CN101979625A - Method for synthesizing triglyceride with medium/long-chain structure by catalyzing ester exchange through enzyme - Google Patents
Method for synthesizing triglyceride with medium/long-chain structure by catalyzing ester exchange through enzyme Download PDFInfo
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- CN101979625A CN101979625A CN 201010529356 CN201010529356A CN101979625A CN 101979625 A CN101979625 A CN 101979625A CN 201010529356 CN201010529356 CN 201010529356 CN 201010529356 A CN201010529356 A CN 201010529356A CN 101979625 A CN101979625 A CN 101979625A
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Abstract
The invention discloses a method for synthesizing triglyceride with a medium/long-chain structure by catalyzing ester exchange through enzyme, and belongs to the technical field of deep processing and modification of oil. Medium-chain triglyceride (MCT) and long-chain triglyceride (LCT) are taken as raw materials, lipase TLIM is adopted to catalyze ester exchange reaction, and under the condition of stirring, the optimal process and parameters for synthesizing the triglyceride with the medium/long-chain structure are determined by optimizing influencing factors such as reaction temperature, reaction time, lipase adding amount and the like.
Description
Technical field
The present invention be a kind of enzyme process catalytic transesterification synthetic in/method of backbone triglyceride level, belong to grease deep processing, modification technology field.
Background technology
In/the backbone triglyceride level (in/long-chain STG) be by esterification or a kind of novel texture triglyceride level of transesterify mode synthetic, be characterized in containing simultaneously on the glycerol backbone medium chain fatty acid (MCFA, the lipid acid of 8～12 carbon) and longer chain fatty acid (LCFA, the lipid acid of 14～22 carbon).In/long chain triglycerides (LCT), medium chain triglyceride (MCT) and physical mixed that long-chain STG is more traditional in/long chain triglycerides (MCT/LCT) has many advantages aspect Nutrition and Metabolism, day by day all increase in food, pharmaceutical industries application demand, especially the application in lipomul.Studies show that, LCT type lipomul exists the defective of some metabolism and immunologic function aspect, though MCT has and does not rely on carnitine transhipment and can directly enter plastosome, hydrolysis in vivo, oxidation, removing speed be fast, be difficult in liver and peripheral tissues in advantage such as soak into, but MCT does not contain indispensable fatty acid.By contrast, the MCT/LCT of physical mixed contains two kinds of different lipids, can remedy the deficiency of single form lipomul on energy supply and nutritive property to a certain extent, and still, the metabolism between the different triglyceride level can produce interference to a certain extent.
In/long-chain STG has oxidation faster, hydrolysis release and plasma clearance than the MCT/LCT of LCT and physical mixed, better saves the nitrogen effect, has advantages such as not influencing body reticuloendothelial system function simultaneously.Abroad, in/long-chain STG type high-fat emulsion has been widely used in the clinical nutrition support; And at home, in widely used main still long chain triglycerides (LCT) type and the physical mixed/long chain triglycerides (MCT/LCT) type lipomul.In/though long-chain STG type high-fat emulsion has product on sale, yet, in its main raw material/long-chain STG is from external import, have the technical information such as production method, technology of the Central Shanxi Plain/long-chain STG that China is maintained complete secrecy, in the research therefore ,/synthetic method of long-chain STG has great importance.
Enzyme process composite structure ester byproduct of reaction is less, can not produce soap, is easy to purifying, and the waste liquid of generation is few.Along with development of biology such as genes, the price of lipase will be more and more lower, in the enzyme process preparation/and the suitability for industrialized production of long-chain STG has fine prospect.
Summary of the invention
The purpose of this invention is to provide a kind of enzyme process catalytic transesterification synthetic in/method of backbone triglyceride level.
Technical scheme of the present invention:
It is raw material that the present invention adopts medium chain triglyceride (MCT), long chain triglycerides (LCT), with lipase TL IM is catalyzer (letter (China) Bioisystech Co., Ltd of Novi), heating, carry out under the stirring condition enzyme process transesterify synthetic in/long-chain STG, with in the ester exchange offspring/long-chain STG content is leading indicator, by the optimization of factors such as temperature of reaction, time, enzyme addition, in determining/the best synthesis technique of long-chain STG.
