CN101736044B - Method for continuous enzymatic synthesis of n-3PUFA glyceride - Google Patents
Method for continuous enzymatic synthesis of n-3PUFA glyceride Download PDFInfo
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- CN101736044B CN101736044B CN 200810162265 CN200810162265A CN101736044B CN 101736044 B CN101736044 B CN 101736044B CN 200810162265 CN200810162265 CN 200810162265 CN 200810162265 A CN200810162265 A CN 200810162265A CN 101736044 B CN101736044 B CN 101736044B
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- dha
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- 238000000034 method Methods 0.000 title claims abstract description 21
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 16
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 10
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 25
- 108090000790 Enzymes Proteins 0.000 claims abstract description 18
- 102000004190 Enzymes Human genes 0.000 claims abstract description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 235000021323 fish oil Nutrition 0.000 claims abstract description 14
- 239000002808 molecular sieve Substances 0.000 claims abstract description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000032050 esterification Effects 0.000 claims description 16
- 238000005886 esterification reaction Methods 0.000 claims description 16
- 229910001220 stainless steel Inorganic materials 0.000 claims description 14
- 239000010935 stainless steel Substances 0.000 claims description 14
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 11
- 238000006555 catalytic reaction Methods 0.000 claims description 10
- 235000011187 glycerol Nutrition 0.000 claims description 8
- 108010084311 Novozyme 435 Proteins 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000010923 batch production Methods 0.000 abstract description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 3
- 102000004882 Lipase Human genes 0.000 abstract 1
- 108090001060 Lipase Proteins 0.000 abstract 1
- 239000004367 Lipase Substances 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000019421 lipase Nutrition 0.000 abstract 1
- 238000005086 pumping Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 10
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 7
- 125000005908 glyceryl ester group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- -1 glycerin ester Chemical class 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention relates to a method for continuous enzymatic synthesis of n-3PUFA glyceride, comprising the following steps: preparing fish oil n-3PUFA (EPA, DHA) and glycerol into reaction liquid according to a certain proportion; then pumping reaction liquid into an enzyme reaction column provided with immobilized lipase through a constant current pump for carrying out reaction for enzymatic synthesis of n-3PUFA; finally realizing continuous enzymatic synthetic production of n-3PUFA by controlling circulation flow velocity of the reaction liquid in the reactor and setting a molecular sieve dehydrater in the reaction system. The n-3PUFA glyceride product prepared by the continuous syhthesis method features an ester yield of 30-50%, a monoester content of 20-30%, a diester content of 50-70%and a trig content of 10-20%. With the method of the invention adopted, recycle of enzyme can be realized, cost can be greatly reduced, production cycle can be shortened, production efficiency can beimproved and the operation is easy, so that the method is of great practical value to industrialized batch production.
Description
(1) technical field
The present invention relates to relate to a kind of method of continuous enzymatic synthesis of n-3 PUFA glyceride.
(2) background technology
Fish oil n-3 polyunsaturated fatty acid (n-3PUFA)---EPA and DHA has important medical treatment and functional health effect to human body, n-3PUFA glyceryl ester is as its natural existence form, have stable in properties, be difficult for oxidation, mouthfeel is good, the most suitable human body such as digests and assimilates at the characteristics, becomes the best product pattern of EPA, DHA fish oil healthcare products and medicine.
Because EPA and DHA glyceride content relatively low (20～30%) in the natural fish oil, its medical treatment and health-care effect are unsatisfactory.In order to improve EPA and DHA glyceride content, people successively once adopted Physical, chemical method and enzyme process to carry out the enrichment of EPA and DHA glyceryl ester, at present, utilized the enriching method of lipase-catalyzed synthesis DHA and EPA glyceryl ester further to be subject to people's attention.Compare with the physics and chemistry method, it is high that enzyme process has a catalytic efficiency, usage quantity seldom, the advantage such as reaction conditions is gentle, and concentration effect is good.Patent CN101161819A (a kind of method of preparing n-3 PUFA ocean glycerin ester by enzymatical process) utilizes this method can prepare EPA and the DHA total content reaches 50～80% glyceryl ester, wherein diglyceride content 50～60%, content of triglyceride 30～35%, monoglyceride content 15～20%.
But; no matter be that physical enrichment method, chemical synthesis or enzyme catalysis synthesis method all belong to the batch production pattern; intermittent reaction is only applicable to short run, the slow reaction process of speed of reaction, can't realize the serialization building-up reactions, is not suitable for industrial scale production.Particularly in enzyme-catalyzed reaction, because the accumulation of product can produce certain inhibition to enzymatic reaction, thereby affected the balance of reacting, the forward that has hindered enzymic catalytic reaction carries out.In addition, for intermittent reaction, grow reaction time (24～48h), production efficiency is low, the recycling complex operation of enzyme, and production cost is high, has limited its application in industrialization.
