CN101225414A - Novel method for extracting natural vitamin E, phytosterol, fatty acid methyl ester by enzyme catalysis and molecular distillation - Google Patents

Novel method for extracting natural vitamin E, phytosterol, fatty acid methyl ester by enzyme catalysis and molecular distillation Download PDF

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CN101225414A
CN101225414A CNA200810049033XA CN200810049033A CN101225414A CN 101225414 A CN101225414 A CN 101225414A CN A200810049033X A CNA200810049033X A CN A200810049033XA CN 200810049033 A CN200810049033 A CN 200810049033A CN 101225414 A CN101225414 A CN 101225414A
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fatty acid
lipase
methyl ester
acid methyl
sterol
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CN101225414B (en
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谷克仁
肖咏梅
王宏雁
江秀明
夏萍
郑丽梅
王秀花
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Tanghe Jinhai Biological Technology Co. Ltd.
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Henan University of Technology
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Abstract

The invention relates to a method to extract a natural vitamin E, a phytosterin, and a fatty acid methyl ester by the enzyme catalysis and the molecular distillation, which is characterized in that a triglyceride in a distillate which is deodorized from a vegetable oil is hydrolyzed into a fatty acid through a lipase, a methanol is catalyzed by the lipase and the fatty acid is esterified and generated into a fatty acid methyl ester, and the natural vitamin E and the phytosterin are produced when the methanol and the fatty acid methyl ester are processed by filtering, desolventizing, freezing and removing the phytosterin, and removing the fatty acid methyl ester through the secondary molecular distillation. The the extraction method of natural vitamin E, phytosterin, and fatty acid methyl este, compared with the prior art, has the advantages of adopting the process that the oil is catalyzed and hydrolyzed first and then the enzyme catalyzes the fat to be esterified and to be processed by the secondary molecular distillation, no producing wastewater, shortening the esterification time, increasing the natural vitamin E content, deploying the secondary freezing and crystallization to remove the phytosterin with high recovery rate of phytosterin, and beneficially increasing the purity of the vitamin E.

Description

Enzyme catalysis, molecular distillation extract natural VE, plant sterol, fatty acid methyl ester novel method
Technical field
The present invention relates to a kind of enzyme catalysis, molecular distillation extraction natural VE, plant sterol, fatty acid methyl ester novel method.
Background technology
Natural tocopherol has eight kinds of isomer, i.e. alpha-tocopherol, 5,8-dimethyl tocol, Gamma-Tocopherol, Delta-Tocopherol and alpha-tocotrienol, β-tocotrienols, γ-tocotrienols, δ-tocotrienols.Eight kinds of isomer of natural VE all have opticity.Wherein the optical activity of (RRR)-alpha-tocopherol is very little.Specific rotatory power (in the pure isooctane) is+0.16 ° only, specific rotatory power in the ethanol [α] 25 546.1Be+0.32 °.5,8-dimethyl tocol specific rotatory power [α] 25 546.1Be by+2.9 ° (c=7.15 is in ethanol).Gamma-Tocopherol specific rotatory power [α] 25 546.1Be by+2.2 ° (c=9.32 is in ethanol).Delta-Tocopherol specific rotatory power [α] 25 546.1Be by+3.4 ° (c=15.5 is in ethanol).
Natural VE is a kind of faint yellow thick transparent liquid, and odorless is tasteless.Natural VE is water insoluble, dissolves in ethanol, acetone, chloroform, acetone.Its density is 0.947～0.955g/m 3(25 ℃), fusing point is 2.5-3.5 ℃, boiling point is 200-220 ℃ under the 66.7Pa.To thermally-stabilised, do not decompose even be heated to 120 ℃ yet.But easily oxidized, under the situation that aerobic exists, can slow oxidation become garnet.Especially oxygenolysis very easily under alkaline condition, ultraviolet ray can promote its decomposition.
