CN112280817A - Method for synthesizing soyasterol oleate by catalyzing enzyme through magnetic induction electric field - Google Patents
Method for synthesizing soyasterol oleate by catalyzing enzyme through magnetic induction electric field Download PDFInfo
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- CN112280817A CN112280817A CN202011175838.6A CN202011175838A CN112280817A CN 112280817 A CN112280817 A CN 112280817A CN 202011175838 A CN202011175838 A CN 202011175838A CN 112280817 A CN112280817 A CN 112280817A
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Abstract
The invention discloses a method for synthesizing soyasterol oleate by catalyzing enzyme through a magnetic induction electric field, which comprises the following steps: the method comprises the steps of taking soyasterol and oleic acid as raw materials, and catalytically synthesizing soyasterol oleate under the conditions of a magnetic induction electric field and the presence of enzyme serving as a catalyst. According to the invention, the magnetic induction electric field treatment is adopted in the process of enzymatically synthesizing the soyasterol oleate, the non-thermal effect and the thermal effect of the magnetic induction electric field treatment are utilized, and the action of the enzyme catalyst is utilized to cooperate, so that the esterification reaction rate of enzymatically catalyzed phytosterol and oleic acid is greatly accelerated, the synthesis speed of the soyasterol oleate is obviously improved, the problems of overlong enzymatic synthesis time, overhigh cost and the like are effectively solved, and particularly, the esterification rate is effectively improved and the product quality is improved.
Description
Technical Field
The invention relates to a method for synthesizing soyasterol oleate, in particular to a method for synthesizing soyasterol oleate by using magnetic induction electric field catalytic enzyme.
Background
Soyasterol is a steroid substance contained in soybean, and belongs to phytosterol. Researchers find that the soyasterol has the effects of reducing cholesterol, treating fatty liver and resisting inflammation, so that the soyasterol can be widely applied to production of medicines, health-care products, functional food additives and the like. Currently, soyasterol is mainly extracted from soybean oil residue by a chemical method. However, like other free phytosterols, soy sterol is poorly soluble and has limited bioavailability. It needs to be modified. The common method for modifying the soyasterol is to synthesize sterol ester by combining the soyasterol with oleic acid and the like.
The existing methods for synthesizing sterol ester mainly comprise a chemical method and an enzymatic method. Because the chemical method has high reaction temperature, side reaction occurs, the product components are complex, the separation and purification are difficult, and the safety of the product is easy to damage, so the product produced by the method is often difficult to be accepted by people. On the contrary, compared with the chemical method, the enzymatic synthesis has the advantages of mild conditions, less side reactions, no chemical residues, easy product purification and stable product quality, but the enzymatic synthesis has longer time and overhigh cost, and is not beneficial to large-scale production.
Disclosure of Invention
The invention mainly aims to provide a method for synthesizing soyasterol oleate by catalyzing enzyme through a magnetic induction electric field so as to overcome the defects in the prior art.
In order to achieve the purpose, the technical scheme adopted by the invention comprises the following steps:
the embodiment of the invention provides a method for synthesizing soyasterol oleate by using magnetic induction electric field catalysis enzyme, which comprises the following steps: the method comprises the steps of taking soyasterol and oleic acid as raw materials, and catalytically synthesizing soyasterol oleate under the conditions of a magnetic induction electric field and the presence of enzyme serving as a catalyst.
In some embodiments, the method for enzymatically synthesizing soyasterol oleate by using the magnetically induced electric field catalyst specifically comprises the following steps: and (2) inputting a liquid phase reaction system containing uniformly mixed soyasterol, oleic acid and a catalyst into a magnetic induction electric field reaction device, and reacting the liquid phase reaction system in a magnetic induction electric field provided by the magnetic induction electric field reaction device to obtain the soyasterol oleate.
In some embodiments, the soy sterol to oleic acid molar ratio is from 1:1 to 2: 1.
In some embodiments, the catalyst has a mass of 4-8% of the total mass of soy sterol and oleic acid.
In some embodiments, the liquid phase reaction system further comprises isooctane, wherein the ratio of the amount of isooctane to soy sterol is 10-20 ml: 1 mmol.
In some embodiments, the method for enzymatically synthesizing soyasterol oleate by using a magnetically induced electric field catalyst further comprises: drying soyasterol at 40-60 ℃ for 18-30h, placing in a dryer, cooling to room temperature, mixing with isooctane, oscillating at 25-35 ℃ for 24-48h, and sequentially mixing with oleic acid and a catalyst to form the liquid-phase reaction system.