(3) summary of the invention
Technical problem to be solved by this invention is to provide a kind of continuously synthetic n-3PUFA glyceryl ester, improve the method for continuous enzymatic synthesis of n-3 PUFA glyceride of the esterification yield of EPA, DHA glyceryl ester.
A kind of method of continuous enzymatic synthesis of n-3 PUFA glyceride, the method may further comprise the steps:
(1) with fish oil n-3PUFA---EPA and DHA respectively with glycerine in molar ratio the ratio of 2～4:1 be made into reaction solution, reaction solvent is Isosorbide-5-Nitrae-dioxane, reaction solution mixes, and is preheated to 35～50 ℃ of the temperature of setting;
(2) by constant flow pump the reaction solution that mixes is at the uniform velocity pumped into and carry out enzyme catalysis synthetic glyceride reaction in the enzyme reaction post that is filled with immobilized lipase Novozym435;
(3) reaction solution through esterification dewaters by the container with mealy molecular sieve;
(4) repeatedly esterification and dehydrating step, behind continuous reaction 1～4h, collecting reaction product obtains EPA, DHA glyceride product.
Preferably, the flow rate control of described reaction solution in the enzyme reaction post is at 0.1～1mL/min.
Preferably, the temperature of described enzyme reaction post is controlled at 35～50 ℃.
Preferably, described fish oil n-3PUFA---the purity of EPA and DHA is 93～95%.
Preferably, described enzyme reaction post is stainless steel column, and the container with mealy molecular sieve is stainless steel column.
Preferably, the esterification yield of the EPA in the described n-3PUFA glyceryl ester, DHA glyceryl ester all reaches 30～50%, EPA, DHA monoglyceride content is that 20～30%, EPA, DHA diglyceride content are that 50～70%, EPA, DHA content of triglyceride are 10～20%.
Beneficial effect of the present invention is:
The present invention has realized that the serialization enrichment of fish oil EPA, DHA glyceride product produces, and can realize the recycling of enzyme, greatly reduces cost, shortens the production cycle, enhance productivity, and easily operation, production has good actual application value to industrial scale.
(4) embodiment
The invention will be further described below in conjunction with embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1
Immobilized lipase Novozym435 is filled in the enzyme reaction post, the enzyme reaction post is stainless steel column, place thermostat container to control temperature 45 C, then with fish oil n-3PUFA---EPA and DHA respectively with glycerine in molar ratio the ratio of 2:1 be made into reaction solution, reaction solution mixes, and is preheated to 45 ℃.By constant flow pump the reaction solution that mixes is pumped into and to carry out enzyme catalysis synthetic glyceride reaction in the enzyme reaction post, the moisture that esterification generates removes by the stainless steel column that the finely powdered molecular sieve is housed, carry out the iterative cycles reaction in the feeding bottle of the reacted feed liquid access of enzyme post reaction cartridge liquid, control constant flow pump flow velocity is 0.1mL/min, in reactor behind the continuous reaction 4h, collecting reaction product, obtain EPA, the DHA glyceride product, EPA, the esterification yield of DHA glyceryl ester is respectively 48% and 46%, EPA, DHA monoglyceride content is respectively 22% and 24%, EPA, the DHA diglyceride content is respectively 64% and 65%, EPA, the DHA content of triglyceride is respectively 14 and 11%.
Embodiment 2
Immobilized lipase Novozym435 is filled in the enzyme reaction post, the enzyme reaction post is stainless steel column, place thermostat container to control temperature 45 C, then with fish oil n-3PUFA---EPA and DHA respectively with glycerine in molar ratio the ratio of 3:1 be made into reaction solution, reaction solution mixes, and is preheated to 45 ℃.By constant flow pump the reaction solution that mixes is pumped into and to carry out enzyme catalysis synthetic glyceride reaction in the enzyme reaction post, the moisture that esterification generates removes by the stainless steel column that the finely powdered molecular sieve is housed, carry out the iterative cycles reaction in the feeding bottle of the reacted feed liquid access of enzyme post reaction cartridge liquid, control constant flow pump flow velocity is 0.5mL/min, in reactor behind the continuous reaction 2h, collecting reaction product, obtain EPA, the DHA glyceride product, EPA, the esterification yield of DHA glyceryl ester is respectively 45% and 43%, EPA, DHA monoglyceride content is respectively 20% and 22%, EPA, the DHA diglyceride content is respectively 65% and 66%, EPA, the DHA content of triglyceride is respectively 15 and 12%.