1, temperature of reaction
Temperature controlling is extremely important in the reaction, because enzymic catalytic reaction is a thermodynamic process, affects the catalytic activity of enzyme, the dissolved state of substrate and the mass transfer velocity of viscosity, substrate and product etc.Temperature is too low, is unfavorable for reaching the required activation energy of reaction, and lipase can not effectively combine with substrate (triglyceride level), and speed of reaction is lower, the reaction times prolongation, in the product in/long-chain STG is less; Temperature is too high, then can cause the lipase sex change, reduces enzyme and lives.
2, the reaction times
Transesterification reaction comprises that catalyzer inserts, forms intermediate, the access of another lipid acid and the disconnection four-stage of catalyzer, whole process need regular hour.Deficiency of time, then this reaction process also can't reach balance, and overlong time in then not only being unprofitable to/increase of backbone content of triglyceride, also can increase the degree of side reaction on the contrary, is unfavorable for the quality of product.
3, lipase addition
The size and the speed of response of enzyme concentration are directly related, and be big if the amount of substrate can keep enough, and speed of response also meets kinetics relation with the enzyme amount, and when the enzyme amount increased, speed of response is increase thereupon also.The lipase addition then reduces speed of reaction very little.The lipase addition is too much, when just substrate content was relatively low, though at this moment speed of response is also along with increase, the influence of the resistance to mass transfer of substrate and product had begun the influence greater than enzyme reaction catalysis speed, the increment of its speed of response reduces, and the catalytic efficiency of enzyme reduces.
During a kind of enzyme process catalytic transesterification is synthetic/method of backbone triglyceride level, take by weighing a certain amount of medium chain triglyceride MCT and long chain triglycerides LCT, in MCT ︰ LCT mol ratio is that the ratio of 1 ︰ 0.5 ~ 2 joins it in airtight reaction vessel after drying, under the condition of stirring, 50-90 ℃ heating, the lipase TL IM that adds the heavy 2%-12% of the total oil of MCT and LCT carries out transesterification reaction as catalyzer, stop heating behind the reaction 30-180min, through centrifugal, separating out fat enzyme and oil, in getting/the backbone triglyceride level.
Medium chain triglyceride MCT selects hot Triglyceride DDD for use, and long chain triglycerides LCT selects soybean oil for use.
In/long-chain STG Determination on content:
Evaporat light scattering-high performance liquid chromatography (HPLC-ELSD)
In/mensuration of long-chain STG acid number:
Mensuration (volumetry) with reference to GB GB/T 5530-2005 animal-plant oil acid number and acidity
In/mensuration of long-chain STG peroxide value:
Measure with reference to GB GBT5538-2005 animal-plant oil peroxide value
In/mensuration of long-chain STG color and luster:
Mensuration with reference to GB GB/T 22460-2008 animal-plant oil Lovibond color and luster
In/quality of long-chain STG
Triglyceride level composition, acid number, peroxide value and color and luster to ester exchange offspring detect, and the result shows, in the product in/long-chain STG content can reach between the 70%-80%, MCT content is between 5%-15%, LCT content is between 10%-20%; Acid number is between 4 ~ 20mg/g; Peroxide value is at 0.1-0.6meq/kg; Between the yellow value of the color and luster 0.5-3, between the red value 0-0.3 (1 inch cuvette of Lovibond).
Beneficial effect of the present invention: the present invention set up a kind of enzyme process synthetic in/method of long-chain STG, belong to pioneering research.
In providing/and the selection foundation of long-chain STG synthesis technologic parameter, determined in the high-content/concrete technology of long-chain STG synthetic and parameter.
Adopt this technology synthetic in/long-chain STG, compare with common chemical synthesis method in the present industrial production, safer, environmental protection and side reaction are few.
Embodiment
Embodiment 1
6.4g long carbochain triglyceride level (soybean oil) mixes (promptly long carbochain triglyceride level and middle chain triglyceride mol ratio 1 ︰ 1) with 3.6g middle chain triglyceride (hot Triglyceride DDD), join in the encloses container, under mechanical stirring, 70 ℃ of heating conditions, adding 4%(with elaeometer) lipase TL IM picks up counting, stop heating behind the reaction 60min, oil is changed in the centrifuge tube over to the centrifugal 2min of 4000r/min, with lipase and separating of oil, in getting/long-chain STG.In measuring in the product/long-chain STG content and acid value, peroxide value and color and luster.
