CN105821089A - Method for enzymatically synthesizing medium-long chain structure triglyceride - Google Patents
Method for enzymatically synthesizing medium-long chain structure triglyceride Download PDFInfo
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Abstract
The invention discloses a method for enzymatically synthesizing medium-long chain structure triglyceride. Long-chain triglyceride and medium-chain triglyceride are mixed according to a certain mass ratio, lipase is added in a solvent-free system, stirring and reacting are carried out for a period of time at certain temperature, a transesterification reaction is carried out, and a product containing medium-long chain structure triglyceride is obtained. The method for enzymatically synthesizing medium-long chain structure triglyceride is high in reaction speed, high in conversion rate and mild in reaction condition, is efficient and fast, meets green chemistry and is huge in application potential, and large-scale industrial popularization is convenient.
Description
Technical field
The invention belongs to oil synthesis technical field, be specifically related to a kind of method of backbone triglyceride in enzymatic clarification.
Background technology
Middle backbone triglyceride (MLCT) is the structured triglyceride synthesized by esterification or ester exchange mode, contains medium-chain fatty acid and Long carbon chain fatty acid in the fatty acid that its glycerol backbone connects simultaneously.Wherein, medium-chain fatty acid refers to the carbon number fatty acid from C6～C12, mostlys come from Petiolus Trachycarpi oil, Oleum Cocois, and it has the digest supersession characteristic of uniqueness: is directly entered blood by portal vein in vivo, can hydrolyze faster and absorb；Will not accumulate in fatty tissue storage and liver；The ketoboidies material that metabolism generates has facilitation to body's immunity；Do not rely on carnitine direct inlet wire plastochondria and carry out oxidation Decomposition；Transhipment need not albuminous participation in vivo.But medium-chain fatty acid is not required fatty acid, ketoboidies excess can be caused to be poisoned after a large amount of absorptions, it is impossible to replace Long carbon chain fatty acid.MLCT can realize the synchronization transport of fatty acid, can be discharged in blood at a more controllable hydrolysis rate by medium-chain fatty acid, alleviate the toxicity of medium-chain fatty acid；Essential fatty acid can not only be provided, and can improve Long carbon chain fatty acid is absorbed.MLCT has quick energy supply, reduces the feature of Fat Accumulation, beneficially body weight control, has smoke point low, excellent frying characteristics the most easy to foaming simultaneously.At present, MLCT is widely used in the industry such as pharmacy, food.
Its preparation method generally has following several approach:
(1) chemical method synthesis.
Chemically catalyzed interesterification refers generally to carry out under using alkali metal, alkali metal hydroxide etc. as catalyst, and its advantage is cheap, technical maturity, can realize large-scale production.But it is high that chemical method exists reaction temperature, randomness is strong, and specificity is weak, and product is difficult to control to, thus required fatty acid can not be attached to the shortcoming on the specific position of triglyceride.
(2) direct esterification
Direct esterification refers to that glycerol molecule and long-chain fatty acid and medium-chain fatty acid produce structured lipid and water under specific fat enzyme catalysis, the major defect of this method is must momentarily to remove the water generated in esterification reaction process, to prevent product hydrolysis from causing the productivity of structured lipid to reduce, therefore the method is restricted in application aspect.
(3) acid hydrolyzation
Acid hydrolyzation refers to that free fatty reacts under the effect of lipase with the acyl group on triglyceride; the method uses sn1 more; 3 specific lipases are as catalyst; keeping, the fatty acid on original oils and fats sn2 position is constant; at sn1,3 upper insertions have the fatty acid formation structured lipid of specific function.But reaction needs to add excess fatty acids, and fatty acid price is high, can increase cost and later separation operation easier.
(4) ester-interchange method
Ester-interchange method refers under specific fat enzyme catalysis, the reaction occurred between triglyceride or triglyceride and the simple fatty acids ester of two kinds of different compositions, the method that the intermolecular acyl group of esters occurs to exchange and obtains purpose structured lipid.The raw material of ester exchange can be the natural oil that price is relatively cheap, and cost reduces, and simultaneous reactions condition is easily controllable, and technique is simple, is the best approach producing non-specific configuration fat.The unique advantage of MLCT digestion and metabolism, is widely used at clinical medical nutritional supplement arts.Along with food science and nutrition of lipids the reach of science, in edible field, MLCT in addition to providing required energy and nutrition for people, some disease for the treatment of and prevention that also can be potential, there is important practical significance and application potential.It is therefore desirable to research and produce the low cost of MLCT, the simple production method of technique, the natural oil wherein using natural oil at a low price or the fatty acid (EPA, DHA) containing special dietary value is raw material, selection has simple to operate, it is easy to the ester exchange mode of separation is method for optimizing.