Embodiment 3
Immobilized lipase Novozym435 is filled in the enzyme reaction post, the enzyme reaction post is stainless steel column, place thermostat container to control temperature 50 C, then with fish oil n-3PUFA---EPA and DHA respectively with glycerine in molar ratio the ratio of 3:1 be made into reaction solution, reaction solution mixes, and is preheated to 50 ℃.By constant flow pump the reaction solution that mixes is pumped into and to carry out enzyme catalysis synthetic glyceride reaction in the enzyme reaction post, the moisture that esterification generates removes by the stainless steel column that the finely powdered molecular sieve is housed, carry out the iterative cycles reaction in the feeding bottle of the reacted feed liquid access of enzyme post reaction cartridge liquid, control constant flow pump flow velocity is 0.5mL/min, in reactor behind the continuous reaction 3h, collecting reaction product, obtain EPA, the DHA glyceride product, EPA, the esterification yield of DHA glyceryl ester is respectively 43% and 42%, EPA, DHA monoglyceride content is respectively 28% and 30%, EPA, the DHA diglyceride content is respectively 60% and 60%, EPA, the DHA content of triglyceride is respectively 12 and 10%.
Embodiment 4
Immobilized lipase Novozym435 is filled in the enzyme reaction post, the enzyme reaction post is stainless steel column, place 35 ℃ of thermostat container control temperature, then with fish oil n-3PUFA---EPA and DHA respectively with glycerine in molar ratio the ratio of 4:1 be made into reaction solution, reaction solution mixes, and is preheated to 35 ℃.By constant flow pump the reaction solution that mixes is pumped into and to carry out enzyme catalysis synthetic glyceride reaction in the enzyme reaction post, the moisture that esterification generates removes by the stainless steel column that the finely powdered molecular sieve is housed, carry out the iterative cycles reaction in the feeding bottle of the reacted feed liquid access of enzyme post reaction cartridge liquid, control constant flow pump flow velocity is 1mL/min, in reactor behind the continuous reaction 2h, collecting reaction product, obtain EPA, the DHA glyceride product, EPA, the esterification yield of DHA glyceryl ester is respectively 36% and 33%, EPA, DHA monoglyceride content is respectively 29% and 30%, EPA, the DHA diglyceride content is respectively 53% and 57%, EPA, the DHA content of triglyceride is respectively 18 and 13%.
Embodiment 5
Immobilized lipase Novozym435 is filled in the enzyme reaction post, the enzyme reaction post is stainless steel column, place thermostat container to control temperature 50 C, then with fish oil n-3PUFA---EPA and DHA respectively with glycerine in molar ratio the ratio of 4:1 be made into reaction solution, reaction solution mixes, and is preheated to 50 ℃.By constant flow pump the reaction solution that mixes is pumped into and to carry out enzyme catalysis synthetic glyceride reaction in the enzyme reaction post, the moisture that esterification generates removes by the stainless steel column that the finely powdered molecular sieve is housed, carry out the iterative cycles reaction in the feeding bottle of the reacted feed liquid access of enzyme post reaction cartridge liquid, control constant flow pump flow velocity is 1mL/min, in reactor behind the continuous reaction 1h, collecting reaction product, obtain EPA, the DHA glyceride product, EPA, the esterification yield of DHA glyceryl ester is respectively 41% and 40%, EPA, DHA monoglyceride content is respectively 21% and 23%, EPA, the DHA diglyceride content is respectively 68% and 67%, EPA, the DHA content of triglyceride is respectively 11 and 10%.
Claims (2)
1. the method for a continuous enzymatic synthesis of n-3 PUFA glyceride is characterized in that the method may further comprise the steps:
(1) with fish oil n-3PUFA---EPA and DHA respectively with glycerine in molar ratio 2～4: 1 ratio be made into reaction solution, reaction solvent is Isosorbide-5-Nitrae-dioxane, reaction solution mixes, and is preheated to 35～50 ℃ of the temperature of setting;
(2) by constant flow pump the reaction solution that mixes is at the uniform velocity pumped into and carry out enzyme catalysis synthetic glyceride reaction in the enzyme reaction post that is filled with immobilized lipase Novozym435;
(3) reaction solution through esterification dewaters by the container with mealy molecular sieve;
(4) repeatedly esterification and dehydrating step, behind continuous reaction 1～4h, collecting reaction product obtains EPA, DHA glyceride product;
The flow rate control of described reaction solution in the enzyme reaction post is at 0.1～1mL/min;
The temperature of described enzyme reaction post is controlled at 35～50 ℃;
Described fish oil n-3PUFA---the purity of EPA and DHA is 93～95%.
