CN107254494A - A kind of glycerine ester type PUFA preparation method - Google Patents
A kind of glycerine ester type PUFA preparation method Download PDFInfo
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- CN107254494A CN107254494A CN201710481152.1A CN201710481152A CN107254494A CN 107254494 A CN107254494 A CN 107254494A CN 201710481152 A CN201710481152 A CN 201710481152A CN 107254494 A CN107254494 A CN 107254494A
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- pufa
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
Abstract
The invention discloses a kind of glycerine ester type PUFA preparation method; it regard eutectic solvent as reaction medium; using immobilized lipase as catalyst; it is passed through protection gas; it is esterified or transesterification using glycerine and free state PUFA or PUFA short-chain alcohol ester; then stratification, upper strata is high yield pulp1 triglyceride type PUFA esterification products.The present invention is used as reaction medium by the use of eutectic solvent, glycerine and free state PUFA or PUFA short-chain alcohol ester are raw material, high by triglyceride type PUFA contents in the immobilized lipase product that catalytic esterification or transesterification are generated at low temperature, easy to operate, cost is low and energy-conserving and environment-protective.
Description
Technical field
The present invention relates to a kind of glycerine ester type PUFA preparation method.
Background technology
Polyunsaturated fatty acid (polyunsaturated fatty acids, be abbreviated as PUFA) refer to containing two or
Two or more double bond and carbon chain lengths are the general name of the straight chain fatty acid of 18~22 carbon atoms.Wherein, it is most representational
PUFA is mainly EPA, DPA and DHA.Research shows that PUFA has multi-efficiency, such as treatment autoimmune disorder, promotion circulation
The health of system, the transmitting function for reducing cholesterol, prevention of arterial atherosis and raising retina etc..Presently commercially available
EPA, DHA product are mainly sequestered or ethyl ester type.However, sequestered PUFA is easily aoxidized, and has harsh flavor, mouthfeel is not
It is good, it is directly edible to be difficult to be accepted.Ethyl ester type digests and absorbed in human body relatively difficult, and can be produced in metabolic process
Ethanol, it is understood that there may be potential safety hazard.
Triglyceride type PUFA is while its physiology and trophic function is kept, and aroma and flavor is more gentle, it is easy to digest
Absorb.Moreover, research shows that triglyceride type PUFA has more preferable inoxidizability and bioavilability.Even however, coming
Source most abundant deep sea fish oil, triglyceride type PUFA content is also less than 20%.Traditional triglyceride type PUFA synthesis works
In skill, reacted using glycerine and aliphatic acid are directly enzyme-added under solvent-free system, or use for example tertiary fourth of organic solvent
Alcohol is reacted as solvent, and the former triglyceride type PUFA yield is only capable of reaching 22% or so, though the latter is improved, its
The problem of environmental pollution and food-safety problem caused can not be ignored.The product of higher purity must coordinate other method such as molecule
Distillation etc. realizes that raw material availability is low.And due to the emulsification of monoglyceride and diglyceride in product so that it is remaining sweet
Oil is difficult to realize quick separating with esterification products, still needs to using the operation such as centrifugation, time-consuming, energy expenditure is big and with high costs.
CN101255380 discloses a kind of triglyceride type fish oil and preparation method thereof, using ethyl ester type fish oil and glycerine as
Raw material, Novozym 435 is catalyst, efficiently solves the problem of conventional ethyl ester type fish oil medicinal health effect is poor；
CN103242969A discloses a kind of preparation method of triglyceride type fish oil, with ethyl ester type fish oil, glycerine in base catalyst
Transesterification is carried out, cost of material is low, and equipment investment is few；CN102994580A discloses a kind of ester type of high-purity glycerol three
PUFA preparation method, is that catalyst glycerine reacts with PUFA first with lipase Novozym 435, then removes
The catalyst of Novozym 435, then through partial glyceride lipase Lipase SMG1 at not higher than 5 DEG C it is inclined in catalytic mixing thing
Glycerine ester type PUFA is hydrolyzed or alcoholysis reaction with hydroxyl donor, realizes the enzyme process of the ester type PUFA products of high-purity glycerol three
Synthesis.