Vitamin-E character is very active.Then stable many of their ester derivative such as acetic ester, succinate.Vitamin-E is a powerful antioxidant, itself is easy to oxidized.This must note in vitamin-E extraction, purifying and storage process.Under the condition of gentleness, as in the presence of superoxide, singlet oxygen, oxygen etc., the oxidative pathway of vitamin-E and product are very complicated.The oxidative pathway of different vitamin-Es is different with product.Oxidising process is influenced by illumination, metal ion, substrate, solvent, vitamin-E concentration, temperature, pH value etc. also.
Plant sterol is at the nature ubiquity, different floristics, and its content difference be it is generally acknowledged, vegetables oil and processing byproduct thereof are the abundantest natural sources of plant sterol, contain campesterol, Stigmasterol and β-Gu Zaichun in 16 vegetable oil mostly.Except campesterol, Stigmasterol and three kinds of main sterols of β-Gu Zaichun are prevalent in each kind of plant, other sterol just is present in the certain plants.
Sterol is generally sheet or powdery white solid, the sterol of handling through solvent crystallization is white flakey or needle-like crystal, wherein crystallization is needle-like or water chestnut sheet in alcohol solvent, forms needle prick shape or long prism shape in the ethylene dichloride solvent, forms needle-like or tabular crystal in acetone solvent.In the sterol molecule, carbonatoms is generally 27-31, and molecular weight is between 386-456.The sterol fusing point is higher, all more than 100 ℃, is up to 215 ℃.The sterol relative density is slightly larger than water, and is water insoluble, dissolves in multiple organic solvent.Plant sterol has emulsifying property.Sterol is as the free alcohol compound, can with lipid acid or phenolic acid generation esterification, also can combine with hydro carbons.
Fatty acid methyl ester is a kind of important source material of chemical industry, also is present alleged biofuel, and its physical and chemical performance and petrifaction diesel are close, and can directly replace diesel oil or dissolve each other with arbitrary proportion with diesel oil replacing the petrifaction diesel use.
Plant oil deodorizing distillate is preparation natural VE, the main industrial source of plant sterol, and byproduct is a fatty acid methyl ester.
Plant oil deodorizing distillate is often because of the kind of vegetables oil, its contained V of the difference of the deodorizing technology equipment of the difference in source and vegetables oil EWith sterol also can be different.Deodorization distillate is about 0.3～0.6% of vegetables oil, and main component has the sterol of free fatty acids (comprising linolic acid, oleic acid, palmitinic acid etc.), 10%-20% tri-glyceride, 10%-35% of 30%-60% and sterol ester, the natural VE (tocopherol) of 1%-20%, hydro carbons of 10%-30% etc.
Extraction natural VE and sterol adopt physico-chemical processes such as extraction, molecular distillation, rectifying, absorption, chromatogram usually from deodorization distillate.But, because the physicochemical property difference of each component is little, and vitamin-E be easy to oxidized, so directly from deodorization distillate, extract often difficulty relatively of high-load vitamin-E and sterol.
The patent ZL200510114851 of Zhonggu Tianke (Tianjin) Bioengineering Co., Ltd. provides the method for utilizing distillation depickling, base catalysis esterification, cold analysis, level Four molecular distillation, extracts the method for natural VE from plant oil deodorizing distillate.Adopt the base catalysis esterification, can cause the part vitamin-E destroyed.And the generation alkaline waste water, contaminate environment could be discharged after needing to handle.
