CN1204638A - Preparation of docosahexenoic acid and esterification technology - Google Patents
Preparation of docosahexenoic acid and esterification technology Download PDFInfo
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- CN1204638A CN1204638A CN 97108136 CN97108136A CN1204638A CN 1204638 A CN1204638 A CN 1204638A CN 97108136 CN97108136 CN 97108136 CN 97108136 A CN97108136 A CN 97108136A CN 1204638 A CN1204638 A CN 1204638A
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Abstract
A process for preparing health-care nutritive docosahexenoic acid with fish oil as raw material includes saponifying reaction, acidifying reaction, esterifying reaction and vacuum rectification to obtain the mixture of ethyl ester of docosahexenoic acid and ethyl ester of eicosapentaenoic acid. In the saponifying reaction, 95% alcohol (6.5-7.5 weight portions), potassium hydroxide (1) and fish oil (4.5-5.0) are mixed, heated and saponified. After esterifying reaction, high-vacuum rectification is used to extract the docosahexenoic acid as health-care nutritive product which is colourless and odourless.
Description
The present invention relates to a processing technology for extracting health-care and nutrient components from fish oil.
The docosahexaenoic acid and the eicosapentaenoic acid (DHA and EPA are respectively abbreviated as English) have good nutrition and health care functions, including health care functions of strengthening brain, improving intelligence, improving eyesight, strengthening heart and the like, can enhance intelligence of children and prevent senile dementia, and alsohave good prevention and treatment effects on hypertension and cardiovascular diseases. DHA exists in shellfish bodies, is a highly unsaturated fatty acid mainly extracted from fish oil, belongs to natural food, and is an ideal nutritional health product. The main effective components of the 'brain gold' nutrition health care product which is popular in the market recently are DHA and EPA. The various types of DHA-containing products are broadly classified into three types, i.e., fish oil type, fatty acid type, and ethyl ester type, and are generally mixtures of DHA and EPA, and are conventionally collectively referred to as DHA products (including foods and pharmaceuticals). The development of DHA-based products is now quite dramatic. The raw material for extracting DHA and EPA is mainly marine fish oil, but various extraction process methods at home and abroad have the defects of long process flow, complex equipment, large investment and the like to different degrees at present, and the content, color or smell of the obtained DHA and EPA extracts are not ideal; in addition, most of the DHA-containing food and medicine on the market are sold in the form of capsules, mainly because the deodorization technology is not over-done, and the DHA product is limited in form and application range only by preparing the capsules to cover the intolerable fishy smell.
The invention aims to provide a preparation and esterification process which has the advantages of short process flow, simple equipment and low investment and can obtain the extract containing docosahexaenoic acid and eicosapentaenoic acid with high quality.
The technical scheme of the invention is as follows: the invention adopts fish oil as raw material, which comprises saponification reaction, acidification reaction, esterification reaction and vacuum rectification to prepare a mixture containing docosahexaenoic acid ethyl ester andeicosapentaenoic acid ethyl ester.
In the saponification reaction, alcohol with the purity of 95 percent, potassium hydroxide and fish oil are adopted to carry out saponification reaction, wherein the weight ratio of the alcohol to the potassium hydroxide to the fish oil is (6.5-7.5) to 1 to (4.5-5.0) in sequence. In the saponification reaction, after alcohol, potassium hydroxide and fish oil are uniformly mixed, a reflux condenser tube is arranged, the mixture is heated and reacted for two hours at the alcohol reflux temperature, the fish oil is completely saponified, and then the alcohol in the saponification mixture is completely distilled out. The chemical formula of the saponification reaction is:
the acidification reaction is to add concentrated hydrochloric acid into saponified substance after saponification reaction, stir it evenly to convert the saponified substance into fatty acid, add water to wash the acidified substance, and separate water phase and oil phase. The chemical formula of the acidification reaction is:
and the esterification reaction is to add a proper amount of concentrated hydrochloric acid and anhydrous alcohol into the acidified substance after the acidification reaction, heat the acidified substance for two hours to complete the esterification, evaporate all the alcohol in the esterification mixture, wash the esterified substance by adding hot water until the pH value is 6-7 to be neutral, and separate water and an oil phase to obtain a crude mixed fatty acid ethyl ester product. The chemical formula of the esterification reaction is:
the vacuum rectification process ofthe invention adopts vacuum diffusion pump rectification. The absolute vacuum degree in the vacuum rectification process is not lower than 0.001 mm Hg, and the cut-off temperature is 110-160 ℃. DHA has a molecular formula of C22H32O2EPA with the molecular formula C20H30O2。
As DHA and EPA both belong to omega-3 type long-chain highly unsaturated fatty acid, the double bond structure is an all-cis non-conjugated structure, and the structure is easy to generate conjugated isomers under high temperature, thereby reducing the health care and medical effects. The invention adopts the high vacuum rectification technology, reduces the processing temperature, and the product has no isomer through mass spectrum measurement, thereby ensuring that the medical health care effect of DHA and EPA can not be reduced in the extraction process. In addition, the vacuum rectification technology ensures that the prepared DHA product has normal smell, can be prepared into capsules, can also be prepared into oral liquid or added into other foods to be used for preparing various DHA-containing foods, and meets different requirements of various consumers in the market. For example, can be further developed into infant brain-strengthening food, student intelligence-improving food and senile dementia-preventing food, and can also be used for regulating DHA and EPA content ratio and developing health-care medicines for preventing and treating hypertension, cerebral thrombosis and cardiovascular diseases.