Summary of the invention
The purpose of this part is summarize some aspects of embodiments of the invention and briefly introduce some preferred embodiments.Make a summary in this part and the description of the present application and denomination of invention may be done a little simplification or omit to avoid making the purpose of this part, specification digest and denomination of invention to obscure, and this simplification or omission cannot be used for limiting the scope of the present invention.
In view of problem present in the method for backbone triglyceride in above-mentioned and/or existing synthesis, it is proposed that the present invention.
Therefore, the present invention seeks to, overcome the deficiency that existing conventional chemistry synthesizes, it is provided that a kind of synthesize with biological enzyme in organic single_phase system in the method for backbone triglyceride.
For solving above-mentioned technical problem, according to an aspect of the present invention, the technical scheme is that a kind of method of long-chain fatty acid structured triglyceride in enzymatic clarification, it is characterized in that, including, by long chain triglyceride and medium chain triglyceride 1:0.2 in mass ratio～5 mixing, under solvent-free system, add lipase, temperature be 40～100 DEG C, speed of agitator be stirring reaction 0.5～15h under conditions of 50～800r/min, obtain the product containing middle Long carbon chain structured triglyceride.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described long chain triglyceride includes one or more in Oleum Brassicae campestris, soybean oil, Oleum Arachidis hypogaeae semen, Semen Maydis oil, Oleum Camelliae, safflower oil, olive oil, Testa oryzae oil, high oleic sunflower oil, fish oil or algae oil.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described algae oil includes that the algae rich in arachidonic algae oil or rich in docosahexenoic acid is oily.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described medium chain triglyceride is C6～C12Acylglycerol three ester of fatty acid includes, one or more in caproic acid triglyceride, Trivent OCG, tricaprin, pungent tricaprin, lauric acid three ester.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: long chain triglyceride and medium chain triglyceride 1:0.4 in mass ratio～1 are mixed by described long chain triglyceride and medium chain triglyceride 1:0.2 in mass ratio～5 mixing being preferably.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described lipase includes one or more in immobilized enzyme LipozymeRMIM, immobilized enzyme NS40086, immobilized enzyme LipozymeTLIM, immobilized enzyme Novozym435, immobilized enzyme Lipozyme435, its addition accounts for the 1%～15% of triglyceride gross mass.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described addition accounts for 1%～the 15% preferably 5～10% of triglyceride gross mass.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described temperature is 40～100 DEG C and is preferably 50～80 DEG C.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described speed of agitator is 50～800r/min to be preferably 200～500r/min.
As a kind of preferred version of the method for backbone triglyceride in enzymatic clarification of the present invention, wherein: described reaction 0.5～15h is preferably 1～5h.
The present invention had the advantage that into, the method of backbone triglyceride in enzymatic clarification provided by the present invention, it it is specificity by utilizing enzyme process to prepare and high efficiency by preferably optimization material factor, reaction condition factor, the present invention is had, and reaction condition is gentle, reaction is efficient and the simple advantage of technique, can reach the effect not available for conventional chemistry synthesis.Meanwhile, the present invention does not introduce unnecessary organic reagent, adds the interaction of enzyme-to-substrate, improves reaction efficiency；Using the natural oil that price is relatively low, selected lipase recoverable, cost is substantially reduced；Preparation process does not has the generation of by-product, reduces the difficulty of subsequent purification operation.As can be seen here, the synthetic method reaction rate that the present invention provides is fast, and conversion ratio is high, and reaction condition is gentle, be a kind of efficiently, quickly, meet Green Chemistry, be easy to the synthetic method of large-scale industrialization promotion.
Accompanying drawing explanation
In order to be illustrated more clearly that the technical scheme of the embodiment of the present invention, in describing embodiment below, the required accompanying drawing used is briefly described, apparently, accompanying drawing in describing below is only some embodiments of the present invention, for those of ordinary skill in the art, on the premise of not paying creative work, it is also possible to obtain other accompanying drawing according to these accompanying drawings.Wherein:
Fig. 1 is soybean oil and the reversed-phase liquid chromatography of the sweet three esterase method ester exchange reaction raw mixtures of pungent capric acid of embodiment 1.