In some embodiments, the flow rate of the liquid phase reaction system in the magnetic induction electric field is 20-40ml/min, and the terminal temperature of the liquid phase reaction system (the temperature rise terminal temperature of the reaction system caused by the magnetic induction electric field, which is equivalent to the catalytic reaction temperature) is 34-36 ℃ and the reaction time is 30-60 min.
In some embodiments, the liquid-phase reaction system is circulated within a magnetic induction field.
In some embodiments, the relevant operating parameters of the magnetically induced electric field include: the excitation voltage is 600-900V, and the excitation frequency is 180-200 kHz.
In some embodiments, the catalyst comprises N435 lipase (novacin), but is not limited thereto.
In some embodiments, the method for enzymatically synthesizing soyasterol oleate by using a magnetically induced electric field catalyst further comprises: after the reaction is finished, centrifuging the obtained reaction mixture for more than 30s at the rotating speed of 3000-8000 r/min, and then, taking NaHCO with the concentration of 0.3-0.6mol/L3Extracting the solution for more than 3 times, washing the upper layer with anhydrous ethanol for more than 3 times, and pressurizing to 0.12-0.1Drying is carried out under the vacuum condition of 5 MPa.
Compared with the prior art, the embodiment of the invention adopts the magnetic induction electric field treatment in the process of synthesizing the soyasterol oleate by enzyme catalysis, utilizes the non-thermal effect and the thermal effect of the magnetic induction electric field treatment and the action of the enzyme catalyst to cooperate, greatly accelerates the rate of the esterification reaction of the enzyme-catalyzed phytosterol and oleic acid, obviously improves the synthesis speed of the soyasterol oleate, solves the problems of overlong synthesis time, overhigh cost and the like of the enzyme method, and also effectively improves the esterification rate and the product quality.
Drawings
FIG. 1 is an infrared spectrum of a soybean sterol oleate synthesized in example 1 of the present invention.
Detailed Description
Aiming at the defects of the prior art, the inventor of the present invention has long-term research and a great deal of practice, and has quite unexpectedly found that when the soybean sterol oleate is synthesized by an enzymatic method, if a proper magnetic induction electric field is used as an auxiliary material, the synthesis time can be greatly shortened, and surprising effects of significantly improving the esterification rate, the product quality and the like can be generated. Based on such unexpected findings, the applicant has proposed the technical solution of the present invention, and the technical solution, the implementation process and the principle thereof, etc. will be further explained with reference to several embodiments as follows. It is to be understood, however, that within the scope of the present invention, each of the above-described features of the present invention and each of the features described in detail below (examples) may be combined with each other to form new or preferred embodiments. Not to be reiterated herein, but to the extent of space.
In the following examples, unless otherwise specified, various raw materials, reagents, reaction equipment, test equipment and methods used may be obtained by means of commercial sources or the like.
Example 1 a method for enzymatically synthesizing soyasterol oleate by magnetic induction electric field catalysis comprises the following steps:
s1, raw material pretreatment: placing soyasterol in an oven at 60 ℃, drying for 18h, placing in a dryer, cooling to room temperature, and mixing with isooctane according to the ratio of 1 mmol: adding 10ml of the mixture into a beaker at the same time, uniformly mixing, and oscillating for 48 hours at the temperature of 25 ℃;
s2, constructing a reaction system: weighing soyasterol and oleic acid, uniformly mixing according to a molar ratio of 1:1, wherein the total amount is 80g, adding N435 lipase (the dosage is 4% of the total mass of the soyasterol and the oleic acid) serving as a catalyst into the beaker, and uniformly mixing to form a liquid phase reaction system (hereinafter referred to as feed liquid);
s3, magnetic induction electric field circulation treatment: pumping the feed liquid into a magnetic induction field reaction device (an MFR-2L type product produced by England stedt (tin-free) induction technology limited) by using a peristaltic pump, filling all coil pipelines of the magnetic induction field reaction device with the feed liquid, then connecting the feed liquid at an outlet back to a beaker to form a circulating flow path, wherein the flow rate of a treatment tube is 40ml/min, then opening an excitation power supply, setting an excitation voltage of 900V, the excitation frequency is 180kHz, the terminal temperature of a reaction system is 36 ℃, maintaining the catalytic treatment time for 40min, finishing excitation, and finishing treatment, wherein the yield of the soyasterol oleate synthesized under the process condition reaches about 95%;
s4, separation and purification: after the reaction is finished, the feed liquid is completely poured out of the magnetic induction electric field reaction device and flows back to the beaker, centrifugation is carried out at 3000r/min, and NaHCO with the concentration of 0.3mol/L is used3Extracting the solution for 5 times, collecting the upper layer solution, washing with anhydrous ethanol for 3 times, and drying under 0.15MPa to obtain soyasterol oleate with infrared spectrum of about 99%.
Comparative example 1 a method for enzymatically synthesizing soyasterol oleate comprises the following steps:
s1: same as in example 1.
S2: same as in example 1.
S3: and (4) transferring the liquid-phase reaction system prepared in the step S2 into a flask, and reacting in a water bath constant temperature oscillator at the reaction temperature of about 40 ℃ for about 30 hours, wherein under the process condition, the yield of the soyasterol oleate is about 87%.
S4: the target product purity was about 93% as in example 1.
Comparative example 2 a method for enzymatically synthesizing soyasterol oleate comprises the steps of:
S1-S2: same as in example 1.
S3: and (4) transferring the liquid-phase reaction system prepared in the step S2 into a flask, and reacting in a water bath constant temperature oscillator at the reaction temperature of about 36 ℃ for about 30 hours, wherein under the process condition, the yield of the soyasterol oleate is about 69%.
S4: the target product purity was about 75% as in example 1.
Example 2 a method for enzymatically synthesizing soyasterol oleate by magnetic induction electric field catalysis comprises the following steps:
s1, raw material pretreatment: placing soyasterol in an oven at 40 ℃, drying for 30h, placing in a dryer, cooling to room temperature according to the ratio of 1 mmol: adding 20ml of the mixture into a beaker at the same time, uniformly mixing, and oscillating for 24 hours at 35 ℃;
s2, constructing a reaction system: weighing soyasterol and oleic acid, mixing according to a molar ratio of 2:1, adding a catalyst which is N435 lipase (the dosage is 8% of the total mass of the soyasterol and the oleic acid) into the beaker, and uniformly mixing to form a liquid phase reaction system (hereinafter referred to as feed liquid);
s3, magnetic induction electric field circulation treatment: pumping the feed liquid into a magnetic induction electric field reaction device (an MFR-2L type product produced by England-ster (tin-free) induction technology limited) by using a peristaltic pump, filling all coil pipelines of the magnetic induction electric field reaction device with the feed liquid, then connecting the feed liquid at an outlet back to a beaker to form a circulating flow path, wherein the flow rate of a treatment tube is 20ml/min, then opening an excitation power supply, setting an excitation voltage of 600V, the excitation frequency is 200kHz, the terminal temperature of a reaction system is 34 ℃, maintaining the catalytic treatment time for 60min, finishing excitation, and finishing treatment, wherein the yield of the soyasterol oleate synthesized under the process condition is about 93%;
s4, separation and purification: after the reaction is finished, the feed liquid is completely poured out of the magnetic induction electric field reaction device and flows back to the beaker, centrifugation is carried out at 8000r/min, and NaHCO with the concentration of 0.6mol/L is used3Extracting the solution for 3 times, collecting the upper solution, and reusingWashing with anhydrous ethanol for 3 times, and drying under 0.12MPa to obtain soyasterol oleate with purity of about 95%.
Example 3 a method for enzymatically synthesizing soyasterol oleate by magnetic induction electric field catalysis comprises the following steps:
s1, raw material pretreatment: placing soyasterol in an oven at 50 ℃, drying for 20h, placing in a dryer, cooling to room temperature according to the ratio of 1 mmol: adding 15ml of the mixture into a beaker at the same time, uniformly mixing, and oscillating for 24 hours at the temperature of 30 ℃;
s2, constructing a reaction system: weighing soyasterol and oleic acid, mixing according to a molar ratio of 2:1, wherein the total amount is 80g, adding N435 lipase (the dosage is 5% of the total mass of the soyasterol and the oleic acid) serving as a catalyst into the beaker, and uniformly mixing to form a liquid phase reaction system (hereinafter referred to as feed liquid);
s3, magnetic induction electric field circulation treatment: pumping the feed liquid into a magnetic induction electric field reaction device by using a peristaltic pump to fill all coil pipelines of the magnetic induction electric field reaction device, then connecting the feed liquid at an outlet back to a beaker to form a circulating flow path, wherein the flow rate of a treatment tube is 30ml/min, then turning on an excitation power supply, setting an excitation voltage of 750V, the excitation frequency is 200kHz, the terminal temperature of a reaction system is 36 ℃, the catalytic treatment time is kept for 60min, the excitation is finished, and the treatment is finished, wherein the yield of the synthesized soyasterol oleate is about 95 percent under the process condition;
s4, separation and purification: after the reaction is finished, pouring out the feed liquid from the magnetic induction electric field reaction device and flowing back to the beaker, centrifuging at 5000r/min, and using NaHCO with the concentration of 0.5mol/L3Extracting the solution for 5 times, collecting the upper layer solution, washing with anhydrous ethanol for 3 times, and drying under 0.12MPa to obtain soyasterol oleate with purity of about 97%.
It should be noted that the foregoing embodiments are merely exemplary illustrations of the present invention, and various process conditions adopted therein are typical examples, but through a great deal of experimental verification by the inventors of the present invention, other process conditions listed above are also applicable, and the claimed technical effects of the present invention can also be achieved.
It should be understood that the above-mentioned embodiments are merely illustrative of the technical concepts and features of the present invention, which are intended to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and therefore, the protection scope of the present invention is not limited thereby. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (10)
1. A method for synthesizing soyasterol oleate by using magnetic induction electric field catalysis enzyme is characterized by comprising the following steps: the method comprises the steps of taking soyasterol and oleic acid as raw materials, and catalytically synthesizing soyasterol oleate under the conditions of a magnetic induction electric field and the presence of enzyme serving as a catalyst.
2. The method for enzymatically synthesizing soyasterol oleate with the magnetic induction electric field as claimed in claim 1, which comprises: and (2) inputting a liquid phase reaction system containing uniformly mixed soyasterol, oleic acid and a catalyst into a magnetic induction electric field reaction device, and reacting the liquid phase reaction system in a magnetic induction electric field provided by the magnetic induction electric field reaction device to obtain the soyasterol oleate.
3. The method for enzymatically synthesizing soyasterol oleate by using the magnetic induction electric field as claimed in claim 1 or 2, wherein: the molar ratio of the soyasterol to the oleic acid is 1:1-2: 1.
4. The method for enzymatically synthesizing soyasterol oleate by using the magnetic induction electric field as claimed in claim 1 or 2, wherein: the mass of the catalyst is 4-8% of the total mass of the soyasterol and the oleic acid.
5. The method for enzymatically synthesizing soyasterol oleate with the magnetic induction electric field as claimed in claim 2, wherein: the liquid phase reaction system also comprises isooctane, and the dosage ratio of the isooctane to the soyasterol is 10-20 ml: 1 mmol.
6. The method for enzymatically synthesizing soyasterol oleate with the magnetic induction electric field as claimed in claim 2, further comprising: drying soyasterol at 40-60 ℃ for 18-30h, placing in a dryer, cooling to room temperature, mixing with isooctane, oscillating at 25-35 ℃ for 24-48h, and sequentially mixing with oleic acid and a catalyst to form the liquid-phase reaction system.
7. The method for enzymatically synthesizing soyasterol oleate with the magnetic induction electric field as claimed in claim 2, wherein: the flow rate of the liquid phase reaction system in a magnetic induction electric field is 20-40ml/min, the terminal temperature of the liquid phase reaction system is 34-36 ℃, and the reaction time is 30-60 min; and/or the liquid phase reaction system circularly flows in the magnetic induction electric field.
8. The method for enzymatically synthesizing soyasterol oleate with the magnetic induction electric field as claimed in claim 1 or 2, wherein the relevant operating parameters of the magnetic induction electric field comprise: the excitation voltage is 600-900V, and the excitation frequency is 180-200 kHz.
9. The method for enzymatically synthesizing soyasterol oleate by using the magnetic induction electric field as claimed in claim 1 or 2, wherein: the catalyst comprises N435 lipase.
10. The method for enzymatically synthesizing soyasterol oleate with the magnetic induction electric field as claimed in claim 2, further comprising: after the reaction is finished, centrifuging the obtained reaction mixture for more than 30s at the rotating speed of 3000-8000 r/min, and then, taking NaHCO with the concentration of 0.3-0.6mol/L3Extracting the solution for more than 3 times, washing the upper layer solution with anhydrous ethanol for more than 3 times, and drying under vacuum condition with air pressure of 0.12-0.15 MPa.
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