In summary, existing triglyceride type PUFA technology of preparing operating process is complicated, and course of reaction needs to coordinate
It is complicated using the separation of plurality of devices and glyceride product, and some techniques need to participate in glycerine with the use of a variety of enzyme preparations
Three ester type PUFA synthesis, this adds increased triglyceride type PUFA synthesis cost.
The content of the invention
In view of the above-mentioned problems, it is an object of the invention to provide a kind of glycerine ester type PUFA preparation method, with glycerine and trip
Amorph PUFA or PUFA short-chain alcohol ester are substrate, the ester type PUFA of synthetic glycerine three, this method reaction speed in eutectic solvent
It hurry up, product is easily isolated, energy-conserving and environment-protective can effectively improve substrate conversion efficiency, reduce production cost, efficiently solve because of complexity point
The PUFA problem of oxidation brought from process, improves product stability.
To realize object above, the present invention provides following technical scheme：
A kind of glycerine ester type PUFA preparation method, using eutectic solvent as reaction medium, using immobilized lipase as
Catalyst, is passed through protection gas, is esterified or transesterification using glycerine and free state PUFA or PUFA short-chain alcohol ester, then
Stratification (reclaims lower floor's eutectic solvent) using separatory funnel, and upper strata is high yield pulp1 triglyceride type PUFA esterification production
Thing.
The eutectic solvent be any one in urea, xylitol, trehalose with Choline Chloride in molar ratio (1~
3):Obtained liquid mixture is heated after 1 mixing.
Condition prepared by the eutectic solvent：Using Rotary Evaporators, 0.06~0.1MPa of vacuum, temperature 50~80
DEG C, 2~4h of time.
Described eutectic solvent preparation parameter be vacuum 0.08MPa, 65 DEG C of temperature, the time is 2h.
The PUFA is the mixture rich in free state EPA, DPA and DHA, and the PUFA short-chain alcohol esters are EPA short chain alcohols
The mixture of ester, DPA short-chain alcohol esters and DHA short-chain alcohol esters.
The mol ratio of the glycerine and PUFA or PUFA short-chain alcohol esters is (1~5):1.
The consumption of the immobilized lipase is the 0.5~10% of reaction substrate gross mass；The use of the eutectic solvent
Measure as 2~4 times of reaction substrate cumulative volume.
The consumption of the immobilized lipase is the 3~10% of reaction substrate gross mass.
The immobilized lipase is Novozym 435, Lipozyme RM IM, Lipozyme PS IM or Lipozyme
TL IM。
The esterification or the temperature of transesterification are 30~60 DEG C.
The time of the esterification or transesterification is 6~24h.
In the present invention, the reaction medium eutectic solvent of use has certain water suction and inhales alcohol ability, can remove in real time
During the moisture or glycerine and PUFA short-chain alcohol ester transesterifications that are produced in glycerine and free state PUFA esterification reaction processes
The short chain alcohol of generation, promotes esterification to be carried out to positive direction.Esterification under traditional solvent-free system, due to reacting
The monoglyceride and diglyceride produced in journey is emulsifying agent so that reaction product forms with residual substrate and stablizes homogeneous body
System, the water produced in course of reaction can cause to a certain extent triglyceride type PUFA in Product inhibiton, esterification products
Rate is than relatively low, and product separation process still needs to realize using dissipative operations such as centrifugations.Using above-mentioned eutectic solvent as anti-
Answer after medium, glycerine can be well dissolved in wherein, reaction product is still two-phase, it is only necessary to remove sub-cloud using common separatory funnel
Eutectic solvent, can realize the effect for removing solvent, the water that produces in residual reaction substrate glycerol and course of reaction or
Short chain alcohol is also removed in the process.
Compared with prior art, the beneficial effects of the present invention are：
(1) present invention utilizes the acyl acceptor that glycerine is PUFA, using eutectic solvent as reaction medium, immobilized lipase
Enzyme is that catalyst glycerine is esterified or transesterification with free state PUFA or PUFA short-chain alcohol ester, glycerine three in product
Ester type PUFA contents are high, can reach 50%~60%；Compared with the esterification products under solvent-free system, triglyceride type PUFA
Content improves 2~3 times.
(2) present invention uses eutectic solvent to be reacted at ambient pressure for reaction medium, and reaction condition is gentle, reaction system letter
Single, product is easily isolated；The eutectic solvent of recovery can be reused more than 5 times.