Fig. 2 is soybean oil and the reversed-phase liquid chromatography of the sweet three esterase method product of transesterification reaction of pungent capric acid of embodiment 1.
Fig. 3 is high oleic sunflower oil and the reversed-phase liquid chromatography of glycerol decanoate enzyme process product of transesterification reaction of embodiment 5.
Detailed description of the invention
Understandable for enabling the above-mentioned purpose of the present invention, feature and advantage to become apparent from, below in conjunction with specific embodiment, the detailed description of the invention of the present invention is described in detail.
Elaborate a lot of detail in the following description so that fully understanding the present invention, but the present invention can also use other to be different from alternate manner described here to be implemented, those skilled in the art can do similar popularization in the case of intension of the present invention, and therefore the present invention is not limited by following public specific embodiment.
Secondly, " embodiment " or " embodiment " referred to herein refers to may be included in special characteristic, structure or the characteristic at least one implementation of the present invention.Different in this manual local " in one embodiment " occurred not refer both to same embodiment, are not single or the most mutually exclusive with other embodiments embodiment.
Embodiment 1
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, soybean oil and sweet three esters of pungent capric acid are 6:4 in mass ratio, under solvent-free system, add 8% immobilized-lipase Lipozyme435, stirring reaction 3h at normal pressure 85 DEG C, mixing speed is 400r/min, after reaction terminates, under the conditions of 4000r/min, centrifugal 10min removes lipase, obtains middle backbone triglyceride, analyzing through HPLC, the content of middle backbone triglyceride reaches 82.26%.
Embodiment 2
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, Oleum Brassicae campestris and sweet three esters of pungent capric acid are 1:1 in mass ratio, under solvent-free system, add 5% immobilized-lipase Novozym435, stirring reaction 4h at normal pressure 80 DEG C, mixing speed is 300r/min, after reaction terminates, under the conditions of 4000r/min, centrifugal 10min removes lipase, obtains middle backbone triglyceride, analyzing through HPLC, the content of middle backbone triglyceride reaches 73.26%.
Embodiment 3
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, fish oil and sweet three esters of octanoic acid are 1:2 in mass ratio, under solvent-free system, add 10% immobilized-lipase NS40086, stirring reaction 2h at normal pressure 60 DEG C, mixing speed is 500r/min, after reaction terminates, under the conditions of 4000r/min, centrifugal 10min removes lipase, obtains middle backbone triglyceride, analyzing through HPLC, the content of middle backbone triglyceride reaches 65.82%.
Embodiment 4
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, the algae oil of docosahexenoic acid (DHA) and tricaprin are 1:3 in mass ratio, under solvent-free system, add 6% immobilized-lipase LipozymeRMIM, stirring reaction 4h at normal pressure 55 DEG C, mixing speed is 400r/min, after reaction terminates, under the conditions of 4000r/min, centrifugal 10min removes lipase, obtain the middle backbone triglyceride rich in docosahexenoic acid (DHA), analyzing through HPLC, the content of middle backbone triglyceride reaches 56.45%.
Embodiment 5
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, high oleic sunflower oil and glycerol decanoate are 3:1 in mass ratio, under solvent-free system, add 5% immobilized-lipase LipozymeTLIM, stirring reaction 3h at normal pressure 50 DEG C, mixing speed is 400r/min, after reaction terminates, under the conditions of 4000r/min, centrifugal 10min removes lipase, obtains middle backbone triglyceride, analyzing through HPLC, the content of middle backbone triglyceride reaches 59.28%.
Embodiment 6
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, algae oil and caproic acid triglyceride rich in arachidonic acid (ARA) are 2:1 in mass ratio, under solvent-free system, add 10% immobilized-lipase Lipozyme435, stirring reaction 5h at normal pressure 70 DEG C, mixing speed is 300r/min, after reaction terminates, under the conditions of 4000r/min, centrifugal 10min removes lipase, obtain the middle backbone triglyceride rich in arachidonic acid (ARA), analyzing through HPLC, the content of middle backbone triglyceride reaches 78.33%.