In detecting in the products therefrom/content of long-chain STG is 72.73%, acid value 10.8mg/g, peroxide value 0.39meq/kg, color and luster be yellow value 1.0, red value 0.1(1 inch cuvette).
Embodiment 2
6.4g long carbochain triglyceride level (soybean oil) mixes (promptly long carbochain triglyceride level and middle chain triglyceride mol ratio 1 ︰ 1) with 3.6g middle chain triglyceride (hot Triglyceride DDD), join in the encloses container, under mechanical stirring, 80 ℃ of heating conditions, adding 4%(with elaeometer) lipase TL IM picks up counting, stop heating behind the reaction 60min, oil is changed in the centrifuge tube over to the centrifugal 2min of 4000r/min, with lipase and separating of oil, in getting/long-chain STG.In measuring in the product/long-chain STG content and acid value, peroxide value and color and luster.
In detecting in the products therefrom/content of long-chain STG is 73.45%, acid value 8.13mg/g, peroxide value 0.43meq/kg, color and luster be yellow value 1.0, red value 0.1(1 inch cuvette)
Embodiment 3
6.4g long carbochain triglyceride level (soybean oil) mixes (promptly long carbochain triglyceride level and middle chain triglyceride mol ratio are 1 ︰ 1) with 3.6g middle chain triglyceride (hot Triglyceride DDD), join in the encloses container, under mechanical stirring, 70 ℃ of heating conditions, adding 10%(with elaeometer) lipase TL IM picks up counting, stop heating behind the reaction 180min, oil is changed in the centrifuge tube over to the centrifugal 2min of 4000r/min, with lipase and separating of oil, in getting/long-chain STG.In measuring in the product/long-chain STG content and acid value, peroxide value and color and luster.
In detecting in the products therefrom/content of long-chain STG is 77.14%, acid value 18.55mg/g, peroxide value 0.50meq/kg, color and luster be yellow value 1.0, red value 0.1(1 inch cuvette).
Claims (2)
- An enzyme process catalytic transesterification synthetic in/method of backbone triglyceride level, it is characterized in that taking by weighing a certain amount of medium chain triglyceride MCT and long chain triglycerides LCT, in MCT ︰ LCT mol ratio is that the ratio of 1 ︰ 0.5 ~ 2 joins it in airtight reaction vessel after drying, under the condition of stirring, 50-90 ℃ heating, the lipase TL IM that adds the heavy 2%-12% of the total oil of MCT and LCT carries out transesterification reaction as catalyzer, stop heating behind the reaction 30-180min, through centrifugal, separating out fat enzyme and oil, in getting/the backbone triglyceride level.
- According to claims 1 described enzyme process synthetic in/method of backbone triglyceride level, it is characterized in that medium chain triglyceride MCT selects hot Triglyceride DDD for use, long chain triglycerides LCT selects soybean oil for use.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102140390A (en) * | 2011-03-07 | 2011-08-03 | 四川国瑞药业有限责任公司 | Synthesis method of medium/long-chain triglyceride |
| CN103897811A (en) * | 2014-04-02 | 2014-07-02 | 河北康睿达脂质有限公司 | Production method for medium-chain and long-chain oil fatty acid |
| CN104642570A (en) * | 2015-03-11 | 2015-05-27 | 重庆第二师范学院 | Modification preparation method of maize germ oil |
| CN105087694A (en) * | 2015-08-28 | 2015-11-25 | 暨南大学 | Method for preparing medium- and long-chain triglyceride by virtue of packed bed reactor |
| CN105779517A (en) * | 2014-12-22 | 2016-07-20 | 丰益(上海)生物技术研发中心有限公司 | Method for reducing content of diglyceride in enzymic-method esterification deacidification process |
| CN105821089A (en) * | 2016-06-12 | 2016-08-03 | 江南大学 | Method for enzymatically synthesizing medium-long chain structure triglyceride |
| CN109907126A (en) * | 2019-04-18 | 2019-06-21 | 江南大学 | A kind of fat or oil composition and preparation method thereof of middle Long carbon chain triglycerides |
| CN111040882A (en) * | 2019-11-25 | 2020-04-21 | 江南大学 | Preparation method of medium-long carbon chain triglyceride based on modeling calculation |