People's patent of invention ZL200410008678.0 such as Tsing-Hua University Liu De China, Du Wei, provide to utilize to have lipase Novozym435, the Lipozyme TL of esterification function, the lipid acid in the Lipozyme RM direct esterification plant oil deodorizing distillate, utilized conventional rectification technology to realize the isolating method of vitamin-E, sterol and fatty acid monoester then.Owing to contain more tri-glyceride in the plant oil deodorizing distillate, and lipase Novozym435, Lipozyme TL, Lipozyme RM are effective to free fatty acids and short carbon chain alcohol catalyzing esterification, and it is poor to tri-glyceride and short carbon chain alcohol transesterify catalytic effect, can not make tri-glyceride be converted into fatty acid ester fully, cause difficulty for the purification of vitamin-E, the content of vitamin E that obtains is not high.From the embodiment of this patent as can be seen, this method adopts three esterifications, and the time is long, and technology is loaded down with trivial details in actual production.Utilize conventional distillating method to destroy bigger in this method to vitamin-E.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, the lipase-catalyzed tri-glyceride hydrolysis of the category-A that provides a kind of utilization to have catalyzing glycerol three acid esters hydrolysis functions, the lipase-catalyzed esterification of category-B, freezing and crystallizing, molecular distillation with catalysis lipid acid and short carbon chain alcohols esterification function extract the novel method of natural VE and sterol from plant oil deodorizing distillate.
The objective of the invention is to be achieved through the following technical solutions:
Enzyme catalysis of the present invention, molecular distillation extract natural VE, plant sterol, fatty acid methyl ester novel method, be with the tri-glyceride in the plant oil deodorizing distillate, at first through lipase hydrolysis generate lipid acid, lipase-catalyzed methyl alcohol and fatty acid esterification generate fatty acid methyl ester then, remove fatty acid methyl ester by the quadratic component distillation, and obtain natural VE and sterol, concrete processing step is as follows:
(1) hydrolysis
Add a certain amount of water and lipase A at plant oil deodorizing distillate, the weight ratio of overhead product and water is 1: 0.1-5.0, and the add-on of lipase A is the 0.5%-8% of overhead product weight, at temperature 20-80 ℃, reacted 1-14 hour, and made the tri-glyceride hydrolysis in the material;
(2) esterification
Adopt immobilized lipase B to make catalyzer, the esterification of free lipid acid and methyl alcohol in the catalysis deodorization distillate, make the lipid acid that dissociates in the raw material be transformed into its methyl esters, overhead product and methyl alcohol mol ratio are 1: 1-3, temperature 20-70 ℃, reaction times 1-14 hour, the lipase B consumption was the 0.1-3.5% of plant oil deodorizing distillate weight;
(3) filter
After reaction is finished, be suction filtration under the 0.01-0.05MPa condition, lipase is told from material, recycling at pressure;
(4) precipitation
Is under 0.02-0.06MPa, temperature 50-70 ℃ with filtering the material of removing lipase at pressure, and excessive methanol is reclaimed in evaporation;
(5) the freezing sterol that takes off
The material of precipitation kept 1-12 hour to 2-10 ℃ so that 1-2 ℃/hr is freezing, and suction filtration is removed the crystalline sterol rapidly then;
(6) molecular distillations
The plant oil deodorizing distillate of handling through step (1), (2), (3), (4), (5), distillation gently is a fatty acid methyl ester for the first time mutually under temperature 80-120 ℃, pressure 0.1-10Pa condition;
(7) quadratic component distillation
The heavy phase that step (6) obtains distillation under temperature 100-180 ℃, pressure 0.1-10Pa condition gently is the vitamin-E product for the second time mutually;
(8) the freezing sterol that takes off
Heavy phase through step (7) obtains kept 1-12 hour to 2-10 ℃ so that 1-2 ℃/hr is freezing, and suction filtration is removed the crystalline sterol rapidly then, and the filtrate backwater is separated and reused.
In the present invention, described lipase A is any one among lipase Lipolase-100T, Lipolase-100L, Lipopex-100T or the Lipopex-100L, and described lipase B is any one among lipase Novozym435, Novozym735 or the LipozymeTL IM.
In the step of the present invention (1), the weight ratio of overhead product and water is 1: 0.5-3.0, hydrolysis temperature are 25-75 ℃.Hydrolysis time is 2-10 hour.The add-on of lipase A is the 0.8%-5.0% of overhead product weight.
