Process for preparing and separating methyl docosapentaenoate and methyl docosahexenoate

A kind of technology of methyl docosahexaenoate and methyl docosahexaenoate, applied in the field of preparation and separation of methyl docosahexaenoate and methyl docosahexaenoate , which can solve the problems of complicated brine shrimp meal process and lower yield, and achieve the effect of short heating time, avoided loss and high yield.

Active Publication Date: 2008-09-17

NANGTONG HAODI ANTICORROSION EQUIP

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Problems solved by technology

[0006] Application No. 03113397.5 discloses a method for preparing DHA value through marinated shrimp protein powder. The process of preparing ...

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Abstract

The invention relates to a preparation and separation method of docosapentaenoic acid methyl ester and docosahexaenoic acid methyl ester. Microalgae oil is used as raw material to prepare docosapentaenoic acid and docosahexaenoic acid which are mixed with fatty acid to prepare the docosapentaenoic acid methyl ester and the docosahexaenoic acid methyl ester. The separation method of the the docosapentaenoic acid methyl ester and the docosahexaenoic acid methyl ester provided by the method adopts a silver nitrate column method of separating. In the silver nitrate column method, the quality of the methyl ester sample introduction of the mixed fatty acid is 0.5 percent to 10 percent of the quality of filled silver nitrate blangel; elution gradient is n-hexane solution containing acetone the content of which is 0.5 percent to 15 percent; the elution speed is 0.5 to 5ml/min. The preparation and separation method utilizes the silver nitrate column method to obtain the high purity docosapentaenoic acid methyl ester and the high purity docosahexaenoic acid methyl ester, wherein, the content of DPA is raised from 20.32 percent in raw oil to 99.61 percent, the content of DHA is raised from 44.83 percent to 99.02 percent, and the yield rate by using the silver nitrate column method can reach more than 90 percent.

Application Domain

Organic compound preparationCarboxylic acid esters preparation

Technology Topic

ChemistryDocosapentaenoate +11

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Examples

Experimental program(4)

Example Embodiment

[0025] [Example 1]

[0026] The preparation of high-purity docosapentaenoic acid (DPA) methyl ester and docosahexaenoic acid (DHA) methyl ester by the silver nitrate column method includes the following steps:

[0027] 1) Preparation of crude fatty acid: Take 500g of microalgae oil, 50g of KOH, and 1000ml of methanol, add it to a three-necked flask, use nitrogen as protective gas, keep stirring, and reflux in a water bath at 60-120°C for 1 to 4 hours. After removing most of the solvent by rotary evaporation, 6mol/L hydrochloric acid was added for acidification, and the fatty acid was extracted three times with 300ml petroleum ether, and then 5% NaCl aqueous solution was added to wash the ether phase until the washing liquid was neutral. Add anhydrous Na 2 SO 4 Absorb the residual moisture in the ether phase, and spin-evaporate at 60°C to remove the solvent to obtain crude fatty acid.

[0028] 2) Preparation of DPA and DHA mixed fatty acid: Take 100g crude fatty acid, 30g~300g urea, 600ml methanol and mix, reflux in a water bath at 60~90℃ for 15 minutes, then cool and crystallize at 0℃ for 3~30 hours, quickly pump filter. After the filtrate was rotary evaporated to remove most of the solvent, it was dissolved by adding water. The fatty acid was extracted twice with petroleum ether, and the liquids were separated. After washing away the residual urea in the ether phase with water, add anhydrous Na 2 SO 4 Absorb the residual moisture in the ether phase, and remove the solvent by rotating and steaming at 60°C to obtain a high content of DPA and DHA mixed fatty acid.

[0029] 3) Methyl esterification of DPA and DHA mixture: 50g DPA and DHA mixed fatty acid, 10ml~100ml BF 3 -After the methanol solution is mixed, reflux in a water bath at 60-90°C for 15 minutes, then add saturated NaCl solution to the reactant, shake for a while until a white precipitate is formed, extract the mixture of DPA methyl ester and DHA methyl ester with 150ml of n-hexane, and evaporate to remove the solvent .