| CN112538505A (en) * | 2020-12-08 | 2021-03-23 | 华南理工大学 | Technology for enzymatic transesterification |
| CN113073122A (en) * | 2021-04-29 | 2021-07-06 | 江南大学 | Method for preparing hot pot seasoning oil rich in medium-long carbon chain triglyceride by enzyme method |
| CN113774094A (en) * | 2021-09-23 | 2021-12-10 | 江南大学 | Enzymatic synthesis method of medium-long chain triglyceride |
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| CN1688704A (en) * | 2002-09-13 | 2005-10-26 | 三得利株式会社 | Process for production of transesterified oils/fats or triglycerides |
| CN1816614A (en) * | 2003-07-09 | 2006-08-09 | 日清奥利友集团株式会社 | Process for producing symmetrical triglyceride |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102140390A (en) * | 2011-03-07 | 2011-08-03 | 四川国瑞药业有限责任公司 | Synthesis method of medium/long-chain triglyceride |
| CN102140390B (en) * | 2011-03-07 | 2012-11-14 | 四川国瑞药业有限责任公司 | Synthesis method of medium/long-chain triglyceride |
| CN103897811A (en) * | 2014-04-02 | 2014-07-02 | 河北康睿达脂质有限公司 | Production method for medium-chain and long-chain oil fatty acid |
| CN105779517B (en) * | 2014-12-22 | 2019-10-29 | 武汉轻工大学 | The method of diacylglycerol content during reduction enzyme process esterification deacidification |
| CN105779517A (en) * | 2014-12-22 | 2016-07-20 | 丰益(上海)生物技术研发中心有限公司 | Method for reducing content of diglyceride in enzymic-method esterification deacidification process |
| CN104642570A (en) * | 2015-03-11 | 2015-05-27 | 重庆第二师范学院 | Modification preparation method of maize germ oil |
| US20180245111A1 (en) * | 2015-08-28 | 2018-08-30 | Jinan University | Method for Preparing Medium-Long-Chain Triglyceride Using Packed Bed Reactor |
| WO2017036122A1 (en) * | 2015-08-28 | 2017-03-09 | 暨南大学 | Method of manufacturing medium- and long-chain triglyceride by using packed bed reactor |
| CN105087694B (en) * | 2015-08-28 | 2019-02-12 | 暨南大学 | A method of using packed bed reactor prepare in long chain triglycerides |
| CN105087694A (en) * | 2015-08-28 | 2015-11-25 | 暨南大学 | Method for preparing medium- and long-chain triglyceride by virtue of packed bed reactor |
| CN105821089A (en) * | 2016-06-12 | 2016-08-03 | 江南大学 | Method for enzymatically synthesizing medium-long chain structure triglyceride |
| CN109907126A (en) * | 2019-04-18 | 2019-06-21 | 江南大学 | A kind of fat or oil composition and preparation method thereof of middle Long carbon chain triglycerides |
| CN109907126B (en) * | 2019-04-18 | 2021-09-07 | 江南大学 | Grease composition of medium-long carbon chain triglyceride and preparation method thereof |
| CN111040882A (en) * | 2019-11-25 | 2020-04-21 | 江南大学 | Preparation method of medium-long carbon chain triglyceride based on modeling calculation |
| CN112538505A (en) * | 2020-12-08 | 2021-03-23 | 华南理工大学 | Technology for enzymatic transesterification |
| CN113073122A (en) * | 2021-04-29 | 2021-07-06 | 江南大学 | Method for preparing hot pot seasoning oil rich in medium-long carbon chain triglyceride by enzyme method |
| CN113774094A (en) * | 2021-09-23 | 2021-12-10 | 江南大学 | Enzymatic synthesis method of medium-long chain triglyceride |
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Address after: 214016 Jiangsu city of Wuxi Province District Liangxi No. 898 South Road 7 layer beam Creek area of food science and Technology Park Patentee after: Jiangnan University Address before: Food College of Jiangnan University No. 1800 Li Lake Avenue 214122 in Jiangsu province Wuxi City Binhu District Patentee before: Jiangnan University |
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Effective date of registration: 20200825 Address after: Room 101-6, building 3, No. 99, Qingshu Road, Wuxi Economic Development Zone, Jiangsu Province, 214072 Patentee after: Wuxi Yiyu Technology Development Co., Ltd Address before: 214016 Jiangsu city of Wuxi Province District Liangxi No. 898 South Road 7 layer beam Creek area of food science and Technology Park Patentee before: Jiangnan University |