In the step of the present invention (2), the add-on of lipase B is the 0.5%-3% of overhead product weight.
In step of the present invention (6) and (7), molecular distillation apparatus can be selected single mode for use, also can select the twin-stage pattern for use; Molecular distillation pressure is 1-10Pa; In step (6) and (7), the molecular distillation temperature is respectively: one-level is 90-110 ℃, and secondary is 120-180 ℃.
Operational path of the present invention is seen accompanying drawing.
Substantive distinguishing features of the present invention is with the tri-glyceride in the plant oil deodorizing distillate, at first through lipase hydrolysis generate lipid acid, lipase-catalyzed methyl alcohol and fatty acid esterification generate fatty acid methyl ester then, remove fatty acid methyl ester by the quadratic component distillation, improve natural VE content.The hydrolysis of this process using enzyme catalysis tri-glyceride, enzyme catalysis fatty acid esterification, quadratic component distillation novel process then do not produce waste water, have shortened esterification time, have improved the content of natural VE.The freezing cleaning of this process using secondary removes sterol, sterol rate of recovery height.Help the raising of vitamin-E purity.
Description of drawings
Accompanying drawing is a process route chart of the present invention.
Embodiment
The present invention once is further described in conjunction with the embodiments, but is not restriction the present invention.
Example 1
A kind of method of extracting natural VE from plant oil deodorizing distillate comprises the steps:
(1) hydrolysis adds lipase Lipolase-100T in plant oil deodorizing distillate, enzyme concn 1.0% (add-on that is lipase be overhead product weight 1%) adds the water of material equivalent, 55 ℃ of temperature of reaction, hydrolysis time 10 hours.
(2) esterification, the material that after handle (1) set by step, obtains, the adding mol ratio is 1: 1 a methyl alcohol, add lipase Novozym435, enzyme concn 0.5% (be the lipase consumption be plant oil deodorizing distillate weight 0.5%), 35 ℃ of temperature of reaction, 2 hours reaction times.
(3) filtering, is suction filtration under the 0.05MPa condition at pressure, and lipase is told from material, can reuse.
(4) precipitation is under 0.06MPa, temperature 50-70 ℃ with filtering the material of removing lipase at pressure, and excessive methanol is reclaimed in evaporation.
(5) the freezing sterol that takes off, the material of precipitation is freezing to 4 ℃ with 1 ℃/hr, and crystallization 12 hours removes by filter crystallization of sterols.
(6) molecular distillations through the material of freezing and filtering, carry out first time and distill under 120 ℃, pressure 5Pa condition, gently be fatty acid methyl ester mutually,
(7) quadratic component distillation, the heavy phase that step (6) obtains is distilled under 140 ℃, pressure 1Pa condition, gently is natural VE mutually, and purity 38%, heavy phase are returned step (2).
(8) the freezing sterol that takes off, the material that step (7) obtains is freezing to 4 ℃ with 1 ℃/hr, and crystallization 12 hours removes by filter crystallization of sterols.The sterol purity that step (5) and step (8) obtain is 74%.
Example 2
A kind of method of extracting natural VE from plant oil deodorizing distillate comprises the steps:
(1) hydrolysis adds lipase Lipolase-100L in plant oil deodorizing distillate, enzyme concn 2.0% (add-on that is lipase be overhead product weight 2%), and material: water is 1: 1,50 ℃ of temperature of reaction, 11 hours reaction times.
(2) esterification, the material that after handle (1) set by step, obtains, the adding mol ratio is 1: 1.5 a methyl alcohol, add lipase Novozym735, enzyme concn 1.0% (be the lipase consumption be plant oil deodorizing distillate weight 1.0%), 45 ℃ of temperature of reaction, 4 hours reaction times.
(3) filtering, is suction filtration under the 0.06MPa condition at pressure, lipase is told recycling from material.