As can be seen here, the present invention utilizes specificity and the high efficiency catalyzed transesterification of enzyme, play the advantage of organic single_phase system simultaneously, make reaction efficiency high, technique is simple, no coupling product generates, and reduces the difficulty of subsequent purification operation, and the large-scale industrial production being suitable for random middle backbone triglyceride is promoted；Raw material is crude vegetal, and price is low, and safety is high, meanwhile, by the recycling of enzyme can be substantially reduced cost.Visible, the present invention be a kind of efficiently, quickly, meet Green Chemistry, be easy to the synthetic method of large-scale industrialization promotion, its application prospect is the most wide.
It should be noted that, above example is only in order to illustrate technical scheme and unrestricted, although the present invention being described in detail with reference to preferred embodiment, it will be understood by those within the art that, technical scheme can be modified or equivalent, without deviating from the spirit and scope of technical solution of the present invention, it all should be contained in the middle of scope of the presently claimed invention.
Claims (10)
1. the method for long-chain fatty acid structured triglyceride in an enzymatic clarification, it is characterised in that: include,
By long chain triglyceride and medium chain triglyceride 1:0.2 in mass ratio～5 mixing, under solvent-free system, add lipase, temperature be 40～100 DEG C, speed of agitator be stirring reaction 0.5～15h under conditions of 50～800r/min, obtain the product containing middle Long carbon chain structured triglyceride.
2. the method for backbone triglyceride in enzymatic clarification as claimed in claim 1, it is characterised in that: described long chain triglyceride includes one or more in Oleum Brassicae campestris, soybean oil, Oleum Arachidis hypogaeae semen, Semen Maydis oil, Oleum Camelliae, safflower oil, olive oil, Testa oryzae oil, high oleic sunflower oil, fish oil or algae oil.
3. the method for backbone triglyceride in enzymatic clarification as claimed in claim 2, it is characterised in that: described algae oil includes that the algae rich in arachidonic algae oil or rich in docosahexenoic acid is oily.
4. the method for backbone triglyceride in enzymatic clarification as claimed in claim 1 or 2, it is characterised in that: described medium chain triglyceride is C6～C12Acylglycerol three ester of fatty acid includes, one or more in caproic acid triglyceride, Trivent OCG, tricaprin, pungent tricaprin, lauric acid three ester.
5. the method for backbone triglyceride in enzymatic clarification as claimed in claim 1 or 2, it is characterised in that: long chain triglyceride and medium chain triglyceride 1:0.4 in mass ratio～1 are mixed by described long chain triglyceride and medium chain triglyceride 1:0.2 in mass ratio～5 mixing being preferably.
6. the method for backbone triglyceride in enzymatic clarification as claimed in claim 1 or 2, it is characterized in that: described lipase includes one or more in immobilized enzyme LipozymeRMIM, immobilized enzyme NS40086, immobilized enzyme LipozymeTLIM, immobilized enzyme Novozym435, immobilized enzyme Lipozyme435, its addition accounts for the 1%～15% of triglyceride gross mass.
7. the method for backbone triglyceride in enzymatic clarification as claimed in claim 6, it is characterised in that: described addition accounts for 1%～the 15% preferably 5～10% of triglyceride gross mass.
8. the method for backbone triglyceride in enzymatic clarification as claimed in claim 1 or 2, it is characterised in that: described temperature is 40～100 DEG C and is preferably 50～80 DEG C.
9. the method for backbone triglyceride in enzymatic clarification as claimed in claim 1 or 2, it is characterised in that: described speed of agitator is 50～800r/min to be preferably 200～500r/min.
10. the method for backbone triglyceride in enzymatic clarification as claimed in claim 1 or 2, it is characterised in that: described reaction 0.5～15h is preferably 1～5h.