Embodiment
The present invention is more specifically described in detail with reference to specific embodiment, but embodiments of the present invention are not limited
In this, for the technological parameter not indicated especially, routine techniques progress can refer to.
Embodiment 1
The preparation of eutectic solvent：116g Choline Chlorides and 100g urea (mole of Choline Chloride and urea are weighed respectively
Ratio is 1:2) vacuum 0.08MPa in Rotary Evaporators, is placed in, 65 DEG C of heating water bath 2h are until obtain colourless transparent liquid.
Take 50mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 28.3gPUFA (glycerine
Mol ratio with PUFA is 2.8:1) with 1.5g immobilised enzymes LipozymeRMIM (Novozymes Products), it is filled with nitrogen
As protection gas, reaction under the conditions of 40 DEG C of waters bath with thermostatic control is placed in, rotating speed is controlled in 500rpm, reaction time 24h.Use separatory funnel
Except sub-cloud eutectic solvent, upper strata glyceride product is collected.Each component weight/mass percentage composition is as follows in glyceride product：Glycerine
Three esters 30.38%, diglyceride 42.05%, monoglyceride 10.72%, free fatty 16.85%.Eutectic solvent is repeated
After 5 times, content of triglyceride remains at 29.89%.
Embodiment 2
The preparation be the same as Example 1 of eutectic solvent.
Take 50mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 28.3gPUFA (glycerine
Mol ratio with PUFA is 2.8:1) with 1.5g immobilised enzymes Novozym 435 (Novozymes Products), it is filled with nitrogen work
For protection gas, reaction under the conditions of 40 DEG C of waters bath with thermostatic control is placed in, rotating speed is controlled in 500rpm, reaction time 24h.Removed with separatory funnel
Sub-cloud eutectic solvent, collects upper strata glyceride product.Each component weight/mass percentage composition is as follows in glyceride product：Glycerine three
Ester 43.98%, diglyceride 41.08%, monoglyceride 4.85%, free fatty 10.09%.Eutectic solvent is reused
After 5 times, content of triglyceride remains at 42.60%.
Embodiment 3
The preparation be the same as Example 1 of eutectic solvent.
Take 50mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 15.5gPUFA (glycerine
Mol ratio with PUFA is 5:1) with 1.5g immobilised enzymes Novozym 435 (Novozymes Products), it is filled with nitrogen conduct
Gas is protected, reaction under the conditions of 40 DEG C of waters bath with thermostatic control is placed in, rotating speed is controlled in 500rpm, reaction time 24h.Removed with separatory funnel
Lower floor's eutectic solvent, collects upper strata glyceride product.Each component weight/mass percentage composition is as follows in glyceride product：Triglycerides
49.58%, diglyceride 38.06%, monoglyceride 3.80%, free fatty 8.56%.Eutectic solvent is reused 5 times
Afterwards, content of triglyceride remains at 46.86%.
Embodiment 4
The preparation be the same as Example 1 of eutectic solvent.
Take 60mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 15.5gPUFA (glycerine
Mol ratio with PUFA is 5:1) with 1.5g immobilised enzymes Novozym 435 (Novozymes Products), it is filled with nitrogen conduct
Gas is protected, reaction under the conditions of 40 DEG C of waters bath with thermostatic control is placed in, rotating speed is controlled in 500rpm, reaction time 24h.Removed with separatory funnel
Lower floor's eutectic solvent, collects upper strata glyceride product.Each component weight/mass percentage composition is as follows in glyceride product：Triglycerides
51.40%, diglyceride 33.68%, monoglyceride 3.35%, free fatty 11.57%.Eutectic solvent recycling 5
After secondary, content of triglyceride remains at 48.50%.
Embodiment 5
The preparation be the same as Example 1 of eutectic solvent.
Take 60mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 15.5gPUFA (glycerine
Mol ratio with PUFA is 5:1) with 3.0g immobilised enzymes Novozym 435 (Novozymes Products), it is filled with nitrogen conduct
Gas is protected, reaction under the conditions of 40 DEG C of waters bath with thermostatic control is placed in, rotating speed is controlled in 500rpm, reaction time 24h.Removed with separatory funnel
Lower floor's eutectic solvent, collects upper strata glyceride product.Each component weight/mass percentage composition is as follows in glyceride product：Triglycerides
55.16%, diglyceride 30.75%, monoglyceride 2.59%, free fatty 11.50%.Eutectic solvent recycling 5
After secondary, content of triglyceride remains at 52.27%.
