvent is not needed in the main reaction; the esterification rate of conjugated oil acid is more than 99%; the reaction time is short, and the postprocessing simple; the triglyceride content of the conjugated linoleic acid glycerides is more than 90%, and the acid value of the conjugated linoleic acid glycerides is under 1.0mgKOH / g; and the conjugated linoleic acid glycerides is free from extraneous odor, good in taste and light in color, and the optimal Gar is less than or equal to 1.0.

Description

technical field [0001] The invention relates to a preparation method of conjugated linoleic acid glycerides, in particular to a method for preparing conjugated linoleic acid glycerides by using short-chain alcohol esters of linoleic acid as raw materials and utilizing transposition reaction and transesterification reaction. Background technique [0002] Conjugated linoleic acid (CLA) is an isomer of linoleic acid. A large number of in-depth studies by scientists have shown that conjugated linoleic acid and its esters and salt derivatives have the ability to reduce animal and human fat Increase muscle, reduce blood fat, resist atherosclerosis, increase bone density, regulate blood sugar, regulate blood pressure and many other important physiological functions. Therefore, conjugated linoleic acid and its esters and salt derivatives have attracted international attention in the food industry. and medical attention. [0003] Free fatty acid conjugated linoleic acid (Conjugated ...

Claims

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Application Information

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IPC IPC(8): C07C69/587C07C67/02
Inventor 吴文忠张显仁刘明徐维锋刘强吴迪
Owner INNOBIO CORP LTD
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