The product produced by the process of the invention belongs to ethyl ester type. The DHA and EPA distillation range of the ethyl docosahexaenoic acid ester obtained by high vacuum distillation can reach 70%, and the product with the content of 50% can be obtained by cutting according to the requirement, wherein the yield of the product is about 90%, and the product is clear and transparent, colorless to light yellow and odorless oily liquid. The product of the invention has high quality, and all technical indexes can meet the higher requirements of DHA foods.
In conclusion, the method has the advantages of short process flow, simple equipment, investment saving, convenient operation and the like, has good decolorization and deodorization effects, advanced and reasonable process, is easy to apply, is an ideal method for producing high-quality DHA products, has high quality of the obtained extract containing the docosahexaenoic acid and the eicosapentaenoic acid, has high DHA and EPA contents in the products, has ideal color and taste, and is suitable for further producing various nutritional health-care foods or medicines.
The present invention will be described in detail with reference to examples.
Example (b): the fish oil produced by the marine fish processing plant generally contains more than 10 percent of DHA and is thick oily liquid with strong fishy smell; other raw materials include: 95% alcohol, anhydrous alcohol, potassium hydroxide, and concentrated hydrochloric acid. The method comprises the following specific steps:
(1) saponification reaction: adding 10 kg of potassium hydroxide into 65 kg of alcohol to prepare potassium hydroxide alcohol solution, adding 50 kg of fish oil, uniformly mixing, filling a reflux condenser pipe, heating and reacting for two hours at the alcohol reflux temperature, completely saponifying the fish oil, and completely distilling out the alcohol in the saponified mixture.
(2) And (3) acidification reaction: adding concentrated hydrochloric acid into saponified substance, adjusting pH =2, stirring well, simultaneously precipitating a large amount of KCL, at this time, the saponified substance has been converted into fatty acid, adding waterto wash the acidified substance, and separating water phase and oil phase.
(3) Esterification reaction: adding 2.5 kg of concentrated hydrochloric acid and 60 kg of absolute alcohol into the acidized substance after the reaction, and heating for reaction for two hours; and after the esterification is finished, completely distilling off alcohol in the esterification mixture, washing the esterified substance by adding hot water until the pH value is 6-7 to be neutral, and separating water from an oil phase to obtain a crude product of the mixed fatty acid ethyl ester. The product yield is about 95 percent.
(4) Vacuum rectification: rectifying by using a vacuum diffusion pump. Under the condition that the absolute vacuum degree is not lower than 0.001 mm Hg, intercepting the distillate at 110-130 ℃. The DHA + EPA content in the obtained product is about 70%, and the yield is about 90%. The product is a transparent oily liquid with yellowish color and pure fish oil smell (no peculiar smell).
Claims (7)
1. A process for preparing docosahexaenoic acid and esterifying it features that fish oil is used as raw material. The method is characterized in that the process comprises saponification reaction, acidification reaction, esterification reaction and vacuum rectification to prepare a mixture containing docosahexaenoic acid ethyl ester and eicosapentaenoic acid ethyl ester.
2. The process for preparing and esterifying docosahexaenoic acid as claimed in claim 1, wherein the saponification reaction is carried out by using 95% alcohol and potassium hydroxide and fish oil in the weight ratio of (6.5-7.5) to 1 to (4.6-5.0).
