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Method for preparing ethyl eicosapentaenate (EPA) and ethyl docosahexaenoate (DHA)

An ethyl ester and preparation type technology is applied in the field of preparation of EPA ethyl ester and DHA ethyl ester, and can solve the problems of inability to achieve simultaneous separation, high toxicity of acetonitrile, pollution and the like

Active Publication Date: 2014-07-30
THIRD INST OF OCEANOGRAPHY STATE OCEANIC ADMINISTATION
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both silver resin chromatography and silver nitrate complexation use expensive silver nitrate, and the recovery of silver nitrate is difficult and pollutes seriously
High-performance liquid chromatography-ultraviolet method often uses acetonitrile / tetrahydrofuran / water or methanol / tetrahydrofuran / water as the mobile phase system. In this system, acetonitrile is relatively toxic, and tetrahydrofuran is easy to introduce peroxides, resulting in a decline in product quality.
In addition, silver resin chromatography, silver nitrate complexation, supercritical fluid chromatography, and high performance liquid chromatography-ultraviolet method also cannot realize simultaneous separation and obtain purity greater than 99% EPA ethyl ester and DHA ethyl ester

Method used

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  • Method for preparing ethyl eicosapentaenate (EPA) and ethyl docosahexaenoate (DHA)
  • Method for preparing ethyl eicosapentaenate (EPA) and ethyl docosahexaenoate (DHA)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of raw materials: the crude fish oil with a total content of EPA ethyl ester and DHA ethyl ester of 80% is prepared into a pre-separated preparation solution containing 200 mg of the crude product per ml, and set aside.

[0019] Instrument: Preparative high performance liquid chromatography-mass spectrometry instrument system.

[0020] Chromatographic conditions: the preparation chromatographic column is a C18 column (250mm×20mm); the mobile phase system is 90% methanol aqueous solution, and the flow rate of the mobile phase is 20mL / min.

[0021] Injection concentration: 200mg / mL.

[0022] Injection volume: 1 mL.

[0023] Mass spectrometry detection conditions: atmospheric pressure chemical ionization source (APCI), positive ion mode, corona current 3.0μA, primary cone voltage 30V, secondary cone voltage 3.0V, source temperature 120°C, desolvation temperature 350°C, desolvation nitrogen flow rate 300L / h, cone nitrogen flow rate 50L / h, high and low mass res...

Embodiment 2

[0026] Raw materials for preparation: the crude fish oil with a total content of EPA ethyl ester and DHA ethyl ester of 70% is prepared into a pre-separated preparation solution containing 150 mg of the crude product per milliliter, and set aside.

[0027] Instrument: Preparative high performance liquid chromatography-mass spectrometry instrument system.

[0028] Chromatographic conditions: the preparation chromatographic column is a C8 column (250mm×20mm); the mobile phase system is 85% methanol aqueous solution, and the flow rate of the mobile phase is 20mL / min.

[0029] Injection concentration: 150mg / mL.

[0030] Injection volume: 1.5mL.

[0031] Mass spectrometry detection conditions: atmospheric pressure chemical ionization source (APCI), positive ion mode, corona current 3.0μA, primary cone voltage 30V, secondary cone voltage 3.0V, source temperature 120°C, desolvation temperature 350°C, desolvation nitrogen flow rate 300L / h, cone nitrogen flow rate 50L / h, high and low...

Embodiment 3

[0034] Preparation of raw materials: the crude fish oil with a total content of EPA ethyl ester and DHA ethyl ester of 60% is prepared into a pre-separated preparation solution containing 200 mg of the crude product per ml, and set aside.

[0035] Instrument: Preparative high performance liquid chromatography-mass spectrometry instrument system.

[0036]Chromatographic conditions: the preparation chromatographic column is a C18 column (250mm×30mm); the mobile phase system is 85% ethanol aqueous solution, and the flow rate of the mobile phase is 45mL / min.

[0037] Injection concentration: 200mg / mL.

[0038] Injection volume: 2.5mL.

[0039] Mass spectrometry detection conditions: atmospheric pressure chemical ionization source (APCI), positive ion mode, corona current 3.0μA, primary cone voltage 30V, secondary cone voltage 3.0V, source temperature 120°C, desolvation temperature 350°C, desolvation nitrogen flow rate 300L / h, cone nitrogen flow rate 50L / h, high and low mass reso...

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Abstract

The invention discloses a method for preparing ethyl eicosapentaenate (EPA) and ethyl docosahexaenoate (DHA) and relates omega-3 long-chain polyunsaturated fatty acids. The method comprises: preparing prepared solution to be separated by using a fish oil coarse raw material, which contains ethyl EPA and ethyl DHA, and using an organic solvent as a solvent; transferring the prepared solution to be separated into a material storage tube of a semi-prepared / prepared high-efficiency liquid chromatography-mass spectrum combined apparatus system, starting the semi-prepared / prepared high-efficiency liquid chromatography-mass spectrum combined apparatus system of which a mobile phase is aqueous solution of methanol or ethanol, balancing a chromatographic column, sampling automatically, separating and purifying ethyl EPA and ethyl DHA, and trigging a distillate collector by a mass spectrum online detection signal to collect pure ethyl EPA liquid and ethyl DHA liquid separately and automatically; and subjecting the pure ethyl EPA and ethyl DHA to reduced pressure concentration, extraction and reduced-pressure concentration respectively and thus obtaining ethyl EPA and ethyl DHA, of which the purities are both over 99 percent. The method is characterized by simple and convenient operation and high yield and is suitable for automatic control and synchronous separation.

Description

technical field [0001] The invention relates to an omega-3 series polyene long-chain fatty acid, in particular to a preparation method of EPA ethyl ester and DHA ethyl ester with a purity greater than 99%. Background technique [0002] All cis-5, 8, 11, 14, 17-eicosapentaenoic acid (cis-5, 8, 11, 14, 17-Eicosapentaenoic Acid, EPA) and all cis-4, 7, 10, 13, 16 , 19-docosahexaenoic acid (cis-4, 7, 10, 13, 16, 19-Docosahexaenoic Acid, DHA) all belong to the omega-3 series of polyene long-chain fatty acids, that is, the third from the terminal methyl group There are double bonds on each carbon, and the multiple double bonds in the molecule are in the non-conjugated system, and they are all in the cis configuration. EPA and DHA products usually come as ethyl ester compounds, EPA ethyl ester (EPA-EE) and DHA ethyl ester (DHA-EE). [0003] EPA and DHA are essential omega-3 unsaturated fatty acids for the human body, and have good curative effects in the treatment and prevention o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/587C07C67/56
Inventor 谢全灵洪专易瑞灶张怡评方华陈伟珠晋文慧
Owner THIRD INST OF OCEANOGRAPHY STATE OCEANIC ADMINISTATION
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