Embodiment 6
The preparation be the same as Example 1 of eutectic solvent.
Take 60mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 15.5gPUFA (glycerine
Mol ratio with PUFA is 5:1) with 3.0g immobilised enzymes Novozym 435 (Novozymes Products), it is filled with nitrogen conduct
Gas is protected, reaction under the conditions of 50 DEG C of waters bath with thermostatic control is placed in, rotating speed is controlled in 500rpm, reaction time 24h.Removed with separatory funnel
Lower floor's eutectic solvent, collects upper strata glyceride product.Each component weight/mass percentage composition is as follows in glyceride product：Triglycerides
59.16%, diglyceride 27.72%, monoglyceride 2.62%, free fatty 10.50%.Eutectic solvent recycling 5
After secondary, content of triglyceride remains at 52.60%.
Embodiment 7
The preparation of eutectic solvent：Weigh respectively 116g Choline Chlorides and 850g trehaloses (Choline Chloride and trehalose
Molar ratio is 1:3), other step be the same as Examples 1.
Take 60mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 15.5gPUFA (glycerine
Mol ratio with PUFA is 5:1) with 3g immobilised enzymes Novozym 435 (Novozymes Products), nitrogen is filled with as guarantor
Gas is protected, reaction under the conditions of 50 DEG C of waters bath with thermostatic control is placed in, rotating speed is controlled in 500rpm, reaction time 24h.Removed down with separatory funnel
Layer eutectic solvent, collects upper strata glyceride product.Each component weight/mass percentage composition is as follows in glyceride product：Triglycerides
52.12%, diglyceride 33.07%, monoglyceride 2.28%, free fatty 12.53%.Eutectic solvent recycling 5
After secondary, content of triglyceride remains at 37.19%.
Embodiment 8
The preparation be the same as Example 1 of eutectic solvent.
Take 60mL eutectic solvents to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 15.5gPUFA ethyl esters
(glycerine and PUFA mol ratio are 2.5:1) with 3g immobilised enzymes Novozym 435 (Novozymes Products), it is filled with nitrogen
Gas is placed in reaction under the conditions of 50 DEG C of waters bath with thermostatic control as protection gas, and rotating speed is controlled in 500rpm, reaction time 24h.Leaked with point liquid
Bucket removes sub-cloud eutectic solvent, collects upper strata glyceride product.Each component weight/mass percentage composition is as follows in glyceride product：It is sweet
Oily three esters 33.75%, diglyceride 30.80%, monoglyceride 8.58%, PUFA ethyl esters 26.87%.Eutectic solvent repeats profit
After 5 times, content of triglyceride remains at 29.55%.
Comparative example 1
By 23.0g glycerine, 15.5gPUFA, (glycerine and PUFA mol ratio are 5:1) with 1.5g immobilised enzymes Novozym
435 (Novozymes Products) are added in round-bottomed flask, are filled with nitrogen as protection gas, are placed in 40 DEG C of water bath with thermostatic control bars
Reacted under part, rotating speed is controlled in 500rpm, reaction time 24h.Reaction product is transferred in centrifuge tube, in 10000rpm conditions
Lower centrifugation 5min, except the unreacted glycerine of sub-cloud, collects upper strata glyceride product.Each component quality percentage in glyceride product
Content is as follows：Triglycerides 23.85%, diglyceride 46.90%, monoglyceride 17.95%, free fatty 11.30%.
Comparative example 2
Take the 60mL tert-butyl alcohols to be added in round-bottomed flask, then sequentially add 23.0g glycerine, 15.5gPUFA (glycerine with
PUFA mol ratio is 5:1) with 3.0g immobilised enzymes Novozym 435 (Novozymes Products), nitrogen is filled with as guarantor
Gas is protected, is reacted under the conditions of 50 DEG C of waters bath with thermostatic control, rotating speed is controlled in 500rpm, reaction time 24h.It is subsequently placed in Rotary Evaporators
In remove solvent tertiary butanol under the conditions of 85 DEG C, 0.1MPa, by product be transferred in centrifuge tube under the conditions of 10000rpm centrifuge
5min, except the unreacted glycerine of sub-cloud, collects upper strata glyceride product.Each component weight/mass percentage composition is such as in glyceride product
Under：28.09%, diglyceride 43.82%, monoglyceride 13.09%, free fatty 15.00%.