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105602931A (en) * | 2016-03-11 | 2016-05-25 | 东北农业大学 | Method for synthesizing carbon chain triacylglycerol under supercritical CO2 system based on magnetic immobilized enzyme method |
| CN107549332A (en) * | 2017-09-11 | 2018-01-09 | 江南大学 | Strengthen method of baby's long-chain polyunsaturated fatty acid bioavailability and products thereof |
| CN107828830A (en) * | 2017-12-14 | 2018-03-23 | 广州白云山汉方现代药业有限公司 | A kind of method that backbone triglycerides forms in adjustment |
| CN107974471A (en) * | 2017-12-14 | 2018-05-01 | 广州白云山汉方现代药业有限公司 | A kind of method of backbone triglycerides in mixed catalytic synthesis |
| CN109666541A (en) * | 2018-07-16 | 2019-04-23 | 河北康睿达脂质有限公司 | The preparation method of long-chain fat acid lipid in a kind of high-purity |
| 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 |
| CN111304006A (en) * | 2020-03-03 | 2020-06-19 | 江南大学 | Preparation method of high-quality triglyceride with medium-long carbon chain structure and rich in α -linolenic acid and product |
| WO2020248710A1 (en) * | 2019-06-14 | 2020-12-17 | 广东省农业科学院蚕业与农产品加工研究所 | Grease composition and preparation method therefor |
| CN112538505A (en) * | 2020-12-08 | 2021-03-23 | 华南理工大学 | Technology for enzymatic transesterification |
| CN112913934A (en) * | 2021-03-24 | 2021-06-08 | 固始县豫申粮油工贸有限公司 | Preparation method of powdered medium-long carbon chain triglyceride rice oil |
| CN113604517A (en) * | 2021-07-08 | 2021-11-05 | 北京化工大学 | Method for preparing structured lipid by enzymatic method selective catalysis |
| CN115125058A (en) * | 2022-07-27 | 2022-09-30 | 龙岩市祥优实业有限公司 | Preparation method of special health-care camellia oil for mothers and infants |
| CN115369132A (en) * | 2021-09-23 | 2022-11-22 | 江南大学 | Enzymatic synthesis method of medium-long chain triglyceride |
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| CN101979625A (en) * | 2010-11-03 | 2011-02-23 | 江南大学 | Method for synthesizing triglyceride with medium/long-chain structure by catalyzing ester exchange through enzyme |
| 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 |
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| CN101979625A (en) * | 2010-11-03 | 2011-02-23 | 江南大学 | Method for synthesizing triglyceride with medium/long-chain structure by catalyzing ester exchange through enzyme |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105602931A (en) * | 2016-03-11 | 2016-05-25 | 东北农业大学 | Method for synthesizing carbon chain triacylglycerol under supercritical CO2 system based on magnetic immobilized enzyme method |
| CN107549332A (en) * | 2017-09-11 | 2018-01-09 | 江南大学 | Strengthen method of baby's long-chain polyunsaturated fatty acid bioavailability and products thereof |
| CN107974471B (en) * | 2017-12-14 | 2021-04-20 | 广州白云山汉方现代药业有限公司 | Method for synthesizing triglyceride with medium-long chain structure by mixed catalysis |
| CN107828830A (en) * | 2017-12-14 | 2018-03-23 | 广州白云山汉方现代药业有限公司 | A kind of method that backbone triglycerides forms in adjustment |
| CN107974471A (en) * | 2017-12-14 | 2018-05-01 | 广州白云山汉方现代药业有限公司 | A kind of method of backbone triglycerides in mixed catalytic synthesis |
| CN109666541A (en) * | 2018-07-16 | 2019-04-23 | 河北康睿达脂质有限公司 | The preparation method of long-chain fat acid lipid in a kind of high-purity |
| CN109666541B (en) * | 2018-07-16 | 2019-12-24 | 河北康睿达脂质有限公司 | Preparation method of high-purity medium-long chain fatty acid grease |
| CN109907126B (en) * | 2019-04-18 | 2021-09-07 | 江南大学 | Grease composition of medium-long carbon chain triglyceride and preparation method thereof |
| 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 |
| WO2020248710A1 (en) * | 2019-06-14 | 2020-12-17 | 广东省农业科学院蚕业与农产品加工研究所 | Grease composition and preparation method therefor |
| CN111304006A (en) * | 2020-03-03 | 2020-06-19 | 江南大学 | Preparation method of high-quality triglyceride with medium-long carbon chain structure and rich in α -linolenic acid and product |
| CN112538505A (en) * | 2020-12-08 | 2021-03-23 | 华南理工大学 | Technology for enzymatic transesterification |
| CN112913934A (en) * | 2021-03-24 | 2021-06-08 | 固始县豫申粮油工贸有限公司 | Preparation method of powdered medium-long carbon chain triglyceride rice oil |
| CN113604517A (en) * | 2021-07-08 | 2021-11-05 | 北京化工大学 | Method for preparing structured lipid by enzymatic method selective catalysis |
| CN115369132A (en) * | 2021-09-23 | 2022-11-22 | 江南大学 | Enzymatic synthesis method of medium-long chain triglyceride |
| CN115125058A (en) * | 2022-07-27 | 2022-09-30 | 龙岩市祥优实业有限公司 | Preparation method of special health-care camellia oil for mothers and infants |
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Application publication date: 20160803 |