2. the method for described continuous enzymatic synthesis of n-3 PUFA glyceride according to claim 1 is characterized in that described enzyme reaction post is stainless steel column, and the container with mealy molecular sieve is stainless steel column.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200810162265 CN101736044B (en) | 2008-11-18 | 2008-11-18 | Method for continuous enzymatic synthesis of n-3PUFA glyceride |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200810162265 CN101736044B (en) | 2008-11-18 | 2008-11-18 | Method for continuous enzymatic synthesis of n-3PUFA glyceride |
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| CN101736044A CN101736044A (en) | 2010-06-16 |
| CN101736044B true CN101736044B (en) | 2013-10-23 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10030212B2 (en) | 2014-10-13 | 2018-07-24 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Method for preparing glyceride type polyunsaturated fatty acids |
| FR3118967A1 (en) * | 2021-01-19 | 2022-07-22 | Polaris | Composition of microorganism oil enriched with DHA or EPA diglycerides |
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| CN102028711B (en) * | 2010-12-27 | 2013-02-20 | 河北康睿达脂质有限公司 | Enzymatically synthesized triglyceride type fish oil soft capsules and preparation method thereof |
| CN102994580B (en) * | 2012-11-30 | 2014-06-11 | 华南理工大学 | Preparation method of high-purity triglyceride type PUFA (Polyunsaturated Fatty Acid) |
| CN103243126A (en) * | 2013-05-25 | 2013-08-14 | 湖北佳富实业有限公司 | Preparation method of diacylglycerol |
| CN104509600A (en) * | 2013-09-29 | 2015-04-15 | 中粮营养健康研究院有限公司 | Blend edible oil with reinforced n-3 polyunsaturated fatty acids |
| CA2987613C (en) * | 2015-06-01 | 2023-03-28 | Cargill, Incorporated | Oil composition with mono-acylglycerides |
| CN105420300B (en) * | 2015-12-09 | 2018-11-02 | 华南理工大学 | A kind of preparation method of glycerine ester type PUFA |
| US11466231B2 (en) | 2018-06-05 | 2022-10-11 | Dsm Ip Assets B.V. | Process for the production of diglycerides |
| CN112501217A (en) * | 2021-02-04 | 2021-03-16 | 天津凯莱英制药有限公司 | Continuous preparation method of S- (+) -2, 2-dimethylcyclopropane carboxylic acid |
| CN114736739B (en) * | 2022-03-21 | 2023-08-25 | 中国农业科学院油料作物研究所 | Method for synchronously preparing deacidification and functional lipid by using oil enzymatic method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101161819A (en) * | 2007-10-12 | 2008-04-16 | 广东海洋大学 | Method for preparing n-3PUFA ocean glycerin ester by enzymatical process |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2685272A1 (en) * | 2007-04-26 | 2008-11-06 | Patrick Adlercreutz | A polyunsaturated fatty acid (pufa) enriched marine oil comprising eicosapentaenoic acid (epa) and docosahexaenoic acid (dha), and a process of production thereof |
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2008
- 2008-11-18 CN CN 200810162265 patent/CN101736044B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101161819A (en) * | 2007-10-12 | 2008-04-16 | 广东海洋大学 | Method for preparing n-3PUFA ocean glycerin ester by enzymatical process |
Non-Patent Citations (4)
| Title |
|---|
| Lipase-catalyzed esterification of glycerol and polyunsaturated fatty acids from fish and microalgae oils;Medina AR et al;《Journal of Biotechnology》;19991231;第70卷(第1-3期);379-391 * |
| Medina AR et al.Lipase-catalyzed esterification of glycerol and polyunsaturated fatty acids from fish and microalgae oils.《Journal of Biotechnology》.1999,第70卷(第1-3期),379-391. |
| 曾远平等.鱼油中EPA和DHA的富集方法及研究进展.《现代食品科技》.2006,第22卷(第1期),160-163. |
| 鱼油中EPA和DHA的富集方法及研究进展;曾远平等;《现代食品科技》;20061231;第22卷(第1期);160-163 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10030212B2 (en) | 2014-10-13 | 2018-07-24 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Method for preparing glyceride type polyunsaturated fatty acids |
| FR3118967A1 (en) * | 2021-01-19 | 2022-07-22 | Polaris | Composition of microorganism oil enriched with DHA or EPA diglycerides |
| WO2022157147A1 (en) * | 2021-01-19 | 2022-07-28 | Polaris | Composition of oil of microorganisms enriched with dha or epa diglycerides |
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Effective date of registration: 20190709 Address after: 316000 Building A, Xingye Road, Ganlang Town, Dinghai District, Zhoushan City, Zhejiang Province Patentee after: ZHOUSHAN SINOMEGA BIOTECH ENGINEERING CO., LTD. Address before: No. 105, Dinghai Cultural Road, Zhoushan, Zhejiang Province Patentee before: Zhejiang Ocean University |