3. The process of claim 1, wherein the saponification reaction comprises mixing ethanol, potassium hydroxide and fish oil, placing into a reflux condenser, heating at ethanol reflux temperature for two hours to complete saponification of fish oil, and distilling off all ethanol from the saponified mixture.
4. The process for preparing and esterifying docosahexaenoic acid as claimed in claim 1, wherein the acidification reaction is carried out by adding concentrated hydrochloric acid into saponified substance after saponification reaction, stirring to convert saponified substance into fatty acid, adding water to wash acidified substance, and separating water phase and oil phase.
5. The process for preparing and alcoholizing docosahexaenoic acid according to claim 1, wherein the esterification reaction is carried out by adding a proper amount of concentrated hydrochloric acid and absolute alcohol into the acidified product after the acidification reaction, heating for two hours to complete esterification, steaming out all alcohol in the esterification mixture, washing the esterified product with hot water until the pH value is 6-7 to be neutral, and separating water and oil phase to obtain the crude product of mixed fatty acid ethyl ester.
6. The process for the preparation and esterification of docosahexaenoic acid according to claim 1, wherein the vacuum rectification process employs vacuum diffusion pump rectification.
7. The process of claim 1, wherein the absolute vacuum degree during the vacuum distillation is not lower than O.001 mm Hg, and the temperature of the distillate cut is 110-160 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 97108136 CN1204638A (en) | 1997-07-02 | 1997-07-02 | Preparation of docosahexenoic acid and esterification technology |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 97108136 CN1204638A (en) | 1997-07-02 | 1997-07-02 | Preparation of docosahexenoic acid and esterification technology |
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| CN1204638A true CN1204638A (en) | 1999-01-13 |
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| CN 97108136 Pending CN1204638A (en) | 1997-07-02 | 1997-07-02 | Preparation of docosahexenoic acid and esterification technology |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101796014A (en) * | 2007-06-29 | 2010-08-04 | 马泰克生物科学公司 | Production and purification of esters of polyunsaturated fatty acids |
| CN102448314A (en) * | 2009-06-02 | 2012-05-09 | 金欧米茄公司 | Method for producing a concentrate of eicosapentaenoic and docosahexaenoic acid esters |
| CN101213281B (en) * | 2005-05-04 | 2013-03-13 | 普罗诺瓦生物医药挪威公司 | New dha derivatives and their use as medicaments |
| CN103281910A (en) * | 2010-12-27 | 2013-09-04 | 金欧米茄公司 | Omega-3 concentrate |
| CN109438227A (en) * | 2018-04-27 | 2019-03-08 | 南京健友生化制药股份有限公司 | A kind of production method of ω -3 polyene fatty acid ethylester |
| CN114057574A (en) * | 2021-12-03 | 2022-02-18 | 浙江工商大学 | Method for preparing high-purity EPA ethyl ester |
-
1997
- 1997-07-02 CN CN 97108136 patent/CN1204638A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101213281B (en) * | 2005-05-04 | 2013-03-13 | 普罗诺瓦生物医药挪威公司 | New dha derivatives and their use as medicaments |
| CN101796014A (en) * | 2007-06-29 | 2010-08-04 | 马泰克生物科学公司 | Production and purification of esters of polyunsaturated fatty acids |
| CN102448314A (en) * | 2009-06-02 | 2012-05-09 | 金欧米茄公司 | Method for producing a concentrate of eicosapentaenoic and docosahexaenoic acid esters |
| CN102448314B (en) * | 2009-06-02 | 2013-10-23 | 金欧米茄公司 | Method for producing concentrate of eicosapentaenoic and docosahexaenoic acid esters |
| US8981137B2 (en) | 2009-06-02 | 2015-03-17 | Golden Omega S.A. | Method for producing a concentrate of eicosapentaenoic and docosahexaenoic acids |
| CN103281910A (en) * | 2010-12-27 | 2013-09-04 | 金欧米茄公司 | Omega-3 concentrate |
| CN103281910B (en) * | 2010-12-27 | 2015-04-15 | 金欧米茄公司 | Omega-3 concentrate |
| CN109438227A (en) * | 2018-04-27 | 2019-03-08 | 南京健友生化制药股份有限公司 | A kind of production method of ω -3 polyene fatty acid ethylester |
| CN109438227B (en) * | 2018-04-27 | 2021-10-12 | 南京健友生化制药股份有限公司 | Production method of omega-3 polyenoic fatty acid ethyl ester |
| CN114057574A (en) * | 2021-12-03 | 2022-02-18 | 浙江工商大学 | Method for preparing high-purity EPA ethyl ester |
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