Claims (10)
1. a kind of glycerine ester type PUFA preparation method, it is characterised in that using eutectic solvent as reaction medium, with immobilization
Lipase is catalyst, is passed through protection gas, is esterified or transesterification using glycerine and free state PUFA or PUFA short-chain alcohol ester
React, then stratification, upper strata is triglyceride type PUFA esterification products.
2. preparation method according to claim 1, it is characterised in that the eutectic solvent is urea, xylitol, marine alga
Any one in sugar with Choline Chloride in molar ratio (1~3):Obtained liquid mixture is heated after 1 mixing.
3. preparation method according to claim 2, it is characterised in that condition prepared by the eutectic solvent：Using rotation
Turn evaporimeter, 0.06~0.1MPa of vacuum, 50~80 DEG C of temperature, 2~4h of time.
4. preparation method according to claim 1, it is characterised in that the PUFA is rich in free state EPA, DPA and DHA
Mixture, the PUFA short-chain alcohol esters be EPA short-chain alcohol esters, DPA short-chain alcohol esters and DHA short-chain alcohol esters mixture.
5. the preparation method according to claim 1 or 2 or 3 or 4, it is characterised in that the glycerine and PUFA or PUFA are short
The mol ratio of chain alcohol ester is (1~5):1.
6. preparation method according to claim 5, it is characterised in that the consumption of the immobilized lipase is reaction substrate
The 0.5~10% of gross mass；The consumption of the eutectic solvent is 2~4 times of reaction substrate cumulative volume.
7. preparation method according to claim 6, it is characterised in that the consumption of the immobilized lipase is reaction substrate
The 3~10% of gross mass.
8. preparation method according to claim 7, it is characterised in that the immobilized lipase be Novozym 435,
Lipozyme RM IM, Lipozyme PS IM or Lipozyme TL IM.
9. preparation method according to claim 8, it is characterised in that the esterification or the temperature of transesterification are
30~60 DEG C.
10. preparation method according to claim 9, it is characterised in that the time of the esterification or transesterification
For 6~24h.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109678703A (en) * | 2019-01-29 | 2019-04-26 | 河南工业大学 | A kind of synthetic method of monoglyceride |
| CN112574975A (en) * | 2020-09-30 | 2021-03-30 | 华南理工大学 | Glyceride lipase mutant G28C-P206C, and coding gene and application thereof |
| CN113061486A (en) * | 2021-04-09 | 2021-07-02 | 广东省农业科学院蚕业与农产品加工研究所 | Method for removing free fatty acid in grease through enzyme catalysis |
| CN113088544A (en) * | 2021-03-29 | 2021-07-09 | 北京化工大学 | Method for synthesizing bio-based epoxy vegetable oil in deep eutectic solvent through enzyme method |
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| CN102994580A (en) * | 2012-11-30 | 2013-03-27 | 华南理工大学 | Preparation method of high-purity triglyceride type PUFA (Polyunsaturated Fatty Acid) |
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| WO2013043151A1 (en) * | 2011-09-19 | 2013-03-28 | Framroze Bomi P | Edible oil with a high concentration of poly-unsaturated fatty acids |
| CN102994580A (en) * | 2012-11-30 | 2013-03-27 | 华南理工大学 | Preparation method of high-purity triglyceride type PUFA (Polyunsaturated Fatty Acid) |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109678703A (en) * | 2019-01-29 | 2019-04-26 | 河南工业大学 | A kind of synthetic method of monoglyceride |
| CN109678703B (en) * | 2019-01-29 | 2021-07-13 | 河南工业大学 | Synthetic method of monoglyceride |
| CN112574975A (en) * | 2020-09-30 | 2021-03-30 | 华南理工大学 | Glyceride lipase mutant G28C-P206C, and coding gene and application thereof |
| CN113088544A (en) * | 2021-03-29 | 2021-07-09 | 北京化工大学 | Method for synthesizing bio-based epoxy vegetable oil in deep eutectic solvent through enzyme method |
| CN113061486A (en) * | 2021-04-09 | 2021-07-02 | 广东省农业科学院蚕业与农产品加工研究所 | Method for removing free fatty acid in grease through enzyme catalysis |
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