[0030] 4) DPA methyl ester and DHA methyl ester were obtained by silver nitrate column method: ①Ag + Prefabrication of silica gel. Weigh 50g~250g silica gel (for column chromatography, 200~300 mesh), add 250g ethanol to make a paste, keep stirring for 10 minutes. 2g~20gAgNO 3 Dissolve in 100ml ethanol (70%, v/v), mix with paste silica gel, and continue to stir for 10 to 90 minutes. After evaporating the solvent, the Ag +The silica gel is moved into an oven at 120°C and activated for 12-24 hours. Take it out and put it in a desiccator away from light for later use. ②Weigh 20g Ag prepared + Silica gel, wet packed column with n-hexane as eluent. Take 1g of the mixture of DPA methyl ester and DHA methyl ester and load the sample. Elute with 0.5% acetone in n-hexane solution 500ml~2000ml, 3% acetone in n-hexane solution 500ml~2000ml, 10% acetone in n-hexane solution 1000ml~5000ml, each 60ml is a sample, evaporate and remove the solvent by gas chromatography Detect and combine the same components to obtain high-purity DPA methyl ester and DHA methyl ester.

Example Embodiment

[0031] [Example 2]

[0032] The basic process is the same as in Example 1, and the specific operating parameters are as follows:

[0033] 1) Preparation of crude fatty acid: Take 250g of seaweed oil, 50g of KOH, and 500ml of methanol, add it to a three-necked flask, use nitrogen as protective gas, keep stirring, and reflux in a water bath at 60-120°C for 2 hours. After removing most of the solvent by rotary evaporation, 6mol/L hydrochloric acid was added for acidification, the fatty acid was extracted three times with 300ml petroleum ether, and the ether phase was washed with 5% NaCl aqueous solution until the washing liquid was neutral. Add anhydrous Na 2 SO 4 Absorb the residual moisture in the ether phase, and spin-evaporate at 60°C to remove the solvent to obtain crude fatty acid.

[0034] 2) Preparation of DPA and DHA mixed fatty acid: Take 75g crude fatty acid, 150g urea, 600ml methanol and mix, reflux in a water bath at 50-80°C for 15 minutes, cool and crystallize at -10°C for 27 hours, and quickly filter with suction. After the filtrate was rotary evaporated to remove most of the solvent, it was dissolved by adding water. The fatty acid was extracted twice with 100ml petroleum ether, and the liquids were separated. After washing away the residual urea in the ether phase with water, add anhydrous Na 2 SO 4 Absorb the residual moisture in the ether phase, and spin-evaporate at 60°C to remove the solvent to obtain a high-content DPA and DHA mixed fatty acid.

[0035] 3) Methyl esterification of DPA and DHA mixture: 50g DPA and DHA mixed fatty acid, 500mlBF 3 -After mixing the methanol solution, reflux in a water bath at 50-80°C for 15 minutes, then add a saturated NaCl solution to the reactant, shake for a while until a white precipitate is formed, extract the DPA methyl ester and DHA methyl ester mixture with n-hexane, and evaporate to remove the solvent.

[0036] 4) Silver nitrate column method to obtain DPA methyl ester and DHA methyl ester: Prepare Ag according to the method in Example 1. + Silica gel, weigh 50g of Ag + Silica gel, wet packed column with n-hexane as eluent. Take 5 g of a mixture of DPA methyl ester and DHA methyl ester and load the sample. Elute with 2000ml of 1% acetone in n-hexane solution, 500ml of 7% acetone in n-hexane solution, and 1000ml of 15% acetone in n-hexane solution, each 60ml as a sample, evaporate and remove the solvent, detect by gas chromatography, combine the same group Separately, high-purity DPA methyl ester and DHA methyl ester can be obtained.

Example Embodiment

[0037] [Example 3]

[0038] The basic process is the same as in Example 1, and the specific operating parameters are as follows:

[0039] 1) The preparation of crude fatty acid, the preparation of DPA and DHA mixed fatty acid and the methyl esterification of DPA and DHA mixture are the same as in Example 2.

[0040] 2) Silver nitrate column method to obtain DPA methyl ester and DHA methyl ester: Prepare Ag according to the method in Example 1. + Silica gel, weighing out 100g Ag + Silica gel, wet packed column with n-hexane as eluent. Take 0.5 g of the mixture of DPA methyl ester and DHA methyl ester and load the sample. Elute with 2000ml of 0.5% acetone in n-hexane solution, 500ml of 10% acetone in n-hexane solution, and 1000ml of 15% acetone in n-hexane solution, each 60ml as a sample, evaporate and remove the solvent, detect by gas chromatography, combine the same group Separately, high-purity DPA methyl ester and DHA methyl ester can be obtained.

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Classification and recommendation of technical efficacy words

High purity
High yield

Process for preparing and separating methyl docosapentaenoate and methyl docosahexenoate

AI-Extracted Technical Summary

Problems solved by technology

Abstract

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Examples

Example Embodiment

Example Embodiment

Example Embodiment

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Description & Claims & Application Information

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