(4) precipitation, under pressure was 50 ℃ of 0.06MPa, temperature, excessive methanol was reclaimed in evaporation with material that filter to remove lipase B.
(5) the freezing sterol that takes off, the material of precipitation is freezing to 4 ℃ with 1 ℃/hr, and crystallization 10 hours filters crystallization.
(6) molecular distillations through the material of freezing and filtering, carry out first time and distill under 110 ℃, pressure 2.5Pa condition, gently be fatty acid methyl ester mutually,
(7) quadratic component distillation, the heavy phase that step (6) obtains is distilled under 150 ℃, pressure 2Pa condition, gently is natural VE mutually, and purity 38%, heavy phase are returned step (2).
(8) the freezing sterol that takes off, the material of precipitation is freezing to 4 ℃ with 1 ℃/hr, and crystallization 12 hours filters crystallization of sterols.The sterol purity that step (5) and step (8) obtain is 74.5%.
Example 3
A kind of method of extracting natural VE from plant oil deodorizing distillate comprises the steps:
(1) hydrolysis adds lipase Lipopex-100T in plant oil deodorizing distillate, enzyme concn 3.0% (add-on that is lipase be overhead product weight 3%), and material: water is 1: 1.5,55 ℃ of temperature of reaction, 12 hours reaction times, hydrolysis.
(2) esterification after the material that obtains in (1) is set by step handled, adds mol ratio and is 1: 1.8 methyl alcohol, add lipase LipozymeTL IM, enzyme concn 1.5% (be the lipase consumption be plant oil deodorizing distillate weight 1.5%), 50 ℃ of temperature of reaction, 6 hours reaction times.
(3) filtering, is suction filtration under the 0.05MPa condition at pressure, lipase is told recycling from material.
(4) precipitation, under pressure was 60 ℃ of 0.05MPa, temperature, excessive methanol was reclaimed in evaporation with material that filter to remove lipase.
(5) the freezing sterol that takes off, the material of precipitation is freezing to 2 ℃ with 2 ℃/hr, and crystallization 9 hours removes by filter crystallization.
(6) molecular distillations through the material of freezing and filtering, carry out first time and distill under 100 ℃, pressure 3.5Pa condition, gently be fatty acid methyl ester mutually,
(7) quadratic component distillation, the heavy phase that step (6) obtains is distilled under 160 ℃, pressure 1Pa condition, gently is natural VE mutually, and purity 39%, heavy phase are returned step (2).
(8) the freezing sterol that takes off, the material of precipitation is freezing to 4 ℃ with 1 ℃/hr, and crystallization 12 hours filters crystallization of sterols.The sterol purity that step (5) and step (8) obtain is 74%.
Example 4
A kind of method of extracting natural VE from plant oil deodorizing distillate comprises the steps:
(1) hydrolysis adds lipase Lipopex-100L in plant oil deodorizing distillate, enzyme concn 2.0% (add-on that is lipase be overhead product weight 2%), and material: water is 1: 1,50 ℃ of temperature of reaction, 11 hours reaction times, hydrolysis.
(2 esterifications, in the plant oil deodorizing distillate material, the adding mol ratio is 1: 2 a methyl alcohol, add lipase Novozym435, enzyme concn 2.5% (be the lipase consumption be plant oil deodorizing distillate weight 2.5%), 30 ℃ of temperature of reaction, 10 hours reaction times, esterification.
(3) filtering, is suction filtration under the 0.05MPa condition at pressure, lipase B is told recycling from material.
(4) precipitation, under pressure was 60 ℃ of 0.05MPa, temperature, excessive methanol was reclaimed in evaporation with material that filter to remove lipase.
(5) freezing suction filtration, the material of precipitation is freezing to 2 ℃ with 2 ℃/hr, and crystallization 11 hours filters crystallization.
(6) molecular distillations through the material of freezing and filtering, carry out first time and distill under 100 ℃, pressure 1.5Pa condition, gently be fatty acid methyl ester mutually.
