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Preparation method of conjugated linoleic acid

A technology of conjugated linoleic acid and linoleic acid, which is applied in the preparation of carboxylate salts, organic compounds, chemical instruments and methods, etc., which can solve the difficulties in separation of products, solvents and catalysts, high production costs, and high reaction viscosity and other problems, to achieve the effect of solvent recycling, low production cost and simple post-processing

Inactive Publication Date: 2009-10-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantages are low yield, difficult separation of conjugated linoleic acid and reaction mixture, and high cost, which is not conducive to industrial production
4. Photocatalytic isomerization method: using photosensitizer to undergo isomerization reaction under a certain light wave radiation, its disadvantages are harsh equipment requirements, difficult separation of photosensitizer and reaction product, long reaction time, and low conversion rate (Jain VP and Proctor A, Journal of Agricultural and Food Chemistry, 2006, 54, 5590-5596)
The disadvantage is that alkali metal alkoxides have limited solubility in solvents, excessive alkoxides are required, the reaction viscosity is relatively large, and sometimes phase transfer catalysts need to be added, the separation of product, solvent and catalyst is difficult, the recovery of phase transfer catalysts is difficult, and the production cost is high.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 15.06g of safflower seed oil, 180g of methanol and 10g of NaOH into the reactor, then fill it with nitrogen to remove the air, close the system, stir with the stirrer at 800rpm, rapidly raise the temperature to 160°C, react at constant temperature for 3h, and the reaction ends. Cool to room temperature. The reaction mixture was transferred to a round-bottomed flask, and 40° C. was rotary evaporated under vacuum to recover methanol. Then add 200ml of distilled water in the round bottom flask and transfer the mixture to the beaker, add hydrochloric acid to neutralize the acidification, adjust the pH value to 3, transfer the mixture to the separatory funnel, extract three times with n-hexane, then combine the n-hexane layers, Wash three times with 5% saline and distilled water respectively. The n-hexane solvent was evaporated under reduced pressure in a rotary evaporator to obtain 14.08 g of mixed fatty acids. The conversion rate of linoleic acid detected by GC was...

Embodiment 2

[0025]Weigh 14.94g of sunflower oil, 180g of methanol and 7.5g of NaOH into the reaction kettle, then fill it with nitrogen and evacuate it, close the system, stir with the stirrer at 800rpm, rapidly raise the temperature to 180°C, react at constant temperature for 2h, and the reaction ends. Cool to room temperature. The reaction mixture was transferred to a round-bottomed flask, and 40° C. was rotary evaporated under vacuum to recover methanol. Then add the distilled water of 200ml in the round bottom flask and transfer the mixture to the beaker, add phosphoric acid to neutralize the acidification, adjust the pH value to 2, transfer the mixture to the separatory funnel, extract three times with n-hexane, then combine the n-hexane layers, Wash three times with 5% saline and distilled water respectively. The n-hexane solvent was distilled off under reduced pressure in a rotary evaporator to obtain 13.74 g of mixed fatty acids. The conversion rate of linoleic acid detected by ...

Embodiment 3

[0027] Weigh 15.03g of soybean oil, 120g of methanol and 5g of NaOH. Adopt the same processing step as example 1, obtain mixed fatty acid 13.88g. The conversion rate of linoleic acid detected by GC was 97.6%, the yield of conjugated linoleic acid was 85.1%, and the proportion of c9, t11-CLA and t10, c12-CLA in the total CLA was 97.3%.

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Abstract

The invention relates to a preparation method of conjugated linoleic acid, comprising the following steps: placing the vegetable oil containing linoleic acid glyceride or mixed fatty acid containing linoleic acid or extracted and separated linoleic acid product as raw material, low boiling point alcohols solvent and base catalyst into a reaction kettle and performing the isomerization reaction at a certain temperature. The reaction product is subjected to evaporating, acidifying, extracting and vacuum drying to obtain the conjugated linoleic acid. The conversion of the linoleic acid is above 97.5% and the total yield of the conjugated linoleic acid is above 85%, the proportions of the cis-9, trans-11 isomer and trans-10, cis-12 isomer in the total conjugated linoleic acid are above 96%. The preparation method has features of less reaction steps, easy recovery and repeated use of solvent, simple follow-up separation, low production cost, and easy industrialization.

Description

technical field [0001] The invention relates to a chemical synthesis method of alkali-catalyzed isomerization linoleic acid, in particular to a preparation method of conjugated linoleic acid. Background technique [0002] Conjugated Linoleic Acid (CLA) is a general term for various positional isomers and geometric isomers of octadecadienoic acid containing conjugated double bonds. Conjugated double bonds can be 7, 9-, 8, 10-, ..., 12, 14-positions of the carbon chain, and they have cis-cis (c, c), cis-trans (c, t) , anti-anti (t, t) geometric isomerism. These isomers show different chemical properties and physiological functions from linoleic acid due to the difference in position and spatial conformation, but the properties of each isomer are not yet fully understood. Studies have shown that cis-9, trans-11 isomers and trans-10, cis-12 isomers have the most physiological activity. Trans-10, cis-12 isomers have special effects on fat, which can inhibit lipid uptake and fa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/12C07C51/353C11C3/14
Inventor 杨亦文刘瑞阳鲍宗必苏宝根苏云邢华斌任其龙
Owner ZHEJIANG UNIV
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