(7) quadratic component distillation, the heavy phase that step (6) obtains is distilled under 150 ℃, pressure 1Pa condition, gently is natural VE mutually, and purity 38%, heavy phase are returned step (2).
(8) the freezing sterol that takes off, the material of precipitation is freezing to 4 ℃ with 1 ℃/hr, and crystallization 12 hours filters crystallization of sterols.The sterol purity that step (5) and step (8) obtain is 74%.
Example 5
A kind of method of extracting natural VE from plant oil deodorizing distillate comprises the steps
(1) hydrolysis adds lipase Lipolase-100L in plant oil deodorizing distillate, enzyme concn 3.5% (add-on that is lipase be overhead product weight 3.5%), and material: water is 1: 1.5,60 ℃ of temperature of reaction, 12 hours reaction times, hydrolysis.
(2) esterification, in the plant oil deodorizing distillate material, the adding mol ratio is 1: 2 a methyl alcohol, add lipase Novozym435, enzyme concn 2.5% (be the lipase consumption be plant oil deodorizing distillate weight 2.5%), 30 ℃ of temperature of reaction, 10 hours reaction times, esterification.
(3) filtering, is suction filtration under the 0.05MPa condition at pressure, lipase B is told recycling from material.
(4) precipitation, under pressure was 60 ℃ of 0.05MPa, temperature, excessive methanol was reclaimed in evaporation with material that filter to remove lipase.
(5) freezing suction filtration, the material of precipitation is freezing to 2 ℃ with 2 ℃/hr, and crystallization 12 hours filters crystallization.
(6) molecular distillations through the material of freezing and filtering, carry out first time and distill under 100 ℃, pressure 1.5Pa condition, gently be fatty acid methyl ester mutually,
(7) quadratic component distillation, the heavy phase that step (6) obtains is distilled under 150 ℃, pressure 1Pa condition, gently is natural VE mutually, and purity 52%, heavy phase are returned step (2).
(8) the freezing sterol that takes off, the material of precipitation is freezing to 4 ℃ with 1 ℃/hr, and crystallization 12 hours filters crystallization of sterols.The sterol purity that step (5) and step (8) obtain is 75%.

Claims (10)

1. an enzyme catalysis, molecular distillation extract natural VE, plant sterol, fatty acid methyl ester novel method, it is characterized in that: be the tri-glyceride in the plant oil deodorizing distillate, at first through lipase hydrolysis generate lipid acid, lipase-catalyzed methyl alcohol and fatty acid esterification generate fatty acid methyl ester then, remove fatty acid methyl ester by the quadratic component distillation, and obtain natural VE and sterol, concrete processing step is as follows:
(1), hydrolysis
Add a certain amount of water and lipase A at plant oil deodorizing distillate, the weight ratio of overhead product and water is 1: 0.1-5.0, and the add-on of lipase A is the 0.5%-8% of overhead product weight, at temperature 20-80 ℃, reacted 1-14 hour, and made the tri-glyceride hydrolysis in the material;
(2), esterification
Adopt immobilized lipase B to make catalyzer, the esterification of free lipid acid and methyl alcohol in the catalysis deodorization distillate, make the lipid acid that dissociates in the raw material be transformed into its methyl esters, overhead product and methyl alcohol mol ratio are 1: 1-3, temperature 20-70 ℃, reaction times 1-14 hour, the lipase B consumption was the 0.1-3.5% of plant oil deodorizing distillate weight;
(3), filter
After reaction is finished, be suction filtration under the 0.01-0.05MPa condition, lipase is told from material, recycling at pressure;
(4), precipitation
Is under 0.02-0.06MPa, temperature 50-70 ℃ with filtering the material of removing lipase at pressure, and excessive methanol is reclaimed in evaporation;
(5), the freezing sterol that takes off
The material of precipitation kept 1-12 hour to 2-10 ℃ so that 1-2 ℃/hr is freezing, and suction filtration is removed the crystalline sterol rapidly then;
(6), molecular distillation
Through the plant oil deodorizing distillate that handle step (1), (2), (3), (4), (5), distillation gently is a fatty acid methyl ester for the first time mutually under temperature (80-120 ℃), pressure (0.1-10Pa) condition;
(7), quadratic component distillation
The heavy phase that step (6) obtains is distilled under temperature (100-180 ℃), pressure (0.1-10Pa) condition for the second time, gently is the vitamin-E product mutually;
(8) the freezing sterol that takes off
Heavy phase through step (7) obtains kept 1-12 hour to 2-10 ℃ so that 1-2 ℃/hr is freezing, and suction filtration is removed the crystalline sterol rapidly then, and the filtrate backwater is separated and reused.
2. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method, it is characterized in that: described lipase A is any one among lipase Lipolase-100T, Lipolase-100L, Lipopex-100T or the Lipopex-100L, and described lipase B is any one among lipase Novozym435, Novozym735 or the LipozymeTL IM.
3. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (1), the weight ratio of overhead product and water is 1: 0.5-3.0.
4. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (1), the add-on of lipase A is the 0.8%-5.0% of overhead product weight.
5. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (1), hydrolysis temperature is 25-75 ℃.
6. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (1), hydrolysis time is 2-10 hour.
7. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (2), the add-on of lipase B is the 0.5%-3% of overhead product weight.
8. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (6) and (7), molecular distillation apparatus can be selected single mode for use, also can select the twin-stage pattern for use.
9. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (6) and (7), molecular distillation pressure is 1-10Pa.
10. extraction natural VE according to claim 1, plant sterol, fatty acid methyl ester novel method is characterized in that: in step (6), the molecular distillation temperature is 90-110 ℃, and in step (7), the molecular distillation temperature is 120-180 ℃.
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CN109943600A (en) * 2019-04-15 2019-06-28 山东新元素生物科技有限公司 A kind of preparation method of low acid value biodiesel and vitamin E
CN110257445A (en) * 2019-06-28 2019-09-20 中粮天科生物工程(天津)有限公司 Biodiesel, the method for natural VE and phytosterol are prepared from plant oil deodorizing distillate
CN110627802A (en) * 2018-06-21 2019-12-31 财团法人食品工业发展研究所 Method for extracting sesame lignan from by-product generated in sesame oil production
CN111875657A (en) * 2020-07-31 2020-11-03 福建省格兰尼生物工程股份有限公司 Deodorized distillate suitable for biological enzyme esterification reaction and preparation method thereof
CN111926047A (en) * 2020-08-25 2020-11-13 福建省格兰尼生物工程股份有限公司 Repeated application production method for esterification reaction of low-temperature bio-enzyme catalysis deodorized distillate
CN112159384A (en) * 2020-09-07 2021-01-01 山西农业大学 Soybean vitamin E extraction device and extraction method
CN112941126A (en) * 2021-04-01 2021-06-11 福建省格兰尼生物工程股份有限公司 Method for extracting soybean vitamin E from non-soybean deodorized distillate
CN115650943A (en) * 2022-09-13 2023-01-31 宜春大海龟生命科学有限公司 Method for enriching polyunsaturated fatty acid ester, squalene, natural vitamin E and phytosterol from plant deodorized distillate
CN115747266A (en) * 2023-01-05 2023-03-07 苏州丰倍生物科技股份有限公司 Method for producing fatty acid methyl ester by lipase catalysis

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CN106146606A (en) * 2015-04-13 2016-11-23 漳州金富顺生物科技有限公司 In a kind of natural Vitamin E production process, evaporative crystallization reclaims plant sterol method
CN105695105A (en) * 2016-01-13 2016-06-22 常州市金坛区维格生物科技有限公司 Method for co-producing fatty acid methyl ester, vitamin E and phytosterol from carclazyte oil
CN106117297B (en) * 2016-06-28 2019-02-26 西安国邦实业有限公司 The preparation method of one plant sterols and sterol ester
CN106117297A (en) * 2016-06-28 2016-11-16 西安国邦实业有限公司 One plant sterols and the preparation method of sterol ester
CN106146595A (en) * 2016-06-28 2016-11-23 西安国邦实业有限公司 A kind of method extracting steroid enol from plant oil deodorizing distillate
CN106146595B (en) * 2016-06-28 2018-01-02 西安国邦实业有限公司 A kind of method that steroid enol is extracted from plant oil deodorizing distillate
CN107012177A (en) * 2017-03-31 2017-08-04 福建省格兰尼生物工程股份有限公司 A kind of method of low-temperature catalyzed deodorization distillate esterification
CN107474093A (en) * 2017-08-23 2017-12-15 福建省格兰尼生物工程股份有限公司 A kind of deodorization distillate continuous production VE, sterol, methyl esters, glycerine, the method for squalene and high-boiling components
CN107474093B (en) * 2017-08-23 2019-07-23 福建省格兰尼生物工程股份有限公司 A kind of method of deodorization distillate continuous production VE, sterol, methyl esters, glycerol, squalene and high-boiling components
CN108299373A (en) * 2018-05-07 2018-07-20 宜春大海龟生命科学有限公司 The method that natural VE is extracted from rice bran oil deodorization distillate
CN108299373B (en) * 2018-05-07 2021-01-12 宜春大海龟生命科学有限公司 Method for extracting natural vitamin E from rice bran oil deodorizer distillate
CN108822176A (en) * 2018-06-11 2018-11-16 山东西王食品有限公司 A kind of technique that enzyme process esterification free fatty acid extracts phytosterol
CN110627802A (en) * 2018-06-21 2019-12-31 财团法人食品工业发展研究所 Method for extracting sesame lignan from by-product generated in sesame oil production
CN109456837A (en) * 2018-09-30 2019-03-12 东北农业大学 A kind of method of free fatty acid and removing water in products point in continuous esterification Rice bran crude oil
CN109609286A (en) * 2018-12-29 2019-04-12 新疆昊睿新能源有限公司 A method of extracting phytosterol from cottonseed acidification oil
CN109943600A (en) * 2019-04-15 2019-06-28 山东新元素生物科技有限公司 A kind of preparation method of low acid value biodiesel and vitamin E
CN110257445A (en) * 2019-06-28 2019-09-20 中粮天科生物工程(天津)有限公司 Biodiesel, the method for natural VE and phytosterol are prepared from plant oil deodorizing distillate
CN111875657A (en) * 2020-07-31 2020-11-03 福建省格兰尼生物工程股份有限公司 Deodorized distillate suitable for biological enzyme esterification reaction and preparation method thereof
CN111926047A (en) * 2020-08-25 2020-11-13 福建省格兰尼生物工程股份有限公司 Repeated application production method for esterification reaction of low-temperature bio-enzyme catalysis deodorized distillate
CN112159384A (en) * 2020-09-07 2021-01-01 山西农业大学 Soybean vitamin E extraction device and extraction method
CN112941126A (en) * 2021-04-01 2021-06-11 福建省格兰尼生物工程股份有限公司 Method for extracting soybean vitamin E from non-soybean deodorized distillate
CN115650943A (en) * 2022-09-13 2023-01-31 宜春大海龟生命科学有限公司 Method for enriching polyunsaturated fatty acid ester, squalene, natural vitamin E and phytosterol from plant deodorized distillate
CN115650943B (en) * 2022-09-13 2024-02-27 宜春大海龟生命科学股份有限公司 Method for enriching polyunsaturated fatty acid ester, squalene, natural vitamin E and phytosterol from plant deodorization distillate
CN115747266A (en) * 2023-01-05 2023-03-07 苏州丰倍生物科技股份有限公司 Method for producing fatty acid methyl ester